Fate of the dietary terpene, p-cymene, in the male koala

Journal of Chemical Ecology

Volumn 26, Issue 5, 2000, Pages 1095-1111

  Boyle, Rebecca ^a   McLean, Stuart ^a   Foley, William J ^b   Moore, Ben D ^b   Davies, Noel W ^c   Brandon, Sue ^a  

^a UNIVERSITY OF TASMANIA   (Australia)

^b AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^c UNIVERSITY OF TASMANIA   (Australia)

Author keywords

Eucalyptus; Koala; Metabolism. detoxification; P cymene; Phascolarctos cinereus (Goldfuss); Terpene

Indexed keywords

TERPENE;

ARTICLE; CONCENTRATION (PARAMETERS); FECES ANALYSIS; FOOD INTAKE; METABOLISM; NONHUMAN; PLANT; URINE LEVEL;

EID: 0034035417     PISSN: 00980331     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1005482207995     Document Type: Article

References (26)

1. AMMON, D. G., BARTON, A. F., CLARKE, D. A., and TJANDRA, J. 1985. Rapid and accurate determination of terpenes in the leaves of Eucalyptus species. Analyst 110:921-924.
2. ALVARES, A. P., and PRATT, W. B. 1990. Pathways of drug metabolism, pp. 365-422, in W. B. Pratt and P. Taylor (eds.). Principles of Drug Action - The Basic of Pharmacology. Churchill Livingston, New York.
3. BLUMENKRANTZ, N., and ASBOE-HANSEN, G. 1973. New method for quantitative determination of uronic acids. Anal. Biochem. 54:484-489.
4. BOYLE, R., MCLEAN, S., FOLEY, W. J., and DAVIES, N. W. 1999. Comparative metabolism of the dietary terpene, p-cymene, in generalist and specialist folivorous marsupials. J. Chem. Ecol. 26:2109-2126.
5. BULL, S. D., CARMAN, R. M., CARRICK, F. N., and KLIKA, K. D. 1993. 7-Hydroxy-1,8-cineole and 7-cineolic acid. Two new possum urinary metabolites. Aust. J. Chem. 46:441-447.
6. CARMAN, R. M., and GARNER, A. C. 1996. 7,9-Dihydroxy-1,8-cineole and 2α,7-dihydroxy-1,8-cineole: two new possum urinary metabolites. Aust. J. Chem. 49:741-749.
7. CARMAN, R. M., and KLIKA, K. D. 1992. Partially racemic compounds as brushtail possum urinary metabolites. Aust. J. Chem. 45:651-657.
8. CARMAN, R. M., and RAYNER, A. C. 1994. 2-α,4-Dihydroxy-1,8-cineole - a new possum urinary metabolites. Aust. J. Chem. 47:2087-2097.
9. CARMAN, R. M., GARNER, A. C., and KLIKA, K. D. 1994. 2,9-Dihydroxy-1,8-cineole and 2,10-dihydroxy-1,8-cineole - two new possum urinary metabolite. Aust. J. Chem. 47:1509-1521.
10. EBERHARD, I. H., MCNAMARA, J., PEARSE, R. J., and SOUTHWELL, I. A. 1975. Ingestion and excretion of Eucalyptus punctata D.C. and its essential oils by the koala. Phascolarctos cinereus (Goldfuss). Aust. J. Zool. 23:169-179.
11. FREELAND, W. J. 1991. Plant secondary metabolites: biochemical coevolution with herbivores, pp. 61-81, in R. T. Palo and C. T. Robbins (eds.). Plant Defenses Against Mammalian Herbivores. CRC Press, Boca Raton, Florida.
12. FREELAND, W. J., and JANZEN, D. H. 1974. Strategies in herbivory by mammals: The role of plant secondary compounds. Am. Nat. 108:268-289.
13. ISHIDA, T., ASAKAWA, Y., TAKEMOTO, T., and ARATANI, T. 1981. Terpenoid biotransformation in mammals iii: Biotransformation of α-pinene, β-pinene, pinane, 3-carene, carane, myrcene, and p-cymene in rabbits. J. Pharm. Sci. 70:406-415.
14. ISHIDA, T., ASAKAWA, Y., and TAKEMOTO, T. 1982. Metabolism of myrtenal, perilla aldehyde and dehydroabietic acid in rabbits. Hiroshima Kogyo Daigaku Kenkyu Kiyo 16:79-91.
15. ISHIDA, T., TOYOTA, M., and ASAKAWA, Y. 1989. Terpenoid biotransformation in mammals. V. Metabolism of (+)-citronellal, (±)-7-hydroxycitronellal, citral, (-)-perillaldehyde, (-)-myrtenal, cuminaldehyde, thujone, and (±)-carvone in rabbits. Xenobiotica 19:843-855.
16. LAWLER, I. R., FOLEY, W. J., ESCHLER, B. M., PASS, D. M., and HANDASYDE, K. 1998. Intraspecific variation in Eucalyptus secondary metabolites determines food intake by folivorous marsupials. Oecologia 116:160-169.
17. MATSUMOTO, T., ISHIDA, T., YOSHIDA, T., TERAO, H., TAKEDA, Y., and ASAKAWA, Y. 1992. The enantioselective metabolism of p-cymene in rabbits. Chem. Pharm. Bull. 40:1721-1726.
18. MCLEAN, S., FOLEY, W. J., DAVIES, N. W., BRANDON, S., DUO, L., and BLACKMAN, A. J. 1993. Metabolic fate of dietary terpenes from Eucalyptus radiata in common ringtail possums (Pseudocheirus peregrinus). J. Chem. Ecol. 19:1625-1643.
19. MORROW, P. A., and Fox, L. R. 1980. Effects of variation in Eucalyptus essential oil yield on insect growth and grazing damage. Oecologia 45:209-219.
20. NIST. 1998. NIST Mass Spectral Library. US Department of Commerce, Gaithersburg, Maryland.
21. SOUTHWELL, I. A. 1973. Variation in the leaf oil of Eucalyptus punctata. Phytochemistry 12:1341-1343.
22. SOUTHWELL, I. A. 1975. Essential oil metabolism in the koala (iii) novel urinary monoterpene lactones. Tetrahedron 24:1885-1888.
23. SOUTHWELL, I. A., FLYNN, T. M., and DEGABRIELE, R. 1980. Metabolism of α- and β-pinene, p-cymene and 1,8-cineole in the brushtail possum, Trichosurus vulpecula. Xenobiotica 10:17-23.
24. STUPANS, I., KONG, S., KIRLICH, A., MURRAY, M., BAILEY, E. L., JONES, B. R., and MCKINNON, R. A. 1999. Hepatic microsomal enzyme activity in the koala and tammar wallaby: high 17β-hydroxysteroid oxidoreductase activity in koala liver microsomes. Comp. Biochem. Physiol. Part C 123(1):67-73.
25. VOGEL, A. I. 1959. A Textbook of Practical Organic Chemistry Including Qualitative Organic Analysis, 3rd ed. Longmans, Green, London.
26. WALDE, A., VE, B., and SCHELINE, R. R. 1983. p-Cymene metabolism in rats and guinea pigs. Xenobiotica 13:503-512.