title: Inhibitory Effects of the C-2 Epimeric Isomers of Tea Catechins on Mouse Type IV Allergy.
abstract: The inhibitory effects of C-2 epimeric isomers of (-)-epigallocatechin-3-O-gallate (EGCG) and two O-methylated EGCG derivatives, (-)-epigallocatechin-3-O-(3-O-methyl)gallate (EGCG3''Me) and (-)-epigallocatechin-3-O-(4-O-methyl)gallate (EGCG4''Me), against oxazolone-induced type IV allergy in male mice were investigated. These compounds exhibited strong antiallergic effects by percutaneous administration at a dose of 0.13 mg/ear. The inhibition rates of (-)-gallocatechin-3-O-gallate (GCG), (-)-gallocatechin-3-O-(3-O-methyl)gallate (GCG3''Me), and (-)-gallocatechin-3-O-(4-O-methyl)gallate (GCG4''Me) on mouse type IV allergy were 52.1, 53.3, and 54.8%, respectively. However, the antiallergic effects were weaker than those of their corresponding original tea catechins (2R,3R type). The inhibition rates of those were 88.0, 73.2, and 77.6%, respectively. For all of the catechins tested, oral administration at a dose of 50 mg/kg body weight significantly suppressed the allergic symptoms. The inhibitory rates varied from 24.0 to 60.6%. No significant differences were observed between the effects of the epimers (2S,3R type) and their corresponding original catechins (2R,3R type). The antiallergic effects of tea catechins and their C-2 epimers observed in this study were dose-dependent. These results suggest that C-2 epimers of tea catechins, which are produced during heat processing at high temperatures, could be disadvantageous for the antiallergic effects on type IV allergy.
authors.affiliation: Department of Chemistry and Biochemistry, Numazu College of Technology, 3600 Ooka, Numazu, Shizuoka 410-8501, Japan.
authors.forename: Kyoji
authors.initials: K
authors.lastname: Yoshino
authors.forename: Kenjiro
authors.initials: K
authors.lastname: Ogawa
authors.forename: Toshio
authors.initials: T
authors.lastname: Miyase
authors.forename: Mitsuaki
authors.initials: M
authors.lastname: Sano
mesh_terms: D000818:Animals; D018926:Anti-Allergic Agents; D002392:Catechin / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000627:therapeutic use*; D003877:Dermatitis, Contact / Q000517:prevention & control*; D007536:Isomerism; D008297:Male; D051379:Mice; D008813:Mice, Inbred ICR; D010081:Oxazolone / Q000276:immunology; D013662:Tea / Q000737:chemistry*
chemical_list: D018926:Anti-Allergic Agents; D013662:Tea; D010081:Oxazolone; D002392:Catechin; C045651:epigallocatechin gallate