Gynocardin from Baileyoxylon lanceolatum and a revision of cyanogenic glycosides in Achariaceae

Webber, Bruce L.; Miller, Rebecca

doi:10.1016/j.bse.2008.03.011

Cited by 9 publications

(6 citation statements)

References 59 publications

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“…Although common among wild and cultivated plant species (Jones, 1998; Møller & Seigler, 1999; Webber & Miller, 2008), the function of cyanogenesis in the interaction with herbivores is not fully understood (reviewed by Gleadow & Woodrow, 2002). While some herbivores are effectively repelled by plant cyanogenesis, others seem unaffected (e.g., Ferreira et al., 1997), or plant cyanide might even act as phagostimulant rather than feeding deterrent (Fitzgerald et al., 2002).…”

Section: Discussionmentioning

confidence: 99%

“…Among higher plants, synthesis of cyanide‐containing compounds is a widely distributed direct defence. Over 3 000 species, representing more than 550 genera and 130 families, produce and accumulate cyanide‐containing compounds (Møller & Seigler, 1999; Webber & Miller, 2008). Cyanogenesis means the enzymatically accelerated release of toxic hydrogen cyanide from inactive cyanide‐containing components in response to cell damage.…”

Section: Introductionmentioning

confidence: 99%

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Comparing responses of generalist and specialist herbivores to various cyanogenic plant features

Ballhorn

Kautz

Lieberei

2010

Entomologia Exp Applicata

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Plants are obliged to defend themselves against multiple generalist and specialist herbivores. Whereas plant cyanogenesis is considered an efficient defence against generalists, it is thought to affect specialists less. In the present study, we analysed the function of various cyanogenic features of lima bean [Phaseolus lunatus L. (Fabaceae)] during interaction with different herbivores. Three cyanogenic features were analysed, i.e., cyanogenic potential (HCNp; concentration of cyanogenic precursors), b-glucosidase activity, and cyanogenic capacity (HCNc; release of cyanide per unit time). In nochoice and free-choice feeding trials, five lima bean accessions were offered to generalist desert locust [Schistocerca gregaria Forskål (Orthoptera: Acrididae)] and specialist Mexican bean beetle [Epilachna varivestis Mulsant (Coleoptera: Coccinellidae)]. The HCNc was the most important parameter determining host plant selection by generalists, whereas choice behaviour of specialists was strongly affected by HCNp. Although locusts were effectively repelled by high HCNc, this cue was misleading for the detection of suitable host plants, as extensive consumption of low HCNc plant material resulted in strong intoxication of locusts. Balancing cyanide in consumed leaf area, the quantitative release of gaseous cyanide during feeding, and cyanide in faeces suggested that specialists metabolized significantly lower rates of cyanide per consumed leaf material than generalists. We hypothesize that specialists are able to avoid toxic concentrations of cyanide by using HCNp rather than HCNc as a cue for host plant quality, and that they exhibit mechanisms that reduce incorporation of host plant cyanide.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Comparing responses of generalist and specialist herbivores to various cyanogenic plant features

Ballhorn

Kautz

Lieberei

2010

Entomologia Exp Applicata

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“…Among them, gynocardin and mintsulfide were up-regulated by 14.72 and 12.29 times, respectively, compared to NK ( Table 5 ). Gynocardin is the first cyclopentenoid glycoside discovered in plants, and its chemical structure has been determined ( Webber and Miller, 2008 ), and cyclopentenone is the glycoside ligand of gynocardin, containing a cyanide group toxic to plants, which might be one of the reasons why the total length, surface area, and volume of roots significantly decreased under LK stress ( Siegieñ and Bogatek, 2006 ). In Pangium edule Reinw, soil condition affects the content of gynocardin ( Yuningsih, 2008 ).…”

Section: Discussionmentioning

confidence: 99%

Metabolite Profile of Xylem Sap in Cotton Seedlings Is Changed by K Deficiency

et al. 2020

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Xylem sap, belonging to the plant apoplast, not only provides plant tissues with inorganic and organic substances but also facilitates communication between the roots and the leaves and coordinates their development. This study investigated the effects of potassium (K) deficiency on the morphology and the physiology of cotton seedlings as well as pH, mineral nutrient contents, and metabolites of xylem sap. In particular, we compared changes in root–shoot communication under low K (LK) and normal K (NK, control) levels. Compared to control, LK stress significantly decreased seedling biomass (leaf, stem, and root dry weight; stem and root length; root surface area and root volume) and the levels of K, Na (sodium), Mg (magnesium), Fe (iron), and Zn (zinc) in xylem sap. A total of 82 metabolites in sap analyzed by high-performance liquid chromatography–tandem mass spectrometry (HPLC–MS/MS) showed significant differences between the two conditions; among these, 38 were up-regulated more than 2-fold, while the others were down-regulated less than 0.5-fold. In particular, several metabolites found in the cell membrane including three cholines (glycerophosphatecholine, 2-hexenylcholine, and caproylcholine) and desglucocoroloside and others such as malondialdehyde, α-amino acids and derivatives, sucrose, and sugar alcohol significantly increased under LK stress, indicating that cell membranes were damaged and protein metabolism was abnormal. It is worth noting that glycerophosphocholine was up-regulated 29-fold under LK stress, indicating that it can be used as an important signal of root–shoot communication. Furthermore, in pathway analyses, 26 metabolites were matched to Kyoto Encyclopedia of Genes and Genomes (KEGG) pathways; L-aspartic acid, which was associated with 10 KEGG pathways, was the most involved metabolite. Overall, K deficiency reduced the antioxidant capacity of cotton seedlings and led to a metabolic disorder including elevated levels of primary metabolites and inhibited production of secondary metabolites. This eventually resulted in decreased biomass of cotton seedlings under LK stress. This study lays a solid foundation for further research on targeted metabolites and signal substances in the xylem sap of cotton plants exposed to K deficiency.

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“…This phenomenon, cyanogenesis, is widespread in the plant kingdom ( Møller and Seigler, 1999 ). More than 3000 cyanogenic plant species have been described ( Seigler and Brinker, 1993 ; Webber and Miller, 2008 ), including many economically important crops such as cassava ( Manihot esculenta ), sorghum ( Sorghum bicolor ), lima bean ( Phaseolus lunatus ), white clover ( Trifolium repens ) and the rubber tree Hevea brasiliensis ( McMahon et al , 1995 ). HCN is highly toxic due to inhibition of the mitochondrial respiration pathway (e.g.…”

Section: Introductionmentioning

confidence: 99%

The cyanogenic syndrome in rubber tree Hevea brasiliensis: tissue-damage-dependent activation of linamarase and hydroxynitrile lyase accelerates hydrogen cyanide release

et al. 2012

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Background and AimsThe release of hydrogen cyanide (HCN) from injured plant tissue affects multiple ecological interactions. Plant-derived HCN can act as a defence against herbivores and also plays an important role in plant–pathogen interactions. Crucial for activity as a feeding deterrent is the amount of HCN generated per unit time, referred to as cyanogenic capacity (HCNc). Strong intraspecific variation in HCNc has been observed among cyanogenic plants. This variation, in addition to genotypic variability (e.g. in Trifolium repens), can result from modifications in the expression level of the enzymes involved in either cyanogenic precursor formation or HCN release (as seen in Sorghum bicolor and Phaseolus lunatus). Thus, a modification or modulation of HCNc in reaction to the environment can only be achieved from one to the next generation when under genetic control and within days or hours when transcriptional regulations are involved. In the present study, it is shown that in rubber tree (Hevea brasiliensis) HCNc is modulated by post-translational activity regulation of the key enzymes for cyanide release.MethodsLinamarase (LIN) and hydroxynitrile lyase (HNL) activity was determined by colorimetric assays utilizing dissociation of the substrates p-nitrophenyl-β-d-glucopyranoside and acetone cyanohydrin, respectively.Key ResultsIn rubber tree leaves, LIN and HNL show up to ten-fold increased activity in response to tissue damage. This enzyme activation occurs within seconds and results in accelerated HCN formation. It is restricted to the damaged leaf area and depends on the severity of tissue damage.ConclusionsLIN and HNL activation (in contrast to genetic and transcriptional regulations) allows an immediate, local and damage type-dependent modulation of the cyanogenic response. Accordingly, this post-translational activation plays a decisive role in the defence of H. brasiliensis against herbivores as well as pathogens and may allow more flexible reactions in response to these different antagonists.

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Gynocardin from Baileyoxylon lanceolatum and a revision of cyanogenic glycosides in Achariaceae

Cited by 9 publications

References 59 publications

Comparing responses of generalist and specialist herbivores to various cyanogenic plant features

Comparing responses of generalist and specialist herbivores to various cyanogenic plant features

Metabolite Profile of Xylem Sap in Cotton Seedlings Is Changed by K Deficiency

The cyanogenic syndrome in rubber tree Hevea brasiliensis: tissue-damage-dependent activation of linamarase and hydroxynitrile lyase accelerates hydrogen cyanide release

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