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Extraction and determination of the Pimelea toxin simplexin in complex plant-polymer biocomposites using ultrahigh-performance liquid chromatography coupled with quadrupole Orbitrap mass spectrometry

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Abstract

In the present paper, we describe how a robust and fundamental methodology was developed for extraction and determination of a principal natural toxin compound, simplexin, from a series of bulk biocomposites. These complex matrices were fabricated by direct encapsulating either ground plant particles or an ethanolic crude extract of the Australian toxic pasture plant Pimelea trichostachya in the biodegradable polymer poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Proton nuclear magnetic resonance spectroscopy was initially employed to examine the chemical compositions of these complicated systems. Then, a more sensitive strategy was developed and validated by combining solid-phase extraction and ultrahigh-performance liquid chromatography hyphenated with a quadrupole Orbitrap mass spectrometer for the quantification of simplexin embedded in different biocomposites. Satisfactory linearity (R2 > 0.99) and recovery ranges (86.8–116%) with precision (relative standard deviations) of between 0.2 and 13% (n = 3) were achieved from seven biocomposites. The established protocol was further shown to be accurate and reliable in confirming the homogeneous distribution of the simplexin in different biocomposite formulations. A limited mass transfer of simplexin (< 3.5%) from one of the biocomposites into a simulated but sterilized in vitro rumen environment after a 10-day incubation was also revealed by utilizing the method. This quantitative analysis of targeted natural product within plant material-integrated polymeric platforms has potential application when controlled release is required in the bovine rumen and other biological systems.

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Acknowledgements

The authors are grateful to Dr. Greg Pierens at the Centre of Advanced Imaging (CAI), the University of Queensland, for offering technical support in 500-MHz NMR experiments.

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The authors confirm that the data supporting the results of this study are available within the article and its supplementary information.

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Funding

This work was part of the Meat & Livestock Australia (MLA) project B.GBP.0023: Improving beef production through management of plant toxins. Plant material used in this study was collected during MLA Donor Company (MDC) project P.PSH.0900: Pimelea toxicity – finding potential solutions for managing cattle poisoning.

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Authors and Affiliations

  1. School of Chemical Engineering, University of Queensland, Brisbane, Queensland, 4072, Australia

    Yue Yuan, Emilie Gauthier & Bronwyn Laycock

  2. Queensland Alliance for Agriculture and Food Innovation (QAAFI), University of Queensland, Brisbane, Queensland, 4108, Australia

    Natasha L. Hungerford, Diane Ouwerkerk & Mary T. Fletcher

  3. Agri-Science Queensland, Queensland Department of Agriculture and Fisheries (DAF), Brisbane, Queensland, 4102, Australia

    Diane Ouwerkerk

  4. Biosecurity Queensland, Queensland Department of Agriculture and Fisheries (DAF), Brisbane, Queensland, 4108, Australia

    Ken W. L. Yong

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  1. Yue Yuan
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Contributions

Mary T. Fletcher acquired the funding, and conceptualized the project with Bronwyn Laycock. Emilie Gauthier and Yue Yuan manufactured the biocomposites. Yue Yuan prepared all the samples and standards in the presented work. The UHPLC-Q-Orbitrap-MS method was established by Natasha L. Hungerford and Ken W. L. Yong, then validated by Yue Yuan. The solid-phase extraction method was initiated by Natasha L. Hungerford and optimized by Yue Yuan. Diane Ouwerkerk contributed to the experiment design of the release test. The 1H NMR, sample extraction, and UHPLC-Q-Orbitrap-MS analysis and data collection were performed by Yue Yuan. The first draft of the manuscript was written by Yue Yuan and all the authors commented on previous versions of the manuscript. All the authors read and approved the final manuscript.

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Correspondence to Mary T. Fletcher or Bronwyn Laycock.

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Yuan, Y., Hungerford, N.L., Gauthier, E. et al. Extraction and determination of the Pimelea toxin simplexin in complex plant-polymer biocomposites using ultrahigh-performance liquid chromatography coupled with quadrupole Orbitrap mass spectrometry. Anal Bioanal Chem 413, 5121–5133 (2021). https://doi.org/10.1007/s00216-021-03475-5

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