Structure-Biological Activity Relationships of Extra-Virgin Olive Oil Phenolic Compounds: Health Properties and Bioavailability

Overview

Journal Antioxidants (Basel)

Date 2020 Aug 6

PMID 32752213

Citations 29

Authors

Paloma Rodriguez-Lopez

Jesus Lozano-Sanchez

Isabel Borras-Linares

Tatiana Emanuelli

Javier A Menendez

Antonio Segura-Carretero

Affiliations

Soon will be listed here.

Abstract

Extra-virgin olive oil is regarded as functional food since epidemiological studies and multidisciplinary research have reported convincing evidence that its intake affects beneficially one or more target functions in the body, improves health, and reduces the risk of disease. Its health properties have been related to the major and minor fractions of extra-virgin olive oil. Among olive oil chemical composition, the phenolic fraction has received considerable attention due to its bioactivity in different chronic diseases. The bioactivity of the phenolic compounds could be related to different properties such as antioxidant and anti-inflammatory, although the molecular mechanism of these compounds in relation to many diseases could have different cellular targets. The aim of this review is focused on the extra-virgin olive oil phenolic fraction with particular emphasis on (a) biosynthesis, chemical structure, and influence factors on the final extra-virgin olive oil phenolic composition; (b) structure-antioxidant activity relationships and other molecular mechanisms in relation to many diseases; (c) bioavailability and controlled delivery strategies; (d) alternative sources of olive biophenols. To achieve this goal, a comprehensive review was developed, with particular emphasis on in vitro and in vivo assays as well as clinical trials. This report provides an overview of extra-virgin olive oil phenolic compounds as a tool for functional food, nutraceutical, and pharmaceutical applications.

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References

Lozano-Sanchez J, Giambanelli E, Quirantes-Pine R, Cerretani L, Bendini A, Segura-Carretero A . Wastes generated during the storage of extra virgin olive oil as a natural source of phenolic compounds. J Agric Food Chem. 2011; 59(21):11491-500. DOI: 10.1021/jf202596q. View

Del Rio D, Rodriguez-Mateos A, Spencer J, Tognolini M, Borges G, Crozier A . Dietary (poly)phenolics in human health: structures, bioavailability, and evidence of protective effects against chronic diseases. Antioxid Redox Signal. 2012; 18(14):1818-92. PMC: 3619154. DOI: 10.1089/ars.2012.4581. View

Sanchez-Fidalgo S, Villegas I, Aparicio-Soto M, Cardeno A, Rosillo M, Gonzalez-Benjumea A . Effects of dietary virgin olive oil polyphenols: hydroxytyrosyl acetate and 3, 4-dihydroxyphenylglycol on DSS-induced acute colitis in mice. J Nutr Biochem. 2015; 26(5):513-20. DOI: 10.1016/j.jnutbio.2014.12.001. View

Franconi F, Coinu R, Carta S, Urgeghe P, Ieri F, Mulinacci N . Antioxidant effect of two virgin olive oils depends on the concentration and composition of minor polar compounds. J Agric Food Chem. 2006; 54(8):3121-5. DOI: 10.1021/jf053003+. View

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

Khymenets O, Fito M, Tourino S, Munoz-Aguayo D, Pujadas M, Torres J . Antioxidant activities of hydroxytyrosol main metabolites do not contribute to beneficial health effects after olive oil ingestion. Drug Metab Dispos. 2010; 38(9):1417-21. DOI: 10.1124/dmd.110.032821. View

Calabriso N, Massaro M, Scoditti E, DAmore S, Gnoni A, Pellegrino M . Extra virgin olive oil rich in polyphenols modulates VEGF-induced angiogenic responses by preventing NADPH oxidase activity and expression. J Nutr Biochem. 2016; 28:19-29. DOI: 10.1016/j.jnutbio.2015.09.026. View

Baci D, Gallazzi M, Cascini C, Tramacere M, De Stefano D, Bruno A . Downregulation of Pro-Inflammatory and Pro-Angiogenic Pathways in Prostate Cancer Cells by a Polyphenol-Rich Extract from Olive Mill Wastewater. Int J Mol Sci. 2019; 20(2). PMC: 6359159. DOI: 10.3390/ijms20020307. View

Romani A, Ieri F, Urciuoli S, Noce A, Marrone G, Nediani C . Health Effects of Phenolic Compounds Found in Extra-Virgin Olive Oil, By-Products, and Leaf of L. Nutrients. 2019; 11(8). PMC: 6724211. DOI: 10.3390/nu11081776. View

10.

de Bock M, Thorstensen E, Derraik J, Henderson H, Hofman P, Cutfield W . Human absorption and metabolism of oleuropein and hydroxytyrosol ingested as olive (Olea europaea L.) leaf extract. Mol Nutr Food Res. 2013; 57(11):2079-85. DOI: 10.1002/mnfr.201200795. View

11.

Parkinson L, Cicerale S . The Health Benefiting Mechanisms of Virgin Olive Oil Phenolic Compounds. Molecules. 2016; 21(12). PMC: 6273500. DOI: 10.3390/molecules21121734. View

12.

Vitaglione P, Savarese M, Paduano A, Scalfi L, Fogliano V, Sacchi R . Healthy virgin olive oil: a matter of bitterness. Crit Rev Food Sci Nutr. 2014; 55(13):1808-18. DOI: 10.1080/10408398.2012.708685. View

13.

Toric J, Karkovic Markovic A, Jakobusic Brala C, Barbaric M . Anticancer effects of olive oil polyphenols and their combinations with anticancer drugs. Acta Pharm. 2019; 69(4):461-482. DOI: 10.2478/acph-2019-0052. View

14.

Kalampaliki A, Giannouli V, Skaltsounis A, Kostakis I . A Three-Step, Gram-Scale Synthesis of Hydroxytyrosol, Hydroxytyrosol Acetate, and 3,4-Dihydroxyphenylglycol. Molecules. 2019; 24(18). PMC: 6767028. DOI: 10.3390/molecules24183239. View

15.

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

16.

Marcelino G, Hiane P, Freitas K, Santana L, Pott A, Donadon J . Effects of Olive Oil and Its Minor Components on Cardiovascular Diseases, Inflammation, and Gut Microbiota. Nutrients. 2019; 11(8). PMC: 6722810. DOI: 10.3390/nu11081826. View

17.

Esposto S, Selvaggini R, Taticchi A, Veneziani G, Sordini B, Servili M . Quality evolution of extra-virgin olive oils according to their chemical composition during 22 months of storage under dark conditions. Food Chem. 2019; 311:126044. DOI: 10.1016/j.foodchem.2019.126044. View

18.

Nieto G, Martinez L, Castillo J, Ros G . Hydroxytyrosol extracts, olive oil and walnuts as functional components in chicken sausages. J Sci Food Agric. 2017; 97(11):3761-3771. DOI: 10.1002/jsfa.8240. View

19.

Bouallagui Z, Han J, Isoda H, Sayadi S . Hydroxytyrosol rich extract from olive leaves modulates cell cycle progression in MCF-7 human breast cancer cells. Food Chem Toxicol. 2010; 49(1):179-84. DOI: 10.1016/j.fct.2010.10.014. View

20.

Giordano E, Davalos A, Visioli F . Chronic hydroxytyrosol feeding modulates glutathione-mediated oxido-reduction pathways in adipose tissue: a nutrigenomic study. Nutr Metab Cardiovasc Dis. 2014; 24(10):1144-50. DOI: 10.1016/j.numecd.2014.05.003. View