Biomaterial Database

Direct and indirect photolysis of the phytoestrogens genistein and daidzein. 2012

Megan M Kelly, and William A Arnold

Water Resources Science Graduate Program, University of Minnesota, 1985 Buford Avenue, St. Paul, Minnesota 55108, USA.

Genistein and daidzein are two estrogenic compounds derived from plants, especially legumes. This research begins to explore their environmental fate, focusing on direct and indirect photolysis. UV-visible spectra for both compounds at varying pH values were taken, the pK(a) values for both compounds were measured, and UV-visible spectra for each protonation state were determined. The loss of both compounds in deionized water was observed upon exposure to natural sunlight, and the quantum yields were determined for each protonation state. In Mississippi River water, direct photolysis does not account for all of the loss of genistein and daidzein. The mechanism of indirect photolysis was probed using quenchers and sensitizers, and results suggest that daidzein is transformed mainly via direct photolysis and singlet oxygenation, while genistein is transformed mainly via reaction with triplet-state natural organic matter. The parameters determined in this study will allow for estimation of the concentration of genistein and daidzein in sunlit surface waters, which will allow for assessment of any risks posed to aquatic wildlife.

UI	MeSH Term	Description	Entries
D007529	Isoflavones	3-Phenylchromones. Isomeric form of FLAVONOIDS in which the benzene group is attached to the 3 position of the benzopyran ring instead of the 2 position.	3-Benzylchroman-4-One,3-Benzylidene-4-Chromanone,Homoisoflavone,Homoisoflavones,Isoflavone,Isoflavone Derivative,3-Benzylchroman-4-Ones,3-Benzylidene-4-Chromanones,Isoflavone Derivatives,3 Benzylchroman 4 One,3 Benzylchroman 4 Ones,3 Benzylidene 4 Chromanone,3 Benzylidene 4 Chromanones,Derivative, Isoflavone,Derivatives, Isoflavone
D007700	Kinetics	The rate dynamics in chemical or physical systems.
D008922	Mississippi	State bounded on the north by Tennessee, on the east by Alabama, on the south by Louisiana and Gulf of Mexico, and on the west by Arkansas and Louisiana.
D010782	Photolysis	Chemical bond cleavage reactions resulting from absorption of radiant energy.	Photodegradation
D011522	Protons	Stable elementary particles having the smallest known positive charge, found in the nuclei of all elements. The proton mass is less than that of a neutron. A proton is the nucleus of the light hydrogen atom, i.e., the hydrogen ion.	Hydrogen Ions,Hydrogen Ion,Ion, Hydrogen,Ions, Hydrogen,Proton
D011789	Quantum Theory	The theory that the radiation and absorption of energy take place in definite quantities called quanta (E) which vary in size and are defined by the equation E	Quantum Theories,Theories, Quantum,Theory, Quantum
D005663	Furans	Compounds with a 5-membered ring of four carbons and an oxygen. They are aromatic heterocycles. The reduced form is tetrahydrofuran.	Tetrahydrofurans
D006207	Half-Life	The time it takes for a substance (drug, radioactive nuclide, or other) to lose half of its pharmacologic, physiologic, or radiologic activity.	Halflife,Half Life,Half-Lifes,Halflifes
D006863	Hydrogen-Ion Concentration	The normality of a solution with respect to HYDROGEN ions; H+. It is related to acidity measurements in most cases by pH	pH,Concentration, Hydrogen-Ion,Concentrations, Hydrogen-Ion,Hydrogen Ion Concentration,Hydrogen-Ion Concentrations
D013056	Spectrophotometry, Ultraviolet	Determination of the spectra of ultraviolet absorption by specific molecules in gases or liquids, for example Cl2, SO2, NO2, CS2, ozone, mercury vapor, and various unsaturated compounds. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	Ultraviolet Spectrophotometry