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Hydroxamic acid glucosides in honeydew of aphids feeding on wheat

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Abstract

DIMBOA glucoside (2-O-/gb-D-glucopyranosyl-4-hydroxy-7-meth-oxy-1,4-benzoxazin-3-one), the main hydroxamic acid (Hx) in intact wheat plants, was detected in the honey dew ofRhopalosiphum padi feeding on seedlings of six wheat cultivars that differed in their concentration of Hx, suggesting that the chemical circulates in the phloem. Neither the aglucone (DIMBOA) nor its main breakdown product were found in any of the honeydew samples. Honey dew production by aphids caged on seedlings of the wheat cultivars and DIMBOA glucoside concentrations in the honeydew followed biphasic curves when plotted against Hx concentration, suggesting passive ingestion of the chemical from the phloem at low Hx concentrations and limited ingestion due to feeding deterrency by Hx in mesophyll cells at high Hx concentrations. The presence of plant toxins such as Hx glucosides in the phloem sap, the main ingesta of aphids, and in the mesophyll cells, has major implications for plant defense, through a feeding deterrent effect during stylet penetration, and deterrency (antixenosis) along with antibiosis during feeding.

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References

  • Argando¯na, V.H., andCorcuera, L.J. 1985. Distribution of hydroxamic acids inZea mays tissues.Phytochemistry 24:177–178.

    Google Scholar 

  • Argandona, V.H., Luza, J.G., Niemeyer, H.M., andCorcuera, L.J. 1980. Role of hydroxamic acids in the resistance of cereals to aphids.Phytochemistry 19:1665–1668.

    Google Scholar 

  • Argandona, V.H., Zuniga, G.E., andCorcuera, L.J. 1987. Distribution of gramine and hydroxamic acids in barley and wheat leaves.Phytochemistry 26:1917–1918.

    Google Scholar 

  • BarrÍa, B.N., Copaja, S.V., andNiemeyer, H.M. 1992. Occurrence of DIBOA in wildHordeum species and relation to aphid resistance.Phytochemistry 31:89–91.

    Google Scholar 

  • Beck, D.L., Dunn, G.M., Routley, D.G., andBowman, J.S. 1983. Biochemical basis of resistance in corn to the corn leaf aphid.Crop Sci. 23:995–998.

    Google Scholar 

  • Bohidar, K., Wratten, S.D., andNiemeyer, H.M. 1986. Effects of hydroxamic acids on the resistance of wheat to the aphidSitobion avenae. Ann. Appl. Biol. 109:193–198.

    Google Scholar 

  • Campos, F., Atkinson, J., Arnason, J.T., Philogène, B.J.R., Morand, P., Werstiuk, N.H., andTimmins, G. 1989. Toxicokinetics of 2,4-dihydroxy-7-methoxy-l,4-benzoxazin-3-one

  • (DIMBOA) in the European com borer,Ostrinia nubilalis (Hübner).J. Chem. Ecol. 15:1989–2001.

  • Copaja, S.V., Barría, B.N., andNiemeyer, H.M. 1991a. Hydroxamic acid content of perennial Triticeae.Phytochemistry 30:1531–1534.

    Google Scholar 

  • Copaja, S.V., Niemeyer, H.M., andWratten, S.D. 1991b. Hydroxamic acid levels in Chilean and British wheat seedlings.Ann. Appl. Biol. 118:223–237.

    Google Scholar 

  • Cuevas, L., Niemeyer, H.M., andPerez, F.J. 1990. Reaction of DIMBOA, a resistance factor from cereals, withα-chymotrypsin.Phytochemistry 29:1429–1432.

    Google Scholar 

  • Cuevas, L.,Niemeyer, H.M., andJonsson, L.M.V. 1992. Partial purification and characterization of a hydroxamic acid glucoside β-D-glucosidase from maize.Phytochemistry. In press.

  • Givovich, A., andNiemeyer, H.M. 1991. Hydroxamic acids affecting barley yellow dwarf virus transmission by the aphidRhopalosiphum padi.Entomol. Exp. Appl 59:79–85.

    Google Scholar 

  • Hofman, J., andHofmanova, O. 1969. 1,4-Benzoxazine derivatives in plants. Sephadex fraction-ation and identification of a new glucoside.Eur. J. Biochem. 8:109–112.

    Google Scholar 

  • Klun, J.A., andRobinson, J.F. 1969. Concentration of two 1,4-benzoxazinones in dent corn at various stages of development of the plant and its relation to resistance of the host plant to the European Corn Borer.J. Econ. Entomol. 62:214–220.

    Google Scholar 

  • Long, B.J., Dunn, G.M., Bowman, J.S., andRoutley, D.G. 1977. Relationship of hydroxamic acid content in corn and resistance to the corn leaf aphid.Crop Sci. 17:55–58.

    Google Scholar 

  • Lyons, P.C., Hipskind, J.D., Wood, K.V., andNicholson, R.L. 1988. Separation and quantification of cyclic hydroxamic acids and related compounds by high-pressure liquid chromatography.J. Agric. Food Chem. 36:57–60.

    Google Scholar 

  • Molyneux, R.J., Campbell, B.C., andDreyer, D.L. 1990. Honeydew analysis for detecting phloem transport of plant natural products. Implications for host-plant resistance to sap-sucking insects.J. Chem. Ecol. 16:1899–1909.

    Google Scholar 

  • Niemeyer, H.M. 1988a. Hydroxamic acids (4-hydroxy-1,4-benzoxazin-3-ones), defence chemicals in the Gramineae.Phytochemistry 26:3349–3358.

    Google Scholar 

  • Niemeyer, H.M. 1988b. Hydroxamic acid content ofTriticum species.Euphytica 37:289–293.

    Google Scholar 

  • Niemeyer, H.M., Calcaterra, N.B., andRoveri, O.A. 1986. Inhibition of mitochondrial energylinked reactions by 2,4-dihydroxy-7-methoxy-l,4-benzoxazin-3-one (DIMBOA), a hydroxamic acid from Gramineae.Biochem. Pharmacol. 35:3909–3914.

    Google Scholar 

  • Niemeyer, H.M., Pesel, E., Copaja, S.V., Bravo, H.R., Franke, S., andFrancke, W. 1989a. Changes in hydroxamic acid levels of wheat plants induced by aphid feeding.Phytochemistry 28:447–449.

    Google Scholar 

  • Niemeyer, H.M., Pesel, E., Franke, S., andFrancke, W. 1989b. Ingestion of the benzoxazinone DIMBOA from wheat plants by aphids.Phytochemistry 28:2307–2310.

    Google Scholar 

  • Niemeyer, H.M.,Copaja, S.V., andBarria, B.N. 1992. Sources of hydroxamic acids, secondary metabolites in wheat confering resistance against aphids.Hereditas. In press.

  • Pollard, D.G. 1973. Plant penetration by feeding aphids (Hemiptera: Aphidoidea): A review.Bull. Entomol. Res. 62:631–714.

    Google Scholar 

  • Thackray, D.J., Wratten, S.D., Edwards, P.J., andNiemeyer, H.M. 1990. Resistance to the aphidsSitobion avenae andRhopalosiphum padi in Gramineae in relation to hydroxamic acid level.Ann. Appl. Biol. 116:573–582.

    Google Scholar 

  • Xie, Y.S., Arnason, J.T., Philogène, B.J.R., andLambert, J.D.H. 1990. Role of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) in the resistance of maize to western corn rootworm,Diabrotica virgifera virgifera (LeConte) (Coleoptera: Chrysomelidae).Can. Entomol. 122:1177–1186.

    Google Scholar 

  • Zu¯niga, G.E., Argando¯na, V.H., Niemeyer, H.M., andCorcuera, L.J. 1983. Hydroxamic acid content in wild and cultivated Gramineae.Phytochemistry 22:2665–2668.

    Google Scholar 

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Givovich, A., Morse, S., Cerda, H. et al. Hydroxamic acid glucosides in honeydew of aphids feeding on wheat. J Chem Ecol 18, 841–846 (1992). https://doi.org/10.1007/BF00988324

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  • DOI: https://doi.org/10.1007/BF00988324

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