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Planta Med 2015; 81(03): 235-240
DOI: 10.1055/s-0034-1396153
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Antiviral Butyrolactones from the Endophytic Fungus Aspergillus versicolor

Min Zhou
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities, Kunming, P. R. China
2   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, P. R. China
,
Gang Du
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities, Kunming, P. R. China
,
Hai-Ying Yang
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities, Kunming, P. R. China
,
Cong-Fang Xia
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities, Kunming, P. R. China
,
Juan-Xia Yang
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities, Kunming, P. R. China
,
Yan-qing Ye
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities, Kunming, P. R. China
,
Xue-Mei Gao
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities, Kunming, P. R. China
,
Xiao-Nian Li
2   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, P. R. China
,
Qiu-Fen Hu
1   Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities, Kunming, P. R. China
› Author Affiliations
Further Information

Publication History

received 05 August 2014
revised 24 November 2014

accepted 28 November 2014

Publication Date:
15 January 2015 (online)

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Abstract

Versicolactones A–D (1–4), four new butyrolactones, along with four known butyrolactones (5–8) were isolated from the fermentation products of the endophytic fungus Aspergillus versicolor. The structures of compounds 1–4, including absolute configuration, were elucidated by interpretation of the NMR and CD data. Compound 2 was further confirmed by single-crystal X-ray diffraction analysis. In particular, compound 1 is the first naturally occurring butyrolactone possessing an unusual 2-oxopropyl group. More importantly, compounds 1 and 8 displayed significant antitobacco mosaic virus activities with inhibition rates of 46.4 % and 35.4 %, even more potent than the positive control ningnanmycin (30.8 %). Compound 1 also showed moderate cytotoxicity against A549 and MCF7 cells with IC50 values of 3.2 and 2.5 µM, respectively.

Key words

Aspergillus versicolor - butyrolactones - Trichocomaceae - antitobacco mosaic virus activity - cytotoxicity

Supporting Information

 

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