Structure-Activity Relationship of Phytotoxic Natural 10-Membered Lactones and Their Semisynthetic Derivatives
Autor: | Elena V. Tyutereva, Vsevolod Dubovik, Alexander Berestetskiy, Sergey N. Smirnov, Dmitry Kochura, Olga V. Voitsekhovskaja, Leonid Chisty, Anatoly Fedorov, Igor Senderskiy, Anna Dalinova |
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Rok vydání: | 2021 |
Předmět: |
Microbiology (medical)
biology QH301-705.5 Chemistry Stereochemistry stagonolide Rational design Biological activity Plant Science Bacillus subtilis natural product-derived herbicide Antimicrobial biology.organism_classification Article Fungicide nonenolide Stagonospora Structure–activity relationship Phytotoxicity herbarumin phytotoxicity bioassay Biology (General) Ecology Evolution Behavior and Systematics |
Zdroj: | Journal of Fungi Volume 7 Issue 10 Journal of Fungi, Vol 7, Iss 829, p 829 (2021) |
ISSN: | 2309-608X |
Popis: | Ten-membered lactones (nonenolides) demonstrate phytotoxic, antimicrobial, and fungicidal activity promising for the development of natural product-derived pesticides. The fungus Stagonospora cirsii is able to produce phytotoxic stagonolides A (1), J (2), K (3) and herbarumin I (4) with high yield. The aim of this study was to create a set of structurally related nonenolides and to reveal the structural features that affect their biological activity. Stagonolide A (1) and C-7 oxidized stagonolide K (11) showed the highest phytotoxicity in leaf puncture assay and agar seedlings assay. The oxidation of C-7 hydroxyl group (as in 1, acetylstagonolide A (10) and (11) led to the manifestation of toxicity to microalgae, Bacillus subtilis and Sf9 cells regardless of the configuration of C-9 propyl chains (R in 1 and 10, S in 11). C-7 non-oxidized nonenolides displayed none or little non-target activity. Notably, 7S compounds were more phytotoxic than their 7R analogues. Due to the high inhibitory activity against seedling growth and the lack of side toxicity, mono- and bis(acetyl)- derivatives of herbarumin I were shown to be potent for the development of pre-emergent herbicides. The identified structural features can be used for the rational design of new herbicides. |
Databáze: | OpenAIRE |
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