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Isolation and Identification of Flavones Responsible for the Antibacterial Activities of Tillandsia bergeri Extracts

  • Mame-Marietou Lo
    Mame-Marietou Lo
    UNIV. NIMES, UPR CHROME, 5 rue du Dr Georges Salan, F-30021 Nîmes Cedex 1, France
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  • Zohra Benfodda
    Zohra Benfodda
    UNIV. NIMES, UPR CHROME, 5 rue du Dr Georges Salan, F-30021 Nîmes Cedex 1, France
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    Orcidhttps://orcid.org/0000-0001-7574-4977
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  • Catherine Dunyach-Rémy
    Catherine Dunyach-Rémy
    Institut National de la Santé et de la Recherche Médicale, U1047, Montpellier University, CHU de Nîmes, Place du Pr R. Debré, 30029 Nîmes, France
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  • David Bénimélis
    David Bénimélis
    UNIV. NIMES, UPR CHROME, 5 rue du Dr Georges Salan, F-30021 Nîmes Cedex 1, France
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  • Romain Roulard
    Romain Roulard
    UMR 1158 Transfontalière BioEcoAgro, BIOlogie des Plantes et Innovation (BIOPI), UPJV, Faculté de Pharmacie, 1 rue des Louvels, 80025 Amiens CEDEX, France
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  • Jean-Xavier Fontaine
    Jean-Xavier Fontaine
    UMR 1158 Transfontalière BioEcoAgro, BIOlogie des Plantes et Innovation (BIOPI), UPJV, Faculté de Pharmacie, 1 rue des Louvels, 80025 Amiens CEDEX, France
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  • David Mathiron
    David Mathiron
    Plateforme-Analytique, Université de Picardie Jules Verne, 33 rue Saint Leu, 80039 Amiens, France
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  • Anthony Quéro
    Anthony Quéro
    UMR 1158 Transfontalière BioEcoAgro, BIOlogie des Plantes et Innovation (BIOPI), UPJV, Faculté de Pharmacie, 1 rue des Louvels, 80025 Amiens CEDEX, France
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  • Roland Molinié
    Roland Molinié
    UMR 1158 Transfontalière BioEcoAgro, BIOlogie des Plantes et Innovation (BIOPI), UPJV, Faculté de Pharmacie, 1 rue des Louvels, 80025 Amiens CEDEX, France
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  • , and 
  • Patrick Meffre*
    Patrick Meffre
    UNIV. NIMES, UPR CHROME, 5 rue du Dr Georges Salan, F-30021 Nîmes Cedex 1, France
    *Email: [email protected]. Phone: +33-466 279 581.
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    Orcidhttps://orcid.org/0000-0002-6189-9860
Cite this: ACS Omega 2022, 7, 40, 35851–35862
Publication Date (Web):September 27, 2022
https://doi.org/10.1021/acsomega.2c04195

Copyright © 2022 The Authors. Published by American Chemical Society. This publication is licensed under

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Abstract

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Plants are an everlasting inspiration source of biologically active compounds. Among these medicinal plants, the biological activity of extracts from some species of the Tillandsia genus has been studied, but the phytochemistry of the hardy species Tillandsia bergeri remains unknown. The aim of the present study was to perform the first phytochemical study of T. bergeri and to identify the compounds responsible for the antibacterial activity of T. bergeri extracts. Soxhlet extraction of predried and grinded leaves was first performed using four increasing polarity solvents. A bio-guided fractionation was performed using agar overlay bioautography as a screening method against 12 Gram-positive, Gram-negative, sensitive, and resistant bacterial strains. The results showed the inhibition of Gram-positive methicillin-sensitive Staphylococcus aureus ATCC 29213 (MSSA), methicillin-resistant S. aureus N-SARM-1 (MRSA), and Staphylococcus caprae ATCC 35538 by the dichloromethane fraction. A phytochemical investigation led to the isolation and identification by high-resolution mass spectrometry and nuclear magnetic resonance of the two flavones penduletin and viscosine, responsible for this antibacterial activity. For viscosine, the minimum inhibitory concentration (MIC) value is equal to 128 μg/mL against MSSA and is equal to 256 μg/mL against MRSA and S. caprae. The combination of these compounds with vancomycin and cloxacillin showed a decrease in MICs of the antibiotics. Penduletin showed synergistic activity when combined with vancomycin against MSSA (FICI < 0.258) and S. caprae (FICI < 0.5). Thus, unexplored Tillandsia species may represent a valuable source for potential antibiotics and adjuvants.

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Introduction

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Natural products from plants have long been known to inspire medicinal chemists for new drugs (1,2) in the fields of antiviral, (3) anticancer, (4,5) or antibacterial (6) agents among others.
Tillandsia is one of the 57 plant genera belonging to the Bromeliaceae family, a well-known family of monocotyledons endemic to the Neotropics. (7−10)Tillandsia is considered to be the most diverse genus in this family and comprises more than 700 species divided into 7 subgenera, of which the main are epiphytes. (7,11,12) The Tillandsia genus has shown some potentialities in pharmacy as a medicinal plant. (13,14)
More than 30 Tillandsia species have been mentioned in traditional Mexican medicine, and this has been reviewed recently by Estrella-Parra et al. in a comprehensive and pluridisciplinary approach including ethnobotany, chemistry, biological activity, and economic issues. (14) Uses in traditional medicine have led researchers to investigate the biological properties of compounds isolated from the extracts of Tillandsia species like Tillandsia streptocarpa (Baker), Tillandsia recurvata, Tillandsia usneoides, Tillandsia aeranthos, and Tillandsia brachycaulos, among others. This allowed to demonstrate the presence of several secondary metabolites, of which the major ones are triterpenoids and sterols (51%), flavonoids (45%), and cinnamic acids (4%), obtained from the organic extracts and presenting a wide range of biological activities such as antimicrobial, antiviral, antiherpetic, anti-inflammatory, antibacterial, hypoglycemic, and anticancer activities. (14)
Owing to the biological activities associated with secondary metabolites from the Tillandsia genus, investigation of the phytochemical composition of the Tillandsia species, especially those that are unstudied so far, can unveil bioactive compounds that have potential medical applications and highlight the economic importance of these plants. (14)
Tillandsia bergeri Mez is a caulescent species, belonging to subgenus Anoplophytum, endemic to Argentina (15−17) with a developed stem and dense clumps (Figure S1). It is a hardy species acclimated to the Mediterranean Riviera. (10,18) To our knowledge, although it is a well-known, cultivated, and commercially ornamental species easy to care for, the phytochemistry and biological applications of T. bergeri remain unstudied.
In this report, we describe the first phytochemical study of T. bergeri with antibacterial screening and identification of the compounds responsible for the activity.
Although possessing compounds of interest, the isolation of secondary metabolites from plants can be an obstacle due to the complexity of the chemical composition of plant extracts. However, thin layer chromatography (TLC) bioautography is an effective screening method to detect and isolate active compounds including antibacterial compounds from plant extracts. (19) This technique is known since 1946 (20) and widely used for the evaluation of several biological activities such as antifungal, antitumor, antiestrogenic, antimutagenic, antioxidant, and antiprotozoal activities. (21) The principle relies on the ability of TLC to separate compounds within a complex matrix and in a relatively short time. This method performs the biological evaluation on the TLC plate to determine directly the biologically active compounds. The bioautography can also be combined with high-performance TLC, overpressured layer chromatography, and planar electrochromatography. (22,23) In order to evaluate antibacterial activities, several TLC bioautography techniques can be performed, such as contact bioautography, direct bioautography, and immersion or agar overlay bioautography. (24) Immersion/agar overlay bioautography is a technique considered to be a combination of contact and direct bioautography; in fact, for this third technique, the agar-bacteria suspension covers the TLC plate during the whole process from incubation to visualization of the inhibition zone. (25,26) For all these bioautography methods, the visualization is done after spraying a solution of tetrazolium salts such as 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide or p-iodonitrotetrazolium (INT) which are transformed into formazan of purple or pink color, respectively, by the dehydrogenases of the living microorganisms. (27−29) The presence of antibacterial compounds is indicated by clear inhibition zones or a white halo on the colored background. TLC bioautography is a time-saving, simple, efficient, inexpensive, and widely used method for bio-guided fractionation of plant extracts. (23)
In order to identify biologically active compounds, they must first be purified and obtained in sufficient quantity. Following this, structural identification is performed using analytical techniques like nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS). Indeed, the combination of these two techniques allows a more efficient structural identification, the advantages of one overcoming the limitations of the other. (30)
The aim of this study is to perform a phytochemical analysis and identify the antibacterial compounds present in T. bergeri. Bio-guided fractionation will be performed using agar overlay bioautography as a screening method against several Gram-positive and Gram-negative bacterial strains as well as one resistant strain. Identification of antibacterial compounds will be done by NMR and HRMS. Minimum inhibitory concentrations (MICs) and synergistic effects of the compounds with conventional antibiotics will be determined.

Experimental Section

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Plant Material and Chemicals

The T. bergeri plants used for this study were harvested in March 2019 from the Tillandsia PROD plant nursery located in Le Cailar (Occitanie, France, 43°41′31.98″N, 4°14′34.85″E) (see Figure S1 in the Supporting Information).
All analytical grade solvents and liquid chromatography (LC)–MS grade solvents used in this report were ordered from VWR (Radnor, Pennsylvania, USA). High-performance LC (HPLC) grade ultrapure water was prepared with a PURELAB Classic water purification system (Elga, Veolia), and analytical grade pure formic acid was purchased from Sigma-Aldrich (St. Louis, Missouri, USA). All Si60 F254 aluminum TLC plates (0.25 mm thickness) and preparative SIL G-200 glass TLC plates (2 mm thickness) were ordered from Merck (Darmstadt, Germany). For chemical TLC development, vanillin, 2-aminoethyl diphenylborinate, polyethylene glycol-4000 (PEG), and p-anisaldehyde were ordered from Sigma-Aldrich, and glacial acetic acid and sulfuric acid were purchased from VWR.
For TLC bioautography, the Mueller–Hinton (MH) broth, MH agar, and Ringer’s solution were ordered from Fisher Scientific (Hampton, New Hampshire, USA), and INT was ordered from Sigma-Aldrich. A standard of penduletin (purity >95%) was ordered from PhytoLab (PhytoLab GmbH & Co., Vestenbergsgreuth, Germany) and that of viscosin (purity >90%) was ordered from Sigma-Aldrich (St. Louis, Missouri, USA). Vancomycin was purchased from Sigma-Aldrich, and cloxacillin was obtained from the microbiology department of the University Hospital of Nı̂mes.

Extraction

T. bergeri leaves were dried in an incubator at 50 °C until the constant point was reached. This was obtained after 6–7 days of drying. Once dried, they were stored in amber glass bottles in a dry and shaded place. Grinding was performed using a SPEX planetary ball grinder with 50 mL bowls containing 1 mm diameter zirconium beads. In this case, a 4 min cycle was performed for a satisfactory powder size. After grinding, four successive extractions were performed in Soxhlet with solvents of increasing polarity, first with hexane, then with dichloromethane, followed by methanol, and finally with methanol/water (50/50), in order to extract the maximum of compounds. A quantity of 30 g of the dried T. bergeri leaf powder was placed in the Soxhlet cartridge, and each extraction was performed for 5 h corresponding to 25 cycles in 350 mL of the appropriate solvent. In total, four large extractions were performed with a total amount of powder of 120 g which allowed us to obtain, after complete dryness, the following fractions noted F1 (3.0 g), F2 (1.3 g), F3 (5.6 g), and F4 (4.2 g) corresponding to the fractions obtained after extraction with hexane, dichloromethane, methanol, and methanol/water (50/50), respectively. The dry extracts were kept cold (−20 °C) until analysis.

Phytochemical Screening

Fractions F1, F2, F3, and F4 were prepared at a concentration of 5 mg/mL and deposited on a silica gel 60 F254 TLC plate (20 × 10 cm) using the Linomat 5 automatic depositor (CAMAG, Muttenz, Switzerland). A deposit of 20 μL was thus carried out in four series for each fraction. The migration was performed with the eluent system chloroform/methanol (90/10) over a distance of 55 mm. The developed TLC plates were visualized under UV 254 and 366 nm using the CAMAG TLC Visualizer. Specific chemical developers were also prepared to visualize the presence of certain chemical families or functions:
Sulfuric vanillin: a solution consisting of 1 g of vanillin, 2 mL of sulfuric acid, and 100 mL of ethanol (95%). The solution was sprayed on the TLC plate which was then heated at 110 °C for 5 min. Several colorations appear depending on the compound.
Anisaldehyde: a solution consisting of 50 mL of glacial acetic acid, 1 mL of sulfuric acid, and 0.5 mL of p-anisaldehyde. The solution thus prepared was sprayed onto the TLC plate, which was subsequently heated to 110 °C for 5 min.
Neu’s reagent (polyphenols): two solutions were prepared, one consisting of 1 g of 2-aminoethyldiphenylboric acid and 100 mL of methanol and the second solution consisting of 5 g of PEG 4000 in 100 mL of ethanol. A mixture of 50 mL of the first solution and 40 mL of the second solution was sprayed onto the TLC plate. The plate was subsequently heated at 110 °C for 2 min. The compounds colored orange, yellow, or green are flavonoids. The TLC plates were then visualized with the CAMAG TLC Visualizer, and pictures were taken with the Vision CATS software.

Bacterial Strains

The antibacterial effect of crude extracts of T. bergeri was first evaluated by agar overlay bioautography against the following bacterial strains: seven Gram-positive bacteria methicillin-sensitive, Staphylococcus aureus ATCC 29213 (MSSA), methicillin-resistant S. aureus N-SARM-1 (MRSA) (clinical strain), Staphylococcus caprae ATCC 35538, Streptococcus agalactiae ATCC 13813, Enterococcus faecalis ATCC 51299, Enterococcus faecium CIP 103226T, Bacillus subtilis subtilis ATCC 6051, and five Gram-negative bacteria, Escherichia coli ATCC 25922, Pseudomonas aeruginosa PAO1 (clinical strain), Proteus mirabilis ATCC 35659, Klebsiella pneumoniae ATCC 700603, and Salmonella enterica indica ATCC 43976. The bacterial strains were obtained from the collection of the Pasteur Institute (Paris, France) except for MSSA, MRSA (clinical strain), and P. aeruginosa PAO1 (clinical strain) which were obtained from the collection of the microbiology department of the University Hospital of Nimes.

TLC Agar Overlay Bioautography

Bacterial suspensions: two colonies of each bacterial strain, listed above, were collected and placed in tubes containing 4 mL of the MH broth; then, the tubes were placed in the shaker incubator at 37 °C and 200 rpm overnight. After the bacteria were grown, twofold dilutions were performed for each bacterial strain (1 mL of the bacterial suspension in 9 mL of Ringer’s liquid) to obtain a concentration of 106 CFU/mL. At the end, 0.50 mL of the bacterial suspension (dilution 2) was then added to 15 mL of MH agar (kept liquid at 45 °C).
TLC plates: a first screening was performed with fractions F1, F2, F3, and F4 of T. bergeri to see which fraction presented antibacterial compounds. For this, each crude extract was prepared at a concentration of 100 mg/mL and deposited, without migration, on the TLC plates. In addition, three antibiotics (cefotaxime, cloxacillin, and ciprofloxacin), used in the treatment of infections caused by these bacteria, and a blank sample (methanol) were applied. When the fraction showed antibacterial activity, TLC separation was performed to determine the compound responsible for the activity. In our case, the F2 fraction of T. bergeri showed activity against MSSA as well as MRSA and S. caprae ATCC 35538 and was manually deposited using a microsyringe Hamilton (Bonaduz, Switzerland). Then, TLC plates were developed with a chloroform/methanol (90/10) eluent at a distance of 55 mm. After separation, the TLC plates were dried to completely remove the solvent. They were then sterilized under UV light and placed in Petri dishes.
15.5 mL of the agar–bacteria suspension was added to the Petri dish containing the TLC plate. After solidification of the medium, incubation was performed for 24 h at 37 °C.
After incubation, a 2 mg/mL solution of INT was sprayed on the surface of the agar–bacteria suspension and incubated again for 4 h. Inhibition is indicated by the presence of clear zones.

Isolation of Antibacterial Compounds

To isolate the antibacterial compounds, two purification methods were used as follows:

Preparative TLC

First, several preparative TLC was performed from the F2 fraction. For this, for each preparative TLC, 100 mg of F2, solubilized in dichloromethane, was deposited on a 2 mm SIL G-200 glass plate using a micropipette. The plate was then placed in a migration chamber containing 100 mL of the chloroform/methanol (90/10) eluent to allow separation of the compounds. The migration was performed twice and was carried out over a distance of 17 cm. After elution, the plate was well dried and then revealed by UV at different wavelengths (254 and 365 nm). The obtained subfractions were scraped, crushed to obtain a powder, and then collected in glass pillboxes before being dissolved in methanol and shaken for 30 min. The methanol/silica mixtures were then filtered to recover the filtrate. The solvent was evaporated to dryness, and the subfractions were weighed. A total of 10 preparative TLCs were performed from F2, allowing 72.4 mg of the subfraction F2.3 and 114.2 mg of F2.5.

Preparative HPLC

The subfractions F2.3 and F2.5 thus obtained were repurified by preparative HPLC to obtain compounds 1 and 2, respectively. They were solubilized in a methanol/ultrapure water mixture (50/50) and then filtered on polytetrafluoroethylene filters (13 mm; 0.22 μm) (Cloup, Champigny-sur-Marne, France). Preparative HPLC was performed with an LC-20AD system (Shimadzu, Kyoto, Japan) equipped with a Shimadzu SIL-10AP autosampler. The separation column was a SUPELCOSIL ABZ+Plus column (25 cm × 22.1 cm; 5 μm) (Sigma, St. Louis, Missouri, USA). Elution was performed with a mobile phase flow rate of 17 mL/min consisting of a mixture of ultrapure water containing 0.05% formic acid (A) and methanol with 0.05% formic acid (B); the program started at t = 0 min, ratio (A/B) 50:50; at t = 20 min, 30:70; at t = 45 min, 5:95; at t = 50 min, 95:5; at t = 55 min, 50:50; and t = 70 min, 50:50. After purification and drying, 4.3 mg of compound 1 and 3.6 mg of compound 2 were obtained.

High-Performance Liquid Chromatography-Ultraviolet

The purity of the active compounds was verified by HPLC-UV on an LC-2010HT system (Shimadzu, Kyoto, Japan). A SUPELCOSIL ABZ+PLUS column (25 cm × 4.6 mm; 5 μm) (Sigma, St. Louis, Missouri, USA) was used to check the purity, with ultrapure water containing 0.05% formic acid and methanol with 0.05% formic acid at a flow rate of 0.8 mL/min. The mobile phase gradient was the same as that used for preparative HPLC.

Identification of Antibacterial Compounds

Ultra-Performance Liquid Chromatography–High-Resolution Mass Spectrometry

The ultra-performance LC coupled to HRMS (UPLC–HRMS) analysis was performed on an ACQUITY UPLC I-class chain coupled to the Vion IMS Quadrupole time-of-flight high-resolution mass spectrometer, equipped with an electrospray ionization (ESI) (Waters, Manchester, UK) source (Z-spray) and an additional spray for the reference compound (Lock Spray). The ionization was performed in positive and negative modes. A double detection was performed by ESI mass spectrometry (range 50–2000 Da) and using a photodiode array (PDA) detector (UV detection between 190 and 500 nm). Elution was performed with a mobile phase flow rate of 0.5 mL/min consisting of a mixture of ultrapure water containing 0.01% formic acid (A) and methanol (B). The program starts at t = 0, ratio (A/B) 80:20; at t = 0.5 min, 80:20; at t = 5 min, 40:60; at t = 6 min, 10:90; at t = 7 min, 10:90; at t = 7.5 min, 80:20; and at t = 10 min, 80:20. 1 μL of the sample was injected into a Kinetex Biphenyl column (2.1 × 100 mm; 1.7 μm) (Phenomenex, Torrance, California, USA) heated to 55 °C. Mass spectra were acquired in the MSE mode including a low-energy function (CE 6 eV) as well as a second high-energy function (CE 25 to 50 eV) for both positive and negative mode ionizations to obtain information on fragmentation. Tandem MS (MS/MS) experiments were also carried out, and argon was used as collision gas, and the collision energy value was optimized to reach a relative intensity between 10 and 20% for each selected precursor ion. Parameters were adapted from the previous method as described by Tchoumtchoua et al. (75) The spectra obtained were processed using software UNIFI (version 1.9.2, Waters).

Nuclear Magnetic Resonance

Each sample, after evaporation, was solubilized in 650 μL of deuterated methanol and transferred to 5 mm 509-Up NMR tubes (Eurisotop, Cambridge Isotope Laboratories, Cambridge, UK). The one-dimensional (1D) (1H and 13C DEPTQ) and two-dimensional (2D) [1H J-resolved (JRES), correlated spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), and heteronuclear multiple bond coherence (HMBC)] NMR spectra were recorded using a BRUKER AVANCE III 600 MHz instrument (Bruker, Billerica, Massachusetts, USA) equipped with a probe (BBFO 5 mm tube) and an automatic tube changer. For the classical 1D proton, a 90° flip angle was performed, and the spectra were acquired using eight scans of 128 K data points with a spectral window of 14.02 ppm. The 2D 1H JRES NMR spectra were acquired using four scans per 64 increments which were collected in 64 K data points, with a spectral window of 14.02 ppm for F2 and 0.08 ppm for F1. The 1D DEPTQ spectra were acquired using 3 K scans using spectral widths of 251 ppm. The 2D COSY spectra were acquired using two scans per 512 increments collected at 4 K data points, with a spectral window of 14 ppm for F2 and 14 ppm for F1. The 2D HSQC spectra were acquired using 16 scans per 512 increments which were collected in 2 K data points, using a spectral window of 14 ppm for F2 and 200 ppm for F1. The 2D HMBC spectra were acquired using 16 scans per 512 increments which were collected in 2 K data points, using a spectral window of 14 ppm for F2 and 250 ppm for F1. All spectra were processed using Topspin software (version 3.5pl6, Bruker).

MIC Evaluation

Compounds 1 and 2 that showed an antibacterial potential were then evaluated for MICs on MSSA, MRSA, and S. caprae. Indeed, the MIC is the minimum concentration at which the compound inhibits bacterial growth. The method of dilution in the liquid medium was thus carried out, for which the bacterial suspensions were prepared in the same way as for the agar overlay bioautography method. The compounds were first solubilized in dimethylsulfoxide to a concentration of 2 mg/mL. Subsequently, dilutions were made in the MH medium to have 10 solutions with concentrations of 256, 128, 64, 32, 16, 8, 4, 2, 1, and 0.5 μg/mL. Microplates of 96 wells were used; 100 μL of the bacterial suspension and 100 μL of diluted solutions were added in wells 1–10 (the most concentrated solution in well 1 and the least concentrated solution in well 10), and well 11 represents the control of sterility of the medium, so 200 μL of MH was added to it, and well 12 represents the control of culture of the bacteria. The plate was then incubated at 37 °C for 24 h. After incubation, the lowest concentration for which no turbidity is observed corresponds to the MIC.

Fractional Inhibitory Concentration Index

Antimicrobial checkerboard assays were performed using the bacterial strains MSSA, MRSA, and S. caprae to determine the synergistic effects of the isolated compounds with the antibiotics cloxacillin and vancomycin. The compounds were evaluated using the concentration range of 2–128 μg/mL on all three bacteria; the concentration range of cloxacillin was from 3.75 × 10–3 to 0.25 μg/mL on MSSA and S. caprae and from 6.25 × 10–2 to 4 μg/mL on MRSA; the concentration range of vancomycin was from 3.12 × 10–2 to 2 μg/mL on all three bacteria. The effect of the combination of compounds and antibiotics was evaluated by calculating the fractional inhibitory concentration index (FICI) according to the following formula
“Synergy” effects were defined when the FICI was less than or equal to 0.5. “Additive” effects were defined when the FICI was greater than 0.5 and less than or equal to 1. An “indifference” effect was defined when the FICI was greater than 1 and less than or equal to 2.0. Antagonistic effects were observed when the FICI was greater than 2.0.

Results

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Phytochemical and Antibacterial Screening

After drying and grinding the leaves of T. bergeri, the compounds were extracted with a Soxhlet apparatus using solvents of increasing polarity leading to four fractions F1–F4 (see Extraction in the Experimental Section). The agar overlay bioautography method was used to verify the antibacterial properties of T. bergeri plant extracts. Biological evaluations were performed with a concentration of 100 mg/mL of T. bergeri fractions F1, F2, F3, and F4 on 12 bacterial strains including reference and clinical strains. This first screening showed antibacterial activity of the hexanic and dichloromethane fractions (namely, F1 and F2) on methicillin-sensitive S. aureus ATCC 29213 (MSSA) and methicillin-resistant S. aureus N-SARM-1 (MRSA) and antibacterial activity of F2 on S. caprae ATCC 35538 (S. caprae). However, the T. bergeri fractions did not show any bacterial activity against the Gram-negative bacteria studied in this report and against the other Gram-positive bacteria mentioned in the Experimental Section (see Table S1 in the Supporting Information). Therefore, we first focused on the F2 fraction in order to isolate the compounds responsible for the antibacterial activity against MSSA, MRSA, and S. caprae bacteria. For this purpose, the compounds present in the F2 fraction were separated by TLC using a chloroform/methanol (90/10) solvent system. After the development of the TLC plates, the biological evaluation was carried out this time only on MSSA, MRSA, and S. caprae bacteria. The results showed the inhibition zone of MSSA, MRSA, and S. caprae bacteria at the level of the subfractions noted F2.2, F2.3, F2.4, and F2.5 (Figure S2 in the Supporting Information). Based on these results, a bio-guided fractionation was performed. Indeed, the subfractions were isolated from F2 by preparative TLC, and new agar overlay bioautographies against MSSA, MRSA, and S. caprae bacteria were performed by depositing only the above-mentioned subfractions on TLC plates. The results showed that only the subfractions F2.3 and F2.5 have an antibacterial activity against these three bacteria, and they comprise two distinct compounds named compounds 1 and 2, respectively. A chemical derivatization on TLC plates was therefore performed in order to know the chemical family of these two compounds using specific visualizing reagents (Figure 1). Indeed in TLC, chemical derivatization is used to detect colorless compounds that cannot be visualized by UV light or fluorescence. Most often universal or polyvalent reagents such as vanillin sulfuric acid or p-anisaldehyde sulfuric acid are used to locate most classes of organic compounds. However, selective reagents can be used as derivatization agents such as Neu’s reagent (2-aminoethyldiphenylboric acid + PEG) for the identification of polyphenols. Derivatization showed a positive reaction of compound 1 (Rf = 0.56) and compound 2 (Rf = 0.41) with Neu’s reagent, suggesting the presence of polyphenols.

Figure 1

Figure 1. TLC plates of the four fractions obtained from T. bergeri. Mobile phase: chloroform/methanol (90/10). (A) UV 254 nm. (B) UV 365 nm. (C) Sulfuric vanillin. (D) Neu’s reagent. (E) Anisaldehyde. 1 and 2 represent compounds 1 and 2, respectively.

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Identification of Antibacterial Compounds

The F2.3 and F2.5 subfractions were analyzed by HPLC-UV for their chromatographic profiles (Figure S3); then, they were subsequently repurified by preparative HPLC to remove small impurities that were present, and the purity of the compounds was controlled by HPLC-UV. The compounds 1 and 2 obtained were then identified by HRMS and NMR.
In order to have preliminary information on the identity of the compounds, low-energy MSE and MS/MS spectra were acquired in positive and negative modes (Figures 2 and 3). Compound 1 with a retention time of 6.12 min has an [M + H]+ ion with m/z = 345.0973 and an [M – H]− ion with m/z = 343.0819; the exact masses were used to generate the crude formula C18H16O7. Regarding compound 2, it has a retention time of 5.74 min and has an [M + H]+ ion with m/z = 331.0820 and an [M – H]− ion with m/z = 329.0657; these exact masses generated the crude formula C17H14O7 (Table 1).

Figure 2

Figure 2. MSE (high-energy) and MS/MS spectra of compound 1 isolated from the dichloromethane fraction (F2) of T. bergeri. (A) MSE mass spectrum obtained in the negative mode. (B) MSE mass spectrum obtained in the positive mode. (C) MS/MS spectrum in the negative mode with a collision energy of 18 eV. (D) MS/MS spectrum in the positive mode with a collision energy of 28 eV.

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Figure 3

Figure 3. MSE (high-energy) and MS/MS spectra of compound 2 isolated from the dichloromethane fraction (F2) of T. bergeri. (A) MSE mass spectrum obtained in the negative mode. (B) MSE mass spectrum obtained in the positive mode. (C) MS/MS mass spectrum in the negative mode with a collision energy of 18 eV. (D) MS/MS mass spectrum in the positive mode with a collision energy of 28 eV.

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Table 1. UPLC–HRMS Data of Compounds 1 and 2
#compound nameRT (minutes)[M + H]+, m/z[M – H]−, m/zmolecular massmolecular formula
1penduletin6.12345.0973343.0819344C18H16O7
2viscosine5.74a331.0820329.0657330C17H14O7
After obtaining the masses and the elemental compositions of the compounds, the NMR data allow a more complete identification. For compound 1, 6 proton signals and 18 carbon signals were observed in the 1D 1H and 13C DEPTQ NMR spectra, respectively (Table 2). The three singlets at 3.78 ppm (s, 3H), 3.83 ppm (s, 3H), and 3.96 ppm (s, 3H), correlated in HSQC to the carbons at 60.7, 61.3, and 57.1 ppm, respectively, indicate the presence of three methoxylated groups. In HMBC, these methoxylated groups are related to carbons C-3 (139.4 ppm), C-6 (133.5 ppm), and C-7 (160.5 ppm). The singlet at 6.76 ppm (s, 1H) is connected in HSQC with the C-8 carbon at 92.1 ppm. HMBC correlations between this proton and carbons C-6 (133.5 ppm), C-7 (160.5 ppm), C-9 (154.1 ppm), C-10 (107.1 ppm), and C-4 (180.4 ppm) show the presence of two aromatic rings constituting rings A and C. The proton signals at 8.02 ppm (d, 2H, 8.77 Hz) and 6.95 ppm (d, 2H, 8.77 Hz) indicate the presence of four aromatic protons which are H-2′/6′ and H-3′/5′, respectively. The 2D COSY spectrum and the coupling constants show that these protons are ortho correlated. The HMBC correlations between the H-3′/5′ protons with the C-1′ carbon (122.5 ppm) and the H-2′/6′ protons with the C-2 carbon (158.6 ppm) show that the B ring is attached to the C ring in position 2. These chemical shifts and correlations are consistent with those in the literature and identify this compound 1 as 5,4′-dihydroxy-3,6,7-trimethoxyflavone, also called penduletin (Figure 4A).

Figure 4

Figure 4. Chemical structures of (A) penduletin (compound 1) and (B) viscosine (compound 2).

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Table 2. NMR Data of Compounds 1 and 2
 12
C/HδH (ppm)J (Hz)DEPTδC (ppm)δH (ppm)J (Hz)DEPTδC (ppm)
2  C158.6  C158.1
3  C139.4  C138.9
4  C180.4  C180.0
5  C   C 
6  C133.5  C132.7
7  C160.5  C159.0
86.76, s CH92.16.52, s CH95.0
9  C154.1  C153.7
10  C107.1  C106.3
1′  C122.5  C122.4
2′8.02, d8.7CH131.57.98, d8.3CH131.4
3′6.95, d8.7CH116.76.94, d8.3CH116.6
4′  C161.7  C161.6
5′6.95, d8.7CH116.76.94, d8.3CH116.6
6′8.02, d8.7CH131.57.98, d8.3CH131.4
3-OMe3.78, s CH360.73.77, s CH360.5
6-OMe3.83, s CH361.33.87, s CH360.9
7-OMe3.96, s CH357.1    
For compound 2, NMR spectra were quite similar to those of compound 1 except that the NMR signals of a methoxy group were missing. Indeed, 5 proton signals and 17 carbon signals were observed in the 1D 1H and 13C DEPTQ spectra, respectively (Table 2). The singlet at 6.52 ppm (s, 1H) correlates in HSQC with C-8 (95.0 ppm) and in HMBC with carbons C-4 (180.0 ppm), C-6 (132.7 ppm), C-7 (159.0 ppm), C-9 (153.7 ppm), and C-10 (106.3 ppm), indicating the presence of both rings A and C. The two singlets at 3.77 ppm (s, 3H) and 3.87 ppm (s, 3H), respectively, correlated in HSQC to the carbons at 60.5 and 60.9 ppm, indicate the presence of two methoxylated groups.
These are linked in HMBC to the C-3 (138.9 ppm) and C-6 (132.7 ppm) carbons, respectively. The protons H-2′/6′ at 7.98 ppm (d, 2H, 8.3 Hz) and H-3′/5′ at 6.94 ppm (d, 2H, 8.3 Hz) are ortho-coupled and are linked in HSQC to the carbons C-2′/6′ (131.4 ppm) and C-3′/5′ (116.7 ppm), respectively. The HMBC correlations of the H-2′/6′ protons at carbon C-2 (158.1 ppm) and H-3′/5′ at carbon C-1′ (122.4 ppm) show that ring B is attached to ring C at position 2. All this information allows us to identify compound 2 as 4′,5,7-trihydroxy-3,6-dimethoxyflavone, also called viscosine (Figure 4B). The identification of these two compounds was also confirmed by analysis of the standards which showed similar retention times and the same behaviors toward fragmentation by MS/MS or high-energy MSE with identical fragment intensities (see MSE and MS/MS mass spectra in Supporting Information, Figures S4, S5, S6, and S7).

Evaluation of Antibacterial Activity

Having demonstrated the growth inhibition of MSSA, MRSA, and S. caprae bacteria using agar overlay bioautography, the MICs of compounds 1 and 2 were determined using the broth microdilution method. The results obtained show a MIC value greater than 256 μg/mL for penduletin against the three bacterial strains. For viscosine, the MIC value is equal to 128 μg/mL against MSSA and is equal to 256 μg/mL against MRSA and S. caprae (Table 3). These MIC values were high compared to those of the antibiotics, so the compounds were combined with vancomycin and cloxacillin to investigate their synergistic antibacterial effects. The results obtained show that when the compounds were combined with antibiotics, they were able to reduce the MIC values of the latter. With FICI values between 0.5 and 1, viscosine showed additive effects when combined with both antibiotics against all three bacterial strains. However, it is interesting to note that penduletin showed synergistic effects with vancomycin against MSSA and S. caprae strains with FICI values inferior to 0.258 and 0.5, respectively.
Table 3. Antibacterial Activities of Compounds 1 and 2
  MIC (μg/mL)  
strainsagentsalonecombinationFICFICI
methicillin-sensitive Staphylococcus aureus ATCC 29213 (MSSA)penduletin (1)>2562<0.008<0.258
 vancomycin10.250.25 
 penduletin (1)>25664<0.25<0.75
 cloxacillin0.250.1250.5 
 viscosine (2)128320.250.75
 vancomycin10.50.5 
 viscosine (2)12840.03120.531
 cloxacillin0.250.1250.5 
methicillin-resistant Staphylococcus aureus N-SARM-1 (MRSA)penduletin (1)>25664<0.25<0.75
 vancomycin10.50.5 
 penduletin (1)>2568<0.0312<0.531
 cloxacillin420.5 
 viscosine (2)256640.250.75
 vancomycin10.50.5 
 viscosine (2)256160.06250.562
 cloxacillin420.5 
Staphylococcus caprae ATCC 35538 (S. caprae)penduletin (1)>25664<0.25<0.5
 vancomycin10.250.25 
 penduletin (1)>2564<0.016<0.516
 cloxacillin0.250.1250.5 
 viscosine (2)256640.250.75
 vancomycin10.50.5 
 viscosine (2)25680.03120.531
 cloxacillin0.250.1250.5 

Discussion

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Plants produce secondary metabolites with interesting biological properties, particularly antibacterial properties, which gives them an important place in the search for new drugs. For this reason, research studies ranging from ethnobotanical and ethnopharmacological studies of plants to the isolation and optimization of key plant compounds are common. They represent an important part of the research for new antibacterial compounds motivated by the need to solve the problem of bacterial resistance to antibiotics. Being used for a long time in the American continent as medicinal plants, the species of the genus Tillandsia have aroused the interest of researchers who have studied the biological properties of their constituents. These studies have demonstrated the presence of compounds with antiangiogenic, (31) antiviral, (32) antitumor, (33) hypoglycemic, (34) and anticancer (35−39) activities. Regarding antibacterial activity, it was reported in 1945 that the crude extract of T. usneoides is effective against Gram-positive bacteria. (40) This was later confirmed by the isolation of a glycosylated flavonol with antibacterial activity against S. aureus. (41) Subsequently, in 1995, aqueous extracts of T. recurvata, T. aeranthos, and T. usneoides showed antimicrobial activity against E. coli, S. aureus, P. aeruginosa, B. subtilis, and Micrococcus luteus. Furthermore, in the same study, the aqueous extracts of T. aeranthos and T. recurvata showed strong activity against P. aeruginosa which is a Gram-negative bacterium. This is an interesting fact as Gram-negative bacteria are generally more resistant than Gram-positive bacteria. (42) Indeed, the problems of bacterial resistance and the spread of resistance are currently more related to Gram-negative bacteria such as P. aeruginosa and enterobacteria. More recently in 2017, a study was conducted by Faller and his team to explore the antibacterial efficacy of T. usneoides against skin infections in wound healing. The results showed a high inhibition of the growth of S. aureus, P. aeruginosa, and Staphylococcus epidermis bacteria by methanolic and ethanolic extracts of T. usneoides. (43) For all these studies, the alcoholic or aqueous extracts are responsible for the antibacterial activity. In our study, the methanolic and methanol/water extracts did not show any inhibition of the different bacteria used. This could be explained by a low selectivity of the compounds present in these extracts against the bacteria chosen for this study, by a very low concentration of the active compounds in these extracts, or by a disruption of the synergy between the active compounds caused by TLC.
The studies mentioned just above confirm the usefulness of Tillandsia species as sources of antibacterial agents; however, none of these studies have carried out the structural identification of the compounds responsible for the antibacterial activity within the different species studied. Moreover, no study has focused on the antibacterial properties of T. bergeri species. Our present study is the first to perform the structural identification of antibacterial compounds from T. bergeri extracts. In order to identify antibacterial compounds, agar overlay bioautography was used as a screening method. It is a very popular screening method because of its facility of realization, low cost, time saving, and ability to perform simultaneously the biological evaluation of a large number of samples. (44) This bioautographic method is very suitable for broad spectrum microorganisms such as yeasts and bacteria. (45) It guided us to the isolation and identification of two compounds belonging to the flavonoid family. This identification was performed using NMR and HRMS. These two characterization techniques, which are both very efficient, can only reveal their full efficiency when they are skillfully combined. This complementarity allows one to solve most of the structural elucidation cases encountered. With HRMS, the crude formulas and fragments of the different compounds helped us obtain information about structures of the molecules. Also, thanks to NMR, the results obtained in HRMS could be confirmed while establishing a precise structural characterization.
Penduletin is the first compound identified from the dichloromethane extract of T. bergeri. It was first isolated in 1958, in the glucosylated form, from the ethanolic extract of the species Brickellia pendula obtained in Contreras near Mexico City. (46)B. pendula is thus native to Mexico and belongs to the Asteraceae family. (47) Later, penduletin was isolated from several other species including Cleome amblyocarpa, Cleome brachycharpa, Cleome chrysantha, (48)Rabdosia rubescens, (49)Tanacetum artemisioides, (50)Sideritis caesarea, (51)Digitalis thapsi, (52)Artemisia annua, (53) and Dodonaea viscosa. (54) A derivative of penduletin, penduletin-4′-O-methylether was isolated from the methanolic extract of Tillandsia pupurea. (55) Penduletin is a flavone in the form of an amorphous yellow powder with anti-inflammatory and cytotoxicity activities, (49) butyrylcholinesterase inhibitor activity, (51,54) antioxidant properties, (56) and strong in vitro activity against enterovirus 71 (EV71) with low cytotoxicity. Regarding antibacterial properties, penduletin showed weak antibacterial activity (32–64 μg/mL) against Neisseria gonorrhoeae which is a Gram-negative bacterium responsible for gonococcal disease (57) as well as low antibacterial activity against S. aureus with a MIC value >128 μg/mL. (58) It has also been recently considered as inactive against S. aureus, Bacillus cereus, S. enteritidis, and C. albicans. (59) These results correlate with our results for the MIC value of penduletin on MSSA.
The second compound identified from the dichloromethane extract of T. bergeri is viscosine. It is a flavone that has been isolated many times from the medicinal plant D. viscosa which belongs to the Sapindaceae family. (60−63) It has also been isolated from the flowers of Centaurea jacea (64) and from a strain of actinobacteria derived from marine sediments. (65) It is a compound that has demonstrated a significant inhibitory effect on lipoxygenase. (66) It has antioxidant, anticholinergic, and antiepileptic properties. (67) Viscosine has also shown significant activity against a human colon carcinoma cell line and a hepatocellular carcinoma cell line. (65) As for penduletin, viscosine was also studied for its antibacterial properties. Indeed, the study carried out by Teffo et al. showed a moderate antibacterial activity of viscosine against Gram-positive bacteria S. aureus and E. faecalis with respective MIC values of 125 and 32 μg/mL and against Gram-negative bacteria E. coli and P. aeruginosa with respective MIC values of 26 and 32 μg/mL. (62) However, a more recent study showed no inhibition of P. aeruginosa by viscosine but a moderate activity of the latter against Gram-positive bacteria S. aureus and B. cereus. (65) In our study, penduletin and viscosine showed moderate antibacterial activity against MSSA, MRSA, and S. caprae, and no inhibition of Gram-negative bacteria was observed by the crude extract containing these two compounds. The contradictory results sometimes observed on the antibacterial activity of flavonoids can be attributed to the methods used to evaluate the antibacterial activity which are different from one study to another. These inconsistencies can also be attributed to variations in each antibacterial evaluation method including differences in the amount of the bacterial strain, differences in the types or volumes of the broth and agar, or differences in the incubation period. Another factor is related to the problem of solubilization of flavonoids in organic solvents, leading to precipitation of the latter which can affect the biological evaluation by decreasing the contact between the bacterial cells and the flavonoid molecules and lead to false negative reports of the antibacterial activity. (68)
Since both antibacterial compounds isolated from the dichloromethane extract of T. bergeri are flavonoids, the mechanism of action of flavonoids is mainly based on the disruption of the bacterial plasma membrane which can trigger a multitude of effects such as pore formation, leakage, polarity modification, increase in permeability, fluidity modification, delocalization of membrane proteins, and other phenomena responsible for the antibacterial activity. Although little information is available on the structure–function relationship of antibacterial flavonoids, conjugation with sugar moieties at certain positions of the aromatic ring could increase the antibacterial activity of these compounds. (69) Flavonoids are also inhibitors of bacterial efflux pumps. (70)
Although phytochemicals generally have higher MIC values than traditional antibiotics, they may have different mechanisms and target sites compared to those of antibiotics. For this reason, their combination with conventional antibiotics has been proposed to provide superior efficacy in suppressing resistance development. This was observed in our study with higher MIC values of penduletin and viscosine than those of vancomycin and cloxacillin. These compounds were therefore combined with these antibiotics to increase the antibacterial activity of the latter. The results of their combinations showed not only a decrease in MICs of the antibiotics but also a synergistic effect of penduletin when combined with vancomycin against MSSA and S. caprae bacteria. Indeed, synergistic effects between various flavonoids and antibacterial agents are known, (68,71−74) and a study on the synergistic antibacterial effects of flavonoids from A. rupestris against S. aureus had shown a synergistic effect of penduletin when combined with norfloxacin, NorA efflux pump being affected. (58)

Conclusions

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Bio-guided fractionation of T. bergeri extracts using agar overlay bioautography as a screening method allowed us to demonstrate the inhibition of Gram-positive MSSA, MRSA, and S. caprae bacteria by a dichloromethane fraction. The phytochemical investigation of this fraction led to the isolation and identification of two flavones: penduletin and viscosine. These two compounds were isolated for the first time from T. bergeri species. The combination of these compounds with vancomycin and cloxacillin showed not only a decrease in MICs of the antibiotics but also a synergistic effect of penduletin when combined with vancomycin against MSSA and S. caprae bacteria.

Supporting Information

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The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsomega.2c04195.

  • Photograph of a T. bergeri individual; results of antibacterial screening of hexanic and dichloromethane fractions of T. bergeri methanol and methanol/water fractions of T. bergeri against a panel of Gram-positive and Gram-negative pathogens; TLC agar overlay bioautography of the dichloromethane fraction against MSSA, MRSA, and S. caprae; HPLC chromatograms of subfractions A F2.3 and B F2.5; MSE mass spectra of compound 1 isolated from the dichloromethane fraction of T. bergeri and those of the standard of penduletin; MSE mass spectra of compound 2 isolated from the dichloromethane fraction of T. bergeri and those of the standard of viscosine; MS/MS spectra of compound 1 isolated from the dichloromethane fraction of T. bergeri and those of the standard of penduletin; and MS/MS spectra of compound 2 isolated from the dichloromethane fraction of T. bergeri and those of the standard of viscosine (PDF)

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Author Information

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  • Corresponding Author
  • Authors
    • Mame-Marietou Lo - UNIV. NIMES, UPR CHROME, 5 rue du Dr Georges Salan, F-30021 Nîmes Cedex 1, France
    • Zohra Benfodda - UNIV. NIMES, UPR CHROME, 5 rue du Dr Georges Salan, F-30021 Nîmes Cedex 1, France;  Orcidhttps://orcid.org/0000-0001-7574-4977
    • Catherine Dunyach-Rémy - Institut National de la Santé et de la Recherche Médicale, U1047, Montpellier University, CHU de Nîmes, Place du Pr R. Debré, 30029 Nîmes, France
    • David Bénimélis - UNIV. NIMES, UPR CHROME, 5 rue du Dr Georges Salan, F-30021 Nîmes Cedex 1, France
    • Romain Roulard - UMR 1158 Transfontalière BioEcoAgro, BIOlogie des Plantes et Innovation (BIOPI), UPJV, Faculté de Pharmacie, 1 rue des Louvels, 80025 Amiens CEDEX, France
    • Jean-Xavier Fontaine - UMR 1158 Transfontalière BioEcoAgro, BIOlogie des Plantes et Innovation (BIOPI), UPJV, Faculté de Pharmacie, 1 rue des Louvels, 80025 Amiens CEDEX, France
    • David Mathiron - Plateforme-Analytique, Université de Picardie Jules Verne, 33 rue Saint Leu, 80039 Amiens, France
    • Anthony Quéro - UMR 1158 Transfontalière BioEcoAgro, BIOlogie des Plantes et Innovation (BIOPI), UPJV, Faculté de Pharmacie, 1 rue des Louvels, 80025 Amiens CEDEX, France
    • Roland Molinié - UMR 1158 Transfontalière BioEcoAgro, BIOlogie des Plantes et Innovation (BIOPI), UPJV, Faculté de Pharmacie, 1 rue des Louvels, 80025 Amiens CEDEX, France
  • Author Contributions

    The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript.

  • Notes
    The authors declare no competing financial interest.

Acknowledgments

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This work was financially supported by LA REGION OCCITANIE and UNIV. NIMES. We gratefully acknowledge the Tillandsia PROD (28 chemin du Cailar, 30740 Le Cailar, France, https://www.tillandsia-prod.com/) plant nursery (Pierre Kerrand, Daniel Thomin and Julien Vigo) for providing us the Tillandsia plants used in this study, for helpful discussions, and for their interest in the project.

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    Aguilar-Rodríguez, P. A.; MacSwiney, G.; García-Franco, T.; Knauer, J. G.; Kessler, A.; Kessler, M. First Record of Bat-Pollination in the Species-Rich Genus Tillandsia (Bromeliaceae). Ann. Bot. 2014, 113, 1047– 1055,  DOI: 10.1093/aob/mcu031
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    First record of bat-pollination in the species-rich genus Tillandsia (Bromeliaceae)
    Aguilar-Rodriguez Pedro Adrian; MacSwiney G M Cristina; Kromer Thorsten; Garcia-Franco Jose G; Knauer Anina; Kessler Michael
    Annals of botany (2014), 113 (6), 1047-55 ISSN:.
    BACKGROUND AND AIMS: Bromeliaceae is a species-rich neotropical plant family that uses a variety of pollinators, principally vertebrates. Tillandsia is the most diverse genus, and includes more than one-third of all bromeliad species. Within this genus, the majority of species rely on diurnal pollination by hummingbirds; however, the flowers of some Tillandsia species show some characteristics typical for pollination by nocturnal animals, particularly bats and moths. In this study an examination is made of the floral and reproductive biology of the epiphytic bromeliad Tillandsia macropetala in a fragment of humid montane forest in central Veracruz, Mexico. METHODS: The reproductive system of the species, duration of anthesis, production of nectar and floral scent, as well as diurnal and nocturnal floral visitors and their effectiveness in pollination were determined. KEY RESULTS: Tillandsia macropetala is a self-compatible species that achieves a higher fruit production through outcrossing. Nectar production is restricted to the night, and only nocturnal visits result in the development of fruits. The most frequent visitor (75 % of visits) and the only pollinator of this bromeliad (in 96 % of visits) was the nectarivorous bat Anoura geoffroyi (Phyllostomidae: Glossophaginae). CONCLUSIONS: This is the first report of chiropterophily within the genus Tillandsia. The results on the pollination biology of this bromeliad suggest an ongoing evolutionary switch from pollination by birds or moths to bats.
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    Manetti, Liliana Maria; Delaporte, Rosemeres Horwat; Laverde, Antonio, Jr.
    Quimica Nova (2009), 32 (7), 1885-1897CODEN: QUNODK; ISSN:0100-4042. (Sociedade Brasileira de Quimica)
    This review describes aspects of the Bromeliaceae family dealing the traditional applications, biol. activities and distribution of secondary metabolites in distinct subfamilies. Some species are used with medicinal purposed in the treatment of respiratory, diabetes or inflammation diseases, and gastrointestinal disorders. Special emphasis on cycloartane triterpenoids and flavonoids, typical metabolites of this family, are presented. Bromeliaceae is unique amongst the monocotyledons in the frequency and variety of flavonoids with hydroxylation or methoxylation at the 6-position. Other compd. classes as steroids, hidroxycinnamic acids, phenylpropane diglycerides, lignans, are presented.
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    Estrella-Parra, E.; Flores-Cruz, M.; Blancas-Flores, G.; Koch, S. D.; Alarcón-Aguilar, F. J. The Tillandsia Genus: History, Uses, Chemistry, and Biological Activ. Bol. Latinoam. Caribe Plant. Med. Aromat. 2019, 18, 239– 264
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    The Tillandsia genus: history, uses, chemistry, and biological activity
    Estrella-Parra, Edgar; Flores-Cruz, Maria; Blancas-Flores, Gerardo; Koch, Stephen D.; Alarcon-Aguilar, Francisco J.
    Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromaticas (2019), 18 (3), 239-264CODEN: BLCPBA; ISSN:0717-7917. (Sociedad Latinoamericana de Fitoquimica)
    Tillandsia L. genus comprises 649 species, with different uses at different times. T. usneoides L. uses are reported since the late-archaic and pre-Columbian cultures. In XIX-XX centuries, T. usneoides was used in some manufd. products, as polish and packing fruit. Tillandsia has a favorable reputation as medicine: for leucorrhea, rheumatism, ulcers, hemorrhoid treatment, as an anti-diabetic remedy, emetic, analgesic, purgative, contraceptive, antispasmodic and diuretic. Tillandsia chem. compn. includes cycloartane triterpenes and hydroxy-flavonoids, which are present in at least 24 species. Several exts. and compds. from Tillandsia spp. have been reported with pharmacol. actions, as anti-neoplasia, hypolipidemic, antifungal, anti-HSV-1, hypoglycemic and microbicide. This review communicates the economic importance, ethnobotany, chem. compn. and biol. activities of the Tillandsia genus, and analyze its biol. and economic perspective. Tillandsia genus has cultural, economic and pharmacol. relevance, with a high potential in many essential aspects of the modern society.
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    Choma, I. M.; Grzelak, E. M. Bioautography Detection in Thin-Layer Chromatography. J. Chromatogr. A 2011, 1218, 2684– 2691,  DOI: 10.1016/j.chroma.2010.12.069
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    Bioautography detection in thin-layer chromatography
    Choma, Irena M.; Grzelak, Edyta M.
    Journal of Chromatography A (2011), 1218 (19), 2684-2691CODEN: JCRAEY; ISSN:0021-9673. (Elsevier B.V.)
    A review. Bioautog. is a microbial detection method hyphenated with planar chromatog. techniques. It is based mainly on antimicrobial or antifungal properties of analyzed substances. The review discusses three versions of bioautog., i.e. contact, immersion and direct bioautog. The more concern is given to the last one. Many applications are quoted, not only for testing various groups of compds., but also for investigating biochem. processes and factors influencing bacterial growth. Addnl., related methods, which can be included into direct bioautog., are discussed. The most promising among them seems to be TLC-bioluminescence screening.
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    GOODALL R R; LEVI A A
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    Jesionek, W.; Majer-Dziedzic, B.; Choma, I. M. Separation, Identification, and Investigation of Antioxidant Ability of Plant Extract Components Using TLC, LC-MS, and TLC-DPPH. J. Liq. Chromatogr. Relat. Technol. 2015, 38, 1147– 1153,  DOI: 10.1080/10826076.2015.1028295
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    Separation, Identification, and Investigation of Antioxidant Ability of Plant Extract Components Using TLC, LC-MS, and TLC-DPPH•
    Jesionek, Wioleta; Majer-Dziedzic, Barbara; Choma, Irena Maria
    Journal of Liquid Chromatography & Related Technologies (2015), 38 (11), 1147-1153CODEN: JLCTFC; ISSN:1082-6076. (Taylor & Francis, Inc.)
    Ten common phenolic compds. from the exts. of five plant species, i.e., Hypericum perforatum L., Matricaria recutita L., Achillea millefolium L., Thymus vulgaris L., and Salvia officinalis L., were sepd. using optimized thin-layer chromatog. (TLC) conditions at normal phase mode and were visualized using Natural Product/Polyethylene Glycol Reagent. Antioxidant properties of components of the exts. were assessed using TLC-DPPH• directly on the TLC plate. Nine out of ten analyzed polyphenols were proved to be radical scavengers. The presence and identity of target substances in plant samples were confirmed by the liq. chromatog.-mass spectrometry technique.
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    Choma, I.; Jesionek, W. TLC-Direct Bioautography as a High Throughput Method for Detection of Antimicrobials in Plants. Chromatography 2015, 2, 225– 238,  DOI: 10.3390/chromatography2020225
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    TLC-direct bioautography as a high throughput method for detection of antimicrobials in plants
    Choma, Irena M.; Jesionek, Wioleta
    Chromatography (2015), 2 (2), 225-238CODEN: CHROBV; ISSN:2227-9075. (MDPI AG)
    The richness of bioactive compds. in plant materials encourages continuous development of sepn. methods and bioassays for their isolation and identification. Thin-layer chromatog.-direct bioautog. links sepn. on the adsorbent layer with biol. tests performed directly on it. Therefore, the method is very convenient for searching plant constituents with biol. activity, such as antibiotics. Test bacteria grow directly on a plate surface excluding places where antibacterials are located. They can be detected with reagents converted by living bacteria. TLC-DB is a high throughput method enabling analyses of many samples in parallel and the comparison of their activity. Both screening and semi-quant. anal. is possible. The targeted compds. can be identified using spectroscopic methods, mostly mass spectrometry, that can be performed directly on a TLC plate. This paper discusses all above mentioned aspects of TLC-DB, illustrating them with literature, schemes and our own results.
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    Dewanjee, S.; Gangopadhyay, M.; Bhattacharya, N.; Khanra, R.; Dua, T. K. Bioautography and Its Scope in the Field of Natural Product Chemistry. J. Pharm. Anal. 2015, 5, 75– 84,  DOI: 10.1016/j.jpha.2014.06.002
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    Bioautography and its scope in the field of natural product chemistry
    Dewanjee Saikat; Bhattacharya Niloy; Khanra Ritu; Dua Tarun K; Gangopadhyay Moumita
    Journal of pharmaceutical analysis (2015), 5 (2), 75-84 ISSN:2095-1779.
    Medicinal plants, vegetables and fruits are the sources of huge number of bioactive lead/scaffolds with therapeutic and nutraceutical importance. Bioautography is a means of target-directed isolation of active molecules on chromatogram. Organic solvents employed in chromatographic separation process can be completely removed before biological detection because these solvents cause inactivation of enzymes and/or death of living organisms. They offer a rapid and easy identification of bioactive lead/scaffolds in complex matrices of plant extracts. Bioautography is a technique to isolate hit(s)/lead(s) by employing a suitable chromatographic process followed by a biological detection system. This review critically describes the methodologies to identify antimicrobial, antioxidant, enzyme inhibitor lead/scaffolds by employing bioautography. A significant number of examples have been incorporated to authenticate the methodologies.
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    Choma, I.; Jesionek, W. Effects-Directed Biological Detection. In Instrumental Thin-Layer Chromatography; Poole, C. F., Ed.; Elsevier: Detroit, MI, USA, 2015; pp 279– 312.
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    Rahalison, L.; Hamburger, M.; Hostettmann, K.; Monod, M.; Frenk, E. A Bioautographic Agar Overlay Method for the Detection of Antifungal Compounds from Higher Plants. Phytochem. Anal. 1991, 2, 199– 203,  DOI: 10.1002/pca.2800020503
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    A bioautographic agar overlay method for the detection of antifungal compounds from higher plants
    Rahalison, L.; Hamburger, M.; Hostettmann, K.; Monod, M.; Frenk, E.
    Phytochemical Analysis (1991), 2 (5), 199-203CODEN: PHANEL; ISSN:0958-0344.
    A simple bioautog. agar overlay assay using Candida abicans as the indicator organism for the detection and activity-guided fractionation of antifungal compds. by thin layer chromatog. has been developed. Inhibition of fungal growth was assessed by the detection of dehydrogenase activity with thiazolyl blue (methylthiazolyltetrazolium chloride; MTT). A series of clin. used antimycotic agents were tested in order to det. the sensitivity of the assay. The compatibility of the agar overlay technique with chem. modified silica gel (Diol and RP-18) plates and with various org. solvents was evaluated. The methodol. is also applicable to the search for antibacterial compds., as shown with Bacillus subtilis as a test organism.
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    Nuthan, B. R.; Rakshith, D.; Marulasiddaswamy, K. M.; Rao, H. C. Y.; Ramesha, K. P.; Mohana, N. C.; Siddappa, S.; Darshan, D.; Kumara, K. K. S.; Satish, S. Application of Optimized and Validated Agar Overlay TLC-Bioautography Assay for Detecting the Antimicrobial Metabolites of Pharmaceutical Interest. J. Chromatogr. Sci. 2020, 58, 737– 746,  DOI: 10.1093/chromsci/bmaa045
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    Application of optimized and validated agar overlay TLC-bioautography assay for detecting the antimicrobial metabolites of pharmaceutical interest
    Nuthan, Bettadapura Rameshgowda; Rakshith, Devaraju; Marulasiddaswamy, Kuppuru Mallikarjunaiah; Rao, H. C. Yashavantha; Ramesha, Kolathur Puttamadaiah; Mohana, Nagabhushana Chandra; Siddappa, Shiva; Darshan, Doreraj; Kumara, Kigga Kaadappa Sampath; Satish, Sreedharamurthy
    Journal of Chromatographic Science (2020), 58 (8), 737-746CODEN: JCHSBZ; ISSN:1945-239X. (Oxford University Press)
    The agar overlay TLC-bioautog. is one of the crucial methods for simultaneous in situ detection and sepn. of antimicrobial metabolites of pharmaceutical interest. The main focus of this research relies on the dereplication of an antimicrobial metabolite coriloxin derived from mycoendophytic Xylaria sp. NBRTSB-20 with a validation of agar overlay TLC-bioautog. technique. This polyketide metabolite coriloxin was purified by column chromatog., and its purity was assessed by HPLC, UPLC-ESI-QTOF-MS, FT-IR and NMR spectral anal. The antimicrobial capability of Et acetate ext. and the purified compd. coriloxin was detd. by disk diffusion, minimal inhibitory concn. and agar overlay TLC-bioautog. assay. The visible LOD of coriloxin antimicrobial activity was found at 10μg for Escherichia coli and 20μg for both Staphylococcus aureus and Fusarium oxysporum. Inter- and intra-day precision was detd. as the relative std. deviation is less than 6.56%, which proved that this method was precise. The accuracy was expressed as recovery, and the values were found ranging from 91.18 to 108.73% with RSD values 0.94-2.30%, resp. The overall findings of this investigation suggest that agar overlay TLC-bioautog. assay is a suitable and acceptable method for the in situ detn. of antimicrobial pharmaceuticals.
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    Grela, E.; Kozłowska, J.; Grabowiecka, A. Current methodology of MTT assay in bacteria - A review. Acta Histochem. 2018, 120, 303– 311,  DOI: 10.1016/j.acthis.2018.03.007
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    Current methodology of MTT assay in bacteria - A review
    Grela, Ewa; Kozlowska, Joanna; Grabowiecka, Agnieszka
    Acta Histochemica (2018), 120 (4), 303-311CODEN: AHISA9; ISSN:0065-1281. (Elsevier GmbH)
    A review. The MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) tetrazolium assay is a popular tool in estg. the metabolic activity of living cells. The test is based on enzymic redn. of the lightly colored tetrazolium salt to its formazan of intense purple-blue color, which can be quantified spectrophotometrically. Under properly optimized conditions the obtained absorbance value is directly proportional to the no. of living cells. Originally, the MTT assay was devised for use in eukaryotic cells lines and later applied for bacteria and fungi. As the mechanism of MTT redn. was studied in detail mostly considering eukaryotic cells, the lack of information resulted in generating a vast variety of MTT based protocols for bacterial enzymic activity evaluation. In the presented article the main aspects of the MTT assay applicability in bacterial research were summarized, with special emphasis on sources of inaccuracies and misinterpretation of the test results.
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    Marston, A. Thin-Layer Chromatography with Biological Detection in Phytochemistry. J. Chromatogr. A 2011, 1218, 2676– 2683,  DOI: 10.1016/j.chroma.2010.12.068
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    Thin-layer chromatography with biological detection in phytochemistry
    Marston, A.
    Journal of Chromatography A (2011), 1218 (19), 2676-2683CODEN: JCRAEY; ISSN:0021-9673. (Elsevier B.V.)
    A review. Bioautog. on thin-layer chromatog. (TLC) plates is a means of detecting the biol. activity of a sample which has migrated on the plate with a suitable solvent. It only requires small amts. of sample and is ideal for the investigation of plant constituents, which often occur as complex mixts. It can be used for the target-directed isolation of these constituents. In contrast to HPLC, many samples can be run at the same time on TLC. Org. solvents, which cause inactivation of enzymes or death of living organisms, can be completely removed before biol. detection. Many bioassays are compatible with TLC. Antimicrobial, radical scavenging, antioxidant activities and enzyme inhibition feature among the tests that are employed.
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    Horváth, G.; Jámbor, N.; Végh, A.; Böszörményi, A.; Lemberkovics, É.; Héthelyi, É.; Kovács, K.; Kocsis, B. Antimicrobial Activity of Essential Oils: The Possibilities of TLC-Bioautography. Flavour Fragrance J. 2010, 25, 178– 182,  DOI: 10.1002/ffj.1993
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    Antimicrobial activity of essential oils: the possibilities of TLC-bioautography
    Horvath, Gyorgyi; Jambor, Noemi; Vegh, Anna; Boszormenyi, Andrea; Lemberkovics, Eva; Hethelyi, Eva; Kovacs, Krisztina; Kocsis, Bela
    Flavour and Fragrance Journal (2010), 25 (3), 178-182CODEN: FFJOED; ISSN:0882-5734. (John Wiley & Sons Ltd.)
    Essential oils are well-known for their antimicrobial activity against different plant and human pathogenic microorganisms. The results of the most commonly used antimicrobial assays are very different; sometimes their reliability is questionable, therefore standardized methods need to be used to solve this problem. The present study aims at the phytochem. characterization of some essential oils (thyme, lavender, eucalyptus, spearmint and cinnamon) that are important from the therapeutic and economic aspects and the optimized microbiol. investigation of the effect of essential oils on human and plant pathogenic microorganisms. The chem. compn. of the essential oils was analyzed with thin-layer chromatog. (TLC) and their compn. was controlled by gas chromatog. (GC). The antibacterial effect was investigated using the TLC-bioautog. method. The solvents applied in TLC developing systems were also tested. Our results showed that toluene, Et acetate, ethanol and chloroform as solvents used in the assay had no inhibiting effect on the test bacteria. The antibacterial activity of thyme, lavender and cinnamon oils and their main components (thymol, carvacrol, linalool, eugenol) was obsd. in the case of two plant pathogenic bacteria (Xanthomonas campestris pv. vesicatoria and Pseudomonas syringae pv. phaseolicola) and some human pathogens (Staphylococcus epidermidis, S. saprophyticus and two strains of S. aureus, including one methicillin-resistant strain). On the whole, the antibacterial activity of essential oils can be related to their most abundant components, but the effect of the minor components should also be taken into consideration. Direct bioautog. is more cost-effective and compares better with traditional microbiol. lab. methods (e.g. disk-diffusion, agar-plate technique).
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    Mühlebach, A.; Adam, J.; Schön, U. Streamlined Approach to High-Quality Purification and Identification of Compound Series Using High-Resolution MS and NMR. J. Sep. Sci. 2011, 34, 2983– 2988,  DOI: 10.1002/jssc.201100382
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    Streamlined approach to high-quality purification and identification of compound series using high-resolution MS and NMR
    Muehlebach, Anneke; Adam, Joachim; Schoen, Uwe
    Journal of Separation Science (2011), 34 (21), 2983-2988CODEN: JSSCCJ; ISSN:1615-9306. (Wiley-VCH Verlag GmbH & Co. KGaA)
    Automated medicinal chem. (parallel chem.) has become an integral part of the drug-discovery process in almost every large pharmaceutical company. Parallel array synthesis of individual org. compds. has been used extensively to generate diverse structural libraries to support different phases of the drug-discovery process, such as hit-to-lead, lead finding, or lead optimization. In order to guarantee effective project support, efficiency in the prodn. of compd. libraries has been maximized. As a consequence, also throughput in chromatog. purifn. and anal. has been adapted. As a recent trend, more labs. are prepg. smaller, yet more focused libraries with even increasing demands towards quality, i.e. optimal purity and unambiguous confirmation of identity. This paper presents an automated approach how to combine effective purifn. and structural conformation of a lead optimization library created by microwave-assisted org. synthesis. The results of complementary anal. techniques such as UHPLC-HRMS and NMR are not only regarded but even merged for fast and easy decision making, providing optimal quality of compd. stock. In comparison with the previous procedures, throughput times are at least four times faster, while compd. consumption could be decreased more than threefold.
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    Lowe, H.; Watson, C. T.; Badal, S.; Ateh, E. N.; Toyang, N. J.; Bryant, J. Anti-Angiogenic Properties of the Jamaican Ball Moss, (Tillandsia Recurvata L.). Int. Res. J. Biol. Sci. 2012, 1, 73– 76
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    Andrighetti-Fröhner, C. R.; Sincero, T. C. M.; da Silva, A. C.; Savi, L. A.; Gaido, C. M.; Bettega, J. M. R.; Mancini, M.; de Almeida, M. T. R.; Barbosa, R. A.; Farias, M. R.; Barardi, C. R. M.; Simões, C. M. O. Antiviral Evaluation of Plants from Brazilian Atlantic Tropical Forest. Fitoterapia 2005, 76, 374– 378,  DOI: 10.1016/j.fitote.2005.03.010
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    32
    Antiviral evaluation of plants from Brazilian Atlantic Tropical Forest
    Andrighetti-Frohner C R; Sincero T C M; da Silva A C; Savi L A; Gaido C M; Bettega J M R; Mancini M; de Almeida M T R; Barbosa R A; Farias M R; Barardi C R M; Simoes C M O
    Fitoterapia (2005), 76 (3-4), 374-8 ISSN:0367-326X.
    The antiviral activity of six medicinal plants from Brazilian Atlantic Tropical Forest was investigated against two viruses: herpes simplex virus type 1 (HSV-1) and poliovirus type 2 (PV-2). Cuphea carthagenensis and Tillandsia usneoides extracts showed the best antiherpes activity. T. usneoides dichloromethane, ethyl acetate and n-butanol extracts, and Lippia alba n-butanol extract showed inhibition of HSV-1, strain 29R/acyclovir resistant. In addition, only L. alba ethyl acetate extract showed antipoliovirus activity. These results corroborate that medicinal plants can be a rich source of potential antiviral compounds.
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    Vieira, B. M.; Kaplan, M. A. C. Tillandsia Usneoides (L.) L. (Bromeliaceae): Aspectos Químicos e Farmacológicos;Rev. Fitos, 2011; Vol. 6, pp 2009– 2012.
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    Witherup, K. M.; McLaughlin, J. L.; Judd, R. L.; Ziegler, M. H.; Medon, P. J.; Keller, W. J. Identification of 3-Hydroxy-3-Methylglutaric Acid (HMG) as a Hypoglycemic Principle of Spanish Moss (TillandsiaUsneoides). J. Nat. Prod. 1995, 58, 1285– 1290,  DOI: 10.1021/np50122a023
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    Identification of 3-hydroxy-3-methylglutaric acid (HMG) as a hypoglycemic principle of Spanish moss (Tillandsia usneoides)
    Witherup, K. M.; McLaughlin, J. L.; Judd, R. L.; Ziegler, M. H.; Medon, P. J.; Keller, W. J.
    Journal of Natural Products (1995), 58 (8), 1285-90CODEN: JNPRDF; ISSN:0163-3864. (American Society of Pharmacognosy)
    Bioactivity-directed fractionation, using brine shrimp lethality and murine hypoglycemia, of an ethanol ext. prepd. from Tillandsia usneoides, led to the isolation of four apparently bioactive compds. from the water-sol. fraction. The compds. were identified as citric acid, succinic acid, 3-hydroxy-3-methylglutaric acid (HMG), and 3,6,3',5'-tetramethoxy-5,7,4'-trihydroxyflavone-7-O-β-D-glucoside. The brine shrimp lethality of the acids was simply due to acidity; however, HMG elicited significant hypoglycemic responses in fasting normal mice. Et and Me esters of citric acid were prepd. and tested in the murine hypoglycemic assay. Five of the predominant sugars were identified by TLC. Free thymidine was also isolated. Further evaluation of HMG and other potential inhibitors of HMG CoA lyase, in the treatment of symptoms of diabetes mellitus, is suggested.
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    Lowe, H.; Toyang, N.; Bryant, J. In vitro and in vivo anti-cancer effects of tillandsia recurvata (ball moss) from Jamaica. W. Indian Med. J. 2013, 62, 177– 80
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    Lowe, H. I. C.; Toyang, N. J.; Watson, C. T.; Badal, S.; Bahado-Singh, P.; Bryant, J. In Vitro Anticancer Activity of the Crude Extract and two Dicinnamate Isolates from the Jamaican Ball Moss (Tillandsia Recurvata L.). Am. Int. J. Contemp. Res. 2013, 3, 93– 96
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    In Vitro Anticancer Activity of the Crude Extract and two Dicinnamate Isolates from the Jamaican Ball Moss (Tillandsia Recurvata L.)
    Lowe Henry Ic; Toyang Ngeh J; Watson Charah; Badal Simone; Bahado-Singh Perceval; Bryant Joseph
    American international journal of contemporary research (2013), 3 (1), 93-96 ISSN:2162-139X.
    A crude chloroform extract from the Jamaican Ball Moss (Tillandsia recurvata L.) was tested for activity against three human cancer cell lines including; A375 (human melanoma), MCF-7 (human breast) and PC-3 (human prostate cancer) using the WST-1 assay. IC50s obtained against these cell lines; A375, MCF-7 and PC-3 in the presence of the crude extract are; 0.9μg/ml, 40.51μg/ml and 5.97μg/ml respectively indicating the promising anti-cancer activity of the ball moss extract. Further, preliminary phytochemical study was conducted in an attempt to identify and isolate the phytochemicals that could possibly be responsible for the observed bioactivity of the ball moss chloroform extract. As a result, two dicinnamates were isolated; 1,3-di-O-Cinnamoyl-glycerol (1) and (E)-3-(cinnamoyloxy)-2-hydroxypropyl 3-(3,4-dimethoxyphenyl)acrylate (2) and we report for the first time isolation of compound 2. Even though the bioactivity of these two islaotes were fairly weak against the cell lines, the results presented here will prove useful for further research aimed at identifying molecules that maybe effective against melanoma, breast and prostate cancers associated with fewer side-effects.
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    Lowe, H. I. C.; Watson, C. T.; Badal, S.; Toyang, N. J.; Bryant, J. Cycloartane-3,24,25-triol inhibits MRCKα kinase and demonstrates promising anti prostate cancer activity in vitro. Cancer Cell Int. 2012, 12, 46,  DOI: 10.1186/1475-2867-12-46
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    Cycloartane-3,24,25-triol inhibits MRCKα kinase and demonstrates promising anti prostate cancer activity in vitro
    Lowe, Henry I. C.; Watson, Charah T.; Badal, Simone; Toyang, Ngeh J.; Bryant, Joseph
    Cancer Cell International (2012), 12 (), 46CODEN: CCIACC; ISSN:1475-2867. (BioMed Central Ltd.)
    Background: Given the high occurrence of prostate cancer worldwide and one of the major sources of the discovery of new lead mols. being medicinal plants, this research undertook to investigate the possible anti-cancer activity of two natural cycloartanes; cycloartane-3,24,25-diol (extd. in our lab from Tillandsia recurvata) and cycloartane-3,24,25-triol (purchased). The inhibition of MRCKα kinase has emerged as a potential soln. to restoring the tight regulation of normal cellular growth, the loss of which leads to cancer cell formation. Methods: Kinase inhibition was investigated using competition binding (to the ATP sites) assays which have been previously established and authenticated and cell proliferation was measured using the WST-1 assay. Results: Cycloartane-3,24,25-triol demonstrated strong selectivity towards the MRCKα kinase with a Kd50 of 0.26 μM from a total of 451 kinases investigated. Cycloartane-3,24,25-triol reduced the viability of PC-3 and DU145 cell lines with IC50 values of 2.226 ± 0.28 μM and 1.67 ± 0.18 μM resp. Conclusions: These results will prove useful in drug discovery as Cycloartane-3,24,25-triol has shown potential for development as an anti-cancer agent against prostate cancer.
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    Lowe, H. I. C.; Toyang, N. J.; Watson, C. T.; Ayeah, K. N. N.; Bryant, J. Antileukemic Activity of Tillandsia Recurvata and Some of Its Cycloartanes. Anticancer Res. 2014, 34, 3505– 3509
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    Antileukemic activity of Tillandsia recurvata and some of its cycloartanes
    Lowe, Henry I. C.; Toyang, Ngeh J.; Watson, Charah T.; Ayeah, Kenneth N. N.; Bryant, Joseph
    Anticancer Research (2014), 34 (7), 3505-3509CODEN: ANTRD4; ISSN:0250-7005. (International Institute of Anticancer Research)
    Background: Approx. 250,000 deaths were caused by leukemia globally in 2012 and about 40%-50% of all leukemia diagnoses end-up in death. Medicinal plants are a rich source for the discovery of new drugs against leukemia and other types of cancers. To this end, we subjected the Jamaican ball moss (Tillandsia recurvata) and its cycloartanes, as well as some analogs, to in vitro screening against a no. of leukemia cell lines. The WST-1 anti-proliferation assay was used to det. the anticancer activity of ball moss and two cycloartanes isolated from ball moss and four of their analogs against four leukemia cell lines (HL-60, K562, MOLM-14, monoMac6). Ball moss crude methanolic ext. showed activity with a 50% inhibition concn. (IC50) value of 3.028 μg/mL against the Molm-14 cell line but was ineffective against HL-60 cells. The six cycloartanes tested demonstrated varying activity against the four leukemia cancer cell lines with IC50 values ranging from 1.83 μM to 18.3 μM. Five out of the six cycloartanes demonstrated activity, while one was inactive against all four cell lines. The preliminary activity demonstrated by the Jamaican ball moss and its cycloartanes against selected leukemia cell lines continues to throw light on the broad anticancer activity of ball moss. Further studies to evaluate the efficacy of these mols. in other leukemia cell lines are required in order to validate the activity of these mols., as well as to det. their mechanisms of action and ascertain the activity in vivo in order to establish efficacy and safety profiles.
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    Lowe, H. I. C.; Toyang, N. J.; Watson, C. T.; Ayeah, K. N.; Bryant, J. HLBT-100: A Highly Potent Anti-Cancer Flavanone from Tillandsia Recurvata (L.) L. Cancer Cell Int. 2017, 17, 1– 12,  DOI: 10.1186/s12935-017-0404-z
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    Weld, J. T. The Antibiotic Action of TillandsiaUsneoides (Spanish Moss). Exp. Biol. Med. 1945, 59, 40– 41,  DOI: 10.3181/00379727-59-14972P
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    Antibiotic action of Tillandsia usneoides (Spanish moss)
    Weld, Julia T.
    Proceedings of the Society for Experimental Biology and Medicine (1945), 59 (), 40-1CODEN: PSEBAA; ISSN:0037-9727.
    Preliminary. A method for extg. an antibiotic substance from the brown portions of the plant is described. The crude ext. is effective against all gram-pos. bacteria tested and against Cryptococcus hominis, but has no inhibitory effect on growth of H. influenzae A, Ps. pyocyaneus, E. coli, and B. proteus.
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    Webber, M. G.; Lauter, W. M.; Foote, P. A. A Preliminary Phytochemical Study of TillandsiaUsneoides L. (Spanish Moss). J. Am. Pharm. Assoc. Sci. Ed. 1952, 41, 230– 235,  DOI: 10.1002/jps.3030410503
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    Paz, E. A.; Cerdeiras, M. P.; Fernandez, J.; Ferreira, F.; Moyna, P.; Soubes, M.; Vázquez, A.; Vero, S.; Zunino, L. Screening of Uruguayan Medicinal Plants for Antimicrobial Activity. J. Ethnopharmacol. 1995, 45, 67– 70,  DOI: 10.1016/0378-8741(94)01192-3
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    Faller, E. M.; Zajmi, A.; Kanes, S. N. In Vitro Antibacterial Activity of Spanish Moss (Tillandsia usneoides) Crude Extract Against Skin Infection in Wound Healing. Int. J. Pharmacogn. Phytochem. Res. 2017, 9, 1344– 1352,  DOI: 10.25258/phyto.v9i10.10459
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    Zheng, L.; Chen, H.; Han, X.; Lin, W.; Yan, X. Antimicrobial Screening and Active Compound Isolation from Marine Bacterium NJ6-3-1 Associated with the Sponge Hymeniacidon Perleve. World J. Microbiol. Biotechnol. 2005, 21, 201– 206,  DOI: 10.1007/s11274-004-3318-6
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    Antimicrobial screening and active compound isolation from marine bacterium NJ6-3-1 associated with the sponge Hymeniacidon perleve
    Zheng, Li; Chen, Haimin; Han, Xiaotian; Lin, Wei; Yan, Xiaojun
    World Journal of Microbiology & Biotechnology (2005), 21 (2), 201-206CODEN: WJMBEY; ISSN:0959-3993. (Springer)
    Twenty-nine marine bacterial strains were isolated from the sponge Hymeniacidon perleve at Nanji island, and antimicrobial screening showed that eight strains inhibited the growth of terrestrial microorganisms. The strain NJ6-3-1 with wide antimicrobial spectrum was identified as Pseudoalteromonas piscicida based on its 16S rRNA sequence anal. The major antimicrobial metabolite, isolated through bioassay-guide fractionation of TLC bioautog. overlay assay, was identified as norharman (I) (a beta-carboline alkaloid) by EI-MS and NMR.
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    Wang, M.; Zhang, Y.; Wang, R.; Wang, Z.; Yang, B.; Kuang, H. An Evolving Technology That Integrates Classical Methods with Continuous Technological Developments: Thin-Layer Chromatography Bioautography. Molecules 2021, 26, 4647,  DOI: 10.3390/molecules26154647
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    An Evolving Technology That Integrates Classical Methods with Continuous Technological Developments: Thin-Layer Chromatography Bioautography
    Wang, Meng; Zhang, Yirong; Wang, Ruijie; Wang, Zhibin; Yang, Bingyou; Kuang, Haixue
    Molecules (2021), 26 (15), 4647CODEN: MOLEFW; ISSN:1420-3049. (MDPI AG)
    A review. Thin-layer chromatog. (TLC) bioautog. is an evolving technol. that integrates the sepn. and anal. technol. of TLC with biol. activity detection technol., which has shown a steep rise in popularity over the past few decades. It connects TLC with convenient, economic and intuitive features and bioautog. with high levels of sensitivity and specificity. In this study, we discuss the research progress of TLC bioautog. and then establish a definite timeline to introduce it. This review summarizes known TLC bioautog. types and practical applications for detg. antibacterial, antifungal, antitumor and antioxidant compds. and for inhibiting glucosidase, pancreatic lipase, tyrosinase and cholinesterase activity constitutes. Nowadays, esp. during the COVID-19 pandemic, it is important to identify original, natural products with anti-COVID potential compds. from Chinese traditional medicine and natural medicinal plants. We also give an account of detection techniques, including in situ and ex situ techniques; even in situ ion sources represent a major reform. Considering the current tech. innovations, we propose that the technol. will make more progress in TLC plates with higher sepn. and detection technol. with a more portable and extensive scope of application. We believe this technol. will be diffusely applied in medicine, biol., agriculture, animal husbandry, garden forestry, environmental management and other fields in the future.
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    Flores, S. E.; Herrán, J. The Structure of Pendulin and Penduletin: A New Flavonol Glucoside Isolated from Brickelia Pendula. Tetrahedron 1958, 2, 308– 315,  DOI: 10.1016/0040-4020(58)88052-7
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    Structure of pendulin and penduletin. New flavonol glucoside from Brickelia pendula
    Flores, S. E.; Herran, J.
    Tetrahedron (1958), 2 (), 308-15CODEN: TETRAB; ISSN:0040-4020.
    The glucoside pendulin (I) was hydrolyzed to give the new flavone, penduletin (ll), 4,5-dihydroxy-3,6,7-trimethoxyflavone to which 1 mole glucose is attached at the 4'-position. The Mexican plants known as Atanasia amarga have a bitter taste and are used indigenously for "stomach ailments" [Rio de la Loza, Materia Medica Mexicana, Pt I, 269 (1894)] and a member of the species Brickelia squarrosa was reported to contain a glycoside. Finely ground sun-dried B. pendula (2.8 kg.) extd. 3 times with 10 l. boiling alc. the exts. concd. in vacuo to 3 l., the viscous green mass washed 5 times with 2 l. hot hexane, and the residual yellow powder taken up in alc., the decolorized (Norit) soln. recrystd. (alc. and Me2CO-C6H14) gave 30 g. I, C24H26O12, m. 178-9°, [α]D22 -34° (C5H5N), v 3200, 1660, 1600, 1300-1180, 1090, 838, 810, 794 cm. -1, λ 212, 272, 332 mμ (ε 38,166, 23,013, 22,040), contg. 3 MeO groups, Rf 0.76 (in 4:1:5 BuOH-AcOH-H2O on Whatman No. 1 paper at 23° in 8 hrs. and visualization in ultraviolet light). I (0.5 g.) in 300 ml. 70% alc. contg. 15% HCl refluxed 6 hrs., the soln. dild. with 1 l. H2O, extd. 4 times with 200 ml. EtOAc, and the dried Na2SO4) ext. crystd. (dil. alc. and dil. Me2CO) yielded 0.3 g. II, C18H16O7, m. 216-17°, v 3100, 1600, 1300, 1180, 762 cm.-1, λ 212, 271, 341 mμ(ε 33,376, 19,231, 22,767), giving a crimson color in alc. on treatment with Na-Hg, pink color with Mg and HCl, and an intense yellow soln. in concd. H2SO4; diacetate (IIa), m. 157-8°, sapond. by boiling 1 hr. with alc. NaOH; di-Me deriv. (III), m. 152-3° (alc. and Me2CO-C6H14). II (0.5 g.) in 100 ml. alc. and 20 ml. 20% NaOH in 70% alc. treated slowly with 10 ml. Et2SO4, the mixt. refluxed 30 min., treated with 20 ml. Et2SO4, and refluxed 5 hrs. under const. const, alky., the cooled soln. dild. with 300 ml. H2O and extd. with EtOAc, the ext. evapd., and the residue crystd. (dil. alc. and Me2CO-C6H14) gave 0.31 g. 4'-ethoxy-5-hydroxy-3,6,7-trimethoxyflavone (IV), C20H20O7, m. 166-7°, λ212, 272, 336 mμ (ε 39,690, 22,138, 24,711); acetate, m. 149-50. The aq. fraction from the acid hydrolysis of I concd. to 500 ml. and neutralized gave pos. reactions with Fehling and Tollens reagents. Parallel paper chromatograms of the aq. ext. and glucose soln. developed according to Horrocks and Manning (C.A. 43, 8426h) gave identical spots. Similarly, chromatograms of the osazone and glucosazone obtained by the procedure of Burton, et al. (C.A. 45, 4297b), gave identical spots. II (0.4 g.) in 10 ml. (EtCO)2O refluxed 2 hrs. with 0.3 g. PhOH and 18 ml. freshly distd. 55% HI, the mixt. dild. with 100 ml. H2O, extd. with Et2O and EtOAc, the org. fractions washed 3 times with aq. Na2S2O3, and the dried ext. evapd. yielded 3,4',5,6,7-pentahydroxyflavonol (V), C15H10O7, m. 290° (decompn., charing between 314-20°); pentaacetate, m. 234-5°. Methylation of V with CH2N2 by the usual technique regenerated III. III (0.5 g.) in 50 ml. alc. and 50 ml. 20% KOH in 70% alc. boiled 20 hrs. and the concd. soln. dild. with H2O, satd. with CO2, acidified with HCl, extd. with Et2O, and the product recrystd. (dil. Me2CO) gave 0.05 g. p-MeOC6H4CO2H, m. 183-4°. A similar fission of IV gave p-EtOC6H4CO2H, m. 194-5°. Ozonolysis of III and IV gave identical results, demonstrating the presence of only a 4'-substituent in the benzene ring of II. IIa (0.1 g.) in 40 ml. anhyd. EtOAc ozonized 7 min., the ozonide decompd. by hydrogenation with 5% Pd-C, the filtered soln. evapd., and the residue crystd. (Me2CO-C6H6) gave an acid, sublimed at 125°/0.01 mm. to yield 0.02 g. p-AcOC6H4CO2H. V gave a pink color with Mg and HCl, and orange ppt. with Pb(OAc)2 in alc., turning brown on standing, and dark olive-green color with alc. FeCl3, identical with those reported by Goldsworthy and Robinson (C.A. 31, 22139) for V. III was identical with a specimen of authentic 3,4',5,6,7-pentamethoxyflavone. I (1 g.) in MeOH and CH2N2 (from 18 g. H2NCON(NO)Me) in Et2O kept 24 hrs. and treated with CH2N2 (10 g. H2NCON(NO)Me) in Et2O, the mixt. kept 24 hrs. and again treated with CH2N2 (10 g. H2NCON(NO)Me), kept 24 hrs., and evapd. at 20° in vacuo, the residue chromatographed in dry Me2CO on 150 g. Magnesol and eluted in succession with Me2CO, moist EtOAc, and 50% alc., the final fraction crystd. (dil. alc. and dil. Me2CO) (N atm.) gave 0.6 g. tetramethoxy compd. (VI), C25H28O12, m. 227-8° (decompn.), λ 212, 267, 326 mμ (ε 39,651, 27,627, 29,695). VI (0.8 g.) in 50 ml. 10% HCl in dil. alc. refluxed 3.5 hrs., the soln. dild. with 100 ml. H2O, the mixt. extd. 3 times with 40 ml. EtOAc, and the product crystd. (dil. alc.) gave 0.4 g. monohydroxytetramethoxy compd. (VII), C19H18O7, m. 253-4° λ 212, 260, 330 mμ (ε 38,871, 19,630, 26,641), converted by methylation with CH2N2 in Et2O to III and acetylated to a monoacetate (VIII), m. 151-3° (decompn.). VIII (0.075 g.) in anhyd. EtOAc ozonized 3 min., the ozonide hydrogenated with 0.1 g. 5% Pd-C, the filtered soln. evapd., and the crystd. (Me2CO-C6H6) residue sublimed at 125°/0.01 mm. gave 0.013 g. p-AcOC6H4CO2H, indicating that the glucose mol. in I is attached to the 4'-position in II.
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  47. 47
    Schilling, E. E.; Panero, J. L.; Crozier, B. S.; Scott, R. W.; Dávila, P. Bricklebush (Brickellia) Phylogeny Reveals Dimensions of the Great Asteraceae Radiation in Mexico. Mol. Phylogenet. Evol. 2015, 85, 161– 170,  DOI: 10.1016/j.ympev.2015.02.007
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    Bricklebush (Brickellia) phylogeny reveals dimensions of the great Asteraceae radiation in Mexico
    Schilling Edward E; Panero Jose L; Crozier Bonnie S; Scott Randall W; Davila Patricia
    Molecular phylogenetics and evolution (2015), 85 (), 161-70 ISSN:.
    Data from molecular phylogenetics were used to assess aspects of diversity and relationships in Brickellia, a large and widespread genus of Eupatorieae. The dataset included sequence data from nuclear ribosomal ITS, ETS, and plastid psbA-trnH regions. An initial question was to assess the monophyly of the genus and whether Barroetea, Phanerostylis, and Kuhnia should be recognized as separate from or included in Brickellia. The results supported the hypothesis that Brickellia is monophyletic, with the small (2-3 species) Pleurocoronis as the sister group and showed Barroetea, Phanerostylis, and Kuhnia all embedded within the genus. Results of a time calibrated phylogeny from a BEAST analysis gave an estimated origination time for Brickellia at about 9 million years ago (Ma), with the oldest split within the genus dated at about 7.5Ma. A BAMM analysis based on the time calibrated tree showed that Brickellia has one rate shift in diversification associated with its origin in the late Miocene. Some lineages within the genus have had an increase in the rate of diversification over the past 5Ma, whereas other lineages have had a decrease in net diversification during this period. The results also elucidated nine clades within Brickellia which are accepted as taxonomic sections, and that will form logical units for future detailed studies.
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    Sharaf, M.; Mansour, R. M. A.; Saleh, N. A. M. Exudate Flavonoids from Aerial Parts of Four CleomeSpecies. Biochem. Syst. Ecol. 1992, 20, 443– 448,  DOI: 10.1016/0305-1978(92)90084-Q
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    Exudate flavonoids from aerial parts of four Cleome species
    Sharaf, Mohamed; Mansour, Ragaa M. A.; Saleh, Nabiel A. M.
    Biochemical Systematics and Ecology (1992), 20 (5), 443-8CODEN: BSECBU; ISSN:0305-1978.
    The aerial parts of four Cleome species (Capparaceae) were investigated for their surface flavonoids. Ten methylated flavonoids were isolated and identified as 5,7,4'-trihydroxy-3-methoxyflavone (isokaempferide), 5,7,4'-trihydroxy-3,3'-dimethyoxyflavone, 5,7,4'-trihydroxy-6,3'-dimethoxyflavone (jaceosidin), 5,4'-dihydroxy-3,6,7-trimethoxyflavone (penduletin), 5,7,3',4'-tetrahydroxy-3,6-dimethoxyflavone (axillarin), 5,7,4'-trihydroxy-6,3',5'-trimethoxyflavone, 5,4'-dihydroxy-3,6,7,3'-tetramethoxyflavone (chrysosplenetin), 5,3'-dihydroxy-3,6,7,4',5'-pentamethoxyflavone, 5,4'-dihydroxy-3,6,7,8,3'-pentamethoxyflavone and 5-hydroxy-3,6,7,3',4',5'-hexamethoxyflavone.
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  49. 49
    Bai, N.; He, K.; Zhou, Z.; Lai, C.-S.; Zhang, L.; Quan, Z.; Shao, X.; Pan, M.-H.; Ho, C.-T. Flavonoids from Rabdosia Rubescens Exert Anti-Inflammatory and Growth Inhibitory Effect against Human Leukemia HL-60 Cells. Food Chem. 2010, 122, 831– 835,  DOI: 10.1016/j.foodchem.2010.03.071
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    Flavonoids from Rabdosia rubescens exert anti-inflammatory and growth inhibitory effect against human leukemia HL-60 cells
    Bai, Naisheng; He, Kan; Zhou, Zhu; Lai, Ching-Shu; Zhang, Li; Quan, Zheng; Shao, Xi; Pan, Min-Hsiung; Ho, Chi-Tang
    Food Chemistry (2010), 122 (3), 831-835CODEN: FOCHDJ; ISSN:0308-8146. (Elsevier Ltd.)
    Eight flavonoids were isolated from the aerial parts of the Rabdosia rubescens plant. Their chem. structures were detd. using 1D and 2D NMR and high-resoln. MS data. The flavonoids were tested for cytotoxicity in cancer cell lines (Hep G2, COLO 205, MCF-7, HL-60) and anti-inflammatory activity in LPS-treated RAW264.7 macrophages in vitro. Two compds. were modestly active in inhibiting nitrite prodn. by macrophages. One compd. was selectively active against HL-60 cells with IC50 = 7.55 μM. This value was comparable to IC50 4.64 μM of doxorubicin (pos. control).
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    Bukhari, I. A.; Khan, R. A.; Gilani, A. H.; Shah, A. J.; Hussain, J.; Ahmad, V. U. The analgesic, anti-inflammatory and calcium antagonist potential ofTanacetum artemisioides. Arch. Pharmacal Res. 2007, 30, 303– 312,  DOI: 10.1007/BF02977610
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    The analgesic, anti-inflammatory and calcium antagonist potential of Tanacetum artemisioides
    Bukhari, Ishfaq Ali; Khan, Rafeeq Alam; Gilani, Anwar-ul Hassan; Shah, Abdul Jabbar; Hussain, Javid; Ahmad, Viqar Uddin
    Archives of Pharmacal Research (2007), 30 (3), 303-312CODEN: APHRDQ; ISSN:0253-6269. (Pharmaceutical Society of Korea)
    Several species of the genus Tanacetum are traditionally used in a variety of health conditions including pain, inflammation, respiratory and gastrointestinal disorders. In the current investigation, we evaluated the plant ext. of T. artemisioides and some of its pure compds. (flavonoids) for analgesic, anti-inflammatory and calcium antagonist effects in various in-vivo and in vitro studies. Using the acetic acid induced writhing test, i.p. administration of the plant ext. (25-50 mg/kg) and its flavonoid compds. TA-1 and TA-2 (1-5 mg/kg) exhibited significant analgesic activity. The max. analgesic effect obsd. with the crude ext. of the plant was 71% at 50 mg/kg, while that of compds. TA-1 and TA-2 (5 mg/kg i.p) was 75 and 47%, resp. The plant ext. and its pure compds. caused inhibition of formalin induced paw licking in mice predominantly in the second phase of the test. Diclofenac sodium, a std. ref. compd., showed a similar effect in these chem. induced pain models. In the carrageenan induced rat paw edema assay, the plant ext. (50-200 mg/kg i.p) demonstrated significant (P < 0.01) anti-inflammatory activity which was comparable to that obtained with diclofenac sodium and indomethacin. In isolated rabbit jejunum prepns. the plant ext. showed an atropine sensitive dose-dependent (0.10-1.0 mg/mL) spasmogenic activity followed by a spasmolytic effect at the next higher doses (3-5 mg/mL). The crude ext. of the plant also inhibited the high K+-induced contractions, indicating a calcium channel blocking (CCB) activity, which was further confirmed when the plant ext. caused a right-ward shift in the Ca++ concn. response curves in the isolated rabbit jejunum prepns., similar to that seen with verapamil. The flavonoid compds. isolated from the plant were devoid of any activity in the isolated tissue prepns. These results indicate that the plant ext. of T. artemisioides possesses analgesic, anti-inflammatory and CCB activities. The flavonoid compds. of the plant may have a role in its obsd. analgesic and anti-inflammatory activities, while the CCB activity of the plant may be attributed to some other chem. constituents present. Moreover the findings support the traditional reputation of the genus Tanacetum for its therapeutic benefits in pain and inflammatory conditions.
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    Halfon, B.; Cifrçi, E.; Topçu, G. Flavonoid Constituents of Sideritis Caesarea. Turk. J. Chem. 2013, 37, 464– 472,  DOI: 10.3906/kim-1206-45
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    Flavonoid constituents of Sideritis caesarea
    Halfon, Belkis; Ciftci, Ece; Topcu, Gulacti
    Turkish Journal of Chemistry (2013), 37 (3), 464-472CODEN: TJCHE3; ISSN:1300-0527. (Scientific and Technological Research Council of Turkey)
    The acetone ext. of the aerial parts of Sideritis caesarea Duman, Aytac & Baser (Lamiaceae) afforded the flavonoids penduletin (1) and apigenin (2) and 6 glycosylated flavonoids, 4'-O-methyl-isoscutellarein-7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-6''-O-acetyl-β-D-glucopyranoside (3), 4'-O-methylhypolaetin-7-O-[6''-O-acetyl-β-D-allopyranosyl-(1→2)]-6''-O-acetyl-β-D-glucopyranoside (4), isoscutellarein-7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-6''-O-acetyl-β-D-glucopyranoside (5), isoscutellarein-7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (6), 4'-O-methylhypolaetin-7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (7), and hypolaetin-7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (8). The compds. were identified by the use of 1D- and 2D-NMR and UV spectroscopic techniques and by comparisons with the reported data. The acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities of the acetone, methanol, and water exts. of the plant and of the flavones penduletin and apigenin were evaluated at 200 μg/mL. The water ext. exhibited better activity against the enzyme AChE as compared to both the acetone and the methanol exts. Penduletin (1) showed significant activity against BChE (66.58%) while apigenin (2) showed weak activity against both enzymes.
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    Flavonoids from Digitalis thapsi leaves
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    Planta Medica (1980), 38 (3), 271-2CODEN: PLMEAA; ISSN:0032-0943.
    From the leaves of D. thapsi 7 flavonoids were isolated: 3,3',7-trimethylquercetin, polycladin, 3'-methoxycalycopterin, jaranol, calycopterin, penduletin, and cirsimaritin. Calycopterin was the only flavonol previously described in this species.
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    The dried leaves of Artemisia annua, collected from Sichuan Province in Southern China, have yielded the unusual cadinane sesquiterpene I oxygenated at the 7-position and the novel eudesmane sesquiterpene II, in addn. to several known sesquiterpenes and flavanoids.
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    Muhammad, A.; Tel-Cayan, G.; Öztürk, M.; Nadeem, S.; Duru, M. E.; Anis, I.; Ng, S. W.; Shah, M. R. Biologically active flavonoids from Dodonaea viscosa and their structure-activity relationships. Ind. Crops Prod. 2015, 78, 66– 72,  DOI: 10.1016/j.indcrop.2015.10.011
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    Biologically active flavonoids from Dodonaea viscosa and their structure-activity relationships
    Muhammad, Akhtar; Tel-Cayan, Gulsen; Ozturk, Mehmet; Nadeem, Said; Duru, Mehmet E.; Anis, Itrat; Ng, Seik W.; Shah, Muhammad R.
    Industrial Crops and Products (2015), 78 (), 66-72CODEN: ICRDEW; ISSN:0926-6690. (Elsevier B.V.)
    Antioxidant and anticholinesterase activities of twelve flavonoids i.e. santin (1), penduletin (2), viscosine (3), 6,7-dimethylkaempferol (4), kaempferol- 3- methylether (5), 3,4'-dimethoxy-5,7-dihydroxyflavone (6), 5,7,4'-trihydroxy-3'-(3-hydroxymethylbutyl)-3,6-dimethoxyflavone (7), 5,7-dihydroxy-3'-(2-hydroxy-3-methyl-3-butenyl)-3,6,4'-trimethoxy-flavone (8), 5,7-dihydroxy-3'-(3-hydroxy-methylbutyl)-3,6,4'-trimethoxyflavone (9), 5,7-dihydroxy-3'-(4''-acetoxy-3''-methylbutyl)-3,6,4'-trimethoxy flavone (10), aromadendrin, (2S,3S) 3,4',5,7-tetrahydroxyflavanone (11), and pinocembrin (12), together with monohydrated crystal (1A) of 1 and anhyd. crystal (3A) of 3 - isolated from Dodonaea viscosa - were studied. The results are given as 50% inhibition concns. (IC50). Their structure-activity relationships are discussed for both activities. Flavonoids 3 and 10 showed higher antioxidant activity in all tests. 3 Also showed moderate acetylcholinesterase (IC50: 182.97 ± 1.25 μM) and significant butyrylcholinesterase (IC50: 47.07 ± 0.54 μM) inhibitory activities. Compds. 2 (IC50: 55.78 ± 1.01 μM) and 3A (IC50: 58.72 ± 1.02 μM) were also moderate anticholinesterase agents against butyrylcholinesterase enzyme. Monohydrate crystal (1A) showed better antioxidant and anticholinesterase activities than its amorphous form (1). In contrast, the amorphous 3 exhibited better activity than the anhyd. crystal (3A). In hydrous crystal, the water mol. might be responsible for better activity. These natural flavonoids can be used as pharmaceuticals and/or preservatives in resp. industries.
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    Arslanian, R. L.; Stermitz, F. R.; Castedo, L. 3-Methoxy-5-Hydroxyflavonols from TillandsiaPurpurea. J. Nat. Prod. 1986, 49, 1177– 1178,  DOI: 10.1021/np50048a062
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    3-Methoxy-5-hydroxyflavonols from Tillandsia purpurea
    Arslanian, Robert L.; Stermitz, Frank R.; Castedo, Luis
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    Retusin and artemetin were isolated from T. purpurea and identified by 1H NMR, UV spectroscopy and TLC comparisons with stds. Penduletin 4'-O-Me ether was tentatively identified. Several addnl. methoxylated 5-hydroxyflavones were detected.
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    Sagir, Z. O.; Carikci, S.; Kilic, T.; Goren, A. C. Metabolic Profile and Biological Activity of Sideritis Brevibracteata P. H. Davis Endemic to Turkey. Int. J. Food Prop. 2017, 20, 2994– 3005,  DOI: 10.1080/10942912.2016.1265981
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    Metabolic profile and biological activity of Sideritis brevibracteata P. H. Davis endemic to Turkey
    Sagir, Zuleyha Ozer; Carikci, Sema; Kilic, Turgut; Goren, Ahmet C.
    International Journal of Food Properties (2017), 20 (12), 2994-3005CODEN: IJFPFO; ISSN:1094-2912. (Taylor & Francis, Inc.)
    Essential oil and phenolic compns. of Sideritis brevibracteata P. H. Davis, which is an endemic species in Turkey and commonly used as a herbal tea for some diseases, were detd. by GC-MS and Liq. chromatog.-mass spectrometry (LC-MS/MS) techniques. While the main components of the essential oil were detd. as caryophyllene, germacrene-D, and α-cadinene, the phenolic compds. quercetagetin-3,6-dimethylether and chlorogenic acid were found to be the main compds. in the exts. of the species. The characteristic diterpenoids of Sideritis species such as siderol, linearol, eubotriol, sideridiol, and athonolone were isolated and their structures were elucidated by 1D and 2D NMR (NMR) techniques. Weak inhibitory activity of species against butyryl-cholinesterase was detd. Antioxidant capacity of the acetone and methanol exts. was detd. by DPPH free radical scavenging activity, β-carotene linoleic acid assays, and CUPRAC assays.
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    Pettit, G. R.; Meng, Y.; Herald, D. L.; Stevens, A. M.; Pettit, R. K.; Doubek, D. L. Antineoplastic Agents 540. The Indian Gynandropsis Gynandra (Capparidaceae). Oncol. Res. 2005, 15, 59– 68,  DOI: 10.3727/096504005775082039
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    Oncology Research (2005), 15 (2), 59-68CODEN: ONREE8; ISSN:0965-0407. (Cognizant Communication Corp.)
    The CH3OH-CH2Cl2 ext. of an Indian collection (entire plant) of Gynandropsis gynandra (L.) Briq. was sepd. based on bioassay results employing cancer cell lines. Six cancer cell growth inhibitors were isolated and found to be known flavone apegenin (4) and flavonols 1-3, 5, and 6. The structure of flavonol 2 was confirmed by x-ray crystal structure detn. All of the five flavonols (1-3, 5, 6) inhibited the murine P388 lymphocytic leukemia cell line with ED50 values of 3.0, 9.2, 4.0, 0.37, and 3.9 μg/mL, resp. All six of the flavonoids (1-6) also exhibited activity against a panel of six human cancer cell lines. Penduletin (3) inhibited growth of the Gram-neg. pathogen Neisseria gonorrhoeae and apegenin (4) inhibited growth of the Gram-pos. opportunist Enterococcus faecalis.
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    Sachdev, Kusum; Kulshreshtha, Dinesh K.
    Phytochemistry (Elsevier) (1983), 22 (5), 1253-6CODEN: PYTCAS; ISSN:0031-9422.
    Eight flavonoids, including the novel compd. I, were isolated from D. viscosa. The structure of I was detd. by std. spectral methods.
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    The major flavonoid of Dodonaea angustifolia
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    Fitoterapia (2000), 71 (5), 602-604CODEN: FTRPAE; ISSN:0367-326X. (Elsevier Science B.V.)
    The major leaf flavonoid of Dodonaea angustifolia, an important South African traditional medicine, has been identified as 5,7,4'-trihydroxy-3,6-dimethoxyflavone.
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    Teffo, L. S.; Aderogba, M. A.; Eloff, J. N. Antibacterial and Antioxidant Activities of Four Kaempferol Methyl Ethers Isolated from Dodonaea Viscosa Jacq. Var. Angustifolia Leaf Extracts. S. Afr. J. Bot. 2010, 76, 25– 29,  DOI: 10.1016/j.sajb.2009.06.010
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    Antibacterial and antioxidant activities of four kaempferol methyl ethers isolated from Dodonaea viscosa Jacq. var. angustifolia leaf extracts
    Teffo, L. S.; Aderogba, M. A.; Eloff, J. N.
    South African Journal of Botany (2010), 76 (1), 25-29CODEN: SAJBDD; ISSN:0254-6299. (Elsevier B.V.)
    Fractionation of dichloromethane and acetone fractions obtained by serial extn. from the leaf powder of Dodonaea viscosa Jacq. var. angustifolia (Sapindaceae) resulted in the isolation of four kaempferol Me ethers. The compds. were identified by spectral data (1H NMR, 13C NMR and MS) as: 3, 5, 7-trihydroxy-4'-methoxyflavone (1); 5, 7, 4'-trihydroxy-3, 6-dimethoxyflavone (2); 5, 7-dihydroxy-3, 6, 4'-trimethoxyflavone (santin) (3); and 5-hydroxy -3, 7, 4'-trimethoxyflavone (4) together with 3,4',5,7-tetrahydroxy flavone (kaempferol) (5). Antioxidant potential of the compds. was evaluated using a DPPH spectrophotometric assay, while antibacterial activity was detd. using a serial diln. microplate technique. The isolates demonstrated varying degrees of antioxidant and antibacterial activities. Of all the compds. investigated, compds. 1 and 5 demonstrated some antioxidant activity (EC50 = 75.49±1.76 μM and 35.06±0.85 resp.) but lower than L-ascorbic acid (EC50 = 13.55±0.28 μM) used as a std. antioxidant agent. The min. inhibitory concn. (MIC) of isolated compds. against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli and Pseudomonas aeruginosa varied from 16 μg/mL to more than 250 μg/mL. Some structure activity relationships could be established for these compds.
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    Khan, A.; Iqbal, Z.; Khan, A.; Khan, I.; Nasir, F.; Khan, I.; Khan, J. A. Pharmacokinetic Profiling of a Novel Flavonoid “Viscosine” from Dodonaea Viscosa Using High Performance Liquid Chromatography. J. Liq. Chromatogr. Relat. Technol. 2015, 38, 128– 136,  DOI: 10.1080/10826076.2014.883542
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    Pharmacokinetic Profiling of a Novel Flavonoid "Viscosine" from Dodonaea viscosa Using High Performance Liquid Chromatography
    Khan, Amirzada; Iqbal, Zafar; Khan, Abad; Khan, Inamullah; Nasir, Fazli; Khan, Ismail; Khan, Jamshaid Ali
    Journal of Liquid Chromatography & Related Technologies (2015), 38 (1), 128-136CODEN: JLCTFC; ISSN:1082-6076. (Taylor & Francis, Inc.)
    Pharmacokinetic (PK) profiling of a novel flavonoid "Viscosine" was carried out in healthy rabbits following both IV and oral administration. Various PK parameters were investigated using the developed HPLC-UV method. The concn. of the Viscosine in plasma samples following both IV and oral administration was plotted as a function of time on normal and semi-log graph papers. The plasma drug concn. as a function of time profile of the Viscosine following IV bolus administration and oral administration showed the bi-exponential decline that indicates that PK of the Viscosine follows two compartment open model. The Viscosine is rapidly but incompletely absorbed following oral administration from hard gelatin capsules and tmax was achieved just in 0.5 h (30 min). The mean ± SD of Cmax was 0.981 ± 0.021 μg/mL. The very low plasma drug concn. achieved shows that Viscosine has lower permeability following oral administration. Similarly, following IV bolus drug administration, the plasma drug concn. as a function of time curve of Viscosine was a bi-exponential curve that follows two compartment open model. Viscosine is readily distributed and established equil. between central and peripheral compartments. Higher vol. of distribution (Vd) shows the longer stay in the peripheral compartments. The β-elimination half-life is approx. 3.8 h. The AUC values also indicate the distribution of the drug in various body fluids. In summary, the bioavailability of the drug after oral administration (F = 0.32) indicates that Viscosine is a low sol. drug; however, the Vd was higher compared with the IV bolus injection while MRT was about 15.45 h. These studies indicate that capsules can be used as a suitable dosage form for the administration of Viscosine.
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    New 6-methoxyflavonols from Centaurea jacea
    Rosler, Heinz; Star, Aura E.; Mabry, Tom J.
    Phytochemistry (Elsevier) (1971), 10 (2), 450-1CODEN: PYTCAS; ISSN:0031-9422.
    Two new flavonols were isolated from C. jacea flowers. They are 4',5,7-trihydroxy-3,6-dimethoxyflavone and its 7-O-β-D-glucoside.
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    Selim, R. M.; Shaaban, M.; Hamdy, A. A.; Abou Zeid, A. A.; Ata, A. V. Viscosine: A new microbial flavonoid from marine-derived,Streptomycessp. RMS518F. Vietnam J. Chem. 2019, 57, 288– 295,  DOI: 10.1002/vjch.201900034
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    Viscosine: A new microbial flavonoid from marine-derived, Streptomyces sp. RMS518F
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    A review. Flavonoids are ubiquitous in photosynthesizing cells and are commonly found in fruit, vegetables, nuts, seeds, stems, flowers, tea, wine, propolis and honey. For centuries, prepns. contg. these compds. as the principal physiol. active constituents have been used to treat human diseases. Increasingly, this class of natural products is becoming the subject of anti-infective research, and many groups have isolated and identified the structures of flavonoids possessing antifungal, antiviral and antibacterial activity. Moreover, several groups have demonstrated synergy between active flavonoids as well as between flavonoids and existing chemotherapeutics. Reports of activity in the field of antibacterial flavonoid research are widely conflicting, probably owing to inter- and intra-assay variation in susceptibility testing. However, several high-quality investigations have examd. the relationship between flavonoid structure and antibacterial activity and these are in close agreement. In addn., numerous research groups have sought to elucidate the antibacterial mechanisms of action of selected flavonoids. The activity of quercetin, for example, has been at least partially attributed to inhibition of DNA gyrase. It has also been proposed that sophoraflavone G and (-)-epigallocatechin gallate inhibit cytoplasmic membrane function, and that licochalcones A and C inhibit energy metab. Other flavonoids whose mechanisms of action have been investigated include robinetin, myricetin, apigenin, rutin, galangin, 2,4,2'-trihydroxy-5'-methylchalcone and lonchocarpol A. These compds. represent novel leads, and future studies may allow the development of a pharmacol. acceptable antimicrobial agent or class of agents.
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    Microbial Pathogenesis (2020), 149 (), 104571CODEN: MIPAEV; ISSN:0882-4010. (Elsevier Ltd.)
    Staphylococcus aureus is an opportunistic pathogen involved in several human diseases and presents ability to produce many virulence factors and resistance to antibacterial agents. One of the current strategies to combat such multidrug resistant bacteria is the antibacterial combination therapy. Myricetin is a flavonoid capable of inhibiting several S. aureus virulence factors without influencing on bacterial growth. Therefore, the combination of antibacterials with the antivirulence compd. myricetin may provide a pos. interaction to control multidrug resistant-bacteria. This work aims to evaluate the effect of the combination of myricetin with oxacillin and vancomycin against methicillin resistant S. aureus (MRSA) and vancomycin intermediate resistant S. aureus (VISA) strains. Concns. used in combination assays were detd. according to the min. inhibitory concn. (MIC) for antibacterials and to the biofilm min. inhibitory concn. (BMIC) for myricetin. Checkerboard evaluations showed redn. in MIC for antibacterials in presence of myricetin and time-kill assays confirmed the synergism for these combinations, except for VISA strain when the flavonoid was combined with vancomycin. Importantly, when myricetin was combined with oxacillin, MRSA strain became susceptible to the antibacterial. Myricetin did not reduce staphyloxanthin prodn., indicating that the oxacillin susceptibility seems not to be related to this step of functional membrane microdomains. In vivo evaluations using Galleria mellonella confirmed the efficacy of oxacillin plus myricetin in treatment of MRSA infected-larvae when compared to the control groups, increasing in 20% host survival. The present work points out the potential of antibacterial and antivirulence compds. combinations as new alternative to control infections by multidrug resistant-bacteria.
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    Recent advances in understanding the antibacterial properties of flavonoids
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    A review. Antibiotic resistance is a major global problem and there is a pressing need to develop new therapeutic agents. Flavonoids are a family of plant-derived compds. with potentially exploitable activities, including direct antibacterial activity, synergism with antibiotics, and suppression of bacterial virulence. In this review, recent advances towards understanding these properties are described. Information is presented on the ten most potently antibacterial flavonoids as well as the five most synergistic flavonoid-antibiotic combinations tested in the last 6 years (identified from PubMed and ScienceDirect). Top of these resp. lists are panduratin A, with min. inhibitory concns. (MICs) of 0.06-2.0 μg/mL against Staphylococcus aureus, and epicatechin gallate, which reduces oxacillin MICs as much as 512-fold. Research seeking to improve such activity and understand structure-activity relationships is discussed. Proposed mechanisms of action are also discussed. In addn. to direct and synergistic activities, flavonoids inhibit a no. of bacterial virulence factors, including quorum-sensing signal receptors, enzymes and toxins. Evidence of these mol. effects at the cellular level include in vitro inhibition of biofilm formation, inhibition of bacterial attachment to host ligands, and neutralization of toxicity towards cultured human cells. In vivo evidence of disruption of bacterial pathogenesis includes demonstrated efficacy against Helicobacter pylori infection and S. aureus α-toxin intoxication.
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    Tchoumtchoua, J.; Mathiron, D.; Pontarin, N.; Gagneul, D.; van Bohemen, A. I.; Otogo N’nang, E.; Mesnard, F.; Petit, E.; Fontaine, J. X.; Molinié, R.; Quéro, A. Phenolic Profiling of Flax Highlights Contrasting Patterns in Winter and Spring Varieties. Molecules 2019, 24, 4303– 14,  DOI: 10.3390/molecules24234303
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    Phenolic profiling of flax highlights contrasting patterns in winter and spring varieties
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    Molecules (2019), 24 (23), 4303CODEN: MOLEFW; ISSN:1420-3049. (MDPI AG)
    Flax (Linum usitatissimum) is a plant grown in temperate regions either for its fiber or for its seeds, which are rich in the essential fatty acid omega-3. It is also well known as a source of medicinal compds. The chem. compn. of its leaves is currently poorly described. In order to fill this gap, we have conducted a comprehensive anal. of flax leaf metabolome. The exploration of the metabolome allowed the characterization of compds. isolated for the first time in flax leaves. These mols. were isolated by preparative HPLC and then characterized by NMR, LC-MS and std. anal. This work extended our picture of C-glycosyl-flavonoids and coniferyl alc. derivs. accumulated in flax. The follow-up of the content of these different metabolites via UPLC-MS revealed significant accumulation differences in spring and winter flax leaves. In particular, two methylated C-glycosylflavonoids (swertisin and swertiajaponin) were the most abundant phenolic compds. in winter flax whereas they were not detected in spring flax. This result suggests that these 2 compds. are involved in cold stress tolerance in flax.
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  • Abstract

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    Figure 1

    Figure 1. TLC plates of the four fractions obtained from T. bergeri. Mobile phase: chloroform/methanol (90/10). (A) UV 254 nm. (B) UV 365 nm. (C) Sulfuric vanillin. (D) Neu’s reagent. (E) Anisaldehyde. 1 and 2 represent compounds 1 and 2, respectively.

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    Figure 2

    Figure 2. MSE (high-energy) and MS/MS spectra of compound 1 isolated from the dichloromethane fraction (F2) of T. bergeri. (A) MSE mass spectrum obtained in the negative mode. (B) MSE mass spectrum obtained in the positive mode. (C) MS/MS spectrum in the negative mode with a collision energy of 18 eV. (D) MS/MS spectrum in the positive mode with a collision energy of 28 eV.

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    Figure 3

    Figure 3. MSE (high-energy) and MS/MS spectra of compound 2 isolated from the dichloromethane fraction (F2) of T. bergeri. (A) MSE mass spectrum obtained in the negative mode. (B) MSE mass spectrum obtained in the positive mode. (C) MS/MS mass spectrum in the negative mode with a collision energy of 18 eV. (D) MS/MS mass spectrum in the positive mode with a collision energy of 28 eV.

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    Figure 4

    Figure 4. Chemical structures of (A) penduletin (compound 1) and (B) viscosine (compound 2).

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  • References

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      A review. Cancer is one of the most leading causes of death worldwide. It is one of the primary global diseases that cause morbidity and mortality in millions of people. It is usually caused by different carcinogenic agents that damage the genetic material and alter the cell signaling pathways. Carcinogens are classified into two groups as genotoxic and non-genotoxic agents. Genotoxic carcinogens are capable of directly altering the genetic material, while the non-genotoxic carcinogens are capable of producing cancer by some secondary mechanisms not related to direct gene damage. There is undoubtedly the greatest need to utilize some novel natural products as anticancer agents, as these are within reach everywhere. Interventions by some natural products aimed at decreasing the levels and conditions of these risk factors can reduce the frequency of cancer incidences. Cancer is conventionally treated by surgery, radiation therapy and chemotherapy, but such treatments may be fast-acting and causes adverse effects on normal tissues. Alternative and innovative methods of cancer treatment with the least side effects and improved efficiency are being encouraged. In this review, we discuss the different risk factors of cancer development, conventional and innovative strategies of its management and provide a brief review of the most recognized natural products used as anticancer agents globally.
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      Guglielmi, P.; Pontecorvi, V.; Rotondi, G. Natural Compounds and Extracts as Novel Antimicrobial Agents. Expert Opin. Ther. Pat. 2020, 30, 949– 962,  DOI: 10.1080/13543776.2020.1853101
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      Natural compounds and extracts as novel antimicrobial agents
      Guglielmi, Paolo; Pontecorvi, Virginia; Rotondi, Giulia
      Expert Opinion on Therapeutic Patents (2020), 30 (12), 949-962CODEN: EOTPEG; ISSN:1354-3776. (Taylor & Francis Ltd.)
      A review. Antimicrobial resistance is a worldwide problem accounting for the redn. or in some cases absence of drugs effectiveness normally used in infections treatment. In the light of the even more spread ability of microbials to develop resistance, there is an urgent necessity to find novel and alternative routes to fight infections. Natural compds. or exts. can be a valid alternative either as monotherapy or as adjuvant in order to improve the effectiveness of the failing drugs.: This review provides a comprehensive update (2018-2020) on the development state of innovative antimicrobial agents based on natural compds. and exts., also describing their compns., methods of prodn. and use, mechanism of action, along with anti-microbial data when available.: Owing to the pivotal role that natural compds. often cover in the finding of novel drugs, their in-depth anal. could pave the way to the discovery of new antimicrobial agents. Most of the alternative approaches reported in this short review were validated through in vitro and in vivo (animal as well as human) models. The employment of natural derived compds. and exts., alone or in combination with classical antimicrobial drugs, as antimicrobial agents could represent an important achievement to challenge pathogens resistant mechanisms.
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      Gouda, E. J. Tillandsia BROMELIACEAE. In Monocotyledons; Eggli, U., Nyffeler, R., Eds.; Springer Berlin Heidelberg: Berlin, Heidelberg, 2020; pp 1107– 1164.
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      Aguilar-Rodríguez, P. A.; MacSwiney, G.; García-Franco, T.; Knauer, J. G.; Kessler, A.; Kessler, M. First Record of Bat-Pollination in the Species-Rich Genus Tillandsia (Bromeliaceae). Ann. Bot. 2014, 113, 1047– 1055,  DOI: 10.1093/aob/mcu031
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      First record of bat-pollination in the species-rich genus Tillandsia (Bromeliaceae)
      Aguilar-Rodriguez Pedro Adrian; MacSwiney G M Cristina; Kromer Thorsten; Garcia-Franco Jose G; Knauer Anina; Kessler Michael
      Annals of botany (2014), 113 (6), 1047-55 ISSN:.
      BACKGROUND AND AIMS: Bromeliaceae is a species-rich neotropical plant family that uses a variety of pollinators, principally vertebrates. Tillandsia is the most diverse genus, and includes more than one-third of all bromeliad species. Within this genus, the majority of species rely on diurnal pollination by hummingbirds; however, the flowers of some Tillandsia species show some characteristics typical for pollination by nocturnal animals, particularly bats and moths. In this study an examination is made of the floral and reproductive biology of the epiphytic bromeliad Tillandsia macropetala in a fragment of humid montane forest in central Veracruz, Mexico. METHODS: The reproductive system of the species, duration of anthesis, production of nectar and floral scent, as well as diurnal and nocturnal floral visitors and their effectiveness in pollination were determined. KEY RESULTS: Tillandsia macropetala is a self-compatible species that achieves a higher fruit production through outcrossing. Nectar production is restricted to the night, and only nocturnal visits result in the development of fruits. The most frequent visitor (75 % of visits) and the only pollinator of this bromeliad (in 96 % of visits) was the nectarivorous bat Anoura geoffroyi (Phyllostomidae: Glossophaginae). CONCLUSIONS: This is the first report of chiropterophily within the genus Tillandsia. The results on the pollination biology of this bromeliad suggest an ongoing evolutionary switch from pollination by birds or moths to bats.
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      Manetti, L. M.; Delaporte, R. H.; Laverde, A., Jr. Metabólitos secundários da família bromeliaceae. Quim. Nova 2009, 32, 1885– 1897,  DOI: 10.1590/s0100-40422009000700035
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      Secondary metabolites from Bromeliaceae family
      Manetti, Liliana Maria; Delaporte, Rosemeres Horwat; Laverde, Antonio, Jr.
      Quimica Nova (2009), 32 (7), 1885-1897CODEN: QUNODK; ISSN:0100-4042. (Sociedade Brasileira de Quimica)
      This review describes aspects of the Bromeliaceae family dealing the traditional applications, biol. activities and distribution of secondary metabolites in distinct subfamilies. Some species are used with medicinal purposed in the treatment of respiratory, diabetes or inflammation diseases, and gastrointestinal disorders. Special emphasis on cycloartane triterpenoids and flavonoids, typical metabolites of this family, are presented. Bromeliaceae is unique amongst the monocotyledons in the frequency and variety of flavonoids with hydroxylation or methoxylation at the 6-position. Other compd. classes as steroids, hidroxycinnamic acids, phenylpropane diglycerides, lignans, are presented.
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      Estrella-Parra, E.; Flores-Cruz, M.; Blancas-Flores, G.; Koch, S. D.; Alarcón-Aguilar, F. J. The Tillandsia Genus: History, Uses, Chemistry, and Biological Activ. Bol. Latinoam. Caribe Plant. Med. Aromat. 2019, 18, 239– 264
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      The Tillandsia genus: history, uses, chemistry, and biological activity
      Estrella-Parra, Edgar; Flores-Cruz, Maria; Blancas-Flores, Gerardo; Koch, Stephen D.; Alarcon-Aguilar, Francisco J.
      Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromaticas (2019), 18 (3), 239-264CODEN: BLCPBA; ISSN:0717-7917. (Sociedad Latinoamericana de Fitoquimica)
      Tillandsia L. genus comprises 649 species, with different uses at different times. T. usneoides L. uses are reported since the late-archaic and pre-Columbian cultures. In XIX-XX centuries, T. usneoides was used in some manufd. products, as polish and packing fruit. Tillandsia has a favorable reputation as medicine: for leucorrhea, rheumatism, ulcers, hemorrhoid treatment, as an anti-diabetic remedy, emetic, analgesic, purgative, contraceptive, antispasmodic and diuretic. Tillandsia chem. compn. includes cycloartane triterpenes and hydroxy-flavonoids, which are present in at least 24 species. Several exts. and compds. from Tillandsia spp. have been reported with pharmacol. actions, as anti-neoplasia, hypolipidemic, antifungal, anti-HSV-1, hypoglycemic and microbicide. This review communicates the economic importance, ethnobotany, chem. compn. and biol. activities of the Tillandsia genus, and analyze its biol. and economic perspective. Tillandsia genus has cultural, economic and pharmacol. relevance, with a high potential in many essential aspects of the modern society.
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      Choma, I. M.; Grzelak, E. M. Bioautography Detection in Thin-Layer Chromatography. J. Chromatogr. A 2011, 1218, 2684– 2691,  DOI: 10.1016/j.chroma.2010.12.069
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      Bioautography detection in thin-layer chromatography
      Choma, Irena M.; Grzelak, Edyta M.
      Journal of Chromatography A (2011), 1218 (19), 2684-2691CODEN: JCRAEY; ISSN:0021-9673. (Elsevier B.V.)
      A review. Bioautog. is a microbial detection method hyphenated with planar chromatog. techniques. It is based mainly on antimicrobial or antifungal properties of analyzed substances. The review discusses three versions of bioautog., i.e. contact, immersion and direct bioautog. The more concern is given to the last one. Many applications are quoted, not only for testing various groups of compds., but also for investigating biochem. processes and factors influencing bacterial growth. Addnl., related methods, which can be included into direct bioautog., are discussed. The most promising among them seems to be TLC-bioluminescence screening.
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      Goodall, R. R.; Levi, A. A. A Microchromatographic Method for the Detection and Approximate Determination of the Different Penicillins in a Mixture. Nature 1946, 158, 675– 676,  DOI: 10.1038/158675a0
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      A microchromatographic method for the detection and approximate determination of the different penicillins in a mixture
      GOODALL R R; LEVI A A
      Nature (1946), 158 (4019), 675 ISSN:0028-0836.
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      Jesionek, W.; Majer-Dziedzic, B.; Choma, I. M. Separation, Identification, and Investigation of Antioxidant Ability of Plant Extract Components Using TLC, LC-MS, and TLC-DPPH. J. Liq. Chromatogr. Relat. Technol. 2015, 38, 1147– 1153,  DOI: 10.1080/10826076.2015.1028295
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      Separation, Identification, and Investigation of Antioxidant Ability of Plant Extract Components Using TLC, LC-MS, and TLC-DPPH•
      Jesionek, Wioleta; Majer-Dziedzic, Barbara; Choma, Irena Maria
      Journal of Liquid Chromatography & Related Technologies (2015), 38 (11), 1147-1153CODEN: JLCTFC; ISSN:1082-6076. (Taylor & Francis, Inc.)
      Ten common phenolic compds. from the exts. of five plant species, i.e., Hypericum perforatum L., Matricaria recutita L., Achillea millefolium L., Thymus vulgaris L., and Salvia officinalis L., were sepd. using optimized thin-layer chromatog. (TLC) conditions at normal phase mode and were visualized using Natural Product/Polyethylene Glycol Reagent. Antioxidant properties of components of the exts. were assessed using TLC-DPPH• directly on the TLC plate. Nine out of ten analyzed polyphenols were proved to be radical scavengers. The presence and identity of target substances in plant samples were confirmed by the liq. chromatog.-mass spectrometry technique.
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      Choma, I.; Jesionek, W. TLC-Direct Bioautography as a High Throughput Method for Detection of Antimicrobials in Plants. Chromatography 2015, 2, 225– 238,  DOI: 10.3390/chromatography2020225
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      TLC-direct bioautography as a high throughput method for detection of antimicrobials in plants
      Choma, Irena M.; Jesionek, Wioleta
      Chromatography (2015), 2 (2), 225-238CODEN: CHROBV; ISSN:2227-9075. (MDPI AG)
      The richness of bioactive compds. in plant materials encourages continuous development of sepn. methods and bioassays for their isolation and identification. Thin-layer chromatog.-direct bioautog. links sepn. on the adsorbent layer with biol. tests performed directly on it. Therefore, the method is very convenient for searching plant constituents with biol. activity, such as antibiotics. Test bacteria grow directly on a plate surface excluding places where antibacterials are located. They can be detected with reagents converted by living bacteria. TLC-DB is a high throughput method enabling analyses of many samples in parallel and the comparison of their activity. Both screening and semi-quant. anal. is possible. The targeted compds. can be identified using spectroscopic methods, mostly mass spectrometry, that can be performed directly on a TLC plate. This paper discusses all above mentioned aspects of TLC-DB, illustrating them with literature, schemes and our own results.
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      Dewanjee, S.; Gangopadhyay, M.; Bhattacharya, N.; Khanra, R.; Dua, T. K. Bioautography and Its Scope in the Field of Natural Product Chemistry. J. Pharm. Anal. 2015, 5, 75– 84,  DOI: 10.1016/j.jpha.2014.06.002
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      Bioautography and its scope in the field of natural product chemistry
      Dewanjee Saikat; Bhattacharya Niloy; Khanra Ritu; Dua Tarun K; Gangopadhyay Moumita
      Journal of pharmaceutical analysis (2015), 5 (2), 75-84 ISSN:2095-1779.
      Medicinal plants, vegetables and fruits are the sources of huge number of bioactive lead/scaffolds with therapeutic and nutraceutical importance. Bioautography is a means of target-directed isolation of active molecules on chromatogram. Organic solvents employed in chromatographic separation process can be completely removed before biological detection because these solvents cause inactivation of enzymes and/or death of living organisms. They offer a rapid and easy identification of bioactive lead/scaffolds in complex matrices of plant extracts. Bioautography is a technique to isolate hit(s)/lead(s) by employing a suitable chromatographic process followed by a biological detection system. This review critically describes the methodologies to identify antimicrobial, antioxidant, enzyme inhibitor lead/scaffolds by employing bioautography. A significant number of examples have been incorporated to authenticate the methodologies.
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      Choma, I.; Jesionek, W. Effects-Directed Biological Detection. In Instrumental Thin-Layer Chromatography; Poole, C. F., Ed.; Elsevier: Detroit, MI, USA, 2015; pp 279– 312.
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      Rahalison, L.; Hamburger, M.; Hostettmann, K.; Monod, M.; Frenk, E. A Bioautographic Agar Overlay Method for the Detection of Antifungal Compounds from Higher Plants. Phytochem. Anal. 1991, 2, 199– 203,  DOI: 10.1002/pca.2800020503
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      A bioautographic agar overlay method for the detection of antifungal compounds from higher plants
      Rahalison, L.; Hamburger, M.; Hostettmann, K.; Monod, M.; Frenk, E.
      Phytochemical Analysis (1991), 2 (5), 199-203CODEN: PHANEL; ISSN:0958-0344.
      A simple bioautog. agar overlay assay using Candida abicans as the indicator organism for the detection and activity-guided fractionation of antifungal compds. by thin layer chromatog. has been developed. Inhibition of fungal growth was assessed by the detection of dehydrogenase activity with thiazolyl blue (methylthiazolyltetrazolium chloride; MTT). A series of clin. used antimycotic agents were tested in order to det. the sensitivity of the assay. The compatibility of the agar overlay technique with chem. modified silica gel (Diol and RP-18) plates and with various org. solvents was evaluated. The methodol. is also applicable to the search for antibacterial compds., as shown with Bacillus subtilis as a test organism.
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      Nuthan, B. R.; Rakshith, D.; Marulasiddaswamy, K. M.; Rao, H. C. Y.; Ramesha, K. P.; Mohana, N. C.; Siddappa, S.; Darshan, D.; Kumara, K. K. S.; Satish, S. Application of Optimized and Validated Agar Overlay TLC-Bioautography Assay for Detecting the Antimicrobial Metabolites of Pharmaceutical Interest. J. Chromatogr. Sci. 2020, 58, 737– 746,  DOI: 10.1093/chromsci/bmaa045
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      Application of optimized and validated agar overlay TLC-bioautography assay for detecting the antimicrobial metabolites of pharmaceutical interest
      Nuthan, Bettadapura Rameshgowda; Rakshith, Devaraju; Marulasiddaswamy, Kuppuru Mallikarjunaiah; Rao, H. C. Yashavantha; Ramesha, Kolathur Puttamadaiah; Mohana, Nagabhushana Chandra; Siddappa, Shiva; Darshan, Doreraj; Kumara, Kigga Kaadappa Sampath; Satish, Sreedharamurthy
      Journal of Chromatographic Science (2020), 58 (8), 737-746CODEN: JCHSBZ; ISSN:1945-239X. (Oxford University Press)
      The agar overlay TLC-bioautog. is one of the crucial methods for simultaneous in situ detection and sepn. of antimicrobial metabolites of pharmaceutical interest. The main focus of this research relies on the dereplication of an antimicrobial metabolite coriloxin derived from mycoendophytic Xylaria sp. NBRTSB-20 with a validation of agar overlay TLC-bioautog. technique. This polyketide metabolite coriloxin was purified by column chromatog., and its purity was assessed by HPLC, UPLC-ESI-QTOF-MS, FT-IR and NMR spectral anal. The antimicrobial capability of Et acetate ext. and the purified compd. coriloxin was detd. by disk diffusion, minimal inhibitory concn. and agar overlay TLC-bioautog. assay. The visible LOD of coriloxin antimicrobial activity was found at 10μg for Escherichia coli and 20μg for both Staphylococcus aureus and Fusarium oxysporum. Inter- and intra-day precision was detd. as the relative std. deviation is less than 6.56%, which proved that this method was precise. The accuracy was expressed as recovery, and the values were found ranging from 91.18 to 108.73% with RSD values 0.94-2.30%, resp. The overall findings of this investigation suggest that agar overlay TLC-bioautog. assay is a suitable and acceptable method for the in situ detn. of antimicrobial pharmaceuticals.
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      Grela, E.; Kozłowska, J.; Grabowiecka, A. Current methodology of MTT assay in bacteria - A review. Acta Histochem. 2018, 120, 303– 311,  DOI: 10.1016/j.acthis.2018.03.007
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      Current methodology of MTT assay in bacteria - A review
      Grela, Ewa; Kozlowska, Joanna; Grabowiecka, Agnieszka
      Acta Histochemica (2018), 120 (4), 303-311CODEN: AHISA9; ISSN:0065-1281. (Elsevier GmbH)
      A review. The MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) tetrazolium assay is a popular tool in estg. the metabolic activity of living cells. The test is based on enzymic redn. of the lightly colored tetrazolium salt to its formazan of intense purple-blue color, which can be quantified spectrophotometrically. Under properly optimized conditions the obtained absorbance value is directly proportional to the no. of living cells. Originally, the MTT assay was devised for use in eukaryotic cells lines and later applied for bacteria and fungi. As the mechanism of MTT redn. was studied in detail mostly considering eukaryotic cells, the lack of information resulted in generating a vast variety of MTT based protocols for bacterial enzymic activity evaluation. In the presented article the main aspects of the MTT assay applicability in bacterial research were summarized, with special emphasis on sources of inaccuracies and misinterpretation of the test results.
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      Marston, A. Thin-Layer Chromatography with Biological Detection in Phytochemistry. J. Chromatogr. A 2011, 1218, 2676– 2683,  DOI: 10.1016/j.chroma.2010.12.068
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      Thin-layer chromatography with biological detection in phytochemistry
      Marston, A.
      Journal of Chromatography A (2011), 1218 (19), 2676-2683CODEN: JCRAEY; ISSN:0021-9673. (Elsevier B.V.)
      A review. Bioautog. on thin-layer chromatog. (TLC) plates is a means of detecting the biol. activity of a sample which has migrated on the plate with a suitable solvent. It only requires small amts. of sample and is ideal for the investigation of plant constituents, which often occur as complex mixts. It can be used for the target-directed isolation of these constituents. In contrast to HPLC, many samples can be run at the same time on TLC. Org. solvents, which cause inactivation of enzymes or death of living organisms, can be completely removed before biol. detection. Many bioassays are compatible with TLC. Antimicrobial, radical scavenging, antioxidant activities and enzyme inhibition feature among the tests that are employed.
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      Horváth, G.; Jámbor, N.; Végh, A.; Böszörményi, A.; Lemberkovics, É.; Héthelyi, É.; Kovács, K.; Kocsis, B. Antimicrobial Activity of Essential Oils: The Possibilities of TLC-Bioautography. Flavour Fragrance J. 2010, 25, 178– 182,  DOI: 10.1002/ffj.1993
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      Antimicrobial activity of essential oils: the possibilities of TLC-bioautography
      Horvath, Gyorgyi; Jambor, Noemi; Vegh, Anna; Boszormenyi, Andrea; Lemberkovics, Eva; Hethelyi, Eva; Kovacs, Krisztina; Kocsis, Bela
      Flavour and Fragrance Journal (2010), 25 (3), 178-182CODEN: FFJOED; ISSN:0882-5734. (John Wiley & Sons Ltd.)
      Essential oils are well-known for their antimicrobial activity against different plant and human pathogenic microorganisms. The results of the most commonly used antimicrobial assays are very different; sometimes their reliability is questionable, therefore standardized methods need to be used to solve this problem. The present study aims at the phytochem. characterization of some essential oils (thyme, lavender, eucalyptus, spearmint and cinnamon) that are important from the therapeutic and economic aspects and the optimized microbiol. investigation of the effect of essential oils on human and plant pathogenic microorganisms. The chem. compn. of the essential oils was analyzed with thin-layer chromatog. (TLC) and their compn. was controlled by gas chromatog. (GC). The antibacterial effect was investigated using the TLC-bioautog. method. The solvents applied in TLC developing systems were also tested. Our results showed that toluene, Et acetate, ethanol and chloroform as solvents used in the assay had no inhibiting effect on the test bacteria. The antibacterial activity of thyme, lavender and cinnamon oils and their main components (thymol, carvacrol, linalool, eugenol) was obsd. in the case of two plant pathogenic bacteria (Xanthomonas campestris pv. vesicatoria and Pseudomonas syringae pv. phaseolicola) and some human pathogens (Staphylococcus epidermidis, S. saprophyticus and two strains of S. aureus, including one methicillin-resistant strain). On the whole, the antibacterial activity of essential oils can be related to their most abundant components, but the effect of the minor components should also be taken into consideration. Direct bioautog. is more cost-effective and compares better with traditional microbiol. lab. methods (e.g. disk-diffusion, agar-plate technique).
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    30. 30
      Mühlebach, A.; Adam, J.; Schön, U. Streamlined Approach to High-Quality Purification and Identification of Compound Series Using High-Resolution MS and NMR. J. Sep. Sci. 2011, 34, 2983– 2988,  DOI: 10.1002/jssc.201100382
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      30
      Streamlined approach to high-quality purification and identification of compound series using high-resolution MS and NMR
      Muehlebach, Anneke; Adam, Joachim; Schoen, Uwe
      Journal of Separation Science (2011), 34 (21), 2983-2988CODEN: JSSCCJ; ISSN:1615-9306. (Wiley-VCH Verlag GmbH & Co. KGaA)
      Automated medicinal chem. (parallel chem.) has become an integral part of the drug-discovery process in almost every large pharmaceutical company. Parallel array synthesis of individual org. compds. has been used extensively to generate diverse structural libraries to support different phases of the drug-discovery process, such as hit-to-lead, lead finding, or lead optimization. In order to guarantee effective project support, efficiency in the prodn. of compd. libraries has been maximized. As a consequence, also throughput in chromatog. purifn. and anal. has been adapted. As a recent trend, more labs. are prepg. smaller, yet more focused libraries with even increasing demands towards quality, i.e. optimal purity and unambiguous confirmation of identity. This paper presents an automated approach how to combine effective purifn. and structural conformation of a lead optimization library created by microwave-assisted org. synthesis. The results of complementary anal. techniques such as UHPLC-HRMS and NMR are not only regarded but even merged for fast and easy decision making, providing optimal quality of compd. stock. In comparison with the previous procedures, throughput times are at least four times faster, while compd. consumption could be decreased more than threefold.
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    31. 31
      Lowe, H.; Watson, C. T.; Badal, S.; Ateh, E. N.; Toyang, N. J.; Bryant, J. Anti-Angiogenic Properties of the Jamaican Ball Moss, (Tillandsia Recurvata L.). Int. Res. J. Biol. Sci. 2012, 1, 73– 76
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      Andrighetti-Fröhner, C. R.; Sincero, T. C. M.; da Silva, A. C.; Savi, L. A.; Gaido, C. M.; Bettega, J. M. R.; Mancini, M.; de Almeida, M. T. R.; Barbosa, R. A.; Farias, M. R.; Barardi, C. R. M.; Simões, C. M. O. Antiviral Evaluation of Plants from Brazilian Atlantic Tropical Forest. Fitoterapia 2005, 76, 374– 378,  DOI: 10.1016/j.fitote.2005.03.010
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      Antiviral evaluation of plants from Brazilian Atlantic Tropical Forest
      Andrighetti-Frohner C R; Sincero T C M; da Silva A C; Savi L A; Gaido C M; Bettega J M R; Mancini M; de Almeida M T R; Barbosa R A; Farias M R; Barardi C R M; Simoes C M O
      Fitoterapia (2005), 76 (3-4), 374-8 ISSN:0367-326X.
      The antiviral activity of six medicinal plants from Brazilian Atlantic Tropical Forest was investigated against two viruses: herpes simplex virus type 1 (HSV-1) and poliovirus type 2 (PV-2). Cuphea carthagenensis and Tillandsia usneoides extracts showed the best antiherpes activity. T. usneoides dichloromethane, ethyl acetate and n-butanol extracts, and Lippia alba n-butanol extract showed inhibition of HSV-1, strain 29R/acyclovir resistant. In addition, only L. alba ethyl acetate extract showed antipoliovirus activity. These results corroborate that medicinal plants can be a rich source of potential antiviral compounds.
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    33. 33
      Vieira, B. M.; Kaplan, M. A. C. Tillandsia Usneoides (L.) L. (Bromeliaceae): Aspectos Químicos e Farmacológicos;Rev. Fitos, 2011; Vol. 6, pp 2009– 2012.
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      Witherup, K. M.; McLaughlin, J. L.; Judd, R. L.; Ziegler, M. H.; Medon, P. J.; Keller, W. J. Identification of 3-Hydroxy-3-Methylglutaric Acid (HMG) as a Hypoglycemic Principle of Spanish Moss (TillandsiaUsneoides). J. Nat. Prod. 1995, 58, 1285– 1290,  DOI: 10.1021/np50122a023
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      Identification of 3-hydroxy-3-methylglutaric acid (HMG) as a hypoglycemic principle of Spanish moss (Tillandsia usneoides)
      Witherup, K. M.; McLaughlin, J. L.; Judd, R. L.; Ziegler, M. H.; Medon, P. J.; Keller, W. J.
      Journal of Natural Products (1995), 58 (8), 1285-90CODEN: JNPRDF; ISSN:0163-3864. (American Society of Pharmacognosy)
      Bioactivity-directed fractionation, using brine shrimp lethality and murine hypoglycemia, of an ethanol ext. prepd. from Tillandsia usneoides, led to the isolation of four apparently bioactive compds. from the water-sol. fraction. The compds. were identified as citric acid, succinic acid, 3-hydroxy-3-methylglutaric acid (HMG), and 3,6,3',5'-tetramethoxy-5,7,4'-trihydroxyflavone-7-O-β-D-glucoside. The brine shrimp lethality of the acids was simply due to acidity; however, HMG elicited significant hypoglycemic responses in fasting normal mice. Et and Me esters of citric acid were prepd. and tested in the murine hypoglycemic assay. Five of the predominant sugars were identified by TLC. Free thymidine was also isolated. Further evaluation of HMG and other potential inhibitors of HMG CoA lyase, in the treatment of symptoms of diabetes mellitus, is suggested.
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      Lowe, H.; Toyang, N.; Bryant, J. In vitro and in vivo anti-cancer effects of tillandsia recurvata (ball moss) from Jamaica. W. Indian Med. J. 2013, 62, 177– 80
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      Lowe, H. I. C.; Toyang, N. J.; Watson, C. T.; Badal, S.; Bahado-Singh, P.; Bryant, J. In Vitro Anticancer Activity of the Crude Extract and two Dicinnamate Isolates from the Jamaican Ball Moss (Tillandsia Recurvata L.). Am. Int. J. Contemp. Res. 2013, 3, 93– 96
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      In Vitro Anticancer Activity of the Crude Extract and two Dicinnamate Isolates from the Jamaican Ball Moss (Tillandsia Recurvata L.)
      Lowe Henry Ic; Toyang Ngeh J; Watson Charah; Badal Simone; Bahado-Singh Perceval; Bryant Joseph
      American international journal of contemporary research (2013), 3 (1), 93-96 ISSN:2162-139X.
      A crude chloroform extract from the Jamaican Ball Moss (Tillandsia recurvata L.) was tested for activity against three human cancer cell lines including; A375 (human melanoma), MCF-7 (human breast) and PC-3 (human prostate cancer) using the WST-1 assay. IC50s obtained against these cell lines; A375, MCF-7 and PC-3 in the presence of the crude extract are; 0.9μg/ml, 40.51μg/ml and 5.97μg/ml respectively indicating the promising anti-cancer activity of the ball moss extract. Further, preliminary phytochemical study was conducted in an attempt to identify and isolate the phytochemicals that could possibly be responsible for the observed bioactivity of the ball moss chloroform extract. As a result, two dicinnamates were isolated; 1,3-di-O-Cinnamoyl-glycerol (1) and (E)-3-(cinnamoyloxy)-2-hydroxypropyl 3-(3,4-dimethoxyphenyl)acrylate (2) and we report for the first time isolation of compound 2. Even though the bioactivity of these two islaotes were fairly weak against the cell lines, the results presented here will prove useful for further research aimed at identifying molecules that maybe effective against melanoma, breast and prostate cancers associated with fewer side-effects.
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    37. 37
      Lowe, H. I. C.; Watson, C. T.; Badal, S.; Toyang, N. J.; Bryant, J. Cycloartane-3,24,25-triol inhibits MRCKα kinase and demonstrates promising anti prostate cancer activity in vitro. Cancer Cell Int. 2012, 12, 46,  DOI: 10.1186/1475-2867-12-46
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      Cycloartane-3,24,25-triol inhibits MRCKα kinase and demonstrates promising anti prostate cancer activity in vitro
      Lowe, Henry I. C.; Watson, Charah T.; Badal, Simone; Toyang, Ngeh J.; Bryant, Joseph
      Cancer Cell International (2012), 12 (), 46CODEN: CCIACC; ISSN:1475-2867. (BioMed Central Ltd.)
      Background: Given the high occurrence of prostate cancer worldwide and one of the major sources of the discovery of new lead mols. being medicinal plants, this research undertook to investigate the possible anti-cancer activity of two natural cycloartanes; cycloartane-3,24,25-diol (extd. in our lab from Tillandsia recurvata) and cycloartane-3,24,25-triol (purchased). The inhibition of MRCKα kinase has emerged as a potential soln. to restoring the tight regulation of normal cellular growth, the loss of which leads to cancer cell formation. Methods: Kinase inhibition was investigated using competition binding (to the ATP sites) assays which have been previously established and authenticated and cell proliferation was measured using the WST-1 assay. Results: Cycloartane-3,24,25-triol demonstrated strong selectivity towards the MRCKα kinase with a Kd50 of 0.26 μM from a total of 451 kinases investigated. Cycloartane-3,24,25-triol reduced the viability of PC-3 and DU145 cell lines with IC50 values of 2.226 ± 0.28 μM and 1.67 ± 0.18 μM resp. Conclusions: These results will prove useful in drug discovery as Cycloartane-3,24,25-triol has shown potential for development as an anti-cancer agent against prostate cancer.
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      Lowe, H. I. C.; Toyang, N. J.; Watson, C. T.; Ayeah, K. N. N.; Bryant, J. Antileukemic Activity of Tillandsia Recurvata and Some of Its Cycloartanes. Anticancer Res. 2014, 34, 3505– 3509
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      Antileukemic activity of Tillandsia recurvata and some of its cycloartanes
      Lowe, Henry I. C.; Toyang, Ngeh J.; Watson, Charah T.; Ayeah, Kenneth N. N.; Bryant, Joseph
      Anticancer Research (2014), 34 (7), 3505-3509CODEN: ANTRD4; ISSN:0250-7005. (International Institute of Anticancer Research)
      Background: Approx. 250,000 deaths were caused by leukemia globally in 2012 and about 40%-50% of all leukemia diagnoses end-up in death. Medicinal plants are a rich source for the discovery of new drugs against leukemia and other types of cancers. To this end, we subjected the Jamaican ball moss (Tillandsia recurvata) and its cycloartanes, as well as some analogs, to in vitro screening against a no. of leukemia cell lines. The WST-1 anti-proliferation assay was used to det. the anticancer activity of ball moss and two cycloartanes isolated from ball moss and four of their analogs against four leukemia cell lines (HL-60, K562, MOLM-14, monoMac6). Ball moss crude methanolic ext. showed activity with a 50% inhibition concn. (IC50) value of 3.028 μg/mL against the Molm-14 cell line but was ineffective against HL-60 cells. The six cycloartanes tested demonstrated varying activity against the four leukemia cancer cell lines with IC50 values ranging from 1.83 μM to 18.3 μM. Five out of the six cycloartanes demonstrated activity, while one was inactive against all four cell lines. The preliminary activity demonstrated by the Jamaican ball moss and its cycloartanes against selected leukemia cell lines continues to throw light on the broad anticancer activity of ball moss. Further studies to evaluate the efficacy of these mols. in other leukemia cell lines are required in order to validate the activity of these mols., as well as to det. their mechanisms of action and ascertain the activity in vivo in order to establish efficacy and safety profiles.
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      Lowe, H. I. C.; Toyang, N. J.; Watson, C. T.; Ayeah, K. N.; Bryant, J. HLBT-100: A Highly Potent Anti-Cancer Flavanone from Tillandsia Recurvata (L.) L. Cancer Cell Int. 2017, 17, 1– 12,  DOI: 10.1186/s12935-017-0404-z
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      Weld, J. T. The Antibiotic Action of TillandsiaUsneoides (Spanish Moss). Exp. Biol. Med. 1945, 59, 40– 41,  DOI: 10.3181/00379727-59-14972P
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      Antibiotic action of Tillandsia usneoides (Spanish moss)
      Weld, Julia T.
      Proceedings of the Society for Experimental Biology and Medicine (1945), 59 (), 40-1CODEN: PSEBAA; ISSN:0037-9727.
      Preliminary. A method for extg. an antibiotic substance from the brown portions of the plant is described. The crude ext. is effective against all gram-pos. bacteria tested and against Cryptococcus hominis, but has no inhibitory effect on growth of H. influenzae A, Ps. pyocyaneus, E. coli, and B. proteus.
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      Webber, M. G.; Lauter, W. M.; Foote, P. A. A Preliminary Phytochemical Study of TillandsiaUsneoides L. (Spanish Moss). J. Am. Pharm. Assoc. Sci. Ed. 1952, 41, 230– 235,  DOI: 10.1002/jps.3030410503
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      Paz, E. A.; Cerdeiras, M. P.; Fernandez, J.; Ferreira, F.; Moyna, P.; Soubes, M.; Vázquez, A.; Vero, S.; Zunino, L. Screening of Uruguayan Medicinal Plants for Antimicrobial Activity. J. Ethnopharmacol. 1995, 45, 67– 70,  DOI: 10.1016/0378-8741(94)01192-3
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      Faller, E. M.; Zajmi, A.; Kanes, S. N. In Vitro Antibacterial Activity of Spanish Moss (Tillandsia usneoides) Crude Extract Against Skin Infection in Wound Healing. Int. J. Pharmacogn. Phytochem. Res. 2017, 9, 1344– 1352,  DOI: 10.25258/phyto.v9i10.10459
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      Zheng, L.; Chen, H.; Han, X.; Lin, W.; Yan, X. Antimicrobial Screening and Active Compound Isolation from Marine Bacterium NJ6-3-1 Associated with the Sponge Hymeniacidon Perleve. World J. Microbiol. Biotechnol. 2005, 21, 201– 206,  DOI: 10.1007/s11274-004-3318-6
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      Antimicrobial screening and active compound isolation from marine bacterium NJ6-3-1 associated with the sponge Hymeniacidon perleve
      Zheng, Li; Chen, Haimin; Han, Xiaotian; Lin, Wei; Yan, Xiaojun
      World Journal of Microbiology & Biotechnology (2005), 21 (2), 201-206CODEN: WJMBEY; ISSN:0959-3993. (Springer)
      Twenty-nine marine bacterial strains were isolated from the sponge Hymeniacidon perleve at Nanji island, and antimicrobial screening showed that eight strains inhibited the growth of terrestrial microorganisms. The strain NJ6-3-1 with wide antimicrobial spectrum was identified as Pseudoalteromonas piscicida based on its 16S rRNA sequence anal. The major antimicrobial metabolite, isolated through bioassay-guide fractionation of TLC bioautog. overlay assay, was identified as norharman (I) (a beta-carboline alkaloid) by EI-MS and NMR.
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      Wang, M.; Zhang, Y.; Wang, R.; Wang, Z.; Yang, B.; Kuang, H. An Evolving Technology That Integrates Classical Methods with Continuous Technological Developments: Thin-Layer Chromatography Bioautography. Molecules 2021, 26, 4647,  DOI: 10.3390/molecules26154647
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      An Evolving Technology That Integrates Classical Methods with Continuous Technological Developments: Thin-Layer Chromatography Bioautography
      Wang, Meng; Zhang, Yirong; Wang, Ruijie; Wang, Zhibin; Yang, Bingyou; Kuang, Haixue
      Molecules (2021), 26 (15), 4647CODEN: MOLEFW; ISSN:1420-3049. (MDPI AG)
      A review. Thin-layer chromatog. (TLC) bioautog. is an evolving technol. that integrates the sepn. and anal. technol. of TLC with biol. activity detection technol., which has shown a steep rise in popularity over the past few decades. It connects TLC with convenient, economic and intuitive features and bioautog. with high levels of sensitivity and specificity. In this study, we discuss the research progress of TLC bioautog. and then establish a definite timeline to introduce it. This review summarizes known TLC bioautog. types and practical applications for detg. antibacterial, antifungal, antitumor and antioxidant compds. and for inhibiting glucosidase, pancreatic lipase, tyrosinase and cholinesterase activity constitutes. Nowadays, esp. during the COVID-19 pandemic, it is important to identify original, natural products with anti-COVID potential compds. from Chinese traditional medicine and natural medicinal plants. We also give an account of detection techniques, including in situ and ex situ techniques; even in situ ion sources represent a major reform. Considering the current tech. innovations, we propose that the technol. will make more progress in TLC plates with higher sepn. and detection technol. with a more portable and extensive scope of application. We believe this technol. will be diffusely applied in medicine, biol., agriculture, animal husbandry, garden forestry, environmental management and other fields in the future.
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      Flores, S. E.; Herrán, J. The Structure of Pendulin and Penduletin: A New Flavonol Glucoside Isolated from Brickelia Pendula. Tetrahedron 1958, 2, 308– 315,  DOI: 10.1016/0040-4020(58)88052-7
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      Structure of pendulin and penduletin. New flavonol glucoside from Brickelia pendula
      Flores, S. E.; Herran, J.
      Tetrahedron (1958), 2 (), 308-15CODEN: TETRAB; ISSN:0040-4020.
      The glucoside pendulin (I) was hydrolyzed to give the new flavone, penduletin (ll), 4,5-dihydroxy-3,6,7-trimethoxyflavone to which 1 mole glucose is attached at the 4'-position. The Mexican plants known as Atanasia amarga have a bitter taste and are used indigenously for "stomach ailments" [Rio de la Loza, Materia Medica Mexicana, Pt I, 269 (1894)] and a member of the species Brickelia squarrosa was reported to contain a glycoside. Finely ground sun-dried B. pendula (2.8 kg.) extd. 3 times with 10 l. boiling alc. the exts. concd. in vacuo to 3 l., the viscous green mass washed 5 times with 2 l. hot hexane, and the residual yellow powder taken up in alc., the decolorized (Norit) soln. recrystd. (alc. and Me2CO-C6H14) gave 30 g. I, C24H26O12, m. 178-9°, [α]D22 -34° (C5H5N), v 3200, 1660, 1600, 1300-1180, 1090, 838, 810, 794 cm. -1, λ 212, 272, 332 mμ (ε 38,166, 23,013, 22,040), contg. 3 MeO groups, Rf 0.76 (in 4:1:5 BuOH-AcOH-H2O on Whatman No. 1 paper at 23° in 8 hrs. and visualization in ultraviolet light). I (0.5 g.) in 300 ml. 70% alc. contg. 15% HCl refluxed 6 hrs., the soln. dild. with 1 l. H2O, extd. 4 times with 200 ml. EtOAc, and the dried Na2SO4) ext. crystd. (dil. alc. and dil. Me2CO) yielded 0.3 g. II, C18H16O7, m. 216-17°, v 3100, 1600, 1300, 1180, 762 cm.-1, λ 212, 271, 341 mμ(ε 33,376, 19,231, 22,767), giving a crimson color in alc. on treatment with Na-Hg, pink color with Mg and HCl, and an intense yellow soln. in concd. H2SO4; diacetate (IIa), m. 157-8°, sapond. by boiling 1 hr. with alc. NaOH; di-Me deriv. (III), m. 152-3° (alc. and Me2CO-C6H14). II (0.5 g.) in 100 ml. alc. and 20 ml. 20% NaOH in 70% alc. treated slowly with 10 ml. Et2SO4, the mixt. refluxed 30 min., treated with 20 ml. Et2SO4, and refluxed 5 hrs. under const. const, alky., the cooled soln. dild. with 300 ml. H2O and extd. with EtOAc, the ext. evapd., and the residue crystd. (dil. alc. and Me2CO-C6H14) gave 0.31 g. 4'-ethoxy-5-hydroxy-3,6,7-trimethoxyflavone (IV), C20H20O7, m. 166-7°, λ212, 272, 336 mμ (ε 39,690, 22,138, 24,711); acetate, m. 149-50. The aq. fraction from the acid hydrolysis of I concd. to 500 ml. and neutralized gave pos. reactions with Fehling and Tollens reagents. Parallel paper chromatograms of the aq. ext. and glucose soln. developed according to Horrocks and Manning (C.A. 43, 8426h) gave identical spots. Similarly, chromatograms of the osazone and glucosazone obtained by the procedure of Burton, et al. (C.A. 45, 4297b), gave identical spots. II (0.4 g.) in 10 ml. (EtCO)2O refluxed 2 hrs. with 0.3 g. PhOH and 18 ml. freshly distd. 55% HI, the mixt. dild. with 100 ml. H2O, extd. with Et2O and EtOAc, the org. fractions washed 3 times with aq. Na2S2O3, and the dried ext. evapd. yielded 3,4',5,6,7-pentahydroxyflavonol (V), C15H10O7, m. 290° (decompn., charing between 314-20°); pentaacetate, m. 234-5°. Methylation of V with CH2N2 by the usual technique regenerated III. III (0.5 g.) in 50 ml. alc. and 50 ml. 20% KOH in 70% alc. boiled 20 hrs. and the concd. soln. dild. with H2O, satd. with CO2, acidified with HCl, extd. with Et2O, and the product recrystd. (dil. Me2CO) gave 0.05 g. p-MeOC6H4CO2H, m. 183-4°. A similar fission of IV gave p-EtOC6H4CO2H, m. 194-5°. Ozonolysis of III and IV gave identical results, demonstrating the presence of only a 4'-substituent in the benzene ring of II. IIa (0.1 g.) in 40 ml. anhyd. EtOAc ozonized 7 min., the ozonide decompd. by hydrogenation with 5% Pd-C, the filtered soln. evapd., and the residue crystd. (Me2CO-C6H6) gave an acid, sublimed at 125°/0.01 mm. to yield 0.02 g. p-AcOC6H4CO2H. V gave a pink color with Mg and HCl, and orange ppt. with Pb(OAc)2 in alc., turning brown on standing, and dark olive-green color with alc. FeCl3, identical with those reported by Goldsworthy and Robinson (C.A. 31, 22139) for V. III was identical with a specimen of authentic 3,4',5,6,7-pentamethoxyflavone. I (1 g.) in MeOH and CH2N2 (from 18 g. H2NCON(NO)Me) in Et2O kept 24 hrs. and treated with CH2N2 (10 g. H2NCON(NO)Me) in Et2O, the mixt. kept 24 hrs. and again treated with CH2N2 (10 g. H2NCON(NO)Me), kept 24 hrs., and evapd. at 20° in vacuo, the residue chromatographed in dry Me2CO on 150 g. Magnesol and eluted in succession with Me2CO, moist EtOAc, and 50% alc., the final fraction crystd. (dil. alc. and dil. Me2CO) (N atm.) gave 0.6 g. tetramethoxy compd. (VI), C25H28O12, m. 227-8° (decompn.), λ 212, 267, 326 mμ (ε 39,651, 27,627, 29,695). VI (0.8 g.) in 50 ml. 10% HCl in dil. alc. refluxed 3.5 hrs., the soln. dild. with 100 ml. H2O, the mixt. extd. 3 times with 40 ml. EtOAc, and the product crystd. (dil. alc.) gave 0.4 g. monohydroxytetramethoxy compd. (VII), C19H18O7, m. 253-4° λ 212, 260, 330 mμ (ε 38,871, 19,630, 26,641), converted by methylation with CH2N2 in Et2O to III and acetylated to a monoacetate (VIII), m. 151-3° (decompn.). VIII (0.075 g.) in anhyd. EtOAc ozonized 3 min., the ozonide hydrogenated with 0.1 g. 5% Pd-C, the filtered soln. evapd., and the crystd. (Me2CO-C6H6) residue sublimed at 125°/0.01 mm. gave 0.013 g. p-AcOC6H4CO2H, indicating that the glucose mol. in I is attached to the 4'-position in II.
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    47. 47
      Schilling, E. E.; Panero, J. L.; Crozier, B. S.; Scott, R. W.; Dávila, P. Bricklebush (Brickellia) Phylogeny Reveals Dimensions of the Great Asteraceae Radiation in Mexico. Mol. Phylogenet. Evol. 2015, 85, 161– 170,  DOI: 10.1016/j.ympev.2015.02.007
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      Bricklebush (Brickellia) phylogeny reveals dimensions of the great Asteraceae radiation in Mexico
      Schilling Edward E; Panero Jose L; Crozier Bonnie S; Scott Randall W; Davila Patricia
      Molecular phylogenetics and evolution (2015), 85 (), 161-70 ISSN:.
      Data from molecular phylogenetics were used to assess aspects of diversity and relationships in Brickellia, a large and widespread genus of Eupatorieae. The dataset included sequence data from nuclear ribosomal ITS, ETS, and plastid psbA-trnH regions. An initial question was to assess the monophyly of the genus and whether Barroetea, Phanerostylis, and Kuhnia should be recognized as separate from or included in Brickellia. The results supported the hypothesis that Brickellia is monophyletic, with the small (2-3 species) Pleurocoronis as the sister group and showed Barroetea, Phanerostylis, and Kuhnia all embedded within the genus. Results of a time calibrated phylogeny from a BEAST analysis gave an estimated origination time for Brickellia at about 9 million years ago (Ma), with the oldest split within the genus dated at about 7.5Ma. A BAMM analysis based on the time calibrated tree showed that Brickellia has one rate shift in diversification associated with its origin in the late Miocene. Some lineages within the genus have had an increase in the rate of diversification over the past 5Ma, whereas other lineages have had a decrease in net diversification during this period. The results also elucidated nine clades within Brickellia which are accepted as taxonomic sections, and that will form logical units for future detailed studies.
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    48. 48
      Sharaf, M.; Mansour, R. M. A.; Saleh, N. A. M. Exudate Flavonoids from Aerial Parts of Four CleomeSpecies. Biochem. Syst. Ecol. 1992, 20, 443– 448,  DOI: 10.1016/0305-1978(92)90084-Q
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      Exudate flavonoids from aerial parts of four Cleome species
      Sharaf, Mohamed; Mansour, Ragaa M. A.; Saleh, Nabiel A. M.
      Biochemical Systematics and Ecology (1992), 20 (5), 443-8CODEN: BSECBU; ISSN:0305-1978.
      The aerial parts of four Cleome species (Capparaceae) were investigated for their surface flavonoids. Ten methylated flavonoids were isolated and identified as 5,7,4'-trihydroxy-3-methoxyflavone (isokaempferide), 5,7,4'-trihydroxy-3,3'-dimethyoxyflavone, 5,7,4'-trihydroxy-6,3'-dimethoxyflavone (jaceosidin), 5,4'-dihydroxy-3,6,7-trimethoxyflavone (penduletin), 5,7,3',4'-tetrahydroxy-3,6-dimethoxyflavone (axillarin), 5,7,4'-trihydroxy-6,3',5'-trimethoxyflavone, 5,4'-dihydroxy-3,6,7,3'-tetramethoxyflavone (chrysosplenetin), 5,3'-dihydroxy-3,6,7,4',5'-pentamethoxyflavone, 5,4'-dihydroxy-3,6,7,8,3'-pentamethoxyflavone and 5-hydroxy-3,6,7,3',4',5'-hexamethoxyflavone.
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    49. 49
      Bai, N.; He, K.; Zhou, Z.; Lai, C.-S.; Zhang, L.; Quan, Z.; Shao, X.; Pan, M.-H.; Ho, C.-T. Flavonoids from Rabdosia Rubescens Exert Anti-Inflammatory and Growth Inhibitory Effect against Human Leukemia HL-60 Cells. Food Chem. 2010, 122, 831– 835,  DOI: 10.1016/j.foodchem.2010.03.071
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      Flavonoids from Rabdosia rubescens exert anti-inflammatory and growth inhibitory effect against human leukemia HL-60 cells
      Bai, Naisheng; He, Kan; Zhou, Zhu; Lai, Ching-Shu; Zhang, Li; Quan, Zheng; Shao, Xi; Pan, Min-Hsiung; Ho, Chi-Tang
      Food Chemistry (2010), 122 (3), 831-835CODEN: FOCHDJ; ISSN:0308-8146. (Elsevier Ltd.)
      Eight flavonoids were isolated from the aerial parts of the Rabdosia rubescens plant. Their chem. structures were detd. using 1D and 2D NMR and high-resoln. MS data. The flavonoids were tested for cytotoxicity in cancer cell lines (Hep G2, COLO 205, MCF-7, HL-60) and anti-inflammatory activity in LPS-treated RAW264.7 macrophages in vitro. Two compds. were modestly active in inhibiting nitrite prodn. by macrophages. One compd. was selectively active against HL-60 cells with IC50 = 7.55 μM. This value was comparable to IC50 4.64 μM of doxorubicin (pos. control).
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      Bukhari, I. A.; Khan, R. A.; Gilani, A. H.; Shah, A. J.; Hussain, J.; Ahmad, V. U. The analgesic, anti-inflammatory and calcium antagonist potential ofTanacetum artemisioides. Arch. Pharmacal Res. 2007, 30, 303– 312,  DOI: 10.1007/BF02977610
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      The analgesic, anti-inflammatory and calcium antagonist potential of Tanacetum artemisioides
      Bukhari, Ishfaq Ali; Khan, Rafeeq Alam; Gilani, Anwar-ul Hassan; Shah, Abdul Jabbar; Hussain, Javid; Ahmad, Viqar Uddin
      Archives of Pharmacal Research (2007), 30 (3), 303-312CODEN: APHRDQ; ISSN:0253-6269. (Pharmaceutical Society of Korea)
      Several species of the genus Tanacetum are traditionally used in a variety of health conditions including pain, inflammation, respiratory and gastrointestinal disorders. In the current investigation, we evaluated the plant ext. of T. artemisioides and some of its pure compds. (flavonoids) for analgesic, anti-inflammatory and calcium antagonist effects in various in-vivo and in vitro studies. Using the acetic acid induced writhing test, i.p. administration of the plant ext. (25-50 mg/kg) and its flavonoid compds. TA-1 and TA-2 (1-5 mg/kg) exhibited significant analgesic activity. The max. analgesic effect obsd. with the crude ext. of the plant was 71% at 50 mg/kg, while that of compds. TA-1 and TA-2 (5 mg/kg i.p) was 75 and 47%, resp. The plant ext. and its pure compds. caused inhibition of formalin induced paw licking in mice predominantly in the second phase of the test. Diclofenac sodium, a std. ref. compd., showed a similar effect in these chem. induced pain models. In the carrageenan induced rat paw edema assay, the plant ext. (50-200 mg/kg i.p) demonstrated significant (P < 0.01) anti-inflammatory activity which was comparable to that obtained with diclofenac sodium and indomethacin. In isolated rabbit jejunum prepns. the plant ext. showed an atropine sensitive dose-dependent (0.10-1.0 mg/mL) spasmogenic activity followed by a spasmolytic effect at the next higher doses (3-5 mg/mL). The crude ext. of the plant also inhibited the high K+-induced contractions, indicating a calcium channel blocking (CCB) activity, which was further confirmed when the plant ext. caused a right-ward shift in the Ca++ concn. response curves in the isolated rabbit jejunum prepns., similar to that seen with verapamil. The flavonoid compds. isolated from the plant were devoid of any activity in the isolated tissue prepns. These results indicate that the plant ext. of T. artemisioides possesses analgesic, anti-inflammatory and CCB activities. The flavonoid compds. of the plant may have a role in its obsd. analgesic and anti-inflammatory activities, while the CCB activity of the plant may be attributed to some other chem. constituents present. Moreover the findings support the traditional reputation of the genus Tanacetum for its therapeutic benefits in pain and inflammatory conditions.
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      Halfon, B.; Cifrçi, E.; Topçu, G. Flavonoid Constituents of Sideritis Caesarea. Turk. J. Chem. 2013, 37, 464– 472,  DOI: 10.3906/kim-1206-45
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      Flavonoid constituents of Sideritis caesarea
      Halfon, Belkis; Ciftci, Ece; Topcu, Gulacti
      Turkish Journal of Chemistry (2013), 37 (3), 464-472CODEN: TJCHE3; ISSN:1300-0527. (Scientific and Technological Research Council of Turkey)
      The acetone ext. of the aerial parts of Sideritis caesarea Duman, Aytac & Baser (Lamiaceae) afforded the flavonoids penduletin (1) and apigenin (2) and 6 glycosylated flavonoids, 4'-O-methyl-isoscutellarein-7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-6''-O-acetyl-β-D-glucopyranoside (3), 4'-O-methylhypolaetin-7-O-[6''-O-acetyl-β-D-allopyranosyl-(1→2)]-6''-O-acetyl-β-D-glucopyranoside (4), isoscutellarein-7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-6''-O-acetyl-β-D-glucopyranoside (5), isoscutellarein-7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (6), 4'-O-methylhypolaetin-7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (7), and hypolaetin-7-O-[6'''-O-acetyl-β-D-allopyranosyl-(1→2)]-β-D-glucopyranoside (8). The compds. were identified by the use of 1D- and 2D-NMR and UV spectroscopic techniques and by comparisons with the reported data. The acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities of the acetone, methanol, and water exts. of the plant and of the flavones penduletin and apigenin were evaluated at 200 μg/mL. The water ext. exhibited better activity against the enzyme AChE as compared to both the acetone and the methanol exts. Penduletin (1) showed significant activity against BChE (66.58%) while apigenin (2) showed weak activity against both enzymes.
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      de Pascual Teresa, J.; Díaz, F.; Sánchez, F. J.; Hernández, J.; Grande, M. Flavonoids from Digitalis Thapsi Leaves. Planta Med. 1980, 38, 271– 272,  DOI: 10.1055/s-2008-1074875
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      Flavonoids from Digitalis thapsi leaves
      De Pascual Teresa, J.; Diaz, F.; Sanchez, F. J.; Hernandez, J. M.; Grande, M.
      Planta Medica (1980), 38 (3), 271-2CODEN: PLMEAA; ISSN:0032-0943.
      From the leaves of D. thapsi 7 flavonoids were isolated: 3,3',7-trimethylquercetin, polycladin, 3'-methoxycalycopterin, jaranol, calycopterin, penduletin, and cirsimaritin. Calycopterin was the only flavonol previously described in this species.
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      Sy, L.-K.; Brown, G. D. Three Sesquiterpenes From Artemisia Annua. Phytochemistry 1998, 48, 1207– 1211,  DOI: 10.1016/S1389-1723(99)80227-8
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      Three sesquiterpenes from Artemisia annua
      Sy, Lai-King; Brown, Geoffrey D.
      Phytochemistry (1998), 48 (7), 1207-1211CODEN: PYTCAS; ISSN:0031-9422. (Elsevier Science Ltd.)
      The dried leaves of Artemisia annua, collected from Sichuan Province in Southern China, have yielded the unusual cadinane sesquiterpene I oxygenated at the 7-position and the novel eudesmane sesquiterpene II, in addn. to several known sesquiterpenes and flavanoids.
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      Muhammad, A.; Tel-Cayan, G.; Öztürk, M.; Nadeem, S.; Duru, M. E.; Anis, I.; Ng, S. W.; Shah, M. R. Biologically active flavonoids from Dodonaea viscosa and their structure-activity relationships. Ind. Crops Prod. 2015, 78, 66– 72,  DOI: 10.1016/j.indcrop.2015.10.011
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      Biologically active flavonoids from Dodonaea viscosa and their structure-activity relationships
      Muhammad, Akhtar; Tel-Cayan, Gulsen; Ozturk, Mehmet; Nadeem, Said; Duru, Mehmet E.; Anis, Itrat; Ng, Seik W.; Shah, Muhammad R.
      Industrial Crops and Products (2015), 78 (), 66-72CODEN: ICRDEW; ISSN:0926-6690. (Elsevier B.V.)
      Antioxidant and anticholinesterase activities of twelve flavonoids i.e. santin (1), penduletin (2), viscosine (3), 6,7-dimethylkaempferol (4), kaempferol- 3- methylether (5), 3,4'-dimethoxy-5,7-dihydroxyflavone (6), 5,7,4'-trihydroxy-3'-(3-hydroxymethylbutyl)-3,6-dimethoxyflavone (7), 5,7-dihydroxy-3'-(2-hydroxy-3-methyl-3-butenyl)-3,6,4'-trimethoxy-flavone (8), 5,7-dihydroxy-3'-(3-hydroxy-methylbutyl)-3,6,4'-trimethoxyflavone (9), 5,7-dihydroxy-3'-(4''-acetoxy-3''-methylbutyl)-3,6,4'-trimethoxy flavone (10), aromadendrin, (2S,3S) 3,4',5,7-tetrahydroxyflavanone (11), and pinocembrin (12), together with monohydrated crystal (1A) of 1 and anhyd. crystal (3A) of 3 - isolated from Dodonaea viscosa - were studied. The results are given as 50% inhibition concns. (IC50). Their structure-activity relationships are discussed for both activities. Flavonoids 3 and 10 showed higher antioxidant activity in all tests. 3 Also showed moderate acetylcholinesterase (IC50: 182.97 ± 1.25 μM) and significant butyrylcholinesterase (IC50: 47.07 ± 0.54 μM) inhibitory activities. Compds. 2 (IC50: 55.78 ± 1.01 μM) and 3A (IC50: 58.72 ± 1.02 μM) were also moderate anticholinesterase agents against butyrylcholinesterase enzyme. Monohydrate crystal (1A) showed better antioxidant and anticholinesterase activities than its amorphous form (1). In contrast, the amorphous 3 exhibited better activity than the anhyd. crystal (3A). In hydrous crystal, the water mol. might be responsible for better activity. These natural flavonoids can be used as pharmaceuticals and/or preservatives in resp. industries.
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      Arslanian, R. L.; Stermitz, F. R.; Castedo, L. 3-Methoxy-5-Hydroxyflavonols from TillandsiaPurpurea. J. Nat. Prod. 1986, 49, 1177– 1178,  DOI: 10.1021/np50048a062
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      3-Methoxy-5-hydroxyflavonols from Tillandsia purpurea
      Arslanian, Robert L.; Stermitz, Frank R.; Castedo, Luis
      Journal of Natural Products (1986), 49 (6), 1177-8CODEN: JNPRDF; ISSN:0163-3864.
      Retusin and artemetin were isolated from T. purpurea and identified by 1H NMR, UV spectroscopy and TLC comparisons with stds. Penduletin 4'-O-Me ether was tentatively identified. Several addnl. methoxylated 5-hydroxyflavones were detected.
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      Sagir, Z. O.; Carikci, S.; Kilic, T.; Goren, A. C. Metabolic Profile and Biological Activity of Sideritis Brevibracteata P. H. Davis Endemic to Turkey. Int. J. Food Prop. 2017, 20, 2994– 3005,  DOI: 10.1080/10942912.2016.1265981
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      Metabolic profile and biological activity of Sideritis brevibracteata P. H. Davis endemic to Turkey
      Sagir, Zuleyha Ozer; Carikci, Sema; Kilic, Turgut; Goren, Ahmet C.
      International Journal of Food Properties (2017), 20 (12), 2994-3005CODEN: IJFPFO; ISSN:1094-2912. (Taylor & Francis, Inc.)
      Essential oil and phenolic compns. of Sideritis brevibracteata P. H. Davis, which is an endemic species in Turkey and commonly used as a herbal tea for some diseases, were detd. by GC-MS and Liq. chromatog.-mass spectrometry (LC-MS/MS) techniques. While the main components of the essential oil were detd. as caryophyllene, germacrene-D, and α-cadinene, the phenolic compds. quercetagetin-3,6-dimethylether and chlorogenic acid were found to be the main compds. in the exts. of the species. The characteristic diterpenoids of Sideritis species such as siderol, linearol, eubotriol, sideridiol, and athonolone were isolated and their structures were elucidated by 1D and 2D NMR (NMR) techniques. Weak inhibitory activity of species against butyryl-cholinesterase was detd. Antioxidant capacity of the acetone and methanol exts. was detd. by DPPH free radical scavenging activity, β-carotene linoleic acid assays, and CUPRAC assays.
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      Pettit, G. R.; Meng, Y.; Herald, D. L.; Stevens, A. M.; Pettit, R. K.; Doubek, D. L. Antineoplastic Agents 540. The Indian Gynandropsis Gynandra (Capparidaceae). Oncol. Res. 2005, 15, 59– 68,  DOI: 10.3727/096504005775082039
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      Antineoplastic agents 540. The Indian Gynandropsis gynandra (Capparidaceae)
      Pettit, George R.; Meng, Yanhui; Herald, Delbert L.; Stevens, Andrew M.; Pettit, Robin K.; Doubek, Dennis L.
      Oncology Research (2005), 15 (2), 59-68CODEN: ONREE8; ISSN:0965-0407. (Cognizant Communication Corp.)
      The CH3OH-CH2Cl2 ext. of an Indian collection (entire plant) of Gynandropsis gynandra (L.) Briq. was sepd. based on bioassay results employing cancer cell lines. Six cancer cell growth inhibitors were isolated and found to be known flavone apegenin (4) and flavonols 1-3, 5, and 6. The structure of flavonol 2 was confirmed by x-ray crystal structure detn. All of the five flavonols (1-3, 5, 6) inhibited the murine P388 lymphocytic leukemia cell line with ED50 values of 3.0, 9.2, 4.0, 0.37, and 3.9 μg/mL, resp. All six of the flavonoids (1-6) also exhibited activity against a panel of six human cancer cell lines. Penduletin (3) inhibited growth of the Gram-neg. pathogen Neisseria gonorrhoeae and apegenin (4) inhibited growth of the Gram-pos. opportunist Enterococcus faecalis.
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      Lan, J. E.; Li, X. J.; Zhu, X. F.; Sun, Z. L.; He, J. M.; Zloh, M.; Gibbons, S.; Mu, Q. Flavonoids from Artemisia Rupestris and Their Synergistic Antibacterial Effects on Drug-Resistant Staphylococcus Aureus. Nat. Prod. Res. 2019, 35, 1881– 1886,  DOI: 10.1080/14786419.2019.1639182
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      Sachdev, K.; Kulshreshtha, D. K. Flavonoids from Dodonaea Viscosa. Phytochemistry 1983, 22, 1253– 1256,  DOI: 10.1016/0031-9422(83)80234-9
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      Flavonoids from Dodonaea viscosa
      Sachdev, Kusum; Kulshreshtha, Dinesh K.
      Phytochemistry (Elsevier) (1983), 22 (5), 1253-6CODEN: PYTCAS; ISSN:0031-9422.
      Eight flavonoids, including the novel compd. I, were isolated from D. viscosa. The structure of I was detd. by std. spectral methods.
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      van Heerden, F. R.; Viljoen, A. M.; van Wyk, B.-E. The Major Flavonoid of Dodonaea Angustifolia. Fitoterapia 2000, 71, 602– 604,  DOI: 10.1016/S0367-326X(00)00201-X
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      The major flavonoid of Dodonaea angustifolia
      van Heerden, F. R.; Viljoen, A. M.; van Wyk, B.-E.
      Fitoterapia (2000), 71 (5), 602-604CODEN: FTRPAE; ISSN:0367-326X. (Elsevier Science B.V.)
      The major leaf flavonoid of Dodonaea angustifolia, an important South African traditional medicine, has been identified as 5,7,4'-trihydroxy-3,6-dimethoxyflavone.
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      Teffo, L. S.; Aderogba, M. A.; Eloff, J. N. Antibacterial and Antioxidant Activities of Four Kaempferol Methyl Ethers Isolated from Dodonaea Viscosa Jacq. Var. Angustifolia Leaf Extracts. S. Afr. J. Bot. 2010, 76, 25– 29,  DOI: 10.1016/j.sajb.2009.06.010
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      Antibacterial and antioxidant activities of four kaempferol methyl ethers isolated from Dodonaea viscosa Jacq. var. angustifolia leaf extracts
      Teffo, L. S.; Aderogba, M. A.; Eloff, J. N.
      South African Journal of Botany (2010), 76 (1), 25-29CODEN: SAJBDD; ISSN:0254-6299. (Elsevier B.V.)
      Fractionation of dichloromethane and acetone fractions obtained by serial extn. from the leaf powder of Dodonaea viscosa Jacq. var. angustifolia (Sapindaceae) resulted in the isolation of four kaempferol Me ethers. The compds. were identified by spectral data (1H NMR, 13C NMR and MS) as: 3, 5, 7-trihydroxy-4'-methoxyflavone (1); 5, 7, 4'-trihydroxy-3, 6-dimethoxyflavone (2); 5, 7-dihydroxy-3, 6, 4'-trimethoxyflavone (santin) (3); and 5-hydroxy -3, 7, 4'-trimethoxyflavone (4) together with 3,4',5,7-tetrahydroxy flavone (kaempferol) (5). Antioxidant potential of the compds. was evaluated using a DPPH spectrophotometric assay, while antibacterial activity was detd. using a serial diln. microplate technique. The isolates demonstrated varying degrees of antioxidant and antibacterial activities. Of all the compds. investigated, compds. 1 and 5 demonstrated some antioxidant activity (EC50 = 75.49±1.76 μM and 35.06±0.85 resp.) but lower than L-ascorbic acid (EC50 = 13.55±0.28 μM) used as a std. antioxidant agent. The min. inhibitory concn. (MIC) of isolated compds. against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli and Pseudomonas aeruginosa varied from 16 μg/mL to more than 250 μg/mL. Some structure activity relationships could be established for these compds.
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      Khan, A.; Iqbal, Z.; Khan, A.; Khan, I.; Nasir, F.; Khan, I.; Khan, J. A. Pharmacokinetic Profiling of a Novel Flavonoid “Viscosine” from Dodonaea Viscosa Using High Performance Liquid Chromatography. J. Liq. Chromatogr. Relat. Technol. 2015, 38, 128– 136,  DOI: 10.1080/10826076.2014.883542
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      Pharmacokinetic Profiling of a Novel Flavonoid "Viscosine" from Dodonaea viscosa Using High Performance Liquid Chromatography
      Khan, Amirzada; Iqbal, Zafar; Khan, Abad; Khan, Inamullah; Nasir, Fazli; Khan, Ismail; Khan, Jamshaid Ali
      Journal of Liquid Chromatography & Related Technologies (2015), 38 (1), 128-136CODEN: JLCTFC; ISSN:1082-6076. (Taylor & Francis, Inc.)
      Pharmacokinetic (PK) profiling of a novel flavonoid "Viscosine" was carried out in healthy rabbits following both IV and oral administration. Various PK parameters were investigated using the developed HPLC-UV method. The concn. of the Viscosine in plasma samples following both IV and oral administration was plotted as a function of time on normal and semi-log graph papers. The plasma drug concn. as a function of time profile of the Viscosine following IV bolus administration and oral administration showed the bi-exponential decline that indicates that PK of the Viscosine follows two compartment open model. The Viscosine is rapidly but incompletely absorbed following oral administration from hard gelatin capsules and tmax was achieved just in 0.5 h (30 min). The mean ± SD of Cmax was 0.981 ± 0.021 μg/mL. The very low plasma drug concn. achieved shows that Viscosine has lower permeability following oral administration. Similarly, following IV bolus drug administration, the plasma drug concn. as a function of time curve of Viscosine was a bi-exponential curve that follows two compartment open model. Viscosine is readily distributed and established equil. between central and peripheral compartments. Higher vol. of distribution (Vd) shows the longer stay in the peripheral compartments. The β-elimination half-life is approx. 3.8 h. The AUC values also indicate the distribution of the drug in various body fluids. In summary, the bioavailability of the drug after oral administration (F = 0.32) indicates that Viscosine is a low sol. drug; however, the Vd was higher compared with the IV bolus injection while MRT was about 15.45 h. These studies indicate that capsules can be used as a suitable dosage form for the administration of Viscosine.
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      Rosler, H.; Star, A. E.; Mabry, T. J. New 6-Methoxyflavonols from Centaurea Jacea. Phytochemistry 1971, 10, 450– 451,  DOI: 10.1016/s0031-9422(00)94073-1
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      New 6-methoxyflavonols from Centaurea jacea
      Rosler, Heinz; Star, Aura E.; Mabry, Tom J.
      Phytochemistry (Elsevier) (1971), 10 (2), 450-1CODEN: PYTCAS; ISSN:0031-9422.
      Two new flavonols were isolated from C. jacea flowers. They are 4',5,7-trihydroxy-3,6-dimethoxyflavone and its 7-O-β-D-glucoside.
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      Selim, R. M.; Shaaban, M.; Hamdy, A. A.; Abou Zeid, A. A.; Ata, A. V. Viscosine: A new microbial flavonoid from marine-derived,Streptomycessp. RMS518F. Vietnam J. Chem. 2019, 57, 288– 295,  DOI: 10.1002/vjch.201900034
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      Viscosine: A new microbial flavonoid from marine-derived, Streptomyces sp. RMS518F
      Selim, Rehab M.; Shaaban, Mohamed; Hamdy, Abdelhamid Aly; Abou Zeid, Azza A.; Ata, Athar
      Vietnam Journal of Chemistry (2019), 57 (3), 288-295CODEN: VJCIAO; ISSN:2572-8288. (Wiley-VCH Verlag GmbH & Co. KGaA)
      During the search for bioactive metabolites from marine sediment derived-actinomycetes, a new microbial flavonoid 6-hydroxykaempferol-3,6-dimethyl ether, viscosine (1) was isolated from the marine sediment derived-actinobacteria RMS518F strain. Structure of the compd. (1) was detd. by 1D- and 2D-NMR (1 and 2-Dimensional NMR), mass spectrometry and comparison of these data with literature. Taxonomically, the strain was characterized as Streptomyces carpaticus on the bases of 16S rRNA gene sequence. Biol., compd. (1) exhibited moderate antimicrobial activity against the Gram-pos. bacteria, Staphylococcus aureus ATCC6538-P; Bacillus cereus ATCC11778 and Saccharomyces cerevisiae ATCC9080 yeast. Compd. (1)was also significantly active against the human colon carcinoma cell line (HCT-116) and the hepatocellular carcinoma cell line (Hep G2) with IC50 values of 73.4 and 62.8 μg/mL, resp. compared with the antineoplastic drug (Doxorubicin) (37.6 and 21.6 μg/mL), while no activity has been noticed against the human breast cancer cell line (MCF-7).
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      Khan, A. Z.; Mohammad, A.; Iqbal, Z.; Anis, I.; Shah, M. R.; Nadeem, S.; Rabnawaz, M.; Shahidullah, A.; Khan, H.; Khan, I. Molecular docking of viscosine as a new lipoxygenase inhibitor isolated from Dodonaea viscosa. Bangladesh J. Pharmacol. 2013, 8, 36– 39,  DOI: 10.3329/bjp.v8i1.13088
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      Durmaz, L. Antioxidant, antiepileptic, and anticholinergic properties of 4′,5,7-Trihydroxy-3,6-dimethoxyflavone as natural phenolic compound: a toxicology approach. Toxin Rev. 2019, 40, 292– 299,  DOI: 10.1080/15569543.2019.1610894
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      Cushnie, T. P. T.; Lamb, A. J. Antimicrobial Activity of Flavonoids. Int. J. Antimicrob. Agents 2005, 26, 343– 356,  DOI: 10.1016/j.ijantimicag.2005.09.002
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      Antimicrobial activity of flavonoids
      Cushnie, T. P. Tim; Lamb, Andrew J.
      International Journal of Antimicrobial Agents (2005), 26 (5), 343-356CODEN: IAAGEA; ISSN:0924-8579. (Elsevier B.V.)
      A review. Flavonoids are ubiquitous in photosynthesizing cells and are commonly found in fruit, vegetables, nuts, seeds, stems, flowers, tea, wine, propolis and honey. For centuries, prepns. contg. these compds. as the principal physiol. active constituents have been used to treat human diseases. Increasingly, this class of natural products is becoming the subject of anti-infective research, and many groups have isolated and identified the structures of flavonoids possessing antifungal, antiviral and antibacterial activity. Moreover, several groups have demonstrated synergy between active flavonoids as well as between flavonoids and existing chemotherapeutics. Reports of activity in the field of antibacterial flavonoid research are widely conflicting, probably owing to inter- and intra-assay variation in susceptibility testing. However, several high-quality investigations have examd. the relationship between flavonoid structure and antibacterial activity and these are in close agreement. In addn., numerous research groups have sought to elucidate the antibacterial mechanisms of action of selected flavonoids. The activity of quercetin, for example, has been at least partially attributed to inhibition of DNA gyrase. It has also been proposed that sophoraflavone G and (-)-epigallocatechin gallate inhibit cytoplasmic membrane function, and that licochalcones A and C inhibit energy metab. Other flavonoids whose mechanisms of action have been investigated include robinetin, myricetin, apigenin, rutin, galangin, 2,4,2'-trihydroxy-5'-methylchalcone and lonchocarpol A. These compds. represent novel leads, and future studies may allow the development of a pharmacol. acceptable antimicrobial agent or class of agents.
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      Álvarez-Martínez, F. J.; Barrajón-Catalán, E.; Herranz-López, M.; Micol, V. Antibacterial Plant Compounds, Extracts and Essential Oils: An Updated Review on Their Effects and Putative Mechanisms of Action. Phytomedicine 2021, 90, 153626,  DOI: 10.1016/j.phymed.2021.153626
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      Antibacterial plant compounds, extracts and essential oils: An updated review on their effects and putative mechanisms of action
      Alvarez-Martinez, F. J.; Barrajon-Catalan, E.; Herranz-Lopez, M.; Micol, V.
      Phytomedicine (2021), 90 (), 153626CODEN: PYTOEY; ISSN:0944-7113. (Elsevier GmbH)
      A review. Antibiotic-resistant bacteria pose a global health threat. Traditional antibiotics can lose their effectiveness, and the development of novel effective antimicrobials has become a priority in recent years. In this area, plants represent an invaluable source of antimicrobial compds. with vast therapeutic potential. To review the full possible spectrum of plant antimicrobial agents (plant compds., exts. and essential oils) discovered from 2016 to 2021 and their potential to decrease bacterial resistance. Their activities against bacteria, with special emphasis on multidrug resistant bacteria, mechanisms of action, possible combinations with traditional antibiotics, roles in current medicine and future perspectives are discussed. Studies focusing on the antimicrobial activity of compds. of plant origin and their mechanism of action against bacteria were identified and summarized, including contributions from Jan. 2016 until Jan. 2021. Articles were extd. from the Medline database using PubMed search engine with relevant keywords and operators. The search yielded 11,689 articles from 149 countries, of which 101 articles were included in this . Reports from 41 phytochems. belonging to 20 families were included. Reports from plant exts. and essential oils from 39 plant species belonging to 17 families were also included. Polyphenols and terpenes were the most active phytochems. studied, either alone or as a part of plant exts. or essential oils. Plasma membrane disruption was the most common mechanism of antimicrobial action. No. and position of phenolic hydroxyl groups, double bonds, delocalized electrons and conjugation with sugars in the case of flavonoids seemed to be crucial for antimicrobial capacity. Combinations of phytochems. with beta-lactam antibiotics were the most studied, and the inhibition of efflux pumps was the most common synergistic mechanism. In recent years, terpenes, flavones, flavonols and some alkaloids and phenylpropanoids, either isolated or as a part of exts., have shown promising antimicrobial activity, being membrane disruption their most common mechanism. However, their utilization as appropriate antimicrobials need to be boosted by means of new omics technologies and network pharmacol. to find the most effective combinations among them or in combination with antibiotics.
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      Waditzer, M.; Bucar, F. Flavonoids as Inhibitors of Bacterial Efflux Pumps. Molecules 2021, 26, 6904,  DOI: 10.3390/molecules26226904
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      Flavonoids as Inhibitors of Bacterial Efflux Pumps
      Waditzer, Martin; Bucar, Franz
      Molecules (2021), 26 (22), 6904CODEN: MOLEFW; ISSN:1420-3049. (MDPI AG)
      Flavonoids are widely occurring secondary plant constituents, and are abundant in vegetable and fruit diets as well as herbal medicines. Therapeutic treatment options for bacterial infections are limited due to the spread of antimicrobial resistances. Hence, in a no. of studies during the last few years, different classes of plant secondary metabolites as resistance-modifying agents have been carried out. In this review, we present the role of flavonoids as inhibitors of bacterial efflux pumps. Active compds. could be identified in the subclasses of chalcones, flavan-3-ols, flavanones, flavones, flavonols, flavonolignans and isoflavones; by far the majority of compds. were aglycons, although some glycosides like kaempferol glycosides with p-coumaroyl acylation showed remarkable results. Staphylococcus aureus NorA pump was the focus of many studies, followed by mycobacteria, whereas Gram-neg. bacteria are still under-investigated.
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    71. 71
      Pinto, H. B.; Brust, F. R.; Macedo, A. J.; Trentin, D. S. The Antivirulence Compound Myricetin Possesses Remarkable Synergistic Effect with Antibacterials upon Multidrug Resistant Staphylococcus Aureus. Microb. Pathog. 2020, 149, 104571,  DOI: 10.1016/j.micpath.2020.104571
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      The antivirulence compound myricetin possesses remarkable synergistic effect with antibacterials upon multidrug resistant Staphylococcus aureus
      Pinto, Helber Barboza; Brust, Flavia Roberta; Macedo, Alexandre Jose; Trentin, Danielle Silva
      Microbial Pathogenesis (2020), 149 (), 104571CODEN: MIPAEV; ISSN:0882-4010. (Elsevier Ltd.)
      Staphylococcus aureus is an opportunistic pathogen involved in several human diseases and presents ability to produce many virulence factors and resistance to antibacterial agents. One of the current strategies to combat such multidrug resistant bacteria is the antibacterial combination therapy. Myricetin is a flavonoid capable of inhibiting several S. aureus virulence factors without influencing on bacterial growth. Therefore, the combination of antibacterials with the antivirulence compd. myricetin may provide a pos. interaction to control multidrug resistant-bacteria. This work aims to evaluate the effect of the combination of myricetin with oxacillin and vancomycin against methicillin resistant S. aureus (MRSA) and vancomycin intermediate resistant S. aureus (VISA) strains. Concns. used in combination assays were detd. according to the min. inhibitory concn. (MIC) for antibacterials and to the biofilm min. inhibitory concn. (BMIC) for myricetin. Checkerboard evaluations showed redn. in MIC for antibacterials in presence of myricetin and time-kill assays confirmed the synergism for these combinations, except for VISA strain when the flavonoid was combined with vancomycin. Importantly, when myricetin was combined with oxacillin, MRSA strain became susceptible to the antibacterial. Myricetin did not reduce staphyloxanthin prodn., indicating that the oxacillin susceptibility seems not to be related to this step of functional membrane microdomains. In vivo evaluations using Galleria mellonella confirmed the efficacy of oxacillin plus myricetin in treatment of MRSA infected-larvae when compared to the control groups, increasing in 20% host survival. The present work points out the potential of antibacterial and antivirulence compds. combinations as new alternative to control infections by multidrug resistant-bacteria.
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      Wang, S.-Y.; Sun, Z.-L.; Liu, T.; Gibbons, S.; Zhang, W.-J.; Qing, M. Flavonoids from Sophora moorcroftiana and their Synergistic Antibacterial Effects on MRSA. Phytother Res. 2014, 28, 1071– 1076,  DOI: 10.1002/ptr.5098
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      Flavonoids from Sophora moorcroftiana and their Synergistic Antibacterial Effects on MRSA
      Wang, Shuang-Ying; Sun, Zhong-Lin; Liu, Tao; Gibbons, Simon; Zhang, Wen-Ju; Qing, Mu
      Phytotherapy Research (2014), 28 (7), 1071-1076CODEN: PHYREH; ISSN:0951-418X. (John Wiley & Sons Ltd.)
      Synergy is now a widely recognized approach that has direct applicability for new pharmaceuticals. The ethanolic ext. of the aerial parts of the herb Sophora moorcroftiana showed significant antibacterial activity against drug-resistant Staphylococcus aureus, and its min. inhibitory concn. (MIC) was 8 μg/mL. In a phytochem. study of the ext., five flavonoids were obtained. However, the isolates exhibited antibacterial activity in the range of 32-128 μg/mL, which was weaker than the ext. In combination with antibiotics, the antibacterially inactive compd. genistein (1) and diosmetin (4) showed significant synergistic activity against drug-resistant S. aureus. In combination with norfloxacin, genistein (1) reduced the MIC to 16 μg/mL and showed synergy against strain SA1199B with a fractional inhibitory concn. index (FICI) of 0.38. With the antibiotics norfloxacin, streptomycin and ciprofloxacin, diosmetin (4) showed synergy against SA1199B, RN4220 and EMRSA-15, with FICI values of 0.38, 0.38 and 0.09, resp. In an efflux expt. to elucidate a plausible mechanism for the obsd. synergy, genistein showed marginal inhibition of the NorA efflux protein.
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    73. 73
      Vipin, C.; Saptami, K.; Fida, F.; Mujeeburahiman, M.; Rao, S. S.; Athmika; Arun, A. B.; Rekha, P. D. Potential Synergistic Activity of Quercetin with Antibiotics against Multidrug-Resistant Clinical Strains of Pseudomonas Aeruginosa. PLoS One 2020, 15, e0241304  DOI: 10.1371/journal.pone.0241304
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      73
      Potential synergistic activity of quercetin with antibiotics against multidrug-resistant clinical strains of Pseudomonas aeruginosa
      Vipin, Chembili; Saptami, Kanekar; Fida, Fathima; Mujeeburahiman, Musliyarakath; Rao, Sneha S.; Athmika; Arun, Ananthapadmanabha Bhagwath; Rekha, Punchappady Devasya
      PLoS One (2020), 15 (11), e0241304CODEN: POLNCL; ISSN:1932-6203. (Public Library of Science)
      Development of drug resistance in opportunistic pathogens is one of the major healthcare challenges assocd. with infection management. Combination therapy has many advantages due to the simultaneous action of two drugs on two sep. cellular targets. However, selection of the drugs should offer safety and synergistic interaction against most of the strains. Here, the efficacy of antibiotics in combination with quercetin, a natural flavonoid capable of targeting quorum sensing was tested against biofilm-forming Pseudomonas aeruginosa strains previously isolated from catheter assocd. urinary tract infection. Based on the antibiotic susceptibility pattern, synergistic effect of quercetin with selected antibiotics (levofloxacin, ceftriaxone, gentamycin, tobramycin and amikacin) was tested at the fractional concns. of MIC by the checkerboard method and the fractional inhibitory concn. index (FICi) was calcd. to est. the synergistic effect. Effect of the synergistic combinations were further tested using time-kill assay, and against biofilm formation and biofilm cell viability. Cytotoxicity assays were performed using Human Embryonic Kidney 293T cells (HEK-293T) using the effective drug combinations with resp. controls. The biofilm formation and biofilm cell viability were drastically affected with quercetin and selected antibiotics combinations with ≥80% inhibition. In vitro infection studies showed that all the strains could exert significant cell killing (68 to 85%) and the drug combinations decreased the infection rate significantly by reducing the cell killing effect of P. aeruginosa (p<0.05). The synergistic effect of quercetin is attributed to its quorum sensing inhibitory properties. These findings indicate that quercetin along with existing antibiotics can potentiate the treatment against P. aeruginosa infection and may reduce the selection pressure due to antibiotic overuse.
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    74. 74
      Cushnie, T. P. T.; Lamb, A. J. Recent Advances in Understanding the Antibacterial Properties of Flavonoids. Int. J. Antimicrob. Agents 2011, 38, 99– 107,  DOI: 10.1016/j.ijantimicag.2011.02.014
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      74
      Recent advances in understanding the antibacterial properties of flavonoids
      Cushnie, T. P. Tim; Lamb, Andrew J.
      International Journal of Antimicrobial Agents (2011), 38 (2), 99-107CODEN: IAAGEA; ISSN:0924-8579. (Elsevier B.V.)
      A review. Antibiotic resistance is a major global problem and there is a pressing need to develop new therapeutic agents. Flavonoids are a family of plant-derived compds. with potentially exploitable activities, including direct antibacterial activity, synergism with antibiotics, and suppression of bacterial virulence. In this review, recent advances towards understanding these properties are described. Information is presented on the ten most potently antibacterial flavonoids as well as the five most synergistic flavonoid-antibiotic combinations tested in the last 6 years (identified from PubMed and ScienceDirect). Top of these resp. lists are panduratin A, with min. inhibitory concns. (MICs) of 0.06-2.0 μg/mL against Staphylococcus aureus, and epicatechin gallate, which reduces oxacillin MICs as much as 512-fold. Research seeking to improve such activity and understand structure-activity relationships is discussed. Proposed mechanisms of action are also discussed. In addn. to direct and synergistic activities, flavonoids inhibit a no. of bacterial virulence factors, including quorum-sensing signal receptors, enzymes and toxins. Evidence of these mol. effects at the cellular level include in vitro inhibition of biofilm formation, inhibition of bacterial attachment to host ligands, and neutralization of toxicity towards cultured human cells. In vivo evidence of disruption of bacterial pathogenesis includes demonstrated efficacy against Helicobacter pylori infection and S. aureus α-toxin intoxication.
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    75. 75
      Tchoumtchoua, J.; Mathiron, D.; Pontarin, N.; Gagneul, D.; van Bohemen, A. I.; Otogo N’nang, E.; Mesnard, F.; Petit, E.; Fontaine, J. X.; Molinié, R.; Quéro, A. Phenolic Profiling of Flax Highlights Contrasting Patterns in Winter and Spring Varieties. Molecules 2019, 24, 4303– 14,  DOI: 10.3390/molecules24234303
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      Phenolic profiling of flax highlights contrasting patterns in winter and spring varieties
      Tchoumtchoua, Job; Mathiron, David; Pontarin, Nicole; Gagneul, David; van Bohemen, Anne-Isaline; N'nang, Elvis Otogo; Mesnard, Francois; Petit, Emmanuel; Fontaine, Jean-Xavier; Molinie, Roland; Quero, Anthony
      Molecules (2019), 24 (23), 4303CODEN: MOLEFW; ISSN:1420-3049. (MDPI AG)
      Flax (Linum usitatissimum) is a plant grown in temperate regions either for its fiber or for its seeds, which are rich in the essential fatty acid omega-3. It is also well known as a source of medicinal compds. The chem. compn. of its leaves is currently poorly described. In order to fill this gap, we have conducted a comprehensive anal. of flax leaf metabolome. The exploration of the metabolome allowed the characterization of compds. isolated for the first time in flax leaves. These mols. were isolated by preparative HPLC and then characterized by NMR, LC-MS and std. anal. This work extended our picture of C-glycosyl-flavonoids and coniferyl alc. derivs. accumulated in flax. The follow-up of the content of these different metabolites via UPLC-MS revealed significant accumulation differences in spring and winter flax leaves. In particular, two methylated C-glycosylflavonoids (swertisin and swertiajaponin) were the most abundant phenolic compds. in winter flax whereas they were not detected in spring flax. This result suggests that these 2 compds. are involved in cold stress tolerance in flax.
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    • Photograph of a T. bergeri individual; results of antibacterial screening of hexanic and dichloromethane fractions of T. bergeri methanol and methanol/water fractions of T. bergeri against a panel of Gram-positive and Gram-negative pathogens; TLC agar overlay bioautography of the dichloromethane fraction against MSSA, MRSA, and S. caprae; HPLC chromatograms of subfractions A F2.3 and B F2.5; MSE mass spectra of compound 1 isolated from the dichloromethane fraction of T. bergeri and those of the standard of penduletin; MSE mass spectra of compound 2 isolated from the dichloromethane fraction of T. bergeri and those of the standard of viscosine; MS/MS spectra of compound 1 isolated from the dichloromethane fraction of T. bergeri and those of the standard of penduletin; and MS/MS spectra of compound 2 isolated from the dichloromethane fraction of T. bergeri and those of the standard of viscosine (PDF)


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