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Strophiofimbrins A 和 B:来自. 的两种具有新型三环碳骨架的重排诺特替品

Strophiofimbrins A and B: Two Rearranged Norditerpenoids with Novel Tricyclic Carbon Skeletons from .

机构信息

Institute of Translational Medicine, Medical College, Yangzhou University, Yangzhou, Jiangsu 225009, China.

Jiangsu Key Laboratory of Integrated Traditional Chinese and Western Medicine for Prevention and Treatment of Senile Diseases, Yangzhou University, Yangzhou, Jiangsu 225009, China.

出版信息

J Org Chem. 2023 May 5;88(9):5936-5943. doi: 10.1021/acs.joc.3c00301. Epub 2023 Apr 12.

Abstract

Two rearranged norditerpenoids with novel tricyclic carbon skeletons, strophiofimbrin A () and strophiofimbrin B (), were isolated from . Their structures were established by 1D/2D NMR spectroscopy, HRESIMS, quantum chemistry calculations, and X-ray diffraction analyses. and represented the first examples of diterpenoids with unprecedented 5/6/7-fused ring systems. In the proposed biosynthetic pathway, they were suspected to derive from cleistanthane norditerpenoids via ring opening, expansion, cyclization, and rearrangement based on the existence of phenanthrenone and cleistanthane diterpenoids from and , two closely related genera of the Euphorbiaceae family. Furthermore, compounds and exhibited significant proliferation inhibition and obvious neuroprotective effects.

摘要

从大戟科植物中分离得到两个具有新颖三环碳骨架的 rearranged norditerpenoids,分别命名为 strophiofimbrin A () 和 strophiofimbrin B ()。通过 1D/2D NMR 光谱、HRESIMS、量子化学计算和 X 射线衍射分析确定了它们的结构。和代表了具有前所未有的 5/6/7 稠合环系统的二萜类化合物的第一个例子。在提出的生物合成途径中,基于 phenanthrenone 和 cleistanthane 二萜类化合物的存在,它们被怀疑是通过环开裂、扩展、环化和重排从 cleistanthane norditerpenoids 衍生而来,phenanthrenone 和 cleistanthane 二萜类化合物分别来自大戟科的两个密切相关的属。此外,化合物和表现出显著的增殖抑制和明显的神经保护作用。

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