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Penicamide A, A Unique N,N′-Ketal Quinazolinone Alkaloid from Ascidian-Derived Fungus Penicillium sp. 4829

School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China
Southern Laboratory of Ocean Science and Engineering (Guangdong, Zhuhai), Zhuhai 519000, China
Department of Marine Science, Faculty of Fisheries, Kasetsart University, Bangkok 10900, Thailand
Institute of chemical sciences, Gomal University, Dera Ismail Khan 27100, Pakistan
Authors to whom correspondence should be addressed.
Mar. Drugs 2019, 17(9), 522;
Received: 21 August 2019 / Revised: 2 September 2019 / Accepted: 2 September 2019 / Published: 5 September 2019
(This article belongs to the Special Issue Advances in Marine Alkaloids)
Previously unreported N,N′-ketal quinazolinone enantiomers [(−)-1 and (+)-1] and a new biogenetically related compound (2), along with six known compounds, 2-pyrovoylaminobenzamide (3), N-(2-hydroxypropanoyl)-2 amino benzoic acid amide (4), pseurotin A (5), niacinamide (6), citreohybridonol (7), citreohybridone C (8) were isolated from the ascidian-derived fungus Penicillium sp. 4829 in wheat solid-substrate medium culture. Their structures were elucidated by a combination of spectroscopic analyses (1D and 2D NMR and Electron Circular Dichroism data) and X-ray crystallography. The enantiomeric pair of 1 is the first example of naturally occurring N,N′-ketal quinazolinone possessing a unique tetracyclic system having 4-quinazolinone fused with tetrahydroisoquinoline moiety. The enantiomeric mixtures of 1 displayed an inhibitory effect on NO production in lipopolysaccharide-activated RAW264.7 cells, while the optically pure (–)-1 showed better inhibitory effect than (+)-1. View Full-Text
Keywords: ascidian-derived fungus; quinazolinone alkaloid; Penicillium; anti-inflammatory ascidian-derived fungus; quinazolinone alkaloid; Penicillium; anti-inflammatory
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MDPI and ACS Style

Chen, S.; Jiang, M.; Chen, B.; Salaenoi, J.; Niaz, S.-I.; He, J.; Liu, L. Penicamide A, A Unique N,N′-Ketal Quinazolinone Alkaloid from Ascidian-Derived Fungus Penicillium sp. 4829. Mar. Drugs 2019, 17, 522.

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