Tuscan Varieties of Sweet Cherry Are Rich Sources of Ursolic and Oleanolic Acid: Protein Modeling Coupled to Targeted Gene Expression and Metabolite Analyses

Molecules. 2019 Apr 22;24(8):1590. doi: 10.3390/molecules24081590.

Abstract

The potential of six ancient Tuscan sweet cherry (Prunus avium L.) varieties as a source of health-promoting pentacyclic triterpenes is here evaluated by means of a targeted gene expression and metabolite analysis. By using a sequence homology criterion, we identify five oxidosqualene cyclase genes (OSCs) and three cytochrome P450s (CYP85s) that are putatively involved in the triterpene production pathway in sweet cherries. We performed 3D structure prediction and induced-fit docking using cation intermediates and reaction products for some OSCs to predict their function. We show that the Tuscan varieties have different amounts of ursolic and oleanolic acids and that these variations are related to different gene expression profiles. This study stresses the interest of valorizing ancient fruits as alternative sources of functional molecules with nutraceutical value. It also provides information on sweet cherry triterpene biosynthetic genes, which could be the object of follow-up functional studies.

Keywords: Prunus avium L.; Tuscan varieties; bioinformatics; cytochrome P450; gene expression; oxidosqualene cyclase; pentacyclic triterpenes.

MeSH terms

  • Cytochrome P-450 Enzyme System* / biosynthesis
  • Cytochrome P-450 Enzyme System* / genetics
  • Fruit* / genetics
  • Fruit* / metabolism
  • Gene Expression Regulation, Enzymologic / physiology*
  • Gene Expression Regulation, Plant / physiology*
  • Models, Biological*
  • Oleanolic Acid* / biosynthesis
  • Oleanolic Acid* / genetics
  • Plant Proteins* / biosynthesis
  • Plant Proteins* / genetics
  • Prunus avium* / genetics
  • Prunus avium* / metabolism
  • Triterpenes / metabolism*
  • Ursolic Acid

Substances

  • Plant Proteins
  • Triterpenes
  • Oleanolic Acid
  • Cytochrome P-450 Enzyme System