Changes in the triterpenoid content of cuticular waxes during fruit ripening of eight grape (Vitis vinifera) cultivars grown in the Upper Rhine Valley

J Agric Food Chem. 2014 Aug 13;62(32):7998-8007. doi: 10.1021/jf502033s. Epub 2014 Jul 30.

Abstract

Triterpenoids present in grape cuticular waxes are of interest due to their potential role in protection against biotic stresses, their impact on the mechanical toughness of the fruit surface, and the potential industrial application of these biologically active compounds from grape pomace. The determination of the triterpenoid profile of cuticular waxes reported here supplements existing knowledge of the chemical diversity of grape, with some compounds reported in this species for the first time. Common compounds identified in eight examined cultivars grown in the Upper Rhine Valley include oleanolic acid, oleanolic and ursolic acid methyl esters, oleanolic aldehyde, α-amyrin, α-amyrenone, β-amyrin, cycloartanol, 24-methylenecycloartanol, erythrodiol, germanicol, lupeol accompanied by lupeol acetate, campesterol, cholesterol, sitosterol, stigmasterol, and stigmasta-3,5-dien-7-one, whereas 3,12-oleandione was specific for the Muscat d'Alsace cultivar. Changes in the triterpenoid content of cuticular waxes were determined at three different phenological stages: young grapes, grapes at véraison (the onset of ripening), and mature grapes. The results reveal a characteristic evolution of triterpenoid content during fruit development, with a high level of total triterpenoids in young grapes that gradually decreases with a slight increase in the level of neutral triterpenoids. This phenomenon may partially explain changes in the mechanical properties of the cuticle and possible modulations in the susceptibility to pathogens of mature grapes.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Crops, Agricultural / chemistry
  • Crops, Agricultural / growth & development
  • Crops, Agricultural / metabolism*
  • Flame Ionization
  • France
  • Fruit / chemistry
  • Fruit / growth & development
  • Fruit / metabolism*
  • Functional Food / analysis
  • Gas Chromatography-Mass Spectrometry
  • Germany
  • Oleanolic Acid / analogs & derivatives
  • Oleanolic Acid / analysis
  • Oleanolic Acid / biosynthesis
  • Phytochemicals / analysis
  • Phytochemicals / biosynthesis
  • Phytochemicals / chemistry
  • Phytosterols / analysis
  • Phytosterols / biosynthesis
  • Phytosterols / chemistry
  • Pigments, Biological / metabolism
  • Plant Epidermis / chemistry
  • Plant Epidermis / growth & development
  • Plant Epidermis / metabolism*
  • Species Specificity
  • Triterpenes / analysis
  • Triterpenes / chemistry
  • Triterpenes / metabolism*
  • Vitis / chemistry
  • Vitis / growth & development
  • Vitis / metabolism*
  • Waxes / chemistry
  • Waxes / metabolism*
  • Wine

Substances

  • Phytochemicals
  • Phytosterols
  • Pigments, Biological
  • Triterpenes
  • Waxes
  • Oleanolic Acid