Tomatidine-obtained from the roots of Rutgers tomato plant (Lycopersicon esculentum)

A.2 Tomatidine


Biological Source It is obtained from the roots of Rutgers tomato plant [Lycopersicon esculentum Mill., cultivar. “Rutgers”] (Solanaceae) (Tomato).
Chemical Structure (3β, 5α, 22β, 25 S)-Spirosolan-3-ol; (C27H45NO2).
Tomatidine

Characteristic Features
1. It is obtained as plates from ethyl acetate having mp 202-206°C.
2. It specific rotation [α ]D25 + 8o (chloroform).
Isolation It is obtained by the hydrolysis of tomatine to yield a molecule of tomatidine along with 2 moles of D-glucose, 1-mole of D-xylose and 1-mole of D-galactose as depicted below:

tomatine
Identification Test Its hydrochloride derivative (C27H45NO2.HCl) is obtained as crystals from absolute ethanol having mp 265-270°C and [α ]D25  -5o (methanol).

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