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

Publikation: Beitrag in FachzeitschriftArtikelBegutachtung

37 Zitate (Scopus)

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.

OriginalspracheEnglisch
Seiten (von - bis)2427-2432
Seitenumfang6
FachzeitschriftJournal of agricultural and food chemistry
Jahrgang49
Ausgabenummer5
DOIs
PublikationsstatusVeröffentlicht - 2001
Extern publiziertJa

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