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

Result code in 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>

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2017

Confidentiality

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

Name of the periodical

Plant Growth Regulation

ISSN

0167-6903

e-ISSN

—

Volume of the periodical

82

Issue of the periodical within the volume

1

Country of publishing house

NL - THE KINGDOM OF THE NETHERLANDS

Number of pages

7

Pages from-to

47-53

UT code for WoS article

000399235800005

EID of the result in the Scopus database

2-s2.0-85001038033