Antioxidant properties of tyrosol and hydroxytyrosol saturated fatty acid esters

Food Chemistry

Volumn 245, Issue , 2018, Pages 1262-1268

  Sun, Yuanxin ^a   Zhou, Dayong ^a,b   Shahidi, Fereidoon ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

^b DALIAN POLYTECHNIC UNIVERSITY   (China)

Author keywords

Antioxidant activity; Enzymatic synthesis; Esters; Hydroxytyrosol; Saturated fatty acids (SFA); Tyrosol

Indexed keywords

HYDROXYTYROSOL; TYROSOL;

ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG PURIFICATION; DRUG SCREENING;

EID: 85037642112     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2017.11.051     Document Type: Article

References (37)

1. Ambigaipalan, P., Shahidi, F., Antioxidant potential of date (Phoenix dactylifera L.) seed protein hydrolysates and carnosine in food and biological systems. Journal of Agricultural and Food Chemistry 63:3 (2015), 864–871.
2. Aust, S.D., Svingen, B.A., The role of iron in enzymatic lipid peroxidation. Free Radicals in Biology 5 (1982), 1–28.
3. Bayrasy, C., Chabi, B., Laguerre, M., Lecomte, J., Jublanc, É., Villeneuve, P., et al. Boosting antioxidants by lipophilization: A strategy to increase cell uptake and target mitochondria. Pharmaceutical Research 30:8 (2013), 1979–1989.
4. Bernini, R., Merendino, N., Romani, A., Velotti, F., Naturally occurring hydroxytyrosol: Synthesis and anticancer potential. Current Medicinal Chemistry 20:5 (2013), 655–670.
5. Bernini, R., Mincione, E., Barontini, M., Crisante, F., Convenient synthesis of hydroxytyrosol and its lipophilic derivatives from tyrosol or homovanillyl alcohol. Journal of Agricultural and Food Chemistry 56:19 (2008), 8897–8904.
6. Braude, E.A., Brook, A.G., Linstead, R.P., Hydrogen transfer. Part V. Dehydrogenation reactions with diphenylpicrylhydrazyl. Journal of the Chemical Society (Resumed), 1954, 3574–3578.
7. Carrasco-Pancorbo, A., Cerretani, L., Bendini, A., Segura-Carretero, A., Del Carlo, M., Gallina-Toschi, T., et al. Evaluation of the antioxidant capacity of individual phenolic compounds in virgin olive oil. Journal of Agricultural and Food Chemistry 53:23 (2005), 8918–8925.
8. Crauste, C., Rosell, M., Durand, T., Vercauteren, J., Omega-3 polyunsaturated lipophenols, how and why?. Biochimie 120 (2016), 62–74.
9. de Pinedo, A.T., Peñalver, P., Pérez-Victoria, I., Rondón, D., Morales, J.C., Synthesis of new phenolic fatty acid esters and their evaluation as lipophilic antioxidants in an oil matrix. Food Chemistry 105:2 (2007), 657–665.
10. Di Benedetto, R., Varì, R., Scazzocchio, B., Filesi, C., Santangelo, C., Giovannini, C., et al. Tyrosol, the major extra virgin olive oil compound, restored intracellular antioxidant defences in spite of its weak antioxidative effectiveness. Nutrition, Metabolism and Cardiovascular Diseases 17:7 (2007), 535–545.
11. Goupy, P., Dufour, C., Loonis, M., Dangles, O., Quantitative kinetic analysis of hydrogen transfer reactions from dietary polyphenols to the DPPH radical. Journal of Agricultural and Food Chemistry 51:3 (2003), 615–622.
12. Grasso, S., Siracusa, L., Spatafora, C., Renis, M., Tringali, C., Hydroxytyrosol lipophilic analogues: Enzymatic synthesis, radical scavenging activity and DNA oxidative damage protection. Bioorganic Chemistry 35:2 (2007), 137–152.
13. Hiramoto, K., Ojima, N., Sako, K.I., Kikugawa, K., Effect of plant phenolics on the formation of the spin-adduct of hydroxyl radical and the DNA strand breaking by hydroxyl radical. Biological and Pharmaceutical Bulletin 19:4 (1996), 558–563.
14. Jakovetić, S.M., Jugović, B.Z., Gvozdenović, M.M., Bezbradica, D.I., Antov, M.G., Mijin, D.Ž., et al. Synthesis of aliphatic esters of cinnamic acid as potential lipophilic antioxidants catalyzed by lipase B from Candida antarctica. Applied Biochemistry and Biotechnology 170:7 (2013), 1560–1573.
15. Kedare, S.B., Singh, R.P., Genesis and development of DPPH method of antioxidant assay. Journal of Food Science and Technology 48:4 (2011), 412–422.
16. Khymenets, O., Fitó, M., Touriño, S., Muñoz-Aguayo, D., Pujadas, M., Torres, J.L., et al. Antioxidant activities of hydroxytyrosol main metabolites do not contribute to beneficial health effects after olive oil ingestion. Drug Metabolism and Disposition 38:9 (2010), 1417–1421.
17. Liao, X., Lu, Z., Zhang, M., Liu, X., Shi, B., Adsorption of Cu (II) from aqueous solutions by tannins immobilized on collagen. Journal of Chemical Technology and Biotechnology 79:4 (2004), 335–342.
18. Lin, C.N., Chen, H.L., Yen, M.H., Flavonoids with DNA strand-scission activity from Rhos Jaranica var. roxburghiana. Fitoterapia 79:1 (2008), 32–36.
19. Lucas, R., Comelles, F., Alcántara, D., Maldonado, O.S., Curcuroze, M., Parra, J.L., et al. Surface-active properties of lipophilic antioxidants tyrosol and hydroxytyrosol fatty acid esters: A potential explanation for the nonlinear hypothesis of the antioxidant activity in oil-in-water emulsions. Journal of Agricultural and Food Chemistry 58:13 (2010), 8021–8026.
20. Madrona, A., Pereira-Caro, G., Mateos, R., Rodríguez, G., Trujillo, M., Fernández-Bolaños, J., et al. Synthesis of hydroxytyrosyl alkyl ethers from olive oil waste waters. Molecules 14:5 (2009), 1762–1772.
21. Mateos, R., Trujillo, M., Pereira-Caro, G., Madrona, A., Cert, A., Espartero, J.L., New lipophilic tyrosyl esters. Comparative antioxidant evaluation with hydroxytyrosyl esters. Journal of Agricultural and Food Chemistry 56:22 (2008), 10960–10966.
22. Orrenius, S., Gogvadze, V., Zhivotovsky, B., Mitochondrial oxidative stress: Implications for cell death. Annual Review of Pharmacology and Toxicology 47 (2007), 143–183.
23. Perron, N.R., Hodges, J.N., Jenkins, M., Brumaghim, J.L., Predicting how polyphenol antioxidants prevent DNA damage by binding to iron. Inorganic Chemistry 47:14 (2008), 6153–6161.
24. Porter, W.L., Paradoxical behavior of antioxidants in food and biological systems. Toxicology and Industrial Health, 9(1–2), 1993, 93.
25. Roleira, F.M., Siquet, C., Orrù, E., Garrido, E.M., Garrido, J., Milhazes, N., et al. Lipophilic phenolic antioxidants: Correlation between antioxidant profile, partition coefficients and redox properties. Bioorganic & Medicinal Chemistry 18:16 (2010), 5816–5825.
26. Salem, J.H., Humeau, C., Chevalot, I., Harscoat-Schiavo, C., Vanderesse, R., Blanchard, F., et al. Effect of acyl donor chain length on isoquercitrin acylation and biological activities of corresponding esters. Process Biochemistry 45:3 (2010), 382–389.
27. Shahidi, F., Zhong, Y., Measurement of antioxidant activity. Journal of Functional Foods 18 (2015), 757–781.
28. Silva, F.A., Borges, F., Guimarães, C., Lima, J.L., Matos, C., Reis, S., Phenolic acids and derivatives: Studies on the relationship among structure, radical scavenging activity, and physicochemical parameters. Journal of Agricultural and Food Chemistry 48:6 (2000), 2122–2126.
29. Steinberg, D., Witztum, J.L., Oxidized low-density lipoprotein and atherosclerosis. Arteriosclerosis, Thrombosis, and Vascular Biology 30:12 (2010), 2311–2316.
30. Tan, J.B.L., Lim, Y.Y., Critical analysis of current methods for assessing the in vitro antioxidant and antibacterial activity of plant extracts. Food Chemistry 172 (2015), 814–822.
31. Tofani, D., Balducci, V., Gasperi, T., Incerpi, S., Gambacorta, A., Fatty acid hydroxytyrosyl esters: Structure/antioxidant activity relationship by ABTS and in cell-culture DCF assays. Journal of Agricultural and Food Chemistry 58 (2010), 5292–5299.
32. Trujillo, M., Mateos, R., Collantes de Teran, L., Espartero, J.L., Cert, R., Jover, M., et al. Lipophilic hydroxytyrosyl esters. Antioxidant activity in lipid matrices and biological systems. Journal of Agricultural and Food Chemistry 54:11 (2006), 3779–3785.
33. Vivancos, M., Moreno, J.J., Effect of resveratrol, tyrosol and-sitosterol on oxidised low-density lipoprotein-stimulated oxidative stress, arachidonic acid release and prostaglandin E2 synthesis by RAW 264.7 macrophages. British Journal of Nutrition 99:6 (2008), 1199–1207.
34. Vlachogianni, I.C., Fragopoulou, E., Kostakis, I.K., Antonopoulou, S., In vitro assessment of antioxidant activity of tyrosol, resveratrol and their acetylated derivatives. Food Chemistry 177 (2015), 165–173.
35. Wang, J., Shahidi, F., Acidolysis of p-coumaric acid with omega-3 oils and antioxidant activity of phenolipid products in in vitro and biological model systems. Journal of Agricultural and Food Chemistry 62:2 (2013), 454–461.
36. Yamada, K., Ogawa, H., Hara, A., Yoshida, Y., Yonezawa, Y., Karibe, K., et al. Mechanism of the antiviral effect of hydroxytyrosol on influenza virus appears to involve morphological change of the virus. Antiviral Research 83:1 (2009), 35–44.
37. Zhong, Y., Shahidi, F., Lipophilised epigallocatechin gallate (EGCG) derivatives and their antioxidant potential in food and biological systems. Food Chemistry 131:1 (2012), 22–30.