Advertisement

Journal of Chemical Ecology

, Volume 3, Issue 3, pp 309–319 | Cite as

Syn- andanti-phenylacetaldehyde oxime two novel testosterone-dependent mammalian metabolites

  • Amos B. SmithIII
  • Kevin J. Byrne
  • Gary K. Beauchamp
Article

Abstract

Domestic guinea pigs having high levels of circulating testosterone (i.e., males and castrate males receiving testosterone propionate injections) excrete in their urine equal amounts of both thesyn andanti isomers of phenylacetaldehyde oxime, while those guinea pigs having low testosterone titers (i.e., females, castrate males, and juveniles) excrete neither. These aldoximes were also detected in the urine of wild male guinea pigs. Radiolabeling studies in the domestic guinea pigs strongly suggest that these aldoximes are derived from phenylalanine. To our knowledge this is the first observation and isolation of phenylacetaldehyde oxime from a mammalian source. The significance of these components in phenylalanine metabolism as well as in guinea pig chemical communication is discussed.

Key words

chemical communication phenylalanine metabolism guinea pig urinary metabolites phenylacetaldehyde oxime 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Beauchamp, G.K. 1973. Attraction of male guinea pigs to conspecific urine.Physiol. Behav. 10:589–594.PubMedGoogle Scholar
  2. Beauchamp, G.K., andBerÜter, J. 1973. Source and stability of attractive components in guinea pigs (Cavia porcellus) urine.Behav. Biol. 9:43–47.PubMedGoogle Scholar
  3. Beauchamp, G.K.,Magnus, J.G.,Shmunes, N.T., andDurham, T. 1977. Effects of olfactory bulbectomy on social behavior of male guinea pigs(Cavia porcellus).J. Comp. Physiol. Psychol. In press.Google Scholar
  4. BerÜter, J., Beauchamp, G.K., andMuetterties, E.L. 1973. Complexity of chemical communication in mammals: Urinary components mediating sex discrimination by male guinea pigs.Biochem. Biophys. Res. Commun. 63:264–271.Google Scholar
  5. Birch, M.C. (ed.), 1974. Pheromones. Elsevier, New York.Google Scholar
  6. Brownlee, R.G., andSilverstein, R.M. 1968. A micro-preparative gas Chromatograph and a modified carbon skeleton determinator.Anal. Chem. 40:2077–2079.Google Scholar
  7. Conn, E.E. 1973. Biosynthesis of cyanogenic glycosides.Biochem. Soc. Symp. 38:277–302.Google Scholar
  8. Doffus, W. 1892. Uber die Configuration von Aldoximen.Ber. 25:1908–1936.Google Scholar
  9. Doty, R.L. (ed.). 1976. Mammalian Olfaction, Reproductive Processes and Behavior. Academic Press, New York.Google Scholar
  10. Gehrke, C.W., andLeimer, K. 1971. Trimethylsilylation of amino acids: Derivitization and chromatography.J. Chromatog. 57:219.Google Scholar
  11. Goldsmith, D., Becker, D., Sample, S., andDjerassi, C. 1966. Mass spectrometry in structural and stereochemical problems: A study of the fragmentation processes of Oximes.Tetrahedron Suppl. 7:145–173.Google Scholar
  12. Kindl, H., andUnderhill, E.W. 1968. Biosynthesis of mustard oil glucosides:n-Hydroxyphenylalanine, a precussor of glucotropaeolin and a substrate for enzymatic and nonenzymatic formation of phenylacelaldehyde oxime.Phytochemistry. 7:745–756.Google Scholar
  13. Mika, M., 1973. Mass spectral analysis of oxime derivatives. Ph.D. Thesis. University of Illinois. University Microfilms International, 74–27, 294.Google Scholar
  14. Preti, G.,Smith, A.B., III andBeauchamp, G. 1977. Chemical and behavioral complexity in mammalian chemical communication systems: Guinea pigs (Cavia porcellus), marmosets(Saguinus fuscicollis) and humans(Homo sapiens), in Müller-Schwarze and Mozell, (eds.). Chemical Signals in Vertebrates. In press.Google Scholar
  15. Smith, A.B., III,Byrne, K.J., andBeauchamp, G.K. 1975. Unpublished results.Google Scholar
  16. Stalling, D.L., Gerhke, C.W., andZumwalt, R.W. 1968. A new silylation reagent for amino acids. Bis(trimethylsilyl)trifluoroacetamide (BSAFA).Biochem. Biophys. Res. Commun. 31:616.PubMedGoogle Scholar
  17. Tapper, B.A., andButler, G.W. 1967. Biosynthesis of mustard oil glucosides: Conversion of phenylacetaldehyde oxide and 3-phenylpropionaldehyde oxime to glucotropaeolin and gluconasturtiin.Arch. Biochem. Biophys. 120:719–721.Google Scholar
  18. Underhill, E.W. 1967. Conversion of oximes to mustard oil glucosides (glucosinolates).Eur. J. Biochem. 2:61–63.PubMedGoogle Scholar
  19. Underhill, E.W., Wetter, L.R., andChisholm, M.D. 1973. Biosynthesis of glucosinolates.Biochem. Soc. Symp. 38:303–326.Google Scholar

Copyright information

© Plenum Publishing Corp. 1977

Authors and Affiliations

  • Amos B. SmithIII
    • 1
  • Kevin J. Byrne
    • 1
  • Gary K. Beauchamp
    • 1
  1. 1.The Monell Chemical Senses Center and The Department of ChemistryUniversity of PennsylvaniaPhiladelphia

Personalised recommendations