Side chain functionalization of cholesterol in the biosynthesis of solasodine in Solanum laciniatum |
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Authors: | Rudolf Tschesche H.Rainer Brennecke |
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Affiliation: | Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str. 1, D-5300 Bonn 1, W. Germany |
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Abstract: | (25R)-26-Amino-cholesterol-[7α-3H], (25R)-26-amino-5-cholestene-3β,16β-diol-[7α-3H] and (25R)-26-acetylamino-5-cholestene-3β,16β-diol-[7α-3H] administered to Solanum laciniatum were converted into solasodine. The results indicate that in the biosynthesis of solasodine the introduction of nitrogen occurs immediately after the hydroxylation at C-26 and before a further oxidation of the side chain of cholesterol. The next step after the amination at C-26 is not hydroxylation at the 16β-position but probably the functionalization of C-22. |
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Keywords: | Solanaceae biosynthesis steroidal alkaloids solasodine. |
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