A Study of the Calcium Complex of a Glucosylceramide, Soya-cerebroside II

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  • Kurosu Michio
    Department of Microbiology, Immunology, and Pathology, College of Veterinary Medicine and Biomedical Sciences, Colorado State University
  • Katayama Seiji
    Graduate School of Pharmaceutical Sciences, Osaka University
  • Shibuya Hirotaka
    Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University
  • Kitagawa Isao
    Graduate School of Pharmaceutical Sciences, Osaka University

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  • A study of the calcium complex of a glucosylceramide, soya-cerebroside 2

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In order to study calcium ion complex of soya-cerebroside II (1), an ionophoretic glucosylceramide isolated from soybean, C8-cerebroside (3) and 3,3″,6″-trideoxy-C8-cerebroside (4) are designed and synthesized. On the basis of extensive 1H-NMR studies in the presence of Ca2+ and a continuous variation method via 1H-NMR, soya-cerebroside II is suggested to form a calcium complex with 1/Ca2+ ratio of 1 : 1. Soya-cerebroside II serves as a tridentate chelating ligand for Ca2+; the amide carbonyl, C2′-hydroxy, and C2″-hydroxy oxygens are responsible for the Ca2+ binding. Soya-cerebroside II is structurally analogous to a neural glucosylceramide. Thus, the accumulated neural glucosylceramide inside of endoplasmic reticulum (ER) membrane may serve as an endogenous Ca2+-binding and -transport molecule (ionophore) that result in mobilization of Ca2+ from intracellular calcium stores.

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