A Polyol-Polyol Super-Carbon-Chain Compound Containing Thirty-Six Carbon Stereocenters from the Dinoflagellate <i>Amphidinium gibbosum</i>: Absolute Configuration and Multi-Segment Modification

A Polyol-Polyol Super-Carbon-Chain Compound Containing Thirty-Six Carbon Stereocenters from the Dinoflagellate <i>Amphidinium gibbosum</i>: Absolute Configuration and Multi-Segment Modification

A super-carbon-chain compound, named gibbosol C, featuring a polyoxygenated C<sub>70</sub>-linear-carbon-chain backbone encompassing two acyclic polyol chains, was obtained from the South China Sea dinoflagellate <i>Amphidinium gibbosum</i>. Its planar structure was elucidate...

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Main Authors: Wan-Shan Li, Zeng Luo, Yan-Lan Zhu, Yi Yu, Jun Wu, Li Shen
Format: Article
Language:English
Published: MDPI AG 2020-11-01
Series:Marine Drugs
Subjects:
marine dinoflagellate
<i>Amphidinium gibbosum</i>
super-carbon-chain compound
absolute configuration
multi-segment modification
Online Access:https://www.mdpi.com/1660-3397/18/12/590
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spelling doaj-8a9b944934254795a5b6570f7e9504572020-11-27T08:07:50ZengMDPI AGMarine Drugs1660-33972020-11-011859059010.3390/md18120590A Polyol-Polyol Super-Carbon-Chain Compound Containing Thirty-Six Carbon Stereocenters from the Dinoflagellate <i>Amphidinium gibbosum</i>: Absolute Configuration and Multi-Segment ModificationWan-Shan Li0Zeng Luo1Yan-Lan Zhu2Yi Yu3Jun Wu4Li Shen5School of Pharmaceutical Sciences, Southern Medical University, 1838 Guangzhou Avenue North, Guangzhou 510515, ChinaSchool of Pharmaceutical Sciences, Southern Medical University, 1838 Guangzhou Avenue North, Guangzhou 510515, ChinaSchool of Pharmaceutical Sciences, Southern Medical University, 1838 Guangzhou Avenue North, Guangzhou 510515, ChinaMarine Drugs Research Center, College of Pharmacy, Jinan University, 601 Huangpu Avenue West, Guangzhou 510632, ChinaSchool of Pharmaceutical Sciences, Southern Medical University, 1838 Guangzhou Avenue North, Guangzhou 510515, ChinaMarine Drugs Research Center, College of Pharmacy, Jinan University, 601 Huangpu Avenue West, Guangzhou 510632, ChinaA super-carbon-chain compound, named gibbosol C, featuring a polyoxygenated C<sub>70</sub>-linear-carbon-chain backbone encompassing two acyclic polyol chains, was obtained from the South China Sea dinoflagellate <i>Amphidinium gibbosum</i>. Its planar structure was elucidated by extensive NMR investigations, whereas its absolute configurations, featuring the presence of 36 carbon stereocenters and 30 hydroxy groups, were successfully established by comparison of NMR data of the ozonolyzed products with those of gibbosol A, combined with <i>J</i>-based configuration analysis, Kishi’s universal NMR database, and the modified Mosher’s MTPA ester method. Multi-segment modification was revealed as the smart biosynthetic strategy for the dinoflagellate to create remarkable super-carbon-chain compounds with structural diversity.https://www.mdpi.com/1660-3397/18/12/590marine dinoflagellate<i>Amphidinium gibbosum</i>super-carbon-chain compoundabsolute configurationmulti-segment modification
collection DOAJ
language English
format Article
sources DOAJ
author Wan-Shan Li
Zeng Luo
Yan-Lan Zhu
Yi Yu
Jun Wu
Li Shen
spellingShingle Wan-Shan Li
Zeng Luo
Yan-Lan Zhu
Yi Yu
Jun Wu
Li Shen
A Polyol-Polyol Super-Carbon-Chain Compound Containing Thirty-Six Carbon Stereocenters from the Dinoflagellate <i>Amphidinium gibbosum</i>: Absolute Configuration and Multi-Segment Modification
Marine Drugs
marine dinoflagellate
<i>Amphidinium gibbosum</i>
super-carbon-chain compound
absolute configuration
multi-segment modification
author_facet Wan-Shan Li
Zeng Luo
Yan-Lan Zhu
Yi Yu
Jun Wu
Li Shen
author_sort Wan-Shan Li
title A Polyol-Polyol Super-Carbon-Chain Compound Containing Thirty-Six Carbon Stereocenters from the Dinoflagellate <i>Amphidinium gibbosum</i>: Absolute Configuration and Multi-Segment Modification
title_short A Polyol-Polyol Super-Carbon-Chain Compound Containing Thirty-Six Carbon Stereocenters from the Dinoflagellate <i>Amphidinium gibbosum</i>: Absolute Configuration and Multi-Segment Modification
title_full A Polyol-Polyol Super-Carbon-Chain Compound Containing Thirty-Six Carbon Stereocenters from the Dinoflagellate <i>Amphidinium gibbosum</i>: Absolute Configuration and Multi-Segment Modification
title_fullStr A Polyol-Polyol Super-Carbon-Chain Compound Containing Thirty-Six Carbon Stereocenters from the Dinoflagellate <i>Amphidinium gibbosum</i>: Absolute Configuration and Multi-Segment Modification
title_full_unstemmed A Polyol-Polyol Super-Carbon-Chain Compound Containing Thirty-Six Carbon Stereocenters from the Dinoflagellate <i>Amphidinium gibbosum</i>: Absolute Configuration and Multi-Segment Modification
title_sort polyol-polyol super-carbon-chain compound containing thirty-six carbon stereocenters from the dinoflagellate <i>amphidinium gibbosum</i>: absolute configuration and multi-segment modification
publisher MDPI AG
series Marine Drugs
issn 1660-3397
publishDate 2020-11-01
description A super-carbon-chain compound, named gibbosol C, featuring a polyoxygenated C<sub>70</sub>-linear-carbon-chain backbone encompassing two acyclic polyol chains, was obtained from the South China Sea dinoflagellate <i>Amphidinium gibbosum</i>. Its planar structure was elucidated by extensive NMR investigations, whereas its absolute configurations, featuring the presence of 36 carbon stereocenters and 30 hydroxy groups, were successfully established by comparison of NMR data of the ozonolyzed products with those of gibbosol A, combined with <i>J</i>-based configuration analysis, Kishi’s universal NMR database, and the modified Mosher’s MTPA ester method. Multi-segment modification was revealed as the smart biosynthetic strategy for the dinoflagellate to create remarkable super-carbon-chain compounds with structural diversity.
topic marine dinoflagellate
<i>Amphidinium gibbosum</i>
super-carbon-chain compound
absolute configuration
multi-segment modification
url https://www.mdpi.com/1660-3397/18/12/590
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