Antioxidant activity of a novel vitamin E derivative, 2-(alpha-D glucopyranosyl)methyl-2,5,7,8-tetramethylchroman-6-ol.
A novel vitamin E derivative, 2-(alpha-D-glucopyranosyl)methyl-2,5,7,8-tetramethylchroman-6-ol (TMG), has excellent water-solubility (> 1 x 10[3] mg/ml). The antioxidant activity of TMG was investigated. Kinetic studies of the inhibition of radical-chain reaction of methyl linoleate in solution demonstrated that the peroxyl radical-scavenging activity was not changed by the replacement of phytiyl side chain of vitamin E to glucosyl group. TMG acted as an effective inhibitor on lipid peroxidation of egg yolk phosphatidylcholine (PC)-liposomal suspension induced by a water-soluble and a lipid-soluble radical generator, 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH) and 2,2'-azobis(2,4-dimethylvaleronitrile) (AMVN). Its effectiveness was higher than that of ascorbic acid (AsA) when liposomal suspension was exposed to a lipid-soluble radical generator, AMVN. TMG also showed an excellent antioxidant activity on cupric ion-induced lipid peroxidation of PC-liposomal suspension, and suppressed the oxidation of rat brain homogenate which contained trace level of iron ion. On the other hand, AsA acted as a prooxidant on both the cupric ion-induced liposomal peroxidation and the oxidation of rat brain homogenate. When human plasma was exposed to either AAPH or AMVN, the accumulation of cholesteryl ester hydroperoxides was retarded by the addition of TMG.
Murase
H
H
The United Graduate School of Agricultural Sciences, Gifu University, Japan.
Moon
J H
JH
Yamauchi
R
R
Kato
K
K
Kunieda
T
T
Yoshikawa
T
T
Terao
J
J
D000328:Adult; D000578:Amidines / Q000494:pharmacology; D000818:Animals; D000975:Antioxidants / Q000494:pharmacology*; D001391:Azo Compounds / Q000494:pharmacology; D002839:Chromans / Q000737:chemistry / Q000494:pharmacology*; D003300:Copper / Q000737:chemistry / Q000494:pharmacology; D016166:Free Radical Scavengers; D005609:Free Radicals; D006027:Glycosides / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007700:Kinetics; D008041:Linoleic Acids / Q000737:chemistry; D015227:Lipid Peroxidation / Q000187:drug effects; D008081:Liposomes; D008297:Male; D009570:Nitriles / Q000494:pharmacology; D016877:Oxidants / Q000494:pharmacology; D010545:Peroxides / Q000737:chemistry / Q000378:metabolism; D010713:Phosphatidylcholines / Q000378:metabolism; D051381:Rats; D017207:Rats, Sprague-Dawley; D012996:Solutions; D014810:Vitamin E / Q000737:chemistry
C106323:2-(glucopyranosyl)methyl-2,5,7,8-tetramethylchroman-6-ol; D000578:Amidines; D000975:Antioxidants; D001391:Azo Compounds; D002839:Chromans; D016166:Free Radical Scavengers; D005609:Free Radicals; D006027:Glycosides; D008041:Linoleic Acids; D008081:Liposomes; D009570:Nitriles; D016877:Oxidants; D010545:Peroxides; D010713:Phosphatidylcholines; D012996:Solutions; C055792:2,2'-azobis(2,4-dimethylvaleronitrile); D014810:Vitamin E; C005575:methyl linoleate; C049375:perhydroxyl radical; C046728:2,2'-azobis(2-amidinopropane); D003300:Copper