title: Vermistatin derivatives with α-glucosidase inhibitory activity from the mangrove endophytic fungus Penicillium sp. HN29-3B1.
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.
authors.affiliation: School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, China.
authors.forename: Yayue
authors.initials: Y
authors.lastname: Liu
authors.affiliation: School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, China.
authors.forename: Guoping
authors.initials: G
authors.lastname: Xia
authors.affiliation: School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, China.
authors.forename: Hanxiang
authors.initials: H
authors.lastname: Li
authors.affiliation: School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, China.
authors.forename: Lin
authors.initials: L
authors.lastname: Ma
authors.affiliation: School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, China.
authors.forename: Bo
authors.initials: B
authors.lastname: Ding
authors.affiliation: School of Life Sciences and Biomedical Center, Sun Yat-Sen University, Guangzhou, China.
authors.forename: Yongjun
authors.initials: Y
authors.lastname: Lu
authors.affiliation: School of Life Sciences and Biomedical Center, Sun Yat-Sen University, Guangzhou, China.
authors.forename: Lei
authors.initials: L
authors.lastname: He
authors.affiliation: Key Laboratory for Applied Microbiology of Shandong Province, Biotechnology Center of Shandong Academy of Sciences, Jinan, China.
authors.forename: Xuekui
authors.initials: X
authors.lastname: Xia
authors.affiliation: School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, China.
authors.forename: Zhigang
authors.initials: Z
authors.lastname: She
mesh_terms: D029062:Apocynaceae / Q000382:microbiology*; D060026:Endophytes; D065089:Glycoside Hydrolase Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D014961:X-Ray Diffraction; D000520:alpha-Glucosidases / Q000187:drug effects
chemical_list: C000597141:2'-epihydroxydihydrovermistatin; C000597140:5'-hydroxypenisimplicissin; C000597139:6-demethylpenisimplicissin; D065089:Glycoside Hydrolase Inhibitors; D011753:Pyrones; C051060:vermistatin; D000520:alpha-Glucosidases