Below is from Science Dec 23 2010 A Compound from Smoke That Promotes Seed Germination Gavin R. Flematti,1* Emilio L. Ghisalberti,1 Kingsley W. Dixon,2,3 Robert D. Trengove4 Smoke derived from burning plant material has been found to increase germination of a wide range of plant species from Australia, North America, and South Africa (1). We now report the identity of a compound, present in plant- and cellulose-derived smoke, that promotes germination of a variety of smoke-responsive taxa at a level similar to that of plant-derived smoke water. The separation of the bioactive agent was facilitated by bioassay-guided fractionation with Lactuca sativa L. cv. Grand Rapids (2) and two smoke-responsive Australian species, Conostylis aculeata R. Br. (Haemodoraceae) and Stylidium affine Sonder. (Stylidiaceae) (3). Extensive fractionation of the relatively less complex, cellulosederived smoke (from combustion of filter paper) resulted in the isolation of a compound that promotes seed germination (4). The structure of this compound was elucidated from mass spectrometry (MS) and spectroscopic data obtained by 1 H, 13C, and two-dimensional (homonuclear correlation, heteronuclear single-quantum coherence, heteronuclear multi-bond correlation, and nuclear Overhausereffectspectroscopy)nuclearmagnetic resonance (NMR) techniques. Confirmation of the structure as the butenolide 3-methyl-2Hfuro[2,3-c]pyran-2-one (1) (Scheme 1) was achieved by synthesis. The presence of1 in extracts of plantderived smoke was confirmed by gas chromatography–MS analysis. We compared the activity of the synthetic form of the butenolide (1) with that of plant-derived smoke water by testing it at a range of concentrations with the three bioassay species. We compared the activity of the synthetic form of the butenolide (1) with that of plant-derived smoke water by testing it at a range of concentrations with the three bioassay species. The results (Fig. 1) show that1 stimulated the germination of each test species to a level similar to that achieved with plant-derived smoke water. Furthermore, activity is demonstrated at very low concentrations (1 ppb, 109 M). Testing of other smoke-responsive Australian species and smoke-responsive South African (e.g., Syncarpha vestita) and North American (e.g., Emmenanthe penduliflora and Nicotiana attenuata) species has further confirmed the activity of1 (table S1). The butenolide (1) conforms to the necessary ecological attributes of smoke that is produced from fires in natural environments. For example, the butenolide (1) is stable at high temperatures (itsmeltingpointis118°to119°C),water-soluble, active at a wide range of concentrations (1 ppm to 100 ppt), and capable of germinating a wide range of fire-following species. The butenolide is derived from the combustion of cellulose, which, as a component of all plants, represents a universal combustion substrate that would be present in natural fires. Given the broad and emerging use of smoke as an ecological and restoration tool (1), the identification of 1 as a main contributor to the germination-promoting activity of smoke could provide benefits for horticulture, agriculture, mining, and disturbedland restoration. In addition, the mode of action and mechanism by which1 stimulates germination can now be investigated. In this context, it is useful to note that the natural product ()strigol, which promotes the germination of the parasitic weed Striga (5), is active at similar concentrations (109 M) and contains a butenolide moiety and additional conjugated functionality similar to those in1. References and Notes 1. N. A. C. Brown, J. Van Staden, Plant Growth Regul.22, 115 (1997). 2. F. E. Drewes, M. T. Smith, J. Van Staden, Plant Growth Regul. 16, 205 (1995). 3. S. Roche, K. W. Dixon, J. S. Pate,Aust.J.Bot.45, 783 (1997). 4. Materials and methods are available as supporting material on Science Online. 5. S. C. M. Wigchert, B. Zwanenburg, J. Agric. Food Chem. 47, 1320 (1999). 6. We thank L. T. Byrne for assistance with the structural elucidation of the active compound, D. Wege and S. K. Brayshaw for assistance with the synthetic approach, S. R. Turner and D. J. Merritt for assistance with germination trials, and Alcoa World Alumina and Iluka Resources for providing seeds of native species for testing. Supporting Online Material http://sciencemag.org/cgi/content/… Materials and Methods Table S1 4 May 2004; accepted 25 June 2004 Published online 8 July 2004; 10.1126/science.1099944 Include this information when citing this paper. 1 School of Biomedical and Chemical Sciences, 2School of Plant Biology, The University of Western Australia, Crawley, WA 6009, Australia. 3Kings Park and Botanic Garden, West Perth, WA 6005, Australia. 4School of Engineering Science, Murdoch University, Rockingham, WA 6168, Australia. *To whom correspondence should be addressed. Email: gflematt@chem.uwa.edu.au Scheme 1. _______________________________________________ pbs mailing list pbs@lists.ibiblio.org http://pacificbulbsociety.org/list.php http://pacificbulbsociety.org/pbswiki/