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Bicyclo [6.3.0] Undecane Sesquiterpenoids: Structures, Biological Activities, and Syntheses

Sesquiterpenoids constitute a marvelously varied group of natural products that feature a vast array of molecular architectures. Among them, the unusual bicyclo [6.3.0] undecane sesquiterpenoids are one of the most representative. To date, only approximately 42 naturally occurring compounds with thi...

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Autores principales: Qin, Guo-Fei, Liang, Hong-Bao, Liu, Wen-Xiu, Zhu, Feng, Li, Ping-Lin, Li, Guo-Qiang, Yao, Jing-Chun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6864671/
https://www.ncbi.nlm.nih.gov/pubmed/31671644
http://dx.doi.org/10.3390/molecules24213912
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author Qin, Guo-Fei
Liang, Hong-Bao
Liu, Wen-Xiu
Zhu, Feng
Li, Ping-Lin
Li, Guo-Qiang
Yao, Jing-Chun
author_facet Qin, Guo-Fei
Liang, Hong-Bao
Liu, Wen-Xiu
Zhu, Feng
Li, Ping-Lin
Li, Guo-Qiang
Yao, Jing-Chun
author_sort Qin, Guo-Fei
collection PubMed
description Sesquiterpenoids constitute a marvelously varied group of natural products that feature a vast array of molecular architectures. Among them, the unusual bicyclo [6.3.0] undecane sesquiterpenoids are one of the most representative. To date, only approximately 42 naturally occurring compounds with this unique scaffold, which can be classified into seven different groups, have been reported. As the first-found member of each type, dactylol, asteriscanolide, dumortenol, toxicodenane C, and capillosanane S are characteristic of the four methyl groups on the five-eight-membered ring system. Only 11-hydroxyjasionone and sinuketal decorate the core with an isopropyl group. These natural products exhibit a wide range of bioactivities, including antifouling, anti-inflammatory, immune suppression, cytotoxic, antimutagenic, antiplasmodial, and antiviral activities. It was noted that some total syntheses of precapnellane-sesquiterpenoids (dactylol, poitediol, precapnelladiene), asteriscanolide, and 11-hydroxyjasionone have been achieved, because their cyclooctanoid core represents an important target for the development of synthetic strategies to prepare eight-membered ring-containing compounds. This review focuses on these natural sesquiterpenoids and their biological activities and synthesis, and aims to provide a foundation for further research of these interesting compounds.
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spelling pubmed-68646712019-12-23 Bicyclo [6.3.0] Undecane Sesquiterpenoids: Structures, Biological Activities, and Syntheses Qin, Guo-Fei Liang, Hong-Bao Liu, Wen-Xiu Zhu, Feng Li, Ping-Lin Li, Guo-Qiang Yao, Jing-Chun Molecules Review Sesquiterpenoids constitute a marvelously varied group of natural products that feature a vast array of molecular architectures. Among them, the unusual bicyclo [6.3.0] undecane sesquiterpenoids are one of the most representative. To date, only approximately 42 naturally occurring compounds with this unique scaffold, which can be classified into seven different groups, have been reported. As the first-found member of each type, dactylol, asteriscanolide, dumortenol, toxicodenane C, and capillosanane S are characteristic of the four methyl groups on the five-eight-membered ring system. Only 11-hydroxyjasionone and sinuketal decorate the core with an isopropyl group. These natural products exhibit a wide range of bioactivities, including antifouling, anti-inflammatory, immune suppression, cytotoxic, antimutagenic, antiplasmodial, and antiviral activities. It was noted that some total syntheses of precapnellane-sesquiterpenoids (dactylol, poitediol, precapnelladiene), asteriscanolide, and 11-hydroxyjasionone have been achieved, because their cyclooctanoid core represents an important target for the development of synthetic strategies to prepare eight-membered ring-containing compounds. This review focuses on these natural sesquiterpenoids and their biological activities and synthesis, and aims to provide a foundation for further research of these interesting compounds. MDPI 2019-10-30 /pmc/articles/PMC6864671/ /pubmed/31671644 http://dx.doi.org/10.3390/molecules24213912 Text en © 2019 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 Review
Qin, Guo-Fei
Liang, Hong-Bao
Liu, Wen-Xiu
Zhu, Feng
Li, Ping-Lin
Li, Guo-Qiang
Yao, Jing-Chun
Bicyclo [6.3.0] Undecane Sesquiterpenoids: Structures, Biological Activities, and Syntheses
title Bicyclo [6.3.0] Undecane Sesquiterpenoids: Structures, Biological Activities, and Syntheses
title_full Bicyclo [6.3.0] Undecane Sesquiterpenoids: Structures, Biological Activities, and Syntheses
title_fullStr Bicyclo [6.3.0] Undecane Sesquiterpenoids: Structures, Biological Activities, and Syntheses
title_full_unstemmed Bicyclo [6.3.0] Undecane Sesquiterpenoids: Structures, Biological Activities, and Syntheses
title_short Bicyclo [6.3.0] Undecane Sesquiterpenoids: Structures, Biological Activities, and Syntheses
title_sort bicyclo [6.3.0] undecane sesquiterpenoids: structures, biological activities, and syntheses
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6864671/
https://www.ncbi.nlm.nih.gov/pubmed/31671644
http://dx.doi.org/10.3390/molecules24213912
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