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  (ERA 2012 Listed)    (ERA 2010 Rank A)   Check publisher's open access policy
Publication date 2011-11-09
Sub-type Article
DOI 10.1021/jf203147x
Volume number 59
Issue number 21
ISSN 0021-8561; 1520-5118
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

 
Versions
Version Filter Type
Citation counts: TR Web of Science Citation Count  Cited 1 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 1 times in Scopus Article | Citations
Google Scholar Search Google Scholar
Access Statistics: 58 Abstract Views  -  Detailed Statistics
Created: Tue, 18 Oct 2011, 10:39:18 EST by Dr James De Voss on behalf of School of Chemistry & Molecular Biosciences