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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MDPI AG
2024-11-01
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| Series: | Marine Drugs |
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| author | Junjie Yang Yuan Zong Cili Wang Kai Li Yue Zhang Pinglin Li |
| author_facet | Junjie Yang Yuan Zong Cili Wang Kai Li Yue Zhang Pinglin Li |
| author_sort | Junjie Yang |
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| description | 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. |
| format | Article |
| id | doaj-art-1aef32129b4b47c9b2492338e0c83d1c |
| institution | Kabale University |
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| language | English |
| publishDate | 2024-11-01 |
| publisher | MDPI AG |
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| series | Marine Drugs |
| spelling | doaj-art-1aef32129b4b47c9b2492338e0c83d1c2024-11-26T18:11:25ZengMDPI AGMarine Drugs1660-33972024-11-01221151710.3390/md22110517Heterocycles and a Sorbicillinoid from the Coral-Derived Fungus <i>Penicillium chrysogenum</i>Junjie Yang0Yuan Zong1Cili Wang2Kai Li3Yue Zhang4Pinglin Li5Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaShandong Academy of Chinese Medicine, Jinan 250014, ChinaKey Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaKey Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaA 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.https://www.mdpi.com/1660-3397/22/11/517coral-derived fungus<i>Penicillium chrysogenum</i>heterocyclessorbicillinoidcytotoxicity |
| spellingShingle | Junjie Yang Yuan Zong Cili Wang Kai Li Yue Zhang Pinglin Li Heterocycles and a Sorbicillinoid from the Coral-Derived Fungus <i>Penicillium chrysogenum</i> Marine Drugs coral-derived fungus <i>Penicillium chrysogenum</i> heterocycles sorbicillinoid cytotoxicity |
| title | Heterocycles and a Sorbicillinoid from the Coral-Derived Fungus <i>Penicillium chrysogenum</i> |
| title_full | Heterocycles and a Sorbicillinoid from the Coral-Derived Fungus <i>Penicillium chrysogenum</i> |
| title_fullStr | Heterocycles and a Sorbicillinoid from the Coral-Derived Fungus <i>Penicillium chrysogenum</i> |
| title_full_unstemmed | Heterocycles and a Sorbicillinoid from the Coral-Derived Fungus <i>Penicillium chrysogenum</i> |
| title_short | Heterocycles and a Sorbicillinoid from the Coral-Derived Fungus <i>Penicillium chrysogenum</i> |
| title_sort | heterocycles and a sorbicillinoid from the coral derived fungus i penicillium chrysogenum i |
| topic | coral-derived fungus <i>Penicillium chrysogenum</i> heterocycles sorbicillinoid cytotoxicity |
| url | https://www.mdpi.com/1660-3397/22/11/517 |
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