Metabolic fate of isotopes during the biological transformation of carbohydrates to 2,5-dimethyl-4-hydroxy-3(2H)-furanone in strawberry fruits

Martina Wein, Efraim Lewinsohn, Wilfried Schwab

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37 Scopus citations

Abstract

Isotopically labeled D-glucose, D-fructose, 1-deoxy-D-fructose, and 6-deoxyhexoses were applied to detached ripening strawberry (Fragaria x ananassa) fruits, and the incorporation of the isotopes into the key strawberry aroma compounds 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF, 1) and 2,5-dimethyl-4-methoxy-3(2H)-furanone (DMMF, 2) was determined by gas chromatography-mass spectrometry. In contrast to previous reports the data clearly showed that 6-deoxy-D-fructose/6-deoxy-D-glucose and 1-deoxy-D-fructose are not natural precursors of the furanones. However, isotopically labeled 1 and 2 were observed after the application of [1-2H]-, [2-2H]-, and [6,6-2H2]-D-glucose as well as [U-13C6]-, [1-13C]-, [1-2H]-, [6,6-2H2]-D-fructose. The isotope label of [4-2H]-D-glucose was not recovered in the furanones. In contrast, [2-2H]-D-glucose was converted to [1- or 6-2H]-1 and [1- or 6-2H]-2 by the strawberry fruits. The observed isotope shift can be explained by the catalysis of phosphohexose isomerase in the course of the biogenesis of the hydroxyfuranone (1) and the methoxyfuranone (2) from D-glucose. Thus, the applied D-glucose is metabolized to D-fructose-6-phosphate prior to the transformation into the furanones.

Original languageEnglish
Pages (from-to)2427-2432
Number of pages6
JournalJournal of agricultural and food chemistry
Volume49
Issue number5
DOIs
StatePublished - 2001
Externally publishedYes

Keywords

  • Biosynthesis
  • Flavor
  • Fragaria x ananassa
  • Furaneol
  • Strawberry

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