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Preparation of 2H-Furo[2,3-c]pyran-2-one Derivatives and Evaluation of Their Germination-Promoting Activity

Flematti, G.R., Goddard-Borger, E.D., Merritt, D.J., Ghisalberti, E.L., Dixon, K.W. and Trengove, R.D. (2007) Preparation of 2H-Furo[2,3-c]pyran-2-one Derivatives and Evaluation of Their Germination-Promoting Activity. Journal of Agricultural and Food Chemistry, 55 (6). pp. 2189-2194.

Link to Published Version: http://dx.doi.org/10.1021/jf0633241
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Abstract

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.

Item Type: Journal Article
Murdoch Affiliation(s): School of Biological Sciences and Biotechnology
Publisher: American Chemical Society
Copyright: © 2007 American Chemical Society.
URI: http://researchrepository.murdoch.edu.au/id/eprint/9034
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