Caryomene olivascens

Caryomene olivascens (Menispermaceae) afb 6,163 87 Guatteria discolor (Annonaceae) jnp 47,353 84 Xylopia vieillardi (Annonaceae) jnp 54,466 91... 

Caryomene olivascens (Menispermaceae) afb 6,163 87 Duguetia obovata (Annonaceae) jnp 46,862 83 Guatteria discolor (Annonaceae) jnp 46,862 83 Guatteria scandens (Annonaceae) jnp 46,335 83 Pachypodanthium staudtii (Annonaceae) pmp 11,315 77 Stephania suberosa (Menispermaceae) phy 26, 547 87 Xylopia discreta (Annonaceae) bull 1 Xylopia vieillardi (Annonaceae) jnp 54, 466 91... 

Simple isoquinolines are not found in the Menispermaceae of South America. The isoquinolone thalifoline (1) was identified from Abuta pahni [32], Benzyltetrahydroisoquinolines are the biogenetic precursors for aporphines, proaporphines, and oxoaporphines. Yet the only such compound isolated from South American Menispermaceae is (+) coclaurine (2) obtained from Sciadotema eichleriam [52] and Caryomene olivascens [37-38]. The chemistry of simple isoquinolines [65], isoquinolones [66], and benzyltetrahydroisoquinolines [67] have been reviewed. 

There are three alkaloids in this group, two of which are the secobisbenzylisoquinolines auroramine (390) and maroumine (391). These two bases, that have only been found as metabolites of Gyrocarpus americanus (Hemandiaceae), differ only in the nature of their C(6 ) groups, with the former being a methoxy while the latter is a hydroxy. The remaining alkaloid is 1.2-dehydro-2-norlimacusine (291) from Caryomene olivascens (Menispermaceae). 

There are only two alkaloids that constitute this small subgroup, but both bear an identical oxygenation pattern. Berbacolorflammine (218) is monoquatemary benzylisoquinoline at N-2, while caryolivine (281) has a tertiary nitrogen atom in a benzyisoquinoline system. Each alkaloid has only been isolated from a single plant, berbacolorflammine (218) from Pycnarrhena longifolia (Menispermaceae) and caryolivine (281) from Caryomene olivascens (Menispermaceae). 

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