4.5 Article

Synthesis of Eugenol Derivatives and Evaluation of their Antifungal Activity Against Fusarium solani f. sp. piperis

期刊

CURRENT PHARMACEUTICAL DESIGN
卷 26, 期 14, 页码 1532-1542

出版社

BENTHAM SCIENCE PUBL LTD
DOI: 10.2174/1381612826666200403120448

关键词

Antifiugal; eugenol derivatives; cytotoxicity; Piper nigrum; Fusarium solani f. sp. piperis; macrophages

资金

  1. Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior - Brasil (CAPES) [001]
  2. National Council of Scientific and Technological Development - CNPq
  3. Foundation of Support to Research and Innovation of Espirito Santo (FAPES PPE-Agro) [76418880/16, 76419363/16]
  4. CAPES
  5. INCTBioNat [CNPq 465637/2014-0]
  6. NCQP-UFES

向作者/读者索取更多资源

Background: Fusarium solani f. sp. piperis is a phytopathogen that causes one of the most destructive diseases in black pepper crops, resulting in significant economic and crop production losses. Consequently, the control of this fungal disease is a matter of current and relevant interest in agriculture. Objective: The objective was to synthesize eugenol derivatives with antifungal activity. Methods: In this study, using bimolecular nucleophilic substitution and click chemistry approaches, four new and three known eugenol derivatives were obtained. The eugenol derivatives were characterized and their antifungal and cytotoxic effects were evaluated. Results: Eugenol derivative 4 (2-(4-allyl-2-methoxyphenoxy)-3-chloronaphthalene-1,4-dione) was the most active against F. solani f. sp. piperis and showed acceptable cytotoxicity. Compound 4 was two-fold more effective than tebuconazole in an antifungal assay and presented similar cytotoxicity in macrophages. The in silico study of beta-glucosidase suggests a potential interaction of 4 with amino acid residues by a cation-pi interaction with residue Arg(177) followed by a hydrogen bond with Glu(596), indicating an important role in the interactions with 4, justifying the antifungal action of this compound. In addition, the cytotoxicity after metabolism was evaluated as a mimic assay with the S9 fraction in HepG2 cells. Compound 4 demonstrated maintenance of cytotoxicity, showing IC50 values of 11.18 +/- 0.5 and 9.04 +/- 0.2 mu g mL(-)(1) without and with the S9 fraction, respectively. In contrast, eugenol (257.9 +/- 0.4 and 133.5 +/- 0.8 mu g mL(-1)), tebuconazole (34.94 +/- 0.2 and 26.76 +/- 0.17 mu g mL(-1)) and especially carbendazim (251.0 +/- 0.30 and 34.7 +/- 0.10 mu g mL(-1)) showed greater cytotoxicity after hepatic biotransformation. Conclusion: The results suggest that 4 is a potential candidate for use in the design of new and effective compounds that could control this pathogen.

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