Synthesis of a novel vitamin E derivative, 2-(alpha-D-glucopyranosyl) methyl-2,5,7,8-tetramethylchroman-6-ol, by alpha-glucosidase-catalyzed transglycosylation.
A novel derivative of vitamin E, vitamin E glucoside, was synthesized from 2-hydroxymethyl-2,5,7,8-tetramethylchroman-6-ol and maltose in a solution containing DMSO by transglycosylation with alpha-glucosidase from Saccharomyces species. The glycosylated product was identified as 2-(alpha-D-glucopyranosyl)methyl-2,5,7,8-tetramethylchroman-6-ol (TMG) by mass spectrometry and nuclear magnetic resonance spectroscopy. The optimal pH of transglycosylation was 5.5, and the yield of TMG increased as the concentration of maltose increased. TMG has high solubility in water (> 1 x 10(3) mg/mL). The 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity of TMG was found to be nearly the same as those of alpha-tocopherol, Trolox (2-carboxy-2,5,7,8-tetramethylchroman-6-ol), and ascorbic acid.
Murase
H
H
United Graduate School of Agricultural Sciences, Gifu University, Japan.
Yamauchi
R
R
Kato
K
K
Kunieda
T
T
Terao
J
J
D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology; D015764:Bepridil / Q000031:analogs & derivatives / Q000378:metabolism; D001713:Biphenyl Compounds; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006031:Glycosylation; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008320:Maltose / Q000378:metabolism; D015394:Molecular Structure; D010851:Picrates; D012440:Saccharomyces / Q000201:enzymology; D012995:Solubility; D014810:Vitamin E / Q000031:analogs & derivatives*; D000520:alpha-Glucosidases / Q000378:metabolism*
C106323:2-(glucopyranosyl)methyl-2,5,7,8-tetramethylchroman-6-ol; D000975:Antioxidants; D001713:Biphenyl Compounds; D002839:Chromans; D016166:Free Radical Scavengers; D006027:Glycosides; D010851:Picrates; D014810:Vitamin E; D008320:Maltose; D015764:Bepridil; C004931:1,1-diphenyl-2-picrylhydrazyl; D000520:alpha-Glucosidases