Antiviral Butyrolactones from the Endophytic Fungus Aspergillus versicolor

Min Zhou; Gang Du; Hai-Ying Yang; Cong-Fang Xia; Juan-Xia Yang; Yan-qing Ye; Xue-Mei Gao; Xiao-Nian Li; Qiu-Fen Hu

doi:10.1055/s-0034-1396153

Planta Medica, Inhaltsverzeichnis

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

Authors

Min Zhou

¹Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities, Kunming, P. R. China

²State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, P. R. China
Gang Du

¹Key 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

¹Key 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

¹Key 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

¹Key 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

¹Key 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

¹Key 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

²State 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

¹Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan University of Nationalities, Kunming, P. R. China

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

Volltext

Referenzen

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