Structure-activity relationships of N- and S-analogs of the seed germination inhibitor (3,4,5-trimethylfuran-2(5H)-one) for mode of action elucidation

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00475327" target="_blank" >RIV/61388963:_____/17:00475327 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1007/s10725-016-0237-0" target="_blank" >http://dx.doi.org/10.1007/s10725-016-0237-0</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s10725-016-0237-0" target="_blank" >10.1007/s10725-016-0237-0</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Structure-activity relationships of N- and S-analogs of the seed germination inhibitor (3,4,5-trimethylfuran-2(5H)-one) for mode of action elucidation

Popis výsledku v původním jazyce

Smoke-derived butenolides are important germination signaling molecules which may be useful in promoting or controlling germination in agriculture and horticulture. The butenolide 3,4,5-trimethylfuran-2(5H)-one (trimethylbutenolide, TMB) was previously isolated from plant-derived smoke and was found to significantly reduce the germination stimulatory activity of the highly active germination promoter, 3-methyl-2H-furo[2,3-c]pyran-2-one (karrikinolide, KAR(1)), another smoke-derived butenolide, when applied together. In this study, the germination inhibitory activity of eight N-analogs and one S-analog of TMB, modified in position 1 were evaluated. All synthesized analogs significantly reduced the germination of 'Grand Rapids' lettuce (Lactuca sativa) seeds compared to the respective controls, when applied at 1000 mu M alone, or in combination with 0.01 mu M KAR(1). The S-analog was the most active of the test analogs in this study, with inhibitory activity ranging from 10 to 1000 mu M. This was the only compound with activity similar to that of TMB. Thus, these results indicate that N-alkylation of the lactam ring reduces its germination inhibitory activity, while the activity of the S-analog is comparable to TMB. This provides valuable information toward understanding the mode of action of these compounds in regulating germination and for the design of related synthetic compounds with potential use in agriculture or horticulture.

Název v anglickém jazyce

Structure-activity relationships of N- and S-analogs of the seed germination inhibitor (3,4,5-trimethylfuran-2(5H)-one) for mode of action elucidation

Popis výsledku anglicky

Smoke-derived butenolides are important germination signaling molecules which may be useful in promoting or controlling germination in agriculture and horticulture. The butenolide 3,4,5-trimethylfuran-2(5H)-one (trimethylbutenolide, TMB) was previously isolated from plant-derived smoke and was found to significantly reduce the germination stimulatory activity of the highly active germination promoter, 3-methyl-2H-furo[2,3-c]pyran-2-one (karrikinolide, KAR(1)), another smoke-derived butenolide, when applied together. In this study, the germination inhibitory activity of eight N-analogs and one S-analog of TMB, modified in position 1 were evaluated. All synthesized analogs significantly reduced the germination of 'Grand Rapids' lettuce (Lactuca sativa) seeds compared to the respective controls, when applied at 1000 mu M alone, or in combination with 0.01 mu M KAR(1). The S-analog was the most active of the test analogs in this study, with inhibitory activity ranging from 10 to 1000 mu M. This was the only compound with activity similar to that of TMB. Thus, these results indicate that N-alkylation of the lactam ring reduces its germination inhibitory activity, while the activity of the S-analog is comparable to TMB. This provides valuable information toward understanding the mode of action of these compounds in regulating germination and for the design of related synthetic compounds with potential use in agriculture or horticulture.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2017

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Plant Growth Regulation

ISSN

0167-6903

e-ISSN

—

Svazek periodika

82

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

7

Strana od-do

47-53

Kód UT WoS článku

000399235800005

EID výsledku v databázi Scopus

2-s2.0-85001038033