Synthesis of (3S,3'S)- and meso-stereoisomers of alloxanthin and determination of absolute configuration of alloxanthin isolated from aquatic animals

Mar Drugs. 2014 May 8;12(5):2623-32. doi: 10.3390/md12052623.

Abstract

In order to determine the absolute configuration of naturally occurring alloxanthin, a HPLC analytical method for three stereoisomers 1a-c was established by using a chiral column. Two authentic samples, (3S,3'S)- and meso-stereoisomers 1b and 1c, were chemically synthesized according to the method previously developed for (3R,3'R)-alloxanthin (1a). Application of this method to various alloxanthin specimens of aquatic animals demonstrated that those isolated from shellfishes, tunicates, and crucian carp are identical with (3R,3'R)-stereoisomer 1a, and unexpectedly those from lake shrimp, catfish, biwa goby, and biwa trout are mixtures of three stereoisomers of 1a-c.

MeSH terms

  • Animals
  • Bivalvia
  • Crustacea
  • Fishes
  • Molecular Conformation
  • Mollusca
  • Stereoisomerism
  • Urochordata
  • Xanthophylls / chemical synthesis
  • Xanthophylls / chemistry*

Substances

  • Xanthophylls
  • alloxanthin