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Related Experiment Videos

Polyazamacrolides from ladybird beetles: ring-size selective oligomerization

F C Schroeder1, S R Smedley, L K Gibbons

  • 1Baker Laboratory, Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14853, USA.

Proceedings of the National Academy of Sciences of the United States of America
|November 13, 1998
PubMed
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The 24-pointed ladybird beetle

Area of Science:

  • Chemical Ecology
  • Insect Biochemistry
  • Natural Product Chemistry

Background:

  • Ladybird beetles (Coccinellidae) produce defensive secretions for protection.
  • Pupal secretions are less studied than adult secretions in ladybird beetles.
  • Subcoccinella vigintiquatuorpunctata is a ladybird beetle species with a distinctive 24-point pattern.

Purpose of the Study:

  • To elucidate the chemical composition of the pupal defensive secretion of Subcoccinella vigintiquatuorpunctata.
  • To determine the structures and absolute configurations of the macrocyclic polyamines involved.
  • To compare the secretion with those of related ladybird beetle species.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy for structural elucidation.

Related Experiment Videos

  • High-Performance Liquid Chromatography coupled with Mass Spectrometry (HPLC-MS) for analysis.
  • Synthesis of derivatives and comparison with natural products to determine absolute configuration.

    • Main Results:

    • The secretion is dominated by dimeric macrocycles (30-membered) derived from two specific building blocks: 11-(2-hydoxyethylamino)-5-tetradecenoic acid and 11-(2-hydoxyethylamino)-5,8-tetradecadienoic acid.
    • Cyclic trimers (45-membered macrocycles) of these building blocks were also identified in smaller quantities.
    • The all-S absolute configuration of the macrocycles was established.
    • The composition suggests insects carefully control the oligomerization of building blocks.

    Conclusions:

    • The pupal defensive secretion of S. vigintiquatuorpunctata is chemically complex, featuring macrocyclic polyamines.
    • The structural diversity and stereochemistry provide insights into insect chemical defense mechanisms.
    • Comparison with related species highlights the evolutionary control of building block oligomerization in ladybird beetle secretions.