Summary
A new complex lipide, phytoglycolipide, has been isolated from soybea,, corn, flaxseed, peanut, sunflowerseed, cottonseed, and wheat phosphatides. This material is obtained by a mild alkaline saponification procedure which destroys glycerol-containing lipides. The new lipide constitutes about 5% of the crude phosphatides and is obtained as a white amorphous powder of identical composition, optical activity, and solubility properties from the various sources. Phytoglycolipide gives on hydrolysis phytosphingosine (and, in the case of soybean only, an unsaturated derivative of phytosphingosine) fatty acids, inositol, glucosamine, a hexuronic acid, galactose, arabinose, mannose, and phosphate.
Phytoglycolipide is the first sphingolipide of plant origin to be described and is unique among complex sphingolipides in that it has the structural features of a glycolipide and of a phosphatide.
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Carter, H. E., Celmer, W. D., Lands, W. E. M., Mueller, K. L., and Tomizawa, H. H., J. Biol. Chem.,206, 613 (1954).
Carter, H. E., and Fujino, Y., J. Biol. Chem.,221, 879 (1956).
Carter, H. E., Galanos, D. S., and Fujino, Y., Canad. J. Biochem. and Physiol.,34, 320 (1956).
Carter, H. E., Galanos, D. S., Gigg, R. H., Law, J. L., Nakayama, T., Smith, D. B., and Weber, E. J., Federation Proc.,16, 817 (1957).
Celmer, W. D., and Carter, H. E., Physiol. Rev.,32, 167 (1952).
Chibnall, A. C., Piper, S. H., and Williams, E. F., Biochem. J.55, 711 (1953).
Craig, L. C., J. Biol. Chem.,155, 519 (1944).
Davidson, E. A., and Meyer, K., J. Am. Chem. Soc.,76, 5686 (1954).
Desjobert, A., and Petek, F., Bull. soc. chim. biol.38, 871 (1956).
Dische, Z., J. Biol. Chem.,167, 189 (1947).
Faure, M., and Morelec-Coulon, M., Bull. soc. chim. biol.39, 947 (1957).
Folch, J., Federation Proc.,6, 252 (1947).
Folch, J., “Phosphorus Metabolism,” vol. 2, p. 186, Baltimore, Williams and Wilkins, 1952.
Frampton, V. L., Edwards, J. D. Jr., and Herze, H. R., J. Am. Chem. Soc.,73, 4,432 (1951).
Harris, W. D., and Pranjivar, P., J. Am. Oil Chemists’ Soc.,31, 124 (1954).
Hawthorne, J. N., Intern. Colloquium Biochem. Problem. Lipiden, p. 59, Koninkl. Vlaam. Acad. Wetenschap., letter, en Schone Kunsten België, Kl. Wetenschap., 1953.
Hawthorne, J. N., Biochim. et Biophys., Acta,18, 389 (1955).
Hawthorne, J. N., and Chargaff, E., J. Biol. Chem.,206, 27 (1954).
Hutt, H. W., Malkin, T., Poole, A. G., and Watt, P. R., Nature,165, 314 (1950).
Klenk, E., and Sakai, R., Z. physiol. Chem.,258, 33 (1939).
Leaback, D. H., and Walker, P. G., Biochem. J.,67, 22P (1957).
McGuire, T. A., and Earle, F. R., J. Am. Oil Chemists’ Soc.,28, 328 (1951).
McKibben, J. M., and Taylor, W. E., J. Biol. Chem.,178, 291 (1949).
Malkin, T., and Poole, A. G., Chem. Soc., 3, 470 (1953).
Okuhara, E., and Nakayama, T., J. Biol. Chem.,215, 295 (1955).
Olcott, H. S., Science,100, 226 (1944).
Olley, J., Biochim. et Biophys. Acta,10, 439 (1953).
Proŝtenik, M., Croat. Chem. Acta,28, 287 (1956).
Proŝtenik, M., and Stanacev, N. Z., Naturwissenschaften,43, 447 (1956).
Radin, N. A., Lavin, F. B., and Brown, J. R., J. Biol. Chem.,217, 789 (1955).
Schmidt, G., Benotti, J., Hershman, B., and Thannhauser, S. J., J. Biol. Chem.,166, 505 (1946).
Scholfield, C. R., and Dutton, H. J., J. Biol. Chem.208, 461 (1954).
Scholfield, C. R., Dutton, H. J., and Dimler, J., J. Am. Oil Chemists’ Soc.,29, 293 (1952).
van Handel, E., “The Chemistry of Phosphoaminolipids,” p. 80. Amsterdam, D.B. Centen. 1954; Rec. trav. chim.72, 764 (1953).
Wagenknecht, A. C., and Carter, H. E., Federation Proc.,16, 266 (1957).
Weissmann, B., Rapport, M. M., Tinker, A., and Meyer, K., J. Biol. Chem.,205, 205 (1953).
Woolley, D. W., J. Biol. Chem.,147, 581 (1943).
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The soybean phosphatide work was done under contract with the U.S. Department of Agriculture and was authorized by the Research and John C. Cowan of the Northern Utilization Research and Development Division of the Agricultural Research Service, Peoria, Ill. The corn phosphatide work was supported in part by research grants (B574-C2, 3, 4) from the National Institutes of Health, United States Public Health Service. Part of the material in this paper was taken from the theses submitted by Walter D. Celmer, William E. M. Lands, John H. Law, and H. H. Tomizawa to the Graduate College of the University of Illinois in partial fulfilment of the requirements for the degree of Doctor of Philosophy in Chemistry.
A preliminary report of this work has been published (4). For number IX in this series see reference (2)
Postdoctorate Rosearch Associate, Department of Chemistry
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Carter, H.E., Celmer, W.D., Galanos, D.S. et al. Biochemistry of the sphingolipides. X. Phytoglycolipide, a complex phytosphingosine-containing lipide from plant seeds. J Am Oil Chem Soc 35, 335–343 (1958). https://doi.org/10.1007/BF02640547
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DOI: https://doi.org/10.1007/BF02640547