Evidence for an NIH shift as the origin of the apparently anomalous distribution of deuterium in estragole from Artemisia dracunculus

J Nat Prod. 2000 May;63(5):713-5. doi: 10.1021/np990457q.

Abstract

Feeding experiments of [2-(2)H]- and [4'-(2)H]phenylalanine in Artemisia dracunculus validate the hypothesis that the marked difference in deuterium content at the natural abundance level between the aromatic carbons of estragole (1) is due to an NIH shift during the hydroxylation of the benzene ring.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allylbenzene Derivatives
  • Anisoles / chemistry*
  • Anisoles / metabolism
  • Artemisia / chemistry*
  • Artemisia / metabolism
  • Deuterium
  • Isotope Labeling
  • Magnetic Resonance Spectroscopy
  • Oils, Volatile / chemistry*
  • Oils, Volatile / metabolism
  • Phenylalanine / metabolism
  • Plants, Medicinal*

Substances

  • Allylbenzene Derivatives
  • Anisoles
  • Oils, Volatile
  • Phenylalanine
  • estragole
  • Deuterium