Organic synthesis of new putative lycopene metabolites and preliminary investigation of their cell-signaling effects

J Agric Food Chem. 2011 Feb 23;59(4):1457-63. doi: 10.1021/jf104092e. Epub 2011 Jan 19.

Abstract

Tomato is the main dietary source of lycopene, a carotenoid that is known to have protective effects on health and whose metabolites could also be involved in bioactivity. Herein we present the first organic synthesis of two potentially bioactive lycopene metabolites, namely, 10'-apolycopen-10'-oic acid (6) and 14'-apolycopen-14'-oic acid (13), which were obtained in their (all-E) stereoisomeric forms using Wittig and Horner-Wadsworth-Emmons type coupling reactions. Both molecules are shown to up-regulate the carotenoid asymmetric cleavage enzyme BCO2 while having no effect on BCO1 expression.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carotenoids / metabolism*
  • Dioxygenases
  • Fatty Acid Desaturases
  • Fatty Acids, Unsaturated / chemical synthesis*
  • Fatty Acids, Unsaturated / chemistry
  • Fatty Acids, Unsaturated / pharmacology
  • Fruit / chemistry
  • Gene Expression / drug effects
  • Lycopene
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Oxygenases / genetics
  • Signal Transduction*
  • Solanum lycopersicum / chemistry
  • Stereoisomerism
  • Testis / enzymology

Substances

  • 14'-apolycopen-14'-oic acid
  • 4,9,13,17,21-pentamethyldocosa-2,4,6,8,10,12,14,16,20-nonaenoic Acid
  • Fatty Acids, Unsaturated
  • Carotenoids
  • Oxygenases
  • beta-carotene ketolase
  • Dioxygenases
  • Fatty Acid Desaturases
  • BCO2 protein, human
  • Lycopene