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Planta Med 1980; 40(10): 109-119
DOI: 10.1055/s-2008-1074947
Research Articles

© Georg Thieme Verlag Stuttgart · New York

In Vivo and In Vitro Evidence for N-Methylation as the Second Pathway-Specific Step in Ergoline Biosynthesis1

H. Otsuka, F. R. Quigley, D. Gröger, J. A. Anderson, H. G. Floss
  • Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907, U.S.A.
1 On the occasion of his 80th birthday dedicated to Professor Kurt Mothes, who initiated both the senior authors into the field of ergot research.
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Publication History

Publication Date:
29 April 2008 (online)

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Abstract

Experiments with precursors intramolecularly double-labeled with 15N and deuterium have shown that N-methyl-4-(γ, γ-dimethylallyl)tryptophan (Ib), but not its decarboxylation product, is an intact precursor of the tetracyclic ergoline elymoclavine (IIIb). An N-methyltransferase has been detected in cell-free extracts of Claviceps which catalyzes the transfer of the S-methyl group of S-adenosylmethionine to the amino group of 4-(γ, γ-dimethylallyl)tryptophan (Ia). These results strongly indicate that N-methylation of la is the second pathway-specific step in ergoline biosynthesis and they imply that pyridoxal phosphate cannot be involved as cofactor in the decarboxylation and C-ring closure steps in this biosynthesis.

Key Word Index

Claviceps - Alkaloids - Ergoline Biosynthesis.

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