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可可西康定 A-F,新型生物相关的具有不同骨架的角鲨烷型三萜类化合物,来自于中国特有的植物美丽崖椒。

Kadcoccinones A-F, New Biogenetically Related Lanostane-Type Triterpenoids with Diverse Skeletons from Kadsura coccinea.

机构信息

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, China.

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology , Wuhan 430030, China.

出版信息

Org Lett. 2015 Sep 18;17(18):4616-9. doi: 10.1021/acs.orglett.5b02360. Epub 2015 Sep 8.

Abstract

Six new lanostane-related triterpenoids, kadcoccinones A-F (1-6), were isolated from Kadsura coccinea. Compound 3 possesses a novel 6/6/9-fused carbocyclic core containing a rare oxabicyclo[4.3.1]decane system. Compounds 4 and 5 are isomers representing the first example of the 18(13 → 12)-abeo-26-norlanostane triterpenoid. The absolute configurations of 1 and 4-6 were defined by X-ray diffraction and experimental ECD spectra, and that of 3 was elucidated by quantum chemical calculations. The plausible biogenetic pathway of 1-6 is postulated.

摘要

从红毛藤中分离得到了六个新的角鲨烷相关三萜类化合物,即卡杜辛酮 A-F(1-6)。化合物 3 具有一个新颖的 6/6/9 稠合碳环核心,含有一个罕见的氧杂双环[4.3.1]癸烷系统。化合物 4 和 5 是异构体,代表了第一个 18(13 → 12)-abeo-26-降角鲨烷三萜类化合物的实例。通过 X 射线衍射和实验 ECD 光谱确定了 1 和 4-6 的绝对构型,通过量子化学计算确定了 3 的绝对构型。提出了 1-6 的可能生物合成途径。

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