ArticleBiochemical and biophysical research communications2012
Enzymatic synthesis of substituted epicatechins for bioactivity studies in neurological disorders.
Article in Biochemical and biophysical research communications, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 27 citations in OpenAlex.
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- UGT84F9 is the major flavonoid UDP-glucuronosyltransferase in Medicago truncatula.Plant physiology · 2021Article
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- The gut microbiota composition affects dietary polyphenols-mediated cognitive resilience in mice by modulating the bioavailability of phenolic acids.Scientific reports · 2019Article
- Epicatechin Prevents Methamphetamine-Induced Neuronal Cell Death via Inhibition of ER Stress.Biomolecules & therapeutics · 2019Article
- Dietary polyphenols promote resilience against sleep deprivation-induced cognitive impairment by activating protein translation.FASEB journal : official publication of the Federation of American Societies for Experimental Biology · 2018Article
- Epigenetic modulation of inflammation and synaptic plasticity promotes resilience against stress in mice.Nature communications · 2018Article
- Influence of diabetes on plasma pharmacokinetics and brain bioavailability of grape polyphenols and their phase II metabolites in the Zucker diabetic fatty rat.Molecular nutrition & food research · 2017Article
- Glucuronidated Flavonoids in Neurological Protection: Structural Analysis and Approaches for Chemical and Biological Synthesis.Journal of agricultural and food chemistry · 2017Review
- Novel application of brain-targeting polyphenol compounds in sleep deprivation-induced cognitive dysfunction.Neurochemistry international · 2015Article
Corrections and comments
- Erratum issued
Authors and funding
5 authors at 3 institutions in 1 country.
Funding
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.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.