Antioxidant activities of chitobiose and chitotriose.
Chitooligosaccharides, the oligomers made up of beta-1,4-linked D-glucosamine, are obtained by partial hydrolysis of chitosan, a deacetylation product of chitin. The antioxidant activity of various chitooligosaccharides was tested in vitro with aminoguanidine, pyridoxamine, and Trolox as reference compounds. Hydroxylation of benzoate to salicylate by H2O2 in the presence of Cu(2+) was effectively inhibited by chitobiose, chitotriose, aminoguanidine, pyridoxamine, and Trolox (their IC(50) values=18, 80, 85, 10, and 95 microM, respectively), whereas glucosamine and N-acetylchito-oligosaccharides (di-N-acetylchitobiose and tri-N-acetylchitotriose) did not show any inhibitory activity. Chitobiose and chitotriose were more potent than the 3 reference compounds in scavenging hydroxyl radicals produced by photolysis of zinc oxide: IC(50) values of the 2 oligomers were 30 and 55 microM, respectively. Such a scavenging activity of these 2 chitooligomers was also shown by the use of another system, a mixture of Fe(3+)/EDTA/ascorbate/H2O2, for producing hydroxyl radicals. Only chitobiose and Trolox, of the 10 compounds tested, had the ability to scavenge superoxide radicals generated by a non-enzymatic system using phenazine methosulfate and NADH. Taken together with our unpublished observation that chitobiose and chitotriose are appreciably absorbed from the intestine of rats, the present results suggest that these 2 chitooligosaccharides would act as effective antioxidants in vivo when orally ingested.
Chen
An-Shu
AS
Department of Pathobiochemistry, Faculty of Pharmacy, Meijo University, Tempaku-ku, Nagoya, Japan.
Taguchi
Tadao
T
Sakai
Kazuo
K
Kikuchi
Kazuaki
K
Wang
Min-Wei
MW
Miwa
Ichitomo
I
D000975:Antioxidants / Q000737:chemistry*; D001205:Ascorbic Acid / Q000737:chemistry; D001565:Benzoates / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D004187:Disaccharides / Q000737:chemistry*; D004492:Edetic Acid / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000737:chemistry; D017665:Hydroxyl Radical / Q000737:chemistry; D006900:Hydroxylation; D007501:Iron / Q000737:chemistry; D010782:Photolysis; D013481:Superoxides / Q000737:chemistry; D014312:Trisaccharides / Q000737:chemistry*; D015034:Zinc Oxide
D000975:Antioxidants; D001565:Benzoates; D004187:Disaccharides; D014312:Trisaccharides; D013481:Superoxides; D017665:Hydroxyl Radical; C041161:chitotriose; C032438:chitobiose; D003300:Copper; D004492:Edetic Acid; D006861:Hydrogen Peroxide; D007501:Iron; D001205:Ascorbic Acid; D015034:Zinc Oxide