New acylated cyanidin glycosides extracted from underutilized potential sources: Enzymatic synthesis, antioxidant activity and thermostability

Food Chem. 2020 Mar 30:309:125796. doi: 10.1016/j.foodchem.2019.125796. Epub 2019 Oct 26.

Abstract

Interest in anthocyanins has increased remarkably in recent decades, although their wider application has been hampered by instability problems. Thus, this study aimed at developing a strategy to gain access to more stable anthocyanins via enzymatic esterification. For that purpose, three cyanidin derivatives were obtained from underutilized, but easily accessible sources, and their total anthocyanin content was quantified. The purity of cyanidins obtained ranged from 40% to 88% depending on their source. Subsequently, the critical enzymatic reaction conditions were established, and the best results were found using tert-butanol as a solvent, 20 g/L of lipase B from Candida Antarctica, and vinyl cinnamate as acyl donor at ratio 250:1 (acyl donor to anthocyanin). Finally, five new acylated anthocyanin derivatives were synthesized with improved antioxidant activity and thermostability, in comparison to the cyanidin-3-glucoside, which is an advantageous feature for industrial applications.

Keywords: Acylated anthocyanin; Dihydrocinnamic acids; Enzymatic esterification; Lipases.

MeSH terms

  • Acylation
  • Anthocyanins / chemistry
  • Anthocyanins / metabolism*
  • Antioxidants / chemistry*
  • Cinnamates / chemistry
  • Esterification
  • Fungal Proteins / metabolism*
  • Glucosides / chemistry
  • Glucosides / metabolism*
  • Lipase / metabolism*
  • Magnetic Resonance Spectroscopy
  • Prunus domestica / chemistry
  • Prunus domestica / metabolism
  • Solvents / chemistry
  • Temperature

Substances

  • Anthocyanins
  • Antioxidants
  • Cinnamates
  • Fungal Proteins
  • Glucosides
  • Solvents
  • cyanidin-3-O-beta-glucopyranoside
  • Lipase
  • lipase B, Candida antarctica