(+)-N-Formylnorglaucine Rotamers from Unonopsis stipitata Diels

(+)‐N‐formylnorglaucine (1), an aporphine alkaloid containing a formyl group linked to the heterocyclic nitrogen, was isolated from the leaves of Unonopsis stipitata, an Amazon medicinal plant. The chemical structure was characterized based on 1D‐ and 2D‐NMR spectroscopy and HR‐ESI‐MS. NMR spectra r...

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Published in:Helvetica chimica acta Vol. 99; no. 7; pp. 494 - 498
Main Authors: da Silva, Felipe M. A., da Silva Filho, Francinaldo A., de Lima, Bruna R., de Almeida, Richardson A., Mendonça, Dácio M., Pereira Junior, Raimundo C., Dutra, Lívia M., Barison, Andersson, Koolen, Hector H. F., de Souza, Afonso D. L., Pinheiro, Maria Lúcia B.
Format: Journal Article
Language:English
Published: Zürich Blackwell Publishing Ltd 01-07-2016
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Summary:(+)‐N‐formylnorglaucine (1), an aporphine alkaloid containing a formyl group linked to the heterocyclic nitrogen, was isolated from the leaves of Unonopsis stipitata, an Amazon medicinal plant. The chemical structure was characterized based on 1D‐ and 2D‐NMR spectroscopy and HR‐ESI‐MS. NMR spectra revealed that 1 is composed of two rotamers (1a and 1b) in a ratio of approximately 2:1. In addition, the fragmentation behavior of 1 displayed an unusual fragmentation pattern compared to regular aporphine alkaloids. Thus, this compound is reported for the first time as a natural product in this study.
Bibliography:FAPEAM
istex:FA6DEAE84AD019854EADD4835F8802F0D9BD61BE
CNPq
ark:/67375/WNG-TW3TJT9J-R
ArticleID:HLCA201600030
FINEP
CAPES
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201600030