BACKGROUND: Dengue fever is a severe public health problem for several countries. In order to find effective larvicides to aid control programs, the structure-activity relationships of eugenol derivatives against Aedes aegypti (Diptera: Culicidae) larvae were evaluated. Additionally, the composition and larvicidal activity of Syzygium aromaticum essential oil was assessed. RESULTS: Four compounds representing 99.05% of S. aromaticum essential oil have been identified. The essential oil was active against Ae. aegypti larvae (LC(50) = 62.3 and 77.0 ppm, field-collected and Rockefeller larvae respectively). The larvicidal activity of eugenol, the major compound of the essential oil, was further evaluated (LC(50) = 93.3 and 71.9 ppm, field-collected and Rockefeller larvae respectively). The larvicidal activity and structure-activity relationships of synthetic derivatives of eugenol were also assessed. The larvicidal activity of the derivatives varied between 62.3 and 1614.9 ppm. Oxidation of eugenol allylic bond to a primary alcohol and removal of the phenolic proton resulted in decreased potency. However, oxidation of the same double bond in 1-benzoate-2-methoxy-4-(2-propen-1-yl)-phenol resulted in increased potency. CONCLUSION: Structural characteristics were identified that may contribute to the understanding of the larvicidal activity of phenylpropanoids. The present approach may help future work in the search for larvicidal compounds.
BACKGROUND:Dengue fever is a severe public health problem for several countries. In order to find effective larvicides to aid control programs, the structure-activity relationships of eugenol derivatives against Aedes aegypti (Diptera: Culicidae) larvae were evaluated. Additionally, the composition and larvicidal activity of Syzygium aromaticum essential oil was assessed. RESULTS: Four compounds representing 99.05% of S. aromaticum essential oil have been identified. The essential oil was active against Ae. aegypti larvae (LC(50) = 62.3 and 77.0 ppm, field-collected and Rockefeller larvae respectively). The larvicidal activity of eugenol, the major compound of the essential oil, was further evaluated (LC(50) = 93.3 and 71.9 ppm, field-collected and Rockefeller larvae respectively). The larvicidal activity and structure-activity relationships of synthetic derivatives of eugenol were also assessed. The larvicidal activity of the derivatives varied between 62.3 and 1614.9 ppm. Oxidation of eugenol allylic bond to a primary alcohol and removal of the phenolic proton resulted in decreased potency. However, oxidation of the same double bond in 1-benzoate-2-methoxy-4-(2-propen-1-yl)-phenol resulted in increased potency. CONCLUSION: Structural characteristics were identified that may contribute to the understanding of the larvicidal activity of phenylpropanoids. The present approach may help future work in the search for larvicidal compounds.
Authors: Ângela C F Costa; Sócrates C H Cavalcanti; Alisson S Santana; Ana P S Lima; Thaysnara B Brito; Rafael R B Oliveira; Nathália A Macêdo; Paulo F Cristaldo; Ana Paula A Araújo; Leandro Bacci Journal: Ecotoxicology Date: 2019-08-16 Impact factor: 2.823
Authors: Rafaela K V Nunes; Ulisses N Martins; Thaysnara B Brito; Angelita Nepel; Emmanoel V Costa; Andersson Barison; Roseli L C Santos; Sócrates C H Cavalcanti Journal: Environ Sci Pollut Res Int Date: 2018-09-05 Impact factor: 4.223
Authors: Athanasios C Kimbaris; George Koliopoulos; Antonios Michaelakis; Maria A Konstantopoulou Journal: Parasitol Res Date: 2012-09-06 Impact factor: 2.289
Authors: Adriana Faraco de Oliveira Araujo; João Tadeu Ribeiro-Paes; Juliana Telles de Deus; Sócrates Cabral de Holanda Cavalcanti; Rogéria de Souza Nunes; Péricles Barreto Alves; Maria de Lourdes da Graça Macoris Journal: Mem Inst Oswaldo Cruz Date: 2016-07-04 Impact factor: 2.743