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Identification of Acid Hydrolysis Metabolites of the Pimelea Toxin Simplexin for Targeted UPLC-MS/MS Analysis

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Loh, Z. H., Hungerford, N. L., Ouwerkerk, D., Klieve, A. V. and Fletcher, M. T. (2023) Identification of Acid Hydrolysis Metabolites of the Pimelea Toxin Simplexin for Targeted UPLC-MS/MS Analysis. Toxins, 15 (9). p. 551. ISSN 2072-6651

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Article Link: https://doi.org/10.3390/toxins15090551

Publisher URL: https://www.mdpi.com/2072-6651/15/9/551

Abstract

Pimelea poisoning of cattle is a unique Australian toxic condition caused by the daphnane orthoester simplexin present in native Pimelea pasture plants. Rumen microorganisms have been proposed to metabolise simplexin by enzymatic reactions, likely at the orthoester and epoxide moieties of simplexin, but a metabolic pathway has not been confirmed. This study aimed to investigate this metabolic pathway through the analysis of putative simplexin metabolites. Purified simplexin was hydrolysed with aqueous hydrochloric acid and sulfuric acid to produce target metabolites for UPLC-MS/MS analysis of fermentation fluid samples, bacterial isolate samples, and other biological samples. UPLC-MS/MS analysis identified predicted hydrolysed products from both acid hydrolysis procedures with MS breakdown of these putative products sharing high-resolution accurate mass (HRAM) fragmentation ions with simplexin. However, targeted UPLC-MS/MS analysis of the biological samples failed to detect the H2SO4 degradation products, suggesting that the rumen microorganisms were unable to produce similar simplexin degradation products at detectable levels, or that metabolites, once formed, were further metabolised. Overall, in vitro acid hydrolysis was able to hydrolyse simplexin at the orthoester and epoxide functionalities, but targeted UPLC-MS/MS analysis of biological samples did not detect any of the identified simplexin hydrolysis products.

Item Type:Article
Corporate Creators:Department of Agriculture and Fisheries, Queensland
Business groups:Animal Science
Keywords:Pimelea; simplexin; plant toxin; mass spectrometry; metabolite; rumen; fermentation; acid hydrolysis
Subjects:Animal culture > Cattle
Veterinary medicine > Veterinary microbiology
Veterinary medicine > Veterinary toxicology
Live Archive:07 Sep 2023 05:44
Last Modified:07 Sep 2023 05:44

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