Three phloretin derivates were achieved through condensation of the phloretin template with thiosemicarbazide, 4-methylthiosemicarbazide, and 4-phenyl-3-thiosemicarbazide. Their purity was confirmed by high-performance liquid chromatograph and their structures were determined from their ultraviolet spectra, Fourier-transform infrared, 1H and 13C NMR, and mass spectra. The solubility of these novel compounds in ultrapure water at 25 °C was significantly improved compared with that of phloretin in the following order: phloretin thiosemicarbazone (PT, >1.00 mg/mL) > phloretin-4-phenyl-3-thiosemicarbazone (PPT, 0.52 mg/mL) > phloretin-4-methylthiosemicarbazone (PMT, 0.24 mg/mL) > phloretin (0.02 mg/mL). The tyrosinase inhibitory effect and various antioxidant assays in vitro were evaluated. Results showed that PT possesses potent tyrosinase inhibitory activity (IC50 = 57.81 ± 1.46 μM), which was better than phloretin (IC50 = 70.08 ± 0.88 μM). They also significantly quenched 1,1-diphenyl-2-picryl-hydrazyl and exhibited strong activity against the lipid peroxidation induced by Fe2+/ascorbic acid. Likewise, these compounds significantly protected against 2,2′-azo-bis(2-amidinopropane)dihydrochloride-induced Cu, Zn-superoxide dismutase, and pBR322 plasmid DNA damage in a dose-dependent manner.
Research on Chemical Intermediates – Springer Journals
Published: Mar 19, 2013
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