Page 103 - phytochemistry general program

Steroidal Alkaloids

1. Solanum glucoalkaloids

A number of Solanum species (Solanaceae) contain some glycosidal
alkaloids which may be considered as nitrogen- containing natural products related

to the steroidal cardiac glycosides and/or the steroidal saponins in structure.

These alkaloids contain a typical steroidal structure with an OH group at C3
like the cardiac glycoside which is involved in a glycosidic linkage with one or more

monosaccharide molecules.
Thus, these alkaloids yield upon hydrolysis a basic or nitrogen –containing

steroidal structure as well as one or more monosaccharides.
The best known of these alkaloids is solanine, isolated from Solanum

tuberosum (Potato) and S. lycopersicum (tomato).
Solanine is glycoside derived from the aglycone solanidine which is a tertiary

base of the following structure:

Solanidine

E
N

CD

A5 B
HO

Solanine = (Solanidine - O – Glucosyl-Galactosyl- Rhamnose)

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