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

Gavin Flematti, E.D. Goddard-Borger, David Merritt, Emilio Ghisalberti, Kingsley Dixon, R.D. Trengove

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75 Citations (Scopus)

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 2 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.
Original languageEnglish
Pages (from-to)2189-2194
JournalJournal of Agricultural and Food Chemistry
Volume55
Issue number6
DOIs
Publication statusPublished - 2007

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