Enzymatic synthesis of glucoside derivatives of validamine and valienamine.
alpha- And beta-glucoside derivatives of validamine and valienamine were prepared by enzymatic transglucosidation using alpha- and beta-glucosidase of Rhodotorula lactosa. The structures of these derivatives have been elucidated by 13C- and 1H-nuclear magnetic resonance spectral analysis. Thus, 7-alpha-glucoside, 7-alpha-isomaltoside, and 4-alpha-glucoside of validamine and 7-alpha-glucoside, 7-alpha-isomaltoside, 4-alpha-glucoside, and 4-alpha-isomaltoside of valienamine were obtained from maltose and validamine or valienamine using alpha-glucosidase. 7-beta-glucoside, 2-beta-glucoside, and 4-beta-glucoside of validamine or valienamine were obtained from cellobiose and validamine or valienamine using beta-glucosidase. These derivatives were tested for alpha-glucosidase inhibitory activity on rat small intestinal glycosidases.
Furumoto
T
T
Faculty of Pharmacy, Hokuriku University, Ishikawa, Japan.
Kameda
Y
Y
Matsui
K
K
D000818:Animals; D053138:Cyclohexenes; D005960:Glucosides / Q000138:chemical synthesis; D065089:Glycoside Hydrolase Inhibitors; D006595:Hexosamines / Q000138:chemical synthesis*; D066298:In Vitro Techniques; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D008297:Male; D008871:Microvilli / Q000201:enzymology / Q000378:metabolism; D051381:Rats; D017208:Rats, Wistar
D053138:Cyclohexenes; D005960:Glucosides; D065089:Glycoside Hydrolase Inhibitors; D006595:Hexosamines; C042908:validamine; C030791:valienamine; D007294:Inositol