Rapid Evaluation of Phenolic Component Profile and Analysis of Oleuropein Aglycon in Olive Oil by Atmospheric Pressure Chemical Ionization−Mass Spectrometry (APCI−MS)Click to copy article linkArticle link copied!
Abstract
Epidemiological studies have linked the Mediterranean diet with a low incidence of cardiovascular diseases. Olive oil, the major fat component of this diet, is characterized by antioxidant properties related to their content in catecholic components, particularly oleuropein aglycon. Therefore quantification of these components in edible oils may be important in determining the quality, and consequently its commercial value. The present method allows us to obtain the profile of the phenolic components of the oil from the methanolic extracts of the crude olive oil. In particular tyrosol, hydroxytyrosol, elenolic acid, deacetoxyligstroside and deacetoxyoleuropein aglycons, ligstroside and oleuropein aglycons, and 10-hydroxy-oleuropein are clearly identified by atmospheric pressure chemical ionization−mass spectrometry (APCI−MS). Moreover, oleuropein and its isomers present in the oil are quantified by APCI−MS/MS analysis of the extracts without preliminary separation from other phenolic compounds.
Keywords: Olive oil; APCI-MS and APCI-MS/MS; phenolic components; quantitative and qualitative analysis; oleuropein aglycon; catecholic compounds
*
To whom correspondence should be addressed. Telephone: +39-02-20488323. Fax: +39-02-29404961. E-mail: [email protected].
†
Institute of Pharmacological Sciences.
‡
Catholic University of Sacred Heart.
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- Nikolaos Katsinas, Andreia Bento da Silva, Amalia Enríquez-de-Salamanca, Naiara Fernández, Maria Rosário Bronze, Soraya Rodríguez-Rojo. Pressurized Liquid Extraction Optimization from Supercritical Defatted Olive Pomace: A Green and Selective Phenolic Extraction Process. ACS Sustainable Chemistry & Engineering 2021, 9
(16)
, 5590-5602. https://doi.org/10.1021/acssuschemeng.0c09426
- Fátima Rubio-Senent, Antonio Lama-Muñoz, Guillermo Rodríguez-Gutiérrez, and Juan Fernández-Bolaños . Isolation and Identification of Phenolic Glucosides from Thermally Treated Olive Oil Byproducts. Journal of Agricultural and Food Chemistry 2013, 61
(6)
, 1235-1248. https://doi.org/10.1021/jf303772p
- Georg Dierkes, Sonja Krieger, Roman Dück, Annette Bongartz, Oliver J. Schmitz, and Heiko Hayen . High-Performance Liquid Chromatography–Mass Spectrometry Profiling of Phenolic Compounds for Evaluation of Olive Oil Bitterness and Pungency. Journal of Agricultural and Food Chemistry 2012, 60
(31)
, 7597-7606. https://doi.org/10.1021/jf3020574
- Leonardo Di Donna, Hicham Benabdelkamel, Fabio Mazzotti, Anna Napoli, Monica Nardi, and Giovanni Sindona . High-Throughput Assay of Oleopentanedialdheydes in Extra Virgin Olive Oil by the UHPLC−ESI-MS/MS and Isotope Dilution Methods. Analytical Chemistry 2011, 83
(6)
, 1990-1995. https://doi.org/10.1021/ac200152r
- Edwin N. Frankel. Chemistry of Extra Virgin Olive Oil: Adulteration, Oxidative Stability, and Antioxidants. Journal of Agricultural and Food Chemistry 2010, 58
(10)
, 5991-6006. https://doi.org/10.1021/jf1007677
- Shaoping Fu, Antonio Segura-Carretero, David Arráez-Román, Javier A. Menéndez, A. De La Torre and Alberto Fernández-Gutiérrez . Tentative Characterization of Novel Phenolic Compounds in Extra Virgin Olive Oils by Rapid-Resolution Liquid Chromatography Coupled with Mass Spectrometry. Journal of Agricultural and Food Chemistry 2009, 57
(23)
, 11140-11147. https://doi.org/10.1021/jf901590n
- Mario Dell'Agli,, Rossana Fagnani,, Nico Mitro,, Samuele Scurati,, Maura Masciadri,, Luciana Mussoni,, Germana V. Galli,, Enrica Bosisio,, Maurizio Crestani,, Emma De Fabiani,, Elena Tremoli, and, Donatella Caruso. Minor Components of Olive Oil Modulate Proatherogenic Adhesion Molecules Involved in Endothelial Activation. Journal of Agricultural and Food Chemistry 2006, 54
(9)
, 3259-3264. https://doi.org/10.1021/jf0529161
- Karina de la Torre-Carbot,, Olga Jauregui,, Eva Gimeno,, Ana I. Castellote,, Rosa M. Lamuela-Raventós, and, M. Carmen López-Sabater. Characterization and Quantification of Phenolic Compounds in Olive Oils by Solid-Phase Extraction, HPLC-DAD, and HPLC-MS/MS. Journal of Agricultural and Food Chemistry 2005, 53
(11)
, 4331-4340. https://doi.org/10.1021/jf0501948
- Hassan K. Obied,, Malcolm S. Allen,, Danny R. Bedgood,, Paul D. Prenzler,, Kevin Robards, and, Regine Stockmann. Bioactivity and Analysis of Biophenols Recovered from Olive Mill Waste. Journal of Agricultural and Food Chemistry 2005, 53
(4)
, 823-837. https://doi.org/10.1021/jf048569x
- Paul Andrewes,, Johanneke L. H. C. Busch,, Teun de Joode,, Anneke Groenewegen, and, Helene Alexandre. Sensory Properties of Virgin Olive Oil Polyphenols: Identification of Deacetoxy-ligstroside Aglycon as a Key Contributor to Pungency. Journal of Agricultural and Food Chemistry 2003, 51
(5)
, 1415-1420. https://doi.org/10.1021/jf026042j
- Rosario Zamora,, Manuel Alaiz, and, Francisco J. Hidalgo. Influence of Cultivar and Fruit Ripening on Olive (Olea europaea) Fruit Protein Content, Composition, and Antioxidant Activity. Journal of Agricultural and Food Chemistry 2001, 49
(9)
, 4267-4270. https://doi.org/10.1021/jf0104634
- Simona M. Monti,, Alberto Ritieni,, Raffaele Sacchi,, Kerstin Skog,, Eva Borgen, and, Vincenzo Fogliano. Characterization of Phenolic Compounds in Virgin Olive Oil and Their Effect on the Formation of Carcinogenic/Mutagenic Heterocyclic Amines in a Model System. Journal of Agricultural and Food Chemistry 2001, 49
(8)
, 3969-3975. https://doi.org/10.1021/jf010240d
- Manuel Brenes,, Aranzazu García,, Pedro García, and, Antonio Garrido. Rapid and Complete Extraction of Phenols from Olive Oil and Determination by Means of a Coulometric Electrode Array System. Journal of Agricultural and Food Chemistry 2000, 48
(11)
, 5178-5183. https://doi.org/10.1021/jf000686e
- Wanying Li, Jiangyao Chen, Yuemeng Ji, Jun Zheng, Taicheng An. Recent progress in chemical ionization mass spectrometry and its application in atmospheric environment. Atmospheric Environment 2024, 325 , 120426. https://doi.org/10.1016/j.atmosenv.2024.120426
- David Bongiorno, Vita Di Stefano, Serena Indelicato, Giuseppe Avellone, Leopoldo Ceraulo. Bio‐phenols determination in olive oils: Recent mass spectrometry approaches. Mass Spectrometry Reviews 2023, 42
(4)
, 1462-1502. https://doi.org/10.1002/mas.21744
- Debabrata Majumder, Mousumi Debnath, Kamal Nayan Sharma, Surinder Singh Shekhawat, G.B.K.S Prasad, Debasish Maiti, Seeram Ramakrishna. Olive Oil Consumption can Prevent Non-communicable Diseases and
COVID-19: A Review. Current Pharmaceutical Biotechnology 2022, 23
(2)
, 261-275. https://doi.org/10.2174/1389201022666210412143553
- Poournima Patil, Suresh Killedar. Chitosan and glyceryl monooleate nanostructures containing gallic acid isolated from amla fruit: targeted delivery system. Heliyon 2021, 7
(3)
, e06526. https://doi.org/10.1016/j.heliyon.2021.e06526
- María Luisa Castejón, Tatiana Montoya, Catalina Alarcón-de-la-Lastra, Marina Sánchez-Hidalgo. Potential Protective Role Exerted by Secoiridoids from Olea europaea L. in Cancer, Cardiovascular, Neurodegenerative, Aging-Related, and Immunoinflammatory Diseases. Antioxidants 2020, 9
(2)
, 149. https://doi.org/10.3390/antiox9020149
- Hanene Zemmouri, Sonda Ammar, Amel Boumendjel, Mahfoud Messarah, Abdelfattah El Feki, Mohamed Bouaziz. Chemical composition and antioxidant activity of Borago officinalis L. leaf extract growing in Algeria. Arabian Journal of Chemistry 2019, 12
(8)
, 1954-1963. https://doi.org/10.1016/j.arabjc.2014.11.059
- Giovanni Ventura, Cosima D. Calvano, Ramona Abbattista, Mariachiara Bianco, Cristina De Ceglie, Ilario Losito, Francesco Palmisano, Tommaso R.I. Cataldi. Characterization of bioactive and nutraceutical compounds occurring in olive oil processing wastes. Rapid Communications in Mass Spectrometry 2019, 33
(21)
, 1670-1681. https://doi.org/10.1002/rcm.8514
- Lucía Olmo-García, Nikolas Kessler, Heiko Neuweger, Karin Wendt, José María Olmo-Peinado, Alberto Fernández-Gutiérrez, Carsten Baessmann, Alegría Carrasco-Pancorbo. Unravelling the Distribution of Secondary Metabolites in Olea europaea L.: Exhaustive Characterization of Eight Olive-Tree Derived Matrices by Complementary Platforms (LC-ESI/APCI-MS and GC-APCI-MS). Molecules 2018, 23
(10)
, 2419. https://doi.org/10.3390/molecules23102419
- Sandra Silva, Mar Garcia‐Aloy, Maria Eduardo Figueira, Emilie Combet, William Mullen, Maria Rosário Bronze. High Resolution Mass Spectrometric Analysis of Secoiridoids and Metabolites as Biomarkers of Acute Olive Oil Intake—An Approach to Study Interindividual Variability in Humans. Molecular Nutrition & Food Research 2018, 62
(2)
https://doi.org/10.1002/mnfr.201700065
- Muhammad H. Alu’datt, Taha Rababah, Mohammad N. Alhamad, Sana Gammoh, Khalil Ereifej, Majdi A. Al-Mahasneh, Doa’a Al-u’datt, Ola Naimi, Neveen Hussein, Stan Kubow. Application of Olive Oil as Nutraceutical and Pharmaceutical Food: Composition and Biofunctional Constituents and Their Roles in Functionality, Therapeutic, and Nutraceutical Properties. 2017, 265-298. https://doi.org/10.1016/B978-0-12-811412-4.00010-2
- Aadil Bajoub, El Amine Ajal, Alberto Fernández-Gutiérrez, Alegría Carrasco-Pancorbo. Evaluating the potential of phenolic profiles as discriminant features among extra virgin olive oils from Moroccan controlled designations of origin. Food Research International 2016, 84 , 41-51. https://doi.org/10.1016/j.foodres.2016.03.010
- Maria Stella Cosio, Andrea Romano, Matteo Scampicchio. Olive Oil and Electronic Nose. 2016, 83-92. https://doi.org/10.1016/B978-0-12-800243-8.00009-3
- Mine Gültekin-Özgüven, Fatma Davarcı, Ayça A. Paslı, Nalan Demir, Beraat Özçelik. Determination of phenolic compounds by ultra high liquid chromatography-tandem mass spectrometry: Applications in nuts. LWT - Food Science and Technology 2015, 64
(1)
, 42-49. https://doi.org/10.1016/j.lwt.2015.05.014
- Hamid-Reza Adhami, Martin Zehl, Christina Dangl, Dominic Dorfmeister, Marco Stadler, Ernst Urban, Peter Hewitson, Svetlana Ignatova, Liselotte Krenn. Preparative isolation of oleocanthal, tyrosol, and hydroxytyrosol from olive oil by HPCCC. Food Chemistry 2015, 170 , 154-159. https://doi.org/10.1016/j.foodchem.2014.08.079
- Aikaterini Termentzi, Maria Halabalaki, Alexios Leandros Skaltsounis. From Drupes to Olive Oil: An Exploration of Olive Key Metabolites. 2015, 147-177. https://doi.org/10.1016/B978-1-63067-041-2.50012-4
- Pantelis Charisiadis, Constantinos G. Tsiafoulis, Andreas G. Tzakos, Ioannis P. Gerothanassis. Dynamic changes in composition of extracts of natural products as monitored by
in situ
NMR. Magnetic Resonance in Chemistry 2014, 52
(12)
, 764-768. https://doi.org/10.1002/mrc.4128
- Akram Zribi, Boutheina Gargouri, Hazem Jabeur, Ahmed Rebaï, Ridha Abdelhedi, Mohamed Bouaziz. Enrichment of pan‐frying refined oils with olive leaf phenolic‐rich extract to extend the usage life. European Journal of Lipid Science and Technology 2013, 115
(12)
, 1443-1453. https://doi.org/10.1002/ejlt.201300037
- Vassiliki G. Kontogianni, Pantelis Charisiadis, Evangelia Margianni, Fotini N. Lamari, Ioannis P. Gerothanassis, Andreas G. Tzakos. Olive Leaf Extracts Are a Natural Source of Advanced Glycation End Product Inhibitors. Journal of Medicinal Food 2013, 16
(9)
, 817-822. https://doi.org/10.1089/jmf.2013.0016
- Stefania Vichi, Nuria Cortés-Francisco, Josep Caixach. Insight into virgin olive oil secoiridoids characterization by high-resolution mass spectrometry and accurate mass measurements. Journal of Chromatography A 2013, 1301 , 48-59. https://doi.org/10.1016/j.chroma.2013.05.047
- Stefania Bulotta, Manuela Oliverio, Diego Russo, Antonio Procopio. Biological Activity of Oleuropein and its Derivatives. 2013, 3605-3638. https://doi.org/10.1007/978-3-642-22144-6_156
- Mercedes Pérez-Bonilla, Sofía Salido, Adolfo Sánchez, Teris A. van Beek, Joaquín Altarejos. Effect of Extraction Conditions on the Antioxidant Activity of Olive Wood Extracts. International Journal of Food Science 2013, 2013 , 1-13. https://doi.org/10.1155/2013/719593
- Fabio Mazzotti, Hicham Benabdelkamel, Leonardo Di Donna, Loredana Maiuolo, Anna Napoli, Giovanni Sindona. Assay of tyrosol and hydroxytyrosol in olive oil by tandem mass spectrometry and isotope dilution method. Food Chemistry 2012, 135
(3)
, 1006-1010. https://doi.org/10.1016/j.foodchem.2012.05.005
- Susana M. Cardoso, Soraia I. Falcão, António M. Peres, Maria R.M. Domingues. Oleuropein/ligstroside isomers and their derivatives in Portuguese olive mill wastewaters. Food Chemistry 2011, 129
(2)
, 291-296. https://doi.org/10.1016/j.foodchem.2011.04.049
- Brett M. Davis, Senti T. Senthilmohan, Murray J. McEwan. Direct Determination of Antioxidants in Whole Olive Oil Using the SIFT‐MS‐TOSC Assay. Journal of the American Oil Chemists' Society 2011, 88
(6)
, 785-792. https://doi.org/10.1007/s11746-010-1722-7
- Maria Francesca Riccio, Alexandra C. H. F. Sawaya, Patrícia V. Abdelnur, Sergio A. Saraiva, Renato Haddad, Marcos N. Eberlin, Rodrigo R. Catharino. Easy Ambient Sonic-Spray Ionization Mass Spectrometric of Olive Oils: Quality Control and Certification of Geographical Origin. Analytical Letters 2011, 44
(8)
, 1489-1497. https://doi.org/10.1080/00032719.2010.512688
- Justyna Gromadzka, Waldemar Wardencki. TRENDS IN EDIBLE VEGETABLE OILS ANALYSIS. PART A. DETERMINATION OF DIFFERENT COMPONENTS OF EDIBLE OILS – A REVIEW. Polish Journal of Food and Nutrition Sciences 2011, 61
(1)
, 33-43. https://doi.org/10.2478/v10222-011-0002-z
- Mohamed Bouaziz, Hedya Jemai, Wahid Khabou, Sami Sayadi. Oil content, phenolic profiling and antioxidant potential of Tunisian olive drupes. Journal of the Science of Food and Agriculture 2010, 90
(10)
, 1750-1758. https://doi.org/10.1002/jsfa.4013
- Shaoping Fu, David Arráez-Roman, Antonio Segura-Carretero, Javier A. Menéndez, María P. Menéndez-Gutiérrez, Vicente Micol, Alberto Fernández-Gutiérrez. Qualitative screening of phenolic compounds in olive leaf extracts by hyphenated liquid chromatography and preliminary evaluation of cytotoxic activity against human breast cancer cells. Analytical and Bioanalytical Chemistry 2010, 397
(2)
, 643-654. https://doi.org/10.1007/s00216-010-3604-0
- Maria Francesca Riccio, Sérgio A. Saraiva, Lygia Azevedo Marques, Rosana Alberici, Renato Haddad, Jens C. Moller, Marcos N. Eberlin, Rodrigo Ramos Catharino. Easy mass spectrometry for metabolomics and quality control of vegetable and animal fats. European Journal of Lipid Science and Technology 2010, 112
(4)
, 434-438. https://doi.org/10.1002/ejlt.200900090
- Giovanni Sindona. A Marker of Quality of Olive Oils. 2010, 95-100. https://doi.org/10.1016/B978-0-12-374420-3.00011-5
- M. Stella Cosio, Simona Benedetti, Susanna Buratti, Matteo Scampicchio, Saverio Mannino. Application of the Electronic Nose in Olive Oil Analyses. 2010, 553-559. https://doi.org/10.1016/B978-0-12-374420-3.00060-7
- Jacob Zabicky. Analytical Aspects of Phenolic Compounds. 2009https://doi.org/10.1002/9780470682531.pat0289
- Shaoping Fu, David Arráez‐Román, Javier A. Menéndez, Antonio Segura‐Carretero, Alberto Fernández‐Gutiérrez. Characterization of isomers of oleuropein aglycon in olive oils by rapid‐resolution liquid chromatography coupled to electrospray time‐of‐flight and ion trap tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2009, 23
(1)
, 51-59. https://doi.org/10.1002/rcm.3855
- Dimitrios Boskou. Phenolic Compounds in Olives and Olive Oil. 2008, 11-44. https://doi.org/10.1201/9781420059946.ch3
- Photis Dais, Dimitrios Boskou. Detection and Quantification of Phenolic Compounds in Olive Oil, Olives, and Biological Fluids. 2008, 55-107. https://doi.org/10.1201/9781420059946.ch5
- Lei Zhou, Jie Kang, Li Fan, Xiao-Chi Ma, Hai-Yu Zhao, Jian Han, Bao-rong Wang, De-An Guo. Simultaneous analysis of coumarins and secoiridoids in Cortex Fraxini by high-performance liquid chromatography–diode array detection–electrospray ionization tandem mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis 2008, 47
(1)
, 39-46. https://doi.org/10.1016/j.jpba.2007.12.009
- Junhui Chen, Jie Liu, Frank Sen‐Chun Lee, Xiaoru Wang. Optimization of HPLC‐APCI‐MS conditions for the qualitative and quantitative determination of total solanesol in tobacco leaves. Journal of Separation Science 2008, 31
(1)
, 137-142. https://doi.org/10.1002/jssc.200700239
- Alessandra Bendini, Lorenzo Cerretani, Alegria Carrasco-Pancorbo, Ana Maria Gómez-Caravaca, Antonio Segura-Carretero, Alberto Fernández-Gutiérrez, Giovanni Lercker. Phenolic Molecules in Virgin Olive Oils: a Survey of Their Sensory Properties, Health Effects, Antioxidant Activity and Analytical Methods. An Overview of the Last Decade Alessandra. Molecules 2007, 12
(8)
, 1679-1719. https://doi.org/10.3390/12081679
- Leonardo Di Donna, Fabio Mazzotti, Anna Napoli, Raffaele Salerno, Ashif Sajjad, Giovanni Sindona. Secondary metabolism of olive secoiridoids. New microcomponents detected in drupes by electrospray ionization and high‐resolution tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2007, 21
(3)
, 273-278. https://doi.org/10.1002/rcm.2830
- Alegria Carrasco-Pancorbo, Ana Maria Gómez-Caravaca, Lorenzo Cerretani, Alessandra Bendini, Antonio Segura-Carretero, Alberto Fernández-Gutiérrez. A simple and rapid electrophoretic method to characterize simple phenols, lignans, complex phenols, phenolic acids, and flavonoids in extra-virgin olive oil. Journal of Separation Science 2006, 29
(14)
, 2221-2233. https://doi.org/10.1002/jssc.200600132
- Alegría Carrasco‐Pancorbo, David Arráez‐Román, Antonio Segura‐Carretero, Alberto Fernández‐Gutiérrez. Capillary electrophoresis‐electrospray ionization‐mass spectrometry method to determine the phenolic fraction of extra‐virgin olive oil. ELECTROPHORESIS 2006, 27
(11)
, 2182-2196. https://doi.org/10.1002/elps.200500650
- M.D. Luque de Castro, R. Japón-Luján. State-of-the-art and trends in the analysis of oleuropein and derivatives. TrAC Trends in Analytical Chemistry 2006, 25
(5)
, 501-510. https://doi.org/10.1016/j.trac.2005.11.007
- Claudio Galli, Francesco Visioli, Paola Bogani. Healthful Properties of Olive Oil Minor Components. 2006https://doi.org/10.1201/9781439832028.ch8
- Nadia Mulinacci, Catia Giaccherini, Francesca Ieri, Marzia Innocenti, Annalisa Romani, Franco F Vincieri. Evaluation of lignans and free and linked hydroxy‐tyrosol and tyrosol in extra virgin olive oil after hydrolysis processes. Journal of the Science of Food and Agriculture 2006, 86
(5)
, 757-764. https://doi.org/10.1002/jsfa.2411
- Alegria Carrasco‐Pancorbo, Lorenzo Cerretani, Alessandra Bendini, Antonio Segura‐Carretero, Tullia Gallina‐Toschi, Alberto Fernández‐Gutiérrez. Analytical determination of polyphenols in olive oils. Journal of Separation Science 2005, 28
(9-10)
, 837-858. https://doi.org/10.1002/jssc.200500032
- Elisa Tripoli, Marco Giammanco, Garden Tabacchi, Danila Di Majo, Santo Giammanco, Maurizio La Guardia. The phenolic compounds of olive oil: structure, biological activity and beneficial effects on human health. Nutrition Research Reviews 2005, 18
(1)
, 98-112. https://doi.org/10.1079/NRR200495
- Susana M Cardoso, Sylvain Guyot, Nathalie Marnet, José A Lopes‐da‐Silva, Catherine MGC Renard, Manuel A Coimbra. Characterisation of phenolic extracts from olive pulp and olive pomace by electrospray mass spectrometry. Journal of the Science of Food and Agriculture 2005, 85
(1)
, 21-32. https://doi.org/10.1002/jsfa.1925
- Davide Vogna, Alessandro Pezzella, Lucia Panzella, Alessandra Napolitano, Marco d'Ischia. Oxidative chemistry of hydroxytyrosol: isolation and characterisation of novel methanooxocinobenzodioxinone derivatives. Tetrahedron Letters 2003, 44
(45)
, 8289-8292. https://doi.org/10.1016/j.tetlet.2003.09.066
- Matteo Bonoli, Marina Montanucci, Tullia Gallina Toschi, Giovanni Lercker. Fast separation and determination of tyrosol, hydroxytyrosol and other phenolic compounds in extra-virgin olive oil by capillary zone electrophoresis with ultraviolet-diode array detection. Journal of Chromatography A 2003, 1011
(1-2)
, 163-172. https://doi.org/10.1016/S0021-9673(03)01100-2
- Francesco Visioli, Claudio Galli, Simona Grande, Katia Colonnelli, Cristian Patelli, Giovanni Galli, Donatella Caruso. Hydroxytyrosol Excretion Differs between Rats and Humans and Depends on the Vehicle of Administration. The Journal of Nutrition 2003, 133
(8)
, 2612-2615. https://doi.org/10.1093/jn/133.8.2612
- Anna Grazia Mignani, Peter R. Smith, Leonardo Ciaccheri, Antonio Cimato, Graziano Sani. Spectral nephelometry for making extravirgin olive oil fingerprints. Sensors and Actuators B: Chemical 2003, 90
(1-3)
, 157-162. https://doi.org/10.1016/S0925-4005(03)00101-1
- Chrisovalandis Grizis, Julia Atta‐Politou, Michael A. Koupparis. Simultaneous Determination of Oleuropein and Tyrosol in Plasma Using High Performance Liquid Chromatography with UV Detection. Journal of Liquid Chromatography & Related Technologies 2003, 26
(4)
, 599-616. https://doi.org/10.1081/JLC-120017908
- Alessandra Bendini, Matteo Bonoli, Lorenzo Cerretani, Barbara Biguzzi, Giovanni Lercker, Tullia Gallina Toschi. Liquid–liquid and solid-phase extractions of phenols from virgin olive oil and their separation by chromatographic and electrophoretic methods. Journal of Chromatography A 2003, 985
(1-2)
, 425-433. https://doi.org/10.1016/S0021-9673(02)01460-7
- M Brenes, A García, J J Rios, P García, A Garrido. Use of 1-acetoxypinoresinol to authenticate Picual olive oils. International Journal of Food Science and Technology 2002, 37
(6)
, 615-625. https://doi.org/10.1046/j.1365-2621.2002.00591.x
- Francesco Visioli, Andrea Poli, Claudio Gall. Antioxidant and other biological activities of phenols from olives and olive oil. Medicinal Research Reviews 2002, 22
(1)
, 65-75. https://doi.org/10.1002/med.1028
- Enzo Perri, Fabio Mazzotti, Andrea Raffaelli, Giovanni Sindona. High-throughput screening of tocopherols in natural extracts. Journal of Mass Spectrometry 2000, 35
(11)
, 1360-1361. https://doi.org/10.1002/1096-9888(200011)35:11<1360::AID-JMS60>3.0.CO;2-Y
- Francesco Visioli, Donatella Caruso, Claudio Galli, Serena Viappiani, Giovanni Galli, Angelo Sala. Olive Oils Rich in Natural Catecholic Phenols Decrease Isoprostane Excretion in Humans. Biochemical and Biophysical Research Communications 2000, 278
(3)
, 797-799. https://doi.org/10.1006/bbrc.2000.3879
- . Current Awareness. Phytochemical Analysis 2000, 339-344. https://doi.org/10.1002/1099-1565(200009/10)11:5<339::AID-PCA508>3.0.CO;2-H
- . Current Awareness. Journal of Mass Spectrometry 2000, 1055-1066. https://doi.org/10.1002/1096-9888(200008)35:8<1055::AID-JMS981>3.0.CO;2-8
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