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Quinazolin-4-one coupled with pyrrolidin-2-iminium alkaloids from marine-derived fungus Penicillium aurantiogriseum.
Mar Drugs. 2012 Jun; 10(6):1297-1306.MD

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 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 IC(50) value of 0.097 μmol/mL against HEPG2 cells.

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Authors+Show Affiliations

CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China.

CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China. Graduate University of Chinese Academy of Sciences, Beijing 100049, China.

CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China. Graduate University of Chinese Academy of Sciences, Beijing 100049, China.

CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China.

CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China.

CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China.

CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China.

CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China.

CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China.

CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China. Graduate University of Chinese Academy of Sciences, Beijing 100049, China.

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.

Hisun Pharmaceutical Co. Ltd., Taizhou 318000, China.

CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China.

MeSH

AlkaloidsAnti-Bacterial AgentsAntifungal AgentsAntineoplastic AgentsAquatic OrganismsBiological ProductsDrug Screening Assays, AntitumorHep G2 CellsHumansK562 CellsMagnetic Resonance SpectroscopyPenicilliumPyrrolidinesQuinazolinones

Pub Type(s)

Journal Article

Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22822373

Citation

Song, Fuhang, et al. "Quinazolin-4-one Coupled With Pyrrolidin-2-iminium Alkaloids From Marine-derived Fungus Penicillium Aurantiogriseum." Marine Drugs, vol. 10, no. 6, 2012, pp. 1297-1306.

Song F, Ren B, Yu K, et al. Quinazolin-4-one coupled with pyrrolidin-2-iminium alkaloids from marine-derived fungus Penicillium aurantiogriseum. Mar Drugs. 2012;10(6):1297-1306.

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. (2012). Quinazolin-4-one coupled with pyrrolidin-2-iminium alkaloids from marine-derived fungus Penicillium aurantiogriseum. Marine Drugs, 10(6), 1297-1306. https://doi.org/10.3390/md10061297

Song F, et al. Quinazolin-4-one Coupled With Pyrrolidin-2-iminium Alkaloids From Marine-derived Fungus Penicillium Aurantiogriseum. Mar Drugs. 2012;10(6):1297-1306. PubMed PMID: 22822373.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Quinazolin-4-one coupled with pyrrolidin-2-iminium alkaloids from marine-derived fungus Penicillium aurantiogriseum. AU - Song,Fuhang, AU - Ren,Biao, AU - Yu,Ke, AU - Chen,Caixia, AU - Guo,Hui, AU - Yang,Na, AU - Gao,Hong, AU - Liu,Xueting, AU - Liu,Mei, AU - Tong,Yaojun, AU - Dai,Huanqin, AU - Bai,Hua, AU - Wang,Jidong, AU - Zhang,Lixin, Y1 - 2012/06/07/ PY - 2012/04/09/received PY - 2012/05/29/revised PY - 2012/05/29/accepted PY - 2012/7/24/entrez PY - 2012/7/24/pubmed PY - 2012/12/21/medline KW - Penicillium aurantiogriseum KW - antitumor KW - marine-derived fungus KW - quinazolin-4-one SP - 1297 EP - 1306 JF - Marine drugs JO - Mar Drugs VL - 10 IS - 6 N2 - 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 IC(50) value of 0.097 μmol/mL against HEPG2 cells. SN - 1660-3397 UR - https://www.unboundmedicine.com/medline/citation/22822373/Quinazolin_4_one_coupled_with_pyrrolidin_2_iminium_alkaloids_from_marine_derived_fungus_Penicillium_aurantiogriseum_ L2 - https://www.mdpi.com/resolver?pii=md10061297 DB - PRIME DP - Unbound Medicine ER -