1932

Abstract

Cyanogenic glycosides (CNglcs) are bioactive plant products derived from amino acids. Structurally, these specialized plant compounds are characterized as α-hydroxynitriles (cyanohydrins) that are stabilized by glucosylation. In recent years, improved tools within analytical chemistry have greatly increased the number of known CNglcs by enabling the discovery of less abundant CNglcs formed by additional hydroxylation, glycosylation, and acylation reactions. Cyanogenesis—the release of toxic hydrogen cyanide from endogenous CNglcs—is an effective defense against generalist herbivores but less effective against fungal pathogens. In the course of evolution, CNglcs have acquired additional roles to improve plant plasticity, i.e., establishment, robustness, and viability in response to environmental challenges. CNglc concentration is usually higher in young plants, when nitrogen is in ready supply, or when growth is constrained by nonoptimal growth conditions. Efforts are under way to engineer CNglcs into some crops as a pest control measure, whereas in other crops efforts are directed toward their removal to improve food safety. Given that many food crops are cyanogenic, it is important to understand the molecular mechanisms regulating cyanogenesis so that the impact of future environmental challenges can be anticipated.

[Erratum, Closure]

An erratum has been published for this article:
Cyanogenic Glycosides: Synthesis, Physiology, and Phenotypic Plasticity
Loading

Article metrics loading...

/content/journals/10.1146/annurev-arplant-050213-040027
2014-04-29
2024-04-16
Loading full text...

Full text loading...

/deliver/fulltext/arplant/65/1/annurev-arplant-050213-040027.html?itemId=/content/journals/10.1146/annurev-arplant-050213-040027&mimeType=html&fmt=ahah

Literature Cited

  1. Adewusi SRA. 1.  1990. Turnover of dhurrin in green sorghum seedlings. Plant Physiol. 94:1219–24 [Google Scholar]
  2. Agrawal AA. 2.  2011. New synthesis—trade-offs in chemical ecology. J. Chem. Ecol. 37:230–31 [Google Scholar]
  3. Agrawal AA, Hastings AP, Johnson MTJ, Maron JL, Salminen J-P. 3.  2012. Insect herbivores drive real-time ecological and evolutionary change in plant populations. Science 338:113–16 [Google Scholar]
  4. Ahn YO, Saino H, Mizutani M, Shimizu B, Sakata K. 4.  2007. Vicianin hydrolase is a novel cyanogenic β-glycosidase specific to β-vicianoside (6-O-α-l-arabinopyranosyl-β-d-glucopyranoside) in seeds of Vicia angustifolia. Plant Cell Physiol. 48:938–39 [Google Scholar]
  5. Alves AAC, Setter TL. 5.  2004. Abscisic acid accumulation and osmotic adjustment in cassava under water deficit. Environ. Exp. Bot. 51:259–71 [Google Scholar]
  6. Andersen MD, Busk PK, Svendsen I, Møller BL. 6.  2000. Cytochromes P450 from cassava (Manihot esculenta Crantz) catalyzing the first steps in the biosynthesis of the cyanogenic glucosides linamarin and lotaustralin: cloning, functional expression in Pichia pastoris, and substrate specificity of the isolated recombinant enzymes. J. Biol. Chem. 275:1966–75 [Google Scholar]
  7. Bak S, Beisson F, Bishop G, Hamberger B, Höfer R. 7.  et al. 2011. Cytochromes P450. Arabidopsis Book 9:e0144 [Google Scholar]
  8. Bak S, Kahn RA, Nielsen HN, Møller BL, Halkier BA. 8.  1998. Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin. Plant Mol. Biol. 36:393–405 [Google Scholar]
  9. Bak S, Paquette S, Morant M, Morant A, Saito S. 9.  et al. 2006. Cyanogenic glycosides: a case study for evolution and application of cytochromes P450. Phytochem. Rev. 5:309–29 [Google Scholar]
  10. Ballhorn DJ. 10.  2011. Constraints of simultaneous resistance to a fungal pathogen and an insect herbivore in lima bean (Phaseolus lunatus L.). J. Chem. Ecol. 37:141–44 [Google Scholar]
  11. Ballhorn DJ, Heil M, Lieberei R. 11.  2006. Phenotypic plasticity of cyanogenesis in lima bean Phaseolus lunatus—activity and activation of β-glucosidase. J. Chem. Ecol. 32:261–75 [Google Scholar]
  12. Ballhorn DJ, Kautz S, Jensen M, Schmitt I, Heil M, Hegeman AD. 12.  2011. Genetic and environmental interactions determine plant defences against herbivores. J. Ecol. 99:313–26 [Google Scholar]
  13. Ballhorn DJ, Kautz S, Lion U, Heil M. 13.  2008. Trade-offs between direct and indirect defences of lima bean (Phaseolus lunatus). J. Ecol. 96:971–80 [Google Scholar]
  14. Ballhorn DJ, Kautz S, Schädler M. 14.  2013. Induced plant defense via volatile production is dependent on rhizobial symbiosis. Oecologia 172:833–46 [Google Scholar]
  15. Ballhorn DJ, Lieberei R, Ganzhorn JU. 15.  2005. Plant cyanogenesis of Phaseolus lunatus and its relevance for herbivore-plant interaction: the importance of quantitative data. J. Chem. Ecol. 31:1445–73 [Google Scholar]
  16. Ballhorn DJ, Pietrowski A, Lieberei R. 16.  2010. Direct trade-off between cyanogenesis and resistance to a fungal pathogen in lima bean (Phaseolus lunatus L.). J. Chem. Ecol. 98:226–36Shows that the trade-off between the production of CNglcs and volatile organic compounds results from the balance between relative rates of herbivory and pathogen attack. [Google Scholar]
  17. Ballhorn DJ, Schiwy S, Jensen M, Heil M. 17.  2008. Quantitative variability of direct chemical defense in primary and secondary leaves of lima bean (Phaseolus lunatus) and consequences for a natural herbivore. J. Chem. Ecol. 34:1298–301 [Google Scholar]
  18. Bari R, Jones JDG. 18.  2009. Role of plant hormones in plant defence responses. Plant Mol. Biol. 69:473–88 [Google Scholar]
  19. Barnett RD, Caviness CE. 19.  1968. Inheritance of hydrocyanic acid production in two sorghum × sudangrass crosses. Crop Sci. 8:89–91 [Google Scholar]
  20. Barros PM, Gonçalves N, Saibo NJM, Oliveira MM. 20.  2012. Cold acclimation and floral development in almond bud break: insights into the regulatory pathways. J. Exp. Bot. 63:4585–96 [Google Scholar]
  21. Basile LJ, Willson RC, Sewell BT. 21.  2008. Genome mining of cyanide-degrading nitrilases from filamentous fungi. Appl. Microbiol. Biotechnol. 80:427–35 [Google Scholar]
  22. Bazin A, Goverde M, Erhardt A, Shykoff JA. 22.  2002. Influence of atmospheric carbon dioxide enrichment on induced response and growth compensation after herbivore damage in Lotus corniculatus. Ecol. Entomol. 27:271–78 [Google Scholar]
  23. Bjarnholt N, Laegdsmand M, Hansen HC, Jacobsen OH, Møller BL. 23.  2008. Leaching of cyanogenic glucosides and cyanide from white clover green manure. Chemosphere 72:897–904 [Google Scholar]
  24. Bjarnholt N, Møller BL. 24.  2008. Hydroxynitrile glucosides. Phytochemistry 69:1947–61 [Google Scholar]
  25. Blomstedt CK, Gleadow RM, O'Donnell N, Naur P, Jensen K. 25.  et al. 2012. A combined biochemical screen and TILLING approach identifies mutations in Sorghum bicolor L. Moench resulting in acyanogenic forage production. Plant Biotechnol. J. 10:54–66Uses ethyl methanesulfonate–generated sorghum mutants with altered cyanogenic status to provide a new crop model for study. [Google Scholar]
  26. Blumenthal SG, Hendrickson HR, Abrol YP, Conn EE. 26.  1968. Cyanide metabolism in higher plants. III. The biosynthesis of β-cyanoalanine. J. Biol. Chem. 243:5302–7 [Google Scholar]
  27. Briggs MA. 27.  1990. Chemical defense production in Lotus corniculatus L. I. The effects of nitrogen source on growth, reproduction and defense. Oecologia 83:27–31 [Google Scholar]
  28. Brown A. 28.  2011. Effect of temperature and drought on the growth and nutritive value of cassava Hon. Thesis, Monash Univ., Victoria, Aust.
  29. Buchanan CD, Lim S, Salzman RA, Kagiampakis I, Morishige DT. 29.  et al. 2010. Sorghum bicolor's transcriptome response to dehydration, high salinity and ABA. Plant Mol. Biol. 58:699–720 [Google Scholar]
  30. Burns AE, Gleadow RM, Woodrow IE. 30.  2002. Light alters the allocation of nitrogen to cyanogenic glycosides in Eucalyptus cladocalyx. Oecologia 133:288–94 [Google Scholar]
  31. Burns AE, Gleadow RM, Zacarias A, Cuambe CE, Miller RE, Cavagnaro TR. 31.  2012. Variations in the chemical composition of cassava (Manihot esculenta Crantz) leaves and roots as affected by genotypic and environmental variation. J. Agric. Food Chem. 60:4946–56 [Google Scholar]
  32. Busk PK, Møller BL. 32.  2002. Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants. Plant Physiol. 129:1222–31 [Google Scholar]
  33. Cavagnaro TR, Gleadow RM, Miller RE. 33.  2011. Plant nutrient acquisition and utilisation in a high carbon dioxide world. Funct. Plant Biol. 38:87–96 [Google Scholar]
  34. Chassagne D, Crouzet JC, Bayonove CL, Baumes RL. 34.  1996. Identification and quantification of passion fruit cyanogenic glycosides. J. Agric. Food Chem. 443817–20
  35. Cicek M, Esen A. 35.  1998. Structure and expression of a dhurrinase (β-glucosidase) from Sorghum. Plant Physiol. 116:1469–78 [Google Scholar]
  36. Clausen V, Frydenvang K, Koopmann R, Jørgensen LB, Abbiw DK. 36.  et al. 2002. Plant analysis by butterflies: occurrence of cyclopentenylglycines in Passifloraceae, Flacourtiaceae, and Turneraceae and discovery of the novel nonproteinogenic amino acid 2-(3′-cyclopentenyl)glycine in Rinorea. J. Nat. Prod. 65:542–47 [Google Scholar]
  37. Clegg DO, Conn EE, Janzen DH. 37.  1979. Developmental fate of the cyanogenic glycoside linamarin in Costa Rican wild lima bean seeds. Nature 278:343–44 [Google Scholar]
/content/journals/10.1146/annurev-arplant-050213-040027
Loading
/content/journals/10.1146/annurev-arplant-050213-040027
Loading

Data & Media loading...

  • Article Type: Review Article
This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error