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Planta Med 2014; 80(11): 912-917
DOI: 10.1055/s-0034-1382859
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Vermistatin Derivatives with α-Glucosidase Inhibitory Activity from the Mangrove Endophytic Fungus Penicillium sp. HN29-3B1

Yayue Liu
1   School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, China
,
Guoping Xia
1   School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, China
,
Hanxiang Li
1   School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, China
,
Lin Ma
1   School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, China
,
Bo Ding
1   School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, China
,
Yongjun Lu
2   School of Life Sciences and Biomedical Center, Sun Yat-Sen University, Guangzhou, China
4   Key Laboratory of Functional Molecules from Oceanic Microorganisms (Sun Yat-Sen University), Department of Education of Guangdong Province, Guangzhou, China
,
Lei He
2   School of Life Sciences and Biomedical Center, Sun Yat-Sen University, Guangzhou, China
,
Xuekui Xia
3   Key Laboratory for Applied Microbiology of Shandong Province, Biotechnology Center of Shandong Academy of Sciences, Jinan, China
,
Zhigang She
1   School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, China
4   Key Laboratory of Functional Molecules from Oceanic Microorganisms (Sun Yat-Sen University), Department of Education of Guangdong Province, Guangzhou, China
› Author Affiliations
Further Information

Publication History

received 14 January 2014
revised 05 June 2014

accepted 13 June 2014

Publication Date:
12 August 2014 (online)

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Abstract

Three new vermistatin derivatives, 6-demethylpenisimplicissin (1), 5′-hydroxypenisimplicissin (2), and 2′′-epihydroxydihydrovermistatin (3), along with five known vermistatin analogues, methoxyvermistatin (4), vermistatin (5), 6-demethylvermistatin (6), hydroxyvermistatin (7), and penisimplicissin (8), were isolated from the culture of the mangrove endophytic fungus Penicillium sp. HN29-3B1 from Cerbera manghas. Their structures were elucidated mainly by nuclear magnetic resonance spectroscopy. The absolute configurations of compounds 1 and 2 were deduced on the basis of circular dichroism data. The absolute structures of compounds 3 and 5 were confirmed by a single-crystal X-ray diffraction experiment using Cu Kα radiation. In the bioactivity assay, compounds 1 and 3 exhibited α-glucosidase inhibitory activity with IC50 values of 9.5 ± 1.2 and 8.0 ± 1.5 µM, respectively. The plausible biosynthetic pathways for all compounds are discussed.

Key words

vermistatin - endophytic fungus - Trichocomaceae - Cerbera manghas - Penicillium sp. - α-glucosidase inhibitory activity

Supporting Information

 

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