Synthesis and physiological activity of novel tocopheryl glycosides.
Vitamin E glycosides were synthesized and enzymatic hydrolysis was examined for use as potential pro-drugs, however, the glycoside bond was found to be stable. On the other hand, among the glycosides synthesized, dl-alpha-tocopherylglucoside (6b) and dl-alpha-tocopherylmannoside (6c) showed strong inhibitory action on histamine release from mast cells. In addition, 6c also showed a suppressive action on IgE antibody formation. Thus, tocopheryl glycoside showed new properties compared to tocopherol (vitamin E). In particular, 6c was shown to be a novel lead compound with excellent manifold anti-allergic activity and anti-inflammatory activity.
Satoh
T
T
Department of Bio-organic Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Miyataka
H
H
Yamamoto
K
K
Hirano
T
T
D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D006636:Histamine Release / Q000187:drug effects / Q000502:physiology; D007073:Immunoglobulin E / Q000097:blood / Q000276:immunology; D008297:Male; D008407:Mast Cells / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D008810:Mice, Inbred C57BL; D051381:Rats; D017207:Rats, Sprague-Dawley; D017208:Rats, Wistar; D024505:Tocopherols / Q000138:chemical synthesis* / Q000494:pharmacology; D014810:Vitamin E / Q000138:chemical synthesis / Q000494:pharmacology
D000975:Antioxidants; D006027:Glycosides; D014810:Vitamin E; D007073:Immunoglobulin E; D024505:Tocopherols