New quinone sulfates from the crinoids Tropiometra afra macrodiscus and Oxycomanthus japonicus

Chem Pharm Bull (Tokyo). 2002 Dec;50(12):1609-12. doi: 10.1248/cpb.50.1609.

Abstract

Quinone pigments in the crinoids were investigated. New quinone sulfates 1 and 3 were isolated from Tropiometra afra macrodiscus and Oxycomanthus japonicus, respectively. The structures 1 and 3 were determined to be 1,6,8-trihydroxy-3-propylanthraquinone-2-carboxylic acid 6-O-sulfate (ptilometric acid 6-O-sulfate) and 2-butanoyl-3,6,8-trihydroxy-1,4-naphtoquinone 6-O-sulfate, respectively, by chemical and spectroscopic analysis. Ptilometric acid 6-O-sulfate (1) showed an antifeedant activity on fish.

MeSH terms

  • Animals
  • Anthraquinones / isolation & purification*
  • Anthraquinones / pharmacology
  • Echinodermata / chemistry*
  • Feeding Behavior / drug effects
  • Fishes
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Quinones / isolation & purification*
  • Quinones / pharmacology
  • Structure-Activity Relationship

Substances

  • Anthraquinones
  • Quinones
  • ptilometric acid 6-O-sulfate