Pyrrolidinoindoline alkaloids from Psychotria oleoides and Psychotria lyciiflora.
The chemical study of two Rubiaceae from New Caledonia, Psychotria lyciiflora and Psychotria oleoides, led to the isolation of several pyrrolidinoindoline alkaloids. Two dimers, the known meso-chimonanthine (9) and the new Nb-desmethyl-meso-chimonanthine (5), and a known trimer, hodgkinsine (1), have been isolated from P. lyciiflora. Hodgkinsine (1), quadrigemine C (2), isopsychotridine B (3), psychotridine (4), and three new alkaloids, quadrigemine I (6), oleoidine (7), and caledonine (8), have been isolated from P. oleoides. Structural assignments of the compounds were based on mass spectra analysis and 2D NMR experiments. A tentative stereochemical determination is made from 2D NMR experiments, circular dichroism study and chemical correlations. Some of these compounds are functional antagonists of somatostatine (SRIH).
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Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex France.
Guéritte
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Laprévote
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Serani
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Martin
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Sévenet
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Potier
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D000470:Alkaloids / Q000302:isolation & purification*; D007211:Indoles / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D009510:New Caledonia; D018515:Plant Leaves / Q000737:chemistry; D011758:Pyrroles / Q000302:isolation & purification*; D019666:Rubiaceae / Q000737:chemistry*; D013004:Somatostatin / Q000037:antagonists & inhibitors
D000470:Alkaloids; D007211:Indoles; C516206:N(b)-desmethylchimonathine; D011758:Pyrroles; D013004:Somatostatin