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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...
Autores principales: | , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2015
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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. |
format | Online Article Text |
id | pubmed-6332077 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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