The cyanogenic glucoside composition of Zygaena filipendulae (Lepidoptera: Zygaenidae) as effected by feeding on wild-type and transgenic lotus populations with variable cyanogenic glucoside profiles

Zagrobelny, Mika; Bak, Søren; Ekstrøm, Claus Thorn; Olsen, Carl Erik; Møller, Birger Lindberg

doi:10.1016/j.ibmb.2006.09.008

Cited by 67 publications

(102 citation statements)

References 32 publications

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“…These results demonstrate that the linamarin to lotaustralin ratio present in Zygaena larvae partly reflects the ratio in their dietary plants (Zagrobelny et al 2007). …”

Section: Expression Ofmentioning

confidence: 69%

“…When Z. filipendulae larvae were reared on L. japonicus wild type and L. japonicus 35S::CYP79D2, an increase in linamarin to lotaustralin ratio was observed in the larvae fed on L. japonicus 35S::CYP79D2 compared to wild type (Zagrobelny et al 2007). These results demonstrate that the linamarin to lotaustralin ratio present in Zygaena larvae partly reflects the ratio in their dietary plants (Zagrobelny et al 2007).…”

Section: Expression Ofmentioning

confidence: 97%

“…This would provide useful tools to dissect unknown functions of cyanogenic glucosides and rhodiocyanosides in plant fitness and adaption to biotic and abiotic stresses. They may also approve valuable in unravelling the impact of cyanogenic glucosides and rhodiocyanosides in interactions with Zygaena larvae and plant development (Zagrobelny et al 2004;Zagrobelny et al 2007). …”

Section: Why Does L Japonicus Silence the Dhurrin Pathway?mentioning

confidence: 99%

“…While rhodiocyanoside A and D are degraded by the same bglucosidases that degrade the cyanogenic glucosides (our unpublished results), hydrolysis is not accompanied by release of HCN, as rhodiocyanosides are not derived from a-hydroxynitriles (cyanohydrins). While the ability to produce linamarin and lotaustralin is widespread in Lotus species, the ability to produce rhodiocyanosides appears to be limited to L. japonicus (Zagrobelny et al 2007 Fabaceous plants including Lotus species and sequester the cyanogenic glucosides for use in their own defense against predators. In the absence of sufficient amounts of cyanogenic glucosides in their dietary plants, the larvae possess the ability to de novo synthesize the very same cyanogenic glucosides, linamarin and lotaustralin, as present in Lotus species, albeit with a resultant concomitant reduction in growth rate (Zagrobelny et al 2004).…”

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confidence: 99%

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Lessons learned from metabolic engineering of cyanogenic glucosides

Morant¹,

Jørgensen²,

Jørgensen³

et al. 2007

Metabolomics

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Plants produce a plethora of secondary metabolites which constitute a wealth of potential pharmaceuticals, pro-vitamins, flavours, fragrances, colorants and toxins as well as a source of natural pesticides. Many of these valuable compounds are only synthesized in exotic plant species or in concentrations too low to facilitate commercialization. In some cases their presence constitutes a health hazard and renders the crops unsuitable for consumption. Metabolic engineering is a powerful tool to alter and ameliorate the secondary metabolite composition of crop plants and gain new desired traits. The interplay of a multitude of biosynthetic pathways and the possibility of metabolic cross-talk combined with an incomplete understanding of the regulation of these pathways, explain why metabolic engineering of plant secondary metabolism is still in its infancy and subject to much trial and error. Cyanogenic glucosides are ancient defense compounds that release toxic HCN upon tissue disruption caused e.g. by chewing insects. The committed steps of the cyanogenic glucoside biosynthetic pathway are encoded by three genes. This unique genetic simplicity and the availability of the corresponding cDNAs have given cyanogenic glucosides pioneering status in metabolic engineering of plant secondary metabolism. In this review, lessons learned from metabolic engineering of cyanogenic glucosides in Arabidopsis thaliana (thale cress), Nicotiana tabacum cv Xanthi (tobacco), Manihot esculenta Crantz (cassava) and Lotus japonicus (bird's foot trefoil) are presented. The importance of metabolic channelling of toxic intermediates as mediated by metabolon formation in avoiding unintended metabolic cross-talk and unwanted pleiotropic effects is emphasized. Likewise, the potential of metabolic engineering of plant secondary metabolism as a tool to elucidate, for example, the impact of secondary metabolites on plant-insect interactions is demonstrated.

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“…These results demonstrate that the linamarin to lotaustralin ratio present in Zygaena larvae partly reflects the ratio in their dietary plants (Zagrobelny et al 2007). …”

Section: Expression Ofmentioning

confidence: 69%

Section: Expression Ofmentioning

confidence: 97%

Section: Why Does L Japonicus Silence the Dhurrin Pathway?mentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Lessons learned from metabolic engineering of cyanogenic glucosides

Morant¹,

Jørgensen²,

Jørgensen³

et al. 2007

Metabolomics

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“…Upon disruption of plant tissue containing cyanogenic glucosides, these are typically hydrolyzed by b-glucosidases with concomitant release of Glc, an aldehyde or ketone, and HCN. This two-component system, of which each of the separate components is chemically inert, provides plants with an immediate chemical defense against attacking herbivores and pathogens (Conn, 1969;Nahrstedt, 1985;Jones, 1988;Morant et al, 2003;Nielsen et al, 2006;Zagrobelny et al, 2004Zagrobelny et al, , 2007aZagrobelny et al, , 2007b). In addition to their possible defense function, accumulation of cyanogenic glucosides in certain angiosperm seeds may provide a storage deposit of reduced nitrogen and sugar for the developing seedlings (Lieberei et al, 1985;Selmar et al, 1988Selmar et al, , 1990Swain et al, 1992).…”

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confidence: 99%

Bitterness in Almonds

et al. 2008

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Bitterness in almond (Prunus dulcis) is determined by the content of the cyanogenic diglucoside amygdalin. The ability to synthesize and degrade prunasin and amygdalin in the almond kernel was studied throughout the growth season using four different genotypes for bitterness. Liquid chromatography-mass spectrometry analyses showed a specific developmentally dependent accumulation of prunasin in the tegument of the bitter genotype. The prunasin level decreased concomitant with the initiation of amygdalin accumulation in the cotyledons of the bitter genotype. By administration of radiolabeled phenylalanine, the tegument was identified as a specific site of synthesis of prunasin in all four genotypes. A major difference between sweet and bitter genotypes was observed upon staining of thin sections of teguments and cotyledons for b-glucosidase activity using Fast Blue BB salt. In the sweet genotype, the inner epidermis in the tegument facing the nucellus was rich in cytoplasmic and vacuolar localized b-glucosidase activity, whereas in the bitter cultivar, the b-glucosidase activity in this cell layer was low. These combined data show that in the bitter genotype, prunasin synthesized in the tegument is transported into the cotyledon via the transfer cells and converted into amygdalin in the developing almond seed, whereas in the sweet genotype, amygdalin formation is prevented because the prunasin is degraded upon passage of the b-glucosidaserich cell layer in the inner epidermis of the tegument. The prunasin turnover may offer a buffer supply of ammonia, aspartic acid, and asparagine enabling the plants to balance the supply of nitrogen to the developing cotyledons.

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Biosynthesis of Cyanogenic Glycosides, Glucosinolates and Non‐Protein Amino Acids

Selmar¹

2018

Annual Plant Reviews Online

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When cyanogenic plants are injured, hydrogen cyanide (HCN) is liberated. This cyanogenesis is initiated by any decompartmentation, resulting in the contact of cyanogenic glycosides and the corresponding β‐glucosidases. The related hydrolysis produces unstable hydroxynitriles which decay to HCN and a carbonyl. This treatise reviews the various plant biological, biochemical and molecular facets of cyanogenic glucosides; special emphasis is put on the new and actual aspects of their biosynthesis. In the past, this complex conversion of amino acids via aldoximes to cyanogenic glucosides was described as so‐called channelled biosynthesis. Yet, later on, it was shown that this multi‐step biosynthesis is performed by only two multi‐functional cytochrome P450 enzymes, which are located in the ER. Subsequently, the resulting unstable hydroxynitriles are glucosylated by soluble cytosolic glucosyltransferase. Just recently, the ‘missing link’ between the cytochrome‐dependent synthesis and the final glucosylation step could be elucidated in Birger Møller's lab by the discovery of a metabolon that comprises all biosynthetic steps. Thus, the old concept of ‘channelled biosynthesis’ does apply again.Glucosinolates, which resemble cyanogenic compounds in many aspects, are characterized by the liberation of mustard oils, a complex mixture of isothiocyanates, thiocyanates and related nitriles. Degradation takes place when tissues of glucosinolate‐containing plants are damaged and cells are destroyed. Glucosinolates and their degradation products are important factors in plant defence against herbivores, as well as against pathogens. The biosynthesis of glucosinolates includes three independent phases: first, the chain elongation of amino acids; second, conversion of the precursor amino acid via aldoximes into glucosinolates; and, finally, further modifications of the resulting glucosinolates. In the past, for a long time the formation of aldoximes from amino acids was discussed controversially and three different pathways had been proposed, one involving flavin‐containing mono‐oxygenases, another one membrane‐bound peroxidases and a third one in which – similar to the biosynthesis of cyanogenic glucosides – the aldoximes are produced by cytochrome P450s. Meanwhile, due to the tremendous progress by molecular biology and molecular genetics, it was shown that only the P450‐related synthesis is relevant. This review emphasizes on the biochemical and molecular aspects of glucosinolate biosynthesis, but does also outline the mustard oil formation, its ecological relevance and important nutritional aspects.Apart from the amino acids present in proteins, numerous other amino acids occur in plants. Whereas some of them are known to be intermediates in various pathways of primary metabolism, others are regarded as typical secondary metabolites with the corresponding ecological functions. In contrast to the comprehensive knowledge of cyanogenic glucosides and glucosinolates, far less is known about the biology and biochemistry of non‐protein amino acids (NPAAs). The corresponding part of this chapter reviews the recent knowledge on the various aspects of NPAAs, including their biosynthesis and metabolism and their putative ecological significance.

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The cyanogenic glucoside composition of Zygaena filipendulae (Lepidoptera: Zygaenidae) as effected by feeding on wild-type and transgenic lotus populations with variable cyanogenic glucoside profiles

Cited by 67 publications

References 32 publications

Lessons learned from metabolic engineering of cyanogenic glucosides

Lessons learned from metabolic engineering of cyanogenic glucosides

Bitterness in Almonds

Biosynthesis of Cyanogenic Glycosides, Glucosinolates and Non‐Protein Amino Acids

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