Abstract
The chemical structures of an acidic phospholipid originally isolated from equine intestine by Vogt and of a phospholipid isolated from rabbit kidney medulla by Walaszek are shown by total synthesis to be similar mixtures of 2-alkyl (and alkenyl)-4-hydroxymethyl-1,3-dioxolane-dihydrogen phosphate esters. In these materials, the alkyl residues derive primarily from oleyl, palmityl and linoleyl aldehydes. The smooth muscle contracting activity observed in the natural substances is shown to reside exclusively in the oleyl aldehyde derivative.
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References
Vogt, W., Arch. Exp. Path. Pharmak., 206:1 (1949); (b) J. Physiol. 137:154 (1957).
Davenport, J. B., and R.M.C. Dawson, Biochem. J. 84:490 (1962).
Dyer, D., and E.J. Walaszek, J. Pharmacol. Exptl. Therap. 160:360 (1968).
Lee, J.B., K. Crowshaw, B.H. Takman, K.A. Attrep and J.Z. Gougotas, Biochem. J. 105:1251 (1967).
Carroll, K.K., J. Lipid Res. 2:135 (1961).
Skidmore, W.D., and C. Enterman, Ibid. 3:471 (1962).
Hanes, C.S., and F.A. Isherwood, Nature 164:1102 (1949).
Farquhar, J.W., J. Lipid Res. 1:361 (1960).
Cookson, R.C., and N.S. Wariyar, J. Chem. Soc. 1956:2302; (b) “Sadtler Standard NMR Spectra”, Sadtler Research Laboratories, Philadelphia, 1968.
Piantadosi, C., C. E. Anderson, E.A. Brecht and C.L. Yarbro, J. Amer. Chem. Soc. 80:6613 (1958).
Bauer, S.T., Oil and Soap 23:1 (1946).
Rao, P.V., S. Ramachandran and D.G. Cornwell, J. Lipid Res. 8:380 (1967).
Piantadosi, C., A.F. Hirsch, C.L. Yarbro and C.E. Anderson, J. Org. Chem. 28:2425 (1963).
Brigl, P., and H. Mueller, Chem. Ber. 72:2121 (1939).
Edgerton, M.J., and T. Malkin, J. Chem. Soc. 1953:2800.
Craig, L.C., and D. Craig, in “Techniques of Organic Chemistry” Edited by A. Weissburger, Interscience Publishers, New York, 1956, p. 149.
Vogt, W., Biochem. Pharmacol. 12:415 (1963).
Gray, G.W., J. Pharmacol. Exp. Ther. 146:215 (1964).
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Wiley, R.A., Sumner, D.D. & Walaszek, E.J. Structure determinations and synthesis of pharmacologically active phospholipids from kidney and intestine. Lipids 5, 803–811 (1970). https://doi.org/10.1007/BF02531972
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DOI: https://doi.org/10.1007/BF02531972