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Article

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

1
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
2
Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao 266235, China
3
Shandong Academy of Chinese Medicine, Jinan 250014, China
4
Key Laboratory of Marine Food Processing & Safety Control, College of Food Science and Engineering, Ocean University of China, Qingdao 266003, China
*
Author to whom correspondence should be addressed.
Mar. Drugs 2024, 22(11), 517; https://doi.org/10.3390/md22110517
Submission received: 23 October 2024 / Revised: 12 November 2024 / Accepted: 13 November 2024 / Published: 15 November 2024
(This article belongs to the Special Issue Pharmacological Potential of Marine Natural Products, 2nd Edition)

Abstract

A detailed chemical study of the culture of a coral-derived fungus Penicillium chrysogenum resulted in the isolation and identification of four new aromatic heterocycles chrysoquinazolinones A–B (12) and chrysobenzothiazoles A–B (34), along with a new sorbicillinoid 4-carboxylsorbicillin (5). Chrysoquinazolinones A–B (12) 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 (34) 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 (±3) 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 5 exhibited moderate cytotoxicity against K562 and NCI-H446 cell lines, with IC50 values of 15.00 μM and 16.87 μM, respectively.
Keywords: coral-derived fungus; Penicillium chrysogenum; heterocycles; sorbicillinoid; cytotoxicity coral-derived fungus; Penicillium chrysogenum; heterocycles; sorbicillinoid; cytotoxicity
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MDPI and ACS Style

Yang, J.; Zong, Y.; Wang, C.; Li, K.; Zhang, Y.; Li, P. Heterocycles and a Sorbicillinoid from the Coral-Derived Fungus Penicillium chrysogenum. Mar. Drugs 2024, 22, 517. https://doi.org/10.3390/md22110517

AMA Style

Yang J, Zong Y, Wang C, Li K, Zhang Y, Li P. Heterocycles and a Sorbicillinoid from the Coral-Derived Fungus Penicillium chrysogenum. Marine Drugs. 2024; 22(11):517. https://doi.org/10.3390/md22110517

Chicago/Turabian Style

Yang, Junjie, Yuan Zong, Cili Wang, Kai Li, Yue Zhang, and Pinglin Li. 2024. "Heterocycles and a Sorbicillinoid from the Coral-Derived Fungus Penicillium chrysogenum" Marine Drugs 22, no. 11: 517. https://doi.org/10.3390/md22110517

APA Style

Yang, J., Zong, Y., Wang, C., Li, K., Zhang, Y., & Li, P. (2024). Heterocycles and a Sorbicillinoid from the Coral-Derived Fungus Penicillium chrysogenum. Marine Drugs, 22(11), 517. https://doi.org/10.3390/md22110517

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