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

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


Author Fletcher, Mary T.
Hayes, Patricia Y.
Somerville, Michael J.
De Voss, James J.
Title Crotalaria medicaginea associated with horse deaths in Northern Australia: New pyrrolizidine alkaloids
Journal name Journal of Agricultural and Food Chemistry   Check publisher's open access policy
ISSN 0021-8561
1520-5118
Publication date 2011-11-09
Sub-type Article (original research)
DOI 10.1021/jf203147x
Volume 59
Issue 21
Start page 11888
End page 11892
Total pages 5
Place of publication Washington, DC, U.S.A.
Publisher American Chemical Society
Collection year 2012
Language eng
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 1Hand 13C NMRspectra 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, andC. medicaginea var. linearis) and appear to be a local variant or form, referred to here as C. medicaginea (chemotype cromedine).
Keyword Pyrrolizidine alkaloids
Otonecine
Cromedine
Pumiline A
Horse
Hepatotoxicity
Crotalaria medicaginea
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2012 Collection
Queensland Alliance for Agriculture and Food Innovation
School of Chemistry and Molecular Biosciences
 
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Created: Tue, 18 Oct 2011, 10:39:18 EST by Dr James De Voss on behalf of School of Chemistry & Molecular Biosciences