Thiolactones and Δ^8,9-Pregnene Steroids from the Marine-Derived Fungus <i>Meira</i> sp. 1210CH-42 and Their <i>α</i>-Glucosidase Inhibitory Activity

Abstract

The fungal genus Meira was first reported in 2003 and has mostly been found on land. This is the first report of second metabolites from the marine-derived yeast-like fungus Meira sp. One new thiolactone (1), along with one revised thiolactone (2), two new Δ8,9-steroids (4, 5), and one known Δ8,9-steroid (3), were isolated from the Meira sp. 1210CH-42. Their structures were elucidated based on the comprehensive spectroscopic data analysis of 1D, 2D NMR, HR-ESIMS, ECD calculations, and the pyridine-induced deshielding effect. The structure of 5 was confirmed by oxidation of 4 to semisynthetic 5. In the α-glucosidase inhibition assay, compounds 2–4 showed potent in vitro inhibitory activity with IC50 values of 148.4, 279.7, and 86.0 μM, respectively. Compounds 2–4 exhibited superior activity as compared to acarbose (IC50 = 418.9 μM).

Keywords

• marine fungus
• natural product
• <i>Meira</i> sp.
• thiolactone
• pregnene steroid
• epimer