Insights into a class of natural eugenol and its optimized derivatives as potential tobacco mosaic virus helicase inhibitors by structure-based virtual screening

Liu, Zhenxing; Yang, Binxin; Ding, Yue; Meng, Jiao; Jin-hong, HU; Zhou, Xiang; Liu, Liwei; Wu, Zhibing; Yang, Song

doi:10.1016/j.ijbiomac.2023.125892

Cited by 12 publications

(3 citation statements)

References 51 publications

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“…Hence, a molecular docking technique was carried out to further verify the anti-inflammatory mechanism of compound 7. [34,35] The molecular docking modes of 7 with iNOS (PDB ID:3E7G) (Figure 7A): (i) H-4 and H-5, as well as H-5' formed SÀ H interaction with the residues Met434 and Cys200, respectively; (ii) the carbonyl of C-1'' and C-1''' generated hydrogen bonds with the residues Gly371; (iii) the pyranone unit established PiÀ H interactions with Trp372 and Gly371, as well as Me-4''' of side chain interacted with Trp194 through PiÀ H interaction.…”

Section: Molecular Docking Studiesmentioning

confidence: 99%

Structurally Diverse Coumarins from Peucedanum praeruptorum and their Anti‐Inflammatory Activities via NF‐κB Signaling Pathway

Lin,

Liu,

Chen

et al. 2024

Chemistry & Biodiversity

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The phytochemical study of Peucedanum praeruptorum led to the isolation of twenty‐five coumarins (1‐25). Of which, (±) praeruptol A (±1), one pair of previous undescribed seco‐coumarin enantiomers were obtained. Their structures were established according to HR‐ESI‐MS, NMR, X‐ray single crystal diffraction analysis, as well as ECD calculation. All compounds were tested for anti‐inflammatory activity in the RAW264.7 macrophage model, and eight compounds (7‐10, and 13‐16) exhibited significant inhibitory effects with IC50 values ranging from 9.48 to 34.66 μM. Among them, compound 7 showed the strongest inhibitory effect, which significantly suppressed the production of IL‐6, IL‐1β, and TNF‐α, as well as iNOS and COX‐2 in a concentration‐dependent manner. Further investigated results showed that compound 7 exerted an anti‐inflammatory effect via the NF‐κB signaling pathway.

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Section: Molecular Docking Studiesmentioning

confidence: 99%

Structurally Diverse Coumarins from Peucedanum praeruptorum and their Anti‐Inflammatory Activities via NF‐κB Signaling Pathway

Lin,

Liu,

Chen

et al. 2024

Chemistry & Biodiversity

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“…The use of fungicides is the preferred preventive measure for the effective control of most plant pathogens in agriculture. Many achievements were made for controlling plant diseases, such as 18β-glycyrrhetinic acid amide derivatives, [1] 1,2,3,4-Tetrahydro-β-carbolines, [2] ursolic acid derivatives, [3] 1,3,4-Oxadiazole-2-carbohydrazides SDH inhibitors, [4] eugenol derivatives, [5] phenothiazine analogues as mimics of host defense peptides (HDPs), [6] and the establishment of an intelligent photoresponsive pesticide delivery system based on β-cyclodextrin (β-CD) and azobenzene. [7] However, fungicides are facing some problems, such as antimicrobial resistance, residual pesticide, and the reduction of authorization in some countries.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antifungal Activity of Coumarin Derivatives Containing Hydrazone Moiety

Zhang,

Geng,

Yang

et al. 2024

Chemistry & Biodiversity

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Plant disease control mainly relies on pesticides. In this study, a series of coumarin derivatives containing hydrazone moiety were designed and synthesized. The synthesized compounds were characterized and used to evaluate the antifungal activity against four pathogens, Botrytis cinerea, Alternaria solani, Fusarium oxysporum, and Alternaria alternata. The results showed that the inhibition rate of some compounds at 100 µg/mL in 96 hours reached around 70% against A. alternata, higher than that of positive control. The corresponding EC50 values were found at around 30 µg/mL. Finally, the compound 3b was screened out with the lowest EC50 value (19.49 μg/mL). The analysis of SEM and TEM confirmed that the compound 3b can obviously damage the morphological structure of hyphae, resulting in the depletion of the cells by the destruction of membranous structure and leakage of cytoplasmic contents. RNA sequencing showed that compounds 3b mainly affected the pentose phosphate pathway, which in turn caused damage to the cell membrane wall structure and function. Molecular docking showed that compounds 3b fitted the binding pocket of yeast transketolase and interacted with lysine at the hydrazone structure. Our results suggested that the introduction of hydrazone was an effective strategy for the design of novel bioactive compounds

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“…Although it is abundant in cloves ( Syzygium aromaticum ), it can also be found in various plants, giving them its typical pleasant odor and taste. The high value of this compound and its derivatives in the medicinal chemistry field is justified by its multifaceted activities, including its broad-spectrum antibacterial [ 7 , 8 ], antioxidant [ 9 , 10 ], antifungal [ 11 , 12 , 13 ], antiviral [ 14 , 15 , 16 ] and antiprotozoal [ 17 ] properties, among its many others [ 18 , 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Nature-Inspired Compounds: Synthesis and Antibacterial Susceptibility Testing of Eugenol Derivatives against H. pylori Strains

Carradori,

Ammazzalorso,

Niccolai

et al. 2023

Pharmaceuticals

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The antimicrobial properties of one of the most important secondary metabolites, Eugenol (EU), inspired us to design and synthesize three different series of derivatives enhancing its parent compound’s anti-Helicobacter pylori activity. Thus, we prepared semisynthetic derivatives through (A) diazo aryl functionalization, (B) derivatization of the hydroxy group of EU, and (C) elongation of the allyl radical by incorporating a chalcogen atom. The antibacterial evaluation was performed on the reference NCTC 11637 strain and on three drug-resistant clinical isolates and the minimal inhibitory and bactericidal concentrations (MICs and MBCs) highlight the role of chalcogens in enhancing the antimicrobial activity (less than 4 µg/mL for some compounds) of the EU scaffold (32–64 µg/mL).

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Insights into a class of natural eugenol and its optimized derivatives as potential tobacco mosaic virus helicase inhibitors by structure-based virtual screening

Cited by 12 publications

References 51 publications

Structurally Diverse Coumarins from Peucedanum praeruptorum and their Anti‐Inflammatory Activities via NF‐κB Signaling Pathway

Structurally Diverse Coumarins from Peucedanum praeruptorum and their Anti‐Inflammatory Activities via NF‐κB Signaling Pathway

Synthesis and Antifungal Activity of Coumarin Derivatives Containing Hydrazone Moiety

Nature-Inspired Compounds: Synthesis and Antibacterial Susceptibility Testing of Eugenol Derivatives against H. pylori Strains

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