Transglycosylation of Naringin by Bacillus stearothermophilus Maltogenic Amylase To Give Glycosylated Naringin

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 1H and 13C NMR. The major transglycosylation product was maltosylnaringin, in which the maltose unit was attached by an α-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. Keywords: Naringin; maltogenic amylase from Bacillus stearothermophilus; maltosylnaringin; transglycosylation