T. Kometani et al., SYNTHESIS OF NEOHESPERIDIN GLYCOSIDES AND NARINGIN GLYCOSIDES BY CYCLODEXTRIN GLUCANOTRANSFERASE FROM AN ALKALOPHILIC BACILLUS SPECIES, Bioscience, biotechnology, and biochemistry, 60(4), 1996, pp. 645-649
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.