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Oxime derivatives with larvicidal activity against Aedes aegypti L.

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Abstract

Oximes containing secondary metabolites constitute an important group of bioactive compounds and have been described and frequently updated in the literature due to their pharmacological properties. Thus, the aim of this study was to evaluate the larvicidal activity of a series of fourteen structurally related [1,4]-Benzoquinone mono-oximes on third-instar Aedes aegypti larvae and to investigate structure-activity relationships (SAR) of these compounds. Results of larvicidal assay revealed that all oximes were found to have larvicidal activity. Compound 2,6-dimethyl-[1,4]-benzoquinone oxime tosylate (11) was the most bioactive (LC50 = 9.858 ppm), followed by 2-methyl-[1,4]-benzoquinone oxime tosylate (9) (LC50 = 14.450 ppm). [1,4]-benzoquinone oxime (1) exhibited the lowest potency, with an LC50 = 121.181 ppm. The molecular characteristics which may help to understand the assayed compounds larvicidal activity were identified. SAR indicates that the addition of alkyl groups attached to the ring, number, position in the unsaturated cyclic structure, and size of these groups influence the larvicidal activity. Moreover, the lipophilicity seems to play an important role in increasing the larvicidal effect, because, in general, tosyl-containing products were more potent than products containing free OH.

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References

  • Abbott WS (1925) A method for computing the effectiveness of insecticides. J Econ Entomol 18:265–267

    Article  CAS  Google Scholar 

  • Aliyu HD (2007) Studies of pesticidal properties of tosyl 1,2-propanediol and ethanolamine. J Chem Soc Nigeria 32(2):292–294

    CAS  Google Scholar 

  • Aliyu HD (2008) Studies of pesticidal properties of tosyl-p-amino phenol and -p-nitro phenol. Internet J Toxicol 5(2)

  • Cafferata ML, Bardach A, Rey-Ares L, Alcaraz A, Cormick G, Gibbons L, Romano M, Cesaroni S, Ruvinsky S (2013) Dengue epidemiology and burden of disease in Latin America and the Caribbean: a systematic review of the literature and meta-analysis. Value Health Reg Issues 2:347–356

    Article  Google Scholar 

  • Cheng SS, Huang CG, Chen WJ, Kuo YH, Chang ST (2008) Larvicidal activity of tectoquinone isolated from red heartwood-type Cryptomeria japonica against two mosquito species. Bioresour Technol 99:3617–3622

    Article  CAS  PubMed  Google Scholar 

  • De Sousa DP, Schefer RR, Brocksom U, Brocksom TJ (2006) Synthesis and antidepressant evaluation of three para-benzoquinone mono-oximes and their oxy derivatives. Molecules 11:148–155

    Article  PubMed  Google Scholar 

  • De Sousa DP, Vieira YW, Uliana MP, Melo MA, Brocksom TJ, Cavalcanti SCH (2010) Larvicidal activity of para-benzoquinones. Parasitol Res 107:41–45

    Google Scholar 

  • Dias CN, Moraes DFC (2014) Essential oils and their compounds as Aedes aegypti L. Diptera: Culicidae) larvicides: review. Parasitol Res 113:565–592

    Article  PubMed  Google Scholar 

  • Finney DJ (1971) Probit analysis, 3rd edn. University Press, Cambridge

    Google Scholar 

  • García M, Donadel OJ, Ardanaz CE, Tonn CE, Sousa ME (2005) Toxic and repellent effects of Baccharis salicifolia essential oil on Tribolium castaneum. Pest Manag Sci 61:612–618

    Article  PubMed  Google Scholar 

  • Karakurt A, Dalkara S, Ozalp M, Ozbey S, Kendi E, Stables JP (2001) Synthesis of some 1-(2-naphthyl)-2-(imidazole-1-yl)ethanone oxime and oxime ether derivatives and their anticonvulsant and antimicrobial activities. Eur J Med Chem 36(5):421–433

    Article  CAS  PubMed  Google Scholar 

  • Kiprono CP, Midiwo JO, Kipkemboi PK, Ladogana S (2004) Larvicidal benzoquinone from Embelia schimperi. Bull Chem Soc Ethiop 18:45–49

    CAS  Google Scholar 

  • Li Y, Li C, Zheng Y, Wei X, Ma Q, Wei P, Liu Y, Qin Y, Yang N, Sun Y (2014) Design, synthesis, acaricidal activity, and mechanism of oxazoline derivatives containing an oxime ether moiety. J Agric Food Chem 30(14):3064–3072

    Article  Google Scholar 

  • Lima TC, da Silva TK, Silva FL, Barbosa-Filho JM, Marques MO, Santos RL, Cavalcanti SCH, de Sousa DP (2014) Larvicidal activity of Mentha × villosa Hudson essential oil, rotundifolone and derivatives. Chemosphere 104:37–43

    Article  CAS  PubMed  Google Scholar 

  • Lopez O, Fernandez-Bolanos JG, Gil MV (2005) New trends in pest control: the search for greener insecticides. Green Chem 7:431–442

    Article  CAS  Google Scholar 

  • Lucia A, Zerba E, Masuh H (2013) Knockdown and larvicidal activity of six monoterpenes against Aedes aegypti (Diptera: Culicidae) and their structure-activity relationships. Parasitol Res 112:4267–4272

    Article  PubMed  Google Scholar 

  • Mathew N, Subramanian S, Kalyanasundaram M (1996) Quantitative structure-activity relationship studies in pyrethroid esters derived from substituted 3-methyl-2-phenoxybutanoic acids, against Culex quinquefasciatus. Ind J Chem Sect B 35B(1):40–44

    CAS  Google Scholar 

  • Michaelakis A, Strongilos AT, Bouzas EA, Koliopoulos G, Couladouros EA (2009) Larvicidal activity of naturally occurring naphthoquinones and derivatives against the West Nile virus vector Culex pipiens. Parasitol Res 104(3):657–662

    Article  PubMed  Google Scholar 

  • Morimoto M, Tanimoto K, Sakatani A, Komai K (2002) Antifeedant activity of an anthraquinone aldehyde in Galium aparine L. against Spodoptera litura F. Phytochemistry 60:163–166

    Article  CAS  PubMed  Google Scholar 

  • Norris RK, Sternhell S (1969) 2-Substituted and 2,6-disubstituted 1,4-benzoquinone 4-oximes (‘p-nitrosophenols’). Aust J Chem 22(5):935–970

    Article  CAS  Google Scholar 

  • Pan American Health Organization (2014) Statistics and maps: dengue. Disponible:http://www.paho.org/hq/index.php?option=com_content&view=article&id=4494&Itemid=40687&lang=en. Accessed in October, 2014

  • Praba GO, Velmurugan D (2007) Quantitative structure-activity relationship of some pesticides. Indian J Biochem Biophys 44:470–476

    CAS  PubMed  Google Scholar 

  • Rodrigues AMS, de Paula JE, Roblot F, Fournet A, Espindola LS (2005) Larvicidal activity of Cybistax antisyphilitica against Aedes aegypti larvae. Fitoterapia 76(7-8):755–757

    Article  CAS  PubMed  Google Scholar 

  • Santos SRL, Silva VB, Melo MA, Barbosa JDF, Santos RLC, De Sousa DP, Cavalcanti SCH (2010) Toxic effects on and structure-toxicity relationships of phenylpropanoids, terpenes, and related compounds in Aedes aegypti larvae. Vector-Borne Zoon Dis 10:1049–1054

    Article  Google Scholar 

  • Santos SRL, Melo MA, Cardoso AV, Santos RLC, De Sousa DP, Cavalcanti SCH (2011) Structure-activity relationships of larvicidal monoterpenes and derivatives against Aedes aegypti Linn. Chemosphere 84(1):150–153

    Article  CAS  PubMed  Google Scholar 

  • Schenone S, Bruno O, Ranise A, Bondavalli F, Filippelli W, Falcone G, Rinaldi B (2000) O-[2-hydroxy-3-(dialkylamino)propyl]ethers of (+)-1,7,7-trimethyl bicyclo[2.2.1]heptan-2-one oxime (camphor oxime) with analgesic and antiarrhythmic activities. Farmaco 55(6-7):495–498

    Article  CAS  PubMed  Google Scholar 

  • Silva FC, Barros FMC, Prophiro JS, Silva OS, Pereira TN, Bordignon SAL, Eifler-Lima VL, von Poser GL (2013) Larvicidal activity of lipophilic extract of Hypericum carinatum (Clusiaceae) against Aedes aegypti (Diptera: Culicidae) and benzophenones determination. Parasitol Res 112:2367–2371

    Article  PubMed  Google Scholar 

  • Soga S, Sharma SV, Shiotsu Y, Shimizu M, Tahara H, Yamaguchi K, Ikuina Y, Murakata C, Tamaoki T, Kurebayashi J, Schulte TW, Neckers LM, Akinaga S (2001) Stereospecific antitumor activity of radicicol oxime derivatives. Cancer Chem Pharmacol 48(6):435–445

    Article  CAS  Google Scholar 

  • Sun R, Lu M, Chen L, Li Q, Song H, Bi F, Huang R, Wang Q (2008) Design, synthesis, bioactivity, and structure-activity relationship (SAR) studies of novel benzoylphenylureas containing oxime ether group. J Agric Food Chem 56(23):11376–11391

    Article  CAS  PubMed  Google Scholar 

  • Sun R, Li Y, Lue M, Xiong L, Wang Q (2010) Synthesis, larvicidal activity, and SAR studies of new benzoylphenylureas containing oxime ether and oxime ester group. Bioorg Med Chem Lett 20(15):4693–4699

    Article  CAS  PubMed  Google Scholar 

  • Torres RC, Garbo AG, Walde RZML (2014) Larvicidal activity of Persea americana Mill. against Aedes aegypti. Asian Pac J Trop Med 7(1):S167–S170

    Article  CAS  Google Scholar 

  • Yang YC, Lim MY, Lee HS (2003) Emodin isolated from Cassia obtusifolia (Leguminosae) seed shows larvicidal activity against three mosquito species. J Agric Food Chem 51:7629–7631

    Article  CAS  PubMed  Google Scholar 

  • Zahran HEM, Abdelgaleil SAM (2011) Insecticidal and developmental inhibitory properties of monoterpenes on Culex pipiens L. (Diptera: Culicidae). J Asia Pac Entomol 14:46–51

    Article  CAS  Google Scholar 

  • Zareen F, Muhammad I, Mohammad AB, Zarfishan T, Obaid U, Muhammad QZ, Abrar H, Madiha A, Bushra K, Samia A, Saira M, Sana S, Bisma R, Sadaf B, Mahrukh N, Sadia B, Mahwish A, Liaqat A, Muhammad A (2011) Serotype and genotype analysis of dengue virus by sequencing followed by phylogenetic analysis using samples from three mini-outbreaks 2007-2009 in Pakistan. BMC Microbiol 11:1–8

    Article  Google Scholar 

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Acknowledgements

The authors thank the CAPES, CNPq, Federal University of Sergipe, and Federal University of Paraíba for the financial support.

Conflict of interest

We declare that we have no conflict of interest.

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Authors and Affiliations

  1. Department of Pharmacy, Federal University of Sergipe, São Cristóvão, Sergipe, 49100-000, Brazil

    Tamires Cardoso Lima, Sandra Regina Lima Santos, Roseli La Corte Santos & Sócrates Cabral de Holanda Cavalcanti

  2. Laboratory of Bioorganic Chemistry, Department of Chemisty, Federal University of São Carlos, Postal code 676, São Carlos, SP, 13565-905, Brazil

    Marciana P. Uliana & Timothy John Brocksom

  3. Department of Pharmaceutical Sciences, Federal University of Paraíba, João Pessoa, Paraíba, 58051-970, Brazil

    Damião Pergentino de Sousa

Authors
  1. Tamires Cardoso Lima
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  2. Sandra Regina Lima Santos
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  3. Marciana P. Uliana
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  4. Roseli La Corte Santos
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  5. Timothy John Brocksom
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  6. Sócrates Cabral de Holanda Cavalcanti
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  7. Damião Pergentino de Sousa
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Correspondence to Damião Pergentino de Sousa.

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Lima, T.C., Santos, S.R.L., Uliana, M.P. et al. Oxime derivatives with larvicidal activity against Aedes aegypti L.. Parasitol Res 114, 2883–2891 (2015). https://doi.org/10.1007/s00436-015-4489-9

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  • DOI: https://doi.org/10.1007/s00436-015-4489-9

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