Molecular imprinting and solid phase extraction of flavonoid compounds

Molecularly imprinted polymers (MIPs) for quercetin have been successfully prepared by a thermal polymerization method using 4-vinylpyridine (4-VP) and ethylene glycol dimethacrylate (EDMA) as functional monomer and cross-linker, respectively. The obtained molecularly imprinted polymers were evaluated by HPLC using organic eluents, with respect to their selective recognition properties for quercetin and related compounds of the flavonoid class. Two equivalent control polymers, a blank polymer and a polymer imprinted with a structural analogous template, were synthesized, in order to confirm the obtained results. Furthermore, preliminary experiments confirm the applicability of the prepared MIPs for solid phase extraction (SPE), as rapid and facile clean-up of wine samples for HPLC analysis is an envisaged field of application. The successful preparation of molecularly imprinted polymers for flavones provides an innovative opportunity for the development of advanced separation materials, with applications in the field of wine and fermentation analysis.

[1]  L. Fischer,et al.  Chiral separation using molecularly imprinted heteroaromatic polymers , 1993, Journal of molecular recognition : JMR.

[2]  G. Wulff,et al.  Template Imprinted Polymers for HPLC Separation of Racemates , 1990 .

[3]  J. Oszmiański,et al.  Fractionation of Phenolic Compounds in Red Wine , 1988, American Journal of Enology and Viticulture.

[4]  A. Waterhouse,et al.  A Direct HPLC Separation of Wine Phenolics , 1994, American Journal of Enology and Viticulture.

[5]  M. Bourzeix,et al.  Separation and quantitative determination of grape and wine procyanidins by high performance reversed phase liquid chromatography , 1990 .

[6]  W. Meylan,et al.  Atom/fragment contribution method for estimating octanol-water partition coefficients. , 1995, Journal of pharmaceutical sciences.

[7]  L. Andersson,et al.  Molecular imprinting for drug bioanalysis. A review on the application of imprinted polymers to solid-phase extraction and binding assay. , 2000, Journal of chromatography. B, Biomedical sciences and applications.

[8]  D. Stevenson Molecular imprinted polymers for solid-phase extraction , 1999 .

[9]  T. Watkins Wine: Nutritional and Therapeutic Benefits , 1997 .

[10]  D M Goldberg,et al.  Method to assay the concentrations of phenolic constituents of biological interest in wines. , 1996, Analytical chemistry.

[11]  Robert Weiss,et al.  Molecularly Imprinted Polymers for Nitrophenols - An Advanced Separation Material for Environmental Analysis , 2001 .

[12]  A. J. Ryan,et al.  Analysis of several phenolic compounds with potential antioxidant properties in grape extracts and wines by high-performance liquid chromatography-photodiode array detection without sample preparation. , 2000, Journal of chromatography. A.

[13]  A. Jaworski,et al.  Fractionation and HPLC determination of grape phenolics , 1987 .

[14]  P. Ribereau-gayon,et al.  Handbook of Enology , 2001 .

[15]  N. Russo,et al.  Semiempirical molecular modeling into quercetin reactive site: structural, conformational, and electronic features. , 2000, Journal of agricultural and food chemistry.

[16]  K Mosbach,et al.  Assay system for the herbicide 2,4-dichlorophenoxyacetic Acid using a molecularly imprinted polymer as an artificial recognition element. , 1998, Analytical chemistry.

[17]  E. Diamandis,et al.  A multiresidue derivatization gas chromatographic assay for fifteen phenolic constituents with mass selective detection. , 1997, Analytical chemistry.

[18]  A. Bertrand,et al.  Wine phenolics—analysis of low molecular weight components by high performance liquid chromatography , 1984 .

[19]  L. Andersson,et al.  Efficient sample pre-concentration of bupivacaine from human plasma by solid-phase extraction on molecularly imprinted polymers. , 2000, The Analyst.