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Structure Elucidation of Procyanidins Isolated from Rhododendron formosanum and Their Anti-Oxidative and Anti-Bacterial Activities

Rhododendron formosanum is an endemic species distributed in the central mountains of Taiwan. In this study, the biological activities of major procyanidins isolated from the leaf extract of R. formosanum were investigated. Four compounds, including two procyanidin dimers, procyanidin A1 (1) and B3...

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Autores principales: Wang, Chao-Min, Hsu, Yuan-Man, Jhan, Yun-Lian, Tsai, Shang-Jie, Lin, Shi-Xun, Su, Chiu-Hsian, Chou, Chang-Hung
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332352/
https://www.ncbi.nlm.nih.gov/pubmed/26184152
http://dx.doi.org/10.3390/molecules200712787
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author Wang, Chao-Min
Hsu, Yuan-Man
Jhan, Yun-Lian
Tsai, Shang-Jie
Lin, Shi-Xun
Su, Chiu-Hsian
Chou, Chang-Hung
author_facet Wang, Chao-Min
Hsu, Yuan-Man
Jhan, Yun-Lian
Tsai, Shang-Jie
Lin, Shi-Xun
Su, Chiu-Hsian
Chou, Chang-Hung
author_sort Wang, Chao-Min
collection PubMed
description Rhododendron formosanum is an endemic species distributed in the central mountains of Taiwan. In this study, the biological activities of major procyanidins isolated from the leaf extract of R. formosanum were investigated. Four compounds, including two procyanidin dimers, procyanidin A1 (1) and B3 (2), and two procyanidin trimmers, procyanidin C4 (4) and cinnamtannin D1 (5), were isolated and identified on the basis of spectroscopic data. The structure of a new procyanidin dimer, rhodonidin A (3), was elucidated by 2D-NMR, CD spectrum and MS. The procyanidin trimmers and rhodonidin A are reported for the first time in Ericaceae. The biological activities of these procyanidins were evaluated using anti-bacterial and anti-oxidative assays. Only the new compound 3 demonstrated strong anti-bacterial activity against Staphylococcus aureus at an MIC value of 4 μg/mL. All compounds showed pronounced antioxidant activities and the activities are enhanced as the amount of OH groups in procyanidins increased. In conclusion, the pleiotropic effects of procyanidins isolated from the leaves of R. formosanum can be a source of promising compounds for the development of future pharmacological applications.
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spelling pubmed-63323522019-01-24 Structure Elucidation of Procyanidins Isolated from Rhododendron formosanum and Their Anti-Oxidative and Anti-Bacterial Activities Wang, Chao-Min Hsu, Yuan-Man Jhan, Yun-Lian Tsai, Shang-Jie Lin, Shi-Xun Su, Chiu-Hsian Chou, Chang-Hung Molecules Article Rhododendron formosanum is an endemic species distributed in the central mountains of Taiwan. In this study, the biological activities of major procyanidins isolated from the leaf extract of R. formosanum were investigated. Four compounds, including two procyanidin dimers, procyanidin A1 (1) and B3 (2), and two procyanidin trimmers, procyanidin C4 (4) and cinnamtannin D1 (5), were isolated and identified on the basis of spectroscopic data. The structure of a new procyanidin dimer, rhodonidin A (3), was elucidated by 2D-NMR, CD spectrum and MS. The procyanidin trimmers and rhodonidin A are reported for the first time in Ericaceae. The biological activities of these procyanidins were evaluated using anti-bacterial and anti-oxidative assays. Only the new compound 3 demonstrated strong anti-bacterial activity against Staphylococcus aureus at an MIC value of 4 μg/mL. All compounds showed pronounced antioxidant activities and the activities are enhanced as the amount of OH groups in procyanidins increased. In conclusion, the pleiotropic effects of procyanidins isolated from the leaves of R. formosanum can be a source of promising compounds for the development of future pharmacological applications. MDPI 2015-07-15 /pmc/articles/PMC6332352/ /pubmed/26184152 http://dx.doi.org/10.3390/molecules200712787 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
Wang, Chao-Min
Hsu, Yuan-Man
Jhan, Yun-Lian
Tsai, Shang-Jie
Lin, Shi-Xun
Su, Chiu-Hsian
Chou, Chang-Hung
Structure Elucidation of Procyanidins Isolated from Rhododendron formosanum and Their Anti-Oxidative and Anti-Bacterial Activities
title Structure Elucidation of Procyanidins Isolated from Rhododendron formosanum and Their Anti-Oxidative and Anti-Bacterial Activities
title_full Structure Elucidation of Procyanidins Isolated from Rhododendron formosanum and Their Anti-Oxidative and Anti-Bacterial Activities
title_fullStr Structure Elucidation of Procyanidins Isolated from Rhododendron formosanum and Their Anti-Oxidative and Anti-Bacterial Activities
title_full_unstemmed Structure Elucidation of Procyanidins Isolated from Rhododendron formosanum and Their Anti-Oxidative and Anti-Bacterial Activities
title_short Structure Elucidation of Procyanidins Isolated from Rhododendron formosanum and Their Anti-Oxidative and Anti-Bacterial Activities
title_sort structure elucidation of procyanidins isolated from rhododendron formosanum and their anti-oxidative and anti-bacterial activities
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332352/
https://www.ncbi.nlm.nih.gov/pubmed/26184152
http://dx.doi.org/10.3390/molecules200712787
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