np0c00396_si_001.pdf (12.33 MB)
Artemyrianolides A–S, Cytotoxic Sesquiterpenoids from Artemisia myriantha
journal contribution
posted on 2020-08-26, 04:29 authored by Shuang Tang, Xin-Tian Zhang, Yun-Bao Ma, Xiao-Yan Huang, Chang-An Geng, Tian-Ze Li, Xue-Mei Zhang, Cheng Shen, Li-Hua Su, Zhen Gao, Ji-Jun ChenRandom screening suggested that the
EtOH extract of Artemisia
myriantha (Asteraceae) and its EtOAc fraction had cytotoxicity
against HepG2 cells with inhibitory ratios of 30.6% and 53.5% at 50.0
μg/mL. Bioassay-guided isolation of the most active fractions
(Fr. C and Fr. D) afforded 19 new sesquiterpenolides, artemyrianolides
A–S (1–19), involving 13 germacranolides
(1–13), four guaianolides (14–17), and two eudesmanolides (18 and 19), together with 16 known sesquiterpenoids
(20–35). The new compounds were characterized
by physical data analyses (HRESIMS, IR, 1D and 2D NMR, ECD), and the
absolute configurations of compounds 1, 2, and 11 were determined by X-ray crystallography. Structurally,
compounds 2 and 11–13 maintain an uncommon cis-fused 10/5 bicyclic system
and compound 12 possesses an unusual (7S) configuration. Twenty of the compounds exhibited cytotoxicity against
HepG2, Huh7, and SMMC-7721 cell lines. Compound 9 showed
cytotoxic activity on both HepG2 and Huh7 cells with IC50 values of 8.6 and 8.8 μM, and compounds 8 and 33 showed cytotoxicity to the three human hepatoma cell lines
with IC50 values of 4.9 and 7.4 μM (HepG2), 4.3 and
7.8 μM (Huh7), and 3.1 and 9.8 μM (SMMC-7721), respectively.
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1 D8.8 μ M9.8 μ M13 germacranolidescytotoxic activityEtOAc fractionArtemisia myriantha Random screening7.4 μ MHuh 7 cellsIC 50 values7.8 μ MArtemisia myrianthaCompound 9hepatoma cell lines2 D NMRECDcompounds 1compounds 2compounds 8X-ray crystallographySMMC -7721 cell linescompound 12IRcytotoxicitydata analysesHepG 2 cellsHRESIMSHepG 2
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