Formation of phosphoglycosides in Caenorhabditis elegans: a novel biotransformation pathway

PLoS One. 2012;7(10):e46914. doi: 10.1371/journal.pone.0046914. Epub 2012 Oct 17.

Abstract

Background: Caenorhabditis elegans (C. elegans) has become a widely used model to explore the effect of food constituents on health as well as on life-span extension. The results imply that besides essential nutrients several flavonoids are able to impact the aging process. What is less investigated is the bioavailability and biotransformation of these compounds in C. elegans. In the present study, we focused on the soy isoflavone genistein and its metabolism in the nematode as a basis for assessing whether this model system mimics the mammalian condition.

Principal findings: C. elegans was exposed to 100 µM genistein for 48 hours. The worm homogenate was extracted and analyzed by liquid chromatography (LC). 11 metabolites of genistein were detected and characterized using LC electrospray ionization mass spectrometry. All genistein metabolites formed by C. elegans were found to be sugar conjugates, primarily genistein-O-glucosides. The dominant metabolite was identified as genistein-7-O-phosphoglucoside. Further interesting metabolites include two genistein-di-O-glycosides, a genistein-O-disaccharide as well as a genistein-O-phosphodisaccharide.

Conclusions/significance: Our study provides evidence for a novel biotransformation pathway in C. elegans leading to conjugative metabolites which are not known for mammals. The metabolism of genistein in mammals and in C. elegans differs widely which may greatly impact the bioactivity. These differences need to be appropriately taken into consideration when C. elegans is used as a model to assess possible health or aging effects.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biotransformation / drug effects
  • Caenorhabditis elegans / drug effects
  • Caenorhabditis elegans / metabolism*
  • Chromatography, Liquid
  • Genistein / administration & dosage
  • Genistein / chemistry
  • Genistein / pharmacology
  • Glycosides / chemistry
  • Glycosides / metabolism*
  • Humans
  • Metabolic Networks and Pathways* / drug effects
  • Spectrometry, Mass, Electrospray Ionization
  • Sugar Phosphates / chemistry
  • Sugar Phosphates / metabolism*
  • Time Factors
  • Tissue Extracts

Substances

  • Glycosides
  • Sugar Phosphates
  • Tissue Extracts
  • Genistein

Grants and funding

The work was supported by the Max Rubner-Institute, Federal Research Institute of Nutrition and Food, Germany. The funders had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript.