LC-MS guided isolation of diterpenoids from Sapium insigne with α-glucosidase inhibitory activities

Fitoterapia. 2018 Jul:128:57-65. doi: 10.1016/j.fitote.2018.03.009. Epub 2018 Apr 8.

Abstract

Ten new (1-10) and ten known (11-20) diterpenoids involving ent-atisane, ent-seco-atisane, ent-kaurane and ent-seco-kaurane types were isolated from Sapium insigne under the guidance of LCMS-IT-TOF analyses. Their structures were characterized by extensive spectroscopic analyses (HRESIMS, UV, IR, 1D and 2D NMR). A putative biosynthetic pathway was proposed for ent-seco-atisane diterpenoids. Their inhibitory activities on α-glucosidase in vitro were tested for the first time. Compound 4 showed moderate inhibitory effect on α-glucosidase with an IC50 value of 0.34 mM via a noncompetitive inhibition mechanism (Ki = 0.27 mM). The preliminary structure-activity relationships of the ent-atisane diterpenoids inhibiting α-glucosidase were discussed.

Keywords: Ent-atisane; Noncompetitive inhibition; Sapium insigne; α-Glucosidase.

MeSH terms

  • Chromatography, Liquid
  • Diterpenes / isolation & purification*
  • Glycoside Hydrolase Inhibitors
  • Molecular Structure
  • Plant Stems / chemistry
  • Sapium / chemistry*
  • Structure-Activity Relationship
  • Tandem Mass Spectrometry
  • alpha-Glucosidases / isolation & purification*

Substances

  • Diterpenes
  • Glycoside Hydrolase Inhibitors
  • alpha-Glucosidases