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Xenobiotica
the fate of foreign compounds in biological systems
Volume 30, 2000 - Issue 9
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Research Article

Biotransformation of 1,8-cineole in the brushtail possum (Trichosurus vulpecula)

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Pages 915-932 | Published online: 22 Sep 2008

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José Fernando Rinaldi de Alvarenga, Brunna Genaro, Bruna Lamesa Costa, Eduardo Purgatto, Claudine Manach & Jarlei Fiamoncini. (2023) Monoterpenes: current knowledge on food source, metabolism, and health effects. Critical Reviews in Food Science and Nutrition 63:10, pages 1352-1389.
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S. McLean, R. R. Boyle, S. Brandon, N. W. Davies & J. S. Sorensen. (2007) Pharmacokinetics of 1,8-cineole, a dietary toxin, in the brushtail possum (): Significance for feeding. Xenobiotica 37:9, pages 903-922.
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AlisonM. Miller, Clare McArthur, PhilipJ. Smethurst & ShaoF. Wang. (2006) Preferences of two mammalian herbivores for tree seedlings and potential cover crops in plantation forestry. Australian Forestry 69:2, pages 114-121.
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Cosima C. Hoch, Julie Petry, Lena Griesbaum, Tobias Weiser, Kathrin Werner, Michael Ploch, Admar Verschoor, Gabriele Multhoff, Ali Bashiri Dezfouli & Barbara Wollenberg. (2023) 1,8-cineole (eucalyptol): A versatile phytochemical with therapeutic applications across multiple diseases. Biomedicine & Pharmacotherapy 167, pages 115467.
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Yuchen Tan, Qianqian Liu, Zhicheng Wang, Qiangsheng Pu, Shangli Shi & Junhu Su. (2022) Plateau zokors (Eospalax baileyi) respond to secondary metabolites from the roots of Stellera chamaejasme by enhancing hepatic inflammatory factors and metabolic pathway genes. Comparative Biochemistry and Physiology Part C: Toxicology & Pharmacology 258, pages 109368.
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Anna R Staudenmaier, Lisa A Shipley, Meghan J Camp, Jennifer S Forbey, Ann E Hagerman, Abigail E Brandt & Daniel H Thornton. (2022) Mule deer do more with less: comparing their nutritional requirements and tolerances with white-tailed deer. Journal of Mammalogy 103:1, pages 178-195.
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Caroline Marschner, Mark B. Krockenberger, Damien P. Higgins, Christopher Mitchell & Ben D. Moore. (2019) Ingestion and Absorption of Eucalypt Monoterpenes in the Specialist Feeder, the Koala (Phascolarctos cinereus). Journal of Chemical Ecology 45:9, pages 798-807.
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Michael Rychlik. 2017. Springer Handbook of Odor. Springer Handbook of Odor 75 76 .
Hasan Turkez, Elanur Aydın, Fatime Geyikoglu & Damla Cetin. (2014) Genotoxic and oxidative damage potentials in human lymphocytes after exposure to terpinolene in vitro. Cytotechnology 67:3, pages 409-418.
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Miguel A. Bedoya-Pérez, Daniel D. Issa, Peter B. Banks & Clare McArthur. (2014) Quantifying the response of free-ranging mammalian herbivores to the interplay between plant defense and nutrient concentrations. Oecologia 175:4, pages 1167-1177.
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Robert Azerad. (2014) 1,8‐Cineole: Chemical and Biological Oxidation Reactions and Products. ChemPlusChem 79:5, pages 634-655.
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Frauke Kirsch, Kathie Horst, Waldemar Röhrig, Michael Rychlik & Andrea Buettner. (2012) Tracing metabolite profiles in human milk: studies on the odorant 1,8-cineole transferred into breast milk after oral intake. Metabolomics 9:2, pages 483-496.
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Monika Schaffarczyk, Teodor Silviu Balaban, Michael Rychlik & Andrea Buettner. (2013) Syntheses of Chiral 1,8-Cineole Metabolites and Determination of Their Enantiomeric Composition in Human Urine After Ingestion of 1,8-Cineole-Containing Capsules. ChemPlusChem 78:1, pages 77-85.
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Stuart McLean, Noel W. Davies & Natasha L. Wiggins. (2012) Scent Chemicals of the Brushtail Possum, Trichosurus vulpecula. Journal of Chemical Ecology 38:10, pages 1318-1339.
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Lisa A. Shipley, Edward M. Davis, Laura A. Felicetti, Stuart McLean & Jennifer Sorensen Forbey. (2012) Mechanisms for Eliminating Monoterpenes of Sagebrush by Specialist and Generalist Rabbits. Journal of Chemical Ecology 38:9, pages 1178-1189.
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Carolyn L. Nersesian, Peter B. Banks, Stephen J. Simpson & Clare McArthur. (2012) Mixing nutrients mitigates the intake constraints of a plant toxin in a generalist herbivore. Behavioral Ecology 23:4, pages 879-888.
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Michael Murray. 2012. Metabolism of Drugs and Other Xenobiotics. Metabolism of Drugs and Other Xenobiotics 517 542 .
Kathie Horst & Michael Rychlik. (2010) Quantification of 1,8‐cineole and of its metabolites in humans using stable isotope dilution assays. Molecular Nutrition & Food Research 54:10, pages 1515-1529.
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María del H. Loandos, Margarita B. Villecco, Eleuterio Burgueño-Tapia, Pedro Joseph-Nathan & César A. N. Catalán. (2009) Preparation and Absolute Configuration of (1 R ,4 R )-(+)-3-Oxo-, (1 S ,4 S )-(-)-3-Oxo- and (1 R ,3 S ,4 R )-(+)-3-Acetyloxy-5-oxo-1,8-cineole . Natural Product Communications 4:11, pages 1934578X0900401.
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Stuart McLean, Stephen M. Richards, Siow-Leng Cover, Sue Brandon, Noel W. Davies, John P. Bryant & Thomas P. Clausen. (2009) Papyriferic Acid, An Antifeedant Triterpene From Birch Trees, Inhibits Succinate Dehydrogenase From Liver Mitochondria. Journal of Chemical Ecology 35:10, pages 1252-1261.
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Margarita B. Villecco, Julieta V. Catalán, Marta I. Vega, Francisco M. Garibotto, Ricardo D. Enriz & César A. N. Catalán. (2008) Synthesis and Antibacterial Activity of Highly Oxygenated 1,8-Cineole Derivatives. Natural Product Communications 3:3, pages 1934578X0800300.
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Shannon L. Haley, John G. Lamb, Michael R. Franklin, Jonathan E. Constance & M. Denise Dearing. (2007) Xenobiotic metabolism of plant secondary compounds in juniper (Juniperus monosperma) by specialist and generalist woodrat herbivores, genus Neotoma. Comparative Biochemistry and Physiology Part C: Toxicology & Pharmacology 146:4, pages 552-560.
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Jennifer S. Sorensen, Kristian C. Forbey, Robert L. Tanquay & Bernie McLeod. (2007) Tissue distribution of cytochrome P450 3A (CYP3A) in brushtail possums (Trichosurus vulpecula) exposed to Eucalyptus terpenes. Comparative Biochemistry and Physiology Part C: Toxicology & Pharmacology 145:2, pages 194-201.
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Karen J. Marsh, Ian R. Wallis, Stuart McLean, Jennifer S. Sorensen & William J. Foley. (2006) CONFLICTING DEMANDS ON DETOXIFICATION PATHWAYS INFLUENCE HOW COMMON BRUSHTAIL POSSUMS CHOOSE THEIR DIETS. Ecology 87:8, pages 2103-2112.
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Jennifer S. Sorensen & M. Denise Dearing. (2006) Efflux Transporters as a Novel Herbivore Countermechanism to Plant Chemical Defenses. Journal of Chemical Ecology 32:6, pages 1181-1196.
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M. Denise DearingWilliam J. FoleyStuart McLean. (2005) The Influence of Plant Secondary Metabolites on the Nutritional Ecology of Herbivorous Terrestrial Vertebrates. Annual Review of Ecology, Evolution, and Systematics 36:1, pages 169-189.
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Rebecca R. Boyle, Stuart McLean, Sue Brandon & Natasha Wiggins. (2005) 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 31:12, pages 2775-2790.
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Mike Duisken, Frank Sandner, Brunhilde Blömeke & Juliane Hollender. (2005) Metabolism of 1,8-cineole by human cytochrome P450 enzymes: identification of a new hydroxylated metabolite. Biochimica et Biophysica Acta (BBA) - General Subjects 1722:3, pages 304-311.
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Raymond M. Carman, Ward T. Robinson & Craig J. Wallis. (2005) The 3-Hydroxycineoles. Australian Journal of Chemistry 58:11, pages 785.
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Dugald C. Close, Clare McArthur, Ann E. Hagerman & Hugh Fitzgerald. (2005) Differential distribution of leaf chemistry in eucalypt seedlings due to variation in whole-plant nutrient availability. Phytochemistry 66:2, pages 215-221.
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John G. Lamb, Purba Marick, Jennifer Sorensen, Shannon Haley & M. Denise Dearing. (2004) Liver biotransforming enzymes in woodrats Neotoma stephensi (Muridae). Comparative Biochemistry and Physiology Part C: Toxicology & Pharmacology 138:2, pages 195-201.
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Ben D. Moore, Ian R. Wallis, Karen J. Marsh & William J. Foley. 2004. Conservation of Australia's Forest Fauna. Conservation of Australia's Forest Fauna 549 575 .
J. S. Sorensen, C. A. Turnbull & M. D. Dearing. (2004) A Specialist Herbivore ( Neotoma stephensi ) Absorbs Fewer Plant Toxins than Does a Generalist ( Neotoma albigula ) . Physiological and Biochemical Zoology 77:1, pages 139-148.
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Dugald Close, Clare McArthur, Stephen Paterson, Hugh Fitzgerald, Andrew Walsh & Tamara Kincade. (2003) PHOTOINHIBITION: A LINK BETWEEN EFFECTS OF THE ENVIRONMENT ON EUCALYPT LEAF CHEMISTRY AND HERBIVORY. Ecology 84:11, pages 2952-2966.
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Rebecca R Boyle, Stuart McLean, Sue Brandon, Georgia J Pass & Noel W Davies. (2002) 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 780:2, pages 397-406.
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Frederick A. Luzzio & Damien Y. Duveau. (2002) Enzymatic resolution of the 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane (1,8-cineole) system. Tetrahedron: Asymmetry 13:11, pages 1173-1180.
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Rebecca Boyle, Stuart McLean, William Foley, Noel W Davies, Evan J Peacock & Ben Moore. (2001) Metabolites of dietary 1,8-cineole in the male koala (Phascolarctos cinereus). Comparative Biochemistry and Physiology Part C: Toxicology & Pharmacology 129:4, pages 385-395.
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