Enzymatic Synthesis, Structural Analysis, and Evaluation of Antibacterial Activity and α-Glucosidase Inhibition of Hesperidin Glycosides

Catalysts

Prakarn Rudeekulthamrong¹  Titaporn Chaisin²  Jarunee Kaulpiboon² 

[1] Department of Biochemistry, Phramongkutklao College of Medicine, Phramongkutklao Hospital, Bangkok 10400, Thailand;Protein Research Laboratory, Division of Biochemistry, Department of Pre-Clinical Science, Faculty of Medicine, Thammasat University, Pathumthani 12120, Thailand;

关键词: chemical structure;    cyclodextrin glycosyltransferase;    antibacterial activity;    α-glucosidase inhibition;    hesperidin glycosides;   

DOI  :  10.3390/catal11050532

来源: DOAJ

【 摘 要 】

This study was designed to investigate the structure of synthesized hesperidin glycosides (HGs) and evaluate their antibacterial and α-glucosidase inhibitory activities. The preliminary structure of HG_s was confirmed by glucoamylase treatment and analyzed on thin layer chromatography (TLC). The LC-MS/MS profiles of HGs showed the important fragments at m/z ratios of 345.21 (added glucose to glucose of rutinose in HG₁) and 687.28 (added maltose to glucose of rutinose in HG₂), confirming that the structures of HG₁ and HG₂ were α-glucosyl hesperidin and α-maltosyl hesperidin, respectively. In addition, ¹H and ¹³C-NMR of hesperidin derivatives were performed to identify their α-1,4-glycosidic bonds. The MIC and MBC studies showed that transglycosylated HG₁ and HG₂ had better antibacterial and bactericidal activities than hesperidin and diosmin, and were more active against Staphylococcus aureus than Escherichia coli. Hesperidin, HG₁, HG₂, and diosmin inhibited α-glucosidase with IC₅₀ values of 2.75 ± 1.57, 2.48 ± 1.61, 2.36 ± 1.48, and 2.99 ± 1.23 mg/mL, respectively. The inhibition kinetics of HG₂ shown by a Lineweaver–Burk plot confirmed HG₂ was an α-glucosidase competitive inhibitor with an inhibitor constant, K_i, of 2.20 ± 0.10 mM. Thus, HGs have the potential to be developed into antibacterial drugs and treatments for treating α-glucosidase-associated type 2 diabetes.

【 授权许可】

Unknown