Skip to main content
Log in

High-pressure liquid chromatographic techniques for the separation and quantification of norsesquiterpenes from gyrinids

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

A rapid, sensitive, stable, and quantitative high-pressure liquid chromatographic technique was developed for the analysis of the norsesquiterpenes, gyrinidal, isogyrinidal, gyrinidone, and gyrinidione. Methods were developed for both normal-phase (μPorasil) and reverse-phase (μBondapak) columns. The applicability of this technique was demonstrated when the norsesquiterpenes of the defensive secretions of the water beetleGyrinus frosti Fall were isolated and identified as gyrinidal and isogyrinidal. This method was then used for the quantification of the norsesquiterpene titer ofG. frosti andDineutus assimilis (Kirby).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Benfield, E. 1972. A defensive secretion ofDineutes discolor (Coleoptera: Gyrinidae).Ann. Entomol. Soc. Am. 65:1324–1327.

    Google Scholar 

  • Meinwald, J., Opheim, K., andEisner, T. 1972. Gyrinidal: A sesquiterpenoid aldehyde from the defensive glands of gyrinid beetles.Proc. Natl. Acad. Sci. U.S.A. 69:1208–1210.

    PubMed  Google Scholar 

  • Miller, J., andMumma, R. 1974. Seasonal quantification of the defensive steroid titer ofAgabus seriatus (Coleoptera: Dytiscidae).Ann. Entomol. Soc. Am. 67(6):850–852.

    Google Scholar 

  • Miller, J., andMumma, R. 1976a. Physiological activity of water beetle defensive agents. I. Toxicity and anesthetic activity of steroids and norsesquiterpenes administered in solution to the minnowPimephales promelas Raf.J. Chem. Ecol. 2(2):115–130.

    Google Scholar 

  • Miller, J., andMumma, R. 1976b. Physiological activity of water beetle defensive agents. II. Absorption of selected anesthetic steroids and norsesquiterpenes across gill membranes of the minnowPimephales promelas Raf.J. Chem. Ecol. 2(2):131–146.

    Google Scholar 

  • Miller, J., Hendry, L., andMumma, R. 1975. Norsesquiterpenes as defensive toxins of whirligig beetles (Coleoptera: Gyrinidae).J. Chem. Ecol. 1(1):59–82.

    Google Scholar 

  • Schildknecht, H., Neumaier, H., andTauscher, B. 1972a. Gyrinal, die Pygidialdrüsen Substanz der Taumelkäfer (Coleoptera: Carabidae).Liebigs Ann. Chem. 756:155–161.

    Google Scholar 

  • Schildknecht, H., Tauscher, B., andDraub, D. 1972b. Der Duftstoff des Taumelkäfer Gyrinus narator L.Chem. Z. 96:33–35.

    Google Scholar 

  • Wheeler, J., Oh, S., Benfield, E., andNeff, S. 1972. Cyclo pentanoid norsesquiterpenes from gyrinid beetles.J. Am. Chem. Soc. 94:7589–7590.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Newhart, A.T., Mumma, R.O. High-pressure liquid chromatographic techniques for the separation and quantification of norsesquiterpenes from gyrinids. J Chem Ecol 4, 503–510 (1978). https://doi.org/10.1007/BF00988914

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00988914

Key words

Navigation