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Enzymatic synthesis of substituted epicatechins for bioactivity studies in neurological disorders.

Abstract：

:Glucuronidated and/or methylated metabolites of the proanthocyanidin (PA) monomer (-)-epicatechin are detected in both blood and brain following feeding of rodents with a monomeric grape seed PA extract shown to reduce symptoms in a mouse model of Alzheimer's disease. To generate metabolites for future mechanistic studies, we investigated the ability of recombinant human glucuronosyl transferases of the UGT1A and UGT2B families to glucuronidate epicatechin or 3'-O-methyl epicatechin in vitro. Of twelve enzymes tested, UGT1A9 was the most efficient, producing epicatechin 3'-O-glucuronide as the major product. Incubation of UGT1A9 with 3'-O-methyl-epicatechin resulted in two major products, one of which was identified as 3'-O-methyl-epicatechin 5-O-glucuronide, a major metabolite found in blood plasma and brain tissue of the rodents following feeding with a grape seed extract. We also investigated in vitro methylation of epicatechin and epicatechin glucuronides by human catechol O-methyltransferase. Enzymatic production of 3'-O-methyl-epicatechin 5-O-glucuronide was optimized to 50% overall yield. These studies form a basis for generation of mg quantities of pure epicatechin (methyl) glucuronides of biological significance, and provide clarification of structure of previously identified epicatechin metabolites.

journal_name

Biochem Biophys Res Commun

journal_title

Biochemical and biophysical research communications

authors

Blount JW,Ferruzzi M,Raftery D,Pasinetti GM,Dixon RA

doi

10.1016/j.bbrc.2011.11.139

subject

Has Abstract

pub_date

2012-01-06 00:00:00

pages

457-61

issue

1

eissn

0006-291X

issn

1090-2104

pii

S0006-291X(11)02167-X

journal_volume

417

pub_type

杂志文章

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