Total Analysis of the Major Secoiridoids in Extra Virgin Olive Oil: Validation of an UHPLC-ESI-MS/MS Method

Overview

Journal Antioxidants (Basel)

Date 2021 Apr 3

PMID 33808450

Citations 10

Authors

Julian Lozano-Castellon

Anallely Lopez-Yerena

Alexandra Olmo-Cunillera

Olga Jauregui

Maria Perez

Rosa MA Lamuela-Raventos

Anna Vallverdu-Queralt

Affiliations

Soon will be listed here.

Abstract

Extra virgin olive oil (EVOO), one of the key foods of the Mediterranean diet, is distinguished by its high content of nutritional and antioxidant compounds compared to other vegetable oils. During EVOO production, the major secoiridoids of EVOO, oleacein, oleocanthal, ligstroside, and oleuropein aglycones, undergo a series of transformations to open- and closed-structure forms. The resulting mixture of compounds can become more complex during the analytical procedure, due to the keto-enol tautomerism of the open forms and their interaction with polar solvents, and therefore more challenging to analyze. Employing the same extraction method used to analyze the other EVOO phenolic compounds, we report here a simple UHPLC-ESI-MS/MS procedure for the quantification of those secoiridoids that is able to co-elute the different isomers of each compound. The method was validated following AOAC guidelines, and the matrix effect and recoveries were within satisfactory limits.

Citing Articles

Beneficial Effects of Tyrosol and Oleocanthal from Extra Virgin Olive Oil on Liver Health: Insights into Their Mechanisms of Action.

Gabbia D Biology (Basel). 2024; 13(10).

PMID: 39452069 PMC: 11504303. DOI: 10.3390/biology13100760.

Application of Thermo-Malaxation Followed by Three-Phase Centrifugation to Enable the Biorefinery of Alperujo, the Main By-Product of Olive Oil.

Fernandez-Prior A, Bermudez-Oria A, Rubio-Senent F, Villanueva-Lazo A, Fernandez-Bolanos J, Rodriguez-Gutierrez G Foods. 2023; 12(21).

PMID: 37959141 PMC: 10650604. DOI: 10.3390/foods12214023.

Storage Effects on Bioactive Phenols in Calabrian Monovarietal Extra Virgin Olive Oils Based on the EFSA Health Claim.

Frisina M, Bonacci S, Oliverio M, Nardi M, Vatrano T, Procopio A Foods. 2023; 12(20).

PMID: 37893692 PMC: 10606493. DOI: 10.3390/foods12203799.

Benchmarked molecular docking integrated molecular dynamics stability analysis for prediction of SARS-CoV-2 papain-like protease inhibition by olive secoiridoids.

Thangavel N, Albratty M J King Saud Univ Sci. 2022; 35(1):102402.

PMID: 36338939 PMC: 9617799. DOI: 10.1016/j.jksus.2022.102402.

Extra Virgin Olive Oil Extracts of Indigenous Southern Tuscany Cultivar Act as Anti-Inflammatory and Vasorelaxant Nutraceuticals.

Pozzetti L, Ferrara F, Marotta L, Gemma S, Butini S, Benedusi M Antioxidants (Basel). 2022; 11(3).

PMID: 35326088 PMC: 8944769. DOI: 10.3390/antiox11030437.

References

Busnena B, Foudah A, Melancon T, El Sayed K . Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer. Bioorg Med Chem. 2013; 21(7):2117-27. DOI: 10.1016/j.bmc.2012.12.050. View

Corominas-Faja B, Santangelo E, Cuyas E, Micol V, Joven J, Ariza X . Computer-aided discovery of biological activity spectra for anti-aging and anti-cancer olive oil oleuropeins. Aging (Albany NY). 2014; 6(9):731-41. PMC: 4221918. DOI: 10.18632/aging.100691. View

Abbattista R, Losito I, De Ceglie C, Basile G, Calvano C, Palmisano F . Structural characterization of the ligstroside aglycone isoforms in virgin olive oils by liquid chromatography-high-resolution Fourier-transform mass spectrometry and H/Dexchange. J Mass Spectrom. 2019; 54(10):843-855. DOI: 10.1002/jms.4438. View

Fabiani R, De Bartolomeo A, Rosignoli P, Servili M, Selvaggini R, Montedoro G . Virgin olive oil phenols inhibit proliferation of human promyelocytic leukemia cells (HL60) by inducing apoptosis and differentiation. J Nutr. 2006; 136(3):614-9. DOI: 10.1093/jn/136.3.614. View

Alessandri S, Ieri F, Romani A . Minor polar compounds in extra virgin olive oil: correlation between HPLC-DAD-MS and the Folin-Ciocalteu spectrophotometric method. J Agric Food Chem. 2014; 62(4):826-35. DOI: 10.1021/jf403104a. View

Gotsis E, Anagnostis P, Mariolis A, Vlachou A, Katsiki N, Karagiannis A . Health benefits of the Mediterranean Diet: an update of research over the last 5 years. Angiology. 2014; 66(4):304-18. DOI: 10.1177/0003319714532169. View

Jemai H, Bouaziz M, Fki I, El Feki A, Sayadi S . Hypolipidimic and antioxidant activities of oleuropein and its hydrolysis derivative-rich extracts from Chemlali olive leaves. Chem Biol Interact. 2008; 176(2-3):88-98. DOI: 10.1016/j.cbi.2008.08.014. View

Olmo-Cunillera A, Lopez-Yerena A, Lozano-Castellon J, Tresserra-Rimbau A, Vallverdu-Queralt A, Perez M . NMR spectroscopy: a powerful tool for the analysis of polyphenols in extra virgin olive oil. J Sci Food Agric. 2019; 100(5):1842-1851. DOI: 10.1002/jsfa.10173. View

Taticchi A, Esposto S, Veneziani G, Urbani S, Selvaggini R, Servili M . The influence of the malaxation temperature on the activity of polyphenoloxidase and peroxidase and on the phenolic composition of virgin olive oil. Food Chem. 2012; 136(2):975-83. DOI: 10.1016/j.foodchem.2012.08.071. View

10.

Carrasco-Pancorbo A, Neususs C, Pelzing M, Segura-Carretero A, Fernandez-Gutierrez A . CE- and HPLC-TOF-MS for the characterization of phenolic compounds in olive oil. Electrophoresis. 2007; 28(5):806-21. DOI: 10.1002/elps.200600382. View

11.

Ceci L, Mattar S, Carelli A . Chemical quality and oxidative stability of extra virgin olive oils from San Juan province (Argentina). Food Res Int. 2017; 100(Pt 1):764-770. DOI: 10.1016/j.foodres.2017.07.074. View

12.

Lozano-Castellon J, Lopez-Yerena A, de Alvarenga J, Romero Del Castillo-Alba J, Vallverdu-Queralt A, Escribano-Ferrer E . Health-promoting properties of oleocanthal and oleacein: Two secoiridoids from extra-virgin olive oil. Crit Rev Food Sci Nutr. 2019; 60(15):2532-2548. DOI: 10.1080/10408398.2019.1650715. View

13.

Guasch-Ferre M, Hu F, Martinez-Gonzalez M, Fito M, Bullo M, Estruch R . Olive oil intake and risk of cardiovascular disease and mortality in the PREDIMED Study. BMC Med. 2014; 12:78. PMC: 4030221. DOI: 10.1186/1741-7015-12-78. View

14.

Menendez J, Vazquez-Martin A, Garcia-Villalba R, Carrasco-Pancorbo A, Oliveras-Ferraros C, Fernandez-Gutierrez A . tabAnti-HER2 (erbB-2) oncogene effects of phenolic compounds directly isolated from commercial Extra-Virgin Olive Oil (EVOO). BMC Cancer. 2008; 8:377. PMC: 2626601. DOI: 10.1186/1471-2407-8-377. View

15.

Perez-Trujillo M, Gomez-Caravaca A, Segura-Carretero A, Fernandez-Gutierrez A, Parella T . Separation and identification of phenolic compounds of extra virgin olive oil from Olea europaea L. by HPLC-DAD-SPE-NMR/MS. Identification of a new diastereoisomer of the aldehydic form of oleuropein aglycone. J Agric Food Chem. 2013; 58(16):9129-36. DOI: 10.1021/jf101847e. View

16.

Polini B, Digiacomo M, Carpi S, Bertini S, Gado F, Saccomanni G . Oleocanthal and oleacein contribute to the in vitro therapeutic potential of extra virgin oil-derived extracts in non-melanoma skin cancer. Toxicol In Vitro. 2018; 52:243-250. DOI: 10.1016/j.tiv.2018.06.021. View

17.

Diamantakos P, Giannara T, Skarkou M, Melliou E, Magiatis P . Influence of Harvest Time and Malaxation Conditions on the Concentration of Individual Phenols in Extra Virgin Olive Oil Related to Its Healthy Properties. Molecules. 2020; 25(10). PMC: 7287853. DOI: 10.3390/molecules25102449. View

18.

Czerwinska M, Kiss A, Naruszewicz M . Inhibition of human neutrophils NEP activity, CD11b/CD18 expression and elastase release by 3,4-dihydroxyphenylethanol-elenolic acid dialdehyde, oleacein. Food Chem. 2014; 153:1-8. DOI: 10.1016/j.foodchem.2013.12.019. View

19.

Martinez-Gonzalez M, Estruch R, Corella D, Ros E, Salas-Salvado J . Prevention of diabetes with mediterranean diets. Ann Intern Med. 2014; 161(2):157-8. DOI: 10.7326/L14-5014-2. View

20.

Kanakis P, Termentzi A, Michel T, Gikas E, Halabalaki M, Skaltsounis A . From olive drupes to olive oil. An HPLC-orbitrap-based qualitative and quantitative exploration of olive key metabolites. Planta Med. 2013; 79(16):1576-87. DOI: 10.1055/s-0033-1350823. View