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(−)-Epigallocatechin gallate (EGCG), which is the most abundant bitter polyphenol in green tea (Camellia sinensis) leaves, is generally unstable under oxidative conditions. In this study, the efficient dimerization of EGCG was successfully achieved without changes in stereochemistry by treatment with nonthermal dielectric barrier discharge (DBD) plasma. The stereochemically pure dimers 2 and 3 connected by a methylene linkage exhibited significantly enhanced melanogenesis inhibitory activities compared to the parent EGCG and the active compounds 2 and 3 suppressed cellular tyrosinase, tyrosinase-related protein (TRP)-1, and TRP-2 expression in B16F10 melanoma cells, which could be considered one of the mechanisms of action. These results indicate a new method for efficient dimerization of stereochemically active depigment agent induced by DBD plasma treatment.

A new facile method was developed for simple green synthesis of methylene-bridged phloroglucinol oligomers using nonthermal dielectric barrier discharge (DBD) plasma in methanolic solution. The chemical structures of these newly generated oligomers 2-5 were determined by interpretation of the spectroscopic data, and the inhibitory activity toward α-glucosidase of all isolates was evaluated. The unusual phloroglcuinol pentamer 5 connected by four methylene linkages showed a much higher potential inhibitory effect against α-glucosidase than the other generated oligomers 2-4 and appeared to be a promising lead for development as a potential antidiabetic agent. Abbreviations: T2DM, type2 diabetes mellitus; DBD, dielectric barrier discharge; HPLC, high-performance liquid chromatography; IC50, 50% inhibition concentration; NMR, nuclear magnetic resonance; FABMS, fastatom bombardment mass spectrometry.

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A series of novel ()-epigallocatechin gallate (EGCG)-phloroglucinol hybrid compounds 1-4 has been successfully synthesized by employing a simple and efficient methodology using a dielectric barrier discharge (DBD) plasma irradiation. The new hybrid structures were determined by interpretation of spectroscopic data, with the absolute configurations being established by analysis of the circular dichroism (CD) spectra. The novel hybrids 1 and 2 showed highly improved anti-adipogenic potencies toward both pancreatic lipase and preadipocytes differentiation in 3T3-L1 compared to the original EGCG and phloroglucinol. A novel hybrid 1 represent an interesting subclass of anti-adipogenic candidates that need further research.