Artematrovirenolides A-D and Artematrolides S-Z, Sesquiterpenoid Dimers with Cytotoxicity against Three Hepatoma Cell Lines from Artemisia atrovirens

doi:10.1002/cjoc.202100528

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	Artematrovirenolides A-D and Artematrolides S-Z, Sesquiterpenoid Dimers with Cytotoxicity against Three Hepatoma Cell Lines from Artemisia atrovirens
	Su,Li-Hua ; Li,Tian-Ze ; Ma,Yun-Bao ; Geng,Chang-An ; Huang,Xiao-Yan ; Zhang,Xin ; Gao,Zhen ; Chen,Ji-Jun
	2022
Source Publication	CHINESE JOURNAL OF CHEMISTRY
ISSN	1001-604X
Volume	40 Issue:1 Pages:104-114
Abstract	Comprehensive Summary Inspired by the intriguing structures and remarkable activities of sesquiterpenoid dimers, 12 new sesquiterpenoid dimers, artematrovirenolides A-D (1-4) and artematrolides S-Z (8-12), were isolated from the EtOAc fraction of Artemisia atrovirens through a bioactivity-guided approach. Their structures were elucidated by comprehensive spectroscopic data and absolute configuration was assigned based on single crystal X-ray diffraction data and ECD calculations. Structurally, all compounds are presumably formed via [4+2] cycloaddition involving three connecting model. Compounds 1-4 are four novel hetero-dimeric [4+2] Diels-Alder adducts dimerized from a rotundane-type unit and a guaiane-type monomer, and compounds 5-12 are eight new homo-dimeric [4+2] adducts derived from two guaianolide moieties. A putative biosynthetic pathway for compounds 1-4 was also proposed. Compounds 4, 6, 7, and 10 demonstrated moderate cytotoxicity against HepG2, SMMC-7721, and Huh7 cell lines with IC50 values ranging from 9.3 to 62.3 mu mol/L. Interestingly, compounds 5 and 11 manifested cytotoxicity with IC50 values of 13.6 and 12.8 (HepG2), 18.5 and 13.1 (SMMC-7721), and 16.5 and 19.4 mu mol/L (Huh7), respectively, which were equivalent to the positive control, sorafenib. This investigation suggests that compounds 5 and 11 might be considered as potent antihepatoma candidates and deserve further structural modification and mechanism study.
Keyword	Artemisia atrovirens Sesquiterpenoid dimers Structure elucidation X-ray diffraction Antihepatoma activity GUAIANOLIDE ARGYI
DOI	10.1002/cjoc.202100528
WOS ID	WOS:000722182400001
Citation statistics
Document Type	期刊论文
Identifier	http://ir.kib.ac.cn/handle/151853/73750
Collection	中国科学院昆明植物研究所
Affiliation	1.[Su, Li-Hua 2.Li, Tian-Ze 3.Ma, Yun-Bao 4.Geng, Chang-An 5.Huang, Xiao-Yan 6.Zhang, Xin 7.Gao, Zhen 8.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Yunnan Key Lab Nat Med Chem, Kunming 650201, Yunnan, Peoples R China 9.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation GB/T 7714	Su,Li-Hua,Li,Tian-Ze,Ma,Yun-Bao,et al. Artematrovirenolides A-D and Artematrolides S-Z, Sesquiterpenoid Dimers with Cytotoxicity against Three Hepatoma Cell Lines from Artemisia atrovirens[J]. CHINESE JOURNAL OF CHEMISTRY,2022,40(1):104-114.
APA	Su,Li-Hua.,Li,Tian-Ze.,Ma,Yun-Bao.,Geng,Chang-An.,Huang,Xiao-Yan.,...&Chen,Ji-Jun.(2022).Artematrovirenolides A-D and Artematrolides S-Z, Sesquiterpenoid Dimers with Cytotoxicity against Three Hepatoma Cell Lines from Artemisia atrovirens.CHINESE JOURNAL OF CHEMISTRY,40(1),104-114.
MLA	Su,Li-Hua,et al."Artematrovirenolides A-D and Artematrolides S-Z, Sesquiterpenoid Dimers with Cytotoxicity against Three Hepatoma Cell Lines from Artemisia atrovirens".CHINESE JOURNAL OF CHEMISTRY 40.1(2022):104-114.

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