中国科学院昆明植物研究所陈纪军团队报道了蒿素A-S、杜松烷型倍半萜类二聚体及其抗肝癌活性研究。相关研究成果发表在2024年3月7日出版的《中国化学》。

从黑沙蒿中分离到19个新的含倍半萜二聚体的杜松烷，蒿素A-S（1-19）和13个已知的SDs（20-32）。通过综合光谱分析、X射线单晶衍射、理论ECD和NMR计算，确定了它们的结构和绝对构型。

在化学上，蒿甲醚A-F（1-6）是由前所未有的C-3C-15′或C-3C-13′单键，与氧化重排的6/5/6/6稠环系统构建的两个杜松烷单元的第一个例子；蒿素G-K（7-11）通过[4+2]环加成反应进行生物连接，蒿素G-J（7-10）具有新的5/6/6/6/5-庚环稠环体系。蒿素L-S（12-19）是由三种不同类型的倍半萜类化合物通过酯化反应形成的。

抗肝癌实验表明，最具活性的化合物蒿素B和H（2和8）对三种肝癌细胞株具有抑制作用，其IC50分别为26.9和25.1μmol/L（HepG2）、29.5和18.3μmol/L（Huh7）、19.7和15.7μmol/L（SK-Hep-1）。

附：英文原文

Title: Artemordins A-S, Cadinane-Type Sesquiterpenoid Dimers from Artemisia ordosica and Their Antihepatoma Activities

Author: Yuan Wang, Tian-Ze Li, Yun-Bao Ma, Chang-An Geng, Yong-Cui Wang, Ji-Jun Chen

Issue&Volume: 2024-03-07

Abstract: Nineteen new cadinane-involving sesquiterpenoid dimers, artemordins A—S (1—19), together with 13 known SDs (20—32) were isolated from Artemisia ordosica. Their structures and absolute configurations were established by comprehensive spectral analyses, X-ray single crystal diffraction, theoretical ECD, and NMR calculations. Chemically, artemordins A—F (1—6) were the first examples of two cadinane units constructed by unprecedented C-3C-15′ or C-3C-13′ single bond with an oxido-rearranged 6/5/6/6 fused ring system; artemordins G—K (7—11) were biogenetically connected by [4 + 2] cycloaddition reaction and artemordins G—J (7—10) possessed a novel 5/6/6/6/6/6/5-heptacyclic fused ring system. Artemordins L—S (12—19) were formed by esterification, which involved three different types of sesquiterpenoids. Antihepatoma assay suggested that the most active compounds, artemordins B and H (2 and 8), exhibited inhibitory activities on three hepatoma cell lines with IC50 values of 26.9 and 25.1 μmol/L (HepG2), 29.5 and 18.3 μmol/L (Huh7), 19.7 and 15.7 μmol/L (SK-Hep-1).

DOI: 10.1002/cjoc.202400032

Source: https://onlinelibrary.wiley.com/doi/full/10.1002/cjoc.202400032