Characterisation and bioactivity of secondary metabolites of Amaranthus retroflexus L. implicated in livestock poisoning

Paul Weston, Saliya Gurusinghe, Emily Birckhead, Dominik Skoneczny, Leslie Weston, Jane Quinn

Research output: Other contribution to conferencePoster

Abstract

Amaranthus retroflexus, originating from South America is an introduced weed in many parts of the world, including Australia. Ingestion of the plant material has been associated with acute renal failure in a number of livestock species including cattle, sheep and horse. While previous reports indicated that its foliage contains high levels of nitrogen, the characterization of the chemical composition of A. retroflexus foliage has not been performed fully, with differentiation of constituents in plant parts such as the leaf, stem, inflorescence and root. We report here the composition of the secondary metabolites of A. retroflexus foliage and the results of bioassay-guided cytotoxicity assessment of A. retroflexus extracts in an attempt to isolate and identify the associated toxins. As determined by UPLC-MS QTOF, all tissues (leaves, flowers, stems and roots) of A. retroflexus possessed an abundance of nitrogen-containing compounds, the primary constituents of which had apparent molecular formulae of C8H18NO2 and C9H20NO2, potentially the methyl and ethyl esters, respectively, of 4-oxo-1-butanaminium, a structural relative of choline. Cytotoxicity, as measured by MTT assay against the murine fibroblast cell line NIH3T3, was associated with a single compound in the extracts of A. retroflexus leaves, which we have tentatively identified as a compound with a high degree of similarity to the modified peptide N-acetyl-L-α-aspartyl-L-alanyl-L-α-aspartyl-L-α-glutamyl-O-(carboxymethyl)-L-tyrosyl-L-leucinamide, a mammalian metabolite known to play a role in cell signalling. Confirmation of the bioactivity of the putative toxin by comparisons with an authentic standard is required to ascertain nephrotoxic activity associated with livestock poisoning.
Original languageEnglish
Pages53
Number of pages1
Publication statusPublished - 2018
Event10th International Symposium on Poisonous Plants : ISOPP 10 - Red Lion Conference Center, St George , United States
Duration: 16 Sep 201820 Sep 2018
https://conference.usu.edu/ISOPP/

Conference

Conference10th International Symposium on Poisonous Plants
CountryUnited States
CitySt George
Period16/09/1820/09/18
Internet address

Fingerprint

Amaranthus retroflexus
secondary metabolites
poisoning
livestock
leaves
cytotoxicity
toxins
stems
extracts
renal failure
nitrogen
choline
plant anatomy
fibroblasts
inflorescences
bioassays
weeds
esters
chemical composition
cell lines

Cite this

Weston, P., Gurusinghe, S., Birckhead, E., Skoneczny, D., Weston, L., & Quinn, J. (2018). Characterisation and bioactivity of secondary metabolites of Amaranthus retroflexus L. implicated in livestock poisoning. 53. Poster session presented at 10th International Symposium on Poisonous Plants , St George , United States.
Weston, Paul ; Gurusinghe, Saliya ; Birckhead, Emily ; Skoneczny, Dominik ; Weston, Leslie ; Quinn, Jane. / Characterisation and bioactivity of secondary metabolites of Amaranthus retroflexus L. implicated in livestock poisoning. Poster session presented at 10th International Symposium on Poisonous Plants , St George , United States.1 p.
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abstract = "Amaranthus retroflexus, originating from South America is an introduced weed in many parts of the world, including Australia. Ingestion of the plant material has been associated with acute renal failure in a number of livestock species including cattle, sheep and horse. While previous reports indicated that its foliage contains high levels of nitrogen, the characterization of the chemical composition of A. retroflexus foliage has not been performed fully, with differentiation of constituents in plant parts such as the leaf, stem, inflorescence and root. We report here the composition of the secondary metabolites of A. retroflexus foliage and the results of bioassay-guided cytotoxicity assessment of A. retroflexus extracts in an attempt to isolate and identify the associated toxins. As determined by UPLC-MS QTOF, all tissues (leaves, flowers, stems and roots) of A. retroflexus possessed an abundance of nitrogen-containing compounds, the primary constituents of which had apparent molecular formulae of C8H18NO2 and C9H20NO2, potentially the methyl and ethyl esters, respectively, of 4-oxo-1-butanaminium, a structural relative of choline. Cytotoxicity, as measured by MTT assay against the murine fibroblast cell line NIH3T3, was associated with a single compound in the extracts of A. retroflexus leaves, which we have tentatively identified as a compound with a high degree of similarity to the modified peptide N-acetyl-L-α-aspartyl-L-alanyl-L-α-aspartyl-L-α-glutamyl-O-(carboxymethyl)-L-tyrosyl-L-leucinamide, a mammalian metabolite known to play a role in cell signalling. Confirmation of the bioactivity of the putative toxin by comparisons with an authentic standard is required to ascertain nephrotoxic activity associated with livestock poisoning.",
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year = "2018",
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Weston, P, Gurusinghe, S, Birckhead, E, Skoneczny, D, Weston, L & Quinn, J 2018, 'Characterisation and bioactivity of secondary metabolites of Amaranthus retroflexus L. implicated in livestock poisoning' 10th International Symposium on Poisonous Plants , St George , United States, 16/09/18 - 20/09/18, pp. 53.

Characterisation and bioactivity of secondary metabolites of Amaranthus retroflexus L. implicated in livestock poisoning. / Weston, Paul; Gurusinghe, Saliya; Birckhead, Emily; Skoneczny, Dominik; Weston, Leslie; Quinn, Jane.

2018. 53 Poster session presented at 10th International Symposium on Poisonous Plants , St George , United States.

Research output: Other contribution to conferencePoster

TY - CONF

T1 - Characterisation and bioactivity of secondary metabolites of Amaranthus retroflexus L. implicated in livestock poisoning

AU - Weston, Paul

AU - Gurusinghe, Saliya

AU - Birckhead, Emily

AU - Skoneczny, Dominik

AU - Weston, Leslie

AU - Quinn, Jane

PY - 2018

Y1 - 2018

N2 - Amaranthus retroflexus, originating from South America is an introduced weed in many parts of the world, including Australia. Ingestion of the plant material has been associated with acute renal failure in a number of livestock species including cattle, sheep and horse. While previous reports indicated that its foliage contains high levels of nitrogen, the characterization of the chemical composition of A. retroflexus foliage has not been performed fully, with differentiation of constituents in plant parts such as the leaf, stem, inflorescence and root. We report here the composition of the secondary metabolites of A. retroflexus foliage and the results of bioassay-guided cytotoxicity assessment of A. retroflexus extracts in an attempt to isolate and identify the associated toxins. As determined by UPLC-MS QTOF, all tissues (leaves, flowers, stems and roots) of A. retroflexus possessed an abundance of nitrogen-containing compounds, the primary constituents of which had apparent molecular formulae of C8H18NO2 and C9H20NO2, potentially the methyl and ethyl esters, respectively, of 4-oxo-1-butanaminium, a structural relative of choline. Cytotoxicity, as measured by MTT assay against the murine fibroblast cell line NIH3T3, was associated with a single compound in the extracts of A. retroflexus leaves, which we have tentatively identified as a compound with a high degree of similarity to the modified peptide N-acetyl-L-α-aspartyl-L-alanyl-L-α-aspartyl-L-α-glutamyl-O-(carboxymethyl)-L-tyrosyl-L-leucinamide, a mammalian metabolite known to play a role in cell signalling. Confirmation of the bioactivity of the putative toxin by comparisons with an authentic standard is required to ascertain nephrotoxic activity associated with livestock poisoning.

AB - Amaranthus retroflexus, originating from South America is an introduced weed in many parts of the world, including Australia. Ingestion of the plant material has been associated with acute renal failure in a number of livestock species including cattle, sheep and horse. While previous reports indicated that its foliage contains high levels of nitrogen, the characterization of the chemical composition of A. retroflexus foliage has not been performed fully, with differentiation of constituents in plant parts such as the leaf, stem, inflorescence and root. We report here the composition of the secondary metabolites of A. retroflexus foliage and the results of bioassay-guided cytotoxicity assessment of A. retroflexus extracts in an attempt to isolate and identify the associated toxins. As determined by UPLC-MS QTOF, all tissues (leaves, flowers, stems and roots) of A. retroflexus possessed an abundance of nitrogen-containing compounds, the primary constituents of which had apparent molecular formulae of C8H18NO2 and C9H20NO2, potentially the methyl and ethyl esters, respectively, of 4-oxo-1-butanaminium, a structural relative of choline. Cytotoxicity, as measured by MTT assay against the murine fibroblast cell line NIH3T3, was associated with a single compound in the extracts of A. retroflexus leaves, which we have tentatively identified as a compound with a high degree of similarity to the modified peptide N-acetyl-L-α-aspartyl-L-alanyl-L-α-aspartyl-L-α-glutamyl-O-(carboxymethyl)-L-tyrosyl-L-leucinamide, a mammalian metabolite known to play a role in cell signalling. Confirmation of the bioactivity of the putative toxin by comparisons with an authentic standard is required to ascertain nephrotoxic activity associated with livestock poisoning.

KW - Amaranthus spp,

KW - nephrotoxin

KW - renal failture

KW - sheep

KW - LC-QTOF-MS

KW - metabolomics

M3 - Poster

SP - 53

ER -

Weston P, Gurusinghe S, Birckhead E, Skoneczny D, Weston L, Quinn J. Characterisation and bioactivity of secondary metabolites of Amaranthus retroflexus L. implicated in livestock poisoning. 2018. Poster session presented at 10th International Symposium on Poisonous Plants , St George , United States.