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Phloretin-4- O -β-D-glucopyranoside ( 1 ), isolated from  Homalium stenophyllum , was synthesized for the first time through aldol condensation and Schmidt glycosylation reactions aiming to develop a novel hydrophilic tyrosinase inhibitor. However, the specific rotation of synthetic  1  was found to be negative and different from that reported for natural product  1 . Thus, L-glucoside  2  was chemically synthesized using the established synthetic route of  1 , suggesting that the configuration of the natural product  1  was the same as that of  2 , as their specific rotation and spectroscopic data were also the same. In addition, the evaluation of the inhibitory activity of  1  and  2  against tyrosinase indicated that  2  was 1.4 times more potent than  1 , but they were both relatively weak. Therefore, the enantiomeric analogues  1  and  2  were proved to be unique tyrosinase inhibitors due to the chiral recognition from the tyrosinase active site.

Synthesis, structural revision, and tyrosinase inhibitory activity of proposed phloretin-4-O-β-D-glucopyranoside from Homalium stenophyllum