Grahamines A-E, cyclobutane-centered tropane alkaloids from the aerial parts of Schizanthus grahamii |
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| Authors: | Cretton Sylvian Bartholomeusz Trixie A Humam Munir Marcourt Laurence Allenbach Yves Jeannerat Damien Muñoz Orlando Christen Philippe |
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| Institution: | School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Quai Ernest-Ansermet 30, CH-1211 Geneva 4, Switzerland. |
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| Abstract: | Schizanthus grahamii is an endemic Chilean plant that is known to contain tropane alkaloids. Five new alkaloids, grahamines A-E (1-5), were isolated and characterized by extensive spectroscopic analysis. Their structures were determined to be 2-{(3α-hydroxytropo-6β-yl)oxy]carbonyl}-2-methyl-3-{((6β-angeloyloxy)-3α-yl)oxy]carbonyl}-4-phenylcyclobutanecarboxylic acid (1), 2-{(3α-hydroxytropo-6β-yl)oxy]carbonyl}-2-methyl-3-{((6β-tigloyloxy)-3α-yl)oxy]carbonyl}-4-phenylcyclobutanecarboxylic acid (2), 1-methyl-2-{(3α-hydroxytropo-6β-yl)oxy]carbonyl}-4-{((6β-angeloyloxy)-3α-yl)oxy]carbonyl}-3-phenylcyclobutanecarboxylic acid (3), 1,2-bis{(3α-hydroxytropo-6β-yl)oxy]carbonyl}-2-methyl-3-{((6β-angeloyloxy)-3α-yl)oxy]carbonyl}-4-phenylcyclobutanecarboxylate (4), and 1-{(3α-mesaconyloxytropo-6β-yl)oxy]carbonyl}-2-{(3α-hydroxytropo-6β-yl)oxy]carbonyl}-2-methyl-3-{((6β-angeloyloxy)-3α-yl)oxy]carbonyl}-4-phenylcyclobutanecarboxylate (5). |
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