Enzymatic synthesis of butyl hydroxycinnamates and their inhibitory effects on LDL-oxidation

Vafiadi, C; Topakas, E; Alissandratos, A; Faulds, CB; Christakopoulos, P

dc.contributor.author	Vafiadi, C	en
dc.contributor.author	Topakas, E	en
dc.contributor.author	Alissandratos, A	en
dc.contributor.author	Faulds, CB	en
dc.contributor.author	Christakopoulos, P	en
dc.date.accessioned	2014-03-01T01:28:16Z
dc.date.available	2014-03-01T01:28:16Z
dc.date.issued	2008	en
dc.identifier.issn	0168-1656	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/18795
dc.subject	Cross-linked enzyme aggregates	en
dc.subject	Feruloyl esterase	en
dc.subject	LDL oxidative modification	en
dc.subject	Sinapate transesterification	en
dc.subject.classification	Biotechnology & Applied Microbiology	en
dc.subject.other	Butyl hydroxycinnamates	en
dc.subject.other	Feruloyl esterase	en
dc.subject.other	Sinapic acids	en
dc.subject.other	Biosynthesis	en
dc.subject.other	Enzyme inhibition	en
dc.subject.other	Esters	en
dc.subject.other	Oxidation	en
dc.subject.other	Parameter estimation	en
dc.subject.other	Enzyme activity	en
dc.subject.other	1 butylsinapate	en
dc.subject.other	2 butanol	en
dc.subject.other	2 butylsinapate	en
dc.subject.other	butanol	en
dc.subject.other	butyl hydroxycinnamate	en
dc.subject.other	carboxylesterase	en
dc.subject.other	copper	en
dc.subject.other	coumaric acid	en
dc.subject.other	feruloyl esterase	en
dc.subject.other	hexane	en
dc.subject.other	hydrocinnamic acid derivative	en
dc.subject.other	low density lipoprotein	en
dc.subject.other	methyl hydroxycinnamate	en
dc.subject.other	sinapic acid derivative	en
dc.subject.other	unclassified drug	en
dc.subject.other	antioxidant activity	en
dc.subject.other	article	en
dc.subject.other	Aspergillus niger	en
dc.subject.other	biocatalyst	en
dc.subject.other	chemical reaction	en
dc.subject.other	controlled study	en
dc.subject.other	enzyme synthesis	en
dc.subject.other	esterification	en
dc.subject.other	in vitro study	en
dc.subject.other	kinetics	en
dc.subject.other	oxidation	en
dc.subject.other	priority journal	en
dc.subject.other	protein cross linking	en
dc.subject.other	protein immobilization	en
dc.subject.other	Aspergillus niger	en
dc.subject.other	Carboxylic Ester Hydrolases	en
dc.subject.other	Chromatography, High Pressure Liquid	en
dc.subject.other	Coumaric Acids	en
dc.subject.other	Lipoproteins, LDL	en
dc.subject.other	Microscopy, Electron, Transmission	en
dc.subject.other	Molecular Structure	en
dc.subject.other	Oxidation-Reduction	en
dc.subject.other	Temperature	en
dc.subject.other	Aspergillus niger	en
dc.title	Enzymatic synthesis of butyl hydroxycinnamates and their inhibitory effects on LDL-oxidation	en
heal.type	journalArticle	en
heal.identifier.primary	10.1016/j.jbiotec.2007.11.004	en
heal.identifier.secondary	http://dx.doi.org/10.1016/j.jbiotec.2007.11.004	en
heal.language	English	en
heal.publicationDate	2008	en
heal.abstract	The potential of the Aspergillus niger type A feruloyl esterase (AnFaeA) for the synthesis of various phenolic acid esters was examined using a ternary-organic reaction system consisting of a mixture of n-hexane, 1- or 2-butanol and water. Reaction parameters including the type of methyl hydroxycinnamate, the composition of the reaction media, the temperature, and the substrate concentration were investigated to evaluate their effect on initial rate and conversion to butyl esters of sinapic acids. Optimisation of the reaction parameters lead to 78% and 9% yield for the synthesis of 1-butyl and 2-butyl sinapate, respectively. For the first time, a feruloyl esterase was introduced in the reaction system as cross-linked enzyme aggregates (CLEAs), after optimisation of the immobilisation procedure, allowing the recycling and reuse of the biocatalyst. The inhibition of copper-induced LDL oxidation by hydroxycinnamic acids and their corresponding butyl esters was investigated in vitro. Kinetic analysis of the antioxidation process demonstrates that sinapate derivatives are effective antioxidants indicating that esterification increases the free acid's antioxidant activity especially on dimethoxylated compounds such as sinapic acid compared to methoxy-hydroxy-compounds such as ferulic acid. (C) 2007 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.2007.11.004	en
dc.identifier.isi	ISI:000253875500012	en
dc.identifier.volume	133	en
dc.identifier.issue	4	en
dc.identifier.spage	497	en
dc.identifier.epage	504	en