Burning vegetation produces cyanohydrins that liberate cyanide and stimulate seed germination

Nature Communications

Volumn 2, Issue 1, 2011, Pages

  Flematti, Gavin R ^a   Merritt, David J ^a,b   Piggott, Matthew J ^a   Trengove, Robert D ^c   Smith, Steven M ^a   Dixon, Kingsley W ^a,b   Ghisalberti, Emilio L ^a  

^a UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

^b KINGS PARK AND BOTANIC GARDEN   (Australia)

^c MURDOCH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; CYANOHYDRIN; GLYCERONITRILE; UNCLASSIFIED DRUG; WATER; HYDROGEN CYANIDE; NITRILE;

ARTICLE; FIRE ECOLOGY; GERMINATION; HYDROLYSIS; NONHUMAN; ORGANIC MATTER PRODUCTION; VEGETATION; ANALYSIS OF VARIANCE; ANGIOSPERM; AUSTRALIA; CHEMICAL STRUCTURE; CHEMISTRY; FIRE; GROWTH, DEVELOPMENT AND AGING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; METABOLISM; PHYSIOLOGY; SMOKE; SPECIES DIFFERENCE;

ANALYSIS OF VARIANCE; ANGIOSPERMS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FIRES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GERMINATION; HYDROGEN CYANIDE; MOLECULAR STRUCTURE; NITRILES; SMOKE; SPECIES SPECIFICITY; WESTERN AUSTRALIA;

EID: 79959552134     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms1356     Document Type: Article

References (47)

1. Pausas, J. G. & Keeley, J. E. A burning story: the role of fire in the history of life. Bioscience 59, 593-601 (2009).
2. Bradshaw, S. D., Dixon, K. W., Hopper, S. D., Lambers, H. & Turner, S. R. Little evidence for fire-adapted plant traits in Mediterranean climate regions. Trends Plant Sci. 16, 69-76 (2011).
3. De Lange, J. H. & Boucher, C. Autecological studies on Audouinia capitata (Bruniaceae). I. Plant-derived smoke as a seed germination cue. S. Afr. J. Bot. 56, 700-703 (1990).
4. Dixon, K. W., Merritt, D. J., Flematti, G. R. & Ghisalberti, E. L. Karrikinolide-a phytoreactive compound derived from smoke with applications in horticulture, ecological restoration and agriculture. Acta Hort. 813, 155-170 (2009).
5. Baldwin, I. T., Staszak-Kozinski, L. & Davidson, R. Up in smoke: I. Smoke-derived germination cues for postfire annual, Nicotiana attenuata Torr. Ex. Watson. J. Chem. Ecol. 20, 2345-2371 (1994). (Pubitemid 2156789)
6. Van Staden, J., Drewes, F. E. & Brown, N. A. C. Some chromatographic characteristics of germination stimulants in plant-derived smoke extracts. Plant Growth Regul. 17, 241-249 (1995). (Pubitemid 3009821)
7. Van Staden, J., Drewes, F. E. & Jäger, A. K. The search for germination stimulants in plant derived smoke extracts. S. Afr. J. Bot. 61, 260-263 (1995).
8. Keeley, J. E. & Fotheringham, C. J. Trace gas emissions and smoke-induced seed germination. Science 276, 1248-1250 (1997).
9. Preston, C. A., Becker, R. & Baldwin, I. T. Is NO news good news? Nitrogen oxides are not components of smoke that elicits germination in two smoke-stimulated species, Nicotiana attenuata and Emmenanthe penduliflora. Seed Sci. Res. 14, 73-79 (2004). (Pubitemid 38536916)
10. Dixon, K. W., Roche, S., Meney, K. & Von Perger, B. Smoke enhanced germination of native species for minesite rehabilitation. Minerals and Energy Research Institute of Western Australia Report, 174 (1996).
11. Flematti, G. R., Ghisalberti, E. L., Dixon, K. W. & Trengove, R. D. A compound from smoke that promotes seed germination. Science 305, 977 (2004). (Pubitemid 39071765)
12. Flematti, G. R., Ghisalberti, E. L., Dixon, K. W. & Trengove, R. D. Identification of alkyl substituted 2H-furo[2,3-c]pyran-2-ones as germination stimulants present in smoke. J. Agric. Food Chem. 57, 9475-9480 (2009).
13. Chiwocha, S. D. S. et al. Karrikins: a new family of plant growth regulators in smoke. Plant Sci. 177, 252-256 (2009).
14. Light, M. E., Daws, M. I. & van Staden, J. Smoke-derived butenolide: towards understanding its biological effects. S. Afr. J. Bot. 75, 1-7 (2009).
15. Nelson, D. C. et al. Karrikins enhance light responses during germination and seedling development in Arabidopsis thaliana. Proc. Natl Acad. Sci. USA 107, 7095-7100 (2010).
16. Tieu, A., Dixon, K. W., Meney, K. A., Sivasithamparam, K. & Barrett, R. L. Spatial and developmental variation in seed dormancy characteristics in the fire-responsive species Anigozanthos manglesii (Haemodoraceae) from Western Australia. Ann. Bot. 88, 19-26 (2001). (Pubitemid 32632384)
17. Hopper, S. D., Smith, R. J., Fay, M. F., Manning, J. C. & Chase, M. W. Molecular phylogenetics of Haemodoraceae in the Greater Cape and Southwest Australian Floristic Regions. Mol. Phylogenet. Evol. 51, 19-30 (2009).
18. Dixon, K. W., Roche, S. & Pate, J. S. The promotive effect of smoke derived from burnt native vegetation on seed germination of Western Australian plants. Oecologia 101, 185-192 (1995).
19. Roche, S., Dixon, K. W. & Pate, J. S. Seed ageing and smoke: partner cues in the amelioration of seed dormancy in selected Australian native species. Aust. J. Bot. 45, 783-815 (1997). (Pubitemid 28118216)
20. Kopecky, J. & Smejkal, J. Simple synthesis of acrylonitrile metabolites; oxiranecarbonitrile and 2,3-dihydroxypropionitrile. Z. Chem. 24, 211-212 (1984).
21. Hubschwerlen, C. A convenient synthesis of L-(S)-glyceraldehyde acetonide from L-ascorbic acid. Synthesis 962-964 (1986).
22. Schmid, C. R. et al. Synthesis of 2,3-O-isopropylidene-D-glyceraldehyde in high chemical and optical purity: observations on the development of a practical bulk process. J. Org. Chem. 56, 4056-4058 (1991).
23. Chelucci, G., Cabras, M. A. & Saba, A. Synthesis of optically active hydroxyalkylpyridines and related pyridyl amines. Tetrahedron: Asymmetry 5, 1973-1978 (1994). (Pubitemid 24323242)
24. Gregory, R. J. H. Cyanohydrins in Nature and the laboratory: biology, preparations, and synthetic applications. Chem. Rev. 99, 3649-3682 (1999). (Pubitemid 129589131)
25. Siegien, I. & Bogatek, R. Cyanide action in plants-from toxic to regulatory. Acta Physiol. Plant. 28, 483-497 (2006). (Pubitemid 44800045)
26. Major, W. & Roberts, E. H. Dormancy in cereal seeds I. The effects of oxygen and respiratory inhibitors. J. Exp. Bot. 19, 77-89 (1968).
27. Hendricks, S. B. & Taylorson, R. B. Promotion of seed germination by nitrates and cyanides. Nature 237, 169-170 (1972).
28. Taylorson, R. B. & Hendricks, S. B. Promotion of seed germination by cyanide. Plant Physiol. 52, 23-27 (1973).
29. Bogatek, R. & Gniazdowska, A. Nitric oxide and HCN reduce deep dormancy of apple seeds. Acta Physiol. Plant. 28, 281-287 (2006).
30. Oracz, K., El-Maarouf-Bouteau, H., Bogatek, R., Corbineau, F. & Bailly, C. Release of sunflower seed dormancy by cyanide: cross-talk with ethylene signalling pathway. J. Exp. Bot. 59, 2241-2251 (2008). (Pubitemid 351824694)
31. Footitt, S. & Cohn, M. A. Developmental arrest: from sea urchins to seeds. Seed Sci. Res. 11, 3-16 (2001). (Pubitemid 32663288)
32. Oracz, K. et al. The mechanisms involved in seed dormancy alleviation by hydrogen cyanide unravel the role of reactive oxygen species as key factors of cellular signalling during germination. Plant Physiol. 150, 494-505 (2009).
33. Bethke, P. C., Libourel, I. G. L., Reinohl, V. & Jones, R. L. Sodium nitroprusside, cyanide, nitrite and nitrate break Arabidopsis seed dormancy in a nitric oxide-dependent manner. Planta 223, 805-812 (2006). (Pubitemid 43853824)
34. Serianni, A. S., Nunez, H. A. & Barker, R. Cyanohydrin synthesis: studies with cyanide. J. Org. Chem. 45, 3329-3341 (1980).
35. Selmar, D., Carvalho, F. J. P. & Conn, E. E. A colorimetric assay for α-hydroxynitrile lyase. Anal. Biochem. 166, 208-211 (1987).
36. Tieu, A., Dixon, K. W., Sivasithamparam, K., Plummer, J. A. & Sieler, I. M. Germination of four species of native Western Australian plants using plant-derived smoke. Aust. J. Bot. 47, 207-219 (1999). (Pubitemid 29337503)
37. Esashi, Y., Isuzugawa, K., Matsuyama, S., Ashino, H. & Hasegawa, R. Endogenous evolution of HCN during pre-germination periods in many seed species. Physiol. Plant. 83, 27-33 (1991).
38. Esashi, Y., Matsuyama, S., Ashino, H., Ogasawara, M. & Hasegawa, R. Glucosidase activities and HCN liberation in unimbibed and imbibed seeds, and the induction of cocklebur seed germination by cyanogenic glycosides. Physiol. Plant. 83, 34-40 (1991).
39. Oracz, K. et al. ROS production and protein oxidation as a novel mechanism for seed dormancy alleviation. Plant J. 50, 452-465 (2007). (Pubitemid 46634487)
40. Yaylayan, V. A., Harty-Majors, S. & Ismail, A. A. Investigation of the mechanism of dissociation of glycolaldehyde dimer (2,5-dihydroxy-1,4- dioxane) by FTIR spectroscopy. Carb. Res. 309, 31-38 (1998). (Pubitemid 28349922)
41. Ricardo, A., Carrigan, M. A., Olcott, A. N. & Benner, S. A. Borate minerals stabilize ribose. Science 303, 196 (2004). (Pubitemid 38057562)
42. Busfield, W. K., Ennis, M. P. & McEwen, I. J. An infrared study of intramolecular hydrogen bonding in diols. Spectrochim. Acta. 29A, 1259-1264 (1973).
43. Stevens, J. C., Merritt, D. J., Flematti, G. R., Ghisalberti, E. L. & Dixon, K. W. Seed germination of agricultural weeds is promoted by the butenolide 3-methyl-2H-furo[2,3-c]pyran-2-one under laboratory and field conditions. Plant Soil 298, 113-124 (2007). (Pubitemid 47404025)
44. Flematti, G. R., Ghisalberti, E. L., Dixon, K. W. & Trengove, R. D. Synthesis of the seed germination stimulant 3-methyl-2H-furo[2,3-c]pyran-2-one. Tetrahedron Lett. 46, 5719-5721 (2005). (Pubitemid 41019175)
45. Clarke, H. T. & Bean, H. J. ?-Aminoisobutyric acid. Org. Synth. Coll. 2, 29-30 (1943).
46. Gerrits, P. J., Zumbragel, F. & Marcus, J. Analyzing the hydrocyanation reaction: chiral HPLC and synthesis of racemic cyanohydrins. Tetrahedron 57, 8691-8698 (2001). (Pubitemid 32947076)
47. Gomori, G. in Methods in Enzymology (eds Colowick, S. P. & Kaplan, N. O.) 138-146 (Academic Press, 1955).