Heterocycles and a Sorbicillinoid from the Coral-Derived Fungus <i>Penicillium chrysogenum</i>
A detailed chemical study of the culture of a coral-derived fungus <i>Penicillium chrysogenum</i> resulted in the isolation and identification of four new aromatic heterocycles chrysoquinazolinones A–B (<b>1</b>–<b>2</b>) and chrysobenzothiazoles A–B (<b>3&l...
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| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-11-01
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| Series: | Marine Drugs |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1660-3397/22/11/517 |
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| Summary: | A detailed chemical study of the culture of a coral-derived fungus <i>Penicillium chrysogenum</i> resulted in the isolation and identification of four new aromatic heterocycles chrysoquinazolinones A–B (<b>1</b>–<b>2</b>) and chrysobenzothiazoles A–B (<b>3</b>–<b>4</b>), along with a new sorbicillinoid 4-carboxylsorbicillin (<b>5</b>). Chrysoquinazolinones A–B (<b>1</b>–<b>2</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 (<b>3</b>–<b>4</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 (±<b>3</b>) 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 <b>5</b> exhibited moderate cytotoxicity against K562 and NCI-H446 cell lines, with IC<sub>50</sub> values of 15.00 μM and 16.87 μM, respectively. |
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| ISSN: | 1660-3397 |