Enzymic production of sweet stevioside derivatives: transglucosylation by glucosidases.
For the purpose of improving sweetness and a further study on the structure-sweetness relationship of steviol glycosides, transglycosylation of stevioside by a variety of commercial glucosidases was investigated. It was revealed that two alpha-glucosidases gave glucosylated products. Transglucosylation of stevioside by Pullulanase and pullulan exclusively afforded three products, 13-O-[beta-maltotriosyl-(1----2)-beta-D-glucosyl]-19-O-beta-D-g luc osyl- steviol (1), 13-O-[beta-maltosyl-(1----2)-beta-D-glucosyl]-19-O-beta-D-glucosyl- steviol (2) and 13-O-beta-sophorosyl-19-O-beta-maltotriosyl-steviol (3). All of these products have already been obtained by trans-alpha-1,4-glucosylation of stevioside by the cyclodextrin glucanotransferase starch system, and 1 and 2 have been proven to be tasty and potent sweeteners. Transglucosylation of stevioside by Biozyme L and maltose afforded three new products, 4, 5 and 6, the structures of these compounds being elucidated as 13-O-beta-sophorosyl-19-O-beta-isomaltosyl-steviol (4), 13-O-[beta-isomaltosyl(1----2)-beta-D-glucosyl]-19-O-beta-D-glucosyl- steviol (5) and 13-O-[beta-nigerosyl-(1----2)-beta-D-glucosyl]-19-O-beta-D- glucosyl-steviol (6). A significantly high quality of taste was evaluated for 4.
Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Japan.
S V
SV
Lobov
R
R
Kasai
K
K
Ohtani
O
O
Tanaka
K
K
Yamasaki
D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D004224:Diterpenes; D045786:Diterpenes, Kaurane; D005959:Glucosidases / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis*; D006031:Glycosylation; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D013549:Sweetening Agents / Q000138:chemical synthesis*; D013729:Terpenes / Q000138:chemical synthesis*
D004224:Diterpenes; D045786:Diterpenes, Kaurane; D005960:Glucosides; D013549:Sweetening Agents; D013729:Terpenes; C012043:stevioside; D005959:Glucosidases