Isatisindigoticanine A, a novel indole alkaloid with an unpresented carbon skeleton from the roots of Isatis tinctoria

Nat Prod Res. 2021 Apr;35(8):1249-1255. doi: 10.1080/14786419.2019.1644632. Epub 2019 Jul 22.

Abstract

Isatisindigoticanine A (1), a new indole alkaloid with an unusual carbon skeleton of a benzofuran-3-one unit connected with a 1H-indole-3-yl unit and a 4-(1,2-dihydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hexan-2-one unit via a C-3-C-8'' bond and a C-4'-C-8'' bond, was obtained from the roots of Isatis tinctoria. Its structure was determined by physicochemical properties and spectroscopic methods including 1 D, 2 D NMR, IR, HRESIMS data. The absolutely configurations were deduced by comparison of its experimental CD and calculated ECD spectra. Nitric oxide (NO) inhibitory activities of isatisindigoticanine A was also evaluated in the LPS-stimulated RAW 264.7 cells, however, no inhibitory effect was presented.

Keywords: Anti-inflammatory activity; Isatis tinctoria; indole alkaloid; isatisindigoticanine A.

MeSH terms

  • Animals
  • Carbon / chemistry
  • Circular Dichroism
  • Indole Alkaloids / chemistry*
  • Indole Alkaloids / pharmacology*
  • Isatis / chemistry*
  • Lipopolysaccharides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors
  • Plant Roots / chemistry
  • RAW 264.7 Cells
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Indole Alkaloids
  • Lipopolysaccharides
  • Nitric Oxide
  • Carbon