Cyclohexenoneterpenes A−J: Cytotoxic meroterpenoids from mangrove-associated fungus Penicillium sp. N-5

Ten previously undescribed meroterpenoids, cyclohexenoneterpenes A−J (1−7, 18−20), together with 10 known analogues (8−17) were isolated from the mangrove-associated fungus Penicillium sp. N-5. Their structures were elucidated on the basis of extensive spectroscopic and mass spectrometric data. The...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2023-11, Vol.215, p.113868-113868, Article 113868
Main Authors: Chen, Tao, Liu, Yufeng, Huang, Yun, Yang, Wencong, Sun, Bing, Tan, Qi, Wei, Tianyu, Wang, Bo, Yuan, Jie, She, Zhigang
Format: Article
Language:English
Subjects:
Cytotoxicity
Mangrove-associated fungus
Meroterpenoid
Penicillium
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Summary:Ten previously undescribed meroterpenoids, cyclohexenoneterpenes A−J (1−7, 18−20), together with 10 known analogues (8−17) were isolated from the mangrove-associated fungus Penicillium sp. N-5. Their structures were elucidated on the basis of extensive spectroscopic and mass spectrometric data. The absolute configurations of the undescribed compounds were assigned by electronic circular dichroism calculations, the modified Mosher's method, NMR calculations and DP4+ analysis. In the bioassay, compounds 10, 11, 15, and 20 exhibited cytotoxicities against SNB-19, MDA-MB-231, MDA-MB-435 and HCT-116 cell lines with IC50 values ranging from 1.4 to 19.1 μM. [Display omitted] •Ten undescribed meroterpenoids were isolated from the mangrove-associated fungus.•The modified Mosher's method was used to determine the absolute configurations.•Isoprenoid epoxycyclohexenone type of meroterpenoids have cytotoxic activities.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2023.113868