Long chain fatty acid acylated derivatives of Quercetin-3-O-glucoside as antioxidants to prevent lipid oxidation

Biomolecules

Volumn 4, Issue 4, 2014, Pages 980-993

  Warnakulasuriya, Sumudu N ^a   Ziaullah, ^a   Rupasinghe, H P Vasantha ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

Author keywords

Antioxidant; Fatty acids; LDL oxidation; Lipid oxidation; Q3G esters

Indexed keywords

ANTIOXIDANT; CUPRIC ION; DOCOSAHEXAENOIC ACID; FISH OIL; ICOSAPENTAENOIC ACID; ISOQUERCITRIN; LINOLEIC ACID; LINOLENIC ACID; LIPASE B; LONG CHAIN FATTY ACID; LONG CHAIN FATTY ACID ACYLATED DERIVATIVE OF QUERCETIN 3 O GLUCOSIDE; OLEIC ACID; STEARIC ACID; THIOBARBITURIC ACID REACTIVE SUBSTANCE; UNCLASSIFIED DRUG; WATER OIL CREAM; COPPER; FATTY ACID; FLAVONOID; FUNGAL PROTEIN; LIPASE B, CANDIDA ANTARCTICA; LOW DENSITY LIPOPROTEIN; QUERCETIN; TRIACYLGLYCEROL LIPASE; UNSATURATED FATTY ACID;

ANTIOXIDANT ACTIVITY; ARTICLE; BIOCATALYST; CANDIDA ANTARCTICA; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; ESTERIFICATION; HUMAN; LIPID OXIDATION; OXIDATIVE STRESS; PROTEIN CONTENT; THIN LAYER CHROMATOGRAPHY; ACYLATION; ANALOGS AND DERIVATIVES; CHEMISTRY; DRUG EFFECTS; LIPID METABOLISM; METABOLISM;

ACYLATION; ANTIOXIDANTS; COPPER; FATTY ACIDS; FATTY ACIDS, UNSATURATED; FISH OILS; FLAVONOIDS; FUNGAL PROTEINS; HUMANS; LIPASE; LIPID METABOLISM; LIPOPROTEINS, LDL; QUERCETIN;

EID: 84964314762     PISSN: None     EISSN: 2218273X     Source Type: Journal    
DOI: 10.3390/biom4040980     Document Type: Article

References (37)

1. Russo, G.L. Dietary n-6 and n-3 polyunsaturated fatty acids: From biochemistry to clinical implications in cardiovascular prevention. Biochem. Pharmacol. 2009, 77, 937-946.
2. Sun, Y.; Wang, W.; Chen, H.; Li, C. Autoxidation of unsaturated lipids in food emulsion. Crit. Rev. Food Sci. Nutr. 2011, 5, 453-466.
3. Kathirvel, P.; Rupasinghe, H.P.V. Plant-derived antioxidants as potential omega-3 PUFA stabilizers. In Fish Oil: Production, Consumption and Health Benefits; Dijk, M.V., Vitel, J., Eds.; Nova Science Publishers USA: Hauppauge, NY, USA, 2011; pp. 143-154.
4. Kanner, J. Dietary advance lipid oxidation end products are risk factors to human health. Mol. Nutr. Food Res. 2007, 51, 1094-1101.
5. Katsube, T.; Imawaka, N.; Kawano, Y.; Yamazaki, Y.; Shiwaku, L.; Yamane, Y. Antioxidant flavonol glycosides in mulberry (Morus alba L.) leaves isolated based on LDL antioxidant activity. Food Chem. 2006, 97, 25-31.
6. Chalas, J.; Claise, C.; Edeas, M.; Messaoudi, C.; Vergnes, L.; Abella, A.; Lindenbaum, A. Effect of ethyl esterification of phenolic acids on low-density lipoprotein oxidation. Biomed. Pharmacother. 2001, 55, 54-60.
7. Salem, J.H.; Chevalot, I.; Harscoat-Schiavo, C.; Paris, C.; Fick, M.; Humeau, C. Biological activities of flavonoids from Nitraria retusa (Forssk.) Asch. and their acylated derivatives. Food Chem. 2011, 124, 486-494.
8. Lue, B.M.; Guo, Z.; Xu, X. Effect of room temperature ionic liquid structure on the enzymatic acylation of flavonoids. Process Biochem. 2010, 45, 1375-1382.
9. Montenegro, L.; Carbone, C.; Maniscalco, C.; Lambusta, D.; Nicolosi, G.; Ventura, C.A.; Puglisi, G. In vitro evaluation of quercetin-3-O-acyl esters as topical prodrugs. Int. J. Pharm. 2007, 336, 257-262.
10. Mellou, F.; Lazari, D.; Skattsa, H.; Tselepis, A.D.; Kolisis, F.N.; Stamatis, H. Biocatalytic preparation of acylated derivatives of flavonoid glycosides enhances their antioxidant and antimicrobial activity. J. Biotechnol. 2005, 116, 295-304.
11. Laguerre, M.; Bayrasy, C.; Lecomte, J.; Chabi, B.; Decker, E.A.; Wrutniak-Cabello, C.; Cabello, G.; Villeneuve, P. How to boost antioxidants by lipophilization? Biochimie 2013, 95, 20-26.
12. Chebil, L.; Humeau, C.; Falcimaigne, A.; Engasser, J.M.; Ghoul, M. Review: Enzymatic acylation of flavonoids. Process Biochem. 2006, 41, 2237-2251.
13. Ardhaoui, M.; Falcimaigne, A.; Ognier, S.; Engasser, J.M.; Moussou, P.; Pauly, G.; Ghoul, M. Effect of acyl donor chain length and substitutions pattern on the enzymatic acylation of flavonoids. J. Biotechnol. 2004, 110, 256-271.
14. Ziaullah; Bhullar, K.S.; Warnakulasuriya, S.N.; Rupasinghe, H.P.V. Biocatalytic synthesis, structural elucidation, antioxidant capacity and tyrosinase inhibition activity of long chain fatty acid acylated derivatives of phloridzin and isoquercitrin. Bioorg. Med. Chem. 2013, 21, 684-692.
15. Official Methods and Recommended Practices of the American Oil Chemists' Society Method Cd 8-53; Firestone, D., Ed.; American Oil Chemists' Society Champaign: Urbana, IL, USA, 1997.
16. Rupasinghe, H.P.V.; Erkan, N.; Yasmin, A. Antioxidant protection of eicosapentaenoic acid and fish oil oxidation by polyphenolic-enriched apple skin extract. J. Agric. Food Chem. 2010, 58, 1233-1239.
17. Huber, G.M.; Rupasinghe, H.P.V.; Shahidi, F. Inhibition of oxidation of omega-3 polyunsaturated fatty acids and fish oil by quercetin glycosides. Food Chem. 2009, 117, 290-295.
18. Thilakarathna, S.H.; Rupasinghe, H.P.V. Anti-atherosclerotic effects of fruit bioactive compounds: A review of current scientific evidence. Can. J. Plant Sci. 2012, 92, 407-419.
19. Lowry, O.H.; Rosebrough, N.J.; Farr, A.L.; Randall, R.J. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 1951, 193, 165-275.
20. Xu, B.J.; Yuan, S.H.; Chang, S.K.C. Comparative studies on the antioxidant activities of nine common food legumes against copper induced LDL oxidation in vitro. J. Food Sci. 2007, 72, 522-527.
21. Danihelova, M.; Viskupičova, J.; Šturdika, E. Lipophilization of flavonoids for their food, therapeutic and cosmetic applications. Acta Chim. Slovaca 2012, 5, 59-69.
22. Passicos, E.; Santarelli, X.; Coulon, D. Regioselective acylation of flavonoids catalyzed by immobilized Candida antarctica lipase under reduced pressure. Biotechnol. Lett. 2004, 26, 1073-1076.
23. Lorentz, C.; Dulac, A.; Pencreach, G.; Ergan, F.; Richomme, P.; Soultani-Vigneron, S. Lipase-catalyzed synthesis of two new antioxidants: 4-O- and 3-O-palmitoyl chlorogenic acids. Biotechnol. Lett. 2010, 32, 1955-1960.
24. Chebil, L.; Anthoni, J.; Humeau, C.; Gerardin, C.; Engasser, J.M.; Goul, M. Enzymatic acylation of flavonoids: Effect of the nature of the substrate, origin of lipase and operating conditions on conversion yield and regioselectivity. J. Agric. Food Chem. 2007, 55, 9496-9502.
25. 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. J. Agric. Food Chem. 2000, 48, 2122-2126.
26. Viskupicova, J.; Danihelova, M.; Ondrejovic, M.; Liptaj, T.; Sturdik, E. Lipophilic rutin derivatives for antioxidant protection of oil-based foods. Food Chem. 2010, 123, 45-55.
27. Sharma, O.P.; Bhat, T.K. DPPH antioxidant assay revisited. Food Chem. 2009, 113, 1202-1205.
28. Porter, W.L. Recent trends in food applications of antioxidants. In Autoxidation in Food and Biological Systems; Simic, M.G., Karel, M., Eds.; Plenum Press: New York, NY, USA, 1980; pp. 295-365.
29. Frankel, E.N. Antioxidants in lipid foods and their impact on food quality. Food Chem. 1996, 57, 51-55.
30. Shahidi, F.; Zhong, Y. Revisiting the polar paradox theory: A critical overview. J. Agric. Food Chem. 2011, 59, 3499-3504.
31. Chaiyasit, W.; Elias, R.J.; McClements, D.J.; Decker, E.A. Role of physical structures in bulk oils on lipid oxidation. Crit. Rev. Food Sci. Nutr. 2007, 47, 299-317.
32. Mateos, R.; Trujillo, M.; Pereira-Caro, G.; Madrona, A.; Cert, A.; Espartero, J.L. New lipophilic tyrosyl esters: Comparative antioxidant evaluation with hydroxytyrosyl esters. J. Agric. Food Chem. 2008, 56, 10960-10966.
33. Frankel, E.N.; Kanner, J.; German, J.B.; Parks, E.; Kinsella, J.E. Inhibition of oxidation of human low-density lipoprotein by phenolic substances in red wine. Lancet 1993, 341, 454-457.
34. Safari, M.; Sheikh, N. Effects of flavonoids on the susceptibility of low-density lipoprotein to oxidative modification. Prostaglandins Leukot. Essent. Fatty Acids 2003, 69, 73-77.
35. Thilakarathna, S.H.; Rupasinghe, H.P.V.; Needs, P.W. Apple peel bioactive rich extracts effectively inhibit in vitro human LDL oxidation. Food Chem. 2013, 138, 463-470.
36. Miyagi, Y.; Miwa, K.; Inoue, H. Inhibition of human low-density lipoprotein oxidation by flavonoids in red wine and grape juice. Am. J. Cardiol. 1997, 80, 1627-1631.
37. Kerry, N.; Abbey, M. Red wine and fractionated phenolic compounds prepared from red wine inhibit low density lipoprotein oxidation in vitro. Atherosclerosis 1997, 135, 93-102.