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Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758)

Two previously undescribed caryophyllane-related sesquiterpenoids, antipacids A (1) and B (2), with a novel bicyclo[5.2.0] core skeleton, and known compound clovane-2β,9α-diol (3), along with rumphellolide L (4), an esterified product of 1 and 3, were isolated from the organic extract of octocoral R...

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Autores principales: Chang, Yu-Chia, Chiang, Chih-Chao, Chang, Yuan-Shiun, Chen, Jih-Jung, Wang, Wei-Hsien, Fang, Lee-Shing, Chung, Hsu-Ming, Hwang, Tsong-Long, Sung, Ping-Jyun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
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Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7694975/
https://www.ncbi.nlm.nih.gov/pubmed/33172193
http://dx.doi.org/10.3390/md18110554
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author Chang, Yu-Chia
Chiang, Chih-Chao
Chang, Yuan-Shiun
Chen, Jih-Jung
Wang, Wei-Hsien
Fang, Lee-Shing
Chung, Hsu-Ming
Hwang, Tsong-Long
Sung, Ping-Jyun
author_facet Chang, Yu-Chia
Chiang, Chih-Chao
Chang, Yuan-Shiun
Chen, Jih-Jung
Wang, Wei-Hsien
Fang, Lee-Shing
Chung, Hsu-Ming
Hwang, Tsong-Long
Sung, Ping-Jyun
author_sort Chang, Yu-Chia
collection PubMed
description Two previously undescribed caryophyllane-related sesquiterpenoids, antipacids A (1) and B (2), with a novel bicyclo[5.2.0] core skeleton, and known compound clovane-2β,9α-diol (3), along with rumphellolide L (4), an esterified product of 1 and 3, were isolated from the organic extract of octocoral Rumphella antipathes. Their structures, including the absolute configurations were elucidated by spectroscopic and chemical experiments. In vivo anti-inflammatory activity analysis indicated that antipacid B (2) inhibited the generation of superoxide anions and the release of elastase by human neutrophils, with IC(50) values of 11.22 and 23.53 μM, respectively, while rumphellolide L (4) suppressed the release of elastase with an IC(50) value of 7.63 μM.
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spelling pubmed-76949752020-11-28 Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758) Chang, Yu-Chia Chiang, Chih-Chao Chang, Yuan-Shiun Chen, Jih-Jung Wang, Wei-Hsien Fang, Lee-Shing Chung, Hsu-Ming Hwang, Tsong-Long Sung, Ping-Jyun Mar Drugs Article Two previously undescribed caryophyllane-related sesquiterpenoids, antipacids A (1) and B (2), with a novel bicyclo[5.2.0] core skeleton, and known compound clovane-2β,9α-diol (3), along with rumphellolide L (4), an esterified product of 1 and 3, were isolated from the organic extract of octocoral Rumphella antipathes. Their structures, including the absolute configurations were elucidated by spectroscopic and chemical experiments. In vivo anti-inflammatory activity analysis indicated that antipacid B (2) inhibited the generation of superoxide anions and the release of elastase by human neutrophils, with IC(50) values of 11.22 and 23.53 μM, respectively, while rumphellolide L (4) suppressed the release of elastase with an IC(50) value of 7.63 μM. MDPI 2020-11-06 /pmc/articles/PMC7694975/ /pubmed/33172193 http://dx.doi.org/10.3390/md18110554 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
Chang, Yu-Chia
Chiang, Chih-Chao
Chang, Yuan-Shiun
Chen, Jih-Jung
Wang, Wei-Hsien
Fang, Lee-Shing
Chung, Hsu-Ming
Hwang, Tsong-Long
Sung, Ping-Jyun
Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758)
title Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758)
title_full Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758)
title_fullStr Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758)
title_full_unstemmed Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758)
title_short Novel Caryophyllane-Related Sesquiterpenoids with Anti-Inflammatory Activity from Rumphella antipathes (Linnaeus, 1758)
title_sort novel caryophyllane-related sesquiterpenoids with anti-inflammatory activity from rumphella antipathes (linnaeus, 1758)
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7694975/
https://www.ncbi.nlm.nih.gov/pubmed/33172193
http://dx.doi.org/10.3390/md18110554
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