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Metabolic fate of isotopes during the biological transformation of carbohydrates to 2,5-dimethyl-4-hydroxy-3(2H)-furanone in strawberry fruits
Year:
2001
Authors :
Lewinsohn, Efraim
;
.
Volume :
49
Co-Authors:
Wein, M., Lehrst. für Lebensmittelchemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Lewinsohn, E., Division of Aromatic Plants, ARO, Newe ya'ar, P.O. Box 1021, Ramat Yishai 30095, Israel
Schwab, W., Lehrst. für Lebensmittelchemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Facilitators :
From page:
2427
To page:
2432
(
Total pages:
6
)
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.
Note:
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More details
DOI :
10.1021/jf010072p
Article number:
Affiliations:
Database:
Scopus
Publication Type:
article
;
.
Language:
English
Editors' remarks:
ID:
32847
Last updated date:
02/03/2022 17:27
Creation date:
17/04/2018 01:13
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Scientific Publication
Metabolic fate of isotopes during the biological transformation of carbohydrates to 2,5-dimethyl-4-hydroxy-3(2H)-furanone in strawberry fruits
49
Wein, M., Lehrst. für Lebensmittelchemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Lewinsohn, E., Division of Aromatic Plants, ARO, Newe ya'ar, P.O. Box 1021, Ramat Yishai 30095, Israel
Schwab, W., Lehrst. für Lebensmittelchemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Metabolic fate of isotopes during the biological transformation of carbohydrates to 2,5-dimethyl-4-hydroxy-3(2H)-furanone in strawberry fruits
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.
Scientific Publication
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