Erowid References Database
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Lin CCL, Blair GE, Cassady JM, Groeger D, Maier W, Floss HG.
“Biosynthesis of Ergot Alkaloids, Synthesis of 6-Methyl-8-acetoxymethylene-9-ergolene and Its Incorporation into Ergotoxine by Claviceps.”.
J.Org.Chem.. 1973;38(12):2249-51.
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Abstract
The biosynthesis of ergotoxine (III), containing the lysergic acid moiety (III, R=OH) has been studied. Treatment of elymoclavine (I) with DMSO -Ac2O gave its O-acetate and also 6-methyl-8 - acetoxymethylene-9-ergolene (II), the structure of which was established by UV and NMR data and by LiAlH4 reduction to lysergol. All attempts to convert (I) or (II) to lysergaldehyde (III, R=H) failed. A tritiated sample of (II) was prepared by oxidation of (indole-3H)-(I). Tritium-labeled (I), its O-acetate and (II) were each fed to shake-cultures of Claviceps purpurea strain PETTY 695. After 24 hours the alkaloid content of the cultures was determined calorimetrically, the ergot-oxine was isolated and hydrolyzed to lysergic acid. It was found that (I) and (II) were incorporated to an approximately equal extent (about 1.5%), whilst (I)-O-acetate was incorporated to an extent of 4.15%. Biosynthetic mechanisms are discussed.
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