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Efficient and Divergent Enantioselective Syntheses of DHPVs and Anti-Inflammatory Effect on IEC-6 Cells
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 extens...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7248962/ https://www.ncbi.nlm.nih.gov/pubmed/32397326 http://dx.doi.org/10.3390/molecules25092215 |
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author | Kim, Hyun Su Chung, Sungkyun Song, Moon-Young Lim, Changjin Shin, Hyeyoung Hur, Joonseong Kwon, Hyuk Suh, Young-Ger Kim, Eun-Hee Shin, Dongyun Kim, Seok-Ho |
author_facet | Kim, Hyun Su Chung, Sungkyun Song, Moon-Young Lim, Changjin Shin, Hyeyoung Hur, Joonseong Kwon, Hyuk Suh, Young-Ger Kim, Eun-Hee Shin, Dongyun Kim, Seok-Ho |
author_sort | Kim, Hyun Su |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-7248962 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-72489622020-06-10 Efficient and Divergent Enantioselective Syntheses of DHPVs and Anti-Inflammatory Effect on IEC-6 Cells Kim, Hyun Su Chung, Sungkyun Song, Moon-Young Lim, Changjin Shin, Hyeyoung Hur, Joonseong Kwon, Hyuk Suh, Young-Ger Kim, Eun-Hee Shin, Dongyun Kim, Seok-Ho Molecules Article 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. MDPI 2020-05-08 /pmc/articles/PMC7248962/ /pubmed/32397326 http://dx.doi.org/10.3390/molecules25092215 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Kim, Hyun Su Chung, Sungkyun Song, Moon-Young Lim, Changjin Shin, Hyeyoung Hur, Joonseong Kwon, Hyuk Suh, Young-Ger Kim, Eun-Hee Shin, Dongyun Kim, Seok-Ho Efficient and Divergent Enantioselective Syntheses of DHPVs and Anti-Inflammatory Effect on IEC-6 Cells |
title | Efficient and Divergent Enantioselective Syntheses of DHPVs and Anti-Inflammatory Effect on IEC-6 Cells |
title_full | Efficient and Divergent Enantioselective Syntheses of DHPVs and Anti-Inflammatory Effect on IEC-6 Cells |
title_fullStr | Efficient and Divergent Enantioselective Syntheses of DHPVs and Anti-Inflammatory Effect on IEC-6 Cells |
title_full_unstemmed | Efficient and Divergent Enantioselective Syntheses of DHPVs and Anti-Inflammatory Effect on IEC-6 Cells |
title_short | Efficient and Divergent Enantioselective Syntheses of DHPVs and Anti-Inflammatory Effect on IEC-6 Cells |
title_sort | efficient and divergent enantioselective syntheses of dhpvs and anti-inflammatory effect on iec-6 cells |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7248962/ https://www.ncbi.nlm.nih.gov/pubmed/32397326 http://dx.doi.org/10.3390/molecules25092215 |
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