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翅荚决明 A 和 B,具有贝壳杉烷碳骨架的免疫刺激性二萜类化合物,特征为 3-氧杂四环[6.6.1.0.0]十五烷支架,来自翅荚决明花蕾。

Cassiabudanols A and B, Immunostimulative Diterpenoids with a Cassiabudane Carbon Skeleton Featuring a 3-Oxatetracyclo[6.6.1.0.0]pentadecane Scaffold from Cassia Buds.

机构信息

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.

State Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Key Laboratory of Plant Resources and Chemistry of Arid Zone , Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences , Urumqi 830011 , China.

出版信息

Org Lett. 2019 Jan 18;21(2):549-553. doi: 10.1021/acs.orglett.8b03883. Epub 2019 Jan 2.

Abstract

Two novel diterpenoids, cassiabudanols A (1) and B (2), were isolated from cassia buds. Their structures were determined by comprehensive spectroscopic analysis and single-crystal X-ray diffraction. Compounds 1 and 2 possess an unprecedented 11,14- cyclo-8,14:12,13-di- seco-isoryanodane (cassiabudane) carbon skeleton featuring a unique 3-oxatetracyclo[6.6.1.0.0]pentadecane bridged system, and their biosynthetic pathways are proposed. Compounds 1 and 2 exhibited significant immunostimulative activity, and the mode of action of 2 involves upregulating CD4 and CD8 T cells and downregulating Tregs.

摘要

从丁香花蕾中分离得到了两个新的二萜类化合物,丁香烷醇 A(1)和 B(2)。通过综合光谱分析和单晶 X 射线衍射确定了它们的结构。化合物 1 和 2 具有前所未有的 11,14-环-8,14:12,13-双-去甲异瑞香烷(丁香烷)碳骨架,具有独特的 3-氧杂十六环[6.6.1.0.0]十五烷桥系统,提出了它们的生物合成途径。化合物 1 和 2 表现出显著的免疫刺激活性,化合物 2 的作用模式涉及上调 CD4 和 CD8 T 细胞和下调 Tregs。

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