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Structure–Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities

Proanthocyanidins, which are composed of oligomeric flavan-3-ol units, are contained in various foodstuffs (e.g., fruits, vegetables, and drinks) and are strongly biologically active compounds. We investigated which element of the proanthocyanidin structure is primarily responsible for this function...

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Autores principales: Hamada, Yoshitomo, Takano, Syota, Ayano, Yoshihiro, Tokunaga, Masahiro, Koashi, Takahiro, Okamoto, Syuhei, Doi, Syoma, Ishida, Masahiko, Kawasaki, Takashi, Hamada, Masahiro, Nakajima, Noriyuki, Saito, Akiko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332077/
https://www.ncbi.nlm.nih.gov/pubmed/26501251
http://dx.doi.org/10.3390/molecules201018870
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author Hamada, Yoshitomo
Takano, Syota
Ayano, Yoshihiro
Tokunaga, Masahiro
Koashi, Takahiro
Okamoto, Syuhei
Doi, Syoma
Ishida, Masahiko
Kawasaki, Takashi
Hamada, Masahiro
Nakajima, Noriyuki
Saito, Akiko
author_facet Hamada, Yoshitomo
Takano, Syota
Ayano, Yoshihiro
Tokunaga, Masahiro
Koashi, Takahiro
Okamoto, Syuhei
Doi, Syoma
Ishida, Masahiko
Kawasaki, Takashi
Hamada, Masahiro
Nakajima, Noriyuki
Saito, Akiko
author_sort Hamada, Yoshitomo
collection PubMed
description Proanthocyanidins, which are composed of oligomeric flavan-3-ol units, are contained in various foodstuffs (e.g., fruits, vegetables, and drinks) and are strongly biologically active compounds. We investigated which element of the proanthocyanidin structure is primarily responsible for this functionality. In this study, we elucidate the importance of the upper-unit of 4–8 condensed dimeric flavan-3-ols for antimicrobial activity against Saccharomyces cerevisiae (S. cerevisiae) and cervical epithelioid carcinoma cell line HeLa S3 proliferation inhibitory activity. To clarify the important constituent unit of proanthocyanidin, we synthesized four dimeric compounds, (−)-epigallocatechin-[4,8]-(+)-catechin, (−)-epigallocatechin-[4,8]-(−)-epigallocatechin, (−)-epigallocatechin-[4,8]-(−)-epigallocatechin-3-O-gallate, and (+)-catechin-[4,8]-(−)-epigallocatechin and performed structure–activity relationship (SAR) studies. In addition to antimicrobial activity against S. cerevisiae and proliferation inhibitory activity on HeLa S3 cells, the correlation of 2,2-diphenyl-l-picrylhydrazyl radical scavenging activity with the number of phenolic hydroxyl groups was low. On the basis of the results of our SAR studies, we concluded that B-ring hydroxyl groups of the upper-unit of the dimer are crucially important for strong and effective activity.
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spelling pubmed-63320772019-01-24 Structure–Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities Hamada, Yoshitomo Takano, Syota Ayano, Yoshihiro Tokunaga, Masahiro Koashi, Takahiro Okamoto, Syuhei Doi, Syoma Ishida, Masahiko Kawasaki, Takashi Hamada, Masahiro Nakajima, Noriyuki Saito, Akiko Molecules Article Proanthocyanidins, which are composed of oligomeric flavan-3-ol units, are contained in various foodstuffs (e.g., fruits, vegetables, and drinks) and are strongly biologically active compounds. We investigated which element of the proanthocyanidin structure is primarily responsible for this functionality. In this study, we elucidate the importance of the upper-unit of 4–8 condensed dimeric flavan-3-ols for antimicrobial activity against Saccharomyces cerevisiae (S. cerevisiae) and cervical epithelioid carcinoma cell line HeLa S3 proliferation inhibitory activity. To clarify the important constituent unit of proanthocyanidin, we synthesized four dimeric compounds, (−)-epigallocatechin-[4,8]-(+)-catechin, (−)-epigallocatechin-[4,8]-(−)-epigallocatechin, (−)-epigallocatechin-[4,8]-(−)-epigallocatechin-3-O-gallate, and (+)-catechin-[4,8]-(−)-epigallocatechin and performed structure–activity relationship (SAR) studies. In addition to antimicrobial activity against S. cerevisiae and proliferation inhibitory activity on HeLa S3 cells, the correlation of 2,2-diphenyl-l-picrylhydrazyl radical scavenging activity with the number of phenolic hydroxyl groups was low. On the basis of the results of our SAR studies, we concluded that B-ring hydroxyl groups of the upper-unit of the dimer are crucially important for strong and effective activity. MDPI 2015-10-16 /pmc/articles/PMC6332077/ /pubmed/26501251 http://dx.doi.org/10.3390/molecules201018870 Text en © 2015 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 license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Hamada, Yoshitomo
Takano, Syota
Ayano, Yoshihiro
Tokunaga, Masahiro
Koashi, Takahiro
Okamoto, Syuhei
Doi, Syoma
Ishida, Masahiko
Kawasaki, Takashi
Hamada, Masahiro
Nakajima, Noriyuki
Saito, Akiko
Structure–Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities
title Structure–Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities
title_full Structure–Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities
title_fullStr Structure–Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities
title_full_unstemmed Structure–Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities
title_short Structure–Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities
title_sort structure–activity relationship of oligomeric flavan-3-ols: importance of the upper-unit b-ring hydroxyl groups in the dimeric structure for strong activities
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332077/
https://www.ncbi.nlm.nih.gov/pubmed/26501251
http://dx.doi.org/10.3390/molecules201018870
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