191666-22-5Relevant articles and documents
Concise synthesis of catechin metabolites 5-(30,40-dihydroxyphenyl)-γ-valerolactones (dhpv) in optically pure form and their stereochemical effects on skin wrinkle-reducing activities
Hur, Joonseong,Kim, A-Ram,Kim, Hyun Su,Kim, Tae-Aug,Kim, Taewoo,Lim, Changjin,Sim, Jaehoon,Suh, Young-Ger
, (2020/04/29)
A concise and scalable synthetic route for optically pure (4S) and (4R)-5-(30,40-dihydroxyphenyl)-γ-valerolactones (DHPVs), catechin metabolites, has been developed via the efficient construction of a γ-valerolactone moiety from hexe
Catalytic, Enantioselective Vinylogous Mukaiyama Aldol Reaction of Furan-Based Dienoxy Silanes: A Chemodivergent Approach to γ-Valerolactone Flavan-3-ol Metabolites and δ-Lactone Analogues
Curti, Claudio,Brindani, Nicoletta,Battistini, Lucia,Sartori, Andrea,Pelosi, Giorgio,Mena, Pedro,Brighenti, Furio,Zanardi, Franca,Delrio, Daniele
, p. 4082 - 4092 (2016/01/25)
The asymmetric synthesis of a set of hydroxyphenyl γ-valerolactones was achieved starting from 2-silyloxyfuran and alkoxy-substituted benzaldehydes as common precursors. Key synthesis steps included an enantioselective vinylogous Mukaiyama aldol reaction and a Barton-McCombie deoxygenation. Five enantioenriched γ-valerolactone targets were obtained in 5-6 steps, 18-63% overall yields and 82-98 % ee, paving the way for the straightforward entry to this class of biologically effective and poorly available flavan-3-ol metabolites. In parallel, an unprecedented one-pot reductive ring expansion process was fortuitously discovered, yielding racemic δ-lactone analogues from phenolic butanolide precursors.
Biotransformation of (-)-epicatechin 3-O-gallate by human intestinal bacteria
Meselhy, Meselhy R.,Nakamura, Norio,Hattori, Masao
, p. 888 - 893 (2007/10/03)
The biotransformation of (-)-epicatechin 3-O-gallate (1) and related compounds was undertaken using a human fecal suspension. Of fifteen metabolites isolated, four compounds were new, namely, two epimers of 1-(3'- hydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ols (6, 19); 2'',3''- dihydroxyphenoxyl 3-(3',4'-dihydroxyphenyl)propionate (14) and 1-(3',4'- dihydroxyphenyl)-3-(2'',4'',6''-trihydroxyphenyl)propan-2-ol (18). (-)- Epicatechin (2), (-)-epigallocatechin (16) and their 3-O-gallates (1, 17) were extensively metabolized by a human fecal suspension after incubation for 24 h, whereas the gallates (1, 17) resisted any degradation by a rat fecal suspension, even after a prolonged incubation time (48 h), suggesting a difference in metabolic ability between two intestinal bacterial mixtures from different species.