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Jensenone: Biological reactivity of a marsupial antifeedant from Eucalyptus

Citation

McLean, SR and Brandon, S and Davies, NW and Foley, WJ and Muller, HK, Jensenone: Biological reactivity of a marsupial antifeedant from Eucalyptus, Journal of Chemical Ecology, 30, (1) pp. 19-36. ISSN 0098-0331 (2004) [Refereed Article]


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The final publication is available at http://www.springerlink.com

Official URL: http://www.springerlink.com/content/k9805284007hh7...

DOI: doi:10.1023/B:JOEC.0000013180.46747.07

Abstract

The resistance of Eucalyptus to browsing mammals has been related to the level and type of formylated phloroglucinol compounds (FPCs) present in the leaf. The antifeedant activity of FPCs appears to depend on their aldehyde groups, but little else is known of their mode of action. We have sought to elucidate this further by examining the biological reactivity and disposition of jensenone, a model FPC. Neither jensenone nor any metabolites were detected in urine or feces of marsupial brushtail or ringtail possums that had ingested up to 725 mg·kg -0.75. When jensenone was incubated in rat gastrointestinal segments in vitro, it rapidly disappeared. Jensenone also reacted rapidly with glutathione, cysteine, glycine, ethanolamine, and trypsin, and more slowly with acetylcysteine and albumin. Sideroxylonal, a more complex FPC, exhibited the same reactivity. Torquatone, a related compound that lacks both aldehyde groups and antifeedant activity, was unreactive. Mass spectroscopic analysis indicated that the adducts were Schiff bases formed between the aldehyde groups of FPCs and amine groups of the conjugating molecules. Successive adducts were formed with the two aldehyde groups of jensenone, and the four groups of sideroxylonal. The jensenone bis-glutathione adduct appeared to cyclize to the disulfide form. These findings suggest that the antifeedant effects of FPCs are due to their facile binding to amine groups on critical molecules in the gastrointestinal tract, leading to a loss of metabolic function. The consequent toxic reaction, probably involving chemical mediators such as 5-hydroxytryptamine (5HT), may cause colic, nausea, and a general malaise, resulting in anorexia.

Item Details

Item Type:Refereed Article
Research Division:Medical and Health Sciences
Research Group:Pharmacology and Pharmaceutical Sciences
Research Field:Basic Pharmacology
Objective Division:Environment
Objective Group:Flora, Fauna and Biodiversity
Objective Field:Forest and Woodlands Flora, Fauna and Biodiversity
Author:McLean, SR (Professor Stuart McLean)
Author:Brandon, S (Mrs Susan Brandon)
Author:Davies, NW (Associate Professor Noel Davies)
Author:Muller, HK (Professor Konrad Muller)
ID Code:30007
Year Published:2004
Web of Science® Times Cited:19
Deposited By:Pharmacy
Deposited On:2004-08-01
Last Modified:2011-05-23
Downloads:2 View Download Statistics

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