Benzylisoquinolines from Ocotea species

Phytochemistry
1975.0

Abstract

The diterpene constituents of three Sideritis species (S. chamaedryfolia, S. hyssopijblia, S. luteola) were investigated. S. chamaedryfolia yielded two known compounds: ent-15kaurene-7α,18-diol (sideridiol) and ent-16-kaurene-3β,7α,18-triol (foliol). S. hyssopijblia gave only a known diterpene: ent-7α-acetoxy-15-kauren-18-ol (siderol). S. luteola yielded three known diterpenic compounds: ent-16-kaurene-3β,7α,18-triol (foliol), ent-3β-acetoxy-16-kaurene-7α,18-diol (sidol) and ent-18-acetoxy-16-kaurene-3β,7α-diol (linearol). All compounds as well as their acetylated derivatives were characterized by physical and spectroscopic (IR, NMR and MS) data and comparison with authentic samples. Additionally, benzylisoquinolines from two Ocotea species (O. macrophylla and Ocotea sp.) were studied. From O. macrophylla, dehydronantenine, (+)-nantenine, (+)-isocoridine and (+)-glaucine were isolated. The structure of dehydronantenine was deduced by spectral data and confirmed by comparison with a synthetic sample. The occurrences of (+)-glaucine in Lauraceae and dehydronantenine in nature were not previously reported. From Ocotea sp., n-tetracosyl ferulate, 1-(p-methoxybenzyl)-6,7-methylenedioxyisoquinoline and 1-(p-methoxybenzyl)-6,7-dimethoxyisoquinoline were isolated. The latter two, though unreported, are consistent with similar alkaloids in Lauraceae.

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