Hydroxy methoxy benzaldehyde from Sesbania grandilfora inhibits the advanced glycation end products (AGEs)-mediated fibrillation in hemoglobin

J Biomol Struct Dyn. 2018 Mar;36(4):819-829. doi: 10.1080/07391102.2017.1300543. Epub 2017 Mar 20.

Abstract

The present study was aimed to identify the active anti-glycation constituent from the leaves of Sesbania grandiflora. Characterization of the active constituent resulted in the identification of hydroxy methoxy benzaldehyde (HMB). The potential of HMB as anti-glycation lead was analyzed by fluorescence spectroscopy, fluorescence microscopy, scanning electron microscopy (SEM) and molecular interaction studies. Our results suggested that HMB inhibited formation of early (HbA1c) and advanced glycation end products (AGEs). The amyloid-like fibrillation in hemoglobin was also inhibited by HMB. SEM images indicated the protective effect against the formation of acanthocytes. Molecular docking studies showed that HMB was interacting with hemoglobin through hydrogen bonds with Arg141, Tyr140, and Thr137. Our findings suggest that HMB could be a better anti-glycation lead molecule towards novel AGEs inhibitors.

Keywords: HbA1c; advanced glycation end products; amyloid fibrils; fluorescence microscopy; glycation; hemoglobin; red blood cells.

MeSH terms

  • Benzaldehydes / chemistry*
  • Benzaldehydes / isolation & purification
  • Benzaldehydes / pharmacology*
  • Diabetes Mellitus / drug therapy*
  • Diabetes Mellitus / pathology
  • Glycated Hemoglobin / antagonists & inhibitors
  • Glycated Hemoglobin / chemistry
  • Glycation End Products, Advanced / antagonists & inhibitors
  • Glycation End Products, Advanced / chemistry
  • Glycosylation / drug effects
  • Hemoglobins / antagonists & inhibitors
  • Hemoglobins / chemistry
  • Humans
  • Hydrogen Bonding / drug effects
  • Molecular Docking Simulation
  • Plant Leaves / chemistry
  • Sesbania / chemistry*
  • Spectrometry, Fluorescence

Substances

  • Benzaldehydes
  • Glycated Hemoglobin A
  • Glycation End Products, Advanced
  • Hemoglobins