Iteamine, the first alkaloid isolated from Itea virginica L. inflorescence

Phytochemistry. 2014 Apr:100:126-31. doi: 10.1016/j.phytochem.2014.01.012. Epub 2014 Feb 14.

Abstract

Iteamine, o-aminobenzyl β-D-glucopyranoside, is the first alkaloid to be isolated from Itea virginica. Itea is the sole plant source of D-psicose, a rare sugar likely to be a major dietary supplement. The structure of iteamine was established by NMR and confirmed by total synthesis. Iteamine and its galacto-analog (which was not found in Itea plants) showed no strong inhibition of any of the 15 glycosidases tested; unnatural galacto-iteamine was a weak inhibitor of chicken liver α-N-acetylgalactosaminidase.

Keywords: Grossulariaceae; Itea virginica; Iteamine; d-Psicose; α-N-acetylgalactosaminidase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology*
  • Animals
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology*
  • Glucosides
  • Inflorescence / chemistry*
  • Tracheophyta / chemistry*
  • alpha-N-Acetylgalactosaminidase / antagonists & inhibitors

Substances

  • Alkaloids
  • Enzyme Inhibitors
  • Glucosides
  • iteamine
  • alpha-N-Acetylgalactosaminidase