ABSTRACT
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.
Subject(s)
Genistein/radiation effects , Isoflavones/radiation effects , Photolysis/radiation effects , Phytoestrogens/radiation effects , Ultraviolet Rays , Furans/chemistry , Genistein/chemistry , Half-Life , Hydrogen-Ion Concentration , Hydroxyl Radical/chemistry , Isoflavones/chemistry , Kinetics , Mississippi , Phytoestrogens/chemistry , Protons , Quantum Theory , Rivers/chemistry , Singlet Oxygen/chemistry , Spectrophotometry, UltravioletABSTRACT
Photosensitized compounds from daidzein were studied in a riboflavin model system under visible light irradiation by high-performance liquid chromatography (HPLC). As the period of light irradiation increased, concentration of daidzein decreased significantly (P < 0.05) and new peaks of daidzein derivatives were observed and changed during photosensitization. Three new peaks from photosensitized daidzein were tentatively identified as 7-, 3', 4'-trihydroxyisoflavone (or 3'-hydroxydaidzein) and 2 dimmers of daidzein by a combination of HPLC-mass spectrometry (MS) and retention times of standard compounds by HPLC. Addition of sodium azide and removal of headspace oxygen treatment affected the formation of newly formed peaks. The type I pathway of riboflavin photosensitization played more important roles than type II pathways on the formation of daidzein derivatives. Practical Application: Isoflavones are important phytochemicals found in soy foods. Generally, many foods containing soy ingredients are displayed under visible light irradiation. Also, riboflavin can be found in many foods containing vegetables. The results of this study can be used to understand the stability and changes of isoflavone aglycones in soy and soy-based foods under visible light irradiation.
Subject(s)
Isoflavones/chemistry , Isoflavones/radiation effects , Light , Photosensitizing Agents/chemistry , Riboflavin/chemistry , Soy Foods/radiation effects , Chromatography, High Pressure Liquid , Dimerization , Free Radical Scavengers/chemistry , Isoflavones/analysis , Models, Chemical , Osmolar Concentration , Oxidation-Reduction/drug effects , Oxidation-Reduction/radiation effects , Oxygen/chemistry , Singlet Oxygen/antagonists & inhibitors , Sodium Azide/chemistry , Soy Foods/analysis , Spectrometry, Mass, Electrospray Ionization , Time FactorsABSTRACT
Plant derived phytochemicals have been the focus of recent research due to their health promoting effects. Previous studies to estimate the levels of these bioactive compounds made use of traditional solvent extraction procedures such as homogenization and soxhlet (reflux) methods. Recently, the ultrasonication technique has been shown to be an efficient non-thermal extraction method. The objective of this study was to investigate the effect of frequency and duration (time) of sonication on the extraction efficiency of selected phytochemicals from peanuts and to determine optimal conditions (sample-to-solvent ratio, frequency, and time) for their extraction. The results obtained showed that sample-to-solvent ratio, frequency, and duration of sonication had significant effect on the extraction efficiency of the phytochemicals from peanut. Sonication at 80 kHz facilitated the extraction of biochanin A and trans-resveratrol while 25 kHz was effective in the extraction of daidzein and genistein. Multi-frequency extractions were more efficient than single frequency.