Differential anti-insect activity of natural products isolated from Dodonaea viscosa Jacq. (Sapindaceae)
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Laboratorio de Ecología Química, Facultad de Química, Universidad de la República, Montevideo, 11800, Uruguay
Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas, La Laguna, Tenerife, 38206, Spain
Instituto de Ciencias Agrarias, Consejo Superior de Investigaciones Científicas, Madrid, 28006, Spain
Departamento de Química Orgánica, Facultad de Química, Universidad de la República, Montevideo, 11800, Uruguay
Carmen Rossini
Laboratorio de Ecología Química, Facultad de Química, Universidad de la República, Montevideo, 11800, Uruguay
Submission date: 2014-10-27
Acceptance date: 2015-04-21
Journal of Plant Protection Research 2015;55(2):172–178
Botanical biopesticides constitute an important tool for Integrated Pest Management practices. Uruguay has a great poten- tial for developing botanical biopesticides from its abundant native flora. Dodonaea viscosa Jacq. is a native Sapindaceae that in preliminary studies was shown to possess a potential deterrent activity against insect models. In this work, ethanolic extracts of the leaves of this species were studied. Bioguided fractionation and supercritical fluid extraction led to the isolation of active compounds. For that purpose four insect models were used: Epilachna paenulata, Spodoptera littoralis, Myzus persicae, and Rhopalosiphum padi, which are pests of crops of economic importance. Lupeol, stigmasterol, stigmast-7-en-3-ol, and a labdane diterpene were isolated and showed differential activity against the models.
The authors have declared that no conflict of interests exist.
Ali H., Kabir N., Muhammad A., Shah M.R., Musharraf S.G., Iqbal N., Nadeem S. 2014. Hautriwaic acid as one of the hepatoprotective constituent of Dodonaea viscosa. Phytomedicine 21 (2): 131–140.
Behmer S.T., Elias D.O. 1999. The nutritional significance of sterol metabolic constraints in the generalist grasshopper Schistocerca americana. Journal of Insect Physiology 45 (4): 339–348.
Bellomo A., Camarano S., Rossini C., Gonzalez D. 2009. Enantiospecific synthesis and insect feeding activity of sulfurcontaining cyclitols. Carbohydrate Research 344 (1): 44–51.
Brimson J.M., Brimson S.J., Brimson C.A., Rakkhitawatthana V., Tencomnao T. 2012. Rhinacanthus nasutus extracts prevent glutamate and amyloid-beta neurotoxicity in HT-22 mouse hippocampal cells: possible active compounds include lupeol, stigmasterol and beta-sitosterol. International Journal of Molecular Science 13 (4): 5074–5097.
Burns D., Reynolds W. F., Buchanan G., Reese P.B., Enriquez R.G. 2000. Assignment of H-1 and C-13 spectra and investigation of hindered side-chain rotation in lupeol derivatives. Magnetic Resonans of Chemistry 38 (7): 488–493.
Cargnin S.T., Nunes J.M., Haas J.S., Baladao L.F., Cassel E., Vargas R.F., Rech S.B., von Poser G.L. 2010. Supercritical fluid extraction and high performance liquid chromatographic determinations of benzopyrans and phloroglucinol derivative in Hypericum polyanthemum.Journal of Chromatography B 878: 83–87.
Cassel E., Bedinot C., Vargas R.M.V. 2011. Equipamento de extração supercrítica e processo de obtenção de extratos. Solicitação de Patente. [Supercritic extraction equipment and extraction process. Patent request]. Brasil. PROV020110081175.
Castillo L., González-Coloma A., González A., Díaz M., Santos E., Alonso-Paz E., Bassagoda M.J., Rossini C. 2009. Screening of Uruguayan plants for deterrent activity against insects. Industrial Crops and Products 29 (1): 235–240.
Díaz M., Castillo C., Díaz Hernández C.E., González-Coloma A., Rossini C. 2011. Limonoids from Melia azedarach with deterrent activity against insects. Natural Products Journal 2: 36–44.
Diaz M., Castillo L., Díaz C.E., Guillermo Álvarez R., González-Coloma A., Rossini C. 2014. Differential deterrent activity of natural products isolated from Allophylus edulis(Sapindaceae). Advances in Biological Chemistry 4: 168–179.
Diaz M., Rossini C. 2012. Bioactive natural products from Sapindaceae deterrent and toxic metabolites against insects. p. 287–308. In: “Insecticides – Pest Engineering” (F. Perveen, ed.), InTech, Rijeka, Croatia, 550 pp.
Dong L., Zhang Y., Cheng B., Wu Y., Li Y., Yao H., Li Y. 2012. Chemical Constituents from Ampelopsis sinica var. Hancei prevent liver damage. Latin American Journal of Pharmacy 31 (2): 195–199.
dos Santos E.O., Meira M., do Vale A.E., David J.M., de Queiroz L.P., David J.P. 2012. Isolation and characterization of new ceramides from aerial parts of Lepidaploa cotoneaster. Natural Product Communications 7 (6): 781–783.
Garay A., Guido A., López L., Mai P., Piñeiro V. 2008. Dodonaea viscosa(Chirca de monte), especie de interés para la restauración de ambientes costeros en Uruguay. [Dodonaea viscosa (Chirca de monte), species of interest for the restoriation of coastal environments in Uruguay]. Montevideo, Facultad de Ciencias, UdelaR.
Geris R., da Silva I.G., Garcia da Silva H.H., Barison A., Rodrigues-Filho E., Ferreira A.G. 2008. Diterpenoids from Copaifera reticulata Ducke with larvicidal activity against Aedes aegypti(L.) (Diptera, Culicidae). Journal of the São PauloInstitute of Tropical Medicine 50 (1): 25–28.
Gonzalez-Coloma A., Guadano A., Tonn C.E., Sosa M.E. 2005. Antifeedant/insecticidal terpenes from Asteraceae and Labiatae species native to Argentinean senti-arid lands. Zeitschrift für Naturforschung. Section C. Journal of Biosciences 60 (11–12): 855–861.
Gonzalez-Coloma A., Lopez Balboa C., Santana O., Reina M., Fraga B.M. 2011. Triterpene-based plant defenses. Phytochemical Reviews 10: 245–260.
Gutierrez C., Fereres A., Reina M., Cabrera R., Gonzalez-Coloma A. 1997. Behavioral and sublethal effects of structurally related lower terpenes on Myzus persicae. Journal of Chemical Ecology 23 (6): 1641–1650.
Huang J.G., Zhou L.J., Xu H.H., Li W.O. 2009. Insecticidal and cytotoxic activities of extracts of Cacalia tangutica and its two active ingredients against Musca domestica and Aedes albopictus.Journal of Economical Entomology 102 (4): 1444–1447.
Kojima H., Sato N., Hatano A., Ogura H. 1990. Constituents of the labiatae plants. 5. Sterol glucosides from Prunella vulgaris. Phytochemistry 29 (7): 2351–2355.
Kolak U., Topcu G., Birteksoz S., Otuk G., Ulubelen A. 2005. Terpenoids and steroids from the roots of Salvia blepharochlaena. Turkish Journal of Chemistry 29 (2): 177–186.
Kumari A., Kakkar P. 2012. Lupeol prevents acetaminophen induced in vivohepatotoxicity by altering the Bax/Bcl-2 and oxidative stress-mediated mitochondrial signaling cascade. Life Science 90 (15–16): 561–570.
Lee T.H., Chiou J.L., Lee C.K., Kuo Y.H. 2005. Separation and determination of chemical constituents in the roots of Rhus javanica L. var. roxburghiana. Journal of the Chinese Chemical Society 52 (4): 833–841.
Liu Y.W., Cheng Y.B., Liaw C.C., Chen C.H., Guh J.H., Hwang T.L., Shen Y.C. 2012. Bioactive diterpenoids from Callicarpa longissima. Planta Medica 78 (11): 1184–1184.
Lowry R. (1998–2009). VassarStats Web Site for Statistical Computation. http://faculty.vassar.edu/lowr...: August 24, 2011].
Malarvannan S., Giridharan R., Sekar S., Prabavathy V.R., Nair S. 2009. Ovicidal activity of crude extracts of few traditional plants against Helicoverpa armigera(Hübner) (Noctuidae: Lepidoptera). Journal of Biopesticides 2 (1): 64–71.
Malarvannan S., Kumar S.S., Prabavathy V.R., Sudha N. 2008. Individual and synergistic effects of leaf powder of few medicinal plants against American bollworm, Helicoverpa armigera(Hübner) (Noctuidae: Lepidoptera). Asian Journal of Experimental Biological Science 22 (1): 79–88.
Malarvannan S., Subashini H.D. 2007. Efficacy of Dodonaea angustifolia crude extracts against spotted bollworm, Earias vitella(Fab.) (Lepidoptera: Noctuidae). Journal of Entomology 4 (3): 243–247.
Mata R., Contreras J.L., Crisanto D., Pereda-Miranda R., Castaeda P., Del Rio F. 1991. Chemical studies on Mexican plants used in traditional medicine, XVIII. New secondary metabolites from Dodonaea viscosa. Journal of Natural Products 54 (3): 913–917.
Miles D.H., Chittawong V., Payne A.M., Hedin P.A., Kokpol U. 1990. Cotton boll weevil antifeedant activity and antifungal activity (Rhizoctonia solani and Pythium ultimum) of extracts of the stems of Wedelia biflora. Journal of Agriculture and Food Chemistry 38 (7): 1591–1594.
Niu H.M., Zeng D.Q., Long C.L., Peng Y.H., Wang Y.H., Luo J.F., Wang H.S., Shi Y.N., Tang G.H., Zhao F.W. 2010. Clerodane diterpenoids and prenylated flavonoids from Dodonaea viscosa. Journal of Asian Natural Products Research 12 (1): 7–14.
Ortega A., Garcia P.E., Cardenas J., Mancera C., Marquina S., Garduno M.L.D., Maldonado E. 2001. Methyl dodonates, a new type of diterpenes with a modified clerodane skeleton from Dodonaea viscosa. Tetrahedron 57 (15): 2981–2989.
Pitout S., Bues S. 1970. Elevage de plusieursesepeces de Lepidopteres Noctuidae sur milieu artificiel simplifié. [Breeding of several species of Lepidoptera Noctuide on simplifies artifical diet]. Annales de Zoologie Ecologie Animale 2: 79–91.
Rojas A., Cruz S., Ponce-Monter H., Mata R. 1996. Smooth muscle relaxing compounds from Dodonaea viscosa. Planta Medica 62 (2): 154–159.
Rose A.F., Jones K.C., Haddon W.F., Dreyer D.L. 1981. Grindelane diterpenoids acids from Grindelia humilis– feeding deterrency of diterpene acids towards aphids. Phytochemistry 20 (9): 2249–2253.
Saez J., Granados H., Escobar G., Cardona W., Atehortua L., Callejas R., Cortes D., Gonzalez C. 1998. Piperlonguminine and stigmasterol, compounds from roots and stems of Piper auritum, and insecticidal activity of the extracts. Revista Colombiana de Quimica 27 (1): 77–81.
Santana O., Reina M., Fraga B.M., Sanz J., Gonzalez-Coloma A. 2012. Antifeedant activity of fatty acid esters and phytosterols from Echium wildpretii. Chemistry and Biodiversity 9 (3): 567–576.
Sharaby A., Abdel-Rahman H., Moawad S. 2009. Biological effects of some natural and chemical compounds on the potato tuber moth, Phthorimaea operculellaZell. (Lepidoptera: Gelechiidae). Saudi Journal of Biological Science 16 (1): 1–9.
Tandon M., Shukla Y.N., Tripathi A.K., Singh S.C. 1998. Insect antifeedant principles from Vernonia cinerea. Phytotherapy Research 12 (3): 195–199.
Thoison O., Sevenet T., Niemeyer H.M., Russell G.B. 2004. Insect antifeedant compounds from Nothofagus dombeyi and N. pumilio. Phytochemistry 65 (14): 2173–2176.
Wabo H.K., Chabert P., Tane P., Note O., Tala M.F., Peluso J., Muller C., Kikuchi H., Oshima Y., Lobstein A. 2012. Labdane-type diterpenes and flavones from Dodonaea viscosa. Fitoterapia 83 (5): 859–863.
Wagner H., Bladt S. 1996. Plant Drug Analysis: A Thin Layer Chromatography Atlas. Springer, New York, 384 pp.
Wagner H., Ludwig C., Grotjahn L., Khan M.S.Y. 1987. Biologically active saponins from Dodonaea viscosa. Phytochemistry 26 (3): 697–701.
Yang G., Zhu J., Zhang L., Xu Z., Wang G., Zhu W., Hou A.,Wang H. 2013. Dodoviscin a inhibits melanogenesis in mouse b16-f10 melanoma cells. Planta Medica 79 (11): 933–938.