Cytotoxic anthrone-cyclopentenone heterodimers from the fungus Penicillium sp. guided by molecular networking.
10.1016/S1875-5364(25)60858-2
- Author:
Ruiyun HUO
1
;
Jiayu DONG
1
;
Gaoran LIU
1
;
Ying SHI
1
;
Ling LIU
2
Author Information
1. State Key Laboratory of Microbial Diversity and Innovative Utilization, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China; University of Chinese Academy of Sciences, Beijing 100049, China.
2. State Key Laboratory of Microbial Diversity and Innovative Utilization, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China; University of Chinese Academy of Sciences, Beijing 100049, China. Electronic address: liul@im.ac.cn.
- Publication Type:Journal Article
- Keywords:
Cytotoxic activity;
DP4+ (13)C NMR calculation;
HSQC-based SMART;
Mangrove-derived fungi;
Molecular networking;
Structure elucidation
- MeSH:
Humans;
Penicillium/chemistry*;
Molecular Structure;
Cyclopentanes/isolation & purification*;
Cell Line, Tumor;
Antineoplastic Agents/pharmacology*;
Tandem Mass Spectrometry;
Dimerization;
HeLa Cells;
Magnetic Resonance Spectroscopy
- From:
Chinese Journal of Natural Medicines (English Ed.)
2025;23(10):1259-1267
- CountryChina
- Language:English
-
Abstract:
(±)-Penicithrones A-D (1a/1b-4a/4b), four novel pairs of anthrone-cyclopentenone heterodimers characterized by a distinctive bridged 6/6/6-5 tetracyclic core skeleton, together with three previously identified compounds (5-7), were isolated from the crude extract of the mangrove-derived fungus Penicillium sp., guided by heteronuclear single quantum correlation (HSQC)-based small molecule accurate recognition technology (SMART 2.0) and liquid chromatography-tandem mass spectrometry (LC-MS/MS)-based molecular networking. The structural elucidation of new compounds was accomplished through comprehensive spectroscopic analysis, and their absolute configurations were determined using DP4+ 13C nuclear magnetic resonance (NMR) calculations and electronic circular dichroism (ECD) calculations. Compounds 1a/1b-4a/4b demonstrated moderate cytotoxicity against three human cancer cell lines HeLa, HCT116 and MCF-7 with half maximal inhibitory concentration (IC50) values ranging from 15.95 ± 1.64 to 28.56 ± 2.59 μmol·L-1.
