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

Marine Drugs

Fuhang Song¹  Biao Ren¹  Ke Yu¹  Caixia Chen¹  Hui Guo¹  Na Yang¹  Hong Gao¹  Xueting Liu¹  Mei Liu¹  Yaojun Tong¹  Huanqin Dai¹  Hua Bai²  Jidong Wang² 

[1] CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China;Hisun Pharmaceutical Co. Ltd., Taizhou 318000, China;

关键词: marine-derived fungus;    Penicillium aurantiogriseum;    quinazolin-4-one;    antitumor;   

DOI  :  10.3390/md10061297

来源: mdpi

【 摘 要 】

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 1–3 were elucidated by extensive spectroscopic methods, including IR, HRESIMS and 2D NMR spectroscopic analysis. The absolute configurations of compounds 1–3 were suggested from the perspective of a plausible biosynthesis pathway. Compounds 1–3 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.

【 授权许可】

CC BY   
© 2012 by the authors; licensee MDPI, Basel, Switzerland.