Glucosinolate structures in evolution |
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| Institution: | 1. Department of Chemical Ecology, Bielefeld University, Universitätsstr. 25, 33615 Bielefeld, Germany;2. Center for Biotechnology and Department for Proteome and Metabolome Research, Bielefeld University, Universitätsstr. 27, 33615 Bielefeld, Germany;1. Molecular Interaction Ecology, Institute of Water and Wetland Research (IWWR), Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands;2. Synthetic Organic Chemistry, Institute for Molecules and Materials (IMM), Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands;3. Physical Organic Chemistry, Institute for Molecules and Materials (IMM), Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands;4. Department of Plant Sciences, University of Oxford, South Parks Road, OX1 3RB, UK;5. Bio-Organic Chemistry, Institute for Molecules and Materials (IMM), Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands;6. Laboratory of Genetics, Wageningen University, Droevendaalsesteeg 1, 6708 PB Wageningen, The Netherlands;7. German Centre for Integrative Biodiversity Research (iDiv) Halle-Jena-Leipzig, Deutscher Platz 5e, 04103 Leipzig, Germany;8. Friedrich Schiller University Jena, Institute of Ecology, Dornburger-Str. 159, 07743 Jena, Germany;9. Department of Microbiology, Institute of Water and Wetland Research (IWWR), Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands |
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| Abstract: | By 2000, around 106 natural glucosinolates (GSLs) were probably documented. In the past decade, 26 additional natural GSL structures have been elucidated and documented. Hence, the total number of documented GSLs from nature by 2011 can be estimated to around 132. A considerable number of additional suggested structures are concluded not to be sufficiently documented. In many cases, NMR spectroscopy would have provided the missing structural information. Of the GSLs documented in the past decade, several are of previously unexpected structures and occur at considerable levels. Most originate from just four species: Barbarea vulgaris, Arabidopsis thaliana, Eruca sativa and Isatis tinctoria. Acyl derivatives of known GSLs comprised 15 of the 26 newly documented structures, while the remaining exhibited new substitution patterns or chain length, or contained a mercapto group or related thio-functionality.GSL identification methods are reviewed, and the importance of using authentic references and structure-sensitive detection methods such as MS and NMR is stressed, especially when species with relatively unknown chemistry are analyzed. An example of qualitative GSL analysis is presented with experimental details (group separation and HPLC of both intact and desulfated GSLs, detection and structure determination by UV, MS, NMR and susceptibility to myrosinase) with emphasis on the use of NMR for structure elucidation of even minor GSLs and GSL hydrolysis products. The example includes identification of a novel GSL, (R)-2-hydroxy-2-(3-hydroxyphenyl)ethylglucosinolate.Recent investigations of GSL evolution, based on investigations of species with well established phylogeny, are reviewed. From the relatively few such investigations, it is already clear that GSL profiles are regularly subject to evolution. This result is compatible with natural selection for specific GSL side chains. The probable existence of structure-specific GSL catabolism in intact plants suggests that biochemical evolution of GSLs has more complex implications than the mere liberation of a different hydrolysis product upon tissue disruption. |
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