Identification of alkyl substituted 2H-furo[2,3-c]pyran-2-ones as germination stimulants present in smoke
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Flematti, G.
Ghisalberti, E.
Dixon, Kingsley
Trengove, R.
Date
2009Type
Journal Article
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Flematti, G. and Ghisalberti, E. and Dixon, K. and Trengove, R. 2009. Identification of alkyl substituted 2H-furo[2,3-c]pyran-2-ones as germination stimulants present in smoke. Journal of Agriculture and Food Chemistry. 57 (20): pp. 9475-9480.
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Journal of Agriculture and Food Chemistry
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Department of Environment and Agriculture
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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 highperformance 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. © 2009 American Chemical Society.
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