A high-throughput UPLC-MS/MS for the simultaneous analysis of six phytoestrogens from genista tinctoria extracts

Journal of Liquid Chromatography and Related Technologies

Volumn 35, Issue 19, 2012, Pages 2735-2752

  Kiss, Béla ^a   Popa, Daniela Saveta ^a   Paltinean, Ramona ^a   Loghin, Felicia ^a  

^a IULIU HATIEGANU UNIVERSITY OF MEDICINE AND PHARMACY   (Romania)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE COMPOUNDS; ANALYTES; CHROMATOGRAPHIC SEPARATIONS; COUMESTROL; DAIDZEIN; DAIDZIN; ESI-MS/MS; FORMONONETIN; GENISTA TINCTORIA; GENISTEIN; GENISTIN; GRADIENT ELUTION; HIGH-THROUGHPUT; MOBILE PHASE; MULTIPLE-REACTION MONITORING MODES; PHYTOESTROGENES; PHYTOESTROGENS; RUNTIMES; SIMULTANEOUS ANALYSIS; SOLVENT CONSUMPTION; TARGET COMPOUND; THERAPEUTIC POTENTIALS; UPLC-MS/MS;

LIQUID CHROMATOGRAPHY; PLANT EXTRACTS;

FLAVONOIDS;

ACETIC ACID; AGLYCONE; COUMESTROL; DAIDZEIN; DAIDZIN; FORMONONETIN; GENISTA EXTRACT; GENISTA TINCTORIA EXTRACT; GENISTEIN; GENISTIN; METHANOL; PHYTOESTROGEN; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOGRAPHY; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; GENISTA; HIGH THROUGHPUT SCREENING; MASS SPECTROMETRY; SENSITIVITY ANALYSIS; SIGNAL NOISE RATIO; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

FLOS; GENISTA TINCTORIA;

EID: 84870860859     PISSN: 10826076     EISSN: 1520572X     Source Type: Journal    
DOI: 10.1080/10826076.2011.638410     Document Type: Article

References (73)

1. Murkies, A. L.; Wilcox, G.; Davis, S. R. Phytoestrogens. J. Clin. Endocrinol. Metab. 1998, 83 (2), 297-303
2. Duncan, A. M.; Phipps, W. R.; Kurzer, M. S. Phyto-oestrogens. Best Pract. Res. Cl. En. 2003, 17 (2), 253-271
3. Choi, S. Y.; Ha, T. Y.; Ahn, J. Y.; Kim, S. R.; Kang, K. S.; Hwang, I. K.; Kim, S. Estrogenic Activities of Isoflavones and Flavones and Their Structure-Activity Relationships. Planta Med. 2008, 74 (1), 25-32
4. Valls, J.; Millan, M. P.; Marti, M. P.; Borras, E.; Arola, L. Advanced Separation Methods of Food Anthocyanins, Isoflavones and Flavanols. J. Chromatogr. A 2009, 1216, 7143-7172
5. Beck, V., Rohr, U.; Jungbauer, A. Phytoestrogens Derived from Red Clover: An Alternative to Estrogen Replacement Therapy? J. Steroid. Biochem. Mol. Biol. 2005, 94 (5), 499-518
6. Rice, S.; Whitehead, S. A. Phytoestrogens Oestrogen Synthesis and Breast Cancer. J. Steroid. Biochem. 2008, 108, 186-195
7. 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
8. Adlercreutz, H. Phyto-oestrogens and Cancer. Lancet 2002, 3, 364-373
9. Occhiuto, F.; De Pasquale, R.; Guglielmo, G.; Palumbo, D. R.; Zangla, G.; Samperi, S.; Renzo, A.; Circosta, C. Effects of Phytoestrogenic Isoflavones from Red Clover (Trifolium pratense L.) on Experimental Osteoporosis. Phytother. Res. 2007, 21, 130-134
10. Atkinson, C.; Compston, J. E.; Day, N. E.; Dowsett, M.; Bingham, S. A. The Effects of Phytoestrogen Isoflavones on Bone Density in Women: A Double-Blind, Randomized, Placebo-Controlled Trial. Amer. J. Clin. Nutr. 2004, 79, 326-333
11. Velentzis, L. S.; Woodside, J. V.; Cantwell, M. M.; Leathem, A. J.; Keshtgar, M. R. Do Phytoestrogens Reduce the Risk of Breast Cancer and Breast Cancer Recurrence? What Clinicians Need to Know. Eur. J. Cancer 2008, 44, 1799-1806
12. Vinall, R. L.; Hwa, K.; Ghosh, P.; Pan, C. X.; Lara, P. N.; de Vere White, R. W. Combination Treatment of Prostate Cancer Cell Lines with Bioactive Soy Isoflavones and Perifosine Causes Increased Growth Arrest and=or Apoptosis. Clin. Cancer Res. 2007, 13, 6204-6216
13. Yu, Z.; Li, W.; Liu, F. Inhibition of Proliferation and Induction of Apoptosis by Genistein in Colon Cancer HT-29 Cells. Cancer Lett. 2004, 215, 159-166
14. Wenzel, U.; Fuchs, D.; Daniel, H. Protective Effects of Soy-Isoflavones in Cardiovascular Disease. Identification of Molecular Targets. Hamostaseologie 2008, 28, 85-88
15. Cassidy, A.; Albertazzi, P.; Nielsen, I. L.; Hall, W.; Williamson, G.; Tetens, I.; Atkins, S.; Cross, H.; Manios, Y.; Wolk, A.; Steiner, C.; Branca, F. Critical Review of Health Effects of Soybean Phyto-oestrogens in Post-menopausal Women. Proc. Nutr. Soc. 2006, 65, 76-92
16. Clifton-Bligh, P. B.; Baber, R. J.; Fulcher, G. R.; Nery, M. L.; Moreton, T. The Effect of Isoflavones Extracted from Red Clover (Rimostil) on Lipid and Bone Metabolism. Menopause 2001, 8, 259-265
17. Cancellieri, F.; De Leo, V.; Genazzani, A. D.; Nappi, C.; Parenti, G. L.; Polatti, F.; Ragni, N.; Savoca, S.; Teglio, L.; Finelli, F.; Nichelatti, M. Efficacy on Menopausal Neurovegetative Symptoms and Some Plasma Lipids Blood Levels of an Herbal Product Containing Isoflavones and Other Plant Extracts. Maturitas 2007, 56 (3), 249-256
18. Albertazzi, P.; Purdie, D. W. The Nature and Utility of the Phytoestrogens: A Review of the Evidence. Maturitas 2002, 42 (3), 173-185
19. Stopper, H.; Scmitt, E.; Kobras, K. Genotoxicity of Phytoestrogens. Mutat. Res. 2005, 574, 139-155
20. Rostagno, M. A.; Villares, A.; Guillamon, E.; Garcia-Lafuente, A.; Martinez, J. A. Sample Preparation for the Analysis of Isoflavones from Soybeans and Soy Foods. J. Chromatogr. A 2009, 1216, 2-29
21. Adlercreutz, H. Western Diet and Western Diseases: Some Hormonal and Biochemical Mechanisms and Associations. Scand. J. Clin. Lab. Invest. 1990, 50 (S201), 3-23
22. Markiewicz, L.; Garey, J.; Adlercreutz, H.; Gurpide, E. In Vitro Bioassays of Non-Steroidal Phytoestrogens. J. Steroid Biochem. Mol. Biol. 1993, 45 (5), 399-405
23. Kuhnle, G. G. C.; Dell'Aquila, C.; Aspinall, S. M.; Runswick, S. A.; Joosen, A. M. C. P.; Mulligan, A. A.; Bingham, S. A. Phytoestrogen Content of Fruits and Vegetables Commonly Consumed in the UK based on LC-MS and 13C-labelled Standards. Food Chem. 2009, 116, 542-554
24. Antonelli, M. L.; Faberi, A.; Pastorini, E.; Samperi, R.; Lagana, A. Simultaneous Quantitation of Free and Conjugated Phytoestrogens in Leguminosae By Liquid Chromatography-Tandem Mass Spectrometry. Talanta 2005, 66, 1025-1033
25. Tosun, F.; Erdem, C. K.; Eroǧlu, Y. Determination of Genistein in the Turkish Genista L. Species by LC-MS. Pharmazie 2003, 58 (8), 549-550
26. Luczkiewicz, M.; Piotrowski, A. Two-stage System for Micropropagation of Several Genista Plants Producing Large Amounts of Phytoestrogens. Z. Naturforsch C. 2005, 60 (7-8), 557-566
27. Booth, N. L.; Overk, C. R.; Yao, P.; Burdette, J. E.; Nikolic, D.; Chen, S. N.; Bolton, J. L.; van Breemen, R. B.; Pauli, G. F.; Farnsworth, N. R. The Chemical and Biological Profile of a Red Clover (Trifolium Pretense) Phase II Clinical Extract. J. Altern. Complement. Med. 2006, 12 (2), 133-139
28. Kiss, B.; Popa, D.-S.; Hanganu, D.; Pop, A.; Loghin, F. Ultra-performance Liquid Chromatography Method for the Quantification of Some Phytoestrogens in Plant Material. Rev. Roum. Chim. 2010, 55 (8), 459-465
29. Wang, S. W. J.; Chen, Y.; Joseph, T.; Hu, M. Variable Isoflavone Content of Red Clover Products Affects Intestinal Disposition of Biochanin A, Formononetin, Genistein, and Daidzein. J. Altern. Complement. Med. 2008, 14 (3), 287-297
30. Zgorka, G. Pressurized Liquid Extraction versus Other Extraction Techniques in Micropreparative Isolation of Pharmacologically Active Isoflavones from Trifolium L. species. Talanta 2009, 79 (1), 46-53
31. Zgorka, G. Ultrasound-assisted Solid-Phase Extraction Coupled with Photodiode-Array and Fluorescence Detection for Chemotaxonomy of Isoflavone Phytoestrogens in Trifolium L. (Clover) Species. J. Sep. Sci. 2009, 32, 965-972
32. Rigano, D.; Cardile, V.; Formisano, C.; Maldini, M. T.; Piacente, S.; Bevelacqua, Y.; Russo, A.; Senatore, F. Genista Sessilifolia DC and Genista tinctoria L. Inhibit UV Light and Nitric Oxide-induced DNA Damage and Human Melanoma Cell Growth. Chem. Biol. Interact. 2009, 180 (2), 211-219
33. Rostagno, M. A.; Palma, M.; Barroso, C. G. Ultrasound-Assisted Extraction of Soy Isoflavones. J. Chromatogr. A 2003, 1012 (2), 119-128
34. Rostagno, M. A.; Palma, M.; Barroso, C. G. Pressurized Liquid Extraction of Isoflavones from Soybeans. Anal. Chim. Acta 2004, 522, 169-177
35. Apers, S.; Naessens, T.; van den Steen, K.; Cuyckens, F.; Claeys, M.; Pieters, L.; Vlietinck, A. Fast High-Performance Liquid Chromatography Method for Quality Control of Soy Extracts. J. Chromatogr. A 2004, 1038, 107-112
36. Rostagno, M. A.; Palma, M.; Barroso, C. G. Solid-Phase Extraction of Soy Isoflavones. J. Chromatogr. A 2005, 1076, 110-117
37. Rostagno, M. A.; Araujo, J. M. A.; Sandi, D. Supercritical Fluid Extraction of Isoflavones from Soybean Flour. Food Chem. 2002, 78 (1), 111-117
38. Rostagno, M. A.; Palma, M.; Barroso, C. G. Ultrasound-Assisted Extraction of Isoflavones from Soy Beverages Blended with Fruit Juices. Anal. Chim. Acta 2007, 597, 265-272
39. Rostagno, M. A.; Palma, M.; Barroso, C. G. Microwave Assisted Extraction of Soy Isoflavones. Anal. Chim. Acta 2007, 588, 274-282
40. Rostagno, M. A.; Palma, M.; Barroso, C. G. Fast Analysis of Soy Isoflavones by High-Performance Liquid Chromatography with Monolithic Columns. Anal. Chim. Acta 2007, 582, 243-249
41. Peng, Y.; Chu, Q.; Liu, F.; Ye, J. Determination of Isoflavones in Soy Products by Capillary Electrophoresis with Electrochemical Detection. Food Chem. 2004, 87, 135-139
42. Peng, Y. Y.; Ye, J. N. Determination of Isoflavones in Red Clover by Capillary Electrophoresis with Electrochemical Detection. Fitoterapia 2006, 77, 171-178
43. Klejdus, B.; Mikelova, R.; Petrlova, J.; Potesil, D.; Adam, V.; Stiborová, M.; Hodek, P.; Vacek, J.; Kizek, R.; Kuba'n, V. Determination of Isoflavones in Soy Bits by Fast Column High-Performance Liquid Chromatography Coupled with UV-Visible Diode-Array Detection. J. Chromatogr. A 2005, 1084, 71-79
44. Klejdus, B.; Vacek, J.; Benesova, L.; Kopecky, J.; Lapcik, O.; Kuban, V. Rapid-Resolution HPLC with Spectrometric Detection for the Determination and Identification of Isoflavones in Soy Preparations and Plant Extracts. Anal. Bioanal. Chem. 2007, 389, 2277-2285
45. Klejdus, B.; Mikelova, R.; Petrlova, J.; Potesil, D.; Adam, V.; Stiborová, M.; Hodek, P.; Vacek, J.; Kizek, R.; Kuba'n, V. Evaluation of Isoflavone Aglycon and Glycoside Distribution in Soy Plants and Soybeans by Fast Column High-Performance Liquid Chromatography Coupled with a Diode-Array Detector. J. Agric. Food Chem. 2005, 53 (15), 5848-5852
46. Ferrer, I.; Barber, L. B.; Thurman, E. M. Gas Chromatographic-Mass Spectrometric Fragmentation Study of Phytoestrogens as Their Trimethylsilyl Derivatives: Identification in Soy Milk and Wastewater Samples. J. Chromatogr. A 2009, 1216, 6024-6032
47. Molnar-Perl, I.; Fuzfai, Zs. Chromatographic, Capillary Electrophoretic and Capillary Electrochromatographic Techniques in the Analysis of Flavonoids. J. Chromatogr. A 2005, 1073, 201-227
48. Delmonte, P.; Perry, J.; Rader J. I. Determination of Isoflavones in Dietary Supplements Containing Soy, Red Clover and Kudzu: Extraction Followed by Basic or Acid Hydrolysis. J. Chromatogr. A 2006, 1107, 59-69
49. Chen, L.; Zhao, X.; Plummer, S.; Tang, J.; Games, D. E. Quantitative Determination and Structural Characterization of Isoflavones in Nutrition Supplements by Liquid Chromatography-Mass Spectrometry. J. Chromatogr. A 2005, 1082, 60-70
50. Erdemoglu, N.; Tosun, F.; Eroglu, Y. LC-MS Analysis of Daidzein in the Turkish Genista Species. Chem. Nat. Compd. 2006, 42 (5), 517-519
51. Gatea, F.; Danila, A. O.; Radu, G. L. Quantification of Some Phytoestrogens from Vegetal Extracts by HPLC. Rom. Biol. Sci. 2007, 5, 47-48
52. Otieno, D. O.; Rose, H.; Shah, N. P. Profiling and Quantification of Isoflavones in Soymilk from Soy Protein Isolate Using Extracted Ion Chromatography and Positive Ion Fragmentation Techniques. Food Chemistry. 2007, 105, 1642-1651
53. Luthria, D. L.; Biswas, R.; Natarajan, S. Comparison of Extraction Solvents and Techniques Used for the Assay of Isoflavones from Soybean. Food Chem. 2007, 105, 325-333
54. Gledhill, A. Analysis of Soy Isoflavones from a Dietary Supplement Using UPLC with PDA and SQ Detection. In Acquity UPLC System. UPLC and UPLC=MS Application Notebook 2007, 12-15
55. Klejdus, B.; Vacek, J.; Lojkova, L.; Benesova, L.; Kuban, V. Ultrahigh-Pressure Liquid Chromatography of Isoflavones and Phenolic Acids on Different Stationary Phases. J. Chromatogr. A 2008, 1195, 52-59
56. Visnevschi-Necrasov, T.; Cunha, S. C.; Nunes, E.; Oliveira, M. B. P. P. Optimization of Matrix Solid-Phase Dispersion Extraction Method for the Analysis of Isoflavones in Trifolium Pretense. J. Chromatogr. A 2009, 1216, 3720-3724
57. Schwartz, H.; Sontag, G. Comparison of Sample Preparation Methods for Analysis of Isoflavones in Foodstuffs. Anal. Chim. Acta 2009, 633, 204-215
58. Fiechter, G.; Raba, B.; Jungmayr, A.; Mayer, H. K. Characterization of Isoflavone Composition in Soy-Based Nutritional Supplements via Ultra Performance Liquid Chromatography. Anal. Chim. Acta 2010, 672 (1-2), 72-78
59. Novakova, L.; Matysova, L.; Solich, P. Advantages of Application of UPLC in Pharmaceutical Analysis. Talanta 2006, 68, 908-918
60. Wren, S. A. C.; Tchelitcheff, P. Use of Ultra-Performance Liquid Chromatography in Pharmaceutical Development. J. Chromatogr. A 2006, 1119, 140-146
61. Merken, H. M.; Beecher, G. R. Measurement of Food Flavonoids by High-Performance Liquid Chromatography: A Review. J. Agric. Food Chem. 2000, 48 (3), 577-599
62. Rybak, Mi 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
63. Bacaloni, A.; Cavaliere, C.; Faberi, A.; Foglia, P.; Samperi, R.; Lagana, A. Determination of Isoflavones and Coumestrol in River Water and Domestic Wastewater Sewage Treatment Plants. Anal. Chim. Acta 2005, 531, 229-237
64. McMaster, M. C. LC=MS: A Practical User's Guide; John Wiley & Sons: Hoboken, NJ, 2005, pp. 51-53
65. Souverain, S.; Rudaz, S.; Veuthey, J.-L. Matrix Effect in LC-ESI-MS and LC-APCI-MS with Off-line and On-line Extraction Procedures. J. Chromatogr. A 2004, 1058, 61-66
66. Stüber, M.; Reemtsma, T. Evaluation of Three Calibration Methods to Compensate Matrix Effects in Environmental Analysis with LC-ESI-MS. Anal. Bioanal. Chem. 2004, 378, 910-916
67. de Rijke, E.; Out, P.; Niessen, W. M. A.; Ariese, F.; Gooijer, C.; Brinkman, U. A. Th. Analytical Separation and Detection Methods for Flavonoids. J. Chromatogr. A 2006, 1112, 31-63
68. Klejdus, B.; Vacek, J.; Adam, V.; Zehnalek, J.; Kizek, R.; Trnkova, L.; Kuban, V. Determination of Isoflavones in Soybean Food and Human Urine Using Liquid Chromatography with Electrochemical Detection. J. Chromatogr. B 2004, 806 (2), 101-111
69. Klejdus, B.; Vitamvasova-Sterbova, D.; Kuban, V. Identification of Isoflavone Conjugates in Red Clover (Trifolium pratense) by Liquid Chromatography-Mass Spectrometry after Two-Dimensional Solid- Phase Extraction. Anal. Chim. Acta 2001, 450 (1-2), 81-97
70. Wu, Q.; Wang, M.; Simon, J. E.; Determination of Isoflavones in Red Clover and Related Species by High-Performance Liquid Chromatography Combined with Ultraviolet and Mass Spectrometric Detection. J. Chromatogr. A 2003, 1016 (2), 195-209
71. Prasain, J. K.; Jones, K.; Kirk, M.; Wilson, L.; Smith-Johnson, M.; Weaver, C.; Barnes, S. Profiling and quantification of isoflavonoids in Kudzu dietary Supplements by High-Performance Liquid Chromatography and Electrospray Ionization Tandem Mass Spectrometry. J. Agr. Food Chem. 2003, 51, 4213-4218
72. Luczkiewicz, M.; Piotrowski, A. Two-Stage System for Micropropagation of Several Genista Plants Producing Large Amounts of Phytoestrogens. Z Naturforsch C. 2005, 60 (7-8), 557-566
73. Tosun, F.; Erdem, C. K.; Eroǧlu, Y. Determination of Genistein in the Turkish Genista L. Species by LC-MS. Pharmazie 2003, 58 (8), 549-550