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PEST MANAGEMENT SCIENCE · 2024 · IF 3.8

Design, synthesis and Anti-PVY activity of planar chiral thiourea derivatives incorporated with [2.2]Paracyclophane

Liangzhen Shu,Ya Lv,Zhongyin Chen,Yixian Huang,Meng Zhang,Zhichao Jin,Tingting Li,Yonggui Robin Chi

BACKGROUND Potato virus Y (PVY) is a prominent representative of plant viruses. It can inflict severe damage upon Solanaceae plants, leading to global dissemination and substantial economic losses. To discover new antiviral agents, a class of planar chiral thiourea molecules through the key step of N -heterocyclic carbene-catalyzed nitrile formation reaction was synthesized with excellent optical purities for antiviral evaluations against plant virus PVY. RESULTS The absolute configurations of the planar chiral compounds exhibited obvious distinctions in the anti-PVY activities. Notability, compound ( S )- 4u exhibited remarkable curative activities against PVY, with a half maximal effective concentration (EC 50 ) of 349.3 μg mL −1 , which was lower than that of the ningnanmycin (NNM) (EC 50 = 400.8 μg mL −1 ). Additionally, The EC 50 value for the protective effects of ( S )- 4u was 146.2 μg mL −1 , which was superior to that of NNM (276.4 μg mL −1 ). Furthermore, the mechanism-of-action of enantiomers of planar chiral compound 4u was investigated through molecular docking, defensive enzyme activity tests and chlorophyll content tests. CONCLUSION Biological mechanism studies have demonstrated that the configuration of planar chiral target compounds plays a crucial role in the molecular interaction with PVY-CP, enhancing the activity of defense enzymes and affecting chlorophyll content. The current study has provided significant insights into the roles played by planar chiralities in plant protection against viruses. This paves the way for the development of novel green pesticides bearing planar chiralities with excellent optical purities. © 2024 Society of Chemical Industry.

研究领域: 植物病理学 · 有机化学 · 药学 · 生物化学 · 农业科学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2024 · IF 5.7

Ningnanmycin Activates Defense Systems against Potato Virus Y in Nicotiana benthamiana

Zilin Wu,Min Huang,Junmei Jiang,Chun Zhang,Gefei Hao,Moxian Chen,Qing X. Li,Mengao Jia,Junfeng Liu,Xiangyang Li

Ningnanmycin has been proven to effectively inhibit infection by potato virus Y (PVY), although its underlying mechanisms remain unclear. In this study, we report a novel finding that ningnanmycin affects PVY replication. Two approaches were employed: studies using PVY movement-deficient mutants suggest that ningnanmycin, at a concentration of 500 μg/mL, inhibits PVY replication. Ningnanmycin interacts with the PVY-encoded coat protein (CP) with a binding constant of 1.34 μmol/L, and key amino acids Glu168 and Thr206 are involved in this interaction. Additionally, ningnanmycin induces the expression of antiviral response genes in Nicotiana benthamiana, including PRXIIB, PRXIIE, PUB4, and PER42. Furthermore, studies revealed that the overexpression of PUB4 in N. benthamiana confers resistance to PVY infection. These findings highlight the mechanisms by which ningnanmycin activates the PUB4 gene and suppresses CP assembly, thereby inhibiting PVY in N. benthamiana. This study represents an important step toward elucidating the molecular mechanism underlying the antiviral activity of ningnanmycin.

CAS / MDL: 36791-04-5
研究领域: 植物病理学 · 病毒学 · 分子生物学 · 植物生物技术
✓ 已验证 产品关联 DOI PubMed 高影响因子
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BMC PLANT BIOLOGY · 2025 ·Vol. 25 ·期 1 ·1613 · IF 4.8

Bacillus subtilis and chitosan nanoparticles enhance potato virus Y (PVY) tolerance in tomato (Solanum lycopersicum L.) via modulation of antioxidants and secondary metabolites

Ghanaim Amira M.,Mahmoud Ghada A.,Mohamed Heba I.,Hanafy Rania S.,Zaki Laila M.,Mahmoud Mohamed,Mogazy Asmaa M.

Background Plant viral infections threaten global food security and cause major crop losses. This study investigates the antiviral effects of biosynthesized Chitosan nanoparticles (ChNPs) with Bacillus subtilis 1211 EMCCN against potato virus Y (PVY) and their influence on tomato growth and yield. Results Scanning electron microscopy showed clusters of crystals on ChNPs, while transmission electron microscopy revealed that the nanoparticles were spherical, ranging from 12 to 198 nm. Energy-dispersive X-ray spectroscopy confirmed the presence of carbon, oxygen, sodium, and phosphorus, and Fourier-transform infrared analysis identified typical chitosan functional groups, including hydroxyl, carbonyl, and amine. Tomato leaves were treated with ChNPs, B. subtilis , or both to evaluate their effectiveness against PVY. The treated plants exhibited a marked reduction in both disease severity and PVY concentration compared to the untreated controls. By 28 days post-inoculation, infectivity decreased to 46.7% in plants treated with Bacillus subtilis, 33.3% with ChNPs, and reached the lowest level of 20% in the combined treatment. The combined priming strategy significantly enhanced plant growth attributes, with increases in shoot length (95.0%), root length (47.0%), leaf area (668.1%), plant height (30.7%), shoot and root fresh weight (370.0% and 162.9%), and shoot and root dry weight (562.7% and 127.7%). Biochemical and physiological analyses revealed substantial increases in total pigments (268.4%), flavonoids (112.2%), phenols (59.4%), α-tocopherol (92.1%), ascorbic acid (30.1%), anthocyanins (71.3%), peroxidase (51.9%), catalase (39.6%), polyphenol oxidase (73.6%), amino acids (119.9%), proline (93.3%), soluble sugars (128.0%), and proteins (614.0%) in shoots. Yield components, including carotenoids and anthocyanins, were also significantly enhanced. Importantly, oxidative stress indicators were markedly reduced, with malondialdehyde and hydrogen peroxide levels decreasing by 76.8% and 72.6%, respectively, in treated plants compared to infected plants. Conclusion These findings suggest that combination between ChNPs and B. subtilis offers an eco-friendly method to enhance tomato yield and effectively manage viral diseases by activating the plants' defense mechanisms.

CAS / MDL: 7758-29-4
研究领域: 植物病理学 · 纳米生物技术 · 农业病毒学 · 作物保护 · 胁迫生理学 · 可持续农业
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2024 · IF 5.7

Discovery of Novel Chiral Indole Derivatives Containing the Oxazoline Moiety as Potential Antiviral Agents for Plants

Yixian Huang,Xiaolin Peng,Jinli Chen,Liangzhen Shu,Meng Zhang,Jiamiao Jin,Zhichao Jin,Yonggui Robin Chi

Potato virus Y (PVY) is an important plant virus that has spread worldwide, causing significant economic losses. To search for novel structures as potent antiviral agents, a series of chiral indole derivatives containing oxazoline moieties were designed and synthesized and their anti-PVY activities were evaluated. Biological activity tests demonstrated that many chiral compounds exhibited promising anti-PVY activities and that their absolute configurations exhibited obvious distinctions in antiviral bioactivities. Notably, compound (S)-4v displayed excellent curative and protective efficacy against PVY, with EC50 values of 328.6 and 256.1 μg/mL, respectively, which were superior to those of commercial virucide ningnanmycin (NNM, 437.4 and 397.4 μg/mL, respectively). The preliminary antiviral mechanism was investigated to determine the difference in antiviral activity between the two enantiomers of 4v chiral compounds. Molecular docking indicated a stronger binding affinity between the coating proteins of PVY (PVY-CP) and (S)-4v (−6.5 kcal/mol) compared to (R)-4v (−6.2 kcal/mol). Additionally, compound (S)-4v can increase the chlorophyll content and defense-related enzyme activities more effectively than its enantiomer. Therefore, this study provides an important basis for the development of chiral indole derivatives containing oxazoline moieties as novel agricultural chemicals.

研究领域: 植物病理学 · 药物化学 · 农业科学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2022 · IF 5.895

3-Hydroxy-2-oxindole Derivatives Containing Sulfonamide Motif: Synthesis, Antiviral Activity, and Modes of Action

Chunle Wei,Xiong Yang,Shaojie Shi,Lian Bai,Deyu Hu,Runjiang Song,Baoan Song

3-Hydroxy-2-oxindole motif constitutes a core structure in numerous natural products and imparts notable biological activities. Here, we describe the design and synthesis of four series of novel 3-substituted-3-hydroxy-2-oxindole derivatives containing sulfonamide moiety along with their antiviral activities against potato virus Y (PVY). Compound 10b displayed optimal antiviral activity and superior anti-PVY activity compared with the lead compound and commercial Ningnanmycin in terms of curative and protective effects. Additionally, 10b considerably inhibited PVY systemic infection in Nicotiana benthamiana. Physiological and biochemical analyses revealed that the activities of the four crucial defense-related enzymes increased in the tobacco plant following treatment with 10b. RNA-sequencing analysis revealed that 10b substantially induced the upregulation of 38 differentially expressed genes, which were enriched in the photosynthesis pathway. These findings suggest that 10b is a promising antiviral agrochemical that can effectively control PVY infection and trigger plant host immunity to develop virus resistance. This study provides novel molecular entities and ideas for developing new pesticides.

研究领域: 有机化学 · 药物化学 · 植物病理学 · 分子生物学 · 农学
✓ 已验证 DOI PubMed 高影响因子
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