TY - JOUR

T1 - Structure–Activity Relationship of Phytotoxic Natural 10-Membered Lactones and Their Semisynthetic Derivatives

AU - Dalinova, Anna

AU - Fedorov, Anatoly

AU - Dubovik, Vsevolod

AU - Voitsekhovskaja, Olga V.

AU - Tyutereva, Elena V.

AU - Smirnov, Sergey

AU - Kochura, Dmitriy

AU - Chisty, Leonid

AU - Senderskiy, Igor

AU - Berestetskiy, Alexander

N1 - Dalinova, A.; Fedorov, A.; Dubovik, V.; Voitsekhovskaja, O.; Tyutereva, E.; Smirnov, S.; Kochura, D.; Chisty, L.; Senderskiy, I.; Berestetskiy, A. Structure–Activity Relationship of Phytotoxic Natural 10-Membered Lactones and Their Semisynthetic Derivatives. J. Fungi 2021, 7, 829. https://doi.org/10.3390/jof7100829

PY - 2021/10

Y1 - 2021/10

N2 - 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.

AB - 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.

KW - natural product-derived herbicide

KW - stagonolide

KW - herbarumin

KW - nonenolide

KW - phytotoxicity bioassay

UR - https://www.mdpi.com/2309-608X/7/10/829

M3 - Article

VL - 7

SP - 829

EP - 844

JO - Journal of Fungi

JF - Journal of Fungi

SN - 2309-608X

IS - 10

ER -