Biosynthesis of a defensive insect alkaloid: Epilachnene from oleic acid and serine

Athula B. Attygalle, Curtis L. Blankespoor, Thomas Eisner, Jerrold Meinwald

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

The biosynthesis of the azamacrolide epilachnene by the coccinellid beetle Epilachna varivestis has been studied with 2H-labeled oleic acid, 2H- labeled L-serine, and 13C, 15N-labeled L-serine. The incorporation of these precursors into epilachnene defines the origin of the alkaloid's entire carbon/nitrogen skeleton. GC/MS and GC/IR studies of alkaloid produced by Epilachna fed with deuteriated oleic acid show that oleic acid loses four carbon atoms from its carboxyl end during the biosynthesis. Other details, including the mechanism of carbon-nitrogen bond formation between the fatty acid and amino acid moieties, remain to be established.

Original languageEnglish
Pages (from-to)12790-12793
Number of pages4
JournalProceedings of the National Academy of Sciences of the United States of America
Volume91
Issue number26
DOIs
StatePublished - 20 Dec 1994

Keywords

  • Coccinellidae
  • Insecta
  • macrolide
  • stable isotope labeling

Fingerprint

Dive into the research topics of 'Biosynthesis of a defensive insect alkaloid: Epilachnene from oleic acid and serine'. Together they form a unique fingerprint.

Cite this