Summary
Submerged fermentation of Claviceps paspali strain MG-6 was studied with regard to the fate of individual alkaloids in the course of fermentation. Based on liquid-chromatographic data the process can be divided into three phases. The production phase (fermentation days 3–12) is characterized by biosynthesis of the basic genuine alkaloid, lysergic acid alpha-hydroxyethylamide (LAH I). In view of its low stability it becomes epimerized on two asymmetric carbon atoms in the fermentation medium, yielding three other epimers (LAH II–IV). The degradation phase (days 13–18) involves cleavage of LAH I–IV resulting in ergine and erginine. In the post-production phase (days 15–30) the alkaloids succumb to biooxidative reactions that yield mostly 8-hydroxy-derivatives of ergine and erginine. Isolation of paspalic acid 10-hydroxyamide signifies the existence of an alternative biosynthetic pathway for production of simple lysergic acid derivatives.
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Abbreviations
- LAH I:
-
lysergic acid alpha-hydroxyethylamide;
- LAH II:
-
lysergic acid Cα-epihydroxyethylamide
- LAH III:
-
isolysergic acid alpha-hydroxyethylamide
- LAH IV:
-
isolysergic acid cα-epihydroxyethylamide
- PAH:
-
paspalic acid alpha-hydroxyethylamide
- s:
-
singlet
- d:
-
doublet
- t:
-
triplet
- q:
-
quartet
- dd:
-
double of doublets
- mt:
-
multiplet
- dmt:
-
double of multiplets
- br mt:
-
broad multiplet
- J:
-
interaction constant
- TMS:
-
tetramethyl silane
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Bumbová-Linhartová, R., Flieger, M., Sedmera, P. et al. New aspects of submerged fermentation of Claviceps paspali . Appl Microbiol Biotechnol 34, 703–706 (1991). https://doi.org/10.1007/BF00169337
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DOI: https://doi.org/10.1007/BF00169337