Pityriacitrin marine alkaloids as novel antiviral and anti‐phytopathogenic‐fungus agents

Wang, Tienan; Yang, Shan; Shi, Shao-Yang; Yuan, Wen-Ying; Chen, Jianxin; Duan, Zhongyu; Lu, Aidang; Wang, Ziwen; Wang, Qingmin

doi:10.1002/ps.6510

Cited by 12 publications

(17 citation statements)

References 32 publications

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“…The leaves were sprayed with a 500 μg mL –1 solution of the compounds and cultured in a climate chamber at 25 °C. Changes in plant height and weight were measured after 0, 3, 7, and 10 days . Each measurement was performed in triplicates.…”

Section: Methodsmentioning

confidence: 99%

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Novel Cyclized Derivatives of Ferulic Acid as Potential Antiviral Agents through Activation of Photosynthesis

Gan

Zhang

Lan

et al. 2023

J. Agric. Food Chem.

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To further develop new antiviral agents, several novel cyclized derivatives of ferulic acid were designed and synthesized. Their antiviral activities were evaluated against the cucumber mosaic virus (CMV), pepper mild mottle virus (PMMoV), and tomato spotted wilt virus (TSWV). The results showed that some ferulic acid derivatives exhibited desirable antiviral activities. Particularly, compound 5e exhibited excellent protective activities against CMV, PMMoV, and TSWV, with EC 50 values of 167.2, 102.5, and 145.8 μg mL −1 , respectively, which were superior to those obtained for trans-ferulic acid (581.7, 611.2, and 615.4 μg mL −1 ), dufulin (312.6, 302.5, and 298.2 μg mL −1 ), and ningnanmycin (264.3, 282.5, and 276.5 μg mL −1 ). Thereafter, the protective mechanisms of 5e were evaluated through photosynthesis evaluation, transcriptome profiling, and proteomic analysis. The results indicated that 5e significantly activated the expression levels of photosynthesis-related regulatory genes and proteins in tobacco plants and promoted the accumulation of defense molecules to resist viral infection. Thus, the findings of this study indicated that novel cyclized ferulic acid derivatives are potential antiviral agents that act via regulating photosynthesis in the host.

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Section: Methodsmentioning

confidence: 99%

“…Changes in plant height and weight were measured after 0, 3, 7, and 10 days. 39 Each measurement was performed in triplicates.…”

Section: ■ Introductionmentioning

confidence: 99%

Novel Cyclized Derivatives of Ferulic Acid as Potential Antiviral Agents through Activation of Photosynthesis

Gan

Zhang

Lan

et al. 2023

J. Agric. Food Chem.

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“…According to the reported method, , 500 μg mL –1 compound solution was sprayed on the leaf of tobacco and Chenopodium amaranticolor and then cultured in a climate chamber at 25 °C. Then, the plant height and weight changes after 0, 3, 7, and 10 days were tested.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Novel Antiviral Ferulic Acid–Eugenol and Isoeugenol Hybrids Using Various Link Reactions

Gan

Wang

2021

J. Agric. Food Chem.

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To develop novel antiviral agents, some novel conjugates between ferulic acid and eugenol or isoeugenol were designed and synthesized by the link reaction. The antiviral activities of compounds were evaluated using the half leaf dead spot method. Bioassay results showed acceptable antiviral activities of some conjugates against the tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV). Compounds A9, A10, E1, and E4 showed remarkable curative, protective, and inactivating effects on TMV and CMV at 500 μg mL–1. Notably, these compounds exhibited excellent protective effects on TMV and CMV. The EC50 values of compounds A9, A10, E1, and E4 against TMV were 180.5, 169.5, 211.4, and 135.5 μg mL–1, respectively, and those against CMV were 210.5, 239.1, 218.4, and 178.6 μg mL–1, respectively, which were superior to those of ferulic acid (471.5 and 489.2 μg mL–1), eugenol (456.3 and 463.2 μg mL–1), isoeugenol (478.4 and 487.5 μg mL–1), and ningnanmycin (246.5 and 286.6 μg mL–1). Then, the antiviral mechanisms of compound E4 were investigated by determining defensive enzyme activities and multi-omics analysis. The results indicated that compound E4 resisted the virus infection by enhancing defensive responses via inducing the accumulation of secondary metabolites from the phenylpropanoid biosynthesis pathway in tobacco.

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“…Wang et al . found some β-carboline analogues 7 , hemigossypol 13 , dehydrobufotenine derivatives 14 , pityriacitrin marine alkaloids 15 , pulmonarin alkaloids 16 and hamacanthin derivatives 17 exhibited higher anti-TMV activities than ningnanmycin. Many other natural alkaloids derivatives were also developed as potential TMV inhibitors 18 – 27 .…”

Section: Introductionmentioning

confidence: 98%

Design, synthesis and biological activities of echinopsine derivatives containing acylhydrazone moiety

Cui

Cai

et al. 2022

Sci Rep

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Based on the broad-spectrum biological activities of echinopsine and acylhydrazones, a series of echinopsine derivatives containing acylhydrazone moieties have been designed, synthesized and their biological activities were evaluated for the first time. The bioassay results indicated that most of the compounds showed moderate to good antiviral activities against tobacco mosaic virus (TMV), among which echinopsine (I) (inactivation activity, 49.5 ± 4.4%; curative activity, 46.1 ± 1.5%; protection activity, 42.6 ± 2.3%) and its derivatives 1 (inactivation activity, 44.9 ± 4.6%; curative activity, 39.8 ± 2.6%; protection activity, 47.3 ± 4.3%), 3 (inactivation activity, 47.9 ± 0.9%; curative activity, 43.7 ± 3.1%; protection activity, 44.6 ± 3.3%), 7 (inactivation activity, 46.2 ± 1.6%; curative activity, 45.0 ± 3.7%; protection activity, 41.7 ± 0.9%) showed higher anti-TMV activity in vivo at 500 mg/L than commercial ribavirin (inactivation activity, 38.9 ± 1.4%; curative activity, 39.2 ± 1.8%; protection activity, 36.4 ± 3.4%). Some compounds exhibited insecticidal activities against Plutella xylostella, Mythimna separate and Spodoptera frugiperda. Especially, compounds 7 and 27 displayed excellent insecticidal activities against Plutella xylostell (mortality 67 ± 6% and 53 ± 6%) even at 0.1 mg/L. Additionally, most echinopsine derivatives exhibited high fungicidal activities against Physalospora piricola and Sclerotinia sclerotiorum.

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Pityriacitrin marine alkaloids as novel antiviral and anti‐phytopathogenic‐fungus agents

Cited by 12 publications

References 32 publications

Novel Cyclized Derivatives of Ferulic Acid as Potential Antiviral Agents through Activation of Photosynthesis

Novel Cyclized Derivatives of Ferulic Acid as Potential Antiviral Agents through Activation of Photosynthesis

Synthesis of Novel Antiviral Ferulic Acid–Eugenol and Isoeugenol Hybrids Using Various Link Reactions

Design, synthesis and biological activities of echinopsine derivatives containing acylhydrazone moiety

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