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Mosquitocidal Activity of Acetylenic Compounds from Cryptotaenia canadensis

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Abstract

As part of an on-going program to identify natural products from plants with mosquitocidal activity, two acetylenic compounds were isolated from Cryptotaenia canadensis, a native North American umbellifer frequently encountered in moist woodlands. Fresh foliage, roots, and fruits were extracted with a hot methanol and water mixture and then dried. The extract was partitioned into chloroform and water, and both phases were bioassayed against fourth instars of Culex pipiens at concentrations between 5 and 50 ppm. Only the organic phase was active. Gas–liquid chromatography revealed that the two main components of the organic phase were polyacetylenes. The compounds were isolated by vacuum chromatography on silica gel and identified as falcarinol and falcarindiol based on GC-MS-EI and GC-MS-CI fragmentation patterns, high-resolution MS, and 1H and 13C NMR spectrometric data. The dose–response curves with mosquito larvae were determined by probit analysis. The LC50 values were 3.5 ppm for falcarinol and 6.5 ppm for falcarindiol. The distribution of polyacetylenes varied among plant parts. Fruits contained an unknown compound not found in either the foliage or roots.

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REFERENCES

  • Arnason, T., Swain, T. C.-K., Wat, C. E., Graham, E. A., Partington, S., and Towers, G. H. N. 1981. Mosquito larvicidal activity of polyacetylenes from species in the Asteraceae. Biochem. Syst. Ecol. 9:63-68.

    Google Scholar 

  • Berenbaum, M. 1978. Toxicity of a furanocoumarin to armyworms: A case of biosynthetic escape from insect herbivores. Science 201:532-533.

    Google Scholar 

  • Bernart, M. W., Cardellina, J. H., Balaschak, M. S., Alexander, M. R., Shoemaker, R. H., and Boyd, M. R. 1996. Cytotoxic falcarinol oxylipins from Dendropanax arboreus. J. Nat. Prod. 59:748-753.

    Google Scholar 

  • Bohlmann, F., Niedballa, U., and Rode, K.-M. 1966. Ueber neue Polyine mit C17-Kette. Chem. Ber. 99:3552-3562.

    Google Scholar 

  • Bohlmann, F., Burkhardt, T., and Zdero, C. 1973. Naturally Occurring Acetylenes. Academic Press, London.

    Google Scholar 

  • Bruhn, G., Faasch, H., Hahn, H., Hausen, B., Broehan, J., and Koenig, W. A. 1987. Natuerliche Allergene, I Das Auftreten von Falcarinol und Didehydrofalcarinol in Efeu (Hedera helix L.) Z. Naturforschung 42b:1328-1332.

    Google Scholar 

  • Camm, E. L., Wat, C.-K., and Towers, G. H. N. 1976. An assessment of the roles of furanocoumarins in Heracleum lanatum. Can. J. Bot. 54:2562-2566.

    Google Scholar 

  • Davies, W. P., and Lewis, B. G. 1981. Antifungal activity in carrot roots in relation to storage infection by Mycocentrospora acerina. New Phytol. 89:109-119.

    Google Scholar 

  • Frohne, D., and Jensen, U. 1992. Systematik des Pflanzenreichs. 4. Auflage, Gustav Fischer Verlag, Stuttgart.

    Google Scholar 

  • Gafner, F., Reynolds, G. W., and RodrÍguez, E. 1989. The diacetylene 11,12-dehydrofalcarinol from Hedera helix. Phytochemistry, 28:1256-1257.

    Google Scholar 

  • Garrod, B., Lewis, B. G., and Coxon, D. T. 1978. cis-Heptadeca-1,9-diene-4,6-diyne-3,8-diol, an antifungal polyacetylene from carrot root tissue. Physiol. Plant Pathol. 13:241-246.

    Google Scholar 

  • Garrod, B., Lea, E. J. A., and Lewis, G. 1979. Studies on the mechanism of action of the antifungal compound falcarindiol. New Phytol. 83:463-471.

    Google Scholar 

  • Hansen, L., and Boll, P. M. 1986. The polyacetylenic falcarinol as the major allergen in Scheffleria arboricola. Phytochemistry 25:529.

    Google Scholar 

  • Harborne, J. B. 1971. Phytochemical Ecology. Academic Press, New York.

    Google Scholar 

  • Hegnauer, R. 1971. Chemical patterns and relationships of Umbelliferae. Bot. J. Linn. Soc. 64:(suppl 1):267-277.

    Google Scholar 

  • Holub, M., Toman, J., and Herout, V. 1987. The Phylogenetic relationships of the Asteraceae and Apiaceae based on phytochemical characters. Biochem. Syst. Ecol. 15:321-326.

    Google Scholar 

  • Ikeda, R., Nagao, T., Okabe, O., Nakano, Y., Matsunage, H., Katano, M., and Mori, M. 1998. Antiproliferative constituents in umbelliferae plants—III—Constituents in the root and the ground part of Anthriscus sylvestris Hoffm. Chem. Pharm. Bull. 46:871-874.

    Google Scholar 

  • Jones, G. N., and Fuller, G. D. 1955. Vascular Plants of Illinois. The University of Illinois Press, Urbana and the Illinois State Museum, Springfield, 355 pp.

    Google Scholar 

  • Kemp, M. S. 1978. Falcarindiol: An antifungal polyacetylene from Aegopodium podagraria. Phytochemistry 17:1002.

    Google Scholar 

  • Kern, J. R., and Cardellina, J. H. 1982. Native American medicinal plants, falcarindiol and 3-O-methylfalcarindiol from Osmorhiza occidentalis. J. Nat. Prod. 45:774-776.

    Google Scholar 

  • Lewis, W. H. 1977. Medical Botany: Plants Affecting Man's Health. John Wiley & Sons, New York.

    Google Scholar 

  • Miyazawa, M., Shimamura, H., Bhuva, R. C., Nakamura, S., and Kameoka, H. 1996. Antimutagenic activity of falcarindiol from Peucedanum praeruptorum. J. Agric. Food Chem. 44:3444-3448.

    Google Scholar 

  • Robinson, T. 1991. The Constituents of Higher Plants, 6th ed. Cordus Press, North Amherst, Massachusetts.

    Google Scholar 

  • Villegas, M., Vargas, D., Msonthi, J. D., Marston, A., and Hostettmann, K. 1987. Isolation of the antifungal compounds falcarindiol and sarisan from Heteromorpha trifoliata. Planta Med. 9:36-37.

    Google Scholar 

  • Wat, C.-K., Prasad, S. K., Graham, E. A., Partington, S., Arnason, T., and Towers, G. H. N. 1981. Photosensitation of invertebrates by natural polyacetylenes. Biochem. Syst. Ecol. 9:59-62.

    Google Scholar 

  • Yates, S. G., and England, R. E. 1982. Isolation and analysis of carrot constituents: Myristicin, falcarinol and falcarindiol. J. Agric. Food Chem. 30:317-320.

    Google Scholar 

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Eckenbach, U., Lampman, R.L., Seigler, D.S. et al. Mosquitocidal Activity of Acetylenic Compounds from Cryptotaenia canadensis . J Chem Ecol 25, 1885–1893 (1999). https://doi.org/10.1023/A:1020938001272

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