Dixon KW

References (19)

Title : What are karrikins and how were they 'discovered' by plants? - Flematti_2015_BMC.Biol_13_108
Author(s) : Flematti GR , Dixon KW , Smith SM
Ref : BMC Biol , 13 :108 , 2015
Abstract : Karrikins are a family of compounds produced by wildfires that can stimulate the germination of dormant seeds of plants from numerous families. Seed plants could have 'discovered' karrikins during fire-prone times in the Cretaceous period when flowering plants were evolving rapidly. Recent research suggests that karrikins mimic an unidentified endogenous compound that has roles in seed germination and early plant development. The endogenous signalling compound is presumably not only similar to karrikins, but also to the related strigolactone hormones.
ESTHER : Flematti_2015_BMC.Biol_13_108
PubMedSearch : Flematti_2015_BMC.Biol_13_108
PubMedID: 26689715

Title : Strigolactone Hormones and Their Stereoisomers Signal through Two Related Receptor Proteins to Induce Different Physiological Responses in Arabidopsis - Scaffidi_2014_Plant.Physiol_165_1221
Author(s) : Scaffidi A , Waters MT , Sun YK , Skelton BW , Dixon KW , Ghisalberti EL , Flematti GR , Smith SM
Ref : Plant Physiol , 165 :1221 , 2014
Abstract : Two alpha/beta-fold hydrolases, KARRIKIN INSENSITIVE2 (KAI2) and Arabidopsis thaliana DWARF14 (AtD14), are necessary for responses to karrikins (KARs) and strigolactones (SLs) in Arabidopsis (Arabidopsis thaliana). Although KAI2 mediates responses to KARs and some SL analogs, AtD14 mediates SL but not KAR responses. To further determine the specificity of these proteins, we assessed the ability of naturally occurring deoxystrigolactones to inhibit Arabidopsis hypocotyl elongation, regulate seedling gene expression, suppress outgrowth of secondary inflorescences, and promote seed germination. Neither 5-deoxystrigol nor 4-deoxyorobanchol was active in KAI2-dependent seed germination or hypocotyl elongation, but both were active in AtD14-dependent hypocotyl elongation and secondary shoot growth. However, the nonnatural enantiomer of 5-deoxystrigol was active through KAI2 in growth and gene expression assays. We found that the four stereoisomers of the SL analog GR24 had similar activities to their deoxystrigolactone counterparts. The results suggest that AtD14 and KAI2 exhibit selectivity to the butenolide D ring in the 2'R and 2'S configurations, respectively. However, we found, for nitrile-debranone (CN-debranone, a simple SL analog), that the 2'R configuration is inactive but that the 2'S configuration is active through both AtD14 and KAI2. Our results support the conclusion that KAI2-dependent signaling does not respond to canonical SLs. Furthermore, racemic mixtures of chemically synthesized SLs and their analogs, such as GR24, should be used with caution because they can activate responses that are not specific to naturally occurring SLs. In contrast, the use of specific stereoisomers might provide valuable information about the specific perception systems operating in different plant tissues, parasitic weed seeds, and arbuscular mycorrhizae.
ESTHER : Scaffidi_2014_Plant.Physiol_165_1221
PubMedSearch : Scaffidi_2014_Plant.Physiol_165_1221
PubMedID: 24808100

Title : Karrikin and cyanohydrin smoke signals provide clues to new endogenous plant signaling compounds - Flematti_2013_Mol.Plant_6_29
Author(s) : Flematti GR , Waters MT , Scaffidi A , Merritt DJ , Ghisalberti EL , Dixon KW , Smith SM
Ref : Mol Plant , 6 :29 , 2013
Abstract : Two new types of signaling compounds have been discovered in wildfire smoke due to their ability to stimulate seed germination. The first discovered were karrikins, which share some structural similarity with the strigolactone class of plant hormones, and both signal through a common F-box protein. However, karrikins and strigolactones operate through otherwise distinct signaling pathways, each distinguished by a specific alpha/beta hydrolase protein. Genetic analysis suggests that plants contain endogenous compounds that signal specifically through the karrikin pathway. The other active compounds discovered in smoke are cyanohydrins that release germination-stimulating cyanide upon hydrolysis. Cyanohydrins occur widely in plants and have a role in defense against other organisms, but an additional role in endogenous cyanide signaling should also now be considered.
ESTHER : Flematti_2013_Mol.Plant_6_29
PubMedSearch : Flematti_2013_Mol.Plant_6_29
PubMedID: 23180672

Title : Carlactone-independent seedling morphogenesis in Arabidopsis - Scaffidi_2013_Plant.J_76_1
Author(s) : Scaffidi A , Waters MT , Ghisalberti EL , Dixon KW , Flematti GR , Smith SM
Ref : Plant J , 76 :1 , 2013
Abstract : Strigolactone hormones are derived from carotenoids via carlactone, and act through the alpha/beta-hydrolase D14 and the F-box protein D3/MAX2 to repress plant shoot branching. While MAX2 is also necessary for normal seedling development, D14 and the known strigolactone biosynthesis genes are not, raising the question of whether endogenous, canonical strigolactones derived from carlactone have a role in seedling morphogenesis. Here, we report the chemical synthesis of the strigolactone precursor carlactone, and show that it represses Arabidopsis shoot branching and influences leaf morphogenesis via a mechanism that is dependent on the cytochrome P450 MAX1. In contrast, both physiologically active Z-carlactone and the non-physiological E isomer exhibit similar weak activity in seedlings, and predominantly signal through D14 rather than its paralogue KAI2, in a MAX2-dependent but MAX1-independent manner. KAI2 is essential for seedling morphogenesis, and hence this early-stage development employs carlactone-independent morphogens for which karrikins from wildfire smoke are specific surrogates. While the commonly employed synthetic strigolactone GR24 acts non-specifically through both D14 and KAI2, carlactone is a specific effector of strigolactone signalling that acts through MAX1 and D14.
ESTHER : Scaffidi_2013_Plant.J_76_1
PubMedSearch : Scaffidi_2013_Plant.J_76_1
PubMedID: 23773129

Title : Regulation of seed germination and seedling growth by chemical signals from burning vegetation - Nelson_2012_Annu.Rev.Plant.Biol_63_107
Author(s) : Nelson DC , Flematti GR , Ghisalberti EL , Dixon KW , Smith SM
Ref : Annu Rev Plant Biol , 63 :107 , 2012
Abstract : It is well known that burning of vegetation stimulates new plant growth and landscape regeneration. The discovery that char and smoke from such fires promote seed germination in many species indicates the presence of chemical stimulants. Nitrogen oxides stimulate seed germination, but their importance in post-fire germination has been questioned. Cyanohydrins have been recently identified in aqueous smoke solutions and shown to stimulate germination of some species through the slow release of cyanide. However, the most information is available for karrikins, a family of butenolides related to 3-methyl-2H-furo[2,3-c]pyran-2-one. Karrikins stimulate seed germination and influence seedling growth. They are active in species not normally associated with fire, and in Arabidopsis they require the F-box protein MAX2, which also controls responses to strigolactone hormones. We hypothesize that chemical similarity between karrikins and strigolactones provided the opportunity for plants to employ a common signal transduction pathway to respond to both types of compound, while tailoring specific developmental responses to these distinct environmental signals.
ESTHER : Nelson_2012_Annu.Rev.Plant.Biol_63_107
PubMedSearch : Nelson_2012_Annu.Rev.Plant.Biol_63_107
PubMedID: 22404467

Title : Exploring the molecular mechanism of karrikins and strigolactones - Scaffidi_2012_Bioorg.Med.Chem.Lett_22_3743
Author(s) : Scaffidi A , Waters MT , Bond CS , Dixon KW , Smith SM , Ghisalberti EL , Flematti GR
Ref : Bioorganic & Medicinal Chemistry Lett , 22 :3743 , 2012
Abstract : Karrikins and strigolactones are novel plant growth regulators that contain similar molecular features, but very little is known about how they elicit responses in plants. A tentative molecular mechanism has previously been proposed involving a Michael-type addition for both compounds. Through structure-activity studies with karrikins, we now propose an alternative mechanism for karrikin and strigolactone mode of action that involves hydrolysis of the butenolide ring.
ESTHER : Scaffidi_2012_Bioorg.Med.Chem.Lett_22_3743
PubMedSearch : Scaffidi_2012_Bioorg.Med.Chem.Lett_22_3743
PubMedID: 22542018

Title : Solar irradiation of the seed germination stimulant karrikinolide produces two novel head-to-head cage dimers - Scaffidi_2012_Org.Biomol.Chem_10_4069
Author(s) : Scaffidi A , Waters MT , Skelton BW , Bond CS , Sobolev AN , Bythell-Douglas R , McKinley AJ , Dixon KW , Ghisalberti EL , Smith SM , Flematti GR
Ref : Org Biomol Chem , 10 :4069 , 2012
Abstract : Karrikinolide is a naturally derived potent seed germination stimulant that is responsible for triggering the germination of numerous plant species from various habitats around the world. We now report that solar irradiation of karrikinolide yields two novel head-to-head cage photodimers with the formation, stability and bioactivity of both presented herein.
ESTHER : Scaffidi_2012_Org.Biomol.Chem_10_4069
PubMedSearch : Scaffidi_2012_Org.Biomol.Chem_10_4069
PubMedID: 22514031

Title : Specialisation within the DWARF14 protein family confers distinct responses to karrikins and strigolactones in Arabidopsis. - Waters_2012_Development_139_1285
Author(s) : Waters MT , Nelson DC , Scaffidi A , Flematti GR , Sun YK , Dixon KW , Smith SM
Ref : Development , 139 :1285 , 2012
Abstract : Karrikins are butenolides derived from burnt vegetation that stimulate seed germination and enhance seedling responses to light. Strigolactones are endogenous butenolide hormones that regulate shoot and root architecture, and stimulate the branching of arbuscular mycorrhizal fungi. Thus, karrikins and strigolactones are structurally similar but physiologically distinct plant growth regulators. In Arabidopsis thaliana, responses to both classes of butenolides require the F-box protein MAX2, but it remains unclear how discrete responses to karrikins and strigolactones are achieved. In rice, the DWARF14 protein is required for strigolactone-dependent inhibition of shoot branching. Here, we show that the Arabidopsis DWARF14 orthologue, AtD14, is also necessary for normal strigolactone responses in seedlings and adult plants. However, the AtD14 paralogue KARRIKIN INSENSITIVE 2 (KAI2) is specifically required for responses to karrikins, and not to strigolactones. Phylogenetic analysis indicates that KAI2 is ancestral and that AtD14 functional specialisation has evolved subsequently. Atd14 and kai2 mutants exhibit distinct subsets of max2 phenotypes, and expression patterns of AtD14 and KAI2 are consistent with the capacity to respond to either strigolactones or karrikins at different stages of plant development. We propose that AtD14 and KAI2 define a class of proteins that permit the separate regulation of karrikin and strigolactone signalling by MAX2. Our results support the existence of an endogenous, butenolide-based signalling mechanism that is distinct from the strigolactone pathway, providing a molecular basis for the adaptive response of plants to smoke.
ESTHER : Waters_2012_Development_139_1285
PubMedSearch : Waters_2012_Development_139_1285
PubMedID: 22357928
Gene_locus related to this paper: arath-AtD14 , arath-KAI2.D14L , orysj-q10j20 , orysj-Q10QA5

Title : F-box protein MAX2 has dual roles in karrikin and strigolactone signaling in Arabidopsis thaliana - Nelson_2011_Proc.Natl.Acad.Sci.U.S.A_108_8897
Author(s) : Nelson DC , Scaffidi A , Dun EA , Waters MT , Flematti GR , Dixon KW , Beveridge CA , Ghisalberti EL , Smith SM
Ref : Proc Natl Acad Sci U S A , 108 :8897 , 2011
Abstract : Smoke is an important abiotic cue for plant regeneration in postfire landscapes. Karrikins are a class of compounds discovered in smoke that promote seed germination and influence early development of many plants by an unknown mechanism. A genetic screen for karrikin-insensitive mutants in Arabidopsis thaliana revealed that karrikin signaling requires the F-box protein MAX2, which also mediates responses to the structurally-related strigolactone family of phytohormones. Karrikins and the synthetic strigolactone GR24 trigger similar effects on seed germination, seedling photomorphogenesis, and expression of a small set of genes during these developmental stages. Karrikins also repress MAX4 and IAA1 transcripts, which show negative feedback regulation by strigolactone. We demonstrate that all of these common responses are abolished in max2 mutants. Unlike strigolactones, however, karrikins do not inhibit shoot branching in Arabidopsis or pea, indicating that plants can distinguish between these signals. These results suggest that a MAX2-dependent signal transduction mechanism was adapted to mediate responses to two chemical cues with distinct roles in plant ecology and development.
ESTHER : Nelson_2011_Proc.Natl.Acad.Sci.U.S.A_108_8897
PubMedSearch : Nelson_2011_Proc.Natl.Acad.Sci.U.S.A_108_8897
PubMedID: 21555559

Title : Burning vegetation produces cyanohydrins that liberate cyanide and stimulate seed germination - Flematti_2011_Nat.Commun_2_360
Author(s) : Flematti GR , Merritt DJ , Piggott MJ , Trengove RD , Smith SM , Dixon KW , Ghisalberti EL
Ref : Nat Commun , 2 :360 , 2011
Abstract : Cyanide is well known for its toxicity towards living organisms. Many plants use cyanide as a defensive agent against herbivores, releasing it through the enzymatic hydrolysis of endogenous cyanogenic compounds. At low concentrations, cyanide has been proposed to have a regulatory role in many plant processes including stimulation of seed germination. However, no ecological role for cyanide in seed germination has been established. In the present study, we show that burning plant material produces the cyanohydrin, glyceronitrile. We also show that, in the presence of water, glyceronitrile is slowly hydrolysed to release cyanide that stimulates seed germination of a diverse range of fire-responsive species from different continents. We propose that glyceronitrile serves as an ecological store for cyanide and is an important cue for stimulating seed germination and landscape regeneration after fires.
ESTHER : Flematti_2011_Nat.Commun_2_360
PubMedSearch : Flematti_2011_Nat.Commun_2_360
PubMedID: 21694708

Title : Production of the seed germination stimulant karrikinolide from combustion of simple carbohydrates - Flematti_2011_J.Agric.Food.Chem_59_1195
Author(s) : Flematti GR , Scaffidi A , Dixon KW , Smith SM , Ghisalberti EL
Ref : Journal of Agricultural and Food Chemistry , 59 :1195 , 2011
Abstract : The naturally occurring seed germination stimulant karrikinolide is formed from the combustion of plant material including cellulose. It has previously been reported that combustion of simple carbohydrates such as d-glucose does not produce extracts containing karrikinolide. Moreover, it was reported that extracts with germination-promoting ability could be obtained only by combustion of simple carbohydrates in the presence of amino acids such as l-glycine. By employing a (13)C-labeled karrikinolide to physically quantify natural karrikinolide, we now show that it is produced from combustion of simple carbohydrates in similar amounts regardless of whether l-glycine is present or not. The addition of l-glycine appears to be beneficial in reducing the inhibitory effect of smoke extracts and provides a greater concentration range for effective germination-promoting activity.
ESTHER : Flematti_2011_J.Agric.Food.Chem_59_1195
PubMedSearch : Flematti_2011_J.Agric.Food.Chem_59_1195
PubMedID: 21280622

Title : Karrikins enhance light responses during germination and seedling development in Arabidopsis thaliana - Nelson_2010_Proc.Natl.Acad.Sci.U.S.A_107_7095
Author(s) : Nelson DC , Flematti GR , Riseborough JA , Ghisalberti EL , Dixon KW , Smith SM
Ref : Proc Natl Acad Sci U S A , 107 :7095 , 2010
Abstract : Karrikins are a class of seed germination stimulants identified in smoke from wildfires. Microarray analysis of imbibed Arabidopsis thaliana seeds was performed to identify transcriptional responses to KAR(1) before germination. A small set of genes that are regulated by KAR(1), even when germination is prevented by the absence of gibberellin biosynthesis or light, were identified. Light-induced genes, putative HY5-binding targets, and ABRE-like promoter motifs were overrepresented among KAR(1)-up-regulated genes. KAR(1) transiently induced the light signal transduction transcription factor genes HY5 and HYH. Germination of afterripened Arabidopsis seed was triggered at lower fluences of red light when treated with KAR(1). Light-dependent cotyledon expansion and inhibition of hypocotyl elongation were enhanced in the presence of germination-active karrikins. HY5 is important for the Arabidopsis hypocotyl elongation, but not seed germination, response to karrikins. These results reveal a role for karrikins in priming light responses in the emerging seedling, and suggest that the influence of karrikins on postfire ecology may not be limited to germination recruitment.
ESTHER : Nelson_2010_Proc.Natl.Acad.Sci.U.S.A_107_7095
PubMedSearch : Nelson_2010_Proc.Natl.Acad.Sci.U.S.A_107_7095
PubMedID: 20351290

Title : Structure-activity relationship of karrikin germination stimulants - Flematti_2010_J.Agric.Food.Chem_58_8612
Author(s) : Flematti GR , Scaffidi A , Goddard-Borger ED , Heath CH , Nelson DC , Commander LE , Stick RV , Dixon KW , Smith SM , Ghisalberti EL
Ref : Journal of Agricultural and Food Chemistry , 58 :8612 , 2010
Abstract : Karrikins (2H-furo[2,3-c]pyran-2-ones) are potent smoke-derived germination promoters for a diverse range of plant species but, to date, their mode of action remains unknown. This paper reports the structure-activity relationship of numerous karrikin analogues to increase understanding of the key structural features of the molecule that are required for biological activity. The results demonstrate that modification at the C5 position is preferred over modification at the C3, C4, or C7 positions for retaining the highest bioactivity.
ESTHER : Flematti_2010_J.Agric.Food.Chem_58_8612
PubMedSearch : Flematti_2010_J.Agric.Food.Chem_58_8612
PubMedID: 20617827

Title : Prior hydration of Brassica tournefortii seeds reduces the stimulatory effect of karrikinolide on germination and increases seed sensitivity to abscisic acid - Long_2010_Ann.Bot_105_1063
Author(s) : Long RL , Williams K , Griffiths EM , Flematti GR , Merritt DJ , Stevens JC , Turner SR , Powles SB , Dixon KW
Ref : Ann Bot , 105 :1063 , 2010
Abstract : BACKGROUND AND AIMS: The smoke-derived compound karrikinolide (KAR(1)) shows significant potential as a trigger for the synchronous germination of seeds in a variety of plant-management contexts, from weed seeds in paddocks, to native seeds when restoring degraded lands. Understanding how KAR(1) interacts with seed physiology is a necessary precursor to the development of the compound as an efficient and effective management tool. This study tested the ability of KAR(1) to stimulate germination of seeds of the global agronomic weed Brassica tournefortii, at different hydration states, to gain insight into how the timing of KAR(1) applications in the field should be managed relative to rain events. METHODS: Seeds of B. tournefortii were brought to five different hydration states [equilibrated at 15 % relative humidity (RH), 47 % RH, 96 % RH, fully imbibed, or re-dried to 15 % RH following maximum imbibition] then exposed to 1 nm or 1 microm KAR(1) for one of five durations (3 min, 1 h, 24 h, 14 d or no exposure). KEY RESULTS: Dry seeds with no history of imbibition were the most sensitive to KAR(1); sensitivity was lower in seeds that were fully imbibed or fully imbibed then re-dried. In addition, reduced sensitivity to KAR(1) was associated with an increased sensitivity to exogenously applied abscisic acid (ABA). CONCLUSIONS: Seed water content and history of imbibition were found to significantly influence whether seeds germinate in response to KAR(1). To optimize the germination response of seeds, KAR(1) should be applied to dry seeds, when sensitivity to ABA is minimized.
ESTHER : Long_2010_Ann.Bot_105_1063
PubMedSearch : Long_2010_Ann.Bot_105_1063
PubMedID: 20348089

Title : Identification of alkyl substituted 2H-furo[2,3-c]pyran-2-ones as germination stimulants present in smoke - Flematti_2009_J.Agric.Food.Chem_57_9475
Author(s) : Flematti GR , Ghisalberti EL , Dixon KW , Trengove RD
Ref : Journal of Agricultural and Food Chemistry , 57 :9475 , 2009
Abstract : The butenolide, 3-methyl-2H-furo[2,3-c]pyran-2-one (1), is a major compound in smoke responsible for promoting the seed germination of a wide range of plant species. We now report the structure of five alkyl substituted variants of 1 that are also present in smoke. The concentrations of these analogues, as well as that of 1, in a typical smoke-water solution have been determined using high-performance liquid chromatography (HPLC) purification followed by gas chromatography-mass spectrometry (GC-MS) analysis. The analogue, 3,5-dimethyl-2H-furo[2,3-c]pyran-2-one (3), was identified at levels that indicate that it is a contributor to the overall germination-promoting activity of crude smoke extracts.
ESTHER : Flematti_2009_J.Agric.Food.Chem_57_9475
PubMedSearch : Flematti_2009_J.Agric.Food.Chem_57_9475
PubMedID: 19785418

Title : Karrikins: A New Family of Plant Growth Regulators in Smoke - Chiwocha_2009_Plant.Sci_177_252
Author(s) : Chiwocha SDS , Dixon KW , Flematti GR , Ghisalberti EL , Merritt DJ , Nelson DC , Riseborough JAM , Smith SM , Stevens JC
Ref : Plant Sci , 177 :252 , 2009
Abstract : Karrikins are a chemically defined family of plant growth regulators discovered in smoke from burning plant material. Karrikins are potent in breaking dormancy of seeds of many species adapted to environments that regularly experience fire and smoke. The recent discovery that karrikins trigger seed germination and control seedling growth in taxa that would rarely experience fire indicates that their significance could extend far beyond fire ecology. This is exemplified by new studies showing that seeds of Arabidopsis thaliana respond sensitively and specifically to karrikins in smoke. These exciting discoveries might be explained if karrikins are produced in the environment by processes other than fire, such as by chemical or microbial degradation of vegetation in response to disturbance of the soil or removal of the plant canopy. Another hypothesis is that plants contain endogenous karrikins that function naturally in the control of seed germination and that species from fire-prone habitats have evolved to respond also to exogenous karrikins. A variant on this hypothesis is that karrikins mimic endogenous plant hormones such as terpenoids that control seed germination. The evidence for these hypotheses is discussed, but whatever the explanation karrikins are now firmly established as an important family of naturally occurring plant growth regulators.
ESTHER : Chiwocha_2009_Plant.Sci_177_252
PubMedSearch : Chiwocha_2009_Plant.Sci_177_252

Title : Karrikins discovered in smoke trigger Arabidopsis seed germination by a mechanism requiring gibberellic acid synthesis and light - Nelson_2009_Plant.Physiol_149_863
Author(s) : Nelson DC , Riseborough JA , Flematti GR , Stevens J , Ghisalberti EL , Dixon KW , Smith SM
Ref : Plant Physiol , 149 :863 , 2009
Abstract : Discovery of the primary seed germination stimulant in smoke, 3-methyl-2H-furo[2,3-c]pyran-2-one (KAR1), has resulted in identification of a family of structurally related plant growth regulators, karrikins. KAR1 acts as a key germination trigger for many species from fire-prone, Mediterranean climates, but a molecular mechanism for this response remains unknown. We demonstrate that Arabidopsis (Arabidopsis thaliana), an ephemeral of the temperate northern hemisphere that has never, to our knowledge, been reported to be responsive to fire or smoke, rapidly and sensitively perceives karrikins. Thus, these signaling molecules may have greater significance among angiosperms than previously realized. Karrikins can trigger germination of primary dormant Arabidopsis seeds far more effectively than known phytohormones or the structurally related strigolactone GR-24. Natural variation and depth of seed dormancy affect the degree of KAR1 stimulation. Analysis of phytohormone mutant germination reveals suppression of KAR1 responses by abscisic acid and a requirement for gibberellin (GA) synthesis. The reduced germination of sleepy1 mutants is partially recovered by KAR1, which suggests that germination enhancement by karrikin is only partly DELLA dependent. While KAR1 has little effect on sensitivity to exogenous GA, it enhances expression of the GA biosynthetic genes GA3ox1 and GA3ox2 during seed imbibition. Neither abscisic acid nor GA levels in seed are appreciably affected by KAR1 treatment prior to radicle emergence, despite marked differences in germination outcome. KAR1 stimulation of Arabidopsis germination is light-dependent and reversible by far-red exposure, although limited induction of GA3ox1 still occurs in the dark. The observed requirements for light and GA biosynthesis provide the first insights into the karrikin mode of action.
ESTHER : Nelson_2009_Plant.Physiol_149_863
PubMedSearch : Nelson_2009_Plant.Physiol_149_863
PubMedID: 19074625

Title : Preparation of 2H-furo[2,3-c]pyran-2-one derivatives and evaluation of their germination-promoting activity - Flematti_2007_J.Agric.Food.Chem_55_2189
Author(s) : Flematti GR , Goddard-Borger ED , Merritt DJ , Ghisalberti EL , Dixon KW , Trengove RD
Ref : Journal of Agricultural and Food Chemistry , 55 :2189 , 2007
Abstract : The butenolide, 3-methyl-2H-furo[2,3-c]pyran-2-one (1), has recently been identified as the germination stimulant present in smoke that promotes the germination of seeds from a wide range of plant species. In this paper, we describe the preparation of a number of analogues of 1 and compare their efficacy in promoting seed germination of three highly smoke-responsive plant species, Lactuca sativa L. cv. Grand Rapids (Asteraceae), Emmenanthe penduliflora Benth. (Hydrophyllaceae), and Solanum orbiculatum Poir. (Solanaceae). The results show that the methyl substituent at C-3 in 1 is important for germination-promoting activity while substitution at C-7 reduces activity. In contrast, bioactivity is mostly retained with analogues substituted at C-4 or C-5.
ESTHER : Flematti_2007_J.Agric.Food.Chem_55_2189
PubMedSearch : Flematti_2007_J.Agric.Food.Chem_55_2189
PubMedID: 17316021

Title : A compound from smoke that promotes seed germination - Flematti_2004_Science_305_977
Author(s) : Flematti GR , Ghisalberti EL , Dixon KW , Trengove RD
Ref : Science , 305 :977 , 2004
Abstract : Exposure of seeds to aerosol smoke or crude smoke extracts stimulates the germination of a number of fire-dependent and fire-independent plant species. We now report the identity of a germination-promoting compound present in plant- and cellulose-derived smoke. The structure of this compound, deduced from spectroscopic analysis and confirmed by synthesis, was shown to be that of the butenolide 3-methyl-2H-furo[2,3-c]pyran-2-one (1). Here we show that 1 promotes germination of a number of plant species at a level similar to that observed with plant-derived smoke water.
ESTHER : Flematti_2004_Science_305_977
PubMedSearch : Flematti_2004_Science_305_977
PubMedID: 15247439