191666-22-5Relevant articles and documents
Efficient and divergent enantioselective syntheses of DHPVs and anti-inflammatory effect on IEC-6 cells
Chung, Sungkyun,Hur, Joonseong,Kim, Eun-Hee,Kim, Hyun Su,Kim, Seok-Ho,Kwon, Hyuk,Lim, Changjin,Shin, Dongyun,Shin, Hyeyoung,Song, Moon-Young,Suh, Young-Ger
, (2020/05/18)
Despite numerous reports on the beneficial effects of catechin or epicatechin contained in tea and cacao extract on human health, a conclusive and precise molecular mechanism has not been elucidated. Metabolism of chemical compounds in gut microbiota recently gained significant attention, and extensive studies have been devoted in this field. In conjunction with these results, our group focused on the anti-inflammatory effects of both enantiomers of DHPV (5-(3',4'-dihydroxyphenyl)-γ-valerolactone), produced in the intestine by microbiota metabolism, on IEC-6 cells. Divergent and efficient enantioselective synthesis of (S)- and (R)-DHPV was efficiently achieved by cross-metathesis and Sharpless asymmetric dihydroxylation as a key reaction for four steps in 16% and 14% overall yields, respectively. The anti-inflammatory effects of two enantiomers were tested on IEC-6 cells, and we found that (S)-DHPV was more active than (R)-DHPV. This result implicates that the metabolite produced in the gut has beneficial effects on IEC-6 cells of rat intestines, and the chirality of the metabolite is important for its anti-inflammatory activity. This also provided information for the future discovery of novel small molecular therapeutics for the treatment of inflammatory bowel disease.
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.
