Five new alkaloids from the leaves of Remijia peruviana

Three new indolylquinuclidine-type alkaloids, remijinine (1), epiremijinine (2), and 5-acetyl-apocinchonamine (3), and two new cinchonine-derived alkaloids, N-acetyl-deoxycinchonicinol (4) and N-acetyl-cinchonicinol (5), as well as the known alkaloids quinamine, conquinamine, cinchonine, and quinidi...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2004-10, Vol.67 (10), p.1667-1671
Main Authors: Diaz, J.G, Sazatornil, J.G, Lopez Rodriguez, M, Ruiz Mesia, L, Vargas Arana, G
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Alkaloids - isolation & purification
Biological and medical sciences
Crystallography, X-Ray
General pharmacology
Indoles - chemistry
Indoles - isolation & purification
Medical sciences
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Peru
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plant Leaves - chemistry
Plants, Medicinal - chemistry
Rubiaceae - chemistry
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Summary:Three new indolylquinuclidine-type alkaloids, remijinine (1), epiremijinine (2), and 5-acetyl-apocinchonamine (3), and two new cinchonine-derived alkaloids, N-acetyl-deoxycinchonicinol (4) and N-acetyl-cinchonicinol (5), as well as the known alkaloids quinamine, conquinamine, cinchonine, and quinidine were isolated from the leaves of Remijia peruviana. The structures of the new alkaloids were elucidated on the basis of spectroscopic analysis, including homonuclear and heteronuclear correlation NMR experiments (COSY, ROESY, HMQC, and HMBC). The relative configuration at C-7 for remijinine (1) and, in consequence, for epiremijinine (2) was established by X-ray crystal structure analysis of the former.
ISSN:0163-3864
1520-6025
DOI:10.1021/np040053k