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(+)-epi-α-Bisbolol Is the Wound-Healing Principle of Peperomia galioides: Investigation of the in Vivo Wound-Healing Activity of Related Terpenoids

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Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, North Dartmouth, Massachusetts 02747, Departamento de Ciencias Fisiológicas, Universidad Peruana Cayetano Heredia, Aptdo. Postal 4314, Lima 100, Perú, Departamento de Química, Universidad Peruana Cayetano Heredia, Aptdo. Postal 4314, Lima 100, Perú, and Laboratorios de Investigación y Desarrollo de Ciencia y Tecnología, y Departamento de Microbiología, Universidad Peruana Cayetano Heredia, Aptdo. Postal 4314, Lima 100, Perú
Cite this: J. Nat. Prod. 2001, 64, 10, 1357–1359
Publication Date (Web):October 4, 2001
https://doi.org/10.1021/np0102859
Copyright © 2001 American Chemical Society and American Society of Pharmacognosy
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Abstract

Bioassay-guided investigation of the ethanol extract of Peperomia galioides using a tensile strength method in mice as a monitor led to the isolation of epi-α-bisabolol (1) (ED50 155 μg/mL). An in vivo healing study of selected commercially available monoterpenoids yielded two bioactive compounds, α-bisabolol (2) and α-terpineol (3) (ED50 of 228 and 240 mg/g mouse, respectively).

 Departamento de Ciencias Fisiológicas, Universidad Peruana Cayetano Heredia.

 University of Massachusetts Dartmouth.

§

 Departamento de Química, Universidad Peruana Cayetano Heredia.

 Laboratorios de Investigación y Desarrollo y Departamento de Microbiología, Universidad Peruana Cayetano Heredia.

 G.B.H. and A.J.V. share senior coauthorship.

*

 To whom correspondence should be addressed. Tel:  (508) 999-8865. Fax:  (312) 910-6918. E-mail:  [email protected]

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  9. Shalini Ramalingam, Moola Joghee Nanjan Chandrasekar, Moola Joghee Nanjan. Plant-based Natural Products for Wound Healing: A Critical Review. Current Drug Research Reviews 2022, 14 (1) , 37-60. https://doi.org/10.2174/2589977513666211005095613
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  13. Cláudia Leites Luchese, Juliana Both Engel, Isabel Cristina Tessaro. Disposable, reusable and biodegradable hygiene products. 2021, 421-454. https://doi.org/10.1016/B978-0-12-821485-5.00003-2
  14. A. Frankova, L. Vistejnova, T. Merinas-Amo, Z. Leheckova, I. Doskocil, J. Wong Soon, T. Kudera, F. Laupua, A. Alonso-Moraga, L. Kokoska. In vitro antibacterial activity of extracts from Samoan medicinal plants and their effect on proliferation and migration of human fibroblasts. Journal of Ethnopharmacology 2021, 264 , 113220. https://doi.org/10.1016/j.jep.2020.113220
  15. Subramani Parasuraman, Pandurangan Perumal. Wound Healing Agents from Natural Sources. 2021, 95-148. https://doi.org/10.1007/978-981-16-2677-7_4
  16. Hayate Javed, M. F. Nagoor Meeran, Sheikh Azimullah, Lujain Bader Eddin, Vivek Dhar Dwivedi, Niraj Kumar Jha, Shreesh Ojha. α-Bisabolol, a Dietary Bioactive Phytochemical Attenuates Dopaminergic Neurodegeneration through Modulation of Oxidative Stress, Neuroinflammation and Apoptosis in Rotenone-Induced Rat Model of Parkinson’s Disease. Biomolecules 2020, 10 (10) , 1421. https://doi.org/10.3390/biom10101421
  17. Saed Aldalaen, Maha Nasr, Riham I. El-Gogary. Angiogenesis and collagen promoting nutraceutical-loaded nanovesicles for wound healing. Journal of Drug Delivery Science and Technology 2020, 56 , 101548. https://doi.org/10.1016/j.jddst.2020.101548
  18. Laura Hévila I. Leite, Gerlânia O. Leite, Bruno Anderson F. da Silva, Sacha Aubrey A.R. Santos, Francisco Ernani A. Magalhães, Paula P. Menezes, Mairim R. Serafini, Claudener S. Teixeira, Renan G. Brito, Priscila L. Santos, José Galberto M. da Costa, Adriano A.S. Araújo, Lucindo J. Quintans-Júnior, Irwin R.A. de Menezes, Henrique Douglas M. Coutinho, Adriana Rolim Campos. Molecular mechanism underlying orofacial antinociceptive activity of Vanillosmopsis arborea Baker (Asteraceae) essential oil complexed with β-cyclodextrin. Phytomedicine 2019, 55 , 293-301. https://doi.org/10.1016/j.phymed.2018.09.173
  19. Mohamed Ali-Seyed, Kavitha Vijayaraghavan. Nutraceuticals for Wound Healing: A Special Focus on Chromolaena odorata as Guardian of Health with Broad Spectrum of Biological Activities. 2019, 541-562. https://doi.org/10.1007/978-3-030-04624-8_36
  20. Fabíola Fernandes Galvão Rodrigues, Aracélio Viana Colares, Carla de Fatima Alves Nonato, Fabío Fernandes Galvão-Rodrigues, Magaly Lima Mota, Maria Flaviana Bezerra Moraes Braga, José Galberto Martins da Costa. In vitro antimicrobial activity of the essential oil from Vanillosmopsis arborea Barker (Asteraceae) and its major constituent, α-bisabolol. Microbial Pathogenesis 2018, 125 , 144-149. https://doi.org/10.1016/j.micpath.2018.09.024
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  22. Mina Yarazavi, Ebrahim Noroozian. A novel sorbent based on carbon nanotube/amino-functionalized sol-gel for the headspace solid-phase microextraction of α-bisabolol from medicinal plant samples using experimental design. Journal of Separation Science 2018, 41 (10) , 2229-2236. https://doi.org/10.1002/jssc.201700993
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  24. Rita de Cássia da Silveira e Sá, Tamires Lima, Flávio da Nóbrega, Anna de Brito, Damião de Sousa. Analgesic-Like Activity of Essential Oil Constituents: An Update. International Journal of Molecular Sciences 2017, 18 (12) , 2392. https://doi.org/10.3390/ijms18122392
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  26. Kavitha Vijayaraghavan, Johanna Rajkumar, Syed Nasir Abbas Bukhari, Badr Al-Sayed, Mohammed Ali Seyed. Chromolaena odorata: A neglected weed with a wide spectrum of pharmacological activities. Molecular Medicine Reports 2017, 15 (3) , 1007-1016. https://doi.org/10.3892/mmr.2017.6133
  27. Yasmin Valero Gutierrez, Lydia F. Yamaguchi, Marcilio M. de Moraes, Christopher S. Jeffrey, Massuo J. Kato. Natural products from Peperomia: occurrence, biogenesis and bioactivity. Phytochemistry Reviews 2016, 15 (6) , 1009-1033. https://doi.org/10.1007/s11101-016-9461-5
  28. Arie Budovsky, Ludmila Yarmolinsky, Shimon Ben-Shabat. Effect of medicinal plants on wound healing. Wound Repair and Regeneration 2015, 23 (2) , 171-183. https://doi.org/10.1111/wrr.12274
  29. Krishna Vyas, Henry Vasconez. Wound Healing: Biologics, Skin Substitutes, Biomembranes and Scaffolds. Healthcare 2014, 2 (3) , 356-400. https://doi.org/10.3390/healthcare2030356
  30. Laura Marongiu, Marta Donini, Michele Bovi, Massimiliano Perduca, Federico Vivian, Alessandro Romeo, Sofia Mariotto, Hugo L. Monaco, Stefano Dusi. The inclusion into PLGA nanoparticles enables α-bisabolol to efficiently inhibit the human dendritic cell pro-inflammatory activity. Journal of Nanoparticle Research 2014, 16 (8) https://doi.org/10.1007/s11051-014-2554-4
  31. Rosana Barreto, Ricardo Albuquerque-Júnior, Adriano Araújo, Jackson Almeida, Márcio Santos, André Barreto, Josimari DeSantana, Pollyana Siqueira-Lima, Jullyana Quintans, Lucindo Quintans-Júnior. A Systematic Review of the Wound-Healing Effects of Monoterpenes and Iridoid Derivatives. Molecules 2014, 19 (1) , 846-862. https://doi.org/10.3390/molecules19010846
  32. Yun-Zhi Li, Dai-Yin Peng, Min Dai, Cao-Mao Xiao, Hong-Bo Jiang, Jing Huang. A new phenylpropanoid from Peperomia tetraphylla. Natural Product Research 2013, 27 (9) , 837-840. https://doi.org/10.1080/14786419.2012.704372
  33. Aracélio Viana Colares, Fernando Almeida-Souza, Noemi Nosomi Taniwaki, Celeste da Silva Freitas Souza, José Galberto Martins da Costa, Kátia da Silva Calabrese, Ana Lúcia Abreu-Silva. In Vitro Antileishmanial Activity of Essential Oil of Vanillosmopsis arborea (Asteraceae) Baker. Evidence-Based Complementary and Alternative Medicine 2013, 2013 , 1-7. https://doi.org/10.1155/2013/727042
  34. Gerlânia de Oliveira Leite, Cícera Norma Fernandes, Irwin Rose Alencar de Menezes, José Galberto Martins da Costa, Adriana Rolim Campos. Attenuation of visceral nociception by α-bisabolol in mice: investigation of mechanisms. Organic and Medicinal Chemistry Letters 2012, 2 (1) https://doi.org/10.1186/2191-2858-2-18
  35. Yun-Zhi Li, Ai-Ping Tong, Jing Huang. Two New Norlignans and a New Lignanamide from Peperomia tetraphylla. Chemistry & Biodiversity 2012, 9 (4) , 769-776. https://doi.org/10.1002/cbdv.201100138
  36. Ying Cui, Lingzhi Li, Li Zhang, Jianyu Li, Jun Gu, Haiying Gong, Peng Guo, Wei Tong. Enhancement and mechanism of transdermal absorption of terpene-induced propranolol hydrochloride. Archives of Pharmacal Research 2011, 34 (9) , 1477-1485. https://doi.org/10.1007/s12272-011-0909-2
  37. N. K. A. Santos, H. D. M. Coutinho, G. S. B. Viana, Fabíola F. G. Rodrigues, José G. M. Costa. Chemical characterization and synergistic antibiotic activity of volatile compounds from the essential oil of Vanillosmopsis arborea. Medicinal Chemistry Research 2011, 20 (5) , 637-641. https://doi.org/10.1007/s00044-010-9372-8
  38. Gerlânia de O. Leite, Laura H.I. Leite, Renata de S. Sampaio, Mariana Késsia A. Araruna, Irwin Rose A. de Menezes, José Galberto M. da Costa, Adriana R. Campos. (−)-α-Bisabolol attenuates visceral nociception and inflammation in mice. Fitoterapia 2011, 82 (2) , 208-211. https://doi.org/10.1016/j.fitote.2010.09.012
  39. Ifedayo V. Ogungbe, Rebecca A. Crouch, William A. Haber, William N. Setzer. Phytochemical Investigation of Verbesina Turbacensis Kunth: Trypanosome Cysteine Protease Inhibition by (–)-Bornyl Esters. Natural Product Communications 2010, 5 (8) , 1934578X1000500. https://doi.org/10.1177/1934578X1000500801
  40. Paola A. Robayo-Gama, Clara E. Quijano, Gustavo Morales, Jorge A. Pino. Composition of the Essential Oil From Leaves of Peperomia galioides HBK Grown in Colombia. Journal of Essential Oil Research 2010, 22 (4) , 307-309. https://doi.org/10.1080/10412905.2010.9700332
  41. A.M. Chibiryaev, A. Yermakova, I.V. Kozhevnikov. Chemical and phase equilibria calculation of α-pinene hydration in CO2-expanded liquid. The Journal of Supercritical Fluids 2010, 51 (3) , 295-305. https://doi.org/10.1016/j.supflu.2009.11.001
  42. Guy P. P. Kamatou, Alvaro M. Viljoen. A Review of the Application and Pharmacological Properties of α ‐Bisabolol and α ‐Bisabolol‐Rich Oils. Journal of the American Oil Chemists' Society 2010, 87 (1) , 1-7. https://doi.org/10.1007/s11746-009-1483-3
  43. Elisabetta Cavalieri, Christian Bergamini, Sofia Mariotto, Serena Leoni, Luigi Perbellini, Elena Darra, Hisanori Suzuki, Romana Fato, Giorgio Lenaz. Involvement of mitochondrial permeability transition pore opening in α-bisabolol induced apoptosis. FEBS Journal 2009, 276 (15) , 3990-4000. https://doi.org/10.1111/j.1742-4658.2009.07108.x
  44. SOU N. MATSUNAGA, ALEX B. GUENTHER, JIM P. GREENBERG, MARK POTOSNAK, MARIA PAPIEZ, TSUTOM HIURA, SHUNGO KATO, SATOSHI NISHIDA, PETER HARLEY, YOSHIZUMI KAJII. Leaf level emission measurement of sesquiterpenes and oxygenated sesquiterpenes from desert shrubs and temperate forest trees using a liquid extraction technique. GEOCHEMICAL JOURNAL 2009, 43 (3) , 179-189. https://doi.org/10.2343/geochemj.1.0017
  45. Vincenzo De Feo, Alberto Juarez Belaunde, Joe Guerrero Sandoval, Felice Senatore, Carmen Formisano. Antibacterial Activity and Composition of the Essential Oil of Peperomia Galioides HBK (Piperaceae) from Peru. Natural Product Communications 2008, 3 (6) , 1934578X0800300. https://doi.org/10.1177/1934578X0800300622
  46. B. Kumar, M. Vijayakumar, R. Govindarajan, P. Pushpangadan. Ethnopharmacological approaches to wound healing—Exploring medicinal plants of India. Journal of Ethnopharmacology 2007, 114 (2) , 103-113. https://doi.org/10.1016/j.jep.2007.08.010
  47. Gustavo Moura-Letts, León F. Villegas, Ana Marçalo, Abraham J. Vaisberg, Gerald B. Hammond. In Vivo Wound-Healing Activity of Oleanolic Acid Derived from the Acid Hydrolysis of Anredera d iffusa. Journal of Natural Products 2006, 69 (6) , 978-979. https://doi.org/10.1021/np0601152
  48. Alvaro M. Viljoen, Angela Gono-Bwalya, Guy P.P. Kamatou, K. Hűsnű C. Başer, Betűl Demirci. The Essential Oil Composition and Chemotaxonomy of Salvia stenophylla and its Allies S. repens and S. runcinata. Journal of Essential Oil Research 2006, 18 (sup1) , 37-45. https://doi.org/10.1080/10412905.2006.12067117
  49. . Biological Activity of Chamomile (Matricaria chamomilla L.) Extracts. Journal of the Korean Society of Food Science and Nutrition 2005, 446-450. https://doi.org/10.3746/jkfn.2005.34.4.446
  50. Yasuyuki HASHIDOKO. Ecochemical Studies of Interrelationships between Epiphytic Bacteria and Host Plants via Secondary Metabolites. Bioscience, Biotechnology, and Biochemistry 2005, 69 (8) , 1427-1441. https://doi.org/10.1271/bbb.69.1427
  51. Elisabetta Cavalieri, Sofia Mariotto, Cinzia Fabrizi, Alessandra Carcereri de Prati, Rossella Gottardo, Stefano Leone, Luigi Valentino Berra, Giuliana Maria Lauro, Anna Rosa Ciampa, Hisanori Suzuki. α-Bisabolol, a nontoxic natural compound, strongly induces apoptosis in glioma cells. Biochemical and Biophysical Research Communications 2004, 315 (3) , 589-594. https://doi.org/10.1016/j.bbrc.2004.01.088
  52. Alexander Pauli, Heinz Schilcher. Specific Selection of Essential Oil Compounds for Treatment of Children’s Infection Diseases. Pharmaceuticals 2004, 1 (1) , 1-30. https://doi.org/10.3390/pharm01010001
  53. Ming-Jen Cheng, Shoiw-Ju Lee, Ying-Ying Chang, Szu-Huei Wu, Ian-Lih Tsai, Bolleddula Jayaprakasam, Ih-Sheng Chen. Chemical and cytotoxic constituents from Peperomia sui. Phytochemistry 2003, 63 (5) , 603-608. https://doi.org/10.1016/S0031-9422(03)00183-3
  54. A Hernández-Ceruelos, E Madrigal-Bujaidar, C de la Cruz. Inhibitory effect of chamomile essential oil on the sister chromatid exchanges induced by daunorubicin and methyl methanesulfonate in mouse bone marrow. Toxicology Letters 2002, 135 (1-2) , 103-110. https://doi.org/10.1016/S0378-4274(02)00253-9

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