Biocatalytic preparation of acylated derivatives of flavonoid glycosides enhances their antioxidant and antimicrobial activity

Mellou, F; Lazari, D; Skaltsa, H; Tselepis, AD; Kolisis, FN; Stamatis, H

dc.contributor.author	Mellou, F	en
dc.contributor.author	Lazari, D	en
dc.contributor.author	Skaltsa, H	en
dc.contributor.author	Tselepis, AD	en
dc.contributor.author	Kolisis, FN	en
dc.contributor.author	Stamatis, H	en
dc.date.accessioned	2014-03-01T01:21:54Z
dc.date.available	2014-03-01T01:21:54Z
dc.date.issued	2005	en
dc.identifier.issn	0168-1656	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/16408
dc.subject	Antioxidants	en
dc.subject	Biocatalysis	en
dc.subject	Esterification	en
dc.subject	Flavonoids	en
dc.subject	LDL oxidation	en
dc.subject	Lipase	en
dc.subject.classification	Biotechnology & Applied Microbiology	en
dc.subject.other	Acetone	en
dc.subject.other	Acylation	en
dc.subject.other	Antioxidants	en
dc.subject.other	Biocatalysts	en
dc.subject.other	Derivatives	en
dc.subject.other	Enzymes	en
dc.subject.other	Organic solvents	en
dc.subject.other	Synthesis (chemical)	en
dc.subject.other	Biocatalytic preparation	en
dc.subject.other	Enzymatic synthesis	en
dc.subject.other	Flavonoid glycosid	en
dc.subject.other	Molar ratio	en
dc.subject.other	Carbohydrates	en
dc.subject.other	acetone	en
dc.subject.other	alcohol	en
dc.subject.other	antiinfective agent	en
dc.subject.other	antioxidant	en
dc.subject.other	aurantiin	en
dc.subject.other	disaccharide	en
dc.subject.other	flavanoid	en
dc.subject.other	fungal enzyme	en
dc.subject.other	glucopyranoside	en
dc.subject.other	glucose	en
dc.subject.other	glycoside	en
dc.subject.other	lauric acid derivative	en
dc.subject.other	lauric acid vinyl ester	en
dc.subject.other	low density lipoprotein	en
dc.subject.other	monosaccharide	en
dc.subject.other	organic solvent	en
dc.subject.other	triacylglycerol lipase	en
dc.subject.other	unclassified drug	en
dc.subject.other	acylation	en
dc.subject.other	antimicrobial activity	en
dc.subject.other	antioxidant activity	en
dc.subject.other	article	en
dc.subject.other	biocatalyst	en
dc.subject.other	Candida antarctica	en
dc.subject.other	controlled study	en
dc.subject.other	enzyme synthesis	en
dc.subject.other	Gram negative bacterium	en
dc.subject.other	Gram positive bacterium	en
dc.subject.other	human	en
dc.subject.other	medicinal plant	en
dc.subject.other	nonhuman	en
dc.subject.other	priority journal	en
dc.subject.other	Acylation	en
dc.subject.other	Anti-Bacterial Agents	en
dc.subject.other	Antioxidants	en
dc.subject.other	Bacteria	en
dc.subject.other	Catalysis	en
dc.subject.other	Cholesterol, LDL	en
dc.subject.other	Enzymes, Immobilized	en
dc.subject.other	Flavonoids	en
dc.subject.other	Glycosides	en
dc.subject.other	Humans	en
dc.subject.other	Lipase	en
dc.subject.other	Serum	en
dc.subject.other	Candida antarctica	en
dc.subject.other	Posibacteria	en
dc.title	Biocatalytic preparation of acylated derivatives of flavonoid glycosides enhances their antioxidant and antimicrobial activity	en
heal.type	journalArticle	en
heal.identifier.primary	10.1016/j.jbiotec.2004.12.002	en
heal.identifier.secondary	http://dx.doi.org/10.1016/j.jbiotec.2004.12.002	en
heal.language	English	en
heal.publicationDate	2005	en
heal.abstract	Enzymatic synthesis of acylated derivatives of a monosaccharidic flavonoid chrysoeriol-7-O-beta-D-(3"-E-p-coumaroyl)glucopyranoside as well as of a disaccharidic flavonoid chrysoeriol-7-[6'"-O-acetyl-beta-D-allosyl-(1 --> 2)-beta-D-glucopyranoside], isolated from Greek endemic plants, was performed using an immobilized Candida antarctica lipase in non-toxic organic solvents. The influence of the reaction parameters such as the molar ratio of acyl donor to flavonoid, as well as the nature of the acyl donor, on the performance of the biocatalytic process was pointed out using the acylation of naringin as a model reaction. With vinyl laurate as acyl donor, the highest conversion was observed at relatively high molar ratio (greater than or equal to 10), using acetone as solvent. Lipase exhibits specificity towards primary alcohol of the glucose moiety of both flavonoid glycosides. The introduction of an acyl group into glucosylated flavonoids significantly improved their antioxidant activity towards both LDL and serum model in vitro. Furthermore, the acylated derivative of disaccharidic flavonoid increased its antimicrobial activity against two Gram-positive bacteria. (C) 2004 Elsevier B.V. All rights reserved.	en
heal.publisher	ELSEVIER SCIENCE BV	en
heal.journalName	Journal of Biotechnology	en
dc.identifier.doi	10.1016/j.jbiotec.2004.12.002	en
dc.identifier.isi	ISI:000227313600010	en
dc.identifier.volume	116	en
dc.identifier.issue	3	en
dc.identifier.spage	295	en
dc.identifier.epage	304	en