Biosynthesis of epilachnene, a macrocyclic defensive alkaloid of the Mexican bean beetle

Athula B. Attygalle, Aleš Svatoš, Martin Veith, Jay J. Farmer, Jerrold Meinwald, Scott Smedley, Andrés González, Thomas Eisner

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The carbon skeleton of the azamacrolide epilachnene, the principal defensive alkaloid of Epilachna varivestis pupae, can be derived from oleic acid and serine. Analytical evidence from three experiments in which insects were fed (2H35)octadecanoic acid, (Z)-9- [11,11,12,12,13,13,14,14,15,15,16,16,17,17,18,18,18-2H17]octadecenoic acid and (Z)-9-[11,11,12,12,13,13,14,14,16,16,17,17,18,18,18-2H15]octadecenoic acid, indicates that only the C-15 methylene group of oleic acid is involved in the mechanism leading to carbon-nitrogen bond formation in epilachnene. Support for this scheme is provided by the observation of an unusual ion at m/z 170 in the electron-ionization mass spectrum of epilachnene, rationalized as CH2=CH-COO-CH2-CH2-NH+=CH-CH2-CH2-CH3.

Original languageEnglish
Pages (from-to)955-966
Number of pages12
JournalTetrahedron
Volume55
Issue number4
DOIs
StatePublished - 22 Jan 1999

Keywords

  • Biosynthesis
  • Insects
  • Labelling
  • Mass spectrometry
  • Natural products

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