Identification of alkyl substituted 2H-furo[2,3-c]pyran-2-ones as germination stimulants present in smoke

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 analog...

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Bibliographic Details
Main Authors: Flematti, G., Ghisalberti, E., Dixon, Kingsley, Trengove, R.
Format: Journal Article
Published: American Chemical Society 2009
Online Access:http://hdl.handle.net/20.500.11937/5585
Description
Summary: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.