In the course of our search for antimalarial leads from marine algae, four metabolites, sargaquinoic acid, sargahydroquinoic acid, sargaquinal and fucoxanthin, were isolated from the South African alga Sargassum heterophyllum. Fucoxanthin and sargaquinal showed good antiplasmodial activity toward a chloroquine-sensitive strain (D10) of Plasmodium falciparum (IC 50 1.5 and 2.0 μm, respectively), while sargaquinoic acid and sargahydroquinoic acid were only moderately active (IC 50 12.0 and 15.2 μm, respectively).
Aim of the study
The objective of this study was to isolate and characterize the active constituents of the traditionally used antimalarial plant Liriodendron tulipifera by antiplasmodial-assay guided fractionation.
Materials and methods
Bark and leaves were extracted with solvents of increasing polarity. Fractions were generated using flash chromatography, counter current chromatography and preparative HPLC and subjected to in vitro antiplasmodial and cytotoxicity assays. Active fractions were subjected to further fractionation until pure compounds were isolated, for which the IC50 values were calculated.
Results and discussion
Six known aporphine alkaloids, asimilobine (1), norushinsunine (2), norglaucine (3), liriodenine (4), anonaine (5) and oxoglaucine (6) were found to be responsible for the antiplasmodial activity of the bark. Leaves yielded two known sesquiterpene lactones, peroxyferolide (7) and lipiferolide (8) with antiplasmodial activity. The antiplasmodial activity of (2) (IC50 = 29.6 μg/ml), (3) (IC50 = 22.0 μg/ml), (6) (IC50= 9.1 μg/mL), (7) (IC50 = 6.2 μg/ml) and (8) (IC50 = 1.8 μg/ml) are reported for the first time.
Conclusion
This work supports the historical use of Liriodendron tulipifera as an antimalarial remedy of the United States and characterizes its antiplasmodial constituents.
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