Further study on the 1,4-alpha-transglucosylation of rubusoside, a sweet steviol-bisglucoside from Rubus suavissimus.
Rubusoside (the beta-D-glucosyl ester of 13-O-beta-D-glucosyl-steviol), which is the major sweet principle of leaves of Rubus suavissimus S. Lee, was subjected to 1,4-alpha-transglucosylation by the cyclodextringlucanotransferase-starch system (the CGTase system). The tri- and tetra-glucosylated products were isolated together with the mono- and di-glucosylated products, which had already been isolated. A prominent increase in intensity of the sweetness was observed for the compounds which were di- and tri-glucosylated at the 13-O-glucosyl moiety. This result further substantiated the structure-sweetness relationship for 1,4-alpha-glucosylated compounds of steviol-glycosides reported previously. For protection of the 19-COO-glucosyl moiety against glucosylation by the CGTase system, the 4-hydroxyl group of the 19-COO-glucosyl moiety was beta-galactosylated by the beta-galactosidase-lactose system. This galactosylated compound was subjected to a regio-selective glucosylation of the 13-O-glucosyl moiety by the CGTase system, which was followed by enzymic elimination of the galactosyl group to furnish an exclusive preparation of the improved sweeteners just mentioned.
Ohtani
K
K
Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Japan.
Aikawa
Y
Y
Ishikawa
H
H
Kasai
R
R
Kitahata
S
S
Mizutani
K
K
Doi
S
S
Nakaura
M
M
Tanaka
O
O
D002240:Carbohydrate Sequence; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification; D045786:Diterpenes, Kaurane; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification; D006031:Glycosylation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010945:Plants, Edible / Q000032:analysis; D013549:Sweetening Agents / Q000737:chemistry / Q000302:isolation & purification
D004224:Diterpenes; D045786:Diterpenes, Kaurane; D005960:Glucosides; D013549:Sweetening Agents; C056177:rubusoside