Indole alkaloid glycosides from Isatis tinctoria roots

Nat Prod Res. 2021 Jan;35(2):244-250. doi: 10.1080/14786419.2019.1624960. Epub 2019 Jun 7.

Abstract

Isatindigoside A and B (1 - 2), two new indole alkaloid glycosides along with five known ones (3 - 7) were obtained from the roots of I. tinctoria. Their structures were determined as isatindigoside A (1), isatindigoside B (2), isatindosulfonicacid A 3-O-β-D-glucopyranoside (3), indole-3-acetonitrile 6-O-β-D-glucopyranoside (4), isatindigobisindoloside A (5), isatindigobisindoloside B (6) isatindigobisindoloside F (7), by physicochemical properties and spectroscopic methods including 1 D, 2 D NMR, IR, HR-ESI-MS data. Nitric oxide (NO) inhibitory activities of all of the isolated compounds (1 - 7) were also evaluated. Compounds 2 and 7 showed inhibitory effects against LPS-stimulated RAW 264.7 cells with IC50 values of 27.6 μM and 18.8 μM, respectively.

Keywords: Isatis tinctoria; anti-inflammatory activity; indole alkaloid glycosides; structure determination.

MeSH terms

  • Animals
  • Drug Evaluation, Preclinical
  • Glycosides / chemistry
  • Indole Alkaloids / chemistry*
  • Indole Alkaloids / pharmacology*
  • Indoles / chemistry
  • Isatis / chemistry*
  • Lipopolysaccharides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / metabolism
  • Plant Roots / chemistry
  • RAW 264.7 Cells
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Glycosides
  • Indole Alkaloids
  • Indoles
  • Lipopolysaccharides
  • Nitric Oxide
  • indole-3-acetonitrile