Isolation of brominated quinones showing chemiluminescence activity from luminous acorn worm, Ptychodera flava

Bioorg Med Chem. 2005 Apr 15;13(8):2741-7. doi: 10.1016/j.bmc.2005.02.028.

Abstract

Luminous acorn worm, Ptychodera flava emits green light by stimulating with diluted hydrogen peroxide. We have recently reported isolation and structure determination of 2,3,5,6-tetrabromohydroquinone as a luminous substance and riboflavin as a possible light emitter. There are three other luminous substances in the extracts from P. flava, so here we report the isolation and structure determination of other luminous substances as 2,3,5-tribromohydroquinone, tetrabromo-1,4-benzoquinone, and 2,3,5-tribromo-6-(2,3,5-tribromo-4-hydroxy-phenoxy)-benzene-1,4-diol. Besides, this is the first report of isolation of tetrabromo-1,4-benzoquinone from acorn worm. Structure-activity relationship of chemiluminescence activity of halogenated quinone derivatives reveals that a highly halogen substitution and 1,4-quinone skeleton are important for high chemiluminescence activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bromine / chemistry
  • Chordata, Nonvertebrate / chemistry*
  • Luminescent Measurements*
  • Molecular Structure
  • Quinones / chemistry*
  • Quinones / isolation & purification*
  • Species Specificity
  • Structure-Activity Relationship

Substances

  • Quinones
  • Bromine