Surface molecularly imprinted silica for selective solid-phase extraction of biochanin A, daidzein and genistein from urine samples

Journal of Chromatography A

Volumn 1392, Issue , 2015, Pages 1-9

  Chrzanowska, Anna M ^a   Poliwoda, Anna ^a   Wieczorek, Piotr P ^a  

^a UNIVERSITY OF OPOLE   (Poland)

Author keywords

Isoflavones; Molecularly imprinted polymer; Silica gel; Solid phase extraction; Urine

Indexed keywords

FLAVONOIDS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; NITROGEN COMPOUNDS; ORGANIC POLYMERS; PHASE SEPARATION; SCANNING ELECTRON MICROSCOPY; SILICA; SILICA GEL; SILICON; SOL-GEL PROCESS;

3-AMINOPROPYLTRIETHOXYSILANE; FOURIER TRANSFORM INFRARED SPECTROMETRY; ISOFLAVONES; MOLECULARLY IMPRINTED POLYMER; SELECTIVE SOLID-PHASE EXTRACTION; SOLID-PHASE EXTRACTION; SURFACE MOLECULAR IMPRINTING TECHNIQUES; URINE;

EXTRACTION;

3 AMINOPROPYLTRIETHOXYSILANE; BIOCHANIN A; DAIDZEIN; GENISTEIN; SILICON DIOXIDE; TETRAETHOXYSILICANE; UNCLASSIFIED DRUG; AMINO-PROPYL-TRIETHOXYSILANE; CROSS LINKING REAGENT; GAMMA-AMINOPROPYLTRIETHOXYSILANE; ISOFLAVONE DERIVATIVE; NANOPARTICLE; POLYMER; SILANE DERIVATIVE; SILICA GEL; TETRAETHOXYSILANE; WATER;

ADSORPTION KINETICS; ANALYTIC METHOD; ARTICLE; AUTOANALYZER; BARRET JOYNER HALENDA METHOD; BRUNAUER EMETT TELLER METHOD; CONTROLLED STUDY; CROSS LINKING; DATA ANALYSIS SOFTWARE; DRUG DETERMINATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROMETRY; INTERMETHOD COMPARISON; MASS SPECTROMETER; MOLECULAR IMPRINTING; PARTICLE SIZE; PRIORITY JOURNAL; SCANNING ELECTRON MICROSCOPE; SCANNING ELECTRON MICROSCOPY; SEPARATION TECHNIQUE; SOLID PHASE EXTRACTION; STANDARD; SURFACE PROPERTY; URINALYSIS; CHEMISTRY; FEMALE; HUMAN; POROSITY; PROCEDURES; URINE;

CROSS-LINKING REAGENTS; FEMALE; GENISTEIN; HUMANS; ISOFLAVONES; MOLECULAR IMPRINTING; NANOPARTICLES; POLYMERS; POROSITY; SILANES; SILICA GEL; SILICON DIOXIDE; SOLID PHASE EXTRACTION; WATER;

EID: 84926080755     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2015.03.015     Document Type: Article

References (51)

1. Vitale D.C., Piazza C., Melilli B., Drago F., Salomone S. Isoflavones: estrogenic activity, biological effect and bioavailability. Eur. J. Drug Metab. Pharmacokinet. 2013, 38:15-25.
2. Bingham S.A., Atkinson C., Liggins J., Bluck L., Coward A. Phyto-oestrogens: where are we now?. Br. J. Nutr. 1998, 79:393-406.
3. Patisaul H.B., Jefferson W. The pros and cons of phytoestrogens. Front. Neuroendocrinol. 2010, 31:400-419.
4. Fu S.W., Zeng G.F., Zong S.H., Zhang Z.Y., Zou B., Fang Y., Lu L., Xiao D.Q. Systematic review and meta-analysis of the bone protective effect of phytoestrogens on osteoporosis in ovariectomized rats. Nutr. Res. 2014, 34:467-477.
5. Bedell S., Nachtigall M., Naftolin F. The pros and cons of plant estrogens for menopause. J. Steroid Biochem. Mol. Biol. 2014, 139:225-236.
6. Gonzalez Canete N., Duran Aguero S. Soya isoflavones and evidences on cardiovascular protection. Nutr. Hosp. 2014, 29:1271-1282.
7. Ruiz-Larrea M.B., Mohan A.R., Paganga G., Miller N.J., Bolwell G.P., Rice-Evans C.A. Antioxidant activity of phytoestrogenic isoflavones. Free Radic. Res. 1997, 26:63-70.
8. Crain D.A., Janssen S.J., Edwards T.M., Heindel J., Ho S.M., Hunt P., Iguchi T., Juul A., McLachlan J.A., Schwartz J., Skakkebaek N., Soto A.M., Swan S., Walker C., Woodruff T.K., Woodruff T.J., Giudice L.C., Guillette L.J. Female reproductive disorders: the roles of endocrine-disrupting compounds and developmental timing. Fertil. Steril. 2008, 90:911-940.
9. Costa E.M., Spritzer P.M., Hohl A., Bachega T.A. Effects of endocrine disruptors in the development of the female reproductive tract. Arq. Bras. Endocrinol. Metabol. 2014, 58:153-161.
10. Franke A.A., Custer L.J., Tanaka Y. Isoflavones in human breast milk and other biological fluids. Am. J. Clin. Nutr. 1998, 68:1466S-1473S.
11. Franke A.A., Custer L.J., Wang W., Shi C.Y. HPLC analysis of isoflavonoids and other phenolic agents from foods and from human fluids. P. Soc. Exp. Biol. Med. 1998, 217:263-273.
12. Franke A.A., Custer L.J., Wilkens L.R., Le Marchand L., Nomura A.M.Y., Goodman M.T., Kolonel L.N. Liquid chromatographic-photodiode array mass spectrometric analysis of dietary phytoestrogens from human urine and blood. J. Chromatogr. B 2002, 777:45-59.
13. Zheng W., Dai Q., Custer L.J., Shu X.O., Wen W.Q., Jin F., Franke A.A. Urinary excretion of isoflavonoids and the risk of breast cancer. Cancer Epidem. Biomar. 1999, 8:35-40.
14. Maskarinec G., Singh S., Meng L., Franke A.A. Dietary soy intake and urinary isoflavone excretion among women from a multiethnic population. Cancer Epidem. Biomar. 1998, 7:613-619.
15. Wyns C., Bolca S., De Keukeleire D., Heyerick A. Development of a high-throughput LC/APCI-MS method for the determination of thirteen phytoestrogens including gut microbial metabolites in human urine and serum. J. Chromatogr. B 2010, 878:949-956.
16. Dabas P.C., Báncora P., Vescina M.C. Optimized separation conditions of soy isoflavonoids in urine by capillary zone electrophoresis. J. Capill. Electrophor. Microchip. Technol. 2003, 8:53-58.
17. Grace P.B., Mistry N.S., Carter M.H., Leathem A.J.C., Teale P. High throughput quantification of phytoestrogens in human urine and serum using liquid chromatography/tandem mass spectrometry (LC-MS/MS). J. Chromatogr. B 2007, 853:138-146.
18. Moors S., Blaszkewicz M., Bolt H.M., Degen G.H. Simultaneous determination of daidzein, equol, genistein and bisphenol A in human urine by a fast and simple method using SPE and GC-MS. Mol. Nutr. Food Res. 2007, 51:787-798.
19. Cao Y., Calafat A.M., Doerge D.R., Umbach D.M., Bernbaum J.C., Twaddle N.C., Ye X., Rogan W.J. Isoflavones in urine, saliva, and blood of infants: data from a pilot study on the estrogenic activity of soy formula. J. Expo. Sci. Env. Epid. 2009, 19:223-234.
20. Richelle M., Pridmore-Merten S., Bodenstab S., Enslen M., Offord E.A. Hydrolysis of isoflavone glycosides to aglycones by β-glycosidase does not alter plasma and urine isoflavone pharmacokinetics in postmenopausal women. J. Nutr. 2002, 132:2587-2592.
21. Schmidt S., Degen G.H., Seibel J., Hertrampf T., Vollmer G., Diel P. Hormonal activity of combinations of genistein, bisphenol A and 17β-estradiol in the female Wistar rat. Arch. Toxicol. 2006, 80:839-845.
22. Tekeł J., Daeseleire E., Heeremans A., Van Peteghem C. Development of a simple method for the determination of genistein, daidzein, biochanin A, and formononetin (Biochanin B) in human urine. J. Agr. Food Chem. 1999, 47:3489-3494.
23. Adlercreutz H., Kiuru P., Rasku S., Wähälä K., Fotsis T. An isotope dilution gas chromatographic-mass spectrometric method for the simultaneous assay of estrogens and phytoestrogens in urine. J. Steroid Biochem. 2004, 92:399-411.
24. Nurmi T., Voutilainen S., Nyyssönen K., Adlercreutz H., Salonen J.T. Liquid chromatography method for plant and mammalian lignans in human urine. J. Chromatogr. B 2003, 798:101-110.
25. Vasapollo G., Sole R.D., Mergola L., Lazzoi M.R., Scardino A., Scorrano S., Mele G. Molecularly imprinted polymers: present and future prospective. Int. J. Mol. Sci. 2011, 12:5908-5945.
26. Mayes A.G., Mosbach K. Molecularly imprinted polymers: useful materials for analytical chemistry?. Trac-Trends Anal. Chem. 1997, 16:321-332.
27. Tarbin J.A., Sharman M. Development of molecularly imprinted phase for the selective retention of stilbene-type estrogenic compounds. Anal. Chim. Acta 2001, 433:71-79.
28. Weiss R., Molinelli A., Jakusch M., Mizaikoff B. Molecular imprinting and solid phase extraction of flavonoid compounds. Bioseparation 2001, 10:379-387.
29. Pakade V., Lindahl S., Chimuka L., Turner C. Molecularly imprinted polymers targeting quercetin in high-temperature aqueous solutions. J. Chromatogr. A 2012, 1230:15-23.
30. Schwarz L.J., Danylec B., Harris S.J., Boysen R.I., Hearn M.T. Preparation of molecularly imprinted polymers for the selective recognition of the bioactive polyphenol, (E)-resveratrol. J. Chromatogr. A 2011, 1218:2189-2195.
31. Luo J., Zhang L., Chen D., Wang P., Zhao J., Peng Y., Du S., Zhang Z. Molecularly imprinted layer-coated monodisperse spherical silica microparticles toward affinity-enrichment of isoflavonoid glycosides from Radix puerariae. Analyst 2012, 137:2891-2902.
32. Cheng W., Liu Z., Wang Y. Preparation and application of surface molecularly imprinted silica gel for selective extraction of melamine from milk samples. Talanta 2013, 116:396-402.
33. Sun X.L., Tian X.M., Zhang Y.Z., Tang Y.J. Molecularly imprinted layer-coated silica gel particles for selective solid-phase extraction of pefloxacin and enrofloxacin from milk samples. Food Anal. Met. 2013, 6:1361-1369.
34. Zhang Y., Gao B., An F., Xu Z., Zhang T. Adsorption and recognition characteristics of surface molecularly imprinted polymethacrylic acid/silica toward genistein. J. Chromatogr. A 2014, 1359:26-34.
35. Gao B.J., Zhang Y.Y., Chen T. Designing and preparing of quercetin surface-imprinted material and its molecular recognition characteristics. J. Appl. Polym. Sci. 2014, 131.
36. Xu Z., Chen S., Huang W., Fang G., Pingzhu H., Wang S. Study on an on-line molecularly imprinted solid-phase extraction coupled to high-performance liquid chromatography for separation and determination of trace estrone in environment. Anal. Bioanal. Chem. 2009, 393:1273-1279.
37. Jiang X., Tian W., Zhao C., Zhang H., Liu M. A novel sol-gel-material prepared by a surface imprinting technique for the selective solid-phase extraction of bisphenol A. Talanta 2007, 72:119-125.
38. Zhu R., Zhao W., Zhai M., Wei F., Cai Z., Sheng N., Hu Q. Molecularly imprinted layer-coated silica nanoparticles for selective solid-phase extraction of bisphenol A from chemical cleansing and cosmetics samples. Anal. Chim. Acta 2010, 658:209-216.
39. Stöber W., Fink A., Bohn E. Controlled growth of monodisperse silica spheres in the micron size range. J. Colloid Interf. Sci. 1968, 26:62-69.
40. Jiang N., Chang X., Zheng H., He Q., Hu Z. Selective solid-phase extraction of nickel(II) using a surface-imprinted silica gel sorbent. Anal. Chim. Acta 2006, 577:225-231.
41. Stintzing F.C., Hoffmann M., Carle R. Thermal degradation kinetics of isoflavone aglycones from soy and red clover. Mol. Nutr. Food Res. 2006, 50:373-377.
42. Grün I.U., Adhikari K., Li C., Li Y., Lin B., Zhang J., Fernando L.N. Changes in the profile of genistein, daidzein, and their conjugates during thermal processing of tofu†. J. Agr. Food Chem. 2001, 49:2839-2843.
43. Ungar Y., Osundahunsi O.F., Shimoni E. Thermal stability of genistein and daidzein and its effect on their antioxidant activity. J. Agr. Food Chem. 2003, 51:4394-4399.
44. Maier N., Lindner W. Chiral recognition applications of molecularly imprinted polymers: a critical review. Anal. Bioanal. Chem. 2007, 389:377-397.
45. Maier N.M., Buttinger G., Welhartizki S., Gavioli E., Lindner W. Molecularly imprinted polymer-assisted sample clean-up of ochratoxin A from red wine: merits and limitations. J. Chromatogr. B 2004, 804:103-111.
46. Schmidt L., Muller J., Goen T. Simultaneous monitoring of seven phenolic metabolites of endocrine disrupting compounds (EDC) in human urine using gas chromatography with tandem mass spectrometry. Anal. Bioanal. Chem. 2013, 405:2019-2029.
47. Baranowska I., Magiera S. Analysis of isoflavones and flavonoids in human urine by UHPLC. Anal. Bioanal. Chem. 2011, 399:3211-3219.
48. Tsunoda N., Pomeroy S., Nestel P. Absorption in humans of isoflavones from soy and red clover is similar. J. Nutr. 2002, 132:2199-2201.
49. Baranowska I., Magiera S., Baranowski J. UHPLC method for the simultaneous determination of β-blockers, isoflavones, and flavonoids in human urine. J. Chromatogr. Sci. 2011, 49:764-773.
50. Schmidt L., Müller J., Göen T. Simultaneous monitoring of seven phenolic metabolites of endocrine disrupting compounds (EDC) in human urine using gas chromatography with tandem mass spectrometry. Anal. Bioanal. Chem. 2013, 405:2019-2029.
51. Rybak M.E., Parker D.L., Pfeiffer C.M. Determination of urinary phytoestrogens by HPLC-MS/MS: a comparison of atmospheric pressure chemical ionization (APCI) and electrospray ionization (ESI). J. Chromatogr. B 2008, 861:145-150.