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Open AccessArticle

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

1
School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China
2
Southern Laboratory of Ocean Science and Engineering (Guangdong, Zhuhai), Zhuhai 519000, China
3
Department of Marine Science, Faculty of Fisheries, Kasetsart University, Bangkok 10900, Thailand
4
Institute of chemical sciences, Gomal University, Dera Ismail Khan 27100, Pakistan
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2019, 17(9), 522; https://doi.org/10.3390/md17090522
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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