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Chembiochem. 2005 Jun;6(6):1016-22.

Biosynthetic precursors of fungal pyrrolizidines, the loline alkaloids.

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Department of Plant Pathology, University of Kentucky, 1405 Veterans Drive, Lexington, KY 40546-0312, USA.

Erratum in

  • Chembiochem. 2006 Mar;7(3):404.


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 gamma-substitution reaction.

[Indexed for MEDLINE]

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