Electrophilic Aromatic Deuteration of Lignans: Mostly Reliable but Occasionally Aberrant Selectivities

J Agric Food Chem. 2015 Sep 9;63(35):7595-605. doi: 10.1021/acs.jafc.5b00214. Epub 2015 Apr 13.

Abstract

Lignans are a ubiquitous group of natural products of plant or mammalian origin. In the human diet, especially in fiber-rich foods, there are measurable amounts of lignans. Lignan intake is associated with a reduced risk of a range of chronic Western diseases, and in studying these compounds and their biological activity, authentic stable isotope labeled analogues are needed. This review summarizes the reported labeling methods and discusses the selectivity and reactivity in the electrophilic aromatic deuteration of lignans where recently a number of unexpected selectivities or nonselectivities have been encountered.

Keywords: deuteration; lignan; reactivity; selectivity; stable isotope labeling.

Publication types

  • Review

MeSH terms

  • Animals
  • Deuterium / chemistry*
  • Deuterium / metabolism
  • Humans
  • Isotope Labeling
  • Lignans / chemistry*
  • Lignans / metabolism
  • Molecular Structure

Substances

  • Lignans
  • Deuterium