Preparation of 2H-furo[2,3-c]pyran-2-one derivatives and evaluation of their germination-promoting activity.
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.
Flematti
Gavin R
GR
School of Biomedical, Biomolecular and Chemical Sciences, The University of Western Australia, Crawley, WA 6009, Australia. gflematt@chem.uwa.edu.au
Goddard-Borger
Ethan D
ED
Merritt
David J
DJ
Ghisalberti
Emilio L
EL
Dixon
Kingsley W
KW
Trengove
Robert D
RD
D005663:Furans / Q000737:chemistry* / Q000494:pharmacology*; D018525:Germination / Q000187:drug effects*; D029522:Hydrophyllaceae / Q000187:drug effects; D018545:Lactuca / Q000187:drug effects; D008745:Methylation; D011714:Pyrans / Q000737:chemistry* / Q000494:pharmacology*; D012639:Seeds / Q000187:drug effects / Q000254:growth & development; D012906:Smoke / Q000032:analysis; D032322:Solanum / Q000187:drug effects
C488803:3-methyl-2H-furo(2,3-c)pyran-2-one; D005663:Furans; D011714:Pyrans; D012906:Smoke