Azamacrolides: a family of alkaloids from the pupal defensive secretion of a ladybird beetle (Epilachna varivestis).

@article{Attygalle1993AzamacrolidesAF,
  title={Azamacrolides: a family of alkaloids from the pupal defensive secretion of a ladybird beetle (Epilachna varivestis).},
  author={Athula B. Attygalle and Kevin D. Mccormick and Curtis L. Blankespoor and Thomas Eisner and Jerrold Meinwald},
  journal={Proceedings of the National Academy of Sciences of the United States of America},
  year={1993},
  volume={90 11},
  pages={
          5204-8
        }
}
Defensive droplets from glandular hairs of the pupa of the Mexican bean beetle, Epilachna varivestis, contain a group of structurally novel alkaloids, the azamacrolides. The major constituent of this secretion, epilachnene, is shown to be (5Z)-11-propyl-12-azacyclotetradec-5-en-14-olide. The secretion also contains an epilachnadiene and trace amounts of three closely related components. 

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References

SHOWING 1-2 OF 2 REFERENCES
Hemorrhage in a Coccinellid Beetle and Its Repellent Effect on Ants
TLDR
Special refinements of the bleeding mechanism of the Mexican bean beetle are described, and the defensive effectiveness of the mechanism against ants is demonstrated, suggesting that Ants may have provided a major selective force in the evolution of this mechanism.