Skip to main content
SpringerLink
Log in

Larvicidal activity of lignans from Phryma leptostachya L. against Culex pipiens pallens

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

Abstract

The larvicidal activity of crude petroleum ether, ethyl acetate, and methanol extracts of the whole plants of Phryma leptostachya L. was assayed for its toxicity against the early fourth instar larvae of Culex pipiens pallens. The larval mortality was observed after 24 h of exposure. Among three solvent extracts from Phyrma leptostachya L., the petroleum ether extract exhibited the best larvicidal activity. The corresponding LC50 values of petroleum ether, ethyl acetate, and methanol extracts were 3.23, 5.23, and 61.86 ppm against the early fourth instar larvae of Culex pipiens pallens. The petroleum ether extract was successively subjected to column chromatography and preparative high performance liquid chromatography, and yielded the three lignans, phrymarolin-I, haedoxane A, and haedoxane E, which were isolated and identified as new mosquito larvicidal compounds. Phrymarolin-I, haedoxane A, and haedoxane E showed high larvicidal activity, for which the lethal doses LC50 were estimated at 1.21, 0.025, and 0.15 ppm against the early fourth instar larvae of Culex pipiens pallens, respectively. The structures were elucidated by analyses of IR, UV, MS, and NMR spectral data. This is the first report on the mosquito larvicidal activity of the three compounds, phrymarolin-I, haedoxane A, and haedoxane E from Phyrma leptostachya L.

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

  • Bagavan A, Rahuman AA, Kamaraj C, Geetha K (2008) Larvicidal activity of saponin from Achyranthes aspera against Aedes aegypti and Culex quinquefasciatus (Diptera: Culicidae). Parasitol Res 103:223–229

    Article  PubMed  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 

  • Chandrashekhar DP, Satish VP, Bipinchandra KS, Rahul BS (2011) Bioefficacy of Plumbago zeylanica (Plumbaginaceae) and Cestrum nocturnum (Solanaceae) plant extracts against Aedes aegypti (Diptera: Culicide) and nontarget fish Poecilia reticulata. Parasitol Res 108:1253–1263

    Article  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 

  • Devonshire AL, Guillet P, Pasteur N, Pauron D (1998) Molecular characterization of pyrethroid knockdown resistance (kdr) in the major malaria vector Anopheles gambiae s.s. Insect Mol Biol 7:179–184

    Article  PubMed  Google Scholar 

  • Eckenbach U, Lampman RL, Seigle DS, Ebiner J, Novek RJ (1999) Mosquitocidal activity of acetylenic compounds from Cryptotaenia canadensis. J Chem Ecol 25:1885–1893

    Article  CAS  Google Scholar 

  • Elango G, Rahuman AA, Bagavan A, Kamaraj C, Zahir AA, Venkatesan C (2009) Laboratory study on larvicidal activity of indigenous plant extracts against Anopheles subpictus and Culex tritaeniorhynchus. Parasitol Res 104:1381–1388

    Article  PubMed  CAS  Google Scholar 

  • Elango G, Rahuman AA, Bagavan A, Kamaraj C, ZahirAA RG, Marimuthu S, Santhoshkumar T (2010) Efficacy of botanical extracts against Japanese encephalitis vector, Culex tritaeniorhynchus. Parasitol Res 106:481–492

    Article  PubMed  Google Scholar 

  • Govindarajan M (2011) Evaluation of indigenous plant extracts against the malarial vector, Anopheles stephensi (Liston) (Diptera: Culicidae). Parasitol Res 109:93–103

    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 10(5):1455–1458

    Article  Google Scholar 

  • Hemingway J, Hawkes NJ, McCarroll L, Ranson H (2004) The molecular basis of insecticide resistance in mosquitoes. Insect Biochem Mol Biol 34:653–665

    Article  PubMed  CAS  Google Scholar 

  • Ishibashi F, Taniguchi E (1989) Syntheses of (±)-Haedoxan A, D, E and their stereoisomers. Agric Biol Chem 53:1565–1573

    Article  CAS  Google Scholar 

  • Ishibashi E, Taniguchi E (1998) Synthesis and absolute configuration of the insecticidal sesquilignan (+)-haedoxan A. Phytochemisty 49:613–622

    Article  CAS  Google Scholar 

  • Kalu IG, Ofoegbu U, Eroegbusi J, Nwachukwu CU, Ibeh B (2010) Larvicidal activities of ethanol extract of Allium sativum (garlic bulb) against the filarial vector, Culex quinquefasciatus. J Med Plants Res 4(6):496–498

    Google Scholar 

  • Kamaraj C, Rahuman AA, Bagavan A (2008a) Antifeedant and larvicidal effects of plant extracts against Spodoptera litura (F.), Aedes aegypti L. and Culex quinquefasciatus Say. Parasitol Res 103:325–331

    Article  CAS  Google Scholar 

  • Kamaraj C, Rahuman AA, Bagavan A (2008b) Screening for antifeedant and larvicidal activity of plant extracts against Helicoverpa armigera (Hübner), Sylepta derogata (F.) and Anopheles stephensi (Liston). Parasitol Res 103:1361–1368

    Article  CAS  Google Scholar 

  • Kamaraj C, AbdulRahuman 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 

  • 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 (Published online). doi:10.1007/s00436-011-2384-6

  • Koodalingam A, Mullainadhan P, Arumugam M (2009) Antimosquito activity of aqueous kernel extract of soapnut Sapindus emarginatus: impact on various developmental stages of three vector mosquito species and nontarget aquatic insects. Parasitol Res 105:1425–1434

    Article  PubMed  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 

  • Lee SM, Min BS, Kho YH (2002) Brine shrimp lethality of the compounds from n Phryma leptostachya L. Arch Pharmacal Res 25:652–654

    Article  CAS  Google Scholar 

  • Li XL, Ma L, Sun LX, Zhu CL (2002) Biotic characteristics in the deltamethrin-suseptible and resistant strain of Culex pipiens pallens (Diptera-Culicidae) in China. Appl Entomol Zool 37:21–24

    Article  Google Scholar 

  • Maheswaran R, Sathish S, Ignacimuthu S (2008) Larvicidal activity of Leucas aspera (Wild.) against the larvae of Culex quinquefasciatus Say. and Aedes aegypti L. Int J Integr Biol 2:214–217

    Google Scholar 

  • Mathew N, Anitha MG, Bala TSL, Sivakumar SM, Narmadha R, Kalyanasundaram M (2009) Larvicidal activity of Saraca indica, Nyctanthes arbortristis, and Clitoria ternatea extracts against three mosquito vector species. Parasito lRes 104:1017–1025

    Article  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 

  • Milam CD, Farris JL, Wilhide JD (2000) Evaluating mosquito control pesticides for effect on target and nontarget organisms. Arch Environ Contam Toxicol 39:324–328

    Article  PubMed  CAS  Google Scholar 

  • Oliveira PV, Ferreira JC Jr, Moura FS, Lima GS, Oliveira FM, Oliveira PES, Conserva LM (2010) Larvicidal activity of 94 extracts from ten plant species of northeastern of Brazil against Aedes aegypti L. (Diptera: Culicidae). Parasitol Res 107:403–407

    Article  PubMed  Google Scholar 

  • Omena MC, Navarro DMAF, Paula JE, Luna JS, Ferreira de Lima MR, Sant’Ana AEG (2007) Larvicidal activities against Aedes aegypti of some Brazilian medicinal plants. Bioresour Technol 98:2549–2556

    Article  PubMed  Google Scholar 

  • Park IK, Lee SG, Shin SC, Park JD, Ahn YJ (2002) Larvicidal activity of isobutylamides identified in Piper nigrum fruits against three mosquito species. J Agric Food Chem 50:1866–1870

    Article  PubMed  CAS  Google Scholar 

  • Park IK, Shin SC, Kim CS, Lee HJ, Choi WS, Ahn YJ (2005) Larvicidal activity of lignans identified in Phryma leptostachya Var. asiatica roots against three mosquito species. J Agric Food Chem 53:969–972

    Article  PubMed  CAS  Google Scholar 

  • Pavela R (2008) Larvicidal effects of various Euro-Asiatic plants against Culex quinquefasciatus Say larvae (Diptera: Culicidae). Parasitol Res 102:555–559

    Article  PubMed  Google Scholar 

  • Peng Z, Yang J, Wang H, Simons FER (1999) Production and characterization of monoclonal antibodies to two new mosquito Aedes aegypti salivary proteins. Insect Biochem Mol Biol 29:909–914

    Article  PubMed  CAS  Google Scholar 

  • Perumalsamy H, Kim NJ, Ahn YJ (2009) Larvicidal activity of compounds isolated from Asarum heterotropoides against Culex pipiens pallens, Aede aegypti, and Ochlerotatus togoi (Diptera:Culicidae). J Med Entomol 46(6):1420–1423

    Article  PubMed  CAS  Google Scholar 

  • Rahuman AA, Venkatesan P (2008) Larvicidal efficacy of five cucurbitaceous plant leaf extracts against mosquito species. Parasitol Res 103:133–139

    Article  PubMed  Google Scholar 

  • Rahuman AA, Gopalakrishnan G, Venkatesan P, Geetha K (2008a) Larvicidal activity of some Euphorbiaceae plant extracts against Aedes aegypti and Culex quinquefasciatus (Diptera: Culicidae). Parasitol Res 102:867–873

    Article  PubMed  Google Scholar 

  • Rahuman AA, Venkatesan P, Gopalakrishnan G (2008b) Mosquito larvicidal activity of oleic and linoleic acids isolated from Citrullus colocynthis (Linn.) Schrad. Parasitol Res 103:1383–1390

    Article  PubMed  Google Scholar 

  • Rahuman AA, Venkatesan P, Geetha K, Gopalakrishnan G, Bagavan A, Kamaraj C (2008c) Mosquito larvicidal activity of gluanol acetate, a tetracyclic triterpenes derived from Ficus racemosa Linn. Parasitol Res 103:333–339

    Article  PubMed  Google Scholar 

  • Rahuman AA, Bagavan A, Kamara C, Saravanan E, Zahir AA, Elango G (2009) Efficacy of larvicidal botanical extracts against Culex quinquefasciatus Say (Diptera: Culicidae). Parasitol Res 104:1365–1372

    Article  PubMed  CAS  Google Scholar 

  • Rajkumar S, Jebanesan A (2008) Bioactivity of flavonoid compounds from Poncirus trifoliata L. (Family: Rutaceae) against the dengue vector, Aedes aegypti L. (Diptera: Culicidae). Parasitol Res 104:19–25

    Article  PubMed  CAS  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

    PubMed  CAS  Google Scholar 

  • Soderlund DM, Knipple DC (2003) The molecular biology of knockdown resistance to pyrethroid insecticides. Insect Biochem Mol Biol 33:563–577

    Article  PubMed  CAS  Google Scholar 

  • Taniguchi E, Oshima Y (1972a) Phrymarolin-I, a novel lignan fro Phryma leptostachya L. Agric Biol Chem 36:1018–1025

    Google Scholar 

  • Taniguchi E, Oshima Y (1972b) Structure of phrymarolin-II. Agric Biol Chem 36:1489–1496

    Article  CAS  Google Scholar 

  • Taniguchi E, Oshima Y (1972c) New gmelinol-type lignan, leptostachyol acetate. Tetrahe- dron Lett 8:653–656

    Article  Google Scholar 

  • Taniguchi E, Imamura K, Ishibashi F, Matsui T, Nishio A (1989) Structure of the novel insecticides sesquilignan, haedoxan A. Agric Biol Chem 53(631):643

    Google Scholar 

  • World Health Organization (1981) Instructions for determining the susceptibility or resistance of mosquito larvae to insecticides. WHO/VBC/81.807. WHO, Geneva

    Google Scholar 

Download references

Acknowledgments

This work was supported by the National Key S&T Research Foundation of China (2010CB126105) and the National Natural Science Foundation of China (30871663, 31071704).

Author information

Authors and Affiliations

  1. State Key Laboratory of Crop Stress Biology in Arid Areas, Northwest A & F University, Yangling, Shaanxi, 712100, China

    Xin-min Xiao & Wen-jun Wu

  2. Shaanxi Province Key Laboratory Research & Development on Botanical Pesticide, Northwest A & F University, Yangling, Shaanxi, 712100, China

    Xin-min Xiao, Shao-peng Wei & Wen-jun Wu

  3. Key Laboratory of Plant Protection Resources and Pest Integrated Management, Ministry of Education, College of Plant Protection, Northwest A & F University, Yangling, Shaanxi, 712100, China

    Zhao-nong Hu & Bao-jun Shi

Authors
  1. Xin-min Xiao
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhao-nong Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Bao-jun Shi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Shao-peng Wei
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Wen-jun Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Wen-jun Wu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Xiao, Xm., Hu, Zn., Shi, Bj. et al. Larvicidal activity of lignans from Phryma leptostachya L. against Culex pipiens pallens . Parasitol Res 110, 1079–1084 (2012). https://doi.org/10.1007/s00436-011-2591-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00436-011-2591-1

Keywords

Search

Navigation