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...
Main Authors: | , , , , , , , , , |
---|---|
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/ |
_version_ | 1811183947598528512 |
---|---|
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. |
first_indexed | 2024-04-11T13:06:14Z |
format | Article |
id | doaj.art-8d2ea0b63d70455f81d10e59961b95c9 |
institution | Directory Open Access Journal |
issn | 1660-3397 |
language | English |
last_indexed | 2024-04-11T13:06:14Z |
publishDate | 2011-08-01 |
publisher | MDPI AG |
record_format | Article |
series | Marine Drugs |
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/ |
work_keys_str_mv | AT wenzhang bioactive3z5e1120epoxybriara35dien718olidediterpenoidsfromthesouthchinaseagorgoniandichotellagemmacea AT lingli bioactive3z5e1120epoxybriara35dien718olidediterpenoidsfromthesouthchinaseagorgoniandichotellagemmacea AT yanghuayi bioactive3z5e1120epoxybriara35dien718olidediterpenoidsfromthesouthchinaseagorgoniandichotellagemmacea AT attilamandi bioactive3z5e1120epoxybriara35dien718olidediterpenoidsfromthesouthchinaseagorgoniandichotellagemmacea AT tiborkurtan bioactive3z5e1120epoxybriara35dien718olidediterpenoidsfromthesouthchinaseagorgoniandichotellagemmacea AT mingpingla bioactive3z5e1120epoxybriara35dien718olidediterpenoidsfromthesouthchinaseagorgoniandichotellagemmacea AT pengsun bioactive3z5e1120epoxybriara35dien718olidediterpenoidsfromthesouthchinaseagorgoniandichotellagemmacea AT baoshuliu bioactive3z5e1120epoxybriara35dien718olidediterpenoidsfromthesouthchinaseagorgoniandichotellagemmacea AT cuili bioactive3z5e1120epoxybriara35dien718olidediterpenoidsfromthesouthchinaseagorgoniandichotellagemmacea AT huatang bioactive3z5e1120epoxybriara35dien718olidediterpenoidsfromthesouthchinaseagorgoniandichotellagemmacea |