2α,5α-Epoxy-1,2-dihydroakuammilan-17-oic acid methyl ester

Description

An Alstonia alkaloid obtained from A. scholaris R. Br., this base also occurs in Rauwolfia vornitora. It has [α]_D - 47° (CHCI3). The ultraviolet spectrum in neutral solution (EtOH) has absorption maxima at 237 and 287 mil, while in acidic solution (perchloric acid), there are absorption maxima at 239, 244 and 305 mil. A methoxycarbonyl group, an alkyl group and an ether bridge are present in the molecule. The picrate is obtained as light yellow crystals with m.p. 172- 4°C (dec.) and the methiodide has m.p. 235-7°C.

The Uses of 2α,5α-Epoxy-1,2-dihydroakuammilan-17-oic acid methyl ester

Picrinine is a monoterpenoid indole alkaloid extracted from Ochrosia elliptica, displaing the enhancement of immunomodulatory activity and apaptosis inducing in the A549 cell lines.

References

Preparation:
Britten, Smith.,J. Chern. Soc., 3850 (1963)
Isolation:
Chatterjee et al., Tetrahedron Lett., 3633 (1965)