Furofuran Lignans for Plant Protection: Discovery of Sesamolin and Its Derivatives as Novel Anti-Tobacco Mosaic Virus and Antibacterial Agents

Chi, Yuan; He, Hong‐Wei; Chen, Caiyun; Zhao, Shuo; Zhou, Huan; Xu, Dan; Liu, Xili; Xu, Gong

doi:10.1021/acs.jafc.3c03257

Cited by 2 publications

(2 citation statements)

References 46 publications

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“…The morphologies were observed using a transmission electron microscope as previously described. 32 Evaluation of Binding Capacity of syn-3g to TMV-CP. As per our earlier work, the target TMV-CP was prepared.…”

Section: -(34-dimethoxybenzyl)dihydrofuran-2(3h)-one (8)mentioning

confidence: 99%

“…The molecular docking study was conducted using Discovery Studio 4.0 (DS 4.0), following a previously established method. 32 ■ RESULTS AND DISCUSSION Synthesis of the Target Compounds 3a−3z, 4g, 5a− 5n, 6g, 7, and 8. As shown in Figure 3, the target compounds 3a−3z, 4g, 5a−5n, and 6g were synthesized from substituted benzaldehydes 1a−1z and γ-butyrolactone 2.…”

Section: -(34-dimethoxybenzyl)dihydrofuran-2(3h)-one (8)mentioning

confidence: 99%

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Structural Simplification of Podophyllotoxin: Discovery of γ-Butyrolactone Derivatives as Novel Antiviral Agents for Plant Protection

Xu,

Chi,

et al. 2024

J. Agric. Food Chem.

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Natural products are a valuable resource for the discovery of novel crop protection agents. A series of γ-butyrolactone derivatives, derived from the simplification of podophyllotoxin’s structure, were synthesized and assessed for their efficacy against tobacco mosaic virus (TMV). Several derivatives exhibited notable antiviral properties, with compound 3g demonstrating the most potent in vivo anti-TMV activity. At 500 μg/mL, compound 3g achieved an inactivation effect of 87.8%, a protective effect of 71.7%, and a curative effect of 67.7%, surpassing the effectiveness of the commercial plant virucides ningnanmycin and ribavirin. Notably, the syn-diastereomer (syn-3g) exhibited superior antiviral activity compared to the anti-diastereomer (anti-3g). Mechanistic studies revealed that syn-3g could bind to the TMV coat protein and interfere with the self-assembly process of TMV particles. These findings indicate that compound 3g, with its simple chemical structure, could be a potential candidate for the development of novel antiviral agents for crop protection.

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Section: -(34-dimethoxybenzyl)dihydrofuran-2(3h)-one (8)mentioning

confidence: 99%

Section: -(34-dimethoxybenzyl)dihydrofuran-2(3h)-one (8)mentioning

confidence: 99%

Structural Simplification of Podophyllotoxin: Discovery of γ-Butyrolactone Derivatives as Novel Antiviral Agents for Plant Protection

Xu,

Chi,

et al. 2024

J. Agric. Food Chem.

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Design, Synthesis, and Antiviral and Fungicidal Activities of 4-Oxo-4H-quinolin-1-yl Acylhydrazone Derivatives

Cui,

Liu,

Yang

et al. 2024

ACS Omega

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To discover novel antiviral agents, based on the high antiviral activity of (4-oxo-4H-quinolin-1-yl)-acetic acid hydrazide (C), a series of 4-oxo-4H-quinoline acylhydrazone derivatives were designed, synthesized, and first evaluated for their antiviral and fungicidal activities. Most acylhydrazone derivatives exhibited moderate to good antiviral activities in vivo. The inactive, curative, and protective activities of compounds 4 (51.2, 47.6, and 46.3%), 11 (49.6, 43.0, and 45.2% at 500 mg/L), and 17 (47.1, 49.2, and 44.1%) were higher than those of ribavirin (39.2, 38.0, and 40.8%) at 500 mg/L. Molecular docking showed that compound 4 exhibited a stronger affinity to TMV coat protein (TMV-CP) than ribavirin, with a binding energy (−6.89 kcal/mol) slightly lower than that of ribavirin (−6.08 kcal/mol). Microscale thermophoresis showed that compound 4 (K d = 0.142 ± 0.060 μM) exhibited a strong binding ability to TMV-CP, superior to that of ribavirin (K d = 0.512 ± 0.257 μM). The results of transmission electron microscopy showed that compound 4 hindered the self-assembly and growth of TMV. The antifungal activities of most compounds were moderate at 50 mg/L, among which compounds 12 and 21 exhibited a 72.1 and 76.5% inhibitory rate against Physalospora piricola, respectively. Meanwhile, compound 16 exhibited a 60% inhibitory rate against Cercospora arachidicola Hori at 50 mg/L.

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Furofuran Lignans for Plant Protection: Discovery of Sesamolin and Its Derivatives as Novel Anti-Tobacco Mosaic Virus and Antibacterial Agents

Cited by 2 publications

References 46 publications

Structural Simplification of Podophyllotoxin: Discovery of γ-Butyrolactone Derivatives as Novel Antiviral Agents for Plant Protection

Structural Simplification of Podophyllotoxin: Discovery of γ-Butyrolactone Derivatives as Novel Antiviral Agents for Plant Protection

Design, Synthesis, and Antiviral and Fungicidal Activities of 4-Oxo-4H-quinolin-1-yl Acylhydrazone Derivatives

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