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Larvicidal activity of lansiumamide B from the seeds of Clausena lansium against Aedes albopictus (Diptera: Culicidae)

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Abstract

The larvicidal activity of crude petroleum ether, toluene, n-butanol, ethyl acetate, acetone, and methanol extracts of the seeds of Clausena lansium was assayed for their toxicities against the early fourth instar larvae of Aedes albopictus. The larval mortality was observed after 24-h exposure. The LC50 value of petroleum ether extract was 22.99 ppm, showing the best larvicidal activity among all six solvent extracts. A cinnamon amide compound lansiumamide B (N-methyl-N-cis-styrylcinnamamide) was isolated from the petroleum ether extract by column chromatographic method, which exhibited a strong larvicidal activity against the early fourth instar larvae of A. albopictus with LC50 and LC90 values of 0.45 and 2.19 ppm, respectively. The structure was elucidated by 1H NMR, 13C NMR spectral data. The larvicidal activity against mosquito of lansiumamide B from the seed of C. lansium was evaluated for the first time.

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References

  • Abou-Elnaga ZS, Alarif WM, Al-lihaibi SS (2011) New larvicidal acetogenin from the red alga Laurencia papillosa. Clean-Soil Air Water 39:787–794

    Article  CAS  Google Scholar 

  • Batabyal L, Sharma P, Mohan L, Maurya P, Srivastava CN (2009) Relative toxicity of neem fruit, bitter gourd, and castor seed extracts against the larvae of filaria vector, Culex quinquefasciatus (Say). Parasitol Res 105:1205–1210

    Article  PubMed  Google Scholar 

  • Bayer A, Maier ME (2004) Synthesis of enamides from aldehydes and amides. Tetrahedron 60(31):6665–6677

    Article  CAS  Google Scholar 

  • Chung IM, Song HK, Yeo MA, Moon HI (2011a) Composition and immunotoxicity activity of major essential oils from stems of Allium victorialis L. var. platyphyllum Makino against Aedes aegypti L. Immunopharmacol Immunotoxicol 33:480–483

    Article  PubMed  CAS  Google Scholar 

  • Chung IM, Kim SJ, Yeo MA, Park SW, Moon HI (2011b) Immunotoxicity activity of natural furocoumarins from milky sap of Ficus carica L. against Aedes aegypti L. Immunopharmacol Immunotoxicol 33(3):515–518

    Article  PubMed  CAS  Google Scholar 

  • Enserink M (2008) A mosquito goes global. Science 320:864–866

    Google Scholar 

  • Fan GJ, Han BH, Kang YH, Park MK (2001) Evaluation of inhibitory potentials of Chinese medicinal plants on platelet-activating factor (PAF) receptor binding. Nat Prod Sci 7:33–37

    CAS  Google Scholar 

  • Ho JC (2011) Antimicrobial, mosquito larvicidal and antioxidant properties of the leaf and rhizome of Hedychium coronarium. J Chin Chem Soc 58:563–567

    Article  CAS  Google Scholar 

  • James AA (1992) Mosquito molecular genetics: the hands that feed bite back. Science 257(5066):37–38

    Article  PubMed  CAS  Google Scholar 

  • Kalaivani K, Senthil-Nathan S, Murugesan AG (2011) Biological activity of selected Lamiaceae and Zingiberaceae plant essential oils against the dengue vector Aedes aegypti L. (Diptera: Culicidae). Parasitol Res 110:1261–1268

    Article  PubMed  Google Scholar 

  • Kamaraj C, Bagavan A, Rahuman AA, Zahir AA, Elango G, Pandiyan G (2009) Larvicidal potential of medicinal plant extracts against Anopheles subpictus Grassi and Culex tritaeniorhynchus Giles (Diptera: Culicidae). Parasitol Res 104:1163–1171

    Article  PubMed  CAS  Google Scholar 

  • Kannathasan K, Senthilkumar A, Venkatesalu V (2011) Mosquito larvicidal activity of methyl-p-hydroxybenzoate isolated from the leaves of Vitex trifolia Linn. Acta Trop 120:115–118

    Article  PubMed  CAS  Google Scholar 

  • Khanna VG, Kannabiran K, Rajakumar G, Rahuman AA, Santhoshkumar T (2011) Biolarvicidal compound gymnemagenol isolated from leaf extract of miracle fruit plant, Gymnema sylvestre (Retz) Schult against malaria and filariasis vectors. Parasitol Res 109:1373–1386

    Article  PubMed  Google Scholar 

  • Kovendan K, Murugan K, Vincent S (2011a) Evaluation of larvicidal activity of Acalypha alnifolia Kleinex Willd. (Euphorbiaceae) leaf extract against the malaria vector, Anopheles stephensi, dengue vector, Aedes aegypti and Bancroftian filariasis vector, Culex quinquefasciatus (Diptera: Culicidae). Parasitol Res 110:571–581

    Article  PubMed  Google Scholar 

  • Kovendan K, Murugan K, Vincent S, Kamalakannan S (2011b) Larvicidal efficacy of Jatropha curcas and bacterial insecticide, Bacillus thuringiensis, against lymphatic filarial vector, Culex quinquefasciatus Say (Diptera: Culicidae). Parasitol Res 109:1251–1257

    Article  PubMed  Google Scholar 

  • Kovendan K, Murugan K, Shanthakumar SP, Vincent S, Hwang JS (2012a) Larvicidal activity of Morinda citrifolia L. (Noni) (Family: Rubiaceae) leaf extract against Anopheles stephensi, Culex quinquefasciatus, and Aedes aegypti. Parasitol Res. doi:10.1007/s00436-012-2984-9

  • Kovendan K, Arivoli S, Maheshwaran R, Baskar K, Vincent S (2012b) Larvicidal efficacy of Sphaeranthus indicus, Cleistanthus collinus and Murraya koenigii leaf extracts against filarial vector, Culex quinquefasciatus Say (Diptera: Culicidae). Parasitol Res. doi:10.1007/s00436-012-2927-5

  • Kumar V, Vallipuram K, Adebajo AC, Reisch J (1995) 2, 7-dihydroxy-3-formyl-1-(3′-methyl-2′-butenyl) carbazole from Clausena lansium. Phytochemistry 40:1563–1565

    Article  CAS  Google Scholar 

  • Kumar S, Warikoo R, Wahab N (2010) Larvicidal potential of ethanolic extracts of dried fruits of three species of peppercorns against different instars of an Indian strain of dengue fever mosquito, Aedes aegypti L. (Diptera: Culicidae). Parasitol Res 107:901–907

    Article  PubMed  Google Scholar 

  • Kumar S, Singh AP, Nair G, Batra S, Seth A, Wahab N, Warikoo R (2011) Impact of Parthenium hysterophorus leaf extracts on the fecundity, fertility and behavioural response of Aedes aegypti L. Parasitol Res 108:853–859

    Article  PubMed  Google Scholar 

  • Kumar PM, Murugan K, Kovendan K, Panneerselvam C, Kumar KP, Amerasan D, Subramaniam J, Kalimuthu K, Nataraj T (2012) Mosquitocidal activity of Solanum xanthocarpum fruit extract and copepod Mesocyclops thermocyclopoides for the control of dengue vector Aedes aegypti. Parasitol Res 111:609–618

    Article  Google Scholar 

  • Lalrotluanga, Ngente L, Nachimuthu SK, Guruswami G (2012) Insecticidal and repellent activity of Hiptage benghalensis L. Kruz (Malpighiaceae) against mosquito vectors. Parasitol Res. doi:10.1007/s00436-012-2925-7

  • Li WS, James DM, Farouk SE (1991) Carbazole alkaloids from Clausena lansium. Phytochemistry 30:343–346

    Article  CAS  Google Scholar 

  • Lin JH (1989) Cinnamamide derivatives from Clausena lansium. Phytochemistry 28:621–622

    Article  CAS  Google Scholar 

  • Liu GT, Li WX, Chen YY, Wei HL (1996) Hepatoprotective action of nine constituents isolated from the leaves of Clausena lansium in mice. Drug Dev Res 39:174–178

    Article  CAS  Google Scholar 

  • Liu ZL, Liu QZ, Du SS, Deng ZW (2012) Mosquito larvicidal activity of alkaloids and limonoids derived from Evodia rutaecarpa unripe fruits against Aedes albopictus (Diptera: Culicidae). Parasitol Res. doi:10.1007/s00436-012-2923-9

  • Maneerat W, Tha-in S, Cheenpracha S, Prawat U, Laphookhieo S (2011) New amides from the seeds of Clausana lansium. J Med Plants Res 5:2812–2815

    CAS  Google Scholar 

  • Maurya P, Sharma P, Mohan L, Batabyal L, Srivastava CN (2009) Evaluation of larvicidal nature of fleshy fruit wall of Momordica charantia Linn. (family: cucurbitaceae) in the management of mosquitoes. Parasitol Res 105:1653–1659

    Article  PubMed  Google Scholar 

  • Moon HI, Cho SB, Lee JH, Paik HD, Kim SK (2011) Immunotoxicity activity of sesquiterpenoids from black galingale (Kaempferia parviflora Wall. Ex. Baker) against Aedes aegypti L. Immunopharmacol Immunotoxicol 33(2):380–383

    Article  PubMed  CAS  Google Scholar 

  • Murugan K, Kumar PM, Kovendan K, Amerasan D, Subrmaniam J, Hwang JS (2012) Larvicidal, pupicidal, repellent and adulticidal activity of Citrus sinensis orange peel extract against Anopheles stephensi, Aedes aegypti and Culex quinquefasciatus (Diptera: Culicidae). Parasitol Res. doi:10.1007/s00436-012-3021-8

  • Muthu C, Reegan AD, Kingsley S, Ignacimuthu S (2012) Larvicidal activity of pectolinaringenin from Clerodendrum phlomidis L. against Culex quinquefasciatus Say and Aedes aegypti L. (Diptera: Culicidae). Parasitol Res. doi:10.1007/s00436-012-2932-8

  • Ng TB, Lam SK, Fong WP (2003) A homodimeric sporamin-type trypsin inhibitor with antiproliferative, HIV reverse transcriptase-inhibitory and antifungal activities from wampee (Clausena lansium) seeds. Biol Chem 384:289–293

    PubMed  CAS  Google Scholar 

  • Peng HJ, Lai HB, Zhang QL, Xu BY, Zhang H, Lu WH, Zhao W, Zhou YP, Zhong XG, Jiang S, Duan JH, Yan GY, He JF, Chen XG (2012) A local outbreak of dengue caused by an imported case in Dongguan China. BMC Publ Health. doi:10.1186/1471-2458-12-83

  • Prasad KN, Hao J, Yi C, Zhang DD, Qiu SX, Jiang YM, Zhang MW, Chen F (2009) Antioxidant and anticancer activities of wampee (Clausena lansium (Lour.) Skeels) peel. J Biomed Biotechnol. doi:10.1155/2009/612805

  • Prophiro JS, Silva MN, Kanis LA, Silva BM, Duque-Luna JE, Silva OS (2012) Evaluation of time toxicity, residual effect, and growth-inhibiting property of Carapa guianensis and Copaifera sp. in Aedes aegypti. Parasitol Res 110:713–719

    Article  PubMed  Google Scholar 

  • Rahuman AA, Gopalakrishnan G, Venkatesan P, Geetha K (2008) Isolation and identification of mosquito larvicidal compound from Abutilon indicum (Linn.) Sweet. Parasitol Res 102:981–988

    Article  PubMed  Google Scholar 

  • Rahuman AA, Bagavan A, Kamaraj C, Vadivelu M, Zahir AA, Elango G, Pandiyan G (2009) Evaluation of indigenous plant extracts against larvae of Culex quinquefasciatus Say (Diptera: Culicidae). Parasitol Res 104:637–643

    Article  PubMed  Google Scholar 

  • Rawani A, Ghosh A, Chandra G (2010) Mosquito larvicidal activities of Solanum nigrum L. leaf extract against Culex quinquefasciatus Say. Parasitol Res 107:1235–1240

    Article  PubMed  Google Scholar 

  • Reddy PJ, Krishna D, Murthy US, Jamil K (1992) A microcomputer FORTRAN program for rapid determination of lethal concentration of biocides in mosquito control. CABIOS 8:209–213

    Google Scholar 

  • Sagnou M, Mitsopoulou KP, Koliopoulos G, Pelecanou M, Couladouros EA, Michaelakis A (2012) Evaluation of naturally occurring curcuminoids and related compounds against mosquito larvae. Acta Trop 123:190–195

    Article  PubMed  CAS  Google Scholar 

  • Senthilkumar A, Venkatesalu V (2010) Chemical composition and larvicidal activity of the essential oil of Plectranthus amboinicus (Lour.) Spreng against Anopheles stephensi: a malarial vector mosquito. Parasitol Res 107:1275–1278

    Article  PubMed  Google Scholar 

  • Shen ZF, Chen QM, Liu HF, Xie MZ (1989) The hypoglycemic effect of clausenacoumarine. Acta Pharm Sin 24:391–392

    CAS  Google Scholar 

  • Vinayachandra SR, Chandrashekar KR (2011) Larvicidal activities of Knema attenuata (Hook. f. & Thomson) Warb. (Myristicaceae) extracts against Aedes albopictus Skuse and Anopheles stephensi Liston. Parasitol Res 109:1671–1676

    Article  PubMed  CAS  Google Scholar 

  • Wang ZQ, Kim JR, Wang M, Shu SH, Ahn YJ (2012) Larvicidal activity of Cnidium monnieri fruit coumarins and structurally related compounds against insecticide-susceptible and insecticide-resistant Culex pipiens pallens and Aedes aegypti. Pest manag sci 68:1041–1047

    Article  PubMed  CAS  Google Scholar 

  • WHO (2009) Dengue—guidelines for diagnosis, treatment, prevention and control. WHO Press, World Health Organization, Geneva, pp 1–147, WHO/HTM/NTD/DEN/2009.1

    Google Scholar 

  • World Health Organization (1996) Report of the WHO informal consultation on the evaluation and testing of insecticides. CTD/WHO PES/IC/96.1. World Health Organization, Geneva, p 69

    Google Scholar 

  • Wu JD, He SC, Huang XS, Shen WZ (2010a) Effects of N-methyl-N-cis-styryl-cinnamamide on Penicillin-induced epileptiform discharges in rats. J Sun Yat-Sen Univ (Med Sci) 31(2):213–220

    CAS  Google Scholar 

  • Wu JY, Lun ZR, James AA, Chen XG (2010b) Dengue fever in mainland China. AmJTrop Med Hyg 83(3):664–671

    Article  Google Scholar 

  • Xiao XM, Hu ZN, Shi BJ, Wei SP, Wu WJ (2012) Larvicidal activity of lignans from Phryma leptostachya L. against Culex pipiens pallens. Parasitol Res 110:1079–1084

    Article  PubMed  Google Scholar 

  • Zhu L, Tian YJ (2011) Chemical composition and larvicidal activity of Blumea densiflora essential oils against Anopheles anthropophagus: a malarial vector mosquito. Parasitol Res 109:1417–1422

    Article  PubMed  Google Scholar 

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Acknowledgments

This work was supported by the Science and Technology Planning Project of Guangzhou (2010Y1-27). The authors are thankful to the Guangzhou Center for Disease Control and Prevention for providing the larvae of mosquito.

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Correspondence to Shu-qing Wan.

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Han, Y., Li, Lc., Hao, Wb. et al. Larvicidal activity of lansiumamide B from the seeds of Clausena lansium against Aedes albopictus (Diptera: Culicidae). Parasitol Res 112, 511–516 (2013). https://doi.org/10.1007/s00436-012-3161-x

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