New concepts, experimental approaches, and dereplication strategies for the discovery of novel phytoestrogens from natural sources

Planta Medica

Volumn 79, Issue 7, 2013, Pages 514-532

  Michel, Thomas ^a   Halabalaki, Maria ^a   Skaltsounis, Alexios Leandros ^a  

^a UNIVERSITY OF ATHENS   (Greece)

Author keywords

dereplication; extraction; identification; isolation; phytoestrogens; plant extract

Indexed keywords

ACORUS GRAMINEUS EXTRACT; ARTEMISIA CAPILLARIS EXTRACT; CAESALPINIA SAPPAN EXTRACT; CUSCUTA CHINENSIS EXTRACT; CYPERUS ROTUNDUS EXTRACT; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; ISOFLAVONOID; PHYTOESTROGEN; PLANT EXTRACT; UNCLASSIFIED DRUG;

CHINESE MEDICINE; COUNTER CURRENT CHROMATOGRAPHY; COUNTERCURRENT EXTRACTION; DRUG ISOLATION; DRUG SCREENING; EXTRACTION AND EXTRACTS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HORMONE DETERMINATION; HUMAN; LIGAND BINDING; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MICROWAVE ASSISTED EXTRACTION; NONHUMAN; PHYTOCHEMISTRY; PRESSURIZED LIQUID EXTRACTION; REVIEW; SUBCRITICAL WATER EXTRACTION; SUPERCRITICAL FLUID EXTRACTION; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; ULTRASOUND ASSISTED EXTRACTION;

FABACEAE;

EID: 84877873492     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0032-1328300     Document Type: Review

References (181)

1. Cos P., De Bruyne T., Apers S., Berghe D. V., Pieters L., Vlietinck A. J. Phytoestrogens: recent developments. Planta Med: 2003; 69 589 599 (Pubitemid 37041052)
2. Ososki A. L., Kennelly E. J. Phytoestrogens: a review of the present state of research. Phytother Res: 2003; 17 845 869 (Pubitemid 37157993)
3. Cornwell T., Cohick W., Raskin I. Dietary phytoestrogens and health. Phytochemistry: 2004; 65 995 1016 (Pubitemid 38542736)
4. Simons R., Gruppen H., Bovee T. FH, Verbruggen M. A., Vincken J. P. Prenylated isoflavonoids from plants as selective estrogen receptor modulators (phytoSERMs). Food Funct: 2012; 3 810 827
5. Pitkin J. Alternative and complementary therapies for the menopause. Menopause Int: 2012; 18 20 27
6. Al-Anazi A. F., Qureshi V. F., Javaid K., Qureshi S. Preventive effects of phytoestrogens against postmenopausal osteoporosis as compared to the available therapeutic choices: An overview. J Nat Sci Biol Med: 2011; 2 154 163
7. Kuiper G. GJM, Lemmen J. G., Carlsson B., Corton J. C., Safe S. H., van der Saag P. T., van der Burg B., Gustafsson J. Å. Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor β Endocrinology: 1998; 139 4252 4263 (Pubitemid 28513713)
8. Kumar R., Thompson E. B. The structure of the nuclear hormone receptors. Steroids: 1999; 64 310 319 (Pubitemid 29284331)
9. Katzenellenbogen B. S., Korach K. S. Editorial: A new actor in the estrogen receptor drama-Enter ER- β Endocrinology: 1997; 138 861 862 (Pubitemid 27089734)
10. Brzezinski A., Debi A. Phytoestrogens: the "naturalo" selective estrogen receptor modulators? Eur J Obstet Gynecol Reprod Biol: 1999; 85 47 51 (Pubitemid 29248782)
11. Kellis J., Vickery L. Inhibition of human estrogen synthetase (aromatase) by flavones. Science: 1984; 225 1032 1034 (Pubitemid 14066315)
12. Pelissero C., Lenczowski M. JP, Chinzi D., Davail-Cuisset B., Sumpter J. P., Fostier A. Effects of flavonoids on aromatase activity, an in vitro study. J Steroid Biochem Mol Biol: 1996; 57 215 223 (Pubitemid 26169976)
13. Makela S., Davis V. L., Tally W. C., Korkman J., Salo L., Vihko R., Santti R., Korach K. S. Dietary estrogens act through estrogen receptor-mediated processes and show no antiestrogenicity in cultured breast cancer cells. Environ Health Perspect: 1994; 102 572 578 (Pubitemid 24241281)
14. Adlercreutz H., Mousavi Y., Clark J., Höckerstedt K., Hämäläinen E., Wähälä K., Mäkelä T., Hase T. Dietary phytoestrogens and cancer: in vitro and in vivo studies. J Steroid Biochem Mol Biol: 1992; 41 331 337
15. Atkinson C., Newton K., Stanczyk F., Westerlind K., Li L., Lampe J. Daidzein-metabolizing phenotypes in relation to serum hormones and sex hormone binding globulin, and urinary estrogen metabolites in premenopausal women in the United States. Cancer Causes Control: 2008; 19 1085 1093
16. Dixon R. A. Phytoestrogens. Annu Rev Plant Biol: 2004; 55 225 261 (Pubitemid 38940932)
17. Tahara S., Ibrahim R. K. Prenylated isoflavonoids - an update. Phytochemistry: 1995; 38 1073 1094
18. Fokialakis N., Lambrinidis G., Mitsiou D. J., Aligiannis N., Mitakou S., Skaltsounis A. L., Pratsinis H., Mikros E., Alexis M. N. A new class of phytoestrogens: Evaluation of the estrogenic activity of deoxybenzoins. Chem Biol: 2004; 11 397 406 (Pubitemid 39403879)
19. Hu J. Y., Aizawa T. Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals. Water Res: 2003; 37 1213 1222 (Pubitemid 36206468)
20. Veitch N. C. Isoflavonoids of the Leguminosae. Nat Prod Rep: 2009; 26 776 802
21. Reynaud J., Guilet D., Terreux R., Lussignol M., Walchshofer N. Isoflavonoids in non-leguminous families: an update. Nat Prod Rep: 2005; 22 504 515 (Pubitemid 41188650)
22. Booth N. L., Piersen C. E., Banuvar S., Geller S. E., Shulman L. P., Farnsworth N. R. Clinical studies of red clover (Trifolium pratense) dietary supplements in menopause: a literature review. Menopause: 2006; 13 251 264
23. Bora K. S., Sharma A. Phytochemical and pharmacological potential of Medicago sativa: a review. Pharm Biol: 2011; 49 211 220
24. Stevenson P. C., Veitch N. C. The distribution of isoflavonoids in cicer. Phytochemistry: 1998; 48 995 1001 (Pubitemid 28304113)
25. Farag M. A., Porzel A., Wessjohann L. A. Comparative metabolite profiling and fingerprinting of medicinal licorice roots using a multiplex approach of GC-MS, LC-MS and 1D NMR techniques. Phytochemistry: 2012; 76 60 72
26. Wong K. H., Li G. Q., Li K. M., Razmovski-Naumovski V., Chan K. Kudzu root: traditional uses and potential medicinal benefits in diabetes and cardiovascular diseases. J Ethnopharmacol: 2011; 134 584 607
27. Hong Y. H., Wang S. C., Hsu C., Lin B. F., Kuo Y. H., Huang C. J. Phytoestrogenic compounds in alfalfa sprout (Medicago sativa) beyond coumestrol. J Agric Food Chem: 2010; 59 131 137
28. Chadwick L. R., Pauli G. F., Farnsworth N. R. The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on estrogenic properties. Phytomedicine: 2006; 13 119 131 (Pubitemid 41799601)
29. Possemiers S., Bolca S., Grootaert C., Heyerick A., Decroos K., Dhooge W., De Keukeleire D., Rabot S., Verstraete W., Van de Wiele T. The prenylflavonoid isoxanthohumol from hops (Humulus lupulus L.) is activated into the potent phytoestrogen 8-prenylnaringenin in vitro and in the human intestine. J Nutr: 2006; 136 1862 1867 (Pubitemid 43973589)
30. Pan J. Y., Chen S. L., Yang M. H., Wu J., Sinkkonen J., Zou K. An update on lignans: natural products and synthesis. Nat Prod Rep: 2009; 26 1251 1292
31. Sakakibara N., Nakatsubo T., Suzuki S., Shibata D., Shimada M., Umezawa T. Metabolic analysis of the cinnamate/monolignol pathway in Carthamus tinctorius seeds by a stable-isotope-dilution method. Org Biomol Chem: 2007; 5 802 815
32. Smeds A. I., Eklund P. C., Sjöholm R. E., Willför S. M., Nishibe S., Deyama T., Holmbom B. R. Quantification of a broad spectrum of lignans in cereals, oilseeds, and nuts. J Agric Food Chem: 2007; 55 1337 1346
33. Dinelli G., Marotti I., Bosi S., Benedettelli S., Ghiselli L., Cortacero-Ramírez S., Carrasco-Pancorbo A., Segura-Carretero A., Fernández-Gutiérrez A. Lignan profile in seeds of modern and old Italian soft wheat (Triticum aestivum L.) cultivars as revealed by CE-MS analyses. Electrophoresis: 2007; 28 4212 4219 (Pubitemid 350187330)
34. Lee I. A., Joh E. H., Kim D. H. Arctigenin isolated from the seeds of Arctium lappa ameliorates memory deficits in mice. Planta Med: 2011; 77 1525 1527
35. Shen T., Wang X. N., Lou H. X. Natural stilbenes: an overview. Nat Prod Rep: 2009; 26 916 935
36. Lopes R. M., Agostini-Costa T. NDS, Gimenes M. A., Silveira D. M. Chemical composition and biological activities of Arachis species. J Agric Food Chem: 2011; 59 4321 4330
37. Möller F., Zierau O., Jandausch A., Rettenberger R., Kaszkin-Bettag M., Vollmer G. Subtype-specific activation of estrogen receptors by a special extract of Rheum rhaponticum (ERr 731®), its aglycones and structurally related compounds in U2OS human osteosarcoma cells. Phytomedicine: 2007; 14 716 726 (Pubitemid 47554506)
38. Wober J., Möller F., Richter T., Unger C., Weigt C., Jandausch A., Zierau O., Rettenberger R., Kaszkin-Bettag M., Vollmer G. Activation of estrogen receptor- β by a special extract of Rheum rhaponticum (ERr 731®), its aglycones and structurally related compounds. J Steroid Biochem Mol Biol: 2007; 107 191 201 (Pubitemid 47393556)
39. Martin P. M., Hortwitz K. B., Ryan D. S., McGuire W. L. Phytoestrogen interaction with estrogen receptors in human breast cancer cells. Endocrinology: 1978; 103 1860 1867 (Pubitemid 9052644)
40. Halabalaki M., Aligiannis N., Papoutsi Z., Mitakou S., Moutsatsou P., Sekeris C., Skaltsounis A. L. Three new arylobenzofurans from Onobrychis ebenoides and evaluation of their binding affinity for the estrogen receptor. J Nat Prod: 2000; 63 1672 1674 (Pubitemid 32038613)
41. Suksamrarn A., Ponglikitmongkol M., Wongkrajang K., Chindaduang A., Kittidanairak S., Jankam A., Yingyongnarongkul B. E., Kittipanumat N., Chokchaisiri R., Khetkam P., Piyachaturawat P. Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation. Bioorg Med Chem: 2008; 16 6891 6902
42. Lim S. H., Ha T. Y., Ahn J., Kim S. Estrogenic activities of Psoralea corylifolia L. seed extracts and main constituents. Phytomedicine: 2011; 18 425 430
43. Choo W. S., Birch J., Dufour J. P. Physicochemical and quality characteristics of cold-pressed flaxseed oils. J Food Comp Anal: 2007; 20 202 211 (Pubitemid 46228278)
44. Takeda S., Yamamoto I., Watanabe K. Modulation of Δ9- tetrahydrocannabinol-induced MCF-7 breast cancer cell growth by cyclooxygenase and aromatase. Toxicology: 2009; 259 25 32
45. Su S. L., Duan J. A., Tang Y. P., Zhang X., Yu L., Jiang F. R., Zhou W., Luo D., Ding A. W. Isolation and biological activities of neomyrrhaol and other terpenes from the resin of Commiphora myrrha. Planta Med: 2009; 75 351 355
46. Michel J. L., Chen Y., Zhang H., Huang Y., Krunic A., Orjala J., Veliz M., Soni K. K., Soejarto D. D., Caceres A., Perez A., Mahady G. B. Estrogenic and serotonergic butenolides from the leaves of Piper hispidum Swingle (Piperaceae). J Ethnopharmacol: 2010; 129 220 226
47. Maiti A., Reddy P. VN, Sturdy M., Marler L., Pegan S. D., Mesecar A. D., Pezzuto J. M., Cushman M. Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities. J Med Chem: 2009; 52 1873 1884
48. Flemming J., Madarnas Y., Franek J. Fulvestrant for systemic therapy of locally advanced or metastatic breast cancer in postmenopausal women: a systematic review. Breast Cancer Res Treat: 2009; 115 255 268
49. Fang N., Casida J. E. New bioactive flavonoids and stilbenes in cubé resin insecticide. J Nat Prod: 1999; 62 205 210 (Pubitemid 29137889)
50. Harvey A. L. Natural products in drug discovery. Drug Discov Today: 2008; 13 894 901
51. Nahrstedt A., Butterweck V. Lessons learned from herbal medicinal products: the example of St. Johns wort. J Nat Prod: 2010; 73 1015 1021
52. Tu Y., Jeffries C., Ruan H., Nelson C., Smithson D., Shelat A. A., Brown K. M., Li X. C., Hester J. P., Smillie T., Khan I. A., Walker L., Guy K., Yan B. Automated high-throughput system to fractionate plant natural products for drug discovery. J Nat Prod: 2010; 73 751 754
53. van Beek T., Tetala K., Koleva I., Dapkevicius A., Exarchou V., Jeurissen S., Claassen F., van der Klift E. Recent developments in the rapid analysis of plants and tracking their bioactive constituents. Phytochem Rev: 2009; 8 387 399
54. Zaugg J., Eickmeier E., Rueda D. C., Hering S., Hamburger M. HPLC-based activity profiling of Angelica pubescens roots for new positive GABAA receptor modulators in Xenopus oocytes. Fitoterapia: 2011; 82 434 440
55. Potterat O., Hamburger M. Drug discovery and development with plant-derived compounds. Prog Drug Res: 2008; 65 45 118
56. Giera M., Heus F., Janssen L., Kool J., Lingeman H., Irth H. Microfractionation revisited: a 1536 well high resolution screening assay. Anal Chem: 2009; 81 5460 5466
57. Grata E., Guillarme D., Glauser G., Boccard J., Carrupt P. A., Veuthey J. L., Rudaz S., Wolfender J. L. Metabolite profiling of plant extracts by ultra-high-pressure liquid chromatography at elevated temperature coupled to time-of-flight mass spectrometry. J Chromatogr A: 2009; 1216 5660 5668
58. Wolfender J. L., Ndjoko K., Hostettmann K. Liquid chromatography with ultraviolet absorbance-mass spectrometric detection and with nuclear magnetic resonance spectrometry: a powerful combination for the on-line structural investigation of plant metabolites. J Chromatogr A: 2003; 1000 437 455 (Pubitemid 36638469)
59. Koehn F. E. High impact technologies for natural products screening. In: Petersen F., Amstutz R. editors Natural compounds as drugs, Volume I. Progress in drug research, Vol. 65. Basel Birkhäuser: 2008; 175 210
60. Koehn F. E., Carter G. T. The evolving role of natural products in drug discovery. Nat Rev Drug Discov: 2005; 4 206 220 (Pubitemid 40372555)
61. Armenta S., Garrigues S., de la Guardia M. Green analytical chemistry. Trends Anal Chem: 2008; 27 497 511
62. Mendiola J. A., Herrero M., Cifuentes A., Ibañez E. Use of compressed fluids for sample preparation: food applications. J Chromatogr A: 2007; 1152 234 246 (Pubitemid 46754006)
63. Vinatoru M., Toma M., Radu O., Filip P. I., Lazurca D., Mason T. J. The use of ultrasound for the extraction of bioactive principles from plant materials. Ultrason Sonochem: 1997; 4 135 139
64. Sparr Eskilsson C., Björklund E. Analytical-scale microwave-assisted extraction. J Chromatogr A: 2000; 902 227 250
65. Rostagno M. A., Villares A., Guillamón E., García-Lafuente A., Martínez J. A. Sample preparation for the analysis of isoflavones from soybeans and soy foods. J Chromatogr A: 2009; 1216 2 29
66. Zgórka G. Pressurized liquid extraction versus other extraction techniques in micropreparative isolation of pharmacologically active isoflavones from Trifolium L. species. Talanta: 2009; 79 46 53
67. Zgórka G. Studies on phytoestrogenic and nonphytoestrogenic compounds in Trifolium incarnatum L. and other clover species using pressurized liquid extraction and high performance column liquid chromatography with photodiode-array and fluorescence detection. J AOAC Int: 2011; 94 22 31
68. 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 (Pubitemid 47023028)
69. Ho C. HL, Cacace J. E., Mazza G. Extraction of lignans, proteins and carbohydrates from flaxseed meal with pressurized low polarity water. Food Sci Technol: 2007; 40 1637 1647 (Pubitemid 46976971)
70. Gil-Ramírez A., Mendiola J. A., Arranz E., Ruíz- Rodríguez A., Reglero G., Ibáñez E., Marín F. R. Highly isoxanthohumol enriched hop extract obtained by pressurized hot water extraction (PHWE). Chemical and functional characterization. Innov Food Sci Emerg Technol: 2012; 10.1016/j.ifset.2012.04.006
71. Teo C. C., Tan S. N., Yong J. WH, Hew C. S., Ong E. S. Pressurized hot water extraction (PHWE). J Chromatogr A: 2010; 1217 2484 2494
72. Herrero M., Mendiola J. A., Cifuentes A., Ibáñez E. Supercritical fluid extraction: Recent advances and applications. J Chromatogr A: 2010; 1217 2495 2511
73. Pyo D., Yoo J., Surh J. Comparison of supercritical fluid extraction and solvent extraction of isoflavones from soybeans. J Liq Chromatogr Relat Technol: 2009; 32 923 932
74. Bajer T., Adam M., Galla L., Ventura K. Comparison of various extraction techniques for isolation and determination of isoflavonoids in plants. J Sep Sci: 2007; 30 122 127 (Pubitemid 46157544)
75. Pascual-Martí M. C., Salvador A., Chafer A., Berna A. Supercritical fluid extraction of resveratrol from grape skin of Vitis vinifera and determination by HPLC. Talanta: 2001; 54 735 740 (Pubitemid 32458494)
76. Casas L., Mantell C., Rodríguez M., Martinez de la Ossa E. J., Roldán A., Ory I. D., Caro I., Blandino A. Extraction of resveratrol from the pomace of Palomino fino grapes by supercritical carbon dioxide. J Food Eng: 2010; 96 304 308
77. Chafer A., Pascual-Martí M. C., Salvador A., Berna A. Supercritical fluid extraction and HPLC determination of relevant polyphenolic compounds in grape skin. J Sep Sci: 2005; 28 2050 2056 (Pubitemid 41700683)
78. Choi Y., Kim J., Yoo K. P. High performance liquid chromatography- electrospray lonization MS-MS analysis Forsythia koreana fruits, leaves, and stems. Enhancement of the efficiency of extraction of arctigenin by use of supercritical-fluid extraction. Chromatographia: 2003; 57 73 79 (Pubitemid 36151109)
79. Michel T., Destandau E., Elfakir C. Evaluation of a simple and promising method for extraction of antioxidants from sea buckthorn (Hippophaë rhamnoides L.) berries: Pressurised solvent-free microwave assisted extraction. Food Chem: 2011; 126 1380 1386
80. Du G., Zhao H. Y., Zhang Q. W., Li G. H., Yang F. Q., Wang Y., Li Y. C., Wang Y. T. A rapid method for simultaneous determination of 14 phenolic compounds in Radix Puerariae using microwave-assisted extraction and ultra high performance liquid chromatography coupled with diode array detection and time-of-flight mass spectrometry. J Chromatogr A: 2010; 1217 705 714
81. Terigar B. G., Balasubramanian S., Boldor D., Xu Z., Lima M., Sabliov C. M. Continuous microwave-assisted isoflavone extraction system: design and performance evaluation. Bioresour Technol: 2010; 101 2466 2471
82. Nemes S., Orsat V. Microwave-assisted extraction of secoisolariciresinol diglucoside-method development. Food Bioprocess Technol: 2011; 4 1219 1227
83. Yu R., Yu R., Zhang X., Luo Z., Zhang H., Shao Y., Mei L., Tao Y. Dynamic microwave-assisted extraction of arctigenin from Saussurea medusa Maxim. Chromatographia: 2010; 71 335 339
84. Zgórka 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
85. Wu Y., Wang X., Fan E. Optimisation of ultrasound-assisted extraction of puerarin and total isoflavones from Puerariae Lobatae Radix (Pueraria lobata (Wild.) Ohwi) with response surface methodology. Phytochem Anal: 2012; 23 513 519
86. Jiang R. W., Lau K. M., Lam H. M., Yam W. S., Leung L. K., Choi K. L., Waye M. MY, Mak T. CW, Woo K. S., Fung K. P. A comparative study on aqueous root extracts of Pueraria thomsonii and Pueraria lobata by antioxidant assay and HPLC fingerprint analysis. J Ethnopharmacol: 2005; 96 133 138 (Pubitemid 39575042)
87. Lee M. H., Lin C. C. Comparison of techniques for extraction of isoflavones from the root of Radix puerariae: Ultrasonic and pressurized solvent extractions. Food Chem: 2007; 105 223 228
88. Lou Z., Wang H., Zhu S., Zhang M., Gao Y., Ma C., Wang Z. Improved extraction and identification by ultra performance liquid chromatography tandem mass spectrometry of phenolic compounds in burdock leaves. J Chromatogr A: 2010; 1217 2441 2446
89. Cheng X. L., Wan J. Y., Li P., Qi L. W. Ultrasonic/microwave assisted extraction and diagnostic ion filtering strategy by liquid chromatography- quadrupole time-of-flight mass spectrometry for rapid characterization of flavonoids in Spatholobus suberectus. J Chromatogr A: 2011; 1218 5774 5786
90. Chukwumah Y. C., Walker L. T., Verghese M., Bokanga M., Ogutu S., Alphonse K. Comparison of extraction methods for the quantification of selected phytochemicals in peanuts (Arachis hypogaea). J Agric Food Chem: 2006; 55 285 290
91. Pauli G. F., Pro S. M., Friesen J. B. Countercurrent separation of natural products. J Nat Prod: 2008; 71 1489 1508
92. Costa F. D., Leitão G. G. Strategies of solvent system selection for the isolation of flavonoids by countercurrent chromatography. J Sep Sci: 2010; 33 336 347
93. Yoon K. D., Chin Y. W., Kim J. Centrifugal partition chromatography: Application to natural products in 1994-2009. J Liq Chromatogr Relat Technol: 2010; 33 1208 1254
94. Du Q., Li B. Identification of antioxidant compounds of Mucuna sempervirens by high-speed counter-current chromatographic separation-DPPH radical scavenging detection and their oestrogenic activity. Food Chem: 2012; 131 1181 1186
95. Simons R., Vincken J. P., Mol L. AM, The S. AM, Bovee T. FH, Luijendijk T. JC, Verbruggen M. A., Gruppen H. Agonistic and antagonistic estrogens in licorice root (Glycyrrhiza glabra). Anal Bioanal Chem: 2011; 401 301 313
96. Guillarme D., Ruta J., Rudaz S., Veuthey J. L. New trends in fast and high-resolution liquid chromatography: a critical comparison of existing approaches. Anal Bioanal Chem: 2010; 397 1069 1082
97. Chen G., Pramanik B. N., Liu Y. H., Mirza U. A. Applications of LC/MS in structure identifications of small molecules and proteins in drug discovery. J Mass Spectrom: 2007; 42 279 287 (Pubitemid 46426672)
98. Glish G. L., Vachet R. W. The basics of mass spectrometry in the twenty-first century. Nat Rev Drug Discov: 2003; 2 140 150 (Pubitemid 37361646)
99. 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 (Pubitemid 46001372)
100. 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 (Pubitemid 38624358)
101. Rostagno M. A., Palma M., Barroso C. G. Solid-phase extraction of soy isoflavones. J Chromatogr A: 2005; 1076 110 117 (Pubitemid 40731502)
102. Rostagno M. A., Palma M., Barroso C. G. Microwave assisted extraction of soy isoflavones. Anal Chim Acta: 2007; 588 274 282 (Pubitemid 46454254)
103. Du G., Zhao H., Song Y., Zhang Q., Wang Y. Rapid simultaneous determination of isoflavones in Radix puerariae using high-performance liquid chromatography-triple quadrupole mass spectrometry with novel shell-type column. J Sep Sci: 2011; 34 2576 2585
104. Manchón N., DArrigo M., García-Lafuente A., Guillamón E., Villares A., Ramos A., Martínez J. A., Rostagno M. A. Fast analysis of isoflavones by high-performance liquid chromatography using a column packed with fused-core particles. Talanta: 2010; 82 1986 1994
105. Klejdus B., Mikelová R., Petrlová J., Potěšil D., Adam V., Stiborová M., Hodek P., Vacek J., Kizek R., Kubáň 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 (Pubitemid 40966912)
106. Klejdus B., Mikelova R., Petrlova J., Potesil D., Adam V., Stiborova M., Hodek P., Vacek J., Kizek R., Kuban 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 5848 5852 (Pubitemid 41126615)
107. Klejdus B., Lojková L., Lapčík O., Koblovská R., Moravcová J., Kubáň V. Supercritical fluid extraction of isoflavones from biological samples with ultra-fast high-performance liquid chromatography/mass spectrometry. J Sep Sci: 2005; 28 1334 1346 (Pubitemid 41195342)
108. Klejdus B., Lojková L., Plaza M., Šnóblová M., Štěrbová D. Hyphenated technique for the extraction and determination of isoflavones in algae: ultrasound-assisted supercritical fluid extraction followed by fast chromatography with tandem mass spectrometry. J Chromatogr A: 2010; 1217 7956 7965
109. Klejdus B., Vacek J., Benešová L., Kopecký J., Lapčík O., Kubáň 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 (Pubitemid 350198044)
110. Churchwell M. I., Twaddle N. C., Meeker L. R., Doerge D. R. Improving LC-MS sensitivity through increases in chromatographic performance: comparisons of UPLC-ES/MS/MS to HPLC-ES/MS/MS. J Chromatogr B: 2005; 825 134 143 (Pubitemid 41423596)
111. Klejdus B., Vacek J., Lojková L., Benešová L., Kubáň V. Ultrahigh-pressure liquid chromatography of isoflavones and phenolic acids on different stationary phases. J Chromatogr A: 2008; 1195 52 59
112. Oleszek W., Stochmal A., Janda B. Concentration of isoflavones and other phenolics in the aerial parts of Trifolium species. J Agric Food Chem: 2007; 55 8095 8100
113. Prokudina E. A., Havlíček L., Al-Maharik N., Lapčík O., Strnad M., Gruz J. Rapid UPLC-ESI-MS/MS method for the analysis of isoflavonoids and other phenylpropanoids. J Food Comp Anal: 2012; 26 36 42
114. Simons R., Vincken J. P., Roidos N., Bovee T. FH, van Iersel M., Verbruggen M. A., Gruppen H. Increasing soy isoflavonoid content and diversity by simultaneous malting and challenging by a fungus to modulate estrogenicity. J Agric Food Chem: 2011; 59 6748 6758
115. Eugster P. J., Guillarme D., Rudaz S., Veuthey J. L., Carrupt P. A., Wolfender J. L. Ultra high pressure liquid chromatography for crude plant extract profiling. J AOAC Int: 2011; 94 51 70
116. Farag M. A., Porzel A., Schmidt J., Wessjohann L. A. Metabolite profiling and fingerprinting of commercial cultivars of Humulus lupulus L. (hop): a comparison of MS and NMR methods in metabolomics. Metabolomics: 2012; 8 492 507
117. Farag M. A., Huhman D. V., Lei Z., Sumner L. W. Metabolic profiling and systematic identification of flavonoids and isoflavonoids in roots and cell suspension cultures of Medicago truncatula using HPLC-UV-ESI-MS and GC-MS. Phytochemistry: 2007; 68 342 354 (Pubitemid 46108044)
118. Montoro P., Maldini M., Russo M., Postorino S., Piacente S., Pizza C. Metabolic profiling of roots of liquorice (Glycyrrhiza glabra) from different geographical areas by ESI/MS/MS and determination of major metabolites by LC-ESI/MS and LC-ESI/MS/MS. J Pharm Biomed Anal: 2011; 54 535 544
119. Simons R., Vincken J. P., Bakx E. J., Verbruggen M. A., Gruppen H. A rapid screening method for prenylated flavonoids with ultra-high-performance liquid chromatography/electrospray ionisation mass spectrometry in licorice root extracts. Rapid Commun Mass Spectrom: 2009; 23 3083 3093
120. Hanhineva K., Rogachev I., Aura A. M., Aharoni A., Poutanen K., Mykkänen H. Identification of novel lignans in the whole grain rye bran by non-targeted LC-MS metabolite profiling. Metabolomics: 2012; 8 399 409
121. Jaroszewski J. W. Hyphenated NMR methods in natural products research, Part 2: HPLC-SPE-NMR and other new trends in NMR hyphenation. Planta Med: 2005; 71 795 802 (Pubitemid 41501173)
122. Lambert M., Hansen S. H., Sairafianpour M., Jaroszewski J. W. Rapid extract dereplication using HPLC-SPE-NMR: analysis of isoflavonoids from Smirnowia iranica. J Nat Prod: 2005; 68 1500 1509 (Pubitemid 41658901)
123. Wang C. Y., Lam S. H., Tseng L. H., Lee S. S. Rapid screening of lignans from Phyllanthus myrtifolius and stilbenoids from Syagrus romanzoffiana by HPLC-SPE-NMR. Phytochem Anal: 2011; 22 352 360
124. Wang C. Y., Lee S. S. Analysis and identification of lignans in Phyllanthus urinaria by HPLC-SPE-NMR. Phytochem Anal: 2005; 16 120 126
125. Schütz C., Quitschau M., Hamburger M., Potterat O. Profiling of isoflavonoids in Iris germanica rhizome extracts by microprobe NMR and HPLC-PDA-MS analysis. Fitoterapia: 2011; 82 1021 1026
126. Djiogue S., Halabalaki M., Alexi X., Njamen D., Fomum Z. T., Alexis M. N., Skaltsounis A. L. Isoflavonoids from Erythrina poeppigiana: evaluation of their binding affinity for the estrogen receptor. J Nat Prod: 2009; 72 1603 1607
127. Djiogue S., Njamen D., Halabalaki M., Kretzschmar G., Beyer A., Mbanya J. C., Skaltsounis A. L., Vollmer G. Estrogenic properties of naturally occurring prenylated isoflavones in U2OS human osteosarcoma cells: Structure-activity relationships. J Steroid Biochem Mol Biol: 2010; 120 184 191
128. Boué S. M., Wiese T. E., Nehls S., Burow M. E., Elliott S., Carter-Wientjes C. H., Shih B. Y., McLachlan J. A., Cleveland T. E. Evaluation of the estrogenic effects of legume extracts containing phytoestrogens. J Agric Food Chem: 2003; 51 2193 2199
129. Lai W. C., Wang H. C., Chen G. Y., Yang J. C., Korinek M., Hsieh C. J., Nozaki H., Hayashi K. I., Wu C. C., Wu Y. C., Chang F. R. Using the pER8:GUS reporter system to screen for phytoestrogens from Caesalpinia sappan. J Nat Prod: 2011; 74 1698 1706
130. Tsai Y. C., Lai W. C., Du Y. C., Wu S. F., El-Shazly M., Lee C. L., Yen M. H., Hou M. F., Wu Y. C., Chang F. R. Lignan and flavonoid phytoestrogens from the seeds of Cuscuta chinensis. J Nat Prod: 2012; 10.1021/np200974e
131. Umehara K., Nemoto K., Matsushita A., Terada E., Monthakantirat O., De-Eknamkul W., Miyase T., Warashina T., Degawa M., Noguchi H. Flavonoids from the heartwood of the thai medicinal plant Dalbergia parviflora and their effects on estrogenic-responsive human breast cancer cells. J Nat Prod: 2009; 72 2163 2168
132. De Naeyer A., Vanden Berghe W., Pocock V., Milligan S., Haegeman G., De Keukeleire D. Estrogenic and anticarcinogenic properties of kurarinone, a lavandulyl flavanone from the roots of Sophora flavescens. J Nat Prod: 2004; 67 1829 1832 (Pubitemid 39602359)
133. Shi S. Y., Zhang Y. P., Jiang X. Y., Chen X. Q., Huang K. L., Zhou H. H. Coupling HPLC to on-line, post-column (bio)chemical assays for high-resolution screening of bioactive compounds from complex mixtures. Trends Anal Chem: 2009; 28 865 877
134. Oosterkamp A. J., Villaverde Herraiz M. T., Irth H., Tjaden U. R., van der Greef J. Reversed-phase liquid chromatography coupled on-line to receptor affinity detection based on the human estrogen receptor. Anal Chem: 1996; 68 1201 1206
135. van Elswijk D. A., Irth H. Analytical tools for the detection and characterization of biologically active compounds from nature. Phytochem Rev: 2002; 1 427 439 (Pubitemid 41413237)
136. Schobel U., Frenay M., Van Elswijk D. A., McAndrews J. M., Long K. R., Olson L. M., Bobzin S. C., Irth H. High resolution screening of plant natural product extracts for estrogen receptor α and β binding activity using an online HPLC-MS biochemical detection system. J Biomol Screen: 2001; 6 291 303 (Pubitemid 33027496)
137. van Elswijk D. A., Schobel U. P., Lansky E. P., Irth H., van der Greef J. Rapid dereplication of estrogenic compounds in pomegranate (Punica granatum) using on-line biochemical detection coupled to mass spectrometry. Phytochemistry: 2004; 65 233 241 (Pubitemid 38147362)
138. Reinen J., Kool J., Vermeulen N. Reversed-phase liquid chromatography coupled on-line to estrogen receptor bioaffinity detection based on fluorescence polarization. Anal Bioanal Chem: 2008; 390 1987 1998
139. Jonker N., Kool J., Irth H., Niessen W. Recent developments in protein-ligand affinity mass spectrometry. Anal Bioanal Chem: 2011; 399 2669 2681
140. Schriemer D. C., Bundle D. R., Li L., Hindsgaul O. Micro-scale frontal affinity chromatography with mass spectrometric detection: A new method for the screening of compound libraries. Angew Chem Int Ed: 1998; 37 3383 3387 (Pubitemid 29044866)
141. Slon-Usakiewicz J. J., Ng W., Dai J. R., Pasternak A., Redden P. R. Frontal affinity chromatography with MS detection (FAC-MS) in drug discovery. Drug Discov Today: 2005; 10 409 416 (Pubitemid 40444656)
142. Calleri E., Temporini C., Caccialanza G., Massolini G. Target-based drug discovery: the emerging success of frontal affinity chromatography coupled to mass spectrometry. ChemMedChem: 2009; 4 905 916
143. Chan N. WC, Lewis D. F., Rosner P. J., Kelly M. A., Schriemer D. C.
144. Moaddel R., Lu L., Baynham M., Wainer I. W. Immobilized receptor- and transporter-based liquid chromatographic phases for on-line pharmacological and biochemical studies: a mini-review. J Chromatogr B: 2002; 768 41 53 (Pubitemid 34142295)
145. Ng W., Dai J. R., Slon-Usakiewicz J. J., Redden P. R., Pasternak A., Reid N. Automated multiple ligand screening by Frontal Affinity Chromatography-Mass Spectrometry (FAC-MS). J Biomol Scr: 2007; 12 167 174 (Pubitemid 46364426)
146. van Breemen R. B., Huang C. R., Nikolic D., Woodbury C. P., Zhao Y. Z., Venton D. L. Pulsed ultrafiltration mass spectrometry: a new method for screening combinatorial libraries. Anal Chem: 1997; 69 2159 2164
147. Johnson B. M., Nikolic D., van Breemen R. B. Applications of pulsed ultrafiltration-mass spectrometry. Mass Spectrom Rev: 2002; 21 76 86 (Pubitemid 35355218)
148. Liu J., Burdette J. E., Xu H., Gu C., van Breemen R. B., Bhat K. PL, Booth N., Constantinou A. I., Pezzuto J. M., Fong H. HS, Farnsworth N. R., Bolton J. L. Evaluation of estrogenic activity of plant extracts for the potential treatment of menopausal symptoms. J Agric Food Chem: 2001; 49 2472 2479 (Pubitemid 32843277)
149. Liu J., Burdette J. E., Sun Y., Deng S., Schlecht S. M., Zheng W., Nikolic D., Mahady G., van Breemen R. B., Fong H. HS, Pezzuto J. M., Bolton J. L., Farnsworth N. R. Isolation of linoleic acid as an estrogenic compound from the fruits of Vitex agnus-castus L. (chaste-berry). Phytomedicine: 2004; 11 18 23 (Pubitemid 38196793)
150. Overk C. R., Yao P., Chadwick L. R., Nikolic D., Sun Y., Cuendet M. A., Deng Y., Hedayat A. S., Pauli G. F., Farnsworth N. R., van Breemen R. B., Bolton J. L. Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense). J Agric Food Chem: 2005; 53 6246 6253 (Pubitemid 41169368)
151. Choi Y., van Breemen R. B. Development of a screening assay for ligands to the estrogen receptor based on magnetic microparticles and LC-MS. Comb Chem High Throughput Screen: 2008; 11 1 6
152. Onorato J., Henion J. D. Evaluation of triterpene glycoside estrogenic activity using LC/MS and immunoaffinity extraction. Anal Chem: 2001; 73 4704 4710 (Pubitemid 32953197)
153. Jonker N., Kretschmer A., Kool J., Fernandez A., Kloos D., Krabbe J. G., Lingeman H., Irth H. Online magnetic bead dynamic protein-affinity selection coupled to LC-MS for the screening of pharmacologically active compounds. Anal Chem: 2009; 81 4263 4270
154. Voldman J., Gray M. L., Schmidt M. A. Microfabrication in biology and medicine. Annu Rev Biomed Eng: 1999; 1 401 425 (Pubitemid 129740018)
155. Kostelac D., Rechkemmer G., Briviba K. Phytoestrogens modulate binding response of estrogen receptors α and β to the estrogen response element. J Agric Food Chem: 2003; 51 7632 7635
156. Chuang Y. J., Huang J. W., Makamba H., Tsai M. L., Li C. W., Chen S. H. Electrophoretic mobility shift assay on poly(ethylene glycol)-modified glass microchips for the study of estrogen responsive element binding. Electrophoresis: 2006; 27 4158 4165 (Pubitemid 44794907)
157. Imura Y., Sato K., Yoshimura E. Micro total bioassay system for ingested substances: Assessment of intestinal absorption, hepatic metabolism, and bioactivity. Anal Chem: 2010; 82 9983 9988
158. Lavecchia T., Tibuzzi A., Giardi M. Biosensors for functional food safety and analysis. In: Giardi M., Rea G., Berra B. editors Bio-farms for nutraceuticals, Vol 698. Advances in experimental medicine and biology. Berlin, Heidelberg Springer: 2010; 267 281
159. Andreescu S., Sadik O. A. Correlation of analyte structures with biosensor responses using the detection of phenolic estrogens as a model. Anal Chem: 2003; 76 552 560 (Pubitemid 38166557)
160. Dumbrepatil A. B., Lee S. G., Chung S. J., Lee M. G., Park B. C., Kim T. J., Woo E. J. Development of a nanoparticle-based FRET sensor for ultrasensitive detection of phytoestrogen compounds. Analyst: 2010; 135 2879 2886
161. Liang K., Yang L., Xiao Z., Huang J. A bipartite recombinant yeast system for the identification of subtype-selective estrogen receptor ligands. Mol Biotechnol: 2009; 41 53 62
162. Carmon K. S., Baltus R. E., Luck L. A. A biosensor for estrogenic substances using the quartz crystal microbalance. Anal Biochem: 2005; 345 277 283 (Pubitemid 41375957)
163. Shinomiya K., Kabasawa Y., Nakazawa H., Ito Y. Countercurrent chromatographic separation of soybean isoflavones by two different types of coil planet centrifuges with various two-phase solvent systems. J Liq Chromatogr Relat Technol: 2003; 26 3497 3509 (Pubitemid 38018363)
164. Yanga F., Mab Y., Ito Y. Separation and purification of isoflavones from a crude soybean extract by high-speed counter-current chromatography. J Chromatogr A: 2001; 928 163 170 (Pubitemid 32822784)
165. Feng Z. F., Chen X. F., Zhang J., Di D. L. Activity-screening-guided isolation and purification for vasodilative effects compounds from Radix Astragali by high-speed counter-current chromatography using gradient elution. Nat Prod Res [in press]
166. Ma C. J., Li G. S., Zhang D. L., Liu K., Fan X. One step isolation and purification of liquiritigenin and isoliquiritigenin from Glycyrrhiza uralensis Risch. using high-speed counter-current chromatography. J Chromatogr A: 2005; 1078 188 192 (Pubitemid 40813114)
167. Zhang T., Cao X., Han X. Preparation of national certified reference materials of active compounds from natural products by CCC. J Liq Chromatogr Relat Technol: 2003; 26 1565 1577 (Pubitemid 36790914)
168. Sil Lee Y., Ha Kim S., Kyu Kim J., Shin H. K., Kang Y. H., Yoon Park J. H., Lim S. S. Rapid identification and preparative isolation of antioxidant components in licorice. J Sep Sci: 2010; 33 664 671
169. Chen Q. H., Fu M. L., Chen M. M., Liu J., Liu X. J., He G. Q., Pu S. C. Preparative isolation and purification of xanthohumol from hops (Humulus lupulus L.) by high-speed counter-current chromatography. Food Chem: 2012; 132 619 623
170. Renault J. H., Voutquenne L., Caron C., Zeches-Hanrot M., Berwanger S., Becker H. Purification of xanthohumol from Humulus lupulus by centrifugal partition chromatography using an original acetone based solvent scale. J Liq Chromatogr Relat Technol: 2006; 29 761 771 (Pubitemid 43323293)
171. Chu X., Sun A., Liu R. Preparative isolation and purification of five compounds from the Chinese medicinal herb Polygonum cuspidatum Sieb. et Zucc by high-speed counter-current chromatography. J Chromatogr A: 2005; 1097 33 39 (Pubitemid 41628141)
172. Bisson J., Poupard P., Pawlus A. D., Pons A., Darriet P., Mérillon J. M., Waffo-Téguo P. Development of hybrid elution systems for efficient purification of stilbenoids using centrifugal partition chromatography coupled to mass spectrometry. J Chromatogr A: 2011; 1218 6079 6084
173. Zga N., Papastamoulis Y., Toribio A., Richard T., Delaunay J. C., Jeandet P., Renault J. H., Monti J. P., Mérillon J. M., Waffo-Téguo P. Preparative purification of antiamyloidogenic stilbenoids from Vitis vinifera (Chardonnay) stems by centrifugal partition chromatography. J Chromatogr B: 2009; 877 1000 1004
174. Delaunay J. C., Castagnino C., Chèze C., Vercauteren J. Preparative isolation of polyphenolic compounds from Vitis vinifera by centrifugal partition chromatography. J Chromatogr A: 2002; 964 123 128 (Pubitemid 34718009)
175. Yang F., Zhang T., Ito Y. Large-scale separation of resveratrol, anthraglycoside A and anthraglycoside B from Polygonum cuspidatum Sieb. et Zucc by high-speed counter-current chromatography. J Chromatogr A: 2001; 919 443 448 (Pubitemid 32568207)
176. Abbott J. A., Medina-Bolivar F., Martin E. M., Engelberth A. S., Villagarcia H., Clausen E. C., Carrier D. J. Purification of resveratrol, arachidin-1, and arachidin-3 from hairy root cultures of peanut (Arachis hypogaea) and determination of their antioxidant activity and cytotoxicity. Biotechnol Prog: 2010; 26 1344 1351
177. Degenhardt A., Habben S., Winterhalter P. Isolation of the lignan secoisolariciresinol diglucoside from flaxseed (Linum usitatissimum L.) by high-speed counter-current chromatography. J Chromatogr A: 2002; 943 299 302 (Pubitemid 34037994)
178. Ma C. J., Li G. S., Zhang D. L., Liu K., Fan X. One step isolation and purification of liquiritigenin and isoliquiritigenin from Glycyrrhiza uralensis Risch. using high-speed counter-current chromatography. J Chromatogr A: 2005; 1078 188 192 (Pubitemid 40813114)
179. Liu H., Yuan Q., Li C. F., Huang T. X. Isolation and purification of silychristin, silydianin and taxifolin in the co-products of the silybin refined process from the silymarin by high-speed counter-current chromatography. Proce Biochem: 2010; 45 799 804
180. Engelberth A. S., Carrier D. J., Clausen E. C. Separation of silymarins from milk thistle (Silybum marianum L.) extracted with pressurized hot water using fast centrifugal partition chromatography. J Liq Chromatogr Relat Technol: 2008; 31 3001 3011
181. Qizhen D., Weijian C., Ito Y. Preparative separation of fruit extract of Silybum marianum using a high-speed countercurrent chromatograph with scale-up columns. J Liq Chromatogr Relat Technol: 2002; 25 2515 2520