Neutral compounds and alkaloids of Zanthoxylum ocumarense

Phytochemistry
1972.0

Abstract

The genus Zanthoxylum consists of more than eighty plant species, found principally in Africa, America and Australia. Benzene extraction of the bark of Z. ocumareme collected near the coast of Venezuela (Henry Pittier National Park) followed by alumina chromatography yielded n-alkanes (C21H44 to C28H58), a triterpenoid mixture with major component lupeol, β-amyrin, and two aromatic amides identified as (±)-N-benzoyl[2-hydroxy-2(4'-methoxyphenyl)]ethylamine (tembamide, I) and (±)-N-cinnamoyl[2-hydroxy-2(4'-methoxyphenyl)]ethylamine (aegeline, II). Re-extraction of the bark with hot methanol yielded a mixture of three quaternary bases (N-methyl-a(-)-canadine, (+)-laurifoline, cheleritrine), two alkaloids (III and IV), and a flavonoid glycoside identified as hesperedin. The compounds were identified by methods including GLC, mass spectral analysis, hydrogenation, preparative TLC, comparison of physical and spectral properties (UV, IR, NMR), elemental analysis, direct comparison with authentic samples, and derivative preparation. Unfortunately, due to the instability of alkaloid III and low yield of alkaloid IV, further work is needed.

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