1. Vermistatin Derivatives with α-Glucosidase Inhibitory Activity from the Mangrove Endophytic Fungus Penicillium sp. HN29-3B1
- Author
-
Hanxiang Li, Xuekui Xia, Lin Ma, Bo Ding, Guoping Xia, Zhigang She, Yongjun Lu, Yayue Liu, and Lei He
- Subjects
Circular dichroism ,Stereochemistry ,Pharmaceutical Science ,Biology ,Analytical Chemistry ,Cerbera manghas ,chemistry.chemical_compound ,X-Ray Diffraction ,Drug Discovery ,Endophytes ,Glycoside Hydrolase Inhibitors ,Pharmacology ,Trichocomaceae ,Molecular Structure ,Organic Chemistry ,Penicillium ,Vermistatin ,alpha-Glucosidases ,Nuclear magnetic resonance spectroscopy ,Endophytic fungus ,biology.organism_classification ,Apocynaceae ,Complementary and alternative medicine ,chemistry ,Pyrones ,Molecular Medicine ,Mangrove - 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.
- Published
- 2014