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阿塔托罗芬醇 A 和 B:来自. 的两种笼状倍半萜

Artatrovirenols A and B: Two Cagelike Sesquiterpenoids from .

机构信息

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences; Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, People's Republic of China.

University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.

出版信息

J Org Chem. 2020 Nov 6;85(21):13466-13471. doi: 10.1021/acs.joc.0c01491. Epub 2020 Oct 22.

Abstract

Artatrovirenols A and B ( and ), two novel cagelike sesquiterpenoids, possess a unique 5/5/6/5/5-pentacyclic and a 5/5/6/5-tetracyclic system with an unprecedented tetracyclo[5.3.1.1.0]dodecane scaffold from . The structures of compounds and including their absolute stereochemistry were elucidated through extensive spectroscopic analyses, X-ray crystallography, and quantum chemical calculations. Plausible biosynthetic pathways for the new isolates were proposed from the naturally occurring arglabin () via the key intramolecular Diels-Alder cycloaddition. Compound showed cytotoxicity against three human hepatoma cell lines (HepG2, SMMC-7721, and Huh7) with half maximal inhibitory concentration values of 123.8, 44.0, and 142.6 μΜ, respectively.

摘要

阿塔病毒醇 A 和 B(和),两种新型笼状倍半萜,具有独特的 5/5/6/5/5-五环和 5/5/6/5-四环系统,具有前所未有的四环[5.3.1.1.0]十二烷支架,来自 Artabotrys hexapetalus。化合物和的结构,包括它们的绝对立体化学,通过广泛的光谱分析、X 射线晶体学和量子化学计算得以阐明。从天然存在的阿塔戈宾()通过关键的分子内 Diels-Alder 环加成,提出了新分离物的可能生物合成途径。化合物对三种人肝癌细胞系(HepG2、SMMC-7721 和 Huh7)表现出细胞毒性,半数最大抑制浓度值分别为 123.8、44.0 和 142.6 μM。

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