Design, Synthesis, Antiviral Bioactivity, and Mechanism of the Ferulic Acid Ester-Containing Sulfonamide Moiety

Ren, Xiaohu; Li, Xiangyang; Yin, Limin; Jiang, Donghao; Hu, Deyu

doi:10.1021/acsomega.0c02421

Cited by 31 publications

(26 citation statements)

References 32 publications

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“…In recent years, other authors considered TMV CP an important target for screening viral agents against tobamoviruses [ 90 , 97 , 104 , 105 , 106 , 107 ]. Careful literature overview highlighted several in silico studies based on the crystal structure of TMV CP (PDB code 1ei7) [ 39 , 72 , 73 , 89 , 91 , 94 , 97 , 105 , 106 , 107 ]. Due to the high conservation of the tobamovirus CP sequences [ 108 ] in this study, we considered the TMV CP sequence as a template.…”

Section: Discussionmentioning

confidence: 99%

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Autoxidation Products of the Methanolic Extract of the Leaves of Combretum micranthum Exert Antiviral Activity against Tomato Brown Rugose Fruit Virus (ToBRFV)

Iobbi

Lanteri²,

Minuto³

et al. 2022

Molecules

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Tomato brown rugose fruit virus (ToBRFV) is a new damaging plant virus of great interest from both an economical and research point of view. ToBRFV is transmitted by contact, remains infective for months, and to-date, no resistant cultivars have been developed. Due to the relevance of this virus, new effective, sustainable, and operator-safe antiviral agents are needed. Thus, 4-hydroxybenzoic acid was identified as the main product of the alkaline autoxidation at high temperature of the methanolic extract of the leaves of C. micranthum, known for antiviral activity. The autoxidized extract and 4-hydroxybenzoic acid were assayed in in vitro experiments, in combination with a mechanical inoculation test of tomato plants. Catechinic acid, a common product of rearrangement of catechins in hot alkaline solution, was also tested. Degradation of the viral particles, evidenced by the absence of detectable ToBRFV RNA and the loss of virus infectivity, as a possible consequence of disassembly of the virus coat protein (CP), were shown. Homology modeling was then applied to prepare the protein model of ToBRFV CP, and its structure was optimized. Molecular docking simulation showed the interactions of the two compounds, with the amino acid residues responsible for CP-CP interactions. Catechinic acid showed the best binding energy value in comparison with ribavirin, an anti-tobamovirus agent.

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Section: Discussionmentioning

confidence: 99%

“…Activity of plant compounds against phyto-viruses has been reported [ 30 , 31 , 32 ]. Plant phenolic compounds are involved in plant defense [ 33 , 34 ] and show several properties against a wide spectrum of plant pathogens [ 35 , 36 ], specifically against various viruses, including tobamoviruses [ 37 , 38 , 39 , 40 ].…”

Section: Introductionmentioning

confidence: 99%

Autoxidation Products of the Methanolic Extract of the Leaves of Combretum micranthum Exert Antiviral Activity against Tomato Brown Rugose Fruit Virus (ToBRFV)

Iobbi

Lanteri²,

Minuto³

et al. 2022

Molecules

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“…FA is required for the stiffness of the cell wall and acts as an antioxidant, antimicrobial, anticarcinogenic, antiviral, and enzyme activity modulator [82]. The application of ferulic acid amide derivatives at 500 µg/mL exhibited higher protective and curative activities against TMV than the ribavirin (control) compound [83,84]. Caffeic acid is a hydroxycinnamic acid with many acrylic functional groups and is most commonly produced from plants.…”

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confidence: 99%

First Report of Protective Activity of Paronychia argentea Extract against Tobacco Mosaic Virus Infection

Abdelkhalek

Al-Askar

AlSubaie

et al. 2021

Plants

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The widespread use of chemical control agents and pesticides for plant-pathogen control has caused many human health and environmental issues. Plant extracts and biocontrol agents have robust antimicrobial activity against different plant pathogens. However, their antiviral activities are still being investigated. In the present study, the methanol extract of Paronychia argentea was characterized and evaluated for its protective activity against the tobacco mosaic virus (TMV) infection in tomato plants under greenhouse conditions at 21 days post-inoculation. The results showed that the foliar application of P. argentea extract (10 µg/mL) enhanced tomato plant growth, resulting in significant increases in shoot and root parameters and total chlorophyll contents. Moreover, a significant reduction in TMV accumulation level in P. argentea-treated plants of 77.88% compared to non-treated plants was reported. Furthermore, induction of systemic resistance with significant elevation in production of antioxidant enzymes (PPO, CAT, and SOD) and transcriptional levels of the pathogenesis-related proteins (PR-1 and PR-7) and polyphenolic genes (CHS and HQT) were also observed. Out of 16 detected compounds, HPLC analysis revealed that the most abundant polyphenolic compounds found in P. argentea extract were gallic acid (5.36 µg/mL), kaempferol (7.39 µg/mL), quercetin (7.44 µg/mL), ellagic acid (7.89 µg/mL), myricetin (8.36 µg/mL), and ferulic acid (8.69 µg/mL). The findings suggest that the use of P. argentea extract as an effective and safe source for the production of bioactive compounds may offer a solution for a promising approach for the management of plant viral infections. To the best of our knowledge, this is the first report of the protective activity of P. argentea extract against plant viral diseases.

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“…According to the classic literature method ( Ren et al, 2020 ), the activity of the target compound H1–H23 on TMV was tested. Preliminary bioactivity showed that most of the compounds exhibited a good inhibitory effect on TMV at 500 μg/ml.…”

Section: Resultsmentioning

confidence: 99%

1,3,4-Oxadiazole Contained Sesquiterpene Derivatives: Synthesis and Microbiocidal Activity for Plant Disease

Dai

Zheng

et al. 2022

Front. Chem.

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A series of 1,3,4-oxadiazole contained sesquiterpene derivatives were synthesized, and the activity of the target compounds against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas axonopodis pv. citri (Xac), and tobacco mosaic virus (TMV) were evaluated. The biological activity results showed that the EC50 values of compounds H4, H8, H11, H12, H14, H16, and H19 for Xac inhibitory activity were 33.3, 42.7, 56.1, 74.5, 37.8, 43.8, and 38.4 μg/ml, respectively. Compounds H4, H8, H15, H19, H22, and H23 had inhibitory effects on Xoo, with EC50 values of 51.0, 43.3, 43.4, 50.5, 74.6, and 51.4 μg/ml, respectively. In particular, the curative and protective activities of compound H8 against Xoo in vivo were 51.9 and 49.3%, respectively. In addition, the EC50 values of the inactivation activity of compounds H4, H5, H9, H10, and H16 against TMV were 69.6, 58.9, 69.4, 43.9, and 60.5 μg/ml, respectively. The results of molecular docking indicated that compound H10 exhibited a strong affinity for TMV-coat protein, with a binding energy of −8.88 kcal/mol. It may inhibit the self-assembly and replication of TMV particles and have an anti-TMV effect, which supports its potential usefulness as an antiviral agent.

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Design, Synthesis, Antiviral Bioactivity, and Mechanism of the Ferulic Acid Ester-Containing Sulfonamide Moiety

Cited by 31 publications

References 32 publications

Autoxidation Products of the Methanolic Extract of the Leaves of Combretum micranthum Exert Antiviral Activity against Tomato Brown Rugose Fruit Virus (ToBRFV)

Autoxidation Products of the Methanolic Extract of the Leaves of Combretum micranthum Exert Antiviral Activity against Tomato Brown Rugose Fruit Virus (ToBRFV)

First Report of Protective Activity of Paronychia argentea Extract against Tobacco Mosaic Virus Infection

1,3,4-Oxadiazole Contained Sesquiterpene Derivatives: Synthesis and Microbiocidal Activity for Plant Disease

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