ZIZYPHINE D

Description

A further peptide alkaloid found in the extract from the stem bark of Zizyphus oenopZea, this base yields colourless crystals from MeOH-H20 and has specific rotations of [α]²⁰_D + 236° ± 4° (c 0.10, CHCI3) and [α]²⁰_D - 121 ° ± 2° (c 0.10, MeOH). The ultraviolet spectrum in MeOH consists of a single absorption maximum at 274 nm. The N-acetyl derivative is an amorphous powder with no definite melting point, having specific rotations of [α]²⁰_D - 316° ± 5° (c 0.10, CHCI3) and [α]²⁰_D - 285° ± 5° (c 0.10, MeOH). The O,N-diacetyl derivative has also been prepared with specific rotations of [α]²⁰_D - 285° ± 5° (0.10, CHCI3) and [α]²⁰_D - 217° ± 4° (c 0.10, MeOH). Hydrolysis of the alkaloid with 2N-HCI gives isoleucine and 3-hydroxyisoleucine.

References

Cassells etaZ., Tetrahedron, 30, 2461 (1974)