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This paper presents lipophilicity and bio-mimetic properties determination of 15 phytoestrogens, namely: biochanin A, daidzein, formononetin, genistein, genistein-4,7-dimethylether, prunetin, 3,4,7-trihydroxyisoflavon, 4,6,7-trihydroxyisoflavon, 4,6,7-trimethoxyisoflavon, daidzin, genistin, ononin, sissotrin, coumestrol, coumestrol dimethylether. High performance liquid chromatography (HPLC) with fast gradient elution and Caco-2 cell line were used to determine physicochemical properties of selected phytoestrogens. Lipophilicity was determined on octadecyl-sylane (ODS) stationary phase using pH 2.0 and pH 7.4 buffers. Immobilized artificial membrane (IAM) chromatography was used for prediction of interaction with biological membranes. Protein binding was measured on human serum albumin (HSA) and alpha-1-acid-glycoprotein (AGP) stationary phases. Caco-2 assay was used as a golden standard for assessing in vitro permeability. Obtained results differentiate phytoestrogens according to their structure where aglycones show significantly higher lipophilicity, IAM partitioning, AGP binding and Caco-2 permeability comparing to glucosides. However, HSA binding was very high for all investigated compounds. Furthermore, a good correlation between experimentally obtained chromatographic parameters and in silico prediction was obtained for lipophilicity and HSA binding, while the somewhat greater difference was obtained for AGP binding and Caco-2 permeability.
This article was published in the following journal.
Name: Biomedical chromatography : BMC
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