4-KETOSTEROIDAL SOLANUM ALKALOIDS

Abstract

4-keto steroidal alkaloids are C-27 substances that have a C-4 carbonyl on their steroidal frame, which makes them different from other steroidal alkaloids. Thus far they have only been found in two South American Solanum trees, which contain them in berries, leaves and roots. The most abundant alkaloids of this type in the berries of Solanum hypomallacophyllum Bitter, a venezuelan species, is Solaphyllidine, which has an α-acetyl on C-16 of the steroirdal frame and a 3-hydroxy-methyl-piperidyl side chain. Several derivatives of Solaphyllidine have been found which are: Desacetylsolaphyllidine, Desacetoxysolaphyllidine, Spirosolaphyllidine. On addition some 4-ketosteroidal alkaloids have been found that have a different side nitrogen containing chain,Solamaladine which has a 4-methyl-1-pyrroline side chain. On the other hand a 4-keto alkaloid with a 5.6-dihydro-verazine has been found in the roots and esacetoxysolaphyllidine-3β-O-D-glycopyranoside in the leaves.

Keywords

• solanum hypomalacophyllum bitter
• solaphyllidine
• solaphyllidine derivatives
• solamaladine
• 4-keto-5
• 6-dihydro-[20s]-verazine