About: Structure-activity relationships of analogs of 3,4,5-trimethylfuran-2(5H)-one with germination inhibitory activities     Goto   Sponge   NotDistinct   Permalink

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  • Smoke-derived butenolide compounds have, in recent years, been shown to be important germination signaling molecules, which also affect seedling growth. The butenolide 3,4,5-trimethylfuran-2(5H)-one was previously isolated from plant-derived smoke and was found to significantly reduce the effect on germination by the highly active promotor karrikinolide (KAR(1), 3-methyl-2H-furo[2,3-c]pyran-2-one), another smoke-derived compound. In this study, 11 analogs of 3,4,5-trimethylfuran-2(5H)-one were synthesized and their effect on the germination of light-sensitive 'Grand Rapids' lettuce seeds (Lactua sativa cv. 'Grand Rapids') were evaluated. A concentration series (1 mM-1 mu M) of the analogs were tested alone, or in combination with 0.01 mu M KAR(1). Only two compounds were found to reduce the germination promotory effect of 0.01 mu M KAR(1) in a similar manner as observed with 3,4,5-trimethylfuran-2(5H)-one, with activity ranging from 1 mM to 10 mu M. Four compounds were found to have inhibitory activity at 1 mM and 100 mu M. The retention of activity by some of the analogs may be useful for designing novel compounds with improved activity. Furthermore, understanding the structure-activity relationships of these compounds may be helpful in synthesizing molecular probes that can be used to further investigate the mechanism of action of these compounds in regulating seed germination.
  • Smoke-derived butenolide compounds have, in recent years, been shown to be important germination signaling molecules, which also affect seedling growth. The butenolide 3,4,5-trimethylfuran-2(5H)-one was previously isolated from plant-derived smoke and was found to significantly reduce the effect on germination by the highly active promotor karrikinolide (KAR(1), 3-methyl-2H-furo[2,3-c]pyran-2-one), another smoke-derived compound. In this study, 11 analogs of 3,4,5-trimethylfuran-2(5H)-one were synthesized and their effect on the germination of light-sensitive 'Grand Rapids' lettuce seeds (Lactua sativa cv. 'Grand Rapids') were evaluated. A concentration series (1 mM-1 mu M) of the analogs were tested alone, or in combination with 0.01 mu M KAR(1). Only two compounds were found to reduce the germination promotory effect of 0.01 mu M KAR(1) in a similar manner as observed with 3,4,5-trimethylfuran-2(5H)-one, with activity ranging from 1 mM to 10 mu M. Four compounds were found to have inhibitory activity at 1 mM and 100 mu M. The retention of activity by some of the analogs may be useful for designing novel compounds with improved activity. Furthermore, understanding the structure-activity relationships of these compounds may be helpful in synthesizing molecular probes that can be used to further investigate the mechanism of action of these compounds in regulating seed germination. (en)
Title
  • Structure-activity relationships of analogs of 3,4,5-trimethylfuran-2(5H)-one with germination inhibitory activities
  • Structure-activity relationships of analogs of 3,4,5-trimethylfuran-2(5H)-one with germination inhibitory activities (en)
skos:prefLabel
  • Structure-activity relationships of analogs of 3,4,5-trimethylfuran-2(5H)-one with germination inhibitory activities
  • Structure-activity relationships of analogs of 3,4,5-trimethylfuran-2(5H)-one with germination inhibitory activities (en)
skos:notation
  • RIV/61388963:_____/13:00396377!RIV14-MSM-61388963
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • I, P(1M06030)
http://linked.open...iv/cisloPeriodika
  • 14
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 108425
http://linked.open...ai/riv/idVysledku
  • RIV/61388963:_____/13:00396377
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • butenolide; karrikinolide; Lactuca sativa; seed germination; smoke (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • PT - Portugalská republika
http://linked.open...ontrolniKodProRIV
  • [B4B6ABFE0CDF]
http://linked.open...i/riv/nazevZdroje
  • Journal of Plant Physiology
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...vavai/riv/projekt
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 170
http://linked.open...iv/tvurceVysledku
  • Kohout, Ladislav
  • Light, M. E.
  • Pošta, Martin
  • Papenfus, H. B.
  • Staden van, J.
http://linked.open...ain/vavai/riv/wos
  • 000324081200003
issn
  • 0176-1617
number of pages
http://bibframe.org/vocab/doi
  • 10.1016/j.jplph.2013.04.002
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