A recycling pathway for cyanogenic glycosides evidenced by the comparative metabolic profiling in three cyanogenic plant species

Pičmanová, Martina; Neilson, Elizabeth Heather Jakobsen; Motawia, Mohammed Saddik; Olsen, Carl Erik; Agerbirk, Niels; Gray, Christopher; Flitsch, Sabine L.; Meier, Sebastián; Silvestro, Daniele; Jørgensen, Kirsten; Sánchez‐Pérez, Raquel; Møller, Birger Lindberg; Bjarnholt, Nanna

doi:10.1042/bj20150390

Cited by 113 publications

(133 citation statements)

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“…Cyanogenesis is a plant chemical defense response to generalist herbivores involving the release of hydrogen cyanide following tissue disruption and hydrolysis of cyanogenic glycosides (CGs) [49, 50]. Endogenous recycling without cyanide release suggests that CGs serve additional biological roles including nitrogen and carbon supply at specific plant developmental stages [51] and there is evidence that intermediate compounds produced during biosynthesis of CGs have anti-microbial activity [52–54].…”

Section: Discussionmentioning

confidence: 99%

Genome and transcriptome sequencing characterises the gene space of Macadamia integrifolia (Proteaceae)

et al. 2016

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BackgroundThe large Gondwanan plant family Proteaceae is an early-diverging eudicot lineage renowned for its morphological, taxonomic and ecological diversity. Macadamia is the most economically important Proteaceae crop and represents an ancient rainforest-restricted lineage. The family is a focus for studies of adaptive radiation due to remarkable species diversification in Mediterranean-climate biodiversity hotspots, and numerous evolutionary transitions between biomes. Despite a long history of research, comparative analyses in the Proteaceae and macadamia breeding programs are restricted by a paucity of genetic information. To address this, we sequenced the genome and transcriptome of the widely grown Macadamia integrifolia cultivar 741.ResultsOver 95 gigabases of DNA and RNA-seq sequence data were de novo assembled and annotated. The draft assembly has a total length of 518 Mb and spans approximately 79% of the estimated genome size. Following annotation, 35,337 protein-coding genes were predicted of which over 90% were expressed in at least one of the leaf, shoot or flower tissues examined. Gene family comparisons with five other eudicot species revealed 13,689 clusters containing macadamia genes and 1005 macadamia-specific clusters, and provides evidence for linage-specific expansion of gene families involved in pathogen recognition, plant defense and monoterpene synthesis. Cyanogenesis is an important defense strategy in the Proteaceae, and a detailed analysis of macadamia gene homologues potentially involved in cyanogenic glycoside biosynthesis revealed several highly expressed candidate genes.ConclusionsThe gene space of macadamia provides a foundation for comparative genomics, gene discovery and the acceleration of molecular-assisted breeding. This study presents the first available genomic resources for the large basal eudicot family Proteaceae, access to most macadamia genes and opportunities to uncover the genetic basis of traits of importance for adaptation and crop improvement.Electronic supplementary materialThe online version of this article (doi:10.1186/s12864-016-3272-3) contains supplementary material, which is available to authorized users.

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Section: Discussionmentioning

confidence: 99%

Genome and transcriptome sequencing characterises the gene space of Macadamia integrifolia (Proteaceae)

et al. 2016

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“…In a subsequent reaction, a type 4 nitrilase catalyzes hydration of β-cyanoalanine resulting in the production of asparagine or aspartate and ammonia (Piotrowski, 2008). Evidence for the operation of two endogenous turnover pathways for cyanogenic glucosides has recently been provided (Pičmanová et al, 2015; Nielsen et al, 2016). In both these pathways, the nitrogen of the cyanogenic glucoside is recovered as ammonia without any release of hydrogen cyanide ( Figure 1D ).…”

Section: Introductionmentioning

confidence: 99%

“…Other potential physiological functions of CNglcs include a role as transporters of carbon and nitrogen (Selmar et al, 1988), suppliers of reduced nitrogen in form of ammonia (Sánchez-Pérez et al, 2008; Nielsen et al, 2016), as modulators of oxidative stress (Møller, 2010; Neilson et al, 2013) and as regulators of seed germination (Swain and Poulton, 1994b; Pičmanová et al, 2015). Seed germination is a developmental process closely related to bud dormancy release (Wareing and Saunders, 1971; Rohde and Bhalerao, 2007).…”

Section: Introductionmentioning

confidence: 99%

Cyanogenic Glucosides and Derivatives in Almond and Sweet Cherry Flower Buds from Dormancy to Flowering

et al. 2017

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Almond and sweet cherry are two economically important species of the Prunus genus. They both produce the cyanogenic glucosides prunasin and amygdalin. As part of a two-component defense system, prunasin and amygdalin release toxic hydrogen cyanide upon cell disruption. In this study, we investigated the potential role within prunasin and amygdalin and some of its derivatives in endodormancy release of these two Prunus species. The content of prunasin and of endogenous prunasin turnover products in the course of flower development was examined in five almond cultivars – differing from very early to extra-late in flowering time – and in one sweet early cherry cultivar. In all cultivars, prunasin began to accumulate in the flower buds shortly after dormancy release and the levels dropped again just before flowering time. In almond and sweet cherry, the turnover of prunasin coincided with increased levels of prunasin amide whereas prunasin anitrile pentoside and β-D-glucose-1-benzoate were abundant in almond and cherry flower buds at certain developmental stages. These findings indicate a role for the turnover of cyanogenic glucosides in controlling flower development in Prunus species.

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“…D. A. Webb. 9 These previous authors have suggested that these compounds along with their higher glycosylated derivatives and anitrile glycosides partake in a recycling pathway for the turnover of cyanogenic glycosides.…”

Section: ■ Results and Discussionmentioning

confidence: 98%

“…9 However, the fate of nitrile nitrogen and the role of enzymes in the proposed catabolism need to be resolved.…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

Occurrence of Benzoic Acid Esters as Putative Catabolites of Prunasin in Senescent Leaves of Prunus laurocerasus

2016

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Prunus laurocerasus is an evergreen shrub containing large quantities of the cyanogenic glycoside prunasin (1) in its leaves, which decomposes to prunasin amide (2) or glucose-1-benzoate (4) when the leaves become chlorotic as a result of senescence or pseudosenescence. This study was aimed at the systematic identification of senescence-associated metabolites to contribute further insight into the catabolism of 1. LC-ESIMS profiles of senescent and green leaves were analyzed by principal component analysis. In senescent leaves, the concentrations of 36 compounds were increased significantly including several benzoic acid derivatives, of which prunasin amide-6'-benzoate (5) and prunasin acid-6'-benzoate (6) were isolated and identified. The observed metabolic changes were also induced by treatment of P. laurocerasus shrubs with exogenous ethylene. The data presented support an oxidative catabolism of 1 without release of hydrogen cyanide and the remobilization of its nitrogen in the course of senescence. The results are discussed in the context of functional diversification and drug discovery, where senescent plant material represents a widely unexplored source for the discovery of natural products.

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A recycling pathway for cyanogenic glycosides evidenced by the comparative metabolic profiling in three cyanogenic plant species

Cited by 113 publications

References 69 publications

Genome and transcriptome sequencing characterises the gene space of Macadamia integrifolia (Proteaceae)

Genome and transcriptome sequencing characterises the gene space of Macadamia integrifolia (Proteaceae)

Cyanogenic Glucosides and Derivatives in Almond and Sweet Cherry Flower Buds from Dormancy to Flowering

Occurrence of Benzoic Acid Esters as Putative Catabolites of Prunasin in Senescent Leaves of Prunus laurocerasus

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