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Toxicity of nitro compounds fromLotus pedunculatus to grass grub (Costelytra zealandica) (Coleoptera: Scarabaeidae)

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Abstract

Crude extracts of root of the forage legumesLotus pedunculatus andCoronilla varia (crownvetch) were toxic when administered orally to 3rd instarCostelytra zealandica larvae. A group of 3-nitropropanoyl-d-glucopyranoses was isolated from active fractions of the crude extracts. These toxins, some of which were already known fromC. varia, have not previously been reported fromL. pedunculatus. The compounds were present in root tissue of this species at a concentration of about 1% dry weight. They include the triester karakin and the diesters coronarian and cibarian, all of which were toxic to larvae ofC. zealandica at levels which could account fully for the activity of the crude extracts.

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References

  • Baluch, S.J., Risius, M.L., Hill, R.R., andCleveland, R.W. 1978. Genetic variability for yield and plant height in crownvetch.Crop Sci. 18:396–398.

    Google Scholar 

  • Bellamy, L.J. 1958. The Infra-red Spectra of Complex Molecules, 2nd ed. Methuen, London, 425 pp.

    Google Scholar 

  • Byers, R.A., Gustine, D.L., andMoyer, B.G. 1977. Toxicity of β-nitropropionic acid toTrichoplusia ni.Environ. Entomol. 6:229–232.

    Google Scholar 

  • Farrell, J.A.K., andSweney, W.J. 1972. Plant resistance to the grass grub,Costelytra zealandica (Col. Scarabaeidae). I. Resistance in pasture legumes.N.Z. J. Agric. Res. 15:904–908.

    Google Scholar 

  • Farrell, J.A.K., andSweney, W.J. 1974. Plant resistance to the grass grub,Costelytra zealandica (Coleoptera: Scarabaeidae). III. Resistance inLotus andLupinus.N.Z. J. Agric. Res. 17:69–72.

    Google Scholar 

  • Farrell, J.A.K., andStufkens, M.W. 1977. Resistance to the grass grubCostelytra zealandica (White) (Coleoptera: Scarabaeidae) in some crop plant species.N.Z. J. Agric. Res. 20:503–505.

    Google Scholar 

  • Gustine, D.L. 1979. Aliphatic nitrocompounds in crownvetch: A review.Crop Sci. 19:197–203.

    Google Scholar 

  • Gustine, D.L., Shenk, J.S., Moyer, B.G., andBarnes, R.F. 1974. Isolation of β-nitropropionic acid from crownvetch.Agron. J. 66:636–639.

    Google Scholar 

  • Harlow, M.C., Stermitz, F.R., andThomas, R.D. 1975. Isolation of nitro compounds fromAstragalus species.Phytochemistry 14:1421–1423.

    Google Scholar 

  • Hass, H.B., Feuer, H., andPier, S.M. 1951. The preparation of β-nitropropanoic acid.J. Am. Chem. Soc. 73:1858.

    Google Scholar 

  • Majak, W., andBose, R.J. 1974. Chromatographic methods for the isolation of miserotoxin and detection of aliphatic nitro compounds.Phytochemistry 13:1005–1010.

    Google Scholar 

  • Majak, W., andBose, R.J. 1976. Nitropropanoyl glucopyranoses inCoronilla varia.Phytochemistry 15:415–417.

    Google Scholar 

  • Matsumoto, H., Unrau, A.M., Hylin, J.W., andTemple, B. 1961. Spectrophotometric determination of 3-nitropropanoic acid in biological extracts.Anal. Chem. 33:1442–1444.

    Google Scholar 

  • Moyer, B.G., Pfeffer, P.E., Moniot, J.L., Shamma, M., andGustine, D.L. 1977. Corollin, coronillin and coronarian: Three new 3-nitropropanoyl-d-glucopyranoses fromCoronilla varia.Phytochemistry 16:375–377.

    Google Scholar 

  • Moyer, B.G., Pfeffer, P.E., Valentine, K.M., andGustine, D.L. 1979. 3-Nitropropanoyl-d-glucopyranoses ofCorynocarpus laevigatus.Phytochemistry 18:111–113.

    Google Scholar 

  • Ohashi, M., Tsujimoto, K., Tamura, S., andNakayama, N. 1980. In-beam electron impact mass spectrometry ofN-carbobenzoxy derivatives of oligopeptides composed of leucine and isoleucine.Biomed. Mass Spectrom. 7:153–159.

    PubMed  Google Scholar 

  • Russell, G.B., Sutherland, O.R.W., Hutchins, R.F.N., andChristmas, P.E. 1978. Vestitol: A phytoalexin with insect feeding deterrent activity.J. Chem. Ecol. 4:571–579.

    Google Scholar 

  • Shenk, J.S., Wangsness, P.J., Leach, R.M., Gustine, D.L., Gobble, J.L., andBarnes, R.F. 1976. Relationship between β-nitropropionic acid content of crownvetch and toxicity in non-ruminant animals.J. Anim. Sci. 42:616–621.

    PubMed  Google Scholar 

  • Stermitz, F.R., andYost, G.S. 1978. Analysis and characterization of nitro compounds fromAstragalus species,In R.F. Keeler, K.R. Van Kampen, and L.F. James (eds.). Effects of Poisonous Plants on Livestock. Academic Press, New York. 600 pp.

    Google Scholar 

  • Stermitz, F.R., Lowry, W.T., Ubben, E., andSharifi, I. 1972. 1,6-Di-3-nitropropionyl-β-d-glucopyranoside fromAstragalus cibarius.Phytochemistry 11:3525–3527.

    Google Scholar 

  • Sutherland, O.R.W., andGreenfield, W.J. 1976. A new toxin for grass grub and black beetle in resistant lotus major. Proc. 29th N.Z. Weed Pest Contr. Conf. 29: 158–160.

    Google Scholar 

  • Sutherland, O.R.W., andGreenfield, W.J. 1978. Effect of root extracts of resistant pasture plants on the feeding and survival of black beetle larvaeHeteronychus arator (Scarabaeidae).N.Z. J. Zool. 5:173–175.

    Google Scholar 

  • Sutherland, O.R.W., Hood, N.D., andHillier, J.R. 1975a. Lucerne root saponins a feeding deterrent for the grass grubCostelytra zealandica (Coleoptera: Scarabaeidae).N.Z. J. Zool. 2:93–100.

    Google Scholar 

  • Sutherland, O.R.W., Mann, J., andHillier, J.R. 1975b. Feeding deterrents for the grass grubCostelytra zealandica in the root of a resistant pasture plant,Lotus pedunculatus. N.Z. J. Zool 2:509–512.

    Google Scholar 

  • Sutherland, O.R.W., Hutchins, R.F.N., andGreenfield, W.J. 1982a. Effect of lucerne saponins andLotus condensed tannins on survival of grass grubCostelytra zealandica.N.Z. J. Zool. 9:511–514.

    Google Scholar 

  • Sutherland, O.R.W., Hutchins, R.F.N., Russell, G.B., Lane, G.A., andBiggs, D.R. 1982b. Biochemical plant resistance mechanisms: An evaluation of basic research,in K.E. Lee (ed.). Proceedings of the 3rd Australasian Conference on Grassland Invertebrate Ecology. S.A. Govt. Printer, Adelaide. 402 pp.

    Google Scholar 

  • Wheeler, A.G., Jr. 1974. Phytophagous arthropod fauna of crownvetch in Pennsylvania.Can. Entomol. 106:897–908.

    Google Scholar 

  • Williams, M.C., andJames, L.F. 1978. Livestock poisoning from nitro-bearingAstragalus.in R.F. Keeler, K.R. Van Kampen, and L.F. James (eds.). Effects of Poisonous Plants on Livestock. Academic Press, New York. 600 pp.

    Google Scholar 

  • Williams, M.C. 1983. Toxic nitro compounds inLotus.Agron. J. 75:520–522.

    Google Scholar 

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Hutchins, R.F.N., Sutherland, O.R.W., Gnanasunderam, C. et al. Toxicity of nitro compounds fromLotus pedunculatus to grass grub (Costelytra zealandica) (Coleoptera: Scarabaeidae). J Chem Ecol 10, 81–93 (1984). https://doi.org/10.1007/BF00987645

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  • DOI: https://doi.org/10.1007/BF00987645

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