Steroidal type solanaceae alkaloids

Steroidal alkaloids of the Solanaceae can therefore be divided into two categories based on the aglycone the solanidine- and the solasodine-type alkaloids. The basic skeleton of the former alkaloids is known as solanidane, and that of the latter alkaloids is known as a spirosolane skeleton. 

Solanum steroid alkaloids have been isolated so far from nearly 350 species of the plant families Solanaceae and Liliaceae, in which they generally occur as glycosides. All of the 75 known steroidal alkamines of the Solanum type,... 

Thus, the C2 7-steroid alkaloids with C-nor-D-homo ring system, that is, with a jervane or cevane skeleton, with 18-nor-17j8-methylcholestane skeleton (23-27) or other alterations of the C27-carbon skeleton of cholestane, found in Liliaceae but not yet in Solanaceae, are not included. They are described exhaustively in other volumes of this series by Kupuchan and By (28) as well as by Tomko and Voticky (29). On the other hand, some Veratrum bases, for instance, teinemine and baikeine, belong to the 5o/amim-type alkaloids and are mentioned in this chapter. 

Fig. 3.18 Chemotaxonomy and phylogeny of the Solanaceae. The provisional phylogenetic tree of Fig. 2.2 is shown here again though without terms for the clades in order to have a clear structure in favour of metabolite symbols. Plotted on the tree is the occurrence of three dominant and characteristic classes of secondary metabolites of the Solanaceae family with two subclasses in one case (I) Tropane alkaloids (two subclasses), (11) steroidal alkaloids/glycoalkaloids, (III) with-anoUdes/withasteroids. These metabolites are indicated by the following symbols. Co-occurrence of different classes (rather rare) is also indicated, i.e., by two corresponding symbols. Filled square tropane alkaloids of the structural types T5, T6, and T7-A - T7-B (very poisonous ester alkaloids with a tropic acid residue, e.g., hyoscyamine/atropine, scopolamine and their derivatives). Taxa highlighted by dt filled square may also show co-occurrence with tropane alkaloids of the following subclass according to Table 3.1 however, this is not highlighted in such cases. Open square tropane alkaloids of the structural types T1 - T4, T7-C, and T7-D (ester alkaloids of...

---