State Key Laboratory of Generic Manufacture Technology of Chinese Traditional Medicine, Lunan Pharmaceutical Group Co. Ltd., Linyi 273400, China.
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Yushan Road 5, Qingdao 266003, China.
Molecules. 2019 Oct 30;24(21):3912. doi: 10.3390/molecules24213912.
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.
倍半萜类化合物是一组结构多样的天然产物，具有广泛的分子结构。其中，不寻常的双环[6.3.0]十一碳倍半萜是最具代表性的一种。迄今为止，仅报道了约 42 种具有这种独特骨架的天然化合物，它们可以分为七个不同的组。作为每种类型的第一个发现成员，达托醇、asteriscanolide、dumortenol、toxicodenane C 和 capillosanane S 是五元-八元环系统上四个甲基的特征。只有 11-羟基贾宗酮和 sinuketal 用异丙基修饰核心。这些天然产物表现出广泛的生物活性，包括抗污、抗炎、免疫抑制、细胞毒性、抗突变、抗疟原虫和抗病毒活性。值得注意的是，一些 precapnellane-倍半萜（达托醇、poitediol、precapnelladiene）、asteriscanolide 和 11-羟基贾宗酮的全合成已经实现，因为它们的环辛烷核心代表了开发合成策略制备八元环化合物的重要目标。本文综述了这些天然倍半萜及其生物活性和合成，旨在为进一步研究这些有趣的化合物提供基础。
