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Mar. Drugs 2012, 10(6), 1297-1306; doi:10.3390/md10061297

Quinazolin-4-one Coupled with Pyrrolidin-2-iminium Alkaloids from Marine-Derived Fungus Penicillium aurantiogriseum

1
CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China
2
Graduate University of Chinese Academy of Sciences, Beijing 100049, China
3
Hisun Pharmaceutical Co. Ltd., Taizhou 318000, China
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 9 April 2012 / Revised: 29 May 2012 / Accepted: 29 May 2012 / Published: 7 June 2012
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Abstract

Three new alkaloids, including auranomides A and B (1 and 2), a new scaffold containing quinazolin-4-one substituted with a pyrrolidin-2-iminium moiety, and auranomide C (3), as well as two known metabolites auranthine (4) and aurantiomides C (5) were isolated from the marine-derived fungus Penicillium aurantiogriseum. The chemical structures of compounds 13 were elucidated by extensive spectroscopic methods, including IR, HRESIMS and 2D NMR spectroscopic analysis. The absolute configurations of compounds 13 were suggested from the perspective of a plausible biosynthesis pathway. Compounds 13 were subjected to antitumor and antimicrobial screening models. Auranomides A–C exhibited moderate cytotoxic activity against human tumor cells. Auranomides B was the most potent among them with an IC50 value of 0.097 μmol/mL against HEPG2 cells.
Keywords: marine-derived fungus; Penicillium aurantiogriseum; quinazolin-4-one; antitumor marine-derived fungus; Penicillium aurantiogriseum; quinazolin-4-one; antitumor
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Song, F.; Ren, B.; Yu, K.; Chen, C.; Guo, H.; Yang, N.; Gao, H.; Liu, X.; Liu, M.; Tong, Y.; Dai, H.; Bai, H.; Wang, J.; Zhang, L. Quinazolin-4-one Coupled with Pyrrolidin-2-iminium Alkaloids from Marine-Derived Fungus Penicillium aurantiogriseum. Mar. Drugs 2012, 10, 1297-1306.

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