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Wax ester profiling of seed oil by nano-electrospray ionization tandem mass spectrometry

BACKGROUND: Wax esters are highly hydrophobic neutral lipids that are major constituents of the cutin and suberin layer. Moreover they have favorable properties as a commodity for industrial applications. Through transgenic expression of wax ester biosynthetic genes in oilseed crops, it is possible...

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Autores principales: Iven, Tim, Herrfurth, Cornelia, Hornung, Ellen, Heilmann, Mareike, Hofvander, Per, Stymne, Sten, Zhu, Li-Hua, Feussner, Ivo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: BioMed Central 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3766222/
https://www.ncbi.nlm.nih.gov/pubmed/23829499
http://dx.doi.org/10.1186/1746-4811-9-24
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author Iven, Tim
Herrfurth, Cornelia
Hornung, Ellen
Heilmann, Mareike
Hofvander, Per
Stymne, Sten
Zhu, Li-Hua
Feussner, Ivo
author_facet Iven, Tim
Herrfurth, Cornelia
Hornung, Ellen
Heilmann, Mareike
Hofvander, Per
Stymne, Sten
Zhu, Li-Hua
Feussner, Ivo
author_sort Iven, Tim
collection PubMed
description BACKGROUND: Wax esters are highly hydrophobic neutral lipids that are major constituents of the cutin and suberin layer. Moreover they have favorable properties as a commodity for industrial applications. Through transgenic expression of wax ester biosynthetic genes in oilseed crops, it is possible to achieve high level accumulation of defined wax ester compositions within the seed oil to provide a sustainable source for such high value lipids. The fatty alcohol moiety of the wax esters is formed from plant-endogenous acyl-CoAs by the action of fatty acyl reductases (FAR). In a second step the fatty alcohol is condensed with acyl-CoA by a wax synthase (WS) to form a wax ester. In order to evaluate the specificity of wax ester biosynthesis, analytical methods are needed that provide detailed wax ester profiles from complex lipid extracts. RESULTS: We present a direct infusion ESI-tandem MS method that allows the semi-quantitative determination of wax ester compositions from complex lipid mixtures covering 784 even chain molecular species. The definition of calibration prototype groups that combine wax esters according to their fragmentation behavior enables fast quantitative analysis by applying multiple reaction monitoring. This provides a tool to analyze wax layer composition or determine whether seeds accumulate a desired wax ester profile. Besides the profiling method, we provide general information on wax ester analysis by the systematic definition of wax ester prototypes according to their collision-induced dissociation spectra. We applied the developed method for wax ester profiling of the well characterized jojoba seed oil and compared the profile with wax ester-accumulating Arabidopsis thaliana expressing the wax ester biosynthetic genes MaFAR and ScWS. CONCLUSIONS: We developed a fast profiling method for wax ester analysis on the molecular species level. This method is suitable to screen large numbers of transgenic plants as well as other wax ester samples like cuticular lipid extracts to gain an overview on the molecular species composition. We confirm previous results from APCI-MS and GC-MS analysis, which showed that fragmentation patterns are highly dependent on the double bond distribution between the fatty alcohol and the fatty acid part of the wax ester.
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spelling pubmed-37662222013-09-12 Wax ester profiling of seed oil by nano-electrospray ionization tandem mass spectrometry Iven, Tim Herrfurth, Cornelia Hornung, Ellen Heilmann, Mareike Hofvander, Per Stymne, Sten Zhu, Li-Hua Feussner, Ivo Plant Methods Methodology BACKGROUND: Wax esters are highly hydrophobic neutral lipids that are major constituents of the cutin and suberin layer. Moreover they have favorable properties as a commodity for industrial applications. Through transgenic expression of wax ester biosynthetic genes in oilseed crops, it is possible to achieve high level accumulation of defined wax ester compositions within the seed oil to provide a sustainable source for such high value lipids. The fatty alcohol moiety of the wax esters is formed from plant-endogenous acyl-CoAs by the action of fatty acyl reductases (FAR). In a second step the fatty alcohol is condensed with acyl-CoA by a wax synthase (WS) to form a wax ester. In order to evaluate the specificity of wax ester biosynthesis, analytical methods are needed that provide detailed wax ester profiles from complex lipid extracts. RESULTS: We present a direct infusion ESI-tandem MS method that allows the semi-quantitative determination of wax ester compositions from complex lipid mixtures covering 784 even chain molecular species. The definition of calibration prototype groups that combine wax esters according to their fragmentation behavior enables fast quantitative analysis by applying multiple reaction monitoring. This provides a tool to analyze wax layer composition or determine whether seeds accumulate a desired wax ester profile. Besides the profiling method, we provide general information on wax ester analysis by the systematic definition of wax ester prototypes according to their collision-induced dissociation spectra. We applied the developed method for wax ester profiling of the well characterized jojoba seed oil and compared the profile with wax ester-accumulating Arabidopsis thaliana expressing the wax ester biosynthetic genes MaFAR and ScWS. CONCLUSIONS: We developed a fast profiling method for wax ester analysis on the molecular species level. This method is suitable to screen large numbers of transgenic plants as well as other wax ester samples like cuticular lipid extracts to gain an overview on the molecular species composition. We confirm previous results from APCI-MS and GC-MS analysis, which showed that fragmentation patterns are highly dependent on the double bond distribution between the fatty alcohol and the fatty acid part of the wax ester. BioMed Central 2013-07-06 /pmc/articles/PMC3766222/ /pubmed/23829499 http://dx.doi.org/10.1186/1746-4811-9-24 Text en Copyright © 2013 Iven et al.; licensee BioMed Central Ltd. http://creativecommons.org/licenses/by/2.0 This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Methodology
Iven, Tim
Herrfurth, Cornelia
Hornung, Ellen
Heilmann, Mareike
Hofvander, Per
Stymne, Sten
Zhu, Li-Hua
Feussner, Ivo
Wax ester profiling of seed oil by nano-electrospray ionization tandem mass spectrometry
title Wax ester profiling of seed oil by nano-electrospray ionization tandem mass spectrometry
title_full Wax ester profiling of seed oil by nano-electrospray ionization tandem mass spectrometry
title_fullStr Wax ester profiling of seed oil by nano-electrospray ionization tandem mass spectrometry
title_full_unstemmed Wax ester profiling of seed oil by nano-electrospray ionization tandem mass spectrometry
title_short Wax ester profiling of seed oil by nano-electrospray ionization tandem mass spectrometry
title_sort wax ester profiling of seed oil by nano-electrospray ionization tandem mass spectrometry
topic Methodology
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3766222/
https://www.ncbi.nlm.nih.gov/pubmed/23829499
http://dx.doi.org/10.1186/1746-4811-9-24
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