Identification of Passion Fruit Glycosides by Gas Chromatography/Mass Spectrometry

Journal of Agricultural and Food Chemistry

Volumn 46, Issue 10, 1998, Pages 4352-4357

  Chassagne, David ^a   Crouzet, Jean ^a   Bayonove, Claude L ^b   Baumes, Raymond L ^b  

^a UNIV MONTPELLIER   (France)

^b CEMAGREF   (France)

Author keywords

Gas chromatography; Gas chromatography mass spectrometry; Glycosidally bound compounds; Passion fruit

Indexed keywords

PASSIFLORA EDULIS; PASSIFLORA LIGULARIS;

EID: 0001761927     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf980416k     Document Type: Article

References (34)

1. Albersteim, P.; Nevins, D. J.; English, P. D.; Karr, A. A method for the analysis of sugars in plant cell-wall polysaccharides by gas - liquid chromatography. Carbohydr. Res. 1967, 5, 340-345.
2. Arana, F. Action of a β-glucosidase in the curing of vanillia. Food Res. 1943, 8, 343-351.
3. Baltenweck-Guyot, R.; Trendel, J. M.; Albrecht, P.; Schaeffer A. Mono- and diglycosides of (E)-6,9-dihydroxymegastigma-4,7-dien-3-one in Vitis vinifera wine. Phytochemistry 1996, 43, 621-624.
4. 13 norisoprenoid glucosidic precursors of wine flavor. J. Essent. Oil Res. 1994, 6, 587-599.
5. 13 glycoside from Vinca rosea. Phytochemistry 1974, 13, 2541-2543.
6. Bjorndal, H.; Hellerqvist, C. G.; Lindberg, B. Svenson, S. Gas -liquid chromatography and mass spectrometry in methylation analysis of polysaccharides. Angew. Chem., Int. Ed. Engl. 1970, 9, 610-619.
7. Chassagne, D.; Crouzet, J. Free and bound volatile components of temperate and tropical fruits. In Fruit Flavor, Biogenesis, Characterization and Authentication; Rouseff, R. L., Leahy, M. M., Eds.; American Chemical Society: Washington, DC, 1995; pp 182-189.
8. Chassagne, D.; Crouzet, J. Cyanogenic glycoside from Passiflora edulis fruits with an unusual sugar residue. Phytochemistry 1998, 43, in press.
9. Chassagne, D.; Bayonove, C.; Crouzet, J.; Baumes, R. L. Formation of aroma by enzymic hydrolysis of glycosidically bound components of passion fruit. In Bioflavour '95, Analysis, Precursors Studies, Biotechnology; Etievant, P., Schreier, P., Eds.; INRA: Paris, 1995a; pp 217-222.
10. Chassagne, D.; Crouzet, J.; Baumes, R. L.; Lepoutre, J.-P.; Bayonove, C. Determination of trifluoroacetylated glycosides by gas chromatography coupled to methane negative chemical ionization mass spectrometry. J. Chromatogr. A 1995b, 694, 441-451.
11. Chassagne, D.; Crouzet, J.; Bayonove, C. L.; Brillouet, J.-M.; Baumes, R. L.6-O-α-L-arabinopyranosyl-β-D-glucopyranosides as aroma precursors from passion fruit. Phytochemistry 1996a, 41, 1497-1500.
12. Chassagne, D.; Crouzet, J.; Bayonove, C. L.; Baumes, R. L. Identification and quantification of passion fruit cyanogenic glycosides. J. Agric. Food Chem. 1996b, 44, 3817-3820.
13. Chassagne, D.; Crouzet, J.; Bayonove, C. L.; Baumes, R. L. Glycosidically bound eugenol and methyl salicylate in the fruits of edible Passiflora species. J. Agric. Food Chem. 1997, 45, 2685-2689.
14. Engel K. H.; Tressl, R. Formation of aroma components from non volatile precursors in Passion fruit. J. Agric. Food Chem. 1983, 31, 998-1002.
15. Eyjolfsson, R. Recent advances in the chemistry of cyanogenic glycosides. Fortschr. Chem. Org. Naturst. 1970, 27, 74-108.
16. Gunata, Y. Z.; Bayonove, C.; Baumes R. L.; Cordonnier, R. The aroma of grapes: extraction and determination of free and glycosidically bound fractions of some grapes aroma components. J. Chromatogr. 1985, 331, 83-90.
17. Harris, P. J.; Henry, R. J.; Blakeney, A. B.; Stone, B. A. An improved procedure for the methylation analysis of oligosaccharides and polysaccharides. Carbohydr. Res. 1984, 127, 59-73.
18. Jansson, P. E.; Kenne, L.; Liedgren H.; Lindberg, B.; Lönngren, J. A practical guide to the methylation analysis of carbohydrates. Chem. Commun. Univ. Stockholm 1976, 8, 1-20.
19. Pabst, A.; Barron, D.; Semon E.; Schreier, P. Two diastereomeric 3-oxo-α-ionol β-D-glucosides from raspberry fruit. Phytochemistry 1992a, 31, 1649-1652.
20. Pabst, A.; Barron, D.; Semon E.; Schreier, P. 4-Oxo-β-ionol and linalool glycosides from raspberry fruits. Phytochemistry 1992b, 31, 4187-4190.
21. Salles, C.; Essaied, P.; Chalier, P.; Jallageas, J. C.; Crouzet, J. Evidence and characterization of glycosidically bound volatile components in fruits. In Bioflavour '87; Schreier, P., Ed.; de Gruyter: Berlin, 1988; pp 145-159.
22. Salles, C.; Jallageas, J. C.; Crouzet, J. Chromatographic separation and partial identification of glycosidically bound volatile components of fruits. J. Chromatogr. 1990, 522, 255-265.
23. Salles, C.; Jallageas, J. C.; Crouzet, J. HPLC separation of fruit diastereoisomeric monoterpenyl glycosides. J. Essent. Oil Res. 1993, 5, 381-390.
24. Saulnier, L.; Brillouet, J. M. Structural studies of pectic substances from the pulp of grape berries. Carbohydr. Res. 1987, 182, 63-78.
25. Skouroumounis, G. K.; Winterhalter, P. Glycosidically bound norisoprenoids from Vitis vinifera Cv. Riesling leaves. J. Agric. Food Chem. 1994, 42, 1068-1072.
26. Stahl-Biskup, E.; Intert, F. Holthuijzen, J.; Stengele, M. Glycosidically bound volatiles - A review 1986-1991. Flavour Fragrance J. 1993, 8, 61-80.
27. Strauss, C. R.; Wilson, B.; Williams, P. J. 3-Oxo-α-ionol, vomifoliol and roseoside in Vitis vinifera fruit. Phytochemistry 1987, 26, 1995-1997.
28. Sweeley, C. C.; Bentley, R.; Makita, M.; Wells, W. W. Gas -liquid chromatography of trimethylsilyl derivatives of sugars and related substances. J. Am. Chem. Soc. 1963, 85, 2497-2507.
29. Tschesche, R.; Ciper, F.; Harz, A. Roseosid aus Betula alba und Cydonia oblonga. Phytochemistry 1976,15, 1990-1991.
30. Van den Dool, H.; Kratz, P. D. A generalization of the retention time index system including linear temperature programmed gas - liquid partition chromatography. J. Chromatogr. 1963, 11, 463-471.
31. Voirin, S. G.; Baumes, R. L.; Bayonove, C. L.; M'Bairaroua, O.; Tapiero, C. Synthesis and NMR spectral properties of grape monoterpenyl glycosides. Carbohydr. Res. 1990, 207, 39-56.
32. Voirin, S. G.; Baumes, R. L.; Günata, Z. Y.; Bitteur, S. M.; Bayonove, C. L.; Tapiero, C. Analytical methods for monoterpene glycosides in grape and wine. I XAD-2 extraction and gas chromatographic-mass spectrometric determination of synthetic glycosides. J. Chromatogr. 1992, 590, 313-328.
33. Winterhalter, P. Bound terpenoids in the juice of the purple passion fruit. J. Agric. Food Chem. 1990, 38, 452-455.
34. Winterhalter, P.; Skouroumounis, G. Glycoconjugated aroma compounds: occurrence, role and biotechnological transformation. In Advances in Biochemical Engineering / Biotechnology, Special Vol. 55, Biotechnology; Berger, R. G., Ed.; Springer-Verlag: Berlin, 1997; pp 73-105.