Protective effects of hesperidin derivatives and their stereoisomers against advanced glycation end-products formation

Context: Maillard reaction is implicated in the development of pathophysiology in age-related diseases. The search for newer Maillard reaction inhibitors is a priority among strategies to combat diabetes complications. Objective: To evaluate the inhibitory potential of hesperidin, its derivatives and their stereoisomers against advanced glycation end-products (AGEs) formation. Materials and methods: Hesperidin and hesperetin were chirally separated and the inhibitory effects of 1: 1 mixture of (2S)- and (2R)-hesperidin (1), (2S)-hesperidin (2), (2R)-hesperidin (3), 1: 1 mixture of (S)-and (R)-hesperetin (4), (S)-hesperetin (5), (R)-hesperetin (6), and monoglucosyl hesperidin (7) [ 1: 1 mixture of (2S)-glucosyl hesperidin (8) and (2R)-glucosyl hesperidin (9)] at a concentration of 1 mM on protein glycation reaction have been revealed using the newly constructed RNase A-methylglyoxal (MGO) assay for the early stage and the bovine serum albumin (BSA)-glucose assay for the late stage of Maillard reaction. Results: This study has demonstrated that hesperidin and its derivatives possessed relatively strong activity against the formation of AGEs. (S)-Hesperetin (5) possessed the highest inhibitory rate up to 57.4% in BSA-glucose assay, 38.2% in RNase A-MGO assay. Discussion and conclusion: The new RNase A-MGO assay system could be used for the screening of AGEs inhibitors and hesperidin, and its derivatives could be promising candidate adjuvants for the treatment of diabetes complication, and age-related chronic diseases.