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.

An epigenetic modifier induces production of (10′ S )-verruculide B, an inhibitor of protein tyrosine phosphatases by Phoma sp. nov. LG0217, a fungal endophyte of Parkinsonia microphylla

“…Vermistatin ( 2 ) has been reported to act as an elastase inhibitor, 15 phytotoxin on various banana cultivars, 16 RNA synthesis inhibitor in Ehrlich ascites carcinoma, 17 P-388 leukemia, 17 weakly cytotoxic to KB tumor cell lines, 18 and an inhibitor of α -glucosidase. 19 Reported biological activities of nafuredin ( 5 ) include selective inhibition of helminth complex I and inhibition of NADH-fumarate reductase (NFRD) of Ascaris suum (pig roundworm) at nM concentrations. 14a Verruculide B has been evaluated previously for its inhibitory activity against protein tyrosine phosphatase (PTP) 1B (PTP1B) and was found to exhibit 40% inhibition at 23.1 μ M. 11 Therefore, it was of interest to evaluate 1 for its activity against other PTPs.…”

Performance evaluation of various cooling-lubrication techniques in grinding of hardened AISI 4340 steel with vitrified bonded CBN wheel

“…Vermistatin (2) has been reported to act as an elastase inhibitor, 15 phytotoxin on various banana cultivars, 16 RNA synthesis inhibitor in Ehrlich ascites carcinoma, 17 P-388 leukemia, 17 weakly cytotoxic to KB tumor cell lines, 18 and an inhibitor of a-glucosidase. 19 Reported biological activities of nafuredin (5) include selective inhibition of helminth complex I and inhibition of NADH-fumarate reductase (NFRD) of Ascaris suum (pig roundworm) at nM concentrations. 14a Verruculide B has been evaluated previously for its inhibitory activity against protein tyrosine phosphatase (PTP) 1B (PTP1B) and was found to exhibit 40% inhibition at 23.1 lM.…”

Chroman-4-one and pyrano[4,3-b]chromenone derivatives from the mangrove endophytic fungus Diaporthe phaseolorum SKS019

“…9,10 Marine-derived fungi are widely recognized as prolic sources of biologically active and structurally unique natural products. 3,11 As part of our ongoing investigation on bioactive metabolites from mangrove endophytic fungi, [12][13][14][15][16][17] a chemical investigation of the mangrove endophytic fungus Diaporthe phaseolorum SKS019, isolated from a fresh branch of the mangrove plant Acanthus ilicifolius, was carried out. The CH 2 Cl 2 extract of a fermentation broth of the fungus led to the isolation and identication of four chroman-4-one derivatives (1)(2)(3)(4), and ve pyrano [4,3-b]chromenone derivatives (5a-7).…”