Advertisement

Parasitology Research

, Volume 108, Issue 2, pp 297–304 | Cite as

In vitro isolation and characterization of biolarvicidal compounds from micropropagated plants of Spilanthes acmella

  • Vibha Pandey
  • Madhu Chopra
  • Veena Agrawal
Original Paper

Abstract

Spilanthes acmella (Family: Asteraceae) commonly known as “toothache plant” is known to possess strong insecticidal and larvicidal properties. Experiments have been conducted to isolate and characterise the biolarvicidal compounds from the flower head extract of micropropagated S. acmella plants employing various tools like FT-IR, TLC, CC, NMR. FT-IR spectroscopy of the crude hexane extract sample revealed the presence of amide (secondary metabolite) as functional group in S. acmella flower heads. The crude extract was separated into 85 fractions (100 ml each) through silica gel column chromatography using hexane-ethyl acetate mobile phase. All fractions were tested for their larvicidal activity against late III/early IV instar Anopheles stephensi larvae and fraction showing maximum bioefficacy against aforesaid larvae was further resolved into three separate bands on Preparative TLC plate, the respective Rf values being (a) 0.18, (b) 0.23 and (c) 0.27. Based on Proton NMR spectrum of the eluted compounds and their comparison with published results, three different compounds were identified: N-isobutyl-2,6,8-decatrienamide (compound 1), undeca-2E,7Z,9E-trienoic acid isobutylamide (compound 2) from band a and (2E)-N-(2-methylbutyl)-2-undecene-8,10-diynamide (compound 3) from band b. The amount of the compounds obtained were 338 mg (compounds 1 and 2) and 188.4 mg (compound 3), respectively. This is the first report of biolarvicidal compounds isolation and characterisation from micropropagated S. acmella plants.

Keywords

Malaria Crude Extract Larvicidal Activity Flower Head Micropropagated Plant 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Abbreviations

FT-IR

Fourier transform infrared spectroscopy

TLC

Thin-layer chromatography

CC

Column chromatography

NMR

Nuclear magnetic resonance

Prep-TLC

Preparative thin-layer chromatography

Notes

Acknowledgements

Veena Agrawal is grateful to University Grants Commission, New Delhi for financial assistance and Vibha Pandey to CSIR, New Delhi for JRF and SRF. Thanks are also due to Dr. A.P. Dash and Dr. K. Raghavendra, National Institute of Malaria Research, Delhi for kindly providing us the mosquito larvae for bioassay tests.

References

  1. Amer A, Mehlhorn H (2006a) Repellency effect of 41 essential oils against Aedes, Anopheles, and Culex mosquitoes. Parasitol Res 99:478–490CrossRefPubMedGoogle Scholar
  2. Amer A, Mehlhorn H (2006b) The sensilla of Aedes and Anopheles mosquitoes and their importance in repellency. Parasitol Res 99:491–499CrossRefPubMedGoogle Scholar
  3. Amer A, Mehlhorn H (2006c) Larvicidal effects of various essential oils against Aedes, Anopheles, and Culex larvae (Diptera, Culicidae). Parasitol Res 99:466–472CrossRefPubMedGoogle Scholar
  4. Cetin H, Yanikoglu A (2006) Study of the larvicidal activity of Origanum (Labiatae) species from Southwest Turkey. J Vect Eco 31:118–122CrossRefGoogle Scholar
  5. 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 spp. Biores Technol 99:3617–3622CrossRefGoogle Scholar
  6. Cheng SS, Chua MT, Chang EH, Huang CG, Chen WJ, Chang ST (2009) Variations in insecticidal activity and chemical compositions of leaf essential oils from Cryptomeria japonica at different ages. Biores Technol 100:465–470CrossRefGoogle Scholar
  7. Crouch NR, Langlois A, Mulholland DA, Nair JJ (2005) A novel alkylamide from the leaves of Acmella caulirhiza (Asteraceae), a traditional surface analgesic. S Afr J Bot 71:228–230Google Scholar
  8. He X-G, Lin L-Z, Bernart MW, Lian L-Z (1998) Analysis of alkamides in roots and achenes of Echinacea purpurea by Liquid chromatography- electrospray mass spectrometry. J Chromato A 815:205–211CrossRefGoogle Scholar
  9. Hudaib M, Fiori J, Bellardi MG, Rubies-Autonell C, Cavsini V (2002) GC-MS analysis of the lipophilic principles of Echinacea purpurea and evaluation of cucumber mosaic cucumovirus (CMV) infection. J Pharma Biomed Anal 29:1053–1060CrossRefGoogle Scholar
  10. Jondiko IJO (1986) A mosquito larvicide in Spilanthes mauritiana. Phytochemistry 25:2289–2290Google Scholar
  11. Kiszewski A, Johns B, Schapira A, Delacollette C, Crowell V, Tan-Torres T, Ameneshewa B, Teklehaimonat A, Nafo-Traore F (2007) Estimated global resources needed to attain international malaria control goals. Bull WHO 85:623–630PubMedGoogle Scholar
  12. Ley JP, Blings M, Krammer G, Reinders G, Schmidt CO, Bertram HJ (2006) Isolation and synthesis of acmellonate, a new unsaturated long chain 2-ketol ester from Spilanthes acmella. Nat Prod Res 20:798–804CrossRefPubMedGoogle Scholar
  13. Nakatani N, Nagashima M (1992) Pungent alkamides from Spilanthes acmella L. var. oleracea Clarke. Biosc Biotech Biochem 56:759–762CrossRefGoogle Scholar
  14. Nathan SS (2007) The use of Eucalyptus tereticornis Sm. (Myrtaceae) oil (leaf extract) as a natural larvicidal agent against the malaria vector Anopheles stephensi Liston (Diptera: Culicidae). Biores Technol 98:1856–1860CrossRefGoogle Scholar
  15. Nathan SS, Kalaivani K, Sehoon K (2006) Effects of Dysoxylum malabaricum Bedd. (Meliaceae) extract on the malarial vector Anopheles stephensi Liston (Diptera: Culicidae). Biores Technol 97:2077–2083CrossRefGoogle Scholar
  16. Ndung'u M, Hassanali A, Hooper AM, Chhabra S, Miller TA, Paul RL, Torto B (2003) Ring A seco mosquito larvicidal limonoids from Turraea wakefieldii. Phytochemistry 64:817–823CrossRefPubMedGoogle Scholar
  17. Ndung'u MW, Kaoneka B, Hassanali A, Lwande W, Hooper AM, Tayman F, Zerbe O, Torto B (2004) New mosquito larvicidal tetranortriterpenoids from Turraea wakefieldii and Turraea floribunda. J Agric Food Chem 52:5027–5031Google Scholar
  18. Pandey V, Agrawal V (2009) Efficient micropropagation protocol in Spilanthes acmella L. possessing strong antimalarial activity. In Vitro Cell Dev Biol Plant 45:491–499Google Scholar
  19. Pandey V, Agrawal V, Raghavendra K, Dash AP (2007) Strong larvicidal activity of three species of Spilanthes (Akarkara) against malaria (Anopheles stephensi Liston, Anopheles culicifacies, species C) and filaria vector (Culex quinquefasciatus Say). Parasitol Res 102:171–174CrossRefPubMedGoogle Scholar
  20. Park IK, Shin SC, Kim CS, Lee HJ, Choi WS, Ahn YJ (2005) Larvicidal activity of lignins identified in Phryma leptostachya var. asiatica roots against three mosquito species. J Agric Food Chem 53:969–972CrossRefPubMedGoogle Scholar
  21. Prabakar K, Jebaneson A (2004) Larvicidal efficacy of some cucurbitaceous plant leaf extracts against Culex quinquefasciatus (Say). Biores Technol 95:113–114CrossRefGoogle Scholar
  22. Rahuman A, Venkatesan P, Geetha K, Gopalakrishnan G, Bagavan A, Kamaraj C (2008a) Mosquito larvicidal activity of gluanol acetate, a tetracyclic triterpenes derived from Ficus racemosa Linn. Parasitol Res 103:333–339CrossRefPubMedGoogle Scholar
  23. Rahuman AA, Gopalakrishnan G, Venkatesan P, Geetha K (2008b) Isolation and identification of mosquito larvicidal compound from Abutilon indicum (Linn.) Sweet. Parasitol Res 102:981–988CrossRefPubMedGoogle Scholar
  24. Ramsewak RS, Erickson AJ, Nair MG (1999) Bioactive N-isobutylamides from the flower buds of Spilanthes acmella. Phytochemistry 51:729–732CrossRefPubMedGoogle Scholar
  25. Senthilkumar N, Varma P, Gurusubramanian G (2009) Larvicidal and adulticidal activities of some medicinal plants against the Malarial Vector, Anopheles stephensi (Liston). Parasitol Res 104:237–244CrossRefPubMedGoogle Scholar
  26. World Health Organization (2005) Resolution WHA. 58.2. Malaria control. In: Fifty-eight World Health Assembly, Resolutions and Decisions Annex. GenevaGoogle Scholar
  27. Xu D, Redman-Furey N (2007) Statistical cluster analysis of pharmaceutical solvents. Int J Pharm 339:175–188CrossRefPubMedGoogle Scholar

Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  1. 1.Department of BotanyUniversity of DelhiDelhiIndia
  2. 2.B.R. Ambedkar Centre for Biomedical ResearchUniversity of DelhiDelhiIndia

Personalised recommendations