title: Protective effects of hesperidin derivatives and their stereoisomers against advanced glycation end-products formation.
abstract: BACKGROUND
  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.
  
  
  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.
  
  
  CONCLUSIONS
  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.
authors.affiliation: Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan.
authors.forename: Daxin
authors.initials: D
authors.lastname: Li
authors.forename: Shinya
authors.initials: S
authors.lastname: Mitsuhashi
authors.forename: Makoto
authors.initials: M
authors.lastname: Ubukata
mesh_terms: D005947:Glucose / Q000378:metabolism; D005960:Glucosides / Q000494:pharmacology; D017127:Glycation End Products, Advanced / Q000378:metabolism*; D006569:Hesperidin / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology*; D057166:High-Throughput Screening Assays; D007004:Hypoglycemic Agents / Q000737:chemistry / Q000494:pharmacology*; D015416:Maillard Reaction / Q000187:drug effects; D015394:Molecular Structure; D011765:Pyruvaldehyde / Q000378:metabolism; D012259:Ribonuclease, Pancreatic / Q000378:metabolism; D012710:Serum Albumin, Bovine / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D005960:Glucosides; D017127:Glycation End Products, Advanced; D007004:Hypoglycemic Agents; D012710:Serum Albumin, Bovine; C487382:glucosyl hesperidin; D011765:Pyruvaldehyde; D006569:Hesperidin; D012259:Ribonuclease, Pancreatic; D005947:Glucose; C013015:hesperetin