Heterocycles and a Sorbicillinoid from the Coral-Derived Fungus Penicillium chrysogenum

• Published in: Marine drugs 2024-11, Vol.22 (11), p.517
• Main Authors: Yang, Junjie, Zong, Yuan, Wang, Cili, Li, Kai, Zhang, Yue, Li, Pinglin
• Format: Article
• Language: English
• Subjects: Animals; Anthozoa - microbiology; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Aquatic Organisms; Aromatic compounds; Benzothiazole; Biological Products - chemistry; Biological Products - isolation & purification; Biological Products - pharmacology; Carbon; Cell culture; Cell Line, Tumor; Cell lines; coral-derived fungus; Corals; Crystallography; Crystallography, X-Ray; Cytotoxicity; Enantiomers; Fungi; heterocycles; Heterocyclic compounds; Heterocyclic Compounds - chemistry; Heterocyclic Compounds - isolation & purification; Heterocyclic Compounds - pharmacology; High performance liquid chromatography; HPLC; Humans; K562 Cells; Liquid chromatography; Marine invertebrates; Marine organisms; Metabolites; Molecular Structure; Natural products; Penicillium chrysogenum; Penicillium chrysogenum - chemistry; Single crystals; sorbicillinoid; Stereoisomers
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md22110517

A detailed chemical study of the culture of a coral-derived fungus resulted in the isolation and identification of four new aromatic heterocycles chrysoquinazolinones A-B ( - ) and chrysobenzothiazoles A-B ( - ), along with a new sorbicillinoid 4-carboxylsorbicillin ( ). Chrysoquinazolinones A-B ( - ) combine a quinazolinone fragment with a bicyclo[2.2.2]octane or a pyrrolidone moiety, respectively, demonstrating the unexpected structures of marine natural products. Chrysobenzothiazoles A-B ( - ) possess a benzothiazole system and are the second isolation of this class of skeleton compounds from marine organisms. The existence of the pair of enantiomers (± ) was deduced by chiral HPLC analysis. Their structures and absolute configurations were elucidated by detailed spectroscopic analysis, comparison with the literature data, single-crystal X-ray crystallographic analysis and TDDFT-ECD calculations. Compound exhibited moderate cytotoxicity against K562 and NCI-H446 cell lines, with IC values of 15.00 μM and 16.87 μM, respectively.