Isoquinoline-derived alkaloids from the bark of Guatteria olivacea (Annonaceae)

Phytochemical investigation of the bark of Guatteria olivacea R. E. Fries (Annonaceae) led to the isolation and identification of ten isoquinoline-derived alkaloids, including three phenanthrenes, atherosperminine, argentinine, and atherosperminine N-oxide; three aporphines, asimilobine, puterine, a...

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Published in:Biochemical systematics and ecology 2020-10, Vol.92, p.104105, Article 104105
Main Authors: de Souza Araújo, Morgana, Araújo da Silva, Felipe Moura, Ferreira Koolen, Hector Henrique, Costa, Emmanoel Vilaça
Format: Article
Language:English
Subjects:
Aporphinoid alkaloids
Chemotaxonomy
Guatteria olivacea
Isoquinoline-derived alkaloids
Phenanthrene alkaloids
Tetrahydroprotoberberine alkaloids
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Summary:Phytochemical investigation of the bark of Guatteria olivacea R. E. Fries (Annonaceae) led to the isolation and identification of ten isoquinoline-derived alkaloids, including three phenanthrenes, atherosperminine, argentinine, and atherosperminine N-oxide; three aporphines, asimilobine, puterine, and discoguattine; two oxoaporphines, liriodenine and oxoputerine; and two tetrahydroprotoberberines, corypalmine and discretine. All these alkaloids are described for the first time in G. olivacea and their chemotaxonomic significance was discussed. The structure elucidation of these isolated alkaloids was established by extensive analyses of 1D and 2D NMR spectroscopy in combination with MS. The NMR data for atherosperminine, argentinine, and atherosperminine N-oxide were reviewed. [Display omitted] •Ten isoquinoline-derived alkaloids were isolated and identified in the bark of Guatteria olivacea (Annonaceae).•The isolated alkaloids are described for the first time in Guatteria olivacea.•Discoguattine is reported for the second time in the Annonaceae.•Alkaloids support the close relationship with other Guatteria species.•The NMR data for atherosperminine, argentinine, and atherosperminine N-oxide were reviewed.
ISSN:0305-1978
1873-2925
DOI:10.1016/j.bse.2020.104105