UNCARINE C

Description

Isolated from Uncaria pteropoda, this alkaloid is probably stereoisomeric withMitraphylline (q.v.). It forms colourless plates when crystallized from MeOH and has [α]²⁹_DJ 9 - 102.5° (c 1.0, CHC13). The ultraviolet spectrum in MeOH has an absorption maximum at 246 mp. with a shoulder at 280 mp.. A crystalline picrate, m.p. 143-6°C; [α]_D - 9.6° (c 0.5, EtOH) and a methiodide, m.p. 209-211°C after softening at 204°C; [α]_D - 149° (c 0.53, EtOH) have been prepared. A solution of the alkaloid in pyridine forms an equilibrium mixture with 70 per cent isopteropodine when heated.

Uses

Uncarine C is a compound extracted from Uncaria tomentosa leaves. The compounds extracted from these leaves have exhibited immunomodulating, antiinflammatory and anti-cancer activity, attributed to the presence of tetra/pentacyclic oxindole alkaloids.

Definition

ChEBI: Uncarine C is a member of indolizines.

References

Yeoh, Chan, Morsingh., Tetrahedron Lett., 931 (1966)
Chan, Morsingh, Yeoh., 1. Chem. Soc., C, 2245 (1966)
Stereochemistry: Shamma et al., 1. Amer. Chem. Soc., 89, 1739, 2799 (1967)