Novel aldose reductase inhibitory and antioxidant chlorogenic acid derivatives obtained by heat treatment of chlorogenic acid and amino acids

• Published in: Food chemistry 2018-11, Vol.266, p.449-457
• Main Authors: Hwang, Seung Hwan, Zuo, Guanglei, Wang, Zhiqiang, Lim, Soon Sung
• Format: Article
• Language: English
• Subjects: Aldehyde Reductase - antagonists & inhibitors; Aldehyde Reductase - metabolism; Aldose reductase; Amino Acids - chemistry; Animals; Antioxidant; Antioxidants - chemistry; Chlorogenic acid; Chlorogenic Acid - chemistry; Chlorogenic Acid - metabolism; Glutamic acid; Heating model system; Humans; Inhibitory Concentration 50; Kinetics; Lens, Crystalline - enzymology; Magnetic Resonance Spectroscopy; Molecular Conformation; Rats; Recombinant Proteins - chemistry; Recombinant Proteins - metabolism
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/j.foodchem.2018.06.053

•The newly produced compounds from the CGA-GT heating model system were isolated and characterized.•The novel CGA derivative showed high in vitro ABTS+ and DPPH radical scavenging activities and aldose reductase inhibitory activity.•Heating CGA as well as coffee bean with glutamic acid in water may contribute to functional ingredients for treatment of diabetic complications. A heating model system (HMS) of chlorogenic acid (CGA) and 20 amino acids was produced by heating at 120 °C for 4 h and evaluated for in vitro antioxidant and aldose reductase (AR). The CGA-glutamic acid (GT) HMS showed high in vitro antiradical activity indicated by ABTS+ (82.37%) and DPPH radical scavenging (83.21%) as well as AR (83.21%) inhibition. The structure of the new compound was established by NMR spectroscopy, as methyl-3-(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylate (1) and 4-O-caffeoylquinic acid (2) from the CGA-GT HMS. The IC50 values of compound 1 for ABTS+, DPPH and AR were 8.21, 56.97 and 3.68 μM, respectively. These activities were similar to or higher than those of known positive controls (5.49, 63.58 and 13.60 μM). We suggest that heat treatment generates novel CGA-GT HMS with increased antioxidant and AR inhibitory effects and contributes to the development of novel functional materials from CGA food products.