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

2021 ◽  
Vol 7 (10) ◽  
pp. 829
Author(s):  
Anna Dalinova ◽  
Anatoly Fedorov ◽  
Vsevolod Dubovik ◽  
Olga Voitsekhovskaja ◽  
Elena Tyutereva ◽  
...  
Keyword(s):  
Rational Design ◽  
Fungicidal Activity ◽  
Structural Features ◽  
Hydroxyl Group ◽  
High Yield ◽  
Sf9 Cells ◽  
Structure Activity ◽  
Relationship Of ◽  
Derivatives Of ◽  
Target Activity

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.

New 4-Hydroxypyridine and 4-Hydroxyquinoline Derivatives as Inhibitors of NADH-ubiquinone Reductase in the Respiratory Chain

1989 ◽  
Vol 44 (7-8) ◽  
pp. 609-616 ◽  
Author(s):  
Kun Hoe Chung ◽  
Kwang Yun Cho ◽  
Yasuko Asami ◽  
Nobutaka Takahashi ◽  
Shigeo Yoshida
Keyword(s):  
Electron Transport ◽  
Respiratory Chain ◽  
Side Chain ◽  
Pyridine Derivatives ◽  
Transport Function ◽  
Optimal Length ◽  
Structure Activity ◽  
Membrane Effect ◽  
Relationship Of ◽  
Derivatives Of

Many derivatives of 2,3-dim ethoxy-4-hydroxypyridine, which were designed from examination of the structure-activity relationship of piericidins, were tested for inhibition of NADH-UQ reductase. The lipophilic side chain of those compounds was indicated to be a key part for activity and its optimal length was conjectured. By the use of two different phases of assay material, intact mitochondria and submitochondria, the size of a membrane effect was shown to depend on the structure of the side chain. 4-Hydroxyquinoline derivatives were also tested for an analogous role in relation to the electron transport function of menaquinone, and they were proven to be inhibitors of NADH-UQ reductase as good as the pyridine derivatives.

scholarly journals From in vitro to in cellulo: structure–activity relationship of (2-nitrophenyl)methanol derivatives as inhibitors of PqsD in Pseudomonas aeruginosa

2014 ◽  
Vol 12 (32) ◽  
pp. 6094-6104 ◽  
Author(s):  
Michael P. Storz ◽  
Giuseppe Allegretta ◽  
Benjamin Kirsch ◽  
Martin Empting ◽  
Rolf W. Hartmann
Keyword(s):  
Pseudomonas Aeruginosa ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Structure Activity Relationships ◽  
Structure Activity ◽  
Relationship Of ◽  
Derivatives Of

More than 60 derivatives of (2-nitrophenyl)methanol were synthesized and evaluated regarding their potency to inhibit PqsD. In vitro and in cellulo structure–activity relationships were derived.

Structure–activity relationship of boronic acid derivatives of tyropeptin: Proteasome inhibitors

2010 ◽  
Vol 20 (19) ◽  
pp. 5839-5842 ◽  
Author(s):  
Takumi Watanabe ◽  
Hikaru Abe ◽  
Isao Momose ◽  
Yoshikazu Takahashi ◽  
Daishiro Ikeda ◽  
...  
Keyword(s):  
Boronic Acid ◽  
Proteasome Inhibitors ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Structure Activity ◽  
Boronic Acid Derivatives ◽  
Relationship Of ◽  
Derivatives Of

scholarly journals The Effect of Cytochalasans on the Actin Cytoskeleton of Eukaryotic Cells and Preliminary Structure–Activity Relationships

Biomolecules ◽  
2019 ◽  
Vol 9 (2) ◽  
pp. 73 ◽  
Author(s):  
Robin Kretz ◽  
Lucile Wendt ◽  
Sarunyou Wongkanoun ◽  
J. Luangsa-ard ◽  
Frank Surup ◽  
...  
Keyword(s):  
Actin Cytoskeleton ◽  
High Resolution Mass Spectrometry ◽  
Structural Features ◽  
Eukaryotic Cells ◽  
Hydroxyl Group ◽  
Fungal Metabolites ◽  
Factors Affecting ◽  
Structure Activity ◽  
Exact Effect

In our ongoing search for new bioactive fungal metabolites, two new cytochalasans were isolated from stromata of the hypoxylaceous ascomycete Hypoxylon fragiforme. Their structures were elucidated via high-resolution mass spectrometry (HR-MS) and nuclear magnetic resonance (NMR) spectroscopy. Together with 23 additional cytochalasans isolated from ascomata and mycelial cultures of different Ascomycota, they were tested on their ability to disrupt the actin cytoskeleton of mammal cells in a preliminary structure–activity relationship study. Out of all structural features, the presence of hydroxyl group at the C7 and C18 residues, as well as their stereochemistry, were determined as important factors affecting the potential to disrupt the actin cytoskeleton. Moreover, reversibility of the actin disrupting effects was tested, revealing no direct correlations between potency and reversibility in the tested compound group. Since the diverse bioactivity of cytochalasans is interesting for various applications in eukaryotes, the exact effect on eukaryotic cells will need to be determined, e.g., by follow-up studies involving medicinal chemistry and by inclusion of additional natural cytochalasans. The results are also discussed in relation to previous studies in the literature, including a recent report on the anti-Biofilm activities of essentially the same panel of compounds against the pathogenic bacterium, Staphylococcus aureus.

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