SYNTHESIS OF NEOHESPERIDIN GLYCOSIDES AND NARINGIN GLYCOSIDES BY CYCLODEXTRIN GLUCANOTRANSFERASE FROM AN ALKALOPHILIC BACILLUS SPECIES

Cyclodextrin glucanotransferase from an alkalophilic Bacillus species produced neohesperidin monoglucoside and a series of its maltooligoglu cosides by transglycosylation with neohesperidin as an acceptor and so luble starch as a donor. As the reaction using beta-CD as a donor at a n alkaline pH was very effective for solubilizing neohesperidin, the a mount of glycosides formed was increased. As a result, its amount with beta-CD at pH 10 was about 7 times greater than that with soluble sta rch at pH 5. Neohesperidin monoglucoside was purified from the reactio n mixture by glucoamylase and naringinase treatments, an Amberlite XAD -16 column, a Sephadex LH20 column, and HPLC on an ODS column. The str ucture of the purified monoglucoside was identified as 3(G)-alpha-D-gl ucopyranosyl neohesperidin by FAB-MS, methylation analysis, and H-1- a nd C-13-NMR. The solubility of neohesperidin monoglucoside in water wa s approximately 1500 times higher than that of neohesperidin, and the bitterness of the monoglucoside was about 10 times less than that of n eohesperidin. In addition, naringin was also glycosylated by the same method as neohesperidin, and ifs monoglucoside was identified as 3(G)- alpha-D-glucopyranosyl naringin. The solubility of naringin monoglucos ide in water was also at least 1000 times higher than that of naringin without altering its bitterness.