Transglycosylation of naringin by Bacillus stearothermophilus maltogenic amylase to give glycosylated naringin

Naringin, a bitter compound in citrus fruits, was transglycosylated by Baci llus stearothermophilus maltogenic amylase reaction with maltotriose to giv e 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 structure was determined by using MALDI-TOF MS, methylation analysis, and H-1 and C-13 NMR. The maj or transglycosylation product was maltosylnaringin, in which the maltose un it was attached by an alpha-1 --> 6 glycosidic linkage to the D-glucose moi ety of naringin. This product was 250 times more soluble in water and 10 ti mes less bitter than naringin.