Combinatorial Chemistry in Insects: A Library of Defensive Macrocyclic Polyamines-Reference-Cited by-同舟云学术

Combinatorial Chemistry in Insects: A Library of Defensive Macrocyclic Polyamines

Published:1998-07-17 Issue:5375 Volume:281 Page:428-431
ISSN:0036-8075
Container-title:Science
language:en
Short-container-title:Science

Author:

Schröder Frank C.¹,Farmer Jay J.¹,Attygalle Athula B.¹,Smedley Scott R.¹,Eisner Thomas¹,Meinwald Jerrold¹

Affiliation:

1. F. C. Schröder, J. J. Farmer, A. B. Attygalle, J. Meinwald, Baker Laboratory, Department of Chemistry, Cornell University, Ithaca, NY 14853, USA. S. R. Smedley, Department of Biology, Trinity College, Hartford, CT 06106, USA. T. Eisner, Section of Neurobiology and Behavior, Seeley G. Mudd Hall, Cornell University, Ithaca, NY 14853, USA.

Abstract

The pupal defensive secretion of the coccinellid beetle Epilachna borealis is composed principally of a combinatorial library of macrocyclic polyamines. These compounds constitute a previously unrecognized family of natural products, characterized by extremely large-ring lactonic structures derived from a small set of (2-hydroxyethylamino)alkanoic acids. The combinatorial assembly of these simple building blocks generates a high degree of structural diversity, which is further increased by slow, spontaneous intramolecular rearrangement of the macrocycles.

Publisher

American Association for the Advancement of Science (AAAS)

Subject

Multidisciplinary

Reference24 articles.

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3. For a review of the chemical defenses of ladybird beetles see D. Daloze J.-C. Braekman J. M. Pasteels Chemoecology 5/6 173 (1995);

4. King A. G., Meinwald J., Chem. Rev. 96, 1105 (1996).

5. Attygalle A. B., McCormick K. D., Blankespoor C. L., Eisner T., Meinwald J., Proc. Natl. Acad. Sci. U.S.A. 90, 5204 (1993).

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