Antimalarial Benzylisoquinoline Alkaloid from the Rainforest Tree Doryphora sassafras
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Accepted Manuscript (AM)
Author(s)
Buchanan, Malcolm S
Davis, Rohan A
Duffy, Sandra
Avery, Vicky M
Quinn, Ronald J
Year published
2009
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Mass-directed isolation of the CH2Cl2/MeOH extract of Doryphora sassafras resulted in the purification of a new benzylisoquinoline alkaloid, 1-(4-hydroxybenzyl)-6,7-methylenedioxy-2-methylisoquinolinium trifluoroacetate (1), and the known aporphine alkaloid (S)-isocorydine (2). The structures of 1 and 2 were determined by 1D and 2D NMR and MS data analyses. The compounds were isolated during a drug discovery program aimed at identifying new antimalarial leads from a prefractionated natural product library. When tested against two different strains of the parasite Plasmodium falciparum (3D7 and Dd2), 1 displayed IC50 values ...
View more >Mass-directed isolation of the CH2Cl2/MeOH extract of Doryphora sassafras resulted in the purification of a new benzylisoquinoline alkaloid, 1-(4-hydroxybenzyl)-6,7-methylenedioxy-2-methylisoquinolinium trifluoroacetate (1), and the known aporphine alkaloid (S)-isocorydine (2). The structures of 1 and 2 were determined by 1D and 2D NMR and MS data analyses. The compounds were isolated during a drug discovery program aimed at identifying new antimalarial leads from a prefractionated natural product library. When tested against two different strains of the parasite Plasmodium falciparum (3D7 and Dd2), 1 displayed IC50 values of 3.0 and 4.4 μM, respectively. Compound 1 was tested for cytotoxicity toward a human embryonic kidney cell line (HEK293) and displayed no activity at 120 μM.
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View more >Mass-directed isolation of the CH2Cl2/MeOH extract of Doryphora sassafras resulted in the purification of a new benzylisoquinoline alkaloid, 1-(4-hydroxybenzyl)-6,7-methylenedioxy-2-methylisoquinolinium trifluoroacetate (1), and the known aporphine alkaloid (S)-isocorydine (2). The structures of 1 and 2 were determined by 1D and 2D NMR and MS data analyses. The compounds were isolated during a drug discovery program aimed at identifying new antimalarial leads from a prefractionated natural product library. When tested against two different strains of the parasite Plasmodium falciparum (3D7 and Dd2), 1 displayed IC50 values of 3.0 and 4.4 μM, respectively. Compound 1 was tested for cytotoxicity toward a human embryonic kidney cell line (HEK293) and displayed no activity at 120 μM.
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Journal Title
Journal of Natural Products
Volume
72
Issue
8
Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Natural Products, copyright 2009 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/np9002564
Subject
Chemical sciences
Biological sciences
Biochemistry and cell biology not elsewhere classified
Biomedical and clinical sciences
Traditional, complementary and integrative medicine