Determination of Hepatotoxic Indospicine in Australian Camel Meat by Ultra-Performance Liquid Chromatography–Tandem Mass Spectrometry

Tan, Eddie Ti Tjih; Fletcher, Mary T.; Yong, Ken W. L.; D'Arcy, B. R.; Jassim, Rafat Al

doi:10.1021/jf4052495

Cited by 12 publications

(42 citation statements)

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“…The reaction mixture was gradually warmed up to room temperature and stirred for 2 h. Upon completion, saturated aqueous NH 4 Cl solution (15 mL) was added and the aqueous layer was extracted with CH 2 Cl 2 (10 mL × 3). 1 L-2,6-Diamino-6-iminohexanoic acid (9). Purification by flash column chromatography on silica gel ( petroleum ether/ ethyl acetate, 2 : 1 to 1 : 1) gave the desired product as a colourless oil (2.82 g, 95%).…”

Section: General Methodsmentioning

confidence: 99%

“…9 In the reported analysis of residues in camel meat tissues indospicine (1) Finally, in order to test the utility of this synthetic methodology, an indospicine analogue, L-norindospicine (9) was also synthesised from commercially available N-cbz-L-serine ethyl ester (10) (Scheme 3). In order to explore the utility of this route and to produce labelled material for quantitation studies, 9 a multiply deuterated indospicine, [ 2 H 3 ]-1 (Scheme 2) was synthesised employing the same This deuterated indospicine has been demonstrated to be useful as an internal standard in LC-MS/MS stable isotope dilution analysis (SIDA) of indospicine in complex tissue matrixes to compensate for matrix effects and increase accuracy of analysis.…”

Section: Scheme 1 the Synthesis Of L-indospicine (1)mentioning

confidence: 99%

“…Various experimental studies have demonstrated the toxicity of Indigofera species containing indospicine to cattle, sheep, goats, rabbits, mice and rats, with common signs being decreased feed intake, weight loss and liver damage. 8,9 Indospicine was first isolated by Hegarty and co-workers from Indigofera spicata and was later identified as a toxic amino acid responsible for the observed hepatoxicity. is responsible for the hepatotoxic effects of these plants.…”

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Synthesis of l-indospicine, [5,5,6-²H₃]-l-indospicine and l-norindospicine

et al. 2016

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Indospicine is a non-proteogenic amino acid that accumulates as the free amino acid in livestock grazing Indigofera plant species and causes both reproductive losses and hepatotoxic effects. An efficient synthetic route to l-indospicine from l-homoserine lactone is described. The methodology is applicable for the synthesis of both deuterium labelled isotopomers and structural analogues for utilisation in biological studies. The key steps are a zinc mediated Barbier reaction with acrylonitrile and a Pinner reaction that together introduce the target amidine moiety.

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Section: General Methodsmentioning

confidence: 99%

Section: Scheme 1 the Synthesis Of L-indospicine (1)mentioning

confidence: 99%

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Synthesis of l-indospicine, [5,5,6-²H₃]-l-indospicine and l-norindospicine

et al. 2016

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“…lndospicine analysis of both muscle and liver samples was performed according to the published liquid chromatography-tandem mass spectrometry procedure (Tan et al, 2014) with minor modification. Finely chopped muscle and liver samples (0.…”

Section: Indospicine Extraction and Analysismentioning

confidence: 99%

Assessing the risk of residues of the toxin indospicine in bovine muscle and liver from north-west Australia

Netzel

Palmer

Masters

et al. 2019

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Indospicine is a natural toxin occurring only in Indigofera plant species, including the Australian native species I. linnaei. These perennial legumes are resistant to drought and palatable to grazing livestock including cattle. Indospicine accumulates in the tissues (including muscle) of animals grazing Indigofera and these residues persist for several months after exposure. Dogs are particularly sensitive to indospicine with reports in past decades of hepatotoxicosis and mortalities in dogs after dietary exposure to indospicinecontaminated horse and camel meat. The risk for human consumption is not known, and the current study was undertaken to assess indospicine levels in cattle going to slaughter from divergent regions of Western Australia, and to predict the likelihood of significant residues being present. Muscle and corresponding liver samples from 776 cattle originating from the Kimberley and Pilbara Regions in the tropical north of the state, where I. linnaei is prevalent, and 640 cattle from the South West and South Coast Regions in the temperate south west of the state, where the plant is not known to occur, were collected at abattoirs over four seasons in 2015-2017. Indospicine levels were measured by LC-MS/MS and ranged from below detection to 3.63 mg/kg. No indospicine residues were detected in any of the animals originating from the South West and South Coast Regions. Prevalence of indospicine residues in cattle from the Kimberley Region was as high as 33% in spring and 90% in autumn, with positive animals being present in most consignments and on most properties. The average prevalence of indospicine residues from the Kimberley and Pilbara Regions throughout the survey period was 62%. @Risk best fit probability distributions showed ninety-fifth percentile (P95) indospicine concentrations of 0.54 mg/kg for muscle and 0.77 mg/kg for liver in cattle originating from the Kimberley and Pilbara Regions during the survey period. When considered with average Australian meat consumption data, the 15 or more animals. Consignments were designated as 'spring' for slaughter dates within the period 1 August to 30 November and 'autumn' for 1 March to 31 July. No consignments were sampled December to February as this period represents the rainy season in the Kimberley and Pilbara Regions, and for logistical reasons animals are not sent to abattoir during this period.

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“…Van gossypol (katoenplant) is bekend dat het in lage hoeveelheden overgedragen kan worden naar plasma en melk (Wang et al, 2012). Overdracht van indospicine (Indigofera plant)(aminozuur, arginine analoog) naar vlees is gemeld in Australië (FitzGerald et al, 2011;Tan et al, 2014). Het is onbekend of deze planttoxine ook in Nederlandse weideplanten voorkomt of dat geïmporteerd vlees deze planttoxine bevat.…”

Section: Overdracht Naar Dierlijke Productenunclassified