Title
Isomeric tropane alkaloids from the aerial parts of **Schizanthus tricolor**
Author
Faculty/Department
Faculty of Pharmaceutical, Biomedical and Veterinary Sciences. Pharmacy
Publication type
article
Publication
Columbus, Ohio ,
Subject
Pharmacology. Therapy
Source (journal)
Journal of natural products. - Columbus, Ohio, 1979, currens
Volume/pages
73(2010) :5 , p. 844-847
ISSN
0163-3864
ISI
000278080900010
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
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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