Natural compounds isolated from Brazilian plants are potent inhibitors of hepatitis C virus replication in vitro

Jardim, Ana Carolina Gomes; Iglói, Zsófia; Shimizu, Jacqueline Farinha; Santos, Vânia Aparecida de Freitas Formenton Macedo dos; Felippe, Lidiane Gaspareto; Mazzeu, Bruna Fonseca; Amako, Yutaka; Furlan, Maysa; Harris, Mark; Rahal, Paula

doi:10.1016/j.antiviral.2014.12.018

Cited by 36 publications

(31 citation statements)

References 45 publications

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“…The known compounds were identified as (E)-4-methoxy-6-styryl-2H-pyran-2-one (1), 25,26,31 4-methoxy-6-(3-phenyloxiran-2-yl)-2H-pyran-2-one (2), 6-(1,2-dihydroxy-2-phenylethyl)-4-methoxy-2H-pyran-2-one (3), 24 methyl-4-methoxy-3-(3'-methyl-2'-butenyl) benzoate (4) 32,33 and methyl 2,2-dimethyl-4-oxochroman-6-carboxylate (5) by NMR and/or by HRMS (Supplementary Information) as well as by comparison with the literature data. 13,14,24,34,35 The molecular formula of 6 was established as C 14 C NMR data corroborated the substituents of aromatic ring, and all signals were assigned accordingly based on the gHMBC data (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…[27][28][29][30] This species was previously found to contain the kavalactone demethoxy-yagonin ((E)-4-methoxy-6-styryl-2H-pyran-2-one (1)), which showed inhibitory activity towards hepatitis C virus replication. 31 In addition to 1, we also report the isolation of two kavalactones from P. fuligineum leaves, 4-methoxy-6-(3-phenyloxiran-2-yl)-2H-pyran-2-one (2) and 6-(1,2-dihydroxy-2-phenylethyl)-4-methoxy-2H-pyran-2-one (3), as well as three benzoic acid derivatives, methyl-4-methoxy-3-(3'-methyl-2'-butenyl) benzoate (4), methyl 2,2-dimethyl-4-oxochroman-6-carboxylate (5), and methyl 4-methoxy-3-(3-methylbut-2-enoyl)benzoate (6). Compounds 1-5 were previously isolated from Piper species, but compound 6 is, to the best of our knowledge, a new natural product.…”

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confidence: 99%

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Kavalactones and Benzoic Acid Derivatives from Leaves of Piper fuligineum Kunth (Piperaceae)

Mazzeu¹,

Felippe²,

Cotinguiba³

et al. 2017

J. Braz. Chem. Soc.

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The known kavalactones (E)-4-methoxy-6-styryl-2H-pyran-2-one, 4-methoxy-6-(3-phenyloxiran-2-yl)-2H-pyran-2-one, 6-(1,2-dihydroxy-2-phenylethyl)-4-methoxy-2H-pyran-2-one, the three benzoic acid derivatives methyl-4-methoxy-3-(3'-methyl-2'-butenyl)benzoate and methyl 2,2-dimethyl-4-oxochroman-6-carboxylate, and a new methyl 4-methoxy-3-(3-methylbut-2-enoyl)benzoate were isolated from the ethanolic extract of Piper fuligineum. The structures of these compounds were determined by using a combination of spectroscopic methods, including 1D-and 2D-nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. This is the first report of the chemical study of P. fuligineum, and the methyl 4-methoxy-3-(3-methylbut-2-enoyl)benzoate is described as a new natural product.

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Kavalactones and Benzoic Acid Derivatives from Leaves of Piper fuligineum Kunth (Piperaceae)

Mazzeu¹,

Felippe²,

Cotinguiba³

et al. 2017

J. Braz. Chem. Soc.

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“…Among them, antiviral research based on natural molecules is a potential approach. Many natural compounds showed antiviral activity against a variety of human viruses such as dengue (DENV) [22][23][24][25], yellow fever (YFV) [25][26][27], hepatitis C (HCV) [28][29][30][31][32], influenza [33,34], and zika (ZIKV) [33,35,36]. Here, we aim to summarize the natural compounds previously described to possess anti-CHIKV activity ( Table 1).…”

Section: Epigallocatechin Gallate (Green Tea)mentioning

confidence: 99%

Antivirals Against Chikungunya Virus: Is the Solution in Nature?

Martins

Santos

Oliveira

et al. 2020

Viruses

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The worldwide outbreaks of the chikungunya virus (CHIKV) in the last years demonstrated the need for studies to screen antivirals against CHIKV. The virus was first isolated in Tanzania in 1952 and was responsible for outbreaks in Africa and Southwest Asia in subsequent years. Between 2007 and 2014, some cases were documented in Europe and America. The infection is associated with low rates of death; however, it can progress to a chronic disease characterized by severe arthralgias in infected patients. This infection is also associated with Guillain-Barré syndrome. There is no specific antivirus against CHIKV. Treatment of infected patients is palliative and based on analgesics and non-steroidal anti-inflammatory drugs to reduce arthralgias. Several natural molecules have been described as antiviruses against viruses such as dengue, yellow fever, hepatitis C, and influenza. This review aims to summarize the natural compounds that have demonstrated antiviral activity against chikungunya virus in vitro.Viruses 2020, 12, 272 2 of 17 CHIKV belongs to the Alphavirus genus and the Togaviridae family. It is a positive-sense, single-stranded RNA (12 kb in length) virus, with an enveloped icosahedral capsid [10]. The virus lifecycle starts via the attachment of the viral glycoproteins to the cell membrane receptors, mainly to MXRA8 [11,12] but also to prohibitin (PHB) [13], phosphatidylserine (PtdSer) [14], and glycosaminoglycans (GAGs) [15] receptors in mammalian and to ATP synthase β in mosquito cells [16], forming a pore. Then, a virus capsid is released into the cytoplasm, where the replication process takes place. Viral genome is uncoated and directly translated into nonstructural (NS) proteins nP1-4. The NS proteins form the viral replicase complex that catalyzes the synthesis of a negative strand, a template to synthesize the full-length positive sense genome, and the subgenomic mRNA. The subgenomic mRNA is translated in a polyprotein, which is cleaved to produce the structural proteins C, E3, E2, 6k, and E1, followed by the assembly of the viral components and virus release (Figure 1) [17,18].

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“…During the past several decades a great deal of research has been invested natural products from medicinal plants due to the advantages of lower cost, fewer adverse effects, and high chemical diversity of these biologically active molecules. Many plant phytochemicals, such as flavonoids, terpenoids, lignin, alkaloids, tannins, polyphenolics, coumarins, saponins, and chlorophyllins, are reported to have anti-HCV activity (18)(19)(20)(21)(22)(23)(24)(25)(26). Thus, natural products from medicinal plants represent an alternative approach to controlling HCV infections.…”

Section: Introductionmentioning

confidence: 99%

Anti-Hepatitis C Virus Activity of a Crude Extract from Longan (<i>Dimocarpus longan</i> Lour.) Leaves

et al. 2016

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SUMMARY:Infection with hepatitis C virus (HCV) results in hepatitis C, a disease characterized by chronic infection, cirrhosis, and hepatocellular carcinoma. Currently, the standard therapy is a combination of pegylated interferon-a plus ribavirin with NS3 protease inhibitors. Addition of NS3 protease inhibitors to the standard therapy improves response rates; however, use of NS3 protease inhibitors is also associated with significant adverse effects and an increase in the overall cost of treatment. Therefore, there is a need to develop safe and inexpensive drugs for the treatment of HCV infections. In this study, we examined the antiviral activity of a crude extract from Dimocarpus longan leaves against HCV (genotype 2a strain JFH1). The D. longan crude extract (DL-CE) exhibited anti-HCV activity with a 50z effective concentration (EC 50 ) of 19.4 mg/ml without cytotoxicity. A time-of-addition study demonstrated that DL-CE has anti-HCV activity at both the entry and post-entry steps and markedly blocks the viral entry step through direct virucidal activity with marginal inhibition of virion assembly. Co-treatment of DL-CE with cyclosporine A, an immunosuppressant or telaprevir, an NS3 protease inhibitor, resulted in additive and synergistic antiviral effects, respectively. Our findings suggest that DL-CE may be useful as an add-on therapy candidate for treating HCV infections.

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Natural compounds isolated from Brazilian plants are potent inhibitors of hepatitis C virus replication in vitro

Cited by 36 publications

References 45 publications

Kavalactones and Benzoic Acid Derivatives from Leaves of Piper fuligineum Kunth (Piperaceae)

Kavalactones and Benzoic Acid Derivatives from Leaves of Piper fuligineum Kunth (Piperaceae)

Antivirals Against Chikungunya Virus: Is the Solution in Nature?

Anti-Hepatitis C Virus Activity of a Crude Extract from Longan (<i>Dimocarpus longan</i> Lour.) Leaves

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