Isolation and antimalarial activity of alkaloids from Pseudoxandra cuspidata.
A novel and very unusual azaanthracene alkaloid, 1-aza-7,8,9,10-tetramethoxy-4-methyl-2-oxo-1,2-dihydroanthracene ( 1) and a new diastereoisomer of the bis-benzylisoquinoline alkaloid rodiasine, 1 S,1' R-rodiasine ( 2), as well as the alkaloids O-methylpunjabine ( 3) and O-methylmoschatoline ( 4) have been isolated from Pseudoxandra cuspidata bark, used in French Guiana as an antimalarial. Their structures were elucidated by spectroscopic analyses, especially 2D-NMR techniques (ADEQUATE and NOESY). We found that the antimalarial activity of this bark was mostly due to bis-benzylisoquinoline 1 S,1' R-rodiasine ( 2) (IC (50)= 1 microM) also displaying a low cytotoxicity.
Roumy
Vincent
V
Laboratoire Pharmacochimie des Substances Naturelles et Pharmacophores Redox, UMR 152 IRD, Université Toulouse 3 Paul Sabatier, Faculté des Sciences Pharmaceutiques, Toulouse, France.
Fabre
Nicolas
N
Souard
Florence
F
Massou
Stéphane
S
Bourdy
Geneviève
G
Maurel
Séverine
S
Valentin
Alexis
A
Moulis
Claude
C
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D029061:Annonaceae / Q000737:chemistry*; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006801:Humans; D019906:Nuclear Magnetic Resonance, Biomolecular; D024301:Plant Bark / Q000737:chemistry; D010963:Plasmodium falciparum / Q000187:drug effects; D018675:Toxicity Tests
D000470:Alkaloids; D000962:Antimalarials