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Sulfur Compounds in Mustelids

  • Kenneth K. Andersen
  • David T. Bernstein

Abstract

Secondary chemicals, especially alkaloids and terpenes isolated from plants, have interested chemists for many decades, yet only comparatively recently have their important roles in ecology been realized. They are no longer incorrectly considered to be just metabolic by-products.1 Investigations of secondary compounds produced by mammals have a long history, but are not numerous in comparison to the studies of substances isolated from plants or even insects. Early studies on mammalian secretions were stimulated primarily by commercial concern with perfumes, whereas current research is motivated mostly by the great interest in chemical ecology, in particular by the influence these secretions acting as chemical signals have on animal behavior. Recent advances in the methodology of isolation and identification of small quantities of low molecular weight volatile compounds coincide with this growth of interest and have resulted in a dramatic increase in the number of mammalian secondary chemicals which have been identified. For the most part, mammalian secondary compounds are volatile and received by olfaction.2 Since the odors of low molecular weight divalent sulfur compounds are usually very intense and distinct to humans, and apparently to other mammals as well, it is not surprising that such compounds, many examples of which are found in plants, are also represented in mammalian secretions.3,4 Compound 1 was found in the vaginal secretion of the golden hamster5, 2 in the anal scent gland of the striped hyena6, and 3 and 4 in red fox urine.7

Keywords

Sulfur Compound Vaginal Secretion Anal Gland Mustela Vison Striped Skunk 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    J. B. Harborne, Chemosysternatics and coevolution, Pure and Appl. Chem. 49: 1403 (1977).Google Scholar
  2. 2.
    D. Miiller-Schwarze and M. M. Mozell, “Chemical Signals in Vertebrates,” Plenum Press, New York (1977).Google Scholar
  3. 3.
    A. Kjaer, Low molecular weight sulphur-containing compounds in nature: a survey, Pure and Appl. Chem. 49: 137 (1977).Google Scholar
  4. 4.
    G. Ohloff and I. Flament, The role of heteroatomic substances in the aroma compounds of food stuffs, in “Progress in the Chemistry of Organic Natural Products,” vol. 36, W. Herz, H. Grisebach, and G. W. Kirby, eds., Springer-Verlag, Vienna (1979).Google Scholar
  5. 5.
    A. G. Singer, W. C. Agosta, R. J. O’Connell, C. Pfaffmann, D. V. Bowen, and F. H. Field, Dimethyl disulfide: an attractant pheromone in hamster vaginal secretion, Science 191: 948 (1976).PubMedCrossRefGoogle Scholar
  6. 6.
    J. W. Wheeler, D. W. von Endt, and C. Wemmer, 5-Thiomethylpentan-2,3-dione: a unique natural product from the striped hyena, J. Am. Chem. Soc. 97; 441 (1975).CrossRefGoogle Scholar
  7. 7.
    S. R. Wilson, M. Carmack, M. Novotny, J. W. Jorgenson, and W. K. Whitten, 3-Isopentenyl methyl sulfide. A new terpenoid in the scent mark of the red fox (Vulpes vulpes), J. Org. Chem. 43: 4676 (1978).CrossRefGoogle Scholar
  8. 8.
    K. K. Andersen and D. T. Bernstein, Some chemical constituents of the scent of the striped skunk (Mephitis mephitis)J. Chem. Ecol. 1: 493 (1975).Google Scholar
  9. 9.
    B. J. Verts, “The Biology of the Striped Skunk,” The University of Illinois Press, Chicago (1967).Google Scholar
  10. 10.
    T. F. Aldrich, A chemical study of the secretion of the anal glands of Mephitis mephitica (common skunk) with remarks on the physiological properties of this secretion, J. Exp. Med. 1: 323 (1896).PubMedCrossRefGoogle Scholar
  11. 11.
    G. A. Fester and F. A, Bertuzzi, La secreción del zorrino, Rev. Fac. Quim. Ind. Agr. Univ. Mac, litoral 5: 85 (1937).Google Scholar
  12. 12.
    E. Beckmann, Ueber das Drüsensecret des Stinkdaches, Pharm. Zentralhalle Dsch. 37: 557 (1896).Google Scholar
  13. 13.
    H. Schildknecht, I. Wilz, F. Enzmann, N. Grund, and M. Ziegler, Mustelan, the malodorous substance from the anal gland of the mink (Mustela vison) and the polecat (Mustela putorius), Ang. Chem. Int. Ed. Engl. 15:242 (1976).Google Scholar
  14. 14.
    D. R. Crump, The major malodorous substance from the anal gland of the stoat (Mustela erminea), Tetrahedron Lett. 5233 (1978).Google Scholar
  15. 15.
    K. K. Andersen and D. T. Bernstein, 1-Butanethiol and the striped skunk, J. Chem. Ed. 55:159 (1978).Google Scholar
  16. 16.
    V. E. Sokolov and I. M. Khorlina, Pheromones of mammals: study of the composition of volatile acids in vaginal discharge of mink (Mustela vison Bris.), Dokl, Akad, Nauk SSR 228:225 (1976) in Chem. Abs. 85: 60288q (1976).Google Scholar
  17. 17.
    D. T. Bernstein, Chemical constituents of the anal glands of the striped skunk (Mephitis mephitis) and the North American mink (Mustela vison), Ph.D. thesis, University of New Hampshire, Durham, New Hampshire, 1979.Google Scholar
  18. 18.
    G. E. Svendsen and J. D. Jollick, Bacterial contents of the anal and castor glands of beaver, J. Chem. Ecol. 4: 563 (1978).CrossRefGoogle Scholar
  19. 19.
    E. S. Albone and G. C. Perry, Anal sac secretion of the red fox,Vulpes vulpes: volatile fatty acids and diamines: Implications for a fermentation hypothesis of chemical recognition, J. Chem. Ecol. 2: 101 (1975).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1980

Authors and Affiliations

  • Kenneth K. Andersen
    • 1
  • David T. Bernstein
    • 1
  1. 1.Department of ChemistryUniversity of New HampshireDurhamUSA

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