Article,

Grahamines a-E, Cyclobutane-Centered Tropane Alkaloids from the Aerial Parts of Schizanthus Grahamii

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Journal of Natural Products, 74 (11): 2388-2394 (2011)
DOI: 10.1021/np200450y

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)oxycarbonyl-2-methyl-3-((6 beta-angeloyloxy)-3 alpha-yl)oxycarbonyl-4- phenylcyclobutanecarboxylic acid (1), 2-(3 alpha-hydroxytropo-6 beta-yl)oxy-carbonyl-2-methy1-3-((6 beta-tigloyloxy)-3 alpha-yl)oxycarbonyl-4-phenylcyclobutanecarboxylic acid (2), 1-methyl-2-(3 alpha-hydroxytropo-6 beta-yl)-oxycarbonyl-4-((6-angeloyloxy)-3 alpha-yl)oxycarbonyl-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)oxycarbonyl-4-phenylcyclobutanecarboxylate (4), and 1-(3 alpha-mesaconyloxytropo-6 beta-yl)-oxycarbonyl-2-(3 alpha-hydroxytropo-6 beta-yl)oxycarbonyl-2-methyl-3-((6 beta-angeloyloxy)-3 alpha-yl)oxycarbonyl-4-phenylcyclobutanecarboxylate (5)., type = Journal Article, keywords = 2+2 photodimerization, genus erythroxylum, cell-walls, acid, catalysis, esters, bamboo

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