Artemordins A—S, Cadinane‐Type Sesquiterpenoid Dimers from Artemisia ordosica and Their Antihepatoma Activities

• Published in: Chinese journal of chemistry Vol. 42; no. 13; pp. 1493 - 1508
• Main Authors: Wang, Yuan, Li, Tian‐Ze, Ma, Yun‐Bao, Geng, Chang‐An, Wang, Yong‐Cui, Chen, Ji‐Jun
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY‐VCH Verlag GmbH & Co. KGaA 01.07.2024; Wiley; Wiley Subscription Services, Inc
• Subjects: Antihepatoma activities; Artemisia ordosica; Artemordins A—S; Cadinane‐type sesquiterpenoid dimers; Cell lines; Chemistry; Chemistry, Multidisciplinary; Cycloaddition; Cytotoxicity; Dimers; Esterification; Hepatoma; Natural products; NMR; Nuclear magnetic resonance; Physical Sciences; Science & Technology; Sesquiterpenoids; Single crystals; Terpenoids; Artemordins A-S; Artemisia ordosica; NATURAL DISESQUITERPENOIDS; Antihepatoma activities; Terpenoids; Natural products; Cytotoxicity; Cadinane-type sesquiterpenoid dimers
• ISSN: 1001-604X; 1614-7065
• DOI: 10.1002/cjoc.202400032

Comprehensive Summary 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‐3−C‐15′ or C‐3−C‐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). Nineteen new cadinane‐involving sesquiterpenoid dimer, artemordins A—S (1—19) were isolated from Artemisia ordosica. Notably, artemordins A—F (1—6) were the first examples of two cadinane units connected by unprecedented C—C single bond with an oxido‐rearranged 6/5/6/6 fused ring system; artemordins G—J (7—10) were biogenetically formed by [4 + 2] cycloaddition and possessed a novel 5/6/6/6/6/6/5—heptacyclic fused ring system. 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).