Isomeric tropane alkaloids from the aerial parts of Schizanthus tricolor

Cretton, Sylvian; Glauser, Gaétan; Humam, Munir; Jeannerat, Damien; Muñoz, Orlando; Maes, Louis; Christen, Philippe; Hostettmann, Kurt

doi:10.1021/np900780w

Scientific article

English

Isomeric tropane alkaloids from the aerial parts of Schizanthus tricolor

Contributors

Cretton, Sylvian; Glauser, Gaétan; Humam, Munir; Jeannerat, Damien; Muñoz, Orlando; Maes, Louis; Christen, Philippe; Hostettmann, Kurt

Published in

Journal of natural products, vol. 73, no. 5, p. 844-847

Publication date

2010

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.

UNIGE affiliation entities

Citation (ISO format)

CRETTON, Sylvian et al. Isomeric tropane alkaloids from the aerial parts of Schizanthus tricolor. In: Journal of natural products, 2010, vol. 73, n° 5, p. 844–847. doi: 10.1021/np900780w

Article (Published version)

Identifiers

PID : unige:6731
DOI : 10.1021/np900780w

Journal ISSN

0163-3864

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Isomeric tropane alkaloids from the aerial parts of Schizanthus tricolor

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Published in

Publication date

Abstract

UNIGE affiliation entities

Citation (ISO format)

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Creation

First validation

Update

Status update

Last indexation