Abstract
The 1-O-alkylglycerol composition of the liver oil of the deep sea sharkCentrophorus squamosus, a species which provides edible flesh, has been determined. After various fractionations of the oil, the unsaponifiable fraction was characterized by means of gas chromatography/mass spectrometry, electron impact, and positive-ion chemical ionization. The oil is composed of 60% unsaponifiable matter, containing 45% squalene, 4.5% cholesterol, and 10% of linear saturated and monounsaturated glycerol ethers with 14–18 carbon atoms. After a first separtion by chromatography on silicic acid, monounsaturated glycerol ethers have been separated from the saturated homologues, in particular from 1-O-octadecylglycerol (batyl alcohol) and 1-O-hexadecylglycerol (chimyl alcohol)via urea complexation. This newer application of the urea method, already used in the past to extract saturated from polyunsaturated fatty acids, allowed the purification of the main components of the complex unsaturated glycerol ether fraction, namely, 1-O-octadecen-9′ylglycerol (selachyl alcohol) and 1-O-hexadecen-9′ylglycerol.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
Abbreviations
- APRL:
-
antihypertensive polar renomedullary lipid
- DHA:
-
docosahexaenoic acid
- DMA:
-
docosamonoenoic acid
- EI:
-
electron impact
- EPA:
-
eicosapentaenoic acid
- FID:
-
flame-ionization detector
- GC/MS:
-
gas chromatography/mass spectrometry
- GE:
-
glycerol ethers
- PAF:
-
platelet-activating factor
- PCI:
-
positive-ion chemical ionization
- TLC:
-
thin-layer chromatography
- TMS:
-
trimethylsilyl radical. The abbreviation “en-n’yl” for 1-O-alkylglycerols indicate a normalcis ethylenic bond on thenth carbon from the ether oxygen
References
Peyronel, D., Artaud, J., Iatrides, M.C., Rancurel, P., and Chevalier, J.L. (1984) Fatty Acid and Squalence Compositions of Mediterranean Centrophorus SPP Egg and Liver Oils in Relation to Age,Lipids 19, 643–648.
Van Vleet, E.S., Candileri, S., McNeillie, J., Reinhardt, S.B., Conkright, M.E., and Zwissler, A. (1984) Neutral Lipid Components of Eleven Species of Caribbean Sharks,Comp. Biochem. Physiol. 79B, 549–554.
Bordier, C.G., Sellier, N., Foucault, A.P., and Le Goffic, F. (1994) Characterization and Purification of Fatty Acid Methyl Esters from the Liver Oil of the Deep Sea Shark (Centrophorus squamosus) by Gas Chromatogrphy-Mass Spectrometry and Countercurrent Chromatography,Chromatographia 39, 329–338.
Olsen, A.M. (1988) L’Utilisation des Requins, inLes Requins (Stevens, J.D., ed.), pp. 186–195, Bordas, Paris.
Boeryd, B., Hallgren, B., and Ställberg, G. (1971) Studies on the Effect of Methoxy-Substitued Glycerol Ethers on Tumour Growth and Metastasis Formation,Br. J. Exp. Pathol. 52, 221–230.
Hallgren, B. (1983) Therapeutic Effects of Ether Lipids, inEther Lipids: Biochemical and Biomedical Aspects (Mangold, H. K. and Paltauf, F., eds.) pp. 261–275, Academic Press, New York.
Burford, R.G., and Gowdey, C.W. (1968) Anti-Inflammatory Activity of Alkoxyglycerols in Rats,Arch. Int. Pharmacodyn 173, 56–70.
Boeryd, B., Nilsson, T., Lindholm, L., Lange, S., Hallgren, B., and Ställberg, G. (1978) Stimulation of Immune Reactivity by Methoxy-Substituted Glycerol Ethers Incorporated into the Feed,Eur. J. Immunol. 8, 678–680.
Brohult, S., and Brohult, A. (1989) Use of Glycerol Ethers in the Treatment of Allergic Diseases, Swedish Patent 0333678.
Brohult, A., Brohult, J., Brohult, S., and Joelsson, I. (1986) Reduced Mortality in Cancer Patients After Administration of Alkoxyglycerols,Acta Obstet. Gynecol. Scand. 65, 779–785.
Barbaro, J.F., and Zvaifler, N.J. (1966) Antigen Induced Histamine Release from Platelets of Rabbits Producing Homologous PCA Antibody,Proc. Soc. Exp. Biol. Med. 122, 1245–1247.
Benveniste, J., Le Couedic, J.P., Polonsky, J.P., and Tencé, M. (1977) Structural Analysis of Purified Platelet-Activating Factor by Lipases,Nature (Lond.) 269, 170–176.
Benveniste, J., and Vargaftig, B.B. (1983) Platelet-Activating Factor: An Ether Lipid with Biological Activity, inEther Lipids: Biochemical and Biomedical Aspects (Mangold, H.K., and Paltauf, F., eds.), pp. 261–275, Academic Press, New York.
Demopoulos, C.A., Pinckard, R.N., and Hanahan, D.J. (1979) Platelet-Activating Factor Evidence for 1-O-Alkyl-2-Acetyl-sn-Glyceryl-3-Phosphorylcholine as the Active Component (A New Class of Lipid Chemical Mediators),J. Biol. Chem. 254, 9355–9358.
Blank, M.L., Snyder, F., Byers, L.W., Brooks, B., and Muirhead, E.E. (1979) Antihypertensive Activity of an Alkyl Ether Analog of Phosphatidylcholine,Biochem. Biophys. Res. Commun. 90, 1194–1199.
Commission Nationale de Pharmacopée Française (1983)Parmacopée Française, 10th edn., V.3.4.7., Adrapharm, Paris.
Ackman, R.G., Timmins, A.M., and Shanta, N.C. (1990) Clarification on Method Ce-1b-89,INFORM 1, 987–988.
Subrahmanyam, C., Venkateswara Rao, C., Anjaneyulu, V., Satyanarayana, P., Subba Rao, P.V., Ward, R.S., and Pelter, A. (1992) New Diterpenes from a New Species of Lobophytum Soft Coral of the South Andaman Coast,Tetrahedron 48, 3111–3120.
Malins, D.C., Wekell, J.C., and Houle, C.R. (1965) Composition of the Diacyl Glyceryl Ethers and Triglycerides of the Flesh and Liver of the Dogfish (Squalus acanthias),J. Lipid Res. 6, 100–105.
Myher, J.J., and Kuksis, A. (1974) Gas Chromatographic Resolution of Homologous Monoacyl and Monoalkylglycerols,Lipids 9, 382–387.
Christie, W.W. (1987)HPLC and Lipids, pp. 102–105, Pergamon Press, Oxford.
Holman, R.T. (1978)EPA/NIH Mass Spectral Data Base, Vol. 4, p. 3170, Heller and Milne, Washington.
Pizzoferrato, L., Nicoli, S., and Lintas, C. (1993) GC-MS Characterization and Quantification of Sterols and Cholesterol Oxidation Products,Chromatographia 35, 269–274.
Egge, H. (1983) Mass Spectrometry of Ether lipids, inEther Lipids: Biochemical and Biomedical Aspects (Mangold, H.K., and Paltauf, F., eds.), pp. 17–47, Academic Press, New York.
Hallgren, B., and Ställberg, G. (1967) Methoxy-Substituted Glycerol Ethers Isolated from Greenland Shark Liver Oil,Acta Chem. Scand. 21, 1519–1529.
Hallgren, B., Niklasson, A., Ställberg, G., and Thorin, H. (1974) On the Occurrence of 1-O-(2-Methoxyalkyl)Glycerols and 1-O-Phytanylglycerol in Marine Animals,Acta Chem. Scand. 28B, 1035–1040.
Hallgren, B., and Ställberg, G. (1974) 1-O-(2-Hydroxyalkyl) Glycerols Isolated from Greenland Shark Liver Oil,Acta Chem. Scand. 28B, 1074–1076.
Haagsma, N., Van Gent, C.M., Luten, J.B., de Jong, R.W., and Van Doorn, E. (1982) Preparation of an ω3 Fatty Acid Concentrate from Cod Liver Oil,J. Am. Oil Chem. Soc. 59, 117–118.
Ratnayake, W.M.N., Olsson, B., Matthews, D., and Ackman, G. (1988) Preparation of Omega-3 PUFA Concentrates from Fish Oils via Urea Complexation,Fat Sci. Technol. 90, 381–386.
Tsoucaris, G. (1987) Clathrates and Solid Inclusion Compounds, inCyclodextrins and Their Industrial Uses (Duchêne D., ed.), pp. 21–73, Edition de Santé, Paris.
Ackman, R.G., Addison, R.F., and Eaton, C.A. (1968) Unusual Occurrence of Squalene in a Fish, the EulachonThaleichthys pacificus, Nature (Lond.) 220, 1033–1034.
Bakes, M.J., and Nichols, P.D. (1995) Lipid, Fatty Acid and Squalene Composition of Liver Oil from Six Species of Deep-Sea Sharks Collected in Southern Australian Waters,Comp. Biochem. Physiol. 110B, 267–275.
Dingerkus, G. (1988) La Distribution des Requins, inLes Requins (Stevens, J.D., ed.), pp. 36–49, Bordas, Paris.
Heller, J.H., Heller, M.S., Springer, S., and Clark, E. (1957) Squalene Content of Various Shark Livers,Nature (Lond.) 179, 919–920.
Corner, E.D.S., Denton, E.J., Forster, F.R.S., and Forster, G.R. (1969) On the Buoyancy of Some Deep-Sea Shark,Proc. Roy. Soc. 171B, 415–429.
Malins, D.C., and Barone, A. (1970) Glyceryl Ether Metabolism: Regulation of Buoyancy in DogfishSqualus acanthias, Science 167, 79–80.
Stein, R.A., and Mead, J.F. (1988) Small Hydrocarbons Formed by the Peroxidation of Squalene,Chem. Phys. Lipids 46, 117–120.
Myher, J.J., Marai, L., and Kuksis, A. (1974) Identification of Monoacyl and Monoalkylglycerols by Gas-Liquid Chromatography-Mass Spectrometry Using Polar Siloxane Liquid Phases,J. Lipid Res. 15, 586–591.
Hallgren, B., Ställberg, G., and Boeryd, B. (1978) Occurrence, Synthesis and Biological Effects of Substituted Glycerol Ethers,Prog. Chem. Fats Other Lipids 14, 45–58.
Hallgren, B., Ställberg, G., and Thorins, H. (1971) The Separation and Identification of a Methoxy-Substituted Polyunsaturated Glycerol Ether from Greenland Shark Liver Oil,Acta Chem. Scand. 25, 3781–3784.
Malosse, C., and Einhorn, J. (1986) Double Bond Location in Long Chain Mono-Unsaturated Alcohols, Acetates and Aldhehydes by CI-NO+-MS,Adv. Mass Spectrom. 108, 1369–1374.
Author information
Authors and Affiliations
About this article
Cite this article
Bordier, C.G., Sellier, N., Foucault, A.P. et al. Purification and characterization of deep sea sharkCentrophorus squamosus liver oil 1-O-aklylglycerol ether lipids. Lipids 31, 521–528 (1996). https://doi.org/10.1007/BF02522646
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF02522646