Flavanones chromatography

JUSTESEN u, KNUTHSEN p and LETH T (1998) Quantitative analysis of flavonols, flavones, and flavanones in fruits, vegetables and beverages by high-performance liquid chromatography with photo-diode array and mass specfrometric detection, /C/u matogr A, 799, 101-10. 

Various analytical methods exist for flavonoids. These range from TLC to CE. With the introduction of hyphenated HPLC techniques, the analytical potential has been dramatically extended. Gas chromatography (GC) is generally impractical, due to the low volatility of many flavonoid compounds and the necessity of preparing derivatives. However, Schmidt et al. ° have reported the separation of flavones, flavonols, flavanones, and chalcones (with frequent substitution by methyl groups) by GC. 

Fabre, N. et al.. Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry, J. Am. Soc. Mass Spectrom., 12, 707, 2001. 

Mouly, P.P. et ak, Differentiation of citrus juices by factorial discriminant analysis using liquid chromatography of flavanone glycosides, J. Agric. Food Chem., 42, 70, 1994. 

P Mouly, EM Gaydou, A Auffray. Simultaneous separation of flavanone glycosides and polymeth-oxylated flavones in citrus juices using liquid chromatography. J Chromatogr 800 171-179, 1998. 

Gas-liquid chromatography (GLC) has notTeen employed for the analysis of flavanone glycosides because they are non-volatile and thermally unstable. One GLC method (28) has been developed for the analysis of the flavanone aglycones. However, the method is extremely time consuming in that the samples must be extracted, hydrolyzed and derivatized before analysis. Furthermore, the procedure cannot distinguish between bitter and nonbitter flavonoids. 

Koupai-Abyzani, M.R. Creaser, C.S. Stephenson, G.R. 1992. Separation and identification of flavone, flavanol, isoflavone, and flavanone aglycones by capillary column gas chromatography. Phytochem. Anal. 3 380-384. 

In the present chapter, various tools such as thin-layer chromatography, high performance liquid chromatography, mass spectroscopy, and NMR used in analysis of flavonoids are discussed. In addition, the relevance and application of such tools in the analysis of flavanones, with emphasis on citrus flavanones, is discussed. 

In recent years capillary electro separations were found to be useful for the analysis of a variety of small molecules. Several variants of the basic technique- such as capillary zone electrophoresis, micellar electroki-netic chromatography, and capillary gel electrophoresis - are available. However, only a handful of reports are available on flavanone analysis (Cancalon and Bryan, 1993 Desiderio et ah, 2005). Typically the separations were performed on silica fused capillaries of 70-75 pm internal diameter packed with RPig or uncoated silica (Cancalon and Bryan, 1993 Desiderio et ah, 2005). One of the major strengths of the techniques is the separation of multiclasses of compounds, ranging from amino acids to carotenoids to flavonoids (Cancalon and Bryan, 1993). 

Careri, M. Elviri, L. Mangia, A. 1999. Validation of a liquid chromatography ionspray mass spectrometry method for the analysis of flavanones, flavones and flavonols. Rapid Commun. Mass Spectrom. 13 2399-2405. 

Schmidtlein, H. Herrmann, K. 1976. Quantitative analysis of flavanones and 3-hydroxyflavanones by thin-layer chromatography. J. Chromatogr. A 123 385-390. 

Luco, J.M., Yamin, L.J. and Ferretti, H.F. (1995). Molecular Topology and Quantum Chemical Descriptors in the Study of Reversed-Phase Liquid Chromatography. Hydrogen-Bonding Behavior of Chalcones and Flavanones. J.Pharm.ScL, 84, 903-908. 

Pellati F, Benvenuti S, Melegari M. High-performance liquid chromatography methods for the analysis of adrenergic amines and flavanones in Citrus aurantium L. var. amara. Phytochem Anal 2004 15 220-225. 

The mixture of compounds contained in the crude extract were separated by chromatography on silica gel using various organic solvents. This process led to the isolation of three chalcones, 11 prenylated flavanones, three pterocarpanoids and one isoflav-3-ene (Figure 3). While the details of the characterization of these compounds have been reported elsewhere, it is worth pointing out that in the bioassay assessment referred to above, they had reasonable LC50 values (Table 4). They had antimalarial activities comparable to those of the crude extracts and should be the principles responsible for the activity. 

Wang, S. R, Fu, M. D., and Wang, M. H. Separation mechanism and determination of flavanones with capillary electrophoresis and high-performance liquid chromatography, J. Chromatogr. A, 1164, 306, 2007. 

M. Krause and R. Galensa, High-performance Liquid Chromatography of Diastereometric Flavanone Glycosides in Citrus on a 13-cyclodextrin-bonded Stationary Phase (CYCLOBOND I), J. Chromatogr., 588(1991)41. 

Krause M, Galensa R (1991) High-performance liquid chromatography of diastereomeric flavanone glycosides in Citrus on a beta-cyclodextrin-bonded stationary phase (Cyclobond I). J Chromatogr 588 41-45... 

Bartolome (1994) reported polyamide TLC separation of flavanones from traces of other types of flavonoid compounds with crystallization of the flavonoid compounds before and after chromatography. Ficarra et al. (1994) determined the hydrophobic parameters of flavonoids by reversed-phase TLC. Nikolova-Da-myanova et al. (1994) used TLC to quantify iridoid and flavonoid glucosides in species of Linaria. 

---