Separation of flavanone-7-O-glycoside diastereomers and analysis in citrus juices by multidimensional liquid chromatography coupled with mass spectrometry

Journal of Agricultural and Food Chemistry

Volumn 52, Issue 17, 2004, Pages 5303-5308

  Aturki, Zeineb ^a   Brandi, Valentina ^a   Sinibaldi, Massimo ^a  

^a CNR   (Italy)

Author keywords

Citrus fruit juices; Diastereomer separation; ESI MS detection; Flavanone 7 O glycosides; Multidimensional liquid chromatography

Indexed keywords

AURANTIIN; BETA CYCLODEXTRIN; ERIOCITRIN; FLAVANONE 7 O GLYCOSIDE; FLAVANONE DERIVATIVE; GLYCOSIDE; HESPERIDIN; NARIRUTIN; NEOHESPERIDIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CITRUS FRUIT; DIASTEREOISOMER; ELECTROSPRAY MASS SPECTROMETRY; FOOD ANALYSIS; FOOD PROCESSING; FRUIT JUICE; GRAPEFRUIT JUICE; LEMON JUICE; LIQUID CHROMATOGRAPHY; ORANGE JUICE; QUANTITATIVE ANALYSIS; SEPARATION TECHNIQUE; STEREOISOMERISM; VALIDATION PROCESS;

BEVERAGES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CITRUS; FLAVANONES; FRUIT; GLYCOSIDES; MASS SPECTROMETRY; STEREOISOMERISM;

CITRUS; CITRUS LIMON; CITRUS X PARADISI;

EID: 4143092714     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0400967     Document Type: Article

References (29)

1. Harborne, J. B.; Mabry, T. J.; Mabry, H. The Flavonoids; Chapman and Hall: London, U.K., 1975.
2. Bouskela, E.; Cyrino, F. Z.; Lerond, L. Effect of oral administration of different doses of purified micronized flavonoid fraction on microvascular reactivity after ischemia/reperfusion in the hamster cheek pouch. Br. J. Pharmacol. 1997, 122, 1611-1616.
3. Tanaka, T.; Makita, H.; Kawabata, K.; Mori, H.; Kakumoto, M.; Satoh, A.; Hara, T.; Sumida, T.; Tanaka, T.; Ogawa, H. Chemoprevention of azoxymethane-induced rat colon carcinogenesis by naturally occurring flavonoids, diosmin and hesperidin. Carcinogenesis 1997, 18, 957-965.
4. Kawai, S.; Tomono, Y.; Katase, E.; Ogawa, K.; Yano, M. Quantitation of flavonoid constituents in Citrus fruits. J. Agric. Food Chem. 1999, 47, 3565-3571.
5. Mouly, P. P.; Arzouyan, C. R.; Gaydou, E. M.; Estienne, J. M. Differentiation of Citrus juices by factorial discriminant analysis using liquid chromatography of flavanone glycosides. J. Agric. Food Chem. 1994, 42, 70-79.
6. Ooghe, W. C.; Ooghe, S. J.; Detavernier, C. M.; Huyghebaert, A. Characterization of orange juice (Citrus sinensis) by flavanone glycosides. J. Agric. Food Chem. 1994, 42, 2183-2190.
7. Rouseff, R. L.; Martin, S. F.; Youtsey, C. O. Quantitative survey of narirutin, naringin, hesperidin and neohesperidin in Citrus. J. Agric. Food Chem. 1987, 35, 1027-1030.
8. Mouly, P.; Gaydou, E. M., Estienne, J. M. Column liquid chromatographic determination of flavanone glycosides in Citrus. Application to grapefruit and sour orange juice adulterations. J. Chromatogr. 1993, 634, 129-134.
9. Widmer, W. Determination of naringin and neohesperidin in orange juices by liquid chromatography with UV detection to detect the presence of grapefruit juice: collaborative study. J. AOAC Int. 2000, 83, 1155-1165.
10. Gaffield, W. Circular dichroism, optical rotatory dispersion and absolute configuration of flavanones, 3-hydroxyflavanones and their glycosides. Determination of aglycone chirality in flavanone glycosides. Tetrahedron 1970, 26, 4093-4108.
11. Gaffield, W.; Lundin, R. E.; Gentili, B.; Horowitz, R. M. C-2 stereochemistry of naringin and its relation to taste and biosynthesis in maturing grapefruit. Bioorg. Chem. 1975, 4, 259-269.
12. Krause, M.; Galensa, R. Improved chiral stationary phase based on cellulose triacetate supported on non-macroporous silica gel diol for the high-performance liquid chromatographic separation of racemic flavanones and diastereomeric flavavone glycosides. J. Chromatogr. 1990, 502, 287-296.
13. Krause, M.; Galensa, R. High performance liquid chromatography of diastereoisomeric flavanone glycosides in Citrus on a β-cyclodextrin-bonded phase stationary phase (Cyclobond I). J. Chromatogr. 1991, 588, 41-45.
14. Gel-Moreto, N.; Streich, R.; Galensa, R. Chiral separation of diastereomeric flavanone-7-O-glycosides in citrus by capillary electrophoresis. Electrophoresis 2003, 24, 2716-2722.
15. Aturki, Z.; Sinibaldi, M. Separation of diastereomers of flavanone-7-O-glycosides by capillary electrophoresis using sulfobutyl ether-β-cyclodextrin as the selector. J. Sep. Sci. 2003, 26, 844-850.
16. Riley, C. M., Lough, W. J., Wainer, I. W., Eds. Pharmaceutical and Biomedical Applications of Liquid Chromatography; Pergamon: Oxford, U.K., 1994; pp 241-257 and references cited therein.
17. Chen, H.; Zuo, Y.; Deng, Y. Separation and determination of flavonoids and other phenolic compounds in cranberry juice by high-performance liquid chromatography. J. Chromatogr. A 2001, 913, 387-395.
18. Robards, K.; Antolovich, M. Analytical chemistry of fruit bioflavonoids. A review. Analyst 1997, 122, 11R-34R.
19. Merken, H. M.; Beecher, G. R. Measurements of food flavanoids by high-performance liquid chromatography. A review. J. Agric. Food Chem. 2001, 48, 576-599.
20. Escarpa, A.; Gonzalez, M. C. An overview of analytical chemistry of phenolic compounds in foods. Crit. Rev. Anal. Chem. 2001, 31, 57-139.
21. Gamache, P.; Ryan, E.; Acworth, I. N. Analysis of phenolic and flavonoid compounds in juice beverages using high-performance liquid chromatography with coulometric array detection. J. Chromatogr. 1993, 635, 143-150.
22. Careri, M.; Elviri, L.; Mangia, A. Validation of a liquid chromatography ion spray mass spectrometry method for the analysis of flavanones, flavones and flavonols. Rapid Commun. Mass Spectrom. 1999, 13, 2399-2405.
23. Fisher, J. F.; Wheaton, Fisher, J. F.; Wheaton, T. A. A high-pressure liquid chromatographic method for the resolution and quantitation of naringin and naringenin rutinoside in grapefruit juice. J. Agric. Food Chem. 1976, 24, 898-899.
24. Hagen, R. E.; Dunlap, W. J.; Mizelle, J. W.; Wender, S. H.; Lime, B. J.; Albach, R. F.; Griffiths, F. P. A chromatographic-fluorimetric method for determination of naringin, naringenin rutinoside and related flavanone glycosides on grapefruit juices. Anal. Biochem. 1965, 12, 472-482.
25. Mansell, R. L.; McIntosh, C. A.; Vest, S. E. An analysis of the limonin and naringin content of grapefruit juice samples collected from Florida state test houses. J. Agric. Food Chem. 1983, 31, 156-162.
26. Albach, R. F.; Redman, G. H.; Cruse, R. R. Annual and seasonal changes in naringin concentration of ruby red grapefruit juice. J. Agric. Food Chem. 1981, 29, 808-811.
27. Rouseff, R. L. Differentiating citrus juices using flavanone glycoside concentration profiles. In Adulteration of Fruit Juice Beverages; Nagy, S., Attaway, J. A., Rhodes, M. E., Eds.; Dekker: New York, 1988; Chapter 3.
28. Rouseff, R. L. Liquid chromatographic determination of naringin and neohesperidin as a detector of grapefruit juice in orange juice. J. Assoc. Off. Anal. Chem. 1988, 71, 798-802.
29. Dunlap, W. J.; Wender, S. H. Identification studies on some minor flavonoid constituents of grapefruit. Anal. Biochem. 1962, 4, 110-115.