Separation optimization and quantitative analysis of phytoestrogens employing reverse-phase high-performance liquid chromatography with UV-VIS detection

References

• Dixon, R. A. Phytoestrogens. Annu. Rev. Plant Biol. 2004, 55, 225–261. DOI: 10.1146/annurev.arplant.55.031903.141729.
   PubMed Web of Science ®Google Scholar
• Bennetts, H. W.; Underwood, E. J.; Shier, F. L. A Specific Breeding Problem of Sheep on Subterranean Clover Pastures in Western Australia. Aust. Veter. J. 1946, 1, 2–12.
   Google Scholar
• Setchell, K. D. R.; Welsh, M. B.; Lim, C. K. High-performance Liquid Chromatographic Analysis of Phytoestrogens in Soy Protein Preparations with Ultraviolet, Electrochemical and Thermospray Mass Spectrometric Detection. J. Chromatogr. A. 1987, 386, 315–323. DOI: 10.1016/S0021-9673(01)94608-4.
   PubMed Web of Science ®Google Scholar
• McLachlan, J. A.; Newbold, R. R. Estrogens and Development. Environ. Health Perspect. 1987, 75, 25–27.
   PubMed Web of Science ®Google Scholar
• Cederroth, C. R.; Nef, S. Soy, Phytoestrogens and Metabolism: A Review. Mol. Cell. Endocrinol. 2009, 304, 30–42.
   PubMed Web of Science ®Google Scholar
• Burdette, C. Q.; Kenneth Marcus, R. Determination of Isoflavone Content in Soy, Red Clover, and Kudzu Dietary Supplement Materials by Liquid Chromatography-Particle Beam/Electron Ionization Mass Spectrometry. J. AOAC Int. 2013, 96, 925–932. DOI: 10.5740/jaoacint.12-431.
   PubMed Web of Science ®Google Scholar
• Li, B.; Lima, M. R. M.; Nie, Y.; Xu, L.; Liu, X.; Yuan, H.; Chen, C.; Dias, A. C. P.; Zhang, X. HPLC-DAD Fingerprints Combined with Multivariate Analysis of Epimedii Folium from Major Producing Areas in Eastern Asia: Effect of Geographical Origin and Species. Front. Pharmacol. 2021, 12, 761551. DOI: 10.3389/fphar.2021.761551.
   PubMed Web of Science ®Google Scholar
• Sivesind, E.; Seguin, P. Effects of the Environment, Cultivar, Maturity, and Preservation Method on Red Clover Isoflavone Concentration. J. Agric. Food Chem. 2005, 53, 6397–6402. DOI: 10.1021/jf0507487.
   PubMed Web of Science ®Google Scholar
• McMurray, C. H.; Laidlaw, A. S.; McElroy, M. The Effect of Plant Development and Environment on Formononetin Concentration in Red Clover (Trifolium pratense L. J. Sci. Food Agric. 1986, 37, 333–340. DOI: 10.1002/jsfa.2740370402.
   Web of Science ®Google Scholar
• Budryn, G.; Gałązka-Czarnecka, I.; Brzozowska, E.; Grzelczyk, J.; Mostowski, R.; Żyżelewicz, D.; Cerón-Carrasco, J. P.; Pérez-Sánchez, H. Evaluation of Estrogenic Activity of Red Clover (Trifolium pratense L.) Sprouts Cultivated under Different Conditions by Content of Isoflavones, Calorimetric Study and Molecular Modelling. Food Chem. 2018, 245, 324–336. 15DOI: 10.1016/j.foodchem.2017.10.100.
   PubMed Web of Science ®Google Scholar
• Saviranta, N. M.; Anttonen, M. J.; Von Wright, A.; Karjalainen, R. O. Red Clover (Trifolium pratense L.) Isoflavones: determination of Concentrations by Plant Stage, Flower Colour, Plant Part and Cultivar. J. Sci. Food Agric. 2008, 88, 125–132. DOI: 10.1002/jsfa.3056.
   Web of Science ®Google Scholar
• Duan, T.; Ma, H.; Dong, Y.; Yang, F.; Liu, X. Microemulsion Liquid Chromatographic Method for Simultaneous Separation and Determination of Five Isoflavones in Red Clover. J. Liq. Chromatogr. Relat. Technol. 2021, 44, 140–147. DOI: 10.1080/10826076.2020.1866599.
   Web of Science ®Google Scholar
• Booth, N. L.; Overk, C. R.; Yao, P.; Totura, S.; Deng, Y.; Hedayat, A. S.; Bolton, J. L.; Pauli, G. F.; Farnsworth, N. R. Seasonal Variation of Red Clover (Trifolium pratense L., Fabaceae) Isoflavones and Estrogenic Activity. J. Agric. Food Chem. 2006, 54, 1277–1282.
   PubMed Web of Science ®Google Scholar
• Marko-Varga, G.; Barceló, D. Liquid Chromatographic Retention and Separation of Phenols and Related Aromatic Compounds on Reversed Phase Columns. Chromatographia. 1992, 34, 146–154. DOI: 10.1007/BF02276128.
   Web of Science ®Google Scholar
• Steinshamn, H.; Purup, S.; Thuen, E.; Hansen-Møller, J. Effects of Clover-grass Silages and Concentrate Supplementation on the Content of Phytoestrogens in Dairy Cow Milk. J. Dairy Sci. 2008, 91, 2715–2725. DOI: 10.3168/jds.2007-0857.
   PubMed Web of Science ®Google Scholar
• Höjer, A.; Adler, S.; Purup, S.; Hansen-Møller, J.; Martinsson, K.; Steinshamn, H.; Gustavsson, A. M. Effects of Feeding Dairy Cows Different Legume-grass Silages on Milk Phytoestrogen Concentration. J. Dairy Sci. 2012, 95, 4526–4540. DOI: 10.3168/jds.2011-5226.
   PubMed Web of Science ®Google Scholar
• Tsao, R.; Papadopoulos, Y.; Yang, R.; Chris Young, J.; Mcrae, K. Isoflavone Profiles of Red Clovers and Their Distribution in Different Parts Harvested at Different Growing Stages. J. Agric. Food Chem. 2006, 54, 5797–5805. 16
   PubMed Web of Science ®Google Scholar
• Waters Technical support discussion.
   Google Scholar
• Plumb, R.; Mazzeo, J. R.; Grumbach, E. S.; Rainville, P.; Jones, M.; Wheat, T.; Neue, U. D.; Smith, B.; Johnson, K. A. The Application of Small Porous Particles, High Temperatures, and High Pressures to Generate Very High Resolution LC and LC/MS Separations. J. Sep. Sci. 2007, 30, 1158–1166.
   PubMed Web of Science ®Google Scholar
• Phillips, K. M.; Ruggio, D. M.; Ashraf-Khorassani, M. Phytosteril Composition of Nuts and Seeds Commonly Consumed in the United States. J. Agric. Food Chem. 2005, 53, 94536–99445.
   Web of Science ®Google Scholar
• Gikas, E.; Alesta, A.; Economou, G.; Karamanos, A.; Tsarbopoulos, A. Determination of Isoflavones in the Aerial Part of Red Clover by HPLC–Diode Array Detection. Journal of Liquid Chromatography & Related Technologies 2008, 31, 1181–1194. DOI: 10.1080/10826070802000723.
   Web of Science ®Google Scholar
• Krenn, L.; Unterrieder, I.; Ruprechter, R. Quantification of Isoflavones in Red Clover by High-performance Liquid Chromatography. J. Chromatogr. B. 2002, 25, 123–128. 777, 1-2,
   Google Scholar
• Lemežienė, N.; Padarauskas, A.; Butkutė, B.; Cesevičienė, J.; Taujenis, L.; Norkevičienė, E.; Norkevičienė, E. The Concentration of Isoflavones in Red Clover (Trifolium pratense L.) at Flowering Stage. Zemdirb. Agric. 2015, 102, 443–448. DOI: 10.13080/z-a.2015.102.057.
   Web of Science ®Google Scholar