Artemordosins A-L, cadinane-monoterpene heterodimers and sesquiterpenoids with antihepatoma activity from Artemisia ordosica

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

doi:10.1016/j.phytochem.2024.114374

Artemordosins A-L, cadinane-monoterpene heterodimers and sesquiterpenoids with antihepatoma activity from Artemisia ordosica

Phytochemistry. 2024 Dec 19:114374. doi: 10.1016/j.phytochem.2024.114374. Online ahead of print.

Authors

Yuan Wang¹, Tian-Ze Li², Yun-Bao Ma², Chang-An Geng², Yong Cui Wang², Ji-Jun Chen³

Affiliations

¹ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; University of Chinese Academy of Sciences, Beijing 100049, PR China.
² State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China.
³ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China; University of Chinese Academy of Sciences, Beijing 100049, PR China. Electronic address: chenjj@mail.kib.ac.cn.

PMID: 39708992
DOI: 10.1016/j.phytochem.2024.114374

Abstract

Two unprecedented sesquiterpene and monoterpene heterodimers and ten previously undescribed sesquiterpenoids, artemordosins A-L (1-12), as well as ten known sesquiterpenoids (13-22), were obtained from Artemisia ordosica. Their structures were elucidated based on comprehensive analyses of NMR, IR, HRESIMS, GIAO NMR calculations with DP4+ probability analysis, and ECD calculations. Notably, artemordosins A and B (1 and 2) were the first examples of cadinane-monoterpene dimers, and artemordosin A (1) was a cadinane-myrceane heterodimer with a 6/6/6/6 ring system formed by [4 + 2] cycloaddition, while artemordosin B (2) was a 4,5-seco-cadinane-artemisane dimer connected through a C-5-O-C-4' linkage. Artemordosin C (3) was the first example of 10(5→4)-abeo-eudesmane sesquiterpenoid featuring an unprecedented bicyclo[5.3.0]decane skeleton in natural products. Artemordosin B (2) and epi-deoxyarteannuin B (14) showed inhibitory activity on three hepatoma cells with IC₅₀ values of 37.1 and 15.4 μM (HepG2), 27.7 and 16.4 μM (Huh-7), 39.6 and 22.6 μM (SK-Hep-1).

Keywords: Antihepatoma activity; Artemisia ordosica; Artemordosins A−L; Cadinane; Eudesmane; Sesquiterpene and monoterpene heterodimers.