Antimalarial benzylisoquinoline alkaloid from the rainforest tree Doryphora sassafras.
Mass-directed isolation of the CH(2)Cl(2)/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 IC(50) values of 3.0 and 4.4 microM, respectively. Compound 1 was tested for cytotoxicity toward a human embryonic kidney cell line (HEK293) and displayed no activity at 120 microM.
Buchanan
Malcolm S
MS
Eskitis Institute, Griffith University, Nathan, Queensland 4111, Australia.
Davis
Rohan A
RA
Duffy
Sandra
S
Avery
Vicky M
VM
Quinn
Ronald J
RJ
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001315:Australia; D044182:Benzylisoquinolines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D017753:Ecosystem; D006801:Humans; D015394:Molecular Structure; D021261:Parasitic Sensitivity Tests; D010963:Plasmodium falciparum / Q000187:drug effects*
D000470:Alkaloids; D000962:Antimalarials; D044182:Benzylisoquinolines