Enzyme-assisted modification of flavonoids from Matricaria chamomilla: antioxidant activity and inhibitory effect on digestive enzymes

J Enzyme Inhib Med Chem. 2020 Dec;35(1):42-49. doi: 10.1080/14756366.2019.1681989.

Abstract

Matricaria chamomilla L. contains antioxidant flavonoids that can have their bioactivity enhanced by enzymatic hydrolysis of specific glycosyl groups. This study implements an untargeted metabolomics approach based on ultra-performance liquid chromatography coupled with electrospray ionisation quadrupole time-of-flight mass spectrometry technique operating in MSE mode (UPLC-QTOF-MSE) and spectrophotometric analysis of chamomile aqueous infusions, before and after hydrolysis by hesperidinase and β-galactosidase. Several phenolic compounds were altered in the enzymatically treated infusion, with the majority being flavonoid derivatives of apigenin, esculetin, and quercetin. Although enzymatically modifying the infusion only led to a small increase in antioxidant activity (DPPH method), its inhibitory effect on pancreatic lipase was of particular interest. The enzymatically treated infusion exhibited a greater inhibitory effect (EC50 of 35.6 µM) than unmodified infusion and kinetic analysis suggested mixed inhibition of pancreatic lipase. These results are of great relevance due to the potential of enzymatically treated functional foods in human health.

Keywords: flavonoids; hesperidinase; β-galactosidase.

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / metabolism
  • Antioxidants / pharmacology*
  • Biphenyl Compounds / antagonists & inhibitors
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / metabolism
  • Enzyme Inhibitors / pharmacology*
  • Flavonoids / chemistry
  • Flavonoids / metabolism
  • Flavonoids / pharmacology*
  • Glycoside Hydrolases / metabolism
  • Humans
  • Hydrolysis
  • Lipase / antagonists & inhibitors*
  • Lipase / metabolism
  • Matricaria / chemistry*
  • Matricaria / metabolism
  • Metabolomics
  • Molecular Structure
  • Picrates / antagonists & inhibitors
  • Structure-Activity Relationship
  • beta-Galactosidase / metabolism

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Enzyme Inhibitors
  • Flavonoids
  • Picrates
  • 1,1-diphenyl-2-picrylhydrazyl
  • Lipase
  • Glycoside Hydrolases
  • hesperidinase
  • beta-Galactosidase

Grants and funding

This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior – Brasil (CAPES) – Finance code 001, and by FAPESP (Fundação de Amparo à Pesquisa do Estado de São Paulo), process n. 2012/20393–4. The authors also acknowledge the scholarships financed by Conselho Nacional de Desenvolvimento Científico e Tecnológico (PIBIC - CNPq).