N-[10-(13,14-Methylenedioxyphenyl)-7(E),9(Z)-pentadienoyl]-pyrrolidine

Description

A further minor alkaloid found in Piper nigrum, this base may be recrystallized from Et20 when it yields long, slender needles. The ultraviolet spectrum has absorption maxima at 245,261,309 and 343 mil. The configuration about both of the double bonds in the side chain is trans. The structure given above has been confirmed by synthesis.

Definition

ChEBI: Piperyline is a N-acylpyrrolidine that is pyrollidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum. It has a role as a plant metabolite, an apoptosis inducer and an antifungal agent. It is a member of benzodioxoles, a N-acylpyrrolidine, a tertiary carboxamide and a pyrrolidine alkaloid. It is functionally related to an (E,E)-piperic acid.

References

Grewe et ai., Chem. Ber., 103,3752 (1970)