Structure-activity relationships of analogs of 3,4,5-trimethylfuran-2(5H)-one with germination inhibitory activities

0396377 - ÚOCHB 2014 RIV PT eng J - Článek v odborném periodiku
Pošta, Martin - Light, M. E. - Papenfus, H. B. - Staden van, J. - Kohout, Ladislav
Structure-activity relationships of analogs of 3,4,5-trimethylfuran-2(5H)-one with germination inhibitory activities.
Journal of Plant Physiology. Roč. 170, č. 14 (2013), s. 1235-1242. ISSN 0176-1617. E-ISSN 1618-1328
Grant CEP: GA MŠMT 1M06030
Institucionální podpora: RVO:61388963
Klíčová slova: butenolide * karrikinolide * Lactuca sativa * seed germination * smoke
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 2.770, rok: 2013

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.
Trvalý link: http://hdl.handle.net/11104/0224218