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This work describes a green and novel approach to synthesize a lipophilic EGCG palmitate by chemical acylation of EGCG with palmitoyl chloride, and thus the significant elevated stability and bioavailability of EGCG are achieved. Various parameters affecting the acylation reaction process, such as the base, solvent, as well as the mole ratio of palmitoyl chloride have been studied, in order to optimize the acylation procedure. The compound 1 in the reaction mixture was separated by silica column chromatography. The compound 1 was confirmed by HPLC-MS and NMR and was identified as the EGCG palmitate (PEGCG). The stability of the EGCG palmitates and EGCG in different conditions were studies. Compared with EGCG, PEGCG showed better inhibition on the activities of α-amylase and α-glucosidase, with IC50 values of 1.64 and 0.22 μM, respectively. These observations open a novel and effective synthetic pathway for derivation of EGCG and suggest that the lipophilic PEGCG may act as an antidiabetic agent.

A NOVEL SYNTHESIS METHOD OF LIPOPHILIC EGCG PALMITATE AND EVALUATION FOR ITS ALPHA AMYLASE AND ALPHA GLUCOSIDASE INHIBTORY POTETIAL