Research output: Contribution to journal › Article › peer-review
Structure–Activity Relationship of Phytotoxic Natural 10-Membered Lactones and Their Semisynthetic Derivatives. / Dalinova, Anna; Fedorov, Anatoly; Dubovik, Vsevolod; Voitsekhovskaja, Olga V.; Tyutereva, Elena V.; Smirnov, Sergey ; Kochura, Dmitriy; Chisty, Leonid; Senderskiy, Igor; Berestetskiy, Alexander.
In: Journal of Fungi, Vol. 7, No. 10, 10.2021, p. 829-844.Research output: Contribution to journal › Article › peer-review
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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 -
ID: 86186827