Biosynthetic precursors of fungal pyrrolizidines, the loline alkaloids

Jimmy D. Blankenship, Justin B. Houseknecht, Sitaram Pal, Lowell P. Bush, Robert B. Grossman, Christopher L. Schardl

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

Loline alkaloids are saturated pyrrolizidines with a substituted 1-amino group and an oxygen bridge between C2 and C7, and are insecticidal metabolites of plant-symbiotic fungi (endophytes). Cultures of the endophyte, Neotyphodium uncinatum, incorporated labeled L-proline and L-homoserine into the 1-aminopyrrolizidine, N-formylloline. The A-ring carbons C1-C3 and the N1 were derived from L-homoserine; the B-ring carbons C5-C8 and the ring nitrogen were derived from L-proline. Incorporation of both deuterium atoms from L-[4,4- 2H2]homoserine and feeding tests with labeled L-methionine indicated that L-homoserine incorporation was not achieved via aspartyl semialdehyde or S-adenosylmethionine, but probably involved a highly novel N-C bond-forming γ-substitution reaction.

Original languageEnglish
Pages (from-to)1016-1022
Number of pages7
JournalChemBioChem
Volume6
Issue number6
DOIs
StatePublished - Jun 2005

Keywords

  • Alkaloids
  • Biosynthesis
  • NMR spectroscopy
  • Natural products
  • Nitrogen heterocycles

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry

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