Biological Evaluation and In Silico Study of Benzoic Acid Derivatives from Bjerkandera adusta Targeting Proteostasis Network Modules

Georgousaki, K; Tsafantakis, Nikolaos; Gumeni, Sentiljana; Lambrinidis, George; González-Menéndez, Víctor; Tormo, José R.; Genilloud, Olga; Trougakos, Ioannis P.; Fokialakis, Nikolas

doi:10.3390/molecules25030666

Cited by 15 publications

(13 citation statements)

References 60 publications

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“…In addition, there are molecular docking studies reporting that gallic acid, p-coumaric acid, ferulic acid, chicoric acid, cinnamic acid and 4-hydroxybenzoic acid, the other polyphenolic phytochemicals in our study, show high binding affinity for spike, TMPRSS2, CatB and CatL enzymes (Georgousaki et al, 2020;Adem et al, 2021;Guler et al, 2021;Srivastava et al, 2021;Surucic et al, 2021).…”

Section: Discussionsupporting

confidence: 51%

Molecular interactions of some phenolics with 2019-nCoV and related pathway elements

İstifli

Tepe

Sarıkürkçü

et al. 2021

International Journal of Secondary Metabolite

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As of June 2021, the novel coronavirus disease (SARS-CoV-2) resulted in 180 million cases worldwide and resulted in the death of approximately 4 million people. However, an effective pharmaceutical with low side effects that can be used in the treatment of SARS-CoV-2 infection has not been developed yet. The aim of this computational study was to analyze the interactions of twenty-two hydroxycinnamic acid and hydroxybenzoic acid derivatives with the SARS-CoV-2 receptor binding domain (RBD) and host organism's proteases, transmembrane serine protease 2 (TMPRSS2), and cathepsin B and L (CatB/L). According to the RBCI analysis, the ligands with the highest affinity against 4 enzymes in the molecular docking study were determined as 1-caffeoyl-β-D-glucose, rosmarinic acid, 3-p-coumaroylquinic acid and chlorogenic acid. It has also been observed that these compounds interacted more strongly with spike RBD, CatB and CatL enzymes. Although the top-ranked ligand, 1-caffeoyl-β-D-glucose, violated the drug-likeness criteria at 1 point (NH or OH>5) and ADMET in terms of AMES toxicity, the second top-ranked ligand rosmarinic acid neither violated drug-likeness nor exhibited incompatibility in terms of ADMET. In conclusion, with its antiinflammatory properties, rosmarinic acid can be considered and further investigated as a plant-based pharmaceutical that can offer a treatment option in SARS-CoV-2 infection. However, our findings should be supported by additional in vitro and in vivo studies.

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Section: Discussionsupporting

confidence: 51%

Molecular interactions of some phenolics with 2019-nCoV and related pathway elements

İstifli

Tepe

Sarıkürkçü

et al. 2021

International Journal of Secondary Metabolite

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“…The methanolic extract of the leaves of C. micranthum was submitted to alkaline oxidation, under heating at 100 °C, to obtain the alkaline autoxidized methanolic extract (AME) [ 47 ]. The semi-preparative HPLC purification of AME afforded 4-hydroxybenzoic acid ( 2 ) as main compound ( Figure S1 , Supplementary Materials ), identified by the comparison of the spectroscopic data with those reported in the literature [ 77 , 78 ].…”

Section: Resultsmentioning

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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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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“…The concentration range of p-anisic acid (and its conjugates) was set up based on data referring to the biological activities of that compound. It has been shown to influence the enzymatic activity of proteasome and lysosomal cathepsins at such low concentrations as 5 µM (0.76 µg/mL) [ 32 ]. Inhibition of tyrosinase activity was detectable from 0.1 mM (15 µg/mL), with an IC50 value 0.6 mM (91 µg/mL) [ 33 ].…”

Section: Resultsmentioning

confidence: 99%

Bioactive (Co)oligoesters as Potential Delivery Systems of p-Anisic Acid for Cosmetic Purposes

et al. 2020

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This article reports the studies on bioactive (co)oligoesters towards their use as controlled delivery systems of p-anisic acid. The objects of the study were oligo[3-hydroxy-3-(4-methoxybenzoyloxymethyl)propionate], (p-AA-CH2-HP)n oligoester, and oligo[(3-hydroxy-3-(4-methoxybenzoyloxymethyl)propionate)-co-(3-hydroxybutyrate)] [(p-AA-CH2-HP)x-co-(HB)y (co)oligoesters containing p-anisic acid moiety (p-AA, as the bioactive end and side groups) connected to the polymer backbone through the susceptible to hydrolysis ester bonds. A thorough insight into the hydrolysis process of the bioactive (co)oligoesters studied has allowed us to determine the release profile of p-AA as well as to identify polymer carrier degradation products. The p-AA release profiles determined on the basis of high-performance liquid chromatography (HPLC) measurements showed that the release of the bioactive compound from the developed (co)oligoester systems was regular and no burst effect occurred. Biological studies demonstrated that studied (homo)- and (co)oligoesters were well tolerated by HaCaT cells because none of them showed notable cytotoxicity. They promoted keratinocyte growth at moderate concentrations. Bioactive (co)oligoesters containing p-anisic acid moiety had somewhat decreased cell proliferation at the highest concentration (100 µg/mL). The important practical inference of the current study is that the (co)oligoesters developed have a relatively large load of the biologically active substance (p-AA) per polymer macromolecule, which unlocks their potential application in the cosmetic industry.

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Biological Evaluation and In Silico Study of Benzoic Acid Derivatives from Bjerkandera adusta Targeting Proteostasis Network Modules

Cited by 15 publications

References 60 publications

Molecular interactions of some phenolics with 2019-nCoV and related pathway elements

Molecular interactions of some phenolics with 2019-nCoV and related pathway elements

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

Bioactive (Co)oligoesters as Potential Delivery Systems of p-Anisic Acid for Cosmetic Purposes

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