Vindoline-obtained from the plant Catharanthus roseus (L.) G. Don (Apocynaceae)

C. Vindoline


Biological Sources It is obtained from the plant Catharanthus roseus (L.) G. Don (Apocynaceae) (Periwinkle, Madagascar or Cape Periwinkle; Old Maid). It is found to be the major alkaloid from the leaves of Vinca rosea Linn. (Apocynaceae).
Chemical Structure

Vindoline
(2β, 3β, 4β, 5α,12β, 19α)-4-(Acetyloxy)-6, 7-didehydro-3-hydroxy-16-methoxy-1 methylaspidospermidine-3-carboxylic acid methyl ester; (C25H32N2O6).
Isolation It is isolated from the leaves of Vinca rosea by the method suggested by Gorman et al.*
Characteristic Features
1. Vinodoline is obtained in two forms: first, as needles from a mixture of acetone and petroleum ether having mp 164-165°C; and secondly, as prisms having mp 174-175°C.
2. It has [α]20D - 18° (chloroform) and dissociation constant pKa 5.5 in 66% DMF.
3. It has uvmax (ethanol): 212, 250, 304 nm (log ε 4.49, 3.74, 3.57).
Identification Tests It gives specific derivatives as.
1. Vindoline Hydrochloride (C25H32N2O6.HCl): It is obtained as crystals from acetone having mp 161-164°C.
2. Demethoxy Vindoline (C24H30N2O5) (Vindorosine, Vindolidine): It is obtained as needles from benzene and petroleum ether having mp 167°C. It has [α]16D -31° (Chloroform); and uvmax (methanol): 250, 302 nm (log ε 3.98, 3.52).

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