Exploring Glycosylated Soy Isoflavones Affinities toward G‐tetrads as Studied by Survival Yield Method

Isoflavone glucosides in soy-based food supplements form adducts with guanosine tetrads and deoxyguanosine tetrads (G-tetrads). The adducts are analyzed by using electrospray ionization-collision induced dissociation-mass spectrometry and survival yields. The determined values of E_com50 of the adducts allow rating of the relative affinities of isoflavone glucosides toward G-tetrads.

Abstract

Taking soy-based food supplements for menopausal symptoms by women may reduce the risk of cancer. Therefore, the interaction between nucleic acids (or their constituents) and ingredients of the supplements, e. g., isoflavone glucosides, on the molecular level, has been of interest with respect to cancer therapy. In this work, the interaction between isoflavone glucosides and G-tetrads, namely [4G+Na]⁺ ions (G stands for guanosine or deoxyguanosine), were analyzed by using electrospray ionization-collision induced dissociation-mass spectrometry (ESI-CID-MS) and survival yields method. The strength of isoflavone glucosides-[4G+Na]⁺ interaction in the gas phase was determined from E_com50 – the energy required to fragment 50 % of selected precursor ions. Glycitin-[4G+Na]⁺ interaction was found to be the strongest, and the interaction between isoflavone glucosides and guanosine tetrad was established to be stronger than that between isoflavone glucosides and deoxyguanosine tetrad.

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