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

Abstract

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.

Keywords::

• Maillard reaction
• hesperidin epimers
• hesperetin enantiomers
• monoglucosyl hesperidin

Acknowledgements

The authors thank Hayashibara Biochemical Laboratories, Inc. for supply of monoglucosyl hesperidin and Akita Konno Co., Ltd. for supply of part of experimental materials.

Declaration of interest

This work was financially supported in part by a fund from the Institute for Fermentation, Osaka (IFO), Japan.