Grahamines A–E, Cyclobutane-Centered Tropane Alkaloids from the Aerial Parts of Schizanthus grahamii

Journal of Natural Products
2011.0

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-{[(3 alpha-hydroxytropo-6 beta-yl)oxy]carbonyl}-2-methyl-3-{[((6 beta-angeloyloxy)-3 alpha-yl)oxy]carbonyl}-4- phenylcyclobutanecarboxylic acid (1), 2-{[(3 alpha-hydroxytropo-6 beta-yl)oxy]-carbonyl}-2-methy1-3-{[((6 beta-tigloyloxy)-3 alpha-yl)oxy]carbonyl}-4-phenylcyclobutanecarboxylic acid (2), 1-methyl-2-{[(3 alpha-hydroxytropo-6 beta-yl)-oxy]carbonyl}-4-{[((6-angeloyloxy)-3 alpha-yl)oxy]carbonyl}-3-phenylcy- clobutanecarboxylic acid (3), 1,2-bis{[(3 alpha-hydroxytropo-6 beta-yl)oxy]-carbonyl)-2-methyl-3-{[((6 beta-angeloyloxy)-3 alpha-yl)oxy]carbonyl}-4-phenylcyclobutanecarboxylate (4), and 1-{[(3 alpha-mesaconyloxytropo-6 beta-yl)-oxy]carbonyl}-2-{[(3 alpha-hydroxytropo-6 beta-yl)oxy]carbonyl}-2-methyl-3-{[((6 beta-angeloyloxy)-3 alpha-yl)oxy]carbonyl}-4-phenylcyclobutanecarboxylate (5).

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