Degradation Products of Ergot Alkaloids

Journal of Natural Products
1991.0

Abstract

Two new metabolites of Claviceps purpurea strain 129/35, (4aS),(10bS)-7 amino-3,4,4a,5,6,10b-hexahydro-2,4-dimethyl-6-oxobenzo[f]quinoline (1) and (4aS),(10bS)-7 amino-3,4,4a,5,6,10b-hexahydro-2-hydroxymethyl-4-methyl-6-oxobenzo[f]quinoline [2], were isolated from the culture broth. It is supposed that these metabolites are products of ergot alkaloid turnover. Ergot alkaloid degradation was described by Robbers (1). A high concentration of inorganic phosphate in saprophytic cultures of Claviceps sp. inhibits alkaloid biosynthesis. It was also shown that this effect (inhibition of alkaloid production) could be initiated at any time during the course of the fermentation. Another effect of inorganic phosphate is an increased activity of alkaloid-degradative enzymes. On the basis of these results Robbers supposed that alkaloid concentration is in a dynamic state, that there is alkaloid turnover, and that the alkaloids cannot be considered simply as end products of metabolism. The analysis of kinetic parameters of a submerged fermentation of clavine alkaloids by Claviceps purpurea 129/35 showed that overall efficiency of the fermentation process was decreased due to a partial degradation of agroclavine and elymoclavine (2). As the first step in search for the alkaloid-degrading system, we aimed at finding the products of this degradation and determining their structure.

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