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Xenobiotica
the fate of foreign compounds in biological systems
Volume 37, 2007 - Issue 9
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Research Article

Pharmacokinetics of 1,8-cineole, a dietary toxin, in the brushtail possum (Trichosurus vulpecula): Significance for feeding

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Pages 903-922 | Received 20 Jun 2007, Accepted 12 Jul 2007, Published online: 22 Sep 2008

References

  • Boyle RR, McLean S. Constraint of feeding by chronic ingestion of 1,8-cineole in the brushtail possum (Trichosurus vulpecula). Journal of Chemical Ecology 2004; 30: 757–775
  • Boyle R, McLean S, Davies NW. Biotransformation of 1,8-cineole in the brushtail possum (Trichosurus vulpecula). Xenobiotica 2000; 30: 915–932
  • Boyle R, McLean S, Foley W, Davies NW, Peacock EJ, Moore B. Metabolites of dietary 1,8-cineole in the male koala (Phascolarctos cinereus). Comparative Biochemistry and Physiology C 2001; 129: 385–395
  • Boyle RR, McLean S, Brandon S, Pass GJ, Davies NW. Application of solid-phase microextraction to the quantitative analysis of 1,8-cineole in blood and expired air in a eucalyptus herbivore, the brushtail possum (Trichosurus vulpecula). Journal of Chromatography B — Analytical Technologies in the Biomedical and Life Sciences 2002; 780: 397–406
  • Boyle RR, McLean S, Brandon S, Wiggins N. Rapid absorption of dietary 1,8-cineole results in critical blood concentration of cineole and immediate cessation of eating in the common brushtail possum (Trichosurus vulpecula). Journal of Chemical Ecology 2005; 31: 2775–2790
  • Burritt EA, Banner RE, Provenza FD. Sagebrush ingestion by lambs: Effects of experience and macronutrients. Journal of Range Management 2000; 53: 91–96
  • Carman RM, Garner AC. 7,9-Dihydroxy-1,8-cineole and 2α,7-dihydroxy-1,8-cineole: Two new possum urinary metabolites. Australian Journal of Chemistry 1996; 49: 741–749
  • Carman RM, Garner AC, Klika KD. 2,9-dihydroxy-1,8-cineole and 2,10-dihydroxy-1,8-cineole — two new possum urinary metabolites. Australian Journal of Chemistry 1994; 47: 1509–1521
  • Carman RM, Klika KD. Partially racemic compounds as brushtail possum urinary metabolites. Australian Journal of Chemistry 1992; 45: 651–657
  • Carman RM, Rayner AC. Chiral 2 alpha,4-dihydroxy-1,8-cineole as a possum urinary metabolite. Australian Journal of Chemistry 1996; 49: 1–6
  • Dearing MD, Foley WJ, McLean S. The influence of plant secondary metabolites on the nutritional ecology of herbivorous terrestrial vertebrates. Annual Review of Ecology Evolution and Systematics 2005; 36: 169–189
  • Dearing MD, Mangione AM, Karasov WH. Diet breadth of mammalian herbivores: Nutrient versus detoxification constraints. Oecologia 2000; 123: 397–405
  • Duisken M, Sandner F, Blomeke B, Hollender J. Metabolism of 1.8-cineole by human cytochrome P450 enzymes: Identification of a new hydroxylated metabolite. Biochimica et Biophysica Acta — General Subjects 2005; 1722: 304–311
  • Duncan AJ, Hartley SE, Iason GR. The effect of monoterpene concentrations in sitka spruce (Picea sitchensis) on the browsing behaviour of red deer (Cervus elaphus). Canadian Journal of Zoology 1994; 72: 1715–1720
  • Dutta S, Ebling WF. Formulation-dependent pharmacokinetics and pharmacodynamics of propofol in rats. Journal of Pharmacy and Pharmacology 1998; 50: 37–42
  • Dziba LE, Hall JO, Provenza FD. Feeding behavior of lambs in relation to kinetics of 1,8-cineole dosed intravenously or into the rumen. Journal of Chemical Ecology 2006; 32: 391–408
  • Falk AA, Hagberg MT, Lof AE, Wigaeushjelm EM, Zhiping W. Uptake, distribution and elimination of alpha-pinene in man after exposure by inhalation. Scandinavian Journal of Work Environment and Health 1990; 16: 372–378
  • Falkfilipsson A, Lof A, Hagberg M, Hjelm EW, Wang ZP. d-Limonene exposure to humans by inhalation — uptake, distribution, elimination, and effects on the pulmonary-function. Journal of Toxicology and Environmental Health 1993; 38: 77–88
  • Foley WJ, Iason GR, McArthur C. Role of plant secondary metabolites in the nutritional ecology of mammalian herbivores: How far have we come in 25 years? In Nutritional ecology of herbivores. Proceedings of the 5th International Symposium on the Nutrition of Herbivores, H-JG Jung, GC Fahey. American Society of Animal Science, Savoy, IL 1999; 130–209
  • Fraenkel GS. Raison d’être of secondary plant substances. Science 1959; 129: 1466–1470
  • Freeland WJ, Janzen DH. Strategies in herbivory by mammals: The role of plant secondary compounds. American Naturalist 1974; 108: 268–289
  • Gonzalez FJ, Nebert DW. Evolution of the P450 gene superfamily: Animal–plant ‘warfare’, molecular drive and human genetic differences in drug oxidation. Trends in Genetics 1990; 6: 182–186
  • Griffin S, Wyllie SG, Markham J. Determination of octanol–water partition coefficient for terpenoids using reversed-phase high-performance liquid chromatography. Journal of Chromatography A 1999; 864: 221–228
  • Hellriegel ET, Bjornsson TD, Hauck WW. Interpatient variability in bioavailability is related to the extent of absorption: Implications for bioavailability and bioequivalence studies. Clinical Pharmacology and Therapeutics 1996; 60: 601–607
  • Jager W, Nasel B, Nasel C, Binder R, Stimpfl T, Vycudilik W, Buchbauer G. Pharmacokinetic studies of the fragrance compound 1,8-cineol in humans during inhalation. Chemical Senses 1996; 21: 477–480
  • Jenner PM, Hagan EC, Taylor JM, Cook EL, Fitzhugh OG. Food flavourings and compounds of related structure i. Acute oral toxicity. Food and Cosmetic Toxicology 1964; 2: 327–343
  • Karban R, Agrawal AA. Herbivore offense. Annual Review of Ecology and Systematics 2002; 33: 641–664
  • Knibbe CAJ, Voortman HJ, Aarts L, Kuks PFM, Lange R, Langemeijer HJM, Danhof M. Pharmacokinetics, induction of anaesthesia and safety characteristics of propofol 6% sazn vs. propofol 1% sazn and diprivan (r)-10 after bolus injection. British Journal of Clinical Pharmacology 1999; 47: 653–660
  • Kohlert C, Van Rensen I, Marz R, Schindler G, Graefe Eu, Veit M. Bioavailability and pharmacokinetics of natural volatile terpenes in animals and humans. Planta Medica 2000; 66: 495–505
  • Kovar KA, Gropper G, Friess D, Ammon PT. Blood levels of 1,8-cineole and locomotor activity of mice after inhalation and oral administration of rosemary oil. Planta Medica 1987; 53: 315–318
  • Lawler IR, Stapley J, Foley WJ, Eschler BM. Ecological example of conditioned flavor aversion in plant–herbivore interactions: Effect of terpenes of Eucalyptus leaves on feeding by common ringtail and brushtail possums. Journal of Chemical Ecology 1999; 25: 401–415
  • Levitt MD, Levitt DG. Use of a two-compartment model to assess the pharmacokinetics of human ethanol metabolism. Alcoholism — Clinical and Experimental Research 1998; 22: 1680–1688
  • Lewis DF, Watson E, Lake BG. Evolution of the cytochrome P450 superfamily: Sequence alignments and pharmacogenetics. Mutation Research 1998; 410: 245–270
  • Lin JH, Yamazaki M. Role of p-glycoprotein in pharmacokinetics — clinical implications. Clinical Pharmacokinetics 2003; 42: 59–98
  • McDonald IR, Than KA. Effect of cortisol on utilization and hepatic release of glucose in marsupial brush-tailed opossum, Trichosurus vulpecula. Journal of Endocrinology 1976; 68: 257–264
  • McLean S, Duncan AJ. Pharmacological perspectives on the detoxification of plant secondary metabolites: Implications for ingestive behavior of herbivores. Journal of Chemical Ecology 2006; 32: 1213–1228
  • Miyazawa M, Shindo M, Shimada T. Oxidation of 1,8-cineole, the monoterpene cyclic ether originated from Eucalyptus polybractea, by cytochrome P450 3a enzymes in rat and human liver microsomes. Drug Metabolism and Disposition 2001; 29: 200–205
  • Musser JB, Fontana JL, Mongan PD. The anesthetic and physiologic effects of an intravenous administration of a halothane lipid emulsion (5% vol/vol). Anesthesia and Analgesia 1999; 88: 671–675
  • Norberg A, Jones AW, Hahn RG, Gabrielsson JL. Role of variability in explaining ethanol pharmacokinetics: Research and forensic applications. Clinical Pharmacokinetics 2003; 42: 1–31
  • Pass GJ, McLean S. Inhibition of the microsomal metabolism of 1,8-cineole in the common brushtail possum (Trichosurus vulpecula) by terpenes and other chemicals. Xenobiotica 2002; 32: 1109–1126
  • Pass GJ, McLean S, Stupans I. Induction of xenobiotic metabolising enzymes in the common brushtail possum, Trichosurus vulpecula, by Eucalyptus terpenes. Journal of Comparative Biochemistry and Physiology 1999; 124: 239–246
  • Pass GJ, McLean S, Stupans I, Davies N. Microsomal metabolism of the terpene 1,8-cineole in the common brushtail possum (Trichosurus vulpecula), koala (Phascolarctos cinereus), rat and human. Xenobiotica 2001; 31: 205–221
  • Patel S, Wiggins J. Eucalyptus oil poisoning. Archives of Disease in Childhood 1980; 55: 405–406
  • Richardson ML. The dictionary of substances and their effects. Royal Society of Chemistry, Cambridge 1993; 2
  • Rowland M, Tozer TN. Clinical pharmacokinetics — concepts and applications3rd. Lea & Febiger, Philadelphia, PA 1995
  • Santos FA, Silva RM, Tome AR, Rao VSN, Pompeu MML, Teixeira MJ, De Freitas LAR, De Souza VL. 1,8-cineole protects against liver failure in an in-vivo murine model of endotoxemic shock. Journal of Pharmacy and Pharmacology 2001; 53: 505–511
  • Sorensen JS, Dearing MD. Efflux transporters as a novel herbivore countermechanism to plant chemical defenses. 2006; 32: 1181–1196
  • Southwell IA, Maddox GDA, Zalucki MP. Metabolism of 1,8-cineole in tea tree (Melaleuca alternifolia and M. linariifolia) by pyrgo beetle (Paropsisterna tigrina). Journal of Chemical Ecology 1995; 21: 439–453
  • Sweet DV. Registry of toxic effects of chemical substances 1985–86 edition. US Department of Health and Human Services, Cincinnati, OH 1987; 3A
  • Tam YK. Individual variation in 1st-pass metabolism. Clinical Pharmacokinetics 1993; 25: 300–328
  • Tibballs J. Clinical effects and management of eucalyptus oil ingestion in infants and young children. Medical Journal of Australia 1995; 163: 177–180
  • Webb NJA, Pitt WR. Eucalyptus oil poisoning in childhood: 41 cases in south-east Queensland. Journal of Paediatric Child Health 1993; 29: 368–371
  • Whitman BW, Ghazizadeh H. Eucalyptus oil: Therapeutic and toxic aspects of pharmacology in humans and animals. Journal of Paediatric Child Health 1993; 29: 368–371
  • Wiggins NL, McArthur C, McLean S, Boyle R. Effects of two plant secondary metabolites, cineole and gallic acid, on nightly feeding patterns of the common brushtail possum. Journal of Chemical Ecology 2003; 29: 1447–1464
  • Zimmermann T, Seiberling M, Thomann P, Karabelnik D. Evaluation of the relative bioavailablility and the pharmacokinetics of myrtol standardized. Arzneimittel Forschung/Drug Research 1995; 45: 1198–1201

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