Synthesis and Physiological Activity of Novel Tocopheryl Glycosides.

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  • SATOH Toshio
    Department of Bio-organic Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Tokushima Bunri University
  • MIYATAKA Hideki
    Department of Bio-organic Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Tokushima Bunri University
  • YAMAMOTO Kyozo
    Department of Bio-organic Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Tokushima Bunri University
  • HIRANO Takashi
    Department of Bio-organic Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Tokushima Bunri University

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Abstract

Vitamin E glycosides were synthesized and enzymatic hydrolysis was examined for use as potential prodrugs, however, the glycoside bond was found to be stable. On the other hand, among the glycosides synthesized, dl-α-tocopherylglucoside (6b) and dl-α-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.

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