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Journal of agricultural and food chemistry2011; 59(21); 11888-11892; doi: 10.1021/jf203147x

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

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 (1)H and (13)C 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).
Publication Date: 2011-10-06 PubMed ID: 21899365DOI: 10.1021/jf203147xGoogle Scholar: Lookup
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  • Journal Article

Summary

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The study investigates horse deaths in northern Australia linked to consumption of a plant known as Crotalaria medicaginea containing previously uncharacterized pyrrolizidine alkaloids.

Summary of Research

  • The research explores the connection between horse poisoning in the central-west Queensland grazing regions and the Crotalaria medicaginea plant, which led to the death of over 35 horses due to hepatotoxicosis in 2010.
  • Horse liver pathology suggested the cause of death to be pyrrolizidine alkaloidosis – a type of poisoning caused by the consumption of certain types of plants containing pyrrolizidine alkaloids.
  • The researchers isolated two previously unidentified pyrrolizidine alkaloids from C. medicaginea plants gathered from the pastures where the affected horses died.

Findings

  • The first alkaloid identified in the plant was 1β,2β-epoxy-7β-hydroxy-1α-methoxymethyl-8α-pyrrolizidine, found through mass spectrometric and NMR analyses. This alkaloid, though similar to other alkaloids earlier isolated from C. medicaginea, was not identified as a cause for hepatotoxicity in horses.
  • The second alkaloid was a new macrocyclic diester of otonecine, which the researchers named cromedine. The constitution of this macrocyclic diester was unambiguously assigned using 2D NMR techniques.
  • The C. medicaginea specimens related to this investigation were not part of the three recognized Australian varieties (C. medicaginea var. neglecta, C. medicaginea var. medicaginea, and C. medicaginea var. linearis), but appeared to be a local variant. The researchers referred to this variant as C. medicaginea (chemotype cromedine).

Implications of Research

  • This research has crucial implications for the horse farming community in regions where the C. medicaginea (chemotype cromedine) variety is found.
  • The identification of cromedine, a potentially deadly alkaloid in the local variant of C. medicaginea, can inform preventative measures to safeguard horses from further harm.
  • Further research is required to assess the impact of both identified alkaloids, as well as potential compound interactions on the hepatotoxicity in horses.

Cite This Article

APA
Fletcher MT, Hayes PY, Somerville MJ, De Voss JJ. (2011). Crotalaria medicaginea associated with horse deaths in northern Australia: new pyrrolizidine alkaloids. J Agric Food Chem, 59(21), 11888-11892. https://doi.org/10.1021/jf203147x

Publication

ISSN: 1520-5118
NlmUniqueID: 0374755
Country: United States
Language: English
Volume: 59
Issue: 21
Pages: 11888-11892

Researcher Affiliations

Fletcher, Mary T
  • The University of Queensland, Centre for Animal Science, Queensland Alliance for Agriculture and Food Innovation, Health and Food Sciences Precinct, Coopers Plains, Brisbane, Australia. mary.fletcher@uq.edu.au
Hayes, Patricia Y
    Somerville, Michael J
      De Voss, James J

        MeSH Terms

        • Animal Feed / adverse effects
        • Animal Feed / analysis
        • Animals
        • Crotalaria / chemistry
        • Crotalaria / classification
        • Horse Diseases / etiology
        • Horse Diseases / metabolism
        • Horse Diseases / mortality
        • Horse Diseases / pathology
        • Horses
        • Pyrrolizidine Alkaloids / chemistry
        • Pyrrolizidine Alkaloids / metabolism
        • Pyrrolizidine Alkaloids / poisoning
        • Queensland

        Citations

        This article has been cited 1 times.
        1. Hungerford NL, Carter SJ, Anuj SR, Tan BLL, Hnatko D, Martin CL, Sharma E, Yin M, Nguyen TTP, Melksham KJ, Fletcher MT. Analysis of Pyrrolizidine Alkaloids in Queensland Honey: Using Low Temperature Chromatography to Resolve Stereoisomers and Identify Botanical Sources by UHPLC-MS/MS. Toxins (Basel) 2019 Dec 11;11(12).
          doi: 10.3390/toxins11120726pubmed: 31835836google scholar: lookup