Bioactive (3Z,5E)-11,20-Epoxybriara-3,5-dien-7,18-olide Diterpenoids from the South China Sea Gorgonian Dichotella gemmacea

Six new (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids, gemmacolides N–S (1–6), were isolated together with four known analogues, juncenolide D, and juncins R, S and U (7–10), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by t...

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Main Authors: Wen Zhang, Ling Li, Yang-Hua Yi, Attila Mandi, Tibor Kurtan, Ming-Ping La, Peng Sun, Bao-Shu Liu, Cui Li, Hua Tang
Format: Article
Language:English
Published: MDPI AG 2011-08-01
Series:Marine Drugs
Subjects:
Online Access:http://www.mdpi.com/1660-3397/9/8/1403/
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author Wen Zhang
Ling Li
Yang-Hua Yi
Attila Mandi
Tibor Kurtan
Ming-Ping La
Peng Sun
Bao-Shu Liu
Cui Li
Hua Tang
author_facet Wen Zhang
Ling Li
Yang-Hua Yi
Attila Mandi
Tibor Kurtan
Ming-Ping La
Peng Sun
Bao-Shu Liu
Cui Li
Hua Tang
author_sort Wen Zhang
collection DOAJ
description Six new (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids, gemmacolides N–S (1–6), were isolated together with four known analogues, juncenolide D, and juncins R, S and U (7–10), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by the detailed analysis of spectroscopic data in combination with the comparison with reported data. The absolute configuration of 1 was determined by a TDDFT calculation of its solution ECD spectrum, affording the determination of absolute configuration of other analogues by simply comparing their ECD spectra with that of 1. The cytotoxic and antimicrobial activities of these compounds were evaluated. In preliminary in vitro bioassays, compounds 4, 5, 6, 8 and 9 showed cytotoxicity against A549 and MG63, while compounds 1, 2, 4, 7–10 showed antimicrobial activity against the fungus Septoria tritici and the bacterium Escherichia coli.
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spelling doaj.art-8d2ea0b63d70455f81d10e59961b95c92022-12-22T04:22:46ZengMDPI AGMarine Drugs1660-33972011-08-01981403141810.3390/md9081403Bioactive (3Z,5E)-11,20-Epoxybriara-3,5-dien-7,18-olide Diterpenoids from the South China Sea Gorgonian Dichotella gemmaceaWen ZhangLing LiYang-Hua YiAttila MandiTibor KurtanMing-Ping LaPeng SunBao-Shu LiuCui LiHua TangSix new (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids, gemmacolides N–S (1–6), were isolated together with four known analogues, juncenolide D, and juncins R, S and U (7–10), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by the detailed analysis of spectroscopic data in combination with the comparison with reported data. The absolute configuration of 1 was determined by a TDDFT calculation of its solution ECD spectrum, affording the determination of absolute configuration of other analogues by simply comparing their ECD spectra with that of 1. The cytotoxic and antimicrobial activities of these compounds were evaluated. In preliminary in vitro bioassays, compounds 4, 5, 6, 8 and 9 showed cytotoxicity against A549 and MG63, while compounds 1, 2, 4, 7–10 showed antimicrobial activity against the fungus Septoria tritici and the bacterium Escherichia coli.http://www.mdpi.com/1660-3397/9/8/1403/briarane diterpenoidsbiological activitystructure elucidationgorgonianDichotella gemmacea
spellingShingle Wen Zhang
Ling Li
Yang-Hua Yi
Attila Mandi
Tibor Kurtan
Ming-Ping La
Peng Sun
Bao-Shu Liu
Cui Li
Hua Tang
Bioactive (3Z,5E)-11,20-Epoxybriara-3,5-dien-7,18-olide Diterpenoids from the South China Sea Gorgonian Dichotella gemmacea
Marine Drugs
briarane diterpenoids
biological activity
structure elucidation
gorgonian
Dichotella gemmacea
title Bioactive (3Z,5E)-11,20-Epoxybriara-3,5-dien-7,18-olide Diterpenoids from the South China Sea Gorgonian Dichotella gemmacea
title_full Bioactive (3Z,5E)-11,20-Epoxybriara-3,5-dien-7,18-olide Diterpenoids from the South China Sea Gorgonian Dichotella gemmacea
title_fullStr Bioactive (3Z,5E)-11,20-Epoxybriara-3,5-dien-7,18-olide Diterpenoids from the South China Sea Gorgonian Dichotella gemmacea
title_full_unstemmed Bioactive (3Z,5E)-11,20-Epoxybriara-3,5-dien-7,18-olide Diterpenoids from the South China Sea Gorgonian Dichotella gemmacea
title_short Bioactive (3Z,5E)-11,20-Epoxybriara-3,5-dien-7,18-olide Diterpenoids from the South China Sea Gorgonian Dichotella gemmacea
title_sort bioactive 3z 5e 11 20 epoxybriara 3 5 dien 7 18 olide diterpenoids from the south china sea gorgonian dichotella gemmacea
topic briarane diterpenoids
biological activity
structure elucidation
gorgonian
Dichotella gemmacea
url http://www.mdpi.com/1660-3397/9/8/1403/
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