Structure Revisions of Phenolic Bisabolane Sesquiterpenes and a Ferroptosis Inhibitor from the Marine-Derived Fungus Aspergillus versicolor YPH93

Seven new phenolic bisabolane sesquiterpenoids (1–7), along with 10 biogenetically related analogues (8–17), were obtained from the deep-sea-derived fungus Aspergillus versicolor YPH93. The structures were elucidated based on extensive analyses of the spectroscopic data. Compounds 1–3 are the first...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2023-04, Vol.86 (4), p.830-841
Main Authors: Li, Yuanli, Shi, Jiayi, Liu, Ruzhen, Liu, Yu, Liu, Ruifeng, Wu, Zongmin, Xu, Wei, Ma, Huabin, Luo, Hai-Bin, Cheng, Zhongbin
Format: Article
Language:English
Subjects:
Aspergillus - chemistry
Ferroptosis
Hydrogen Peroxide
Molecular Structure
Monocyclic Sesquiterpenes
Phenols - pharmacology
Sesquiterpenes - chemistry
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Summary:Seven new phenolic bisabolane sesquiterpenoids (1–7), along with 10 biogenetically related analogues (8–17), were obtained from the deep-sea-derived fungus Aspergillus versicolor YPH93. The structures were elucidated based on extensive analyses of the spectroscopic data. Compounds 1–3 are the first examples of phenolic bisabolanes that contain two hydroxy groups attached to the pyran ring. The structures of sydowic acid derivatives (1–6 and 8–10) were carefully studied, leading to the structure revisions of six known analogues, including a revision of the absolute configuration for sydowic acid (10). All metabolites were evaluated for their effects on ferroptosis. Compound 7 exerted inhibition on erastin/RSL3-induced ferroptosis with EC50 values ranging from 2 to 4 μM, while it exhibited no effects on TNFα-induced necroptosis or H2O2-induced cell necrosis.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.2c01022