Abstract
Wax esters occur as a major lipid-type in at least 30 species of marine animals, distributed among 17 orders and 3 phyla. They are of limited usefulness as a chemotaxonomic character, since only in two suborders, the calanoid copepods, Calanoidei, and the toothed whales, Odontoceti, do the wax esters occur in all members so far examined. In bony fishes their occurrence in muscle correlates better with mesopelagic habitat and vertical migration patterns than with taxonomy. Homologs with 21 to 44 total carbon atoms have been reported, but the usual range for the wax esters in copepods and fish is C30–C42. In fishes the muscle wax esters contain predominantly one and two double bonds per molecule, while in roe lipids up to 65% of the homologs contain three or more double bonds. The component alcohols are saturated and monounsaturated, with 16∶0 and 18∶1 as the usual major constituents. The fatty acids are more diverse, but 18∶1 is most often the main component, and 16∶1 and 20∶1 are frequent major constituents; polyunsaturated acids make up 1–12% in fish muscle and whale oils and up to 45% in fish roe wax esters. Possible functions of the wax esters are for buoyancy, as energy reserves and for thermal insulation. In vitro, various tissues of marine bony fishes synthesize wax esters from long chain alcohols and fatty acids, without activation. A competing pathway for the long chain alcohols in vivo is their catabolic oxidation to the corresponding fatty acids. The key to the accumulation of wax esters is to be sought in the metabolism of the long chain alcohols, their biosynthesis and esterification vs. their catabolism.
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Banner, A. H., J. C. Nevenzel and W. R. Hudgins, Atoll Res. Bull., No. 122, March 30, 1969.
Bergmann, W., S. M. Creighton, and W. M. Stokes, J. Org. Chem. 21:721 (1956).
Bergmann, W., R. J. Feeney, and A. N. Swift, Ibid. 16:1337 (1951).
Capen, R. L., “Swimbladder Morphology of Some Mesopelagic Fishes in Relation to Sound Scattering,” Report 1447, U.S. Navy Electronics Laboratory, San Diego, Calif., 1967.
Chevreul, M. E., Ann. Chim. Phys. [1] 95:5 (1815); Ibid. Chevreul, M. E., Ann. Chim. Phys. [2] 7:155 (1817).
Ciereszko, L. S., M. A. Johnson, R. W. Schmidt and C. B. Koons, Comp. Biochem. Physiol. 24:899 (1968).
Collin, G., J. C. Drummond, T. P. Hilditch, and E. R. Gunther, J. Exptl. Biol. 11:198 (1934).
Cox, W. M., Jr., and E.E. Reid, J. Am. Chem. Soc. 54:220 (1932).
Gill, A. H., and C. M. Tucker, Oil Fat Ind. 7:101 (1930).
Haahti, E. O. A., and E. C. Horning, Acta Chem. Scand. 15:930 (1961).
Hatano, M., Hokkaido Daigaku Suisan Gakubu Kenkyu Iho (Bull. F. Fisheries, Hokkaido Univ.) 11:218 (1961).
Hatano, M., K. Zama, and H. Igarashi, Nippon Suisan Gakkaishi 30:516 (1964).
Hilditch, T. P., and J. A. Lovern, J. Soc. Chem. Ind. 47:105T (1928); Ibid. J. Soc. Chem. Ind 49:359T, 365T (1929).
Igarashi, H., K. Zama, and A. Ishigaki, Nippon Suisan Gakkaishi 18:493 (1953).
Igarashi, H., K. Zama, and M. Katada, Nippon Nogeikagaku Kaishi 30:111 (1956); Chem. Abstr. 51:9012 (1957).
Igarashi, H., K. Zama, and M. Katada, Nippon Nogeikagaku Kaishi 30:568 (1956); Chem. Abstr. 51:9013 (1957).
Igarashi, H., K. Zama, and M. Katada, Nippon Suisan Gakkaishi 26:326 (1960).
Iyengar, R., and H. Schlenk, Biochemistry 6:396 (1967).
Kafuku, K., and C. Hata, Kogyo Kagaku Zasshi 37:1035 (1934); English summary, Suppl. Binding, p. 455; Chem. Abstr. 28:7570 (1934).
Kaufmann, H. P., and E. Gottschalk, Fette Seifen Anstrichmittel 56:512 (1954); Ibid. Fette Seifen Anstrichmittel 58:411 (1956).
Kind, C. A., and W. Bergmann, J. Org. Chem. 7:424 (1942).
Kumura, K., Kogyo Kaguku Zasshi 29:620 (1926).
Komori, S., and T. Agawa, Nippon Kagaku Zasshi 74:1025 (1953); Chem. Abstr. 48: 12012 (1954); T. Agawa, Y. Hirao and S. Komori, Yukagaku 2:246 (1953); Chem. Abstr. 48: 9721 (1954).
Komori, S., and T. Agawa, JAOCS 32:525 (1955).
Komori, S., and T. Agawa, Nippon Kagaku Zasshi 75:1051 (1954); Chem. Abstr. 49:11538 (1955); S. Komori, T. Agawa, H. Hirao and K. Kumata, Yukagaku 5:284 (1956); Chem. Abstr. 51:12512 (1957).
Lester, D., and W. Bergmann, J. Org. Chem. 6:120 (1941).
Lovern, J. A., Biochem. J. 28:394 (1934).
Lovern, J. A., Ibid. 29:847 (1935).
Lovern, J. A., in “Oceanography and Marine Biology; An Annual Review,” Vol. 2, Edited by H. Barnes, Allen and Unwin, London, 1964, p. 169.
Malins, D. C., Biochem. J. 101: 39P (1966).
Malins, D. C., in “Fish Oils; Their Chemistry, Technology, Stability, Nutritional Properties and Uses,” Edited by M. E. Stansby, Avi Publishing Co., Westport, Conn., 1967, p. 36.
Marshall, N. B., Discovery Rept. 31:68 (1960).
Marshall, N. B., “The Life of Fishes,” World Publishing Co., Cleveland and New York, 1966, p. 69–71.
Matsumoto, T., H. Sone, and I. Niiya, Yukagaku 4:131 (1955); Chem. Abstr. 49:16471 (1955).
Mori, M., Y. Iwakiri, A. Ozawa, and S. Shibata, Nippon Suisan Gakkaishi 30:161 (1964).
Mori, M., and T. Saito, Ibid. 32:730 (1966).
Mori, M., T. Saito, and Y. Nakanishi, Ibid. 32:668 (1966).
Mori, M., T. Saito, Y. Nakanishi, K. Miyazawa and Y. Hashimoto, Ibid. 32:137 (1966).
Mori, M., T. Saito, and Y. Watanabe, Ibid. 31:448 (1965).
Mori, M., T. Saito, Y. Watanabe, and Y. Nakanishi, Ibid. 31:638 (1965).
Naito, K., and Y. Hashimoto, Ibid. 26:1032 (1960).
Nevenzel, J. C., and M. Kayama, Federation Proc. 26:647, Abstr. No. 2427 (1968).
Nevenzel, J. C., W. Rodegker, and J. F. Mead, Biochemistry 4:1589 (1965).
Nevenzel, J. C., W. Rodegker, J. F. Mead, and M. S. Gordon, Science 152:1753 (1966).
Nevenzel, J. C., W. Rodegker, J. S. Robinson and M. Kayama, Comp. Biochem. Physiol. 31:25 (1969).
Panzer, T., Z. Physiol. Chem. 73:109 (1911).
Rosenberg, A., and M. Pecker, Biochemistry 3:254 (1964); P. F. Guehler, L. Peterson, H. M. Tsuchiya and R. M. Dodson, Arch. Biochem. Biophys. 106: 294 (1964).
Saiki, M., Nippon Suisan Gakkaishi 19:809 (1953).
Saiki, M., S. Fang, and T. Mori, Ibid. 24:578 (1958).
Saiki, M., and T. Mori, Ibid. 21:1041 (1956).
Sand, D. M., and H. Schlenk, Lipids 4:303 (1969).
Sano, Y., Nippon Suisan Gakkaishi 34:734 (1968).
Snyder, F., B. Malone and J. Soodsma, 60th AOCS Annual Meeting, Abstr. No. 8, San Francisco, Calif., April 1969.
Tateishi, T., M. Fujiwara, and H. Sakurai, Kogyo Kagaku Zasshi 61:1580 (1958); Chem. Abstr. 55:27923 (1961).
Tateishi, T., M. Fujiwara, and H. Sakurai, Kogyo Kagaku Zasshi 61:1583 (1958); Chem. Abstr. 55:27923 (1961).
Toyama, Y., Chem. Umschau 29:233, 245 (1922); Chem. Abstr. 17:892 (1923).
Toyama, Y., Nippon Kagaku Zasshi 59:810 (1938); Chem. Abstr. 32:8810 (1938); Y. Toyama and G. Akiyama, Nippon Kagaku Zasshi 56:1077 (1935); Chem. Abstr. 30:316 (1936) [same as Bull. Chem. Soc. Japan 10:579 (1935); Chem. Abstr. 30:2030 (1936)]; Y. Toyama and T. Tsuchiya, Nippon Kagaku Zasshi 56: 1072 (1935); Chem. Abstr. 30:316 (1936) [same as Bull. Chem. Soc. Japan 10: 573 (1935); Chem. Abstr. 30:2030 (1936)].
Toyama, Y., and T. Isikawa, Nippon Kagaku Zasshi 59:1193 (1938); Chem. Abstr. 33:1978 (1939).
Tsujimoto, M., Kogyo Kagaku Zasshi 36:1616 (1933); English summary, Suppl. Binding, p. 676; Chem. Abstr. 28:560 (1934); M. Tsujimoto, Kogyo Kagaku Zasshi 41:641 (1938); English summary, Suppl. Binding, p. 322; Chem. Abstr. 33:1529 (1939).
Tsujimoto, M., Kogyo Kagaku Zasshi 41:852 (1938); English summary, Suppl. Binding, p. 410; Chem. Abstr. 33:3193 (1939).
Tsujimoto, M., and H. Koyanagi, Kogyo Kagaku Zasshi 40:391 (1937); English summary, Suppl. Binding, p. 191; Chem. Abstr. 31:6912 (1937).
Tsujimoto, M., and H. Koyanagi, Kogyo Kagaku Zasshi 40:590 (1937); English summary, Suppl. Binding, p. 272; Chem. Abstr. 31:7685 (1937).
Tsujimoto, M., and H. Koyanagi, Kogyo Kagaku Zasshi 40:694 (1937); English summary, Suppl. Binding, p. 315; Chem. Abstr. 32:380 (1938).
Tsujimoto, M., and H. Koyanagi, Kogyo Kagaku Zasshi 40:865 (1937); English summary, Suppl. Binding, p. 403; Chem. Abstr. 32:1963 (1938).
Tsujimoto, M., and H. Koyanagi, Kogyo Kagaku Zasshi 41:88 (1938); English summary, Suppl. Binding, p. 41; Chem. Abstr. 32: 6894 (1938).
Ueno, S., T. Hidaka, and T. Okamoto, Yukagaku 4:26 (1955); Chem. Abstr. 49:13671 (1955); S. Ueno and K. Matsushima, Yukagaku 6:222 (1957); Chem. Abstr. 55:4011 (1961).
Ueno, S., and S. Komori, Kogyo Kagaku Zasshi 38:825 (1935); English summary, Suppl. Binding, p. 345; Chem. Abstr. 29:6451 (1935).
Ueno, S., and S. Komori, Kogyo Kagaku Zasshi 38:831 (1935); English summary, Suppl. Binding, p. 352; Chem. Abstr. 29:6451 (1935).
Umezawa, B., Yakagaku Zasshi (J. Pharm. Soc. Japan), 74:682 (1954); Chem. Abstr. 48: 10533 (1954).
Watanabe, S., and Y. Abe, Yukagaku 6:267 (1957); Chem. Abstr. 55:5995 (1961).
Williams, M. Y., Trans. Roy. Soc. Can. Sect. IV, 51:13 (1957).
Yamada, M., Nippon Suisan Gakkaishi 30:673 (1964); English summary, p. 698.
Zama, K., M. Katada, and H. Kgarashi, Ibid. 24:569 (1958).
Villee, C. A., W. F. Walker, Jr., and F. E. Smith, “General Zoology,” 3rd Edition, W. B. Saunders Co., Philadelphia, 1968.
Hilditch, T. P., and P. N. Williams, “Chemical Constitution of Natural Fats,” 4th Edition, John Wiley & Sons, New York, 1964, p. 296–297.
Nicolaides, N., JAOCS 42:691 (1965); N. Nicolaides, H. C. Fu and G. R. Rice, J. Invest. Dermatol 51:83 (1968).
Adams, K. R., and R. Bonnett, Nature 223:943 (1969).
Fitch, J. E., and R. L. Lavenberg, “Deep-Water Fishes of California,” University of California Press, Berkeley and Los Angeles, 1968, p. 81–82.
Friedberg, S. J., and R. C. Greene, J Biol. Chem. 242:234 (1967).
Stetten, D., Jr., and R. Schoenheimer, Ibid. 133:347 (1940).
Davis, J. B., Appl. Microbiol. 12:210 (1944).
Culkin, F., and R. J. Morris, Deep-Sea Res. 16:109 (1969).
Toyama, Y., and T. Takagi, Mem. Fac. Eng., Nagoya Univ. 7:156 (1955); Chem. Abstr. 51:4737 (1957).
Carter, C. L., and J. Malcolm, Biochem. J. 21:484 (1927); C. L. Carter, J. Soc. Chem. Ind. 40:220T (1921).
Rosenheim, O., and T. A. Webster, Biochem. J. 21:111 (1927).
Lewis, R. W., Comp. Biochem. Physiol. 19:363 (1966).
Murphy, R. C., “Oceanic Birds of South America,” Vol. 1, The Macmillan Co., New York, 1936, p. 473–474.
Challinor, C. J., R. J. Hamilton, and K. Simpson, Chem. Phys. Lipids 3:145 (1969).
Kolattukudy, P. E., Biochemistry 6:2705 (1967).
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An erratum to this article is available at http://dx.doi.org/10.1007/BF02532755.
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Nevenzel, J.C. Occurrence, function and biosynthesis of wax esters in marine organisms. Lipids 5, 308–319 (1970). https://doi.org/10.1007/BF02531462
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DOI: https://doi.org/10.1007/BF02531462