Abstract
In order to compare the metabolism of 1,8-cineole in the pyrgo beetle, Paropsisterna tigrina, three other herbivorous insect species, Faex nigroconspersa, Chrysophtharta bimaculata, and Oxyops vitiosa, were fed 1,8-cineole leaf diets. F. nigroconspersa adults excreted predominantly 9-hydroxy-1,8-cineole (36.2% of the volatile constituents) with some 2α-hydroxy-1,8-cineole (11.4%). In contrast, larvae excreted predominantly 2α-hydroxy-1,8-cineole (27.4%) and smaller proportions of 9-hydroxy-1,8-cineole (5.2%) and 3α-hydroxy-1,8-cineole (4.3%). C. bimaculata adults excreted predominantly 3α-hydroxy-1,8-cineole (16.5%). Oxyops vitiosa adults, on a lower 1,8-cineole diet, excreted predominantly 2α,9-dihydroxy-1,8-cineole (4.2%) and 2α-hydroxy-1,8-cineole (3.5%), with smaller proportions of 3α-hydroxy-1,8-cineole (1.1%) and 9-hydroxy-1,8-cineole (0.5%). This is the first reported occurrence of a dihydroxycineole as an insect metabolite. Gas chromatographic and mass spectral data for hydroxycineoles are recorded and interspecific metabolite variation discussed.
Similar content being viewed by others
References
Boland, D. J., Brophy, J. J., and House, A. P. N. (Eds.) 1991. Eucalyptus Leaf Oils: Use, Chemistry, Distillation and Marketing, ACIAR/CSIRO, Inkata, Melbourne.
Boyle, R., McLean, S., and Davies, N. W. 2000. Biotransformation of 1,8-cineole in the brushtail possum (Trichosurus vulpecula). Xenobiotica 30:915-932.
Brophy, J. J. 1999. Potentially commercial melaleucas, pp. 247-274, in I. A. Southwell and R. F. Lowe (Eds.). Tea Tree, the Genus Melaleuca, Vol 9, in R. Hardman (ed.). Medicinal and Aromatic Plants—Industrial Profiles. Harwood Academic Publishers, Amsterdam.
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.
Carman, R. M. and Klika, K. D. 1992. Partially racemic compounds as brushtail possum urinary metabolites. Aust. J. Chem. 45:651-657.
Carman, R. M. and Rayner, A. C. 1994. 2 α,4-Dihydroxy-1,8-cineole. A new possum urinary metabolite. Aust. J. Chem. 47:2087-2097.
Carman, R. M., MacRae, I. C., and Perkins, M. V. 1986. The oxidation of 1,8-cineole by Pseudomonas flava. Aust. J. Chem. 39:1739-1746.
Carman, R. M., Garner, A. C., and Klika, K. D. 1994. 2,9-Dihydroxy and 2,10-dihydroxy-1,8-cineole. Two new possum urinary metabolites. Aust. J. Chem. 47:1509-1521.
Center, T. D., Van, T. K., Rayachhetry, M., Buckingham, G. R., Dray, F. A., Wineriter, S. A., Purcell, M. F., and Pratt, P. D. 2000. Field colonization of the melaleuca snout beetle (Oxyops vitiosa) in south Florida. Biol. Control 19:112-123.
De Little, D. W. 1983. Life cycle and aspects of the biology of Tasmanian eucalyptus leaf beetle Chrysophtharta bimaculata (Olivier) [Coleoptera: Chrysomelidae]. J. Aust. Entomol. Soc. 22:15-18.
Eberhard, I. H., McNamara, J., Pearse, R. J., and Southwell, I. A. 1975. Ingestion and excretion of Euc. punctata and its essential oil by the koala. Aust. J. Zool. 23:169-179.
Fletcher, M. T., Lowe, L. M., Kitching, W., and Konig, W. A. 2000. Chemistry of Leichhardt's grasshopper, Petasida ephippigera, and its host plants, Pityrodia jamesii, P. ternifolia and P. pungens. J. Chem. Ecol. 26:2275-2290.
Flynn, T. M., and Southwell, I. A. 1979. 1,3-Dimethyl-2-oxabicyclo [2. 2. 2]-octane-3-methanol and 1,3-dimethyl-2-oxabicyclo [2.2.2]-octane-3-carboxylic acid, urinary metabolites of 1,8-cineole. Aust. J. Chem. 32:2093-2095.
Gershenzon, J. and Croteau, R. 1991. Terpenoids, pp. 165-219, in G. A. Rosenthal and M. Berenbaum (Eds.). Herbivores: Their Interactions with Secondary Plant Metabolites. Vol I: The Chemical Participants, 2nd ed., Academic Press, San Diego, California.
Gomez, N. E., Witte, L., and Hartmann, T. 1999. Chemical defense in larval tortoise beetles: Essential oil composition of fecal shields of Eurypedus nigrosignata and foliage of its host plant, Cordia curassavica. J. Chem. Ecol. 25:1007-1027.
Greaves, R. 1966. Insect defoliation of eucalypt regrowth in the Florentine valley, Tasmania. Appita 19:119-126.
Klocke, J. A., Darlington, M. V., and Balandrin, M. F. 1987. 1,8-Cineole (eucalyptol), a mosquito feeding and ovipositional repellent from volatile oil of Hemizonia fitchii (Asteraceae). J. Chem. Ecol. 13:2131-2141.
Liu, W.-G. and Rosazza, J. P. N. 1990. Stereospecific hydroxylation of 1,8-cineole using a microbial biocatalyst. Tetrahedron Lett. 31:2833-2836.
MacRae, I. C., Alberts, V., Carman, R. M., and Shaw, I. M. 1979. Products of 1,8-cineole oxidation by a pseudomonad. Aust. J. Chem. 32:917-922.
Maddox, C. D. 1996. Aspects of the biology of Paropsisterna tigrina. MSc thesis. University of Queensland, Brisbane.
Madyastha, K. M. and Chadha, A. 1986. Metabolism of 1,8-cineole in rat: its effects on liver and lung microsomal cytochrome P-450 systems. Bull. Environ. Contam. Toxicol. 37:759-766.
Miyazawa, M., Kameoka, H., Morinaga, K., Negoro, K., and Mura, N. 1989. Hydroxycineole: four new metabolites of 1,8-cineole in rabbits. J. Agric. Food Chem. 37:222-226.
Miyazawa, M., Nakaoka, H., Hyakamachi, M., and Kameoka, H. 1991. Biotransformation of 1,8-cineole to (+)-2-endo-hydroxy-1,8-cineole by Glomerella cinqulata. Chem. Express 6:667-670.
Miyazawa, M., Shindo, M., and Shimada, T. 2001. Oxidation of 1,8-cineole, the monoterpenoid cyclic ether originated from Eucalyptus polybractea, by cytochrome P450 3A enzymes in rat and human liver microsomes. Drug Metab. Dispos. 29:200-205.
Morrow, P. A. and Fox, L. R. 1980. Effects of variation in Eucalyptus oil yield on insect growth and grazing damage. Oecologia 45:209-219.
Nishimura, H., Noma, Y., and Mizutani, J. 1982. Eucalyptus as biomass. Novel compounds from microbial conversion of 1,8-cineole. Agric. Biol. Chem. 46:2601-2604.
Obeng-Ofori, D., Reichmuth, C. H., Bekele, J., and Hassanali, A. 1997. Biological activity of 1,8-cineole, a major component of essential oil of Ocimum kenyense (Ayobangira) against stored product beetles. J. Appl. Entomol. 121:237-243.
Ohmart, C. P. and Larsson, S. 1989. Evidence for absorption of Eucalyptus essential oils by Paropsis atomaria Olivier (Coleoptera: Chrysomelidae). J. Aust. Entomol. Soc. 28:210-205.
Schmidt, S., Walter, G. H., and Moore, C. J. 2000. Host plant adaptations in myrtaceous-feeding Pergid sawflies: essential oils and the morphology and behaviour of Pergagrapta larvae (Hymenoptera, Symphyta, Pergidae). Biol. J. Linn. Soc. 70:15-26.
Southwell, I. A. 1975. Novel urinary monoterpenoid lactones. Tetrahedron Lett. 16:1885-1988.
Southwell, I. A. 1999a. Introduction, pp. 1-7, in I. A. Southwell and R. F. Lowe (Eds.). Tea Tree, the Genus Melaleuca, Vol 9, in R. Hardman (ed.). Medicinal and Aromatic Plants—Industrial Profiles. Harwood Academic Publishers, Amsterdam.
Southwell, I. A. 1999b. Tea tree constituents, pp. 29-62, in I. A. Southwell and R. F. Lowe (Eds.). Tea Tree, the Genus Melaleuca, Vol 9, in R. Hardman (ed.). Medicinal and Aromatic Plants—Industrial Profiles. Harwood Academic Publishers, Amsterdam.
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.
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). J. Chem. Ecol. 21:439-453.
Tisserand, R. and Balacs, T. 1995. Essential Oil Safety. Churchill Livingston, Edinburgh, p. 52.
Turner, C. E., Center, T. D., Burrows, D. W., and Buckingham, G. R. 1998. Ecology and management of Melaleuca quinquenervia, an invader of wetlands in Florida, USA. Wetl. Ecol. Manage. 5:165-178.
Wheeler, G. S. 2001. Host plant quality factors that influence the growth and development of Oxyops vitiosa, a biological control agent of Melaleuca quinquenervia. Biol. Control 22:256-264.
Wheeler, G. S., Massey, L. M., and Southwell, I. A. 2002. Anti-predator defense of biological control agent Oxyops vitiosa is mediated by plant volatiles sequestered from their host plant Melaleuca quinquenervia. J. Chem. Ecol. 28:297-315.
Williams, D. R., Trudgill, P. W., and Taylor, D. G. 1989. Metabolism of 1,8-cineole by a Rhodococcus species: ring cleavage reactions. J. Gen. Microbiol. 135:1957-1967.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Southwell, I.A., Russell, M.F., Maddox, C.D. et al. Differential Metabolism of 1,8–Cineole in Insects. J Chem Ecol 29, 83–94 (2003). https://doi.org/10.1023/A:1021976513603
Issue Date:
DOI: https://doi.org/10.1023/A:1021976513603