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).

Characteristic Features

1. It is obtained as plates from ethyl acetate having mp 202-206°C.

2. It specific rotation [α ]_D²⁵ + 8^o (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:

Identification Test Its hydrochloride derivative (C₂₇H₄₅NO₂.HCl) is obtained as crystals from absolute ethanol having mp 265-270°C and [α ]_D²⁵  -5^o (methanol).