Cyanogenic glycosides are phytoanticipins involved in plant defence against herbivores by virtue of their ability to release toxic hydrogen cyanide (HCN) upon tissue disruption. In addition, endogenous turnover of cyanogenic glycosides without the liberation of HCN may offer plants an important source of reduced nitrogen at specific developmental stages. To investigate the presence of putative turnover products of cyanogenic glycosides, comparative metabolic profiling using LC–MS/MS and high resolution MS (HR–MS) complemented by ion-mobility MS was carried out in three cyanogenic plant species: cassava, almond and sorghum. In total, the endogenous formation of 36 different chemical structures related to the cyanogenic glucosides linamarin, lotaustralin, prunasin, amygdalin and dhurrin was discovered, including di- and tri-glycosides derived from these compounds. The relative abundance of the compounds was assessed in different tissues and developmental stages. Based on results common to the three phylogenetically unrelated species, a potential recycling endogenous turnover pathway for cyanogenic glycosides is described in which reduced nitrogen and carbon are recovered for primary metabolism without the liberation of free HCN. Glycosides of amides, carboxylic acids and ‘anitriles’ derived from cyanogenic glycosides appear as common intermediates in this pathway and may also have individual functions in the plant. The recycling of cyanogenic glycosides and the biological significance of the presence of the turnover products in cyanogenic plants open entirely new insights into the multiplicity of biological roles cyanogenic glycosides may play in plants.
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Research Article|
July 23 2015
A recycling pathway for cyanogenic glycosides evidenced by the comparative metabolic profiling in three cyanogenic plant species
Martina Pičmanová;
Martina Pičmanová
*Plant Biochemistry Laboratory, Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Copenhagen, Denmark
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Elizabeth H. Neilson;
Elizabeth H. Neilson
*Plant Biochemistry Laboratory, Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Copenhagen, Denmark
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Mohammed S. Motawia;
Mohammed S. Motawia
*Plant Biochemistry Laboratory, Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Copenhagen, Denmark
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Carl Erik Olsen;
Carl Erik Olsen
*Plant Biochemistry Laboratory, Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Copenhagen, Denmark
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Niels Agerbirk;
Niels Agerbirk
*Plant Biochemistry Laboratory, Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Copenhagen, Denmark
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Christopher J. Gray;
Christopher J. Gray
†School of Chemistry, Manchester Institute of Biotechnology, University of Manchester, 131 Princess Street, Manchester M1 7DN, U.K.
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Sabine Flitsch;
Sabine Flitsch
†School of Chemistry, Manchester Institute of Biotechnology, University of Manchester, 131 Princess Street, Manchester M1 7DN, U.K.
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Sebastian Meier;
Sebastian Meier
‡Department of Chemistry, Technical University of Denmark, Kemitorvet, 2800, Kgs. Lyngby, Denmark
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Daniele Silvestro;
Daniele Silvestro
§Copenhagen Plant Science Center (CPSC), Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Copenhagen, Denmark
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Kirsten Jørgensen;
Kirsten Jørgensen
*Plant Biochemistry Laboratory, Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Copenhagen, Denmark
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Raquel Sánchez-Pérez;
Raquel Sánchez-Pérez
*Plant Biochemistry Laboratory, Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Copenhagen, Denmark
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Birger Lindberg Møller;
Birger Lindberg Møller
1
*Plant Biochemistry Laboratory, Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Copenhagen, Denmark
¶Carlsberg Laboratory, Gamle Carlsberg Vej 10, 1799 Copenhagen V, Denmark
1To whom correspondence should be addressed (email blm@plen.ku.dk).
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Nanna Bjarnholt
Nanna Bjarnholt
*Plant Biochemistry Laboratory, Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Copenhagen, Denmark
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Publisher: Portland Press Ltd
Received:
March 27 2015
Revision Received:
May 26 2015
Accepted:
May 28 2015
Accepted Manuscript online:
June 10 2015
Online ISSN: 1470-8728
Print ISSN: 0264-6021
© 2015 Authors; published by Portland Press Limited
2015
Biochem J (2015) 469 (3): 375–389.
Article history
Received:
March 27 2015
Revision Received:
May 26 2015
Accepted:
May 28 2015
Accepted Manuscript online:
June 10 2015
Citation
Martina Pičmanová, Elizabeth H. Neilson, Mohammed S. Motawia, Carl Erik Olsen, Niels Agerbirk, Christopher J. Gray, Sabine Flitsch, Sebastian Meier, Daniele Silvestro, Kirsten Jørgensen, Raquel Sánchez-Pérez, Birger Lindberg Møller, Nanna Bjarnholt; A recycling pathway for cyanogenic glycosides evidenced by the comparative metabolic profiling in three cyanogenic plant species. Biochem J 1 August 2015; 469 (3): 375–389. doi: https://doi.org/10.1042/BJ20150390
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