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Cytotoxic Polyketides Isolated from the Deep-Sea-Derived Fungus Penicillium chrysogenum MCCC 3A00292

1
Key Laboratory of Marine Genetic Resources, State Key Laboratory Breeding Base of Marine Genetic Resources, Fujian Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China
2
College of life science, Jiangxi Normal University, Nanchang 330022, China
*
Authors to whom correspondence should be addressed.
The authors contributed equally to this work.
Mar. Drugs 2019, 17(12), 686; https://doi.org/10.3390/md17120686
Received: 13 November 2019 / Revised: 28 November 2019 / Accepted: 2 December 2019 / Published: 5 December 2019
The chemical examination of the solid cultures of the deep-sea-derived fungus Penicillium chrysogenum MCCC 3A00292 resulted in the isolation of three new versiol-type analogues, namely peniciversiols A–C (13), and two novel lactone derivatives, namely penicilactones A and B (6 and 7), along with 11 known polyketides. The planar structures of the new compounds were determined by the comprehensive analyses of the high-resolution electrospray ionization mass spectroscopy (HRESIMS) and nuclear magnetic resonance (NMR) data, while their absolute configurations were resolved on the basis of comparisons of the experimental electronic circular dichroism (ECD) spectra with the calculated ECD data. Compound 1 is the second example of versiols featuring a 2,3-dihydropyran-4-one ring. Additionally, compounds 6 and 7 are the first representatives of γ-lactone derivatives constructed by a 1,3-dihydroxy-5-methylbenzene unit esterifying with the α-methyl-γ-hydroxy-γ-acetic acid α,β-unsaturated-γ-lactone moiety and α-hydroxy-γ-methyl-γ-acetic acid α,β-unsaturated-γ-lactone unit, respectively. All of the isolated compounds were evaluated for their cytotoxic activities against five human cancer cell lines of BIU-87, ECA109, BEL-7402, PANC-1, and Hela-S3. Compound 1 exhibited a selective inhibitory effect against the BIU-87 cell line (IC50 = 10.21 μM), while compounds 4, 5, 8, and 1216 showed inhibitory activities against the ECA109, BIU-87, and BEL-7402 cell lines with the IC50 values ranging from 7.70 to > 20 μM. View Full-Text
Keywords: Deep-sea-derived fungus; Penicillium chrysogenum; polyketides; versiol; cytotoxic activities Deep-sea-derived fungus; Penicillium chrysogenum; polyketides; versiol; cytotoxic activities
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Niu, S.; Xia, M.; Chen, M.; Liu, X.; Li, Z.; Xie, Y.; Shao, Z.; Zhang, G. Cytotoxic Polyketides Isolated from the Deep-Sea-Derived Fungus Penicillium chrysogenum MCCC 3A00292. Mar. Drugs 2019, 17, 686.

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