Covalent interaction of ascorbic acid with natural products

Phytochemistry. 2009 Dec;70(17-18):1930-9. doi: 10.1016/j.phytochem.2009.09.028. Epub 2009 Oct 28.

Abstract

While ascorbic acid (vitamin C) is mostly known as a cofactor for proline hydroxylase and as a biological antioxidant, it also forms covalent bonds with natural products which we here refer to as 'ascorbylation'. A number of natural products containing an ascorbate moiety has been isolated and characterized from a variety of biological sources, ranging from marine algae to flowering plants. Most of these compounds are formed either as a result of nucleophilic substitution or addition by ascorbate, e.g. the ascorbigens from Brassica species are ascorbylated indole derivatives. Some ascorbylated tannins appear to be formed from electrophilic addition to dehydroascorbic acid. There are also examples of annulations of ascorbate with dietary polyphenols, e.g. epigallocatechin gallate (EGCG) and resveratrol derivatives. Herein is a survey of 33 ascorbylated natural products and their reported biological activities.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Ascorbic Acid / analogs & derivatives
  • Ascorbic Acid / chemistry
  • Ascorbic Acid / metabolism*
  • Eukaryota*
  • Flavonoids / metabolism
  • Flavonoids / pharmacology
  • Molecular Structure
  • Phenols / metabolism
  • Phenols / pharmacology
  • Plant Extracts / chemistry
  • Plant Extracts / metabolism*
  • Plant Extracts / pharmacology
  • Polyphenols

Substances

  • Flavonoids
  • Phenols
  • Plant Extracts
  • Polyphenols
  • Ascorbic Acid