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  • Title: Preparation of 2H-furo[2,3-c]pyran-2-one derivatives and evaluation of their germination-promoting activity.
    Author: Flematti GR, Goddard-Borger ED, Merritt DJ, Ghisalberti EL, Dixon KW, Trengove RD.
    Journal: J Agric Food Chem; 2007 Mar 21; 55(6):2189-94. PubMed ID: 17316021.
    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.
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