Skip to main content
SpringerLink
Log in

Biological activity of enantiomerically pure forms of insect juvenile hormone I and III inBombyx mori

  • Research Articles
  • Published:
Experientia Aims and scope Submit manuscript

Summary

Biological activity of enantiomerically pure juvenile hormones was assayed by topical application on allatectomizedBombyx fourth instar larvae. JHs tested were (10R)-JH I [methyl (2E,6E,10R,11S)-10,11-epoxy-3,11-dimethyl-7-ethyl-2,6-tridecadienoate], (10S)-JH I [methyl (2E, 6E, 10S, 11R)-10,11-epoxy-3,11-dimethyl-7-ethyl-2,6-tridecadienoate], (10R)-JH III [methyl (2E,6E,10R)-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienoate] and (10S)-JH III [methyl (2E,6E,10S)-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienoate]. Among these compounds, natural (10R)-JH I was most active and the dose needed to induce 50% larval molting was 0.04 μg/larva; it was approximately 12,000 times more active than unnatural (10S)-JH I. Though natural (10R)-JH III showed slight biological activity, it was only one three-thousandth of that of (10R)-JH I. Unnatural (10S)-JH III exhibited no biological activity at the levels assayed.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Röller, H., Dahm, K.-H., Sweeley, C. C., and Trost, B. M., Angew. Chem. Int. Ed. Engl.6 (1967) 179.

    Article  Google Scholar 

  2. Schooley, D. A., Analysis of the naturally occurring juvenile hormones — their isolation identification, and titer determination at physiological levels, in: Analytical Biochemistry of Insects, pp. 241–287. Ed. R. B. Turner, Elsevier, Amsterdam 1977.

    Google Scholar 

  3. Meyer, A. S., Hanzmann, E., Schneiderman, H. A., Gilbert, L. I., and Boyette, M., Archs Biochem. Biophys.137 (1970) 190.

    Article  CAS  Google Scholar 

  4. Meyer, A. S., Hanzmann, E., and Minphy, R. C., Proc. natl Acad. Sci. USA68 (1971) 2321.

    Article  Google Scholar 

  5. Judy, K. J., Schooley, D. A., Dunham, L. L., Hall, M. S., Bergot, B. J., and Siddall, J. B., Proc. natl Acad. Sci. USA70 (1973) 1509.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Mori, K., and Fujiwhara, M., Tetrahedron44 (1988) 343.

    Article  CAS  Google Scholar 

  7. Mori, K., and Mori, H., Tetrahedron43 (1987) 4097.

    Article  CAS  Google Scholar 

  8. Kindle, H., Winistorfer, M., and Lanzrein, B., Experientia45 (1989) 356.

    Article  CAS  Google Scholar 

  9. Fain, M. J., and Riddiford, L. M., Biol. Bull.149 (1975) 506.

    Article  CAS  PubMed  Google Scholar 

  10. Hiruma, K., Matsumoto, S., Isogai, A., and Suzuki, A., J. comp. Physiol. B (1984) 154.

  11. Mori, K., and Fujiwhara, M., to be submitted.

  12. Plantevin, G., Bosquet, G., Calvez, B., and Nardon, C., Comp. Biochem. Physiol.86B (1987) 501.

    CAS  Google Scholar 

  13. Kimura, M., Sakurai, S., Nakamachi, T., Nariki, M., Niimi, S., Ohtaki, T., Fujimoto, Y., Hata, F., and Ikekawa, N., Zool. Sci.6 (1989) 121.

    CAS  Google Scholar 

  14. Sakurai, S., J. Insect Physiol.29 (1983) 919.

    Article  CAS  Google Scholar 

  15. Ohtaki, T., Takeuchi, S., and Mori, K., Japan J. med. Sci. Biol.24 (1971) 251.

    Article  CAS  Google Scholar 

  16. Imai, K., Marumo, S., and Ohtaki, T., Tetrahedron Lett.15 (1976) 1211.

    Article  Google Scholar 

  17. Rountree, D. B., and Bollenbacher, W. E., J. exp. Biol.120 (1986) 41.

    Article  CAS  PubMed  Google Scholar 

  18. Riddiford, L. M., Nature259 (1976) 115.

    Article  CAS  PubMed  Google Scholar 

  19. Hammock, B., Regulation of juvenile hormone titer: Degradation, in: Comprehensive Insect Physiology, Biochemistry and Pharmacology, Vol. 7, p. 431. Eds G. A. Kerkut and L. I. Gilbert. Pergamon, Oxford 1985.

    Google Scholar 

  20. Prestwich, G. D., and Wawrzenczyk, C., Proc. natl Acad. Sci. USA82 (1985) 5290.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Schooley, D. A., and Bergot, B. J., Biochem. biophys. Res. Commun.81 (1978) 743.

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Biology, Faculty of Science, Kanazawa University, 920, Kanazawa, Japan

    S. Sakurai & T. Ohtaki

  2. Department of Agricultural Chemistry, Faculty of Agriculture, The University of Tokyo, Bunkyo-ku, 113, Tokyo, Japan

    H. Mori, M. Fujiwhara & K. Mori

Authors
  1. S. Sakurai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. Ohtaki
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. H. Mori
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. Fujiwhara
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. K. Mori
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sakurai, S., Ohtaki, T., Mori, H. et al. Biological activity of enantiomerically pure forms of insect juvenile hormone I and III inBombyx mori. Experientia 46, 220–221 (1990). https://doi.org/10.1007/BF02027321

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02027321

Key words

Search

Navigation