Two novel enantiomers from metarhizium flavoviride and their inhibitory activities against α-glucosidase

• Published in: Journal of molecular structure 2022-09, Vol.1264, p.133322, Article 133322
• Main Authors: Wei, Jie, Zhao, Cheng, Ji, Guiying, Dong, Mei, Lu, Ruili, Huang, Bo, Bao, Guanhu, Hu, Fenglin
• Format: Article
• Language: English
• Subjects: Enantiomers; Metarhizium flavoviride; Molecular docking; Α-glucosidase inhibitor
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2022.133322

•Two novel enantiomers were obtained from metarhizium flavoviride and named metarrhiziumoids a and b.•Both metarrhiziumoids a and b have α-glycosidase inhibitory activity, and the activity of metarrhiziumoids b is stronger than that of metarrhiziumoids a.•Molecular docking results show that the two enantiomers have different optimal docking modes and the binding energy for the metarrhiziumoids b was lower than that for metarrhiziumoids a. A pair of novel enantiomers metarrhiziumoids A (R-enantiomer, 14.3 mg) and B (S-enantiomer, 9.5 mg) were isolated from 3.0 g extract of Metarhizium flavoviride by silica gel column chromatography combined with preparative and semi-preparative HPLC, and identified with high resolution mass, 1D, 2D NMR and circular dichroism. Targets prediction showed that the two compounds had glycosidase inhibitory activity. Result of α-glycosidase inhibitory tests showed that the both enantiomers were competitive inhibitors of α-glycosidase, and the bioactivity of metarrhiziumoids B (IC50 = 174 μg/mL) was stronger than that of metarrhiziumoids A (IC50 = 259 μg/mL). Molecular docking results show that the two enantiomers have different optimal docking modes and the binding energy for the S-enantiomer (-7.8 kcal/mol) was lower than for the R-enantiomer (-7.20 kcal/mol). The docking mode selections and binding energy differences resulted in the inhibitory activity difference. [Display omitted]