ZIZYPHINE C

Description

A further series of peptide alkaloids has recently been isolated from Zizyphus oenopZea where they occur primarily in the stem bark. This base is an amorphous powder having the following specific rotations: [α]²⁰_D - 331 ° ± 5° (c 0.10, CHCI3) and [α]²⁰_D - 343° ± 5° (c 0.10, MeOH). The ultraviolet spectrum in MeOH has absorption maxima at 266 and 318 nm. Oxidation with osmium tetroxide yields aminoaldehyde which has specific rotations of [α]²⁰_D - 64° ± 1° (c 0.10, CHCI3) and [α]²⁰_D - 51 ° ± 1° (c 0.10, MeOH). The ultraviolet spectrum has absorption maxima at 255 and 346 nm with a shoulder at 212 nm. Hydrolysis with N-HCl in a sealed tube at 110°C furnishes butyric acid, isoleucine, proline and N,N-dimethylphenylalanine.

References

Cassells et at., Tetrahedron, 30, 2461 (1974)