Fast Phenotyping of LFS-Silenced (Tearless) Onions by Desorption Electrospray Ionization Mass Spectrometry (DESI-MS)
Abstract
Fast MS techniques have been applied to the analysis of sulfur volatiles in Allium species and varieties to distinguish phenotypes. Headspace sampling by proton transfer reaction (PTR) MS and surface sampling by desorption electrospray ionization (DESI) MS were used to distinguish lachrymatory factor synthase (LFS)-silenced (tearless; LFS−) onions from normal, LFS-active (tear-inducing; LFS+), onions. PTR-MS showed lower concentrations of the lachrymatory factor (LF, 3) and dipropyl disulfide 12 from tearless onions. DESI-MS of the tearless onions confirmed the decreased LF 3 and revealed much higher concentrations of the sulfenic acid condensates. Using DESI-MS with MS2 could distinguish zwiebelane ions from thiosulfinate ions. DESI-MS gave reliable fast phenotyping of LFS+ versus LFS– onions by simply scratching leaves and recording the extractable ions for <0.5 min. DESI-MS leaf compound profiles also allowed the rapid distinction of a variety of Allium cultivars to aid plant breeding selections.
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- Bingnan Du, Bo Jin, and Peipei Sun . Syntheses of Sulfides and Selenides through Direct Oxidative Functionalization of C(sp3)–H Bond. Organic Letters 2014, 16 (11) , 3032-3035. https://doi.org/10.1021/ol5011449
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- Zongjun Qiao, Xuefeng Jiang. Recent developments in sulfur–carbon bond formation reaction involving thiosulfates. Organic & Biomolecular Chemistry 2017, 15 (9) , 1942-1946. https://doi.org/10.1039/C6OB02833K
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- Shengrong Guo, Weimin He, Jiannan Xiang, Yanqin Yuan. Palladium-catalyzed direct thiolation of ethers with sodium sulfinates. Tetrahedron Letters 2014, 55 (47) , 6407-6410. https://doi.org/10.1016/j.tetlet.2014.09.098
- Bart M. Nicolaï, Thijs Defraeye, Bart De Ketelaere, Els Herremans, Maarten L.A.T.M. Hertog, Wouter Saeys, Alessandro Torricelli, Thomas Vandendriessche, Pieter Verboven. Nondestructive Measurement of Fruit and Vegetable Quality. Annual Review of Food Science and Technology 2014, 5 (1) , 285-312. https://doi.org/10.1146/annurev-food-030713-092410
- Clara Ibáñez, Virginia García-Cañas, Alberto Valdés, Carolina Simó. Direct Mass Spectrometry-Based Approaches in Metabolomics. 2014, 235-253. https://doi.org/10.1016/B978-0-444-62651-6.00010-6
- Clara Ibáñez, Virginia García-Cañas, Alberto Valdés, Carolina Simó. Novel MS-based approaches and applications in food metabolomics. TrAC Trends in Analytical Chemistry 2013, 52 , 100-111. https://doi.org/10.1016/j.trac.2013.06.015