Production of the seed germination stimulant karrikinolide from combustion of simple carbohydrates

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 4, 2011, Pages 1195-1198

  Flematti, Gavin R ^a   Scaffidi, Adrian ^a   Dixon, Kingsley W ^a,b   Smith, Steven M ^a   Ghisalberti, Emilio L ^a  

^a UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

^b KINGS PARK AND BOTANIC GARDEN   (Australia)

Author keywords

combustion; germination stimulant; karrikin; Karrikinolide; smoke; xylose

Indexed keywords

CONCENTRATION RANGES; D-GLUCOSE; GERMINATION STIMULANT; INHIBITORY EFFECT; KARRIKIN; KARRIKINOLIDE; NATURALLY OCCURRING; PLANT MATERIAL; SEED GERMINATION STIMULANTS;

AMINO ACIDS; CARBOHYDRATES; GLUCOSE; SMOKE;

COMBUSTION;

CARBOHYDRATE; CARBON; CELLULOSE; FURAN DERIVATIVE; GLUCOSE; GLYCINE; KARRIKINOLIDE; PYRAN DERIVATIVE; WATER; XYLOSE;

ARTICLE; CHEMISTRY; GERMINATION; HEAT; SMOKE; SOLUTION AND SOLUBILITY; SYNTHESIS;

CARBOHYDRATES; CARBON ISOTOPES; CELLULOSE; FURANS; GERMINATION; GLUCOSE; GLYCINE; HOT TEMPERATURE; PYRANS; SMOKE; SOLUTIONS; WATER; XYLOSE;

EID: 79951738568     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf1041728     Document Type: Article

References (20)

1. 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. 1994, 20, 2345-2371 (Pubitemid 2156789)
2. 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 1995, 101, 185-192
3. Brown, N. A. C.; van Staden, J. Smoke as a germination cue: a review Plant Growth Regul. 1997, 22, 115-124 (Pubitemid 27378239)
4. Minorsky, P. V. The hot and the classic Plant Physiol. 2002, 128, 1167-1168
5. Light, M. E.; van Staden, J. The potential of smoke in seed technology S. Afr. J. Bot. 2004, 70, 97-101 (Pubitemid 38831315)
6. Light, M. E.; Daws, M. I.; van Staden, J. Smoke-derived butenolide: towards understanding its biological effects S. Afr. J. Bot. 2009, 75, 1-7
7. 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 Hortic. 2009, 813, 155-170
8. Chiwocha, S. D. S.; Dixon, K. W.; Flematti, G. R.; Ghisalberti, E. L.; Merritt, D. J.; Nelson, D. C.; Riseborough, J. M.; Smith, S. M.; Stevens, J. C. Karrikins: A new family of plant growth regulators in smoke Plant Sci. 2009, 177, 252-256
9. 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. 1990, 56, 700-703
10. Flematti, G. R.; Ghisalberti, E. L.; Dixon, K. W.; Trengove, R. D. A compound from smoke that promotes seed germination Science 2004, 305, 977 (Pubitemid 39071765)
11. Flematti, G. R.; Ghisalberti, E. L.; Dixon, K. W.; Trengove, R. D. Identification of alkyl substituted 2 H -furo[2,3- c ]pyran-2-ones as germination stimulants present in smoke J. Agric. Food Chem. 2009, 57, 9475-9480
12. 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. 2004, 14, 73-79 (Pubitemid 38536916)
13. Light, M. E.; Burger, B. V.; Van Staden, J. Formation of a seed germination promoter from carbohydrates and amino acids J. Agric. Food Chem. 2005, 53, 5936-5942 (Pubitemid 41126628)
14. Flematti, G. R.; Ghisalberti, E. L.; Dixon, K. W.; Trengove, R. D. Synthesis of the seed germination stimulant 3-methyl-2 H -furo[2,3- c ]pyran-2-one Tetrahedron Lett. 2005, 46, 5719-5721 (Pubitemid 41019175)
15. Scaffidi, A.; Flematti, G. R.; Nelson, D. C.; Dixon, K., W.; Smith, S. M.; Ghisalberti, E. L. The synthesis and biological evaluation of labelled karrikinolides for the elucidation of the mode of action of the seed germination stimulant Tetrahedron 2011, 67, 152-157
16. Flematti, G. R.; Goddard-Borger, E. D.; Merritt, D. J.; Ghisalberti, E. L.; Dixon, K. W.; Trengove, R. D. Preparation of 2 H -furo[2,3- c ]pyran-2-one derivatives and evaluation of their germination-promoting activity J. Agric. Food Chem. 2007, 55, 2189-2194 (Pubitemid 46556204)
17. Jäger, A. K.; Light, M. E.; van Staden, J. Effects of source of plant material and temperature on the production of smoke extracts that promote germination of light-sensitive lettuce seeds Environ. Exp. Bot. 1996, 36, 421-429 (Pubitemid 27153310)
18. Flematti, G. R.; Ghisalberti, E. L.; Dixon, K. W.; Trengove, R. D., Germination stimulant in smoke: isolation and identification. In Bioactive Natural Products: Detection, Isolation and Structural Elucidation, 2 nd ed.; Colegate, S. M.; Molyneux, R. J., Eds.; CRC Press: Boca Raton, FL, 2008; pp 531 - 554.
19. Keeley, S. C.; Pizzorno, M. Charred wood stimulated germination of two fire-following herbs of the California chaparral and the role of hemicellulose Amer. J. Bot. 1986, 73, 1289-1297
20. Light, M. E.; Burger, B. V.; Staerk, D.; Kohout, L.; van Staden, J. Butenolides from plant-derived smoke: natural plant growth regulators with antagonistic actions on seed germination J. Nat. Prod. 2010, 73, 267-269