Defining the role of flavonoid structure on cottonseed oil stabilization: Study of A- and C-ring substitution

Tsimogiannis, D; Oreopoulou, V

dc.contributor.author	Tsimogiannis, D	en
dc.contributor.author	Oreopoulou, V	en
dc.date.accessioned	2014-03-01T01:26:04Z
dc.date.available	2014-03-01T01:26:04Z
dc.date.issued	2007	en
dc.identifier.issn	0003-021X	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/17918
dc.subject	(+)-catechin	en
dc.subject	Eriodictyol	en
dc.subject	Fisetin	en
dc.subject	Luteolin	en
dc.subject	Peroxide formation rate	en
dc.subject	Quercetin	en
dc.subject	Taxifolin	en
dc.subject.classification	Chemistry, Applied	en
dc.subject.classification	Food Science & Technology	en
dc.subject.other	Concentration (process)	en
dc.subject.other	Cotton	en
dc.subject.other	High performance liquid chromatography	en
dc.subject.other	Lipids	en
dc.subject.other	Oxidation	en
dc.subject.other	Peroxides	en
dc.subject.other	Eriodictyol	en
dc.subject.other	Fisetin	en
dc.subject.other	Luteolin	en
dc.subject.other	Peroxide formation rate	en
dc.subject.other	Quercetin	en
dc.subject.other	Taxifolin	en
dc.subject.other	Vegetable oils	en
dc.subject.other	Gossypium hirsutum	en
dc.subject.other	Micropus	en
dc.title	Defining the role of flavonoid structure on cottonseed oil stabilization: Study of A- and C-ring substitution	en
heal.type	journalArticle	en
heal.identifier.primary	10.1007/s11746-006-1016-2	en
heal.identifier.secondary	http://dx.doi.org/10.1007/s11746-006-1016-2	en
heal.language	English	en
heal.publicationDate	2007	en
heal.abstract	Structure-activity relationships of flavonoids against cottonseed oil oxidation are the objective of this work, which focuses on the contribution of C-ring and 5,7-di-OH A-ring. Flavonoids with a catecholic B-ring, namely quercetin, fisetin, luteolin, taxifolin, (+)-catechin and eriodictyol were added in increasing concentrations to cottonseed oil and the induced decrease in the rate constant of peroxide formation (k) and peroxide values (PV) were determined. The flavonoid depletion was monitored during the autoxidation with high-performance liquid chromatography-diode array detector (HPLC-DAD) analysis. The fully substituted C-ring was established as the most significant element for maximal antioxidant activity; quercetin even decreased k by 86% in comparison with the control and presented the highest decrease of PV per mmole of antioxidant. Flavonoids missing the 2,3-double bond or the 3-OH (taxifolin, luteolin) resulted in a smaller decrease of k, and the lack of both of the above structural elements (eriodictyol) resulted in the smallest decrease. Lack of the 4-carbonyl in the C-ring had the least negative effect on antioxidant activity since (+)-catechin presented the strongest protection after quercetin and fisetin. The activity of the latter flavonoid proved that A-ring hydroxyls, despite the unfavorable m-configuration, participate in the stabilization of the lipid substrate, although their significance was secondary. © 2007 AOCS.	en
heal.publisher	SPRINGER	en
heal.journalName	JAOCS, Journal of the American Oil Chemists' Society	en
dc.identifier.doi	10.1007/s11746-006-1016-2	en
dc.identifier.isi	ISI:000244399500004	en
dc.identifier.volume	84	en
dc.identifier.issue	2	en
dc.identifier.spage	129	en
dc.identifier.epage	136	en