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 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.
School of Biomedical, Biomolecular and Chemical Sciences, The University of Western Australia, Crawley, WA 6009, Australia. gavin.flematti@uwa.edu.au
Gavin R
GR
Flematti
Emilio L
EL
Ghisalberti
Kingsley W
KW
Dixon
Robert D
RD
Trengove
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D018525:Germination / Q000187:drug effects*; D012639:Seeds / Q000187:drug effects / Q000502:physiology*; D012906:Smoke / Q000032:analysis*; D032322:Solanum / Q000187:drug effects / Q000502:physiology
D012906:Smoke; C004511:butenolide; D015107:4-Butyrolactone