Individual and Joint Effect of -Tocopherol and Hydroxytyrosol Acetate on the Oxidation of Sunflower Oil Submitted to Oxidative Conditions: A Study by Proton Nuclear Magnetic Resonance

Overview

Journal Antioxidants (Basel)

Date 2022 Jun 24

PMID 35740054

Authors

Sofia Del Cano-Ochoa

Ainhoa Ruiz-Aracama

Maria D Guillen

Affiliations

Soon will be listed here.

Abstract

This study tackles the individual and joint effect of -tocopherol and hydroxytyrosol acetate on the oxidation of sunflower oil submitted to accelerated storage conditions at intermediate temperature, in order to deepen the understanding of antioxidant-prooxidant behaviour. This was accomplished by H Nuclear Magnetic Resonance. For this purpose, the evolution of the degradation of both the main components of the oil and the aforementioned added compounds was monitored by this technique throughout the storage time. Furthermore, the formation of a very large number of oxylipins and the evolution of their concentration up to a very advanced stage of oil oxidation, as well as the occurrence of lipolysis, were also simultaneously studied. The results obtained show very clearly and thoroughly that in the oxidation process of the oil enriched in binary mixtures, interactions occur between -tocopherol and hydroxytyrosol acetate that notably reduce the antioxidant effect of the latter compound with the corresponding negative consequences that this entails. The methodology used here has proved to be very efficient to evaluate the antioxidant power of mixtures of compounds.

Citing Articles

Advancements in Biosensors for Lipid Peroxidation and Antioxidant Protection in Food: A Critical Review.

Daci M, Berisha L, Mercatante D, Rodriguez-Estrada M, Jin Z, Huang Y Antioxidants (Basel). 2025; 13(12.

PMID: 39765813 PMC: 11672933. DOI: 10.3390/antiox13121484.

References

Zarkovic N . 4-hydroxynonenal as a bioactive marker of pathophysiological processes. Mol Aspects Med. 2003; 24(4-5):281-91. DOI: 10.1016/s0098-2997(03)00023-2. View

Zhang W, Sun M, Salomon R . Preparative singlet oxygenation of linoleate provides doubly allylic dihydroperoxides: putative intermediates in the generation of biologically active aldehydes in vivo. J Org Chem. 2006; 71(15):5607-15. DOI: 10.1021/jo0605795. View

Sottero B, Rossin D, Poli G, Biasi F . Lipid Oxidation Products in the Pathogenesis of Inflammation-related Gut Diseases. Curr Med Chem. 2017; 25(11):1311-1326. DOI: 10.2174/0929867324666170619104105. View

Harry-Okuru R, Carriere C . Synthesis, rheological characterization, and constitutive modeling of polyhydroxy triglycerides derived from milkweed oil. J Agric Food Chem. 2002; 50(11):3214-21. DOI: 10.1021/jf011464z. View

Zheng J, Plopper C, Lakritz J, Storms D, Hammock B . Leukotoxin-diol: a putative toxic mediator involved in acute respiratory distress syndrome. Am J Respir Cell Mol Biol. 2001; 25(4):434-8. DOI: 10.1165/ajrcmb.25.4.4104. View

Frankel E, Neff W, Selke E, Weisleder D . Photosensitized oxidation of methyl linoleate: Secondary and volatile thermal decomposition products. Lipids. 2016; 17(1):11-8. DOI: 10.1007/BF02535116. View

Burstyn P, Horrobin D . Possible mechanism of action for aldosterone-induced hypertension. Lancet. 1970; 1(7654):973-6. DOI: 10.1016/s0140-6736(70)91099-8. View

Schneider C, Porter N, Brash A . Autoxidative transformation of chiral omega6 hydroxy linoleic and arachidonic acids to chiral 4-hydroxy-2E-nonenal. Chem Res Toxicol. 2004; 17(7):937-41. DOI: 10.1021/tx049913n. View

Cao G, Alessio H, Cutler R . Oxygen-radical absorbance capacity assay for antioxidants. Free Radic Biol Med. 1993; 14(3):303-11. DOI: 10.1016/0891-5849(93)90027-r. View

10.

Honn K, Nelson K, Renaud C, Bazaz R, Diglio C, Timar J . Fatty acid modulation of tumor cell adhesion to microvessel endothelium and experimental metastasis. Prostaglandins. 1992; 44(5):413-29. DOI: 10.1016/0090-6980(92)90137-i. View

11.

Mateos R, Dominguez M, Espartero J, Cert A . Antioxidant effect of phenolic compounds, alpha-tocopherol, and other minor components in virgin olive oil. J Agric Food Chem. 2003; 51(24):7170-5. DOI: 10.1021/jf034415q. View

12.

Schwarzer E, Arese P, Skorokhod O . Role of the lipoperoxidation product 4-hydroxynonenal in the pathogenesis of severe malaria anemia and malaria immunodepression. Oxid Med Cell Longev. 2015; 2015:638416. PMC: 4417603. DOI: 10.1155/2015/638416. View

13.

Blair I . Lipid hydroperoxide-mediated DNA damage. Exp Gerontol. 2001; 36(9):1473-81. DOI: 10.1016/s0531-5565(01)00133-4. View

14.

Keyes G, Maiden K, Ramsden C . Stable analogs of 13‑hydroxy-9,10-trans-epoxy-(11E)-octadecenoate (13,9-HEL), an oxidized derivative of linoleic acid implicated in the epidermal skin barrier. Prostaglandins Leukot Essent Fatty Acids. 2021; 174:102357. PMC: 8595794. DOI: 10.1016/j.plefa.2021.102357. View

15.

Moghaddam M, Grant D, CHEEK J, Greene J, Williamson K, Hammock B . Bioactivation of leukotoxins to their toxic diols by epoxide hydrolase. Nat Med. 1997; 3(5):562-6. PMC: 7095900. DOI: 10.1038/nm0597-562. View

16.

Martin-Rubio A, Sopelana P, Nakashima F, Shibata T, Uchida K, Guillen M . A Dual Perspective of the Action of Lysine on Soybean Oil Oxidation Process Obtained by Combining H NMR and LC-MS: Antioxidant Effect and Generation of Lysine-Aldehyde Adducts. Antioxidants (Basel). 2019; 8(9). PMC: 6770364. DOI: 10.3390/antiox8090326. View

17.

Benzie I, Strain J . The ferric reducing ability of plasma (FRAP) as a measure of "antioxidant power": the FRAP assay. Anal Biochem. 1996; 239(1):70-6. DOI: 10.1006/abio.1996.0292. View

18.

Patwardhan A, Scotland P, Akopian A, Hargreaves K . Activation of TRPV1 in the spinal cord by oxidized linoleic acid metabolites contributes to inflammatory hyperalgesia. Proc Natl Acad Sci U S A. 2009; 106(44):18820-4. PMC: 2764734. DOI: 10.1073/pnas.0905415106. View

19.

Gardner H, Hamberg M . Oxygenation of (3Z)-nonenal to (2E)-4-hydroxy-2-nonenal in the broad bean (Vicia faba L.). J Biol Chem. 1993; 268(10):6971-7. View

20.

Poljsak B, Kovac V, Milisav I . Antioxidants, Food Processing and Health. Antioxidants (Basel). 2021; 10(3). PMC: 8001021. DOI: 10.3390/antiox10030433. View