Constituents of Aniba hostmanniana

Phytochemistry
1972.0

Abstract

Aniba hostmanniana (Nees) Mez is an arboreous species of Lauraceae which grows in the Amazon region. The bark contains an essential oil (0.8 %) which was separated by GLC into terpenes (1.2 %), sesquiterpenes (4.0 %), 3,4-dimethoxyallylbenzene (0.3 %) and 2,4,5-trimethoxyallylbenzene (94.5 %). The wood contains, besides a similar essential oil (1.3 %) composed of terpenes (0.5 %), sesquiterpenes (0.9 %) and 2,4,5-trimethoxyallylbenzene (98.6 %), also sitosterol and N-[β-(4-methoxyphenyl)-ethyl]-3,4,5-trimethoxycinnamamide. Volatile constituents were classified as terpenes and sesquiterpenes according to GLC retention times. 3,4-Dimethoxyallylbenzene and sitosterol were identified by direct comparison with authentic samples. The trimethoxyallylbenzene was identified through its PMR spectrum. The remaining constituent, C21H25NO5, was recognized as an amide: PMR data defined it as N-[β-(4-methoxyphenyl)-ethyl]-3,4,5-trimethoxycinnamamide, confirmed by mass spectrum and hydrolysis products (β-(4-methoxyphenyl)-ethylamine and 3,4,5-trimethoxybenzoic acid). Derivation from a cinnamic acid type precursor is apparent in numerous constituents of Aniba species and the entire Lauraceae family. In contradistinction, alkaloids based on the C6-C3-N-C6-C3-skeleton, though extremely widespread in the Lauraceae, have not yet been located in the genus Aniba.

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