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Crotalaria medicaginea associated with horse deaths in northern Australia: New pyrrolizidine alkaloids

Fletcher, M. T., Hayes, P. Y., Somerville, M. J. and De Voss, J. J. (2011) Crotalaria medicaginea associated with horse deaths in northern Australia: New pyrrolizidine alkaloids. Journal of Agricultural and Food Chemistry, 59 (21). pp. 11888-11892.

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Article Link(s): http://doi.org/10.1021/jf203147x

Publisher URL: http://pubs.acs.org/doi/pdfplus/10.1021/jf203147x

Abstract

Crotalaria medicaginea has been implicated in horse poisoning in grazing regions of central-west Queensland, which resulted in the deaths of more than 35 horses from hepatotoxicosis in 2010. Liver pathology was suggestive of pyrrolizidine alkaloidosis, and we report here the isolation of two previously uncharacterized pyrrolizidine alkaloids from C. medicaginea plant specimens collected from pastures where the horses died. The first alkaloid was shown by mass spectometric and NMR analyses to be 1β,2β-epoxy-7β-hydroxy- 1α-methoxymethyl-8α-pyrrolizidine, which, like other alkaloids previously isolated from C. medicaginea, lacks the requisite functionality for hepatotoxcity. The second alkaloid isolated in this investigation was a new macrocyclic diester of otonecine, which we have named cromedine. The 1H and 13C NMR spectra of cromedine were fully assigned by 2D NMR techniques and allowed the constitution of the macrocyclic diester to be assigned unambiguously. C. medicaginea specimens implicated in this investigation do not belong to any of the three recognized Australian varieties (C. medicaginea var. neglecta, C. medicaginea var. medicaginea, and C. medicaginea var. linearis) and appear to be a local variant or form, referred to here as C. medicaginea (chemotype cromedine). © 2011 American Chemical Society.

Item Type:Article
Keywords:cromedine Crotalaria medicaginea hepatotoxic horse otonecine pumiline A pyrrolizidine alkaloids Pyrrolizidine alkaloid Agriculture Metabolites Nuclear magnetic resonance spectroscopy Value engineering Nitrogen compounds animal animal food article Australia chemistry classification Crotalaria horse disease metabolism mortality pathology Animal Feed Animals Horse Diseases Horses Queensland Equidae
Subjects:Plant pests and diseases > Poisonous plants
Animal culture > Horses
Veterinary medicine > Other diseases and conditions
Deposited On:26 Mar 2019 01:54
Last Modified:26 Mar 2019 01:54

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