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Title
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Isomeric tropane alkaloids from the aerial parts of **Schizanthus tricolor**
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Author
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Abstract
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| Investigation of the aerial parts of Schizanthus tricolor yielded seven isomeric tropane alkaloids: 3α-(1-methylitaconyl)-6β-senecioyloxytropane (1), 3α-(1-methylitaconyl)-6β-angeloyloxytropane (2), 3α-(1-methylmesaconyl)-6β-senecioyloxytropane (3), 3α-(1-methylmesaconyl)-6β-angeloyloxytropane (4), 3α-(1-methylmesaconyl)-6β-tigloyloxytropane (5), 3α-(1-methylcitraconyl)-6β-senecioyloxytropane (6), and 3α-(1-methylcitraconyl)-6β-angeloyloxytropane (7). Their structures were established by NMR including 1H, 13C NMR, HSQC, HMBC, COSY, and NOESY experiments, UV, IR, and mass spectrometry. Compounds 1, 6, and 7 are new to the literature. Alkaloids 1, 3, 4, and 5 and a mixture of 3, 4, and 5 were evaluated for in vitro antiplasmodial and cytotoxic activity. Compounds 1, 4, and 5 showed marginal inhibition of Plasmodium falciparum strain K1 with IC50 values of 22.8, 24.8, and 36.0 μM and displayed no cytotoxicity on MRC-65 cells (CC50 > 64 μM). Alkaloid 3 was inactive (IC50 63.5 μM). The alkaloid mixture exhibited slightly higher activity (IC50 17.0 μM) than the pure compounds, indicating some synergy between the different isomers. |
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Language
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English
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Source (journal)
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Journal of natural products. - Columbus, Ohio, 1979, currens
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Publication
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Columbus, Ohio
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2010
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ISSN
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0163-3864
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DOI
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10.1021/NP900780W
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Volume/pages
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73
:5
(2010)
, p. 844-847
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ISI
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000278080900010
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Full text (Publisher's DOI)
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