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Simultaneous enantioselective determination of triadimefon and its metabolite triadimenol in edible vegetable oil by gel permeation chromatography and ultraperformance convergence chromatography/tandem mass spectrometry

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Abstract

A novel, sensitive, and efficient enantioselective method for the determination of triadimefon and its metabolite triadimenol in edible vegetable oil, was developed by gel permeation chromatography and ultraperformance convergence chromatography/tandem triple quadrupole mass spectrometry. After the vegetable oil samples were prepared using gel permeation chromatography, the eluent was collected, evaporated, and dried with nitrogen gas. The residue was redissolved by adding methanol up to a final volume of 1 mL. The analytes of six enantiomers were analyzed on Chiralpak IA-3 column (150 × 4.6 mm) using compressed liquid CO2-mixed 14 % co-solvents, comprising methanol/acetonitrile/isopropanol = 20/20/60 (v/v/v) in the mobile phase at 30 °C, and the total separation time was less than 4 min at a flow rate of 2 mL/min. Quantification was achieved using matrix-matched standard calibration curves. The overall mean recoveries for six enantiomers from vegetable oil were 90.1–97.3 %, with relative standard deviations of 0.8–5.4 % intra-day and 2.3–5.0 % inter-day at 0.5, 5, and 50 μg/kg levels. The limits of quantification were 0.5 μg/kg for all enantiomers based on five replicate extractions at the lowest fortified level in vegetable oil. Moreover, the absolute configuration of six enantiomers had been determined based on comparisons of the vibrational circular dichroism experimental spectra with the theoretical curve obtained by density functional theory calculations. Application of the proposed method to the 40 authentic vegetable oil samples from local markets suggests its potential use in enantioselective determination of triadimefon and triadimenol enantiomers.

Chemical structures and UPC2-MS/MS separation chromatograms of triadimefon and triadimenol

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Abbreviations

AC:

Absolute configuration

CSP:

Chiral stationary phase

DFT:

Density functional theory

GPC:

Gel permeation chromatography

MRL:

Maximum residue limit

RSD:

Relative standard deviation

SFC:

Supercritical fluid chromatography

SSE:

Slope matrix-matched calibration/slope standard calibration in solvent

VCD:

Vibrational circular dichroism

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (no. 21207118), the Project of Science and Technology Plan of Zhejiang Province, China (no. 2014C37103), and the Natural Science Foundation of Zhejiang Province, China (no. Y15B070017).

Conflict of interest

The authors declare that they have no competing interests.

Author information

Authors and Affiliations

  1. Institute of Quality and Standard for Agricultural Products, Zhejiang Academy of Agricultural Sciences, Hangzhou, 310021, China

    Zhoulin Yao, Mingfei Xu, Qiang Wang & Hu Zhang

  2. State Key Laboratory Breeding Base for Zhejiang Sustainable Pest and Disease Control, Zhejiang Academy of Agricultural Sciences, Hangzhou, 310021, China

    Zhoulin Yao, Mingfei Xu, Qiang Wang & Hu Zhang

  3. MOA Key Laboratory for Pesticide Residue Detection, Hangzhou, 310021, China

    Zhoulin Yao, Mingfei Xu, Qiang Wang & Hu Zhang

  4. Zhejiang Citrus Research Institute, Zhejiang Academy of Agricultural Sciences, Taizhou, 318020, China

    Zhoulin Yao & Mei Lin

  5. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, China

    Zhoulin Yao & Yelong Miao

  6. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

    Xiaoge Li

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  1. Zhoulin Yao
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  2. Xiaoge Li
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  7. Hu Zhang
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Correspondence to Hu Zhang.

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Yao, Z., Li, X., Miao, Y. et al. Simultaneous enantioselective determination of triadimefon and its metabolite triadimenol in edible vegetable oil by gel permeation chromatography and ultraperformance convergence chromatography/tandem mass spectrometry. Anal Bioanal Chem 407, 8849–8859 (2015). https://doi.org/10.1007/s00216-015-9046-y

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