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

Published inJournal of natural products, vol. 74, no. 11, p. 2388-2394
Publication date2011
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).

Citation (ISO format)
CRETTON, Sylvian et al. Grahamines A–E, Cyclobutane-Centered Tropane Alkaloids from the Aerial Parts of Schizanthus grahamii. In: Journal of natural products, 2011, vol. 74, n° 11, p. 2388–2394. doi: 10.1021/np200450y
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ISSN of the journal0163-3864
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