Anti-inflammatory Eudesmane Sesquiterpenoids from Artemisia hedinii

• Published in: Journal of natural products (Washington, D.C.) Vol. 84; no. 5; pp. 1626 - 1637
• Main Authors: Wang, Xing, Peng, Xia, Tang, Chunping, Zhou, Shuaizhen, Ke, Chang-Qiang, Liu, Yueling, Yao, Sheng, Ai, Jing, Ye, Yang
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society and American Society of Pharmacognosy 28-05-2021
• Subjects: Animals; Anti-Inflammatory Agents - isolation & purification; Anti-Inflammatory Agents - pharmacology; Artemisia - chemistry; Cells, Cultured; China; Cytokines; Female; Macrophages - drug effects; Mice; Mice, Inbred C57BL; Molecular Structure; Phytochemicals - isolation & purification; Phytochemicals - pharmacology; Sesquiterpenes, Eudesmane - isolation & purification; Sesquiterpenes, Eudesmane - pharmacology; China
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.1c00177

Fourteen new eudesmane sesquiterpenoids (1, 3–5, 7–16) and seven known analogues were isolated from the whole plant of Artemisia hedinii. Their structures were elucidated by spectroscopic data analysis and comparison with published NMR data, and their absolute configurations were confirmed by X-ray diffraction experiments and TDDFT ECD calculation. Compounds 1–15 were identified as eudesmane acids, which represent a kind of lactone ring-opening eudesmane-type sesquiterpenes with an acetoxyl or a hydroxy group attached to C-9. Compounds 1 and 2, 5 and 6, and 7 and 8 are three pairs of epimers isomerized at C-3, C-5, and C-11, respectively. Compounds 1–9, 11–13, 15–19, and 21 could influence the proinflammatory phenotype of the M1 macrophage. Among them, compounds 5, 8, 9, 12, 16, and 19 consistently exhibited anti-inflammatory effects, as evidenced by downregulating classic pro-inflammatory cytokines TNF-α, IL-12, IL-6, and IFN-γ in LPS-induced primary bone marrow derived M1 macrophages.