Structure and biogenesis of jolkinin, a highly oxygenated ellagitannin from Euphorbia jolkinii

J Nat Prod. 2004 Jun;67(6):1018-22. doi: 10.1021/np0400297.

Abstract

A new ellagitannin, jolkinin (2), was isolated from the fresh whole plant of Euphorbia jolkinii, and its structure, including absolute configuration, was determined on the basis of spectroscopic and chemical evidence. A highly oxygenated acyl group with unique hexacyclic structure is attached to the 2,4-positions of 1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-beta-d-glucopyranose. The structural similarity to elaeocarpusin (4) suggests that jolkinin is produced by a condensation reaction between ascorbic acid and geraniin (1), the dominant ellagitannin in this plant, which contains a dehydrohexahydroxydiphenoyl group. A plausible mechanism for jolkinin formation is also proposed.

MeSH terms

  • Euphorbia / chemistry*
  • Glucosides / chemistry
  • Hydrolyzable Tannins*
  • Japan
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism
  • Tannins / chemistry*
  • Tannins / isolation & purification
  • Tannins / metabolism

Substances

  • Glucosides
  • Hydrolyzable Tannins
  • Tannins
  • ellagitannin
  • jolkinin
  • Geraniin