Skip to main content
SpringerLink
Log in

Mosquito larvicidal activity of alkaloids and limonoids derived from Evodia rutaecarpa unripe fruits against Aedes albopictus (Diptera: Culicidae)

  • Original Paper
  • Published:
Parasitology Research Aims and scope Submit manuscript

Abstract

In recent years, uses of environment friendly and biodegradable natural insecticides of plant origin have received renewed attention as agents for vector control. During a screening program for new agrochemicals from Chinese medicinal herbs and local wild plants, the ethanol extract of Evodia rutaecarpa Hook f. et Thomas (Rutaceae) unripe fruits was found to possess larvicidal activity against the mosquitoes. The aim of this research was to determine larvicidal activity of the ethanol extract of E. rutaecarpa unripe fruits and the isolated constituents against the larvae of the Culicidae mosquito Aedes albopictus. The powder, 5 kg of the fruit material, was extracted with 30 l of 95 % ethanol, filtered, and evaporated to dryness in a rotary vacuum evaporator. The crude extract was then partitioned between methanol–water and n-hexane. The n-hexane fraction was evaporated off to given n-hexane extract. The aqueous layer was repartitioned with chloroform to provide chloroform extract after evaporation of the solvent. Further partitioning with ethyl acetate gave a residue after evaporation of the solvent. Bioactivity-directed chromatographic separation of chloroform extract on repeated silica gel columns led to the isolation of three alkaloids (evodiamine, rutaecarpine, and wuchuyuamide I) and two limonoids (evodol and limonin). The structures of the constituent compounds were elucidated based on high-resolution electron impact mass spectrometry and nuclear magnetic resonance. Evodiamine, rutaecarpine, and wuchuyuamide I exhibited strong larvicidal activity against the early fourth instar larvae of A. albopictus with LC50 values of 12.51, 17.02, and 26.16 μg/ml, respectively. Limonin and evodol also possessed larvicidal activity against the Asian tiger mosquitoes with LC50 values of 32.43 and 52.22 μg/ml, respectively, while the ethanol extract had a LC50 value of 43.21 μg/ml. The results indicated that the ethanol extract of E. rutaecarpa and the five isolated constituents have a good potential as a source for natural larvicides.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  • Amer A, Mehlhorn H (2006) Larvicidal effect of various essential oils against Aedes, Anopheles, and Culex larvae (Diptera, Culicidae). Parasitol Res 99:466–472

    Article  PubMed  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  PubMed  CAS  Google Scholar 

  • Cheng SS, Huang CG, Chen YJ, Yu JJ, Chen WJ, Chang ST (2009a) Chemical compositions and larvicidal activities of leaf essential oils from two Eucalyptus species. Bioresour Technol 100:452–456

    Article  PubMed  CAS  Google Scholar 

  • Cheng SS, Liu JY, Huang CG, Hsui YR, Chen WJ, Chang ST (2009b) Insecticidal activities of leaf essential oils from Cinnamomum osmophloeum against three mosquito species. Bioresour Technol 100:457–464

    Article  PubMed  CAS  Google Scholar 

  • Cheng SS, Chua MT, Chang EH, Huang CG, Chen WJ, Chang ST (2009c) Variations in insecticidal activity and chemical compositions of leaf essential oils from Cryptomeria japonica at different ages. Bioresour Technol 100:465–470

    Article  PubMed  CAS  Google Scholar 

  • Cheng SS, Chang HT, Lin CY, Chen PS, Huang CG, Chen WJ, Chang ST (2009d) Insecticidal activities of leaf and twig essential oils from Clausena excavata against Aedes aegypti and Aedes albopictus larvae. Pest Manag Sci 65:339–343

    Article  PubMed  CAS  Google Scholar 

  • Conti B, Canale A, Bertoli A, Gozzini F, Pistelli L (2010) Essential oil composition and larvicidal activity of six Mediterranean aromatic plants against the mosquito Aedes albopictus (Diptera: Culicidae). Parasitol Res 107:1455–1461

    Article  PubMed  Google Scholar 

  • Elango G, Rahuman AA, Kamaraj C, Bagavan S, Zahir AA (2011) Efficacy of medicinal plant extracts against malarial vector, Anopheles subpictus Grassi. Parasitol Res 108:1437–1445

    Article  PubMed  Google Scholar 

  • Gu HJ, Cheng SS, Huang CG, Chen WJ, Chang ST (2009) Mosquito larvicidal activities of extractives from black heartwood-type Cryptomeria japonica. Parasitol Res 105:1455–1458

    Article  PubMed  Google Scholar 

  • Hafeez F, Akram W, Shaalan EA (2011) Mosquito larvicidal activity of citrus limonoids against Aedes albopictus. Parasitol Res 109:221–229

    Article  PubMed  Google Scholar 

  • Isman MB (2006) Botanical insecticides, deterrents, and repellents in modern agriculture and an increasingly regulated world. Ann Rev Entomol 51:45–66

    Article  CAS  Google Scholar 

  • Jayaprakasha GK, Singh RP, Pereira J, Sakariah KK (1997) Limonoids from Citrus reticulata and their moult inhibiting activity in mosquito Culex quinquefasciatus larvae. Phytochemistry 44:843–846

    Article  PubMed  CAS  Google Scholar 

  • Jiang CX, Xiong ZM, Li Q, Wang HJ, Yang QF (2008a) Study on the bioactivity of Evodia rutaecarpa (Juss.) Benth. ethanol extracts against Spodoptera litura Fab. J Southwest Univ 30:105–108, in Chinese with English abstract

    Google Scholar 

  • Jiang CX, Xiong ZM, Li Q, Wang HJ, Yang QF (2008b) Study on the antifeedant activity of ethanol extracts from Evodia rutaecarpa (Juss.) Benth. against Pieris rapae L. J Anhui Agric Sci 36:229–230, in Chinese with English abstract

    Google Scholar 

  • Jiangsu New Medical College (1977) Dictionary of Chinese Herbal Medicine. Shanghai Science & Technology, Shanghai, pp 737–739

    Google Scholar 

  • Kamaraj C, Rahuman AA, Mahapatra A, Bagavan A, Elango G (2010) Insecticidal and larvicidal activities of medicinal plant extracts against mosquitoes. Parasitol Res 107:1337–1349

    Article  PubMed  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 

  • Khandagle AJ, Tare VS, Raut KD, Morey RA (2011) Bioactivity of essential oils of Zingiber officinalis and Achyranthes aspera against mosquitoes. Parasitol Res 109:339–343

    Article  PubMed  Google Scholar 

  • Kim YC, Kim NY, Jeong SJ, Sohn DH, Miyamoto T, Higuchi R (1998) Biologically active quinolone alkaloids from Evodia rutaecarpa on Artemia salina. Planta Med 64:490

    Article  PubMed  CAS  Google Scholar 

  • Kiprop AK, Rajab MS, Wanjala FME (2005) Isolation and characterization of larvicidal components against mosquito larvae (Aedes aegypti Linn.) from Calodendrum capense Thunb. Bull Chem Soc Ethiopia 19:145–148

    CAS  Google Scholar 

  • Koliopoulos G, Pitarokili D, Kioulos E, Michaelakis A, Tzakou O (2010) Chemical composition and larvicidal evaluation of Mentha, Salvia, and Melissa essential oils against the West Nile virus mosquito Culex pipiens. Parasitol Res 107:327–335

    Article  PubMed  Google Scholar 

  • Konishi T, Kondo S, Uchiyama N (2008) Larvicidal activities of sesquiterpenes from Inula helenium (Compositae) against Aedes albopictus (Diptera: Culicidae) and Paratanytarsus grimmii (Diptera: Chironomidae). Appl Entomol Zool 43:77–81

    Article  CAS  Google Scholar 

  • Liu ZL, Du SS (2011) Fumigant components from the essential oil of Evodia rutaecarpa Hort unripe fruits. E-J Chem 8:1937–1943

    Article  CAS  Google Scholar 

  • Liu ZL, Ho SH (1999) Bioactivity of the essential oil extracted from Evodia rutaecarpa Hook f. et Thomas against the grain storage insects, Sitophilus zeamais Motsch. and Tribolium castaneum (Herbst). J Stored Prod Res 35:317–328

    Article  Google Scholar 

  • Liu ZL, Goh SH, Ho SH (2007) Screening of Chinese medicinal herbs for bioactivity against Sitophilus zeamais Mostchulsky and Tribolium castaneum (Herbst). J Stored Prod Res 43:290–296

    Article  Google Scholar 

  • Maheswaran R, Ignacimuthu S (2012) A novel herbal formulation against dengue vector mosquitoes Aedes aegypti and Aedes albopictus. Parasitol Res. doi:10.1007/s00436-011-2702-z

  • Manners GD, Jacob RA, Breksa AP, Schoch TK, Hasegawa S (2003) Bioavailability of citrus limonoids in humans. J Agric Food Chem 51:4156–4161

    Article  PubMed  CAS  Google Scholar 

  • Miyazawa M, Fujioka J, Ishikawa Y (2002) Insecticidal compounds from Evodia rutaecarpa against Drosophila melanogaster. J Sci Food Agric 82:1574–1578

    Article  CAS  Google Scholar 

  • 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 64:817–823

    Article  PubMed  Google Scholar 

  • Nicoletti M, Serafini M, Aliboni A, D'Andrea A, Mariani S (2010) Toxic effects of neem cake extracts on Aedes albopictus (Skuse) larvae. Parasitol Res 107:89–94

    Article  PubMed  Google Scholar 

  • Pavela R, Vrchotová N, Tříska J (2009) Mosquitocidal activities of thyme oils (Thymus vulgaris L.) against Culex quinquefasciatus (Diptera: Culicidae). Parasitol Res 105:1365–1370

    Article  PubMed  Google Scholar 

  • Pitarokili D, Michaelakis A, Koliopoulos G, Giatropoulos A, Tzakou O (2011) Chemical composition, larvicidal evaluation, and adult repellency of endemic Greek Thymus essential oils against the mosquito vector of West Nile virus. Parasitol Res 109:425–430

    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(3):637–643

    Article  PubMed  Google Scholar 

  • Sakuma M (1998) Probit analysis of preference data. Appl Entomol Zool 33:339–347

    Google Scholar 

  • Shoji N, Umeyama A, Iuchi A, Saito N, Arihara S, Nomoto K, Ohizumi Y (1989) Two novel alkaloids from Evodia rutaecarpa. J Nat Prod 52:1160–1162

    Article  CAS  Google Scholar 

  • Shwetha VR, 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  Google Scholar 

  • Sreelatha T, Hymavathi A, Murthy JM, Rani PU, Rao JM, Babu KS (2010) Bioactivity-guided isolation of mosquitocidal constituents from the rhizomes of Plumbago capensis Thunb. Bioorg Med Chem Lett 20(9):2974–2977

    Google Scholar 

  • Sugimoto T, Ueno A, Kadota S, Cui C, Kikuchi T (1988) New 5β-H limonoids from Evodia rutaecarpa Bentham. Chem Pharm Bull 36:1237–1240

    Article  CAS  Google Scholar 

  • Talontsi FM, Matasyoh JC, Ngoumfo RM, Chepkorir R (2011) Mosquito larvicidal activity of alkaloids from Zanthoxylum lemairei against the malaria vector Anopheles gambiae. Pesticide Biochem Physiol 99:82–85

    Article  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 

  • World Health Organization (1981) Instruction for determining the susceptibility or resistance of mosquito larvae to insecticide. WHO/VBC/81.80

  • Yang RZ, Tang CS (1988) Plants used for pest control in China: a literature review. Econ Bot 42:376–406

    Article  Google Scholar 

  • Yang YC, Lee SG, Lee HK, Kim MK, Lee SH, Lee HS (2002) A piperidine amide extracted from Piper longum L. fruit shows activity against Aedes aegypti mosquito larvae. J Agric Food Chem 50:3765–3767

    Article  PubMed  CAS  Google Scholar 

  • Zuo GY, Yang XS, Hao XJ (2000) Two new indole alkaloids from Evodia rutaecarpa. Chin Chem Lett 11:127–128

    CAS  Google Scholar 

Download references

Acknowledgments

This work was funded by the Hi-Tech Research and Development of China (2011AA10A202 and 2006AA10A209). We thank Dr. Q.R. Liu from the College of Life Sciences, Beijing Normal University, Beijing 100875, for the identification of the investigated medicinal herb.

Author information

Authors and Affiliations

  1. Department of Entomology, China Agricultural University, Haidian District, Beijing, 100193, China

    Zhi Long Liu & Qi Zhi Liu

  2. State Key Laboratory of Earth Surface Processes and Resource Ecology, Beijing Normal University, Haidian District, Beijing, 100875, China

    Shu Shan Du

  3. Analytic and Testing Center, Beijing Normal University, Haidian District, Beijing, 100875, China

    Zhi Wei Deng

Authors
  1. Zhi Long Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Qi Zhi Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shu Shan Du
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zhi Wei Deng
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zhi Long Liu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Liu, Z.L., Liu, Q.Z., Du, S.S. et al. Mosquito larvicidal activity of alkaloids and limonoids derived from Evodia rutaecarpa unripe fruits against Aedes albopictus (Diptera: Culicidae). Parasitol Res 111, 991–996 (2012). https://doi.org/10.1007/s00436-012-2923-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00436-012-2923-9

Keywords

Search

Navigation