Transglycosylation of naringin by Bacillus stearothermophilusMaltogenic amylase to give glycosylated naringin

J Agric Food Chem. 1999 Sep;47(9):3669-74. doi: 10.1021/jf990034u.

Abstract

Naringin, a bitter compound in citrus fruits, was transglycosylated by Bacillus stearothermophilus maltogenic amylase reaction with maltotriose to give a series of mono-, di-, and triglycosylnaringins. Glycosylation products of naringin were observed by TLC and HPLC. The major glycosylation product was purified by using a Sephadex LH-20 column. The sturcture was determined by using MALDI-TOF MS, methylation analysis, and (1)H and (13)C NMR. The major transglycosylation product was maltosylnaringin, in which the maltose unit was attached by an alpha-1-->6 glycosidic linkage to the D-glucose moiety of naringin. This product was 250 times more soluble in water and 10 times less bitter than naringin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / metabolism*
  • Carbohydrate Sequence
  • Citrus
  • Flavanones*
  • Flavonoids / chemistry
  • Flavonoids / metabolism*
  • Geobacillus stearothermophilus / enzymology*
  • Glycoside Hydrolases / metabolism*
  • Glycosylation
  • Molecular Sequence Data
  • Oligosaccharides / chemistry

Substances

  • Antioxidants
  • Flavanones
  • Flavonoids
  • Oligosaccharides
  • Glycoside Hydrolases
  • glucan 1,4-alpha-maltohydrolase
  • naringin