Highly Modified Sesquiterpene Lactones with Cytotoxic Activities from Strobocalyx chunii

Three new germacranolide sesquiterpene lactones (SLs), strochunolides A–C (1–3, respectively), and a new guaianolide SL, strochunolide D (4), were isolated from Strobocalyx chunii and structurally characterized. Compound 1 is the first example of a dihomo-germacranolide SL, characterized by an unpre...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-08, Vol.88 (15), p.11122-11129
Main Authors: Ge, Zhan-Peng, Gao, Yuan, Zhang, Yan, Liu, Hong-Chun, Zhao, Jin-Xin, Yue, Jian-Min
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemistry
Asteraceae
Humans
Lactones - chemistry
Lactones - pharmacology
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
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Summary:Three new germacranolide sesquiterpene lactones (SLs), strochunolides A–C (1–3, respectively), and a new guaianolide SL, strochunolide D (4), were isolated from Strobocalyx chunii and structurally characterized. Compound 1 is the first example of a dihomo-germacranolide SL, characterized by an unprecedented 6/10/5 tricyclic scaffold incorporating an additional fused δ-lactone C-ring. The structure of a known germacranolide SL, spicatolide C (5), was revised as its 8-epimer. Compound 3 exhibited potent in vitro cytotoxic activity against the HL-60 cell line, with an IC50 value of 0.18 ± 0.01 μM.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01104