Microsomal metabolism of the terpene 1,8-cineole in the common brushtail possum (Trichosurus vulpecula), koala (Phascolarctos cinereus), rat and human

References

• AUSTIN, C. A., SHEPHARD, E. A., PIKE, S. F., RABIN, B. R. and PHILLIPS, I. R., 1988, The effect of terpenoid compounds on cytochrome P-450 levels in rat liver. Biochemical Pharmacology, 37, 2223–2229.
   PubMed Web of Science ®Google Scholar
• BARNES, W., 1996, Eucalyptus oil poisoning in children. Australian Journal of Emergency Care, 3, 15–20. BOLAND, K. J. and BROPHY, J. J., 1991, Eucalyptus Leaf Oils: Use, Chemistry, Distillation and Marketing (Melbourne: Inkata).
   Google Scholar
• BOYLE, R. R., 1999, The metabolic fat of dietary terpenes in folivorous marsupials, PhD thesis, School of Pharmacy, University of Tasmania, Hobart.
   Google Scholar
• BOYLE, R. R, MCLEAN, S., FOLEY, W. J., MOORE, B. D., DAvrEs, N. W. and BRANDON, S., 2000a, Fate of the dietary terpene, p-cymene, in the male koala. Journal of Chemical Ecology, 25, 1095–1111.
   Web of Science ®Google Scholar
• BOYLE, R. R., MCLEAN, S. and DAvrEs, N., 2000b, Biotransformation of 1,8-cineole in the brushtail possum (Trichosurus vulpecula). Xenobiotica, 30, 915–932.
   PubMed Web of Science ®Google Scholar
• BOYLE, R. R., MCLEAN, S., FOLEY, W. J. and DAvrEs, N., 1999, Comparative metabolism of dietary terpene, p-cymene, in generalist and specialist folivorous marsupials. Journal of Chemical Ecology, 25, 2109–2126.
   Web of Science ®Google Scholar
• BRATTSTEN, L. B., WILKINSON, C. F. and EISNER, T., 1977, Herbivore-plant interactions: mixed-function oxidases and secondary plant substances. Science, 196, 1349–1352.
   PubMed Web of Science ®Google Scholar
• 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. Australian Journal of Chemistry, 46, 441–447.
   Web of Science ®Google Scholar
• CARMAN, R. M. and FLETCHER, M. T., 1984, The isomeric 1,3,3-trimethy1-2-oxabicyclo-[2.2.2]octan-6-ols (2 -hydroxy -1,8 -cineoles). Australian Journal of Chemistry, 37, 1117–1122.
   Web of Science ®Google Scholar
• CARMAN, R. M. and GARNER, A. C., 1996, 7,9-Hydroxy-1,8-cineole and 2a,7-dihydroxy-1,8-cineole: two new possum urinary metabolites. Australian Journal of Chemistry, 49, 741–749.
   Web of Science ®Google Scholar
• CARMAN, R. M. and KLIICA, K. D., 1992, Partially racemic compounds as brushtail possum urinary metabolites. Australian Journal of Chemistry, 45, 651–657.
   Web of Science ®Google Scholar
• CARMAN, R. M. and RAYNER, A. C., 1994, 2a,4-Dihydroxy-1,8-cineole. A new possum urinary metabolite. Australian Journal of Chemistry, 47, 2087–2097.
   Web of Science ®Google Scholar
• CHADHA, A. and MADHAVA MADYASTHA, K., 1984, Metabolism of geraniol and linalool in the rat and effects on liver and lung microsomal enzymes. Xenobiotica, 14, 365–374.
   PubMed Web of Science ®Google Scholar
• CEN-ri, D. L., LEMELIN, M. A. and CHRISTIAN, J., 1976, Induction of liver microsomal mixed-function oxidases by volatile hydrocarbons. Biochemical Pharmacology, 25, 100–103.
   Google Scholar
• COHEN, M. B., BERENBAUM, M. R. and SCHULER, M. A., 1989, Induction of cytochrome P450-mediated detoxification of xanthotoxin in the black swallowtail. Journal of Chemical Ecology, 15, 2347–2355.
   PubMed Web of Science ®Google Scholar
• CORK, S. J., HUME, I. D. and DAMSON, T. J., 1983, Digestion and metabolism of a natural foliar diet (Eucalyptus punctata) by an arboreal marsupial, the koala (Phascolarctos cinereus). Journal of Comparative Physiology ( B), 153, 181–190.
   Google Scholar
• DARBEN, T., COMINOS, B. and LEE, C. T., 1998, Topical Eucalyptus oil poisoning. Australasian Journal of Dermatology, 39, 265–267.
   PubMedGoogle Scholar
• DE-OLIVEIR A. C. A. X., FIDALGO-NETO, A. A. and PAUMGARTTEN, F. J. R., 1999, In vitro inhibition of liver monooxygenases by [3-ionone, 1,8-cineole, (-)-menthol and terpineol. Toxicology, 135, 33–41.
   Google Scholar
• DE-OLIVEIR A. C. A. X., RIBEIRO-PINTO, L. F., OTTO, S. S., GONCALVES, A. and PAUMGARTTEN, F. J. R., 1997, Induction of liver monoxygenases by [3-myrcene. Toxicology, 124, 135–140.
   Google Scholar
• EBERHARD, I. H., MCNAMARA, J., PEARSE, R. J. and SOUTHWELL, I. A., 1975, Ingestion and excretion of Eucalyptus punctata D. C. and its essential oil by the koala, Phascolarctos cinereus (Goldfuss). Australian Journal of Zoology, 23, 169–179.
   Web of Science ®Google Scholar
• FLYNN, T. M. and SOUTHWELL, I. A., 1979, 1,3-Dimethy1-2-oxabicyclo[2,2,2]-octane-3-methanol and 1,3-dimethy1-2-oxa-bicyclo[2,2,2]octane-3-carboxyl acid, urinary metabolites of 1,8-cineole. Australian Journal of Chemistry, 32, 2093–2095.
   Web of Science ®Google Scholar
• FREELAND, W. J. and JANZEN, D. H., 1974, Strategies in herbivory by mammals: the role of plant secondary compounds. American Naturalist, 108, 269–287.
   Web of Science ®Google Scholar
• FREELAND, W. J. and WINTER, J. W., 1975, Evolutionary consequences of eating: Trichosurus vulpecula and the genus Eucalyptus. Journal of Chemical Ecology, 1, 439–455.
   Web of Science ®Google Scholar
• FRIGERIO, A., PALADINO, R., TESTONI, G., COBELLI, L., PASTORELLO, L. and ToLENTIN0, D., 1985, 1,8-Cineole (eucalyptol) metabolites in rat. Spectroscopy International Journal, 4, 43–56.
   Google Scholar
• FuRIA, T. E. (ed.), 1972, CRC Handbook of Food Additives, 2nd edn (New York: CRC Press).
   Google Scholar
• Gum, F. W. and SCROGGIE, J. G., 1965, Eucalyptus oil poisoning treated by dialysis and mannitol infusion, with an appendix on the analysis of biological fluids for alcohol and eucalyptol. Australasian Annals of Medicine, 14, 238–249.
   PubMedGoogle Scholar
• HIROI, T., MIYAZAKI, Y., KOBAYASHI, Y., ImAoRA, S. and FUNAE, Y., 1995, Induction of hepatic P450s in rat by essential wood and leaf oils. Xenobiotica, 25, 457–467.
   PubMed Web of Science ®Google Scholar
• HUE, I. D., 1982, Digestive Physiology and Nutrition of Marsupials (Melbourne: Cambridge University Press).
   Google Scholar
• HUE, I. D., BLADON, R. V. and SORA N., 1996, Seasonal changes in digestive performance of common ringtail possums (Pseudocheirus peregrinus) fed Eucalyptus foliage. Australian Journal of Zoology, 44, 327–336.
   Web of Science ®Google Scholar
• Jmu, A., BIANCHETTI, A. and PRESTINI, P. E., 1969, Effect of essential oils on drug metabolism. Biochemical Pharmacology, 18, 2081–2085.
   PubMed Web of Science ®Google Scholar
• Jmu, A. and BRIATICO, G., 1973, Short Communications: Effect of eucalyptol on microsomal enzyme activity of foetal and newborn rats. Biochemical Pharmacology, 22, 543–544.
   PubMed Web of Science ®Google Scholar
• KELLY, S. With CHIPPENDALE, G. M. and JOHNSTON, R. D., 1969, Eucalypts (Melbourne: Nelson). KERLE, J. A., 1984, Variation in the ecology of Trichosurus vulpecula: its adaptive significance. In A. P. Smith and I. D. Hume (eds), Possums and Gliders (Sydney: Surrey Beatty), pp. 115–125.
   Google Scholar
• LOWRY, O. H., ROSENBROUGH, N. J., FARR, A. L. and RANDALL, R. J., 1951, Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry, 193, 265–275.
   PubMed Web of Science ®Google Scholar
• MACLENNAN, D. G., 1984, The feeding behaviour and activity patterns of the brushtail possum, Trichosurus vulpecula, in open eucalypt woodland in southeast Queensland, in A. P. Smith and I. D. Hume (eds), Possums and Gliders (Sydney: Surrey Beatty), pp. 155–161.
   Google Scholar
• MACRAE, I. C., ALBERTS, V., CARMAN, R. M. and SHAW, I. M., 1979, Products of 1,8-cineole oxidation by a Pseudomonad. Australian Journal of Chemistry, 32, 917–922.
   Web of Science ®Google Scholar
• MADYASTHA, K. M. and CHADH A., 1986, Metabolism of 1,8-cineole in rat: its effects on liver and lung microsomal cytochrome P450 systems. Bulletin of Environmental and Contamination Toxicology, 37, 759–766.
   PubMed Web of Science ®Google Scholar
• MCLEAN, S. and FOLEY, W. J., 1997, Metabolism of Eucalyptus terpenes by herbivorous marsupials. Drug Metabolism Reviews, 29, 213–218.
   PubMed Web of Science ®Google Scholar
• 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). Journal of Chemical Ecology, 19, 1625–1643.
   PubMed Web of Science ®Google Scholar
• MIYAZAWA, M., KAMEOKA, H., MORINAGA, K., NEGORO, K. and MURA, N., 1989, Hydroxycineole: four new metabolites of 1,8-cineole in rabbits. Journal of Agriculture and Food Chemistry, 37, 222–226.
   Web of Science ®Google Scholar
• MIYAZAWA, M., WADA, T. and KAMEOKA, H., 1996, Biotransformation of a-terpinene in common cutworm larvae (Spodoptera litura Fabricius). Journal of Agriculture and Food Chemistry, 44, 2889–2893.
   Web of Science ®Google Scholar
• MIYAZAWA, M., WADA, T. and KAMEOKA, H., 1998, Biotransformation of (±)- and (-)-limonene by the larvae of common cutworm (Spodoptera litura). Journal of Agriculture and Food Chemistry, 46, 300–303.
   PubMed Web of Science ®Google Scholar
• PASS, G. J., MCLEAN, S. and STUPANS, I., 1999, Induction of xenobiotic metabolising enzymes in the common brushtail possum, Trichosurus vulpecula, by Eucalyptus terpenes. Comparative Biochemical Physiology (C), 124, 239–246.
   PubMed Web of Science ®Google Scholar
• PATEL, S. and WIGGINS, J., 1980, Eucalyptus oil poisoning. Archives of Diseases of the Child, 55, 405-406P>. REYNOLDS, J. E. F. (ed.), 1996, Martindale: The Extra Pharmacopoeia, 31st edn (London: Pharmaceutical Press).
   Google Scholar
• SCOTT, J. G., Liu, N. and WEN, Z., 1998, Insect cytochromes P450: diversity, insecticide resistance and tolerance to plant toxins. Comparative Biochemical Physiology (C), 121, 147–155.
   PubMed Web of Science ®Google Scholar
• Smuru, G., STUBBINS, M. J., HARRIES, L. W. and WOLF, C. R., 1998, Molecular genetics of the human cytochrome P450 monooxygenase superfamily. Xenobiotica, 28, 1129–1165.
   PubMed Web of Science ®Google Scholar
• SOUTHWELL, I. A., FLYNN, T. M. and DEGABRIELE, R., 1980, Metabolism of a- and [3-pinene, p-cymene and 1,8-cineole in the brushtail possum, Trichosurus vulpecula. Xenobiotica, 10, 17–23.
   PubMed Web of Science ®Google Scholar
• SOUTHWELL, I. A., MADDOX, C. D. A. and ZALUCKI, M. P., 1995, Metabolism of 1,8-cineole in tea tree (Melaleuca alternifolia and M. linariifolia) by pyrgo beetle (Paropsisterna tigrina). Journal of Chemical Ecology, 21, 439–453.
   Google Scholar
• SPOERKE, D. G., VANDENBERG, S. A., SMOLINSKE, S. C., Kumu, K. and RUMACK, B. H., 1989, Eucalyptus oil: 14 cases of exposure. Veterinary and Human Toxicology, 31, 166–168.
   PubMedGoogle Scholar
• STONE, C. and BACON, P. E., 1994, Relationships among moisture stress, insect herbivory, foliar cineole content and the growth of river red gum Eucalyptus camaldulensis. Journal of Applied Ecology, 31, 604–612.
   Web of Science ®Google Scholar
• STUPANS, I., KONG, S., KIRLICH, A., MURRAY, M., BAILEY, E. L., Jos, B. R. and MCKINNON, R. A., 1999, Hepatic microsomal enzyme activity in the koala and tammar wallaby: high 17 [3-hydroxysteroid activity in koala liver microsomes. Comparative Biochemical Physiology (C), 123, 67–73.
   PubMed Web of Science ®Google Scholar
• STUPANS, I., RICHARDS, D. A. and MCCLURE, M. T., 1995, Effects of 5-fluorouracil treatment on rat liver microsomal enzymes. Xenobiotica, 25, 1–8.
   PubMed Web of Science ®Google Scholar
• WALDE, A., VE, B., SCHELINE, R. R. and MONGE, P., 1983, p-Cymene metabolism in rats and guinea-pigs. Xenobiotica, 13, 503–512.
   PubMed Web of Science ®Google Scholar
• WEBB, N. J. A. and PITT, W. R., 1993, Eucalyptus oil poisoning in childhood - 41 cases in south-east Queensland. Journal of Paediatric and Child Health, 29, 368–371.
   Google Scholar