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

Flematti, G.R., Ghisalberti, E.L., Dixon, K.W. and Trengove, R.D. (2009) Identification of alkyl substituted 2h-furo[2,3-c]pyran-2-ones as germination stimulants present in smoke. Journal of Agricultural and Food Chemistry, 57 (20). pp. 9475-9480.

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.