857054-03-6Relevant academic research and scientific papers
From Biomass to the Karrikins via Selective Catalytic Oxidation of Hemicellulose-Derived Butyl Xylosides and Glucosides
Slawin, Alexandra M. Z.,Su, Gerard,Westwood, Nicholas,Xiao, Ganyuan
, (2022/02/17)
Members of the karrikin family of bioactive small molecules are known to promote germination of a range of plants following large scale fires. As a result, they are relevant and interesting compounds. This report describes their synthesis from a biomass-derived product stream. During work to fractionate biomass with the goal of obtaining high quality lignins, an interesting co-product stream derived from the hemicellulose in the biomass, was obtained. Whilst many applications of this co-product stream can be proposed, in this case the major monosaccharides have been converted to relevant karrikins in short reaction sequences. Key results include a highly selective catalytic oxidation reaction, conversion of the resulting ketone to a butenolide by two alternative approaches, a selective acetal reductive opening reaction, X-ray crystallographic analysis of two compounds and detailed comparison of the final products with previous literature reports. Only through successful use of all the components generated during biomass refining, can economic sustainability be potentially achieved.
Discovery of cytochrome bc1 complex inhibitors inspired by the natural product karrikinolide
Chen, Cheng,Wu, Qiong-You,Shan, Lian-Ying,Zhang, Bei,Verpoort, Francis,Yang, Guang-Fu
, p. 97580 - 97586 (2016/10/31)
The cytochrome bc1 complex (cyt bc1 or complex III) is a promising target of numerous antibiotics and fungicides. With an aim to indentify new lead structures for the bc1 complex, a series of novel inhibitors were discovered from the natural product karrikinolide for the first time. Extensive screening results suggested variable inhibitory activities of these compounds against succinate-cytochrome reductase [SCR, a mixture of respiratory complex II (SQR) and complex III (the bc1 complex)], implying the essential role of a 4-substituted phenyl group for the high potency. Exceptionally, compound 12g showed excellent inhibition potency having an IC50 value in the sub-micromolar range, demonstrating its higher potency than the commercial control amisulbrom by over two orders of magnitude. Further experiments inferred that these newly prepared compounds mainly target the bc1 complex. Seemingly, this work has presented a new lead scaffold for further development of bc1 complex inhibitors.
Karrikins from plant smoke modulate bacterial quorum sensing
Mandabi, Aviad,Ganin, Hadas,Krief, Pnina,Rayo, Josep,Meijler, Michael M.
supporting information, p. 5322 - 5325 (2014/05/06)
The discovery that plant smoke contains germination stimuli has led to the identification of a new class of signaling molecules named karrikins. Here we report a potential second role for these molecules: in various bacterial species-A. tumefaciens, P. aeruginosa and V. harveyi-they modulate bacterial quorum-sensing (QS), with very different outcomes. the Partner Organisations 2014.
Synthesis of butenolides as seed germination stimulants
Sun, Kingmo,Chen, Yuzhong,Wagerle, Ty,Linnstaedt, David,Currie, Martin,Chmura, Preston,Song, Ying,Xu, Ming
, p. 2922 - 2925 (2008/09/21)
Syntheses of a series of novel butenolides as seed germination stimulants are described. The key steps include the cyclization reaction of enamine 4 to form a pyran ring, the efficient halogenating reaction and the selective lithiation reaction of butenolides.
Synthesis of the germination stimulant 3-methyl-2H-furo[2,3-c]pyran-2-one and analogous compounds from carbohydrates
Goddard-Borger, Ethan D.,Ghisalberti, Emilio L.,Stick, Robert V.
, p. 3925 - 3934 (2008/02/13)
An efficacious synthetic route to the recently identified, potent germination stimulant 3-methyl-2H-furo[2,3-c]pyran-2-one and analogous compounds, using carbohydrate substrates, is described. D-Xylose and D-glucuronic acid γ-lactone were used in the preparation of the parent heterocycle and its 5-methoxycarbonyl analogue, respectively. These compounds were elaborated using various methods to furnish the natural product and a suite of its analogues. The germination stimulant was thus prepared on a multi-gram scale in nine steps from inexpensive, commercially available 1,2-O-isopropylidene-D-xylofuranose in an overall yield of 30 %, vastly improving upon the only method published to date. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Preparation of 2H-furo[2,3-c]pyran-2-one derivatives and evaluation of their germination-promoting activity
Flematti, Gavin R.,Goddard-Borger, Ethan D.,Merritt, David J.,Ghisalberti, Emilio L.,Dixon, Kingsley W.,Trengove, Robert D.
, p. 2189 - 2194 (2008/02/04)
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.
VINYLOGOUS 4H-PYRONES AND THEIR USE IN PROMOTING PLANT GROWTH
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Page/Page column 48, (2008/06/13)
This invention resides in a hitherto unknown class of chemical compounds, 2H-furo[2,3-c]pyran-2-ones including derivatives and analogues thereof. It includes methods for making compounds within said class and includes, without limitation, at least the intermediates employed in the generation of said compounds. The invention also relates to the use of vinylogous 4H-pyrones, including but not limited to the hitherto unknown 2H-furo[2,3-c]pyran-2-ones. In one aspect the invention resides in a method comprising the step of: exposing biological plant material to at least a compound of the invention to promoting bioactivity within said material. In another aspect the invention resides in methods for promoting growth of plant material in, for example, smoke-responsive plant species by exposing said material to a compound of the invention. More specifically, the invention relates to the use of said compounds for promoting seed germination of a plant, for example, a smoke-responsive plant.
