Antioxidant and α-Glucosidase Inhibitory Activities Guided Isolation and Identification of Components from Mango Seed Kernel

Oxid Med Cell Longev. 2020 Dec 28:2020:8858578. doi: 10.1155/2020/8858578. eCollection 2020.

Abstract

In the present study, petroleum ether, dichloromethane, ethyl acetate, and n-butanol fractions of mango seed kernel exhibited different degrees of antioxidant and α-glucosidase inhibitory activity. Thus, quantitative and qualitative analysis of the petroleum ether fraction was conducted by GC-MS. Among identified components, four unsaturated fatty acids had never been reported in natural products before, together with 19 known components. In addition, 17 compounds were isolated and elucidated from other active fractions. Compounds 2, 9, 15, and 17 were isolated for the first time from Mangifera genus. Compounds 1 and 2 exhibited prominent DPPH radical scavenging and α-glucosidase inhibitory effects. In order to further explore their mechanism of α-glucosidase inhibition, their enzyme kinetics and in silico modeling experiments were performed. The results indicated that 1 inhibited α-glucosidase in a noncompetitive manner, whereas 2 acted in a competitive manner. In molecular docking, the stability of binding was enhanced by π-π T-shaped, π-alkyl, π-π stacked, hydrogen bond, and electrostatic interactions. Thus, compounds 1 and 2 were determined to be new potent antioxidant and α-glucosidase inhibitors for preventing food oxidation and enhancing hypoglycemic activity.

MeSH terms

  • Antioxidants / pharmacology*
  • Biphenyl Compounds / chemistry
  • Free Radical Scavengers / chemistry
  • Gas Chromatography-Mass Spectrometry
  • Glycoside Hydrolase Inhibitors / pharmacology*
  • Kinetics
  • Mangifera / chemistry*
  • Molecular Docking Simulation
  • Phytochemicals / pharmacology
  • Picrates / chemistry
  • Plant Extracts / pharmacology
  • Seeds / chemistry*
  • alpha-Glucosidases / metabolism*

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Free Radical Scavengers
  • Glycoside Hydrolase Inhibitors
  • Phytochemicals
  • Picrates
  • Plant Extracts
  • 1,1-diphenyl-2-picrylhydrazyl
  • alpha-Glucosidases