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

Proc Natl Acad Sci U S A. 1993 Jun 1;90(11):5204-8. doi: 10.1073/pnas.90.11.5204.

Abstract

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.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / metabolism*
  • Animals
  • Bridged-Ring Compounds / chemistry
  • Bridged-Ring Compounds / isolation & purification
  • Bridged-Ring Compounds / metabolism*
  • Chromatography, Gas
  • Coleoptera / physiology*
  • Coleoptera / ultrastructure
  • Gas Chromatography-Mass Spectrometry
  • Microscopy, Electron, Scanning
  • Molecular Structure
  • Pupa / physiology
  • Pupa / ultrastructure
  • Spectrophotometry, Infrared

Substances

  • Alkaloids
  • Bridged-Ring Compounds
  • epilachnene
  • epilachnadiene