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Synthesis and antityrosinase, antioxidant activities of phloretin thiosemicarbazones

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Abstract

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.

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Acknowledgment

This work was supported by the Natural Science Foundation of China (No. 20962014).

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Authors and Affiliations

  1. State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang, 330047, Jiangxi, People’s Republic of China

    Binbin Xu, Pinghong Wan & Shuwen Cao

  2. Department of Chemistry, Nanchang University, Nanchang, 330031, Jiangxi, People’s Republic of China

    Yanying Yu & Shuwen Cao

  3. College of Agronomy, Jiangxi Agricultural University, Nanchang, 330045, Jiangxi, People’s Republic of China

    Chunpeng Wan

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  1. Binbin Xu
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Correspondence to Yanying Yu.

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Xu, B., Yu, Y., Wan, P. et al. Synthesis and antityrosinase, antioxidant activities of phloretin thiosemicarbazones. Res Chem Intermed 40, 3095–3107 (2014). https://doi.org/10.1007/s11164-013-1154-8

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  • DOI: https://doi.org/10.1007/s11164-013-1154-8

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