title: Strychnobaillonine, an unsymmetrical bisindole alkaloid with an unprecedented skeleton from Strychnos icaja roots.
abstract: A reinvestigation of the roots of Strychnos icaja resulted in the isolation of a new bisindole alkaloid named strychnobaillonine (1) with original C-17-N-1' and C-23-C-17' junctions, in addition to sungucine, bisnordihydrotoxiferine, and strychnohexamine (2). Compound 1 showed potent activity against the chloroquine-sensitive 3D7 strain of Plasmodium falciparum in vitro with an IC50 value of 1.1 μM. The structures of the compounds were defined by detailed spectroscopic analyses, especially 1H and 13C NMR, DEPT, HSQC, COSY, NOESY, HMBC, and HRESIMS. The proposed absolute configuration was based on biosynthetic considerations and spectroscopic data (CD, NMR) supported by molecular modeling.
authors.affiliation: Center for Studies on Medicinal Plants and Traditional Medicine, Institute of Medical Research and Medicinal Plants Studies (IMPM) , P.O. Box 6163, Yaoundé, Cameroon.
authors.forename: Alembert T
authors.initials: AT
authors.lastname: Tchinda
authors.forename: Olivia
authors.initials: O
authors.lastname: Jansen
authors.forename: Jean-Noel
authors.initials: JN
authors.lastname: Nyemb
authors.forename: Monique
authors.initials: M
authors.lastname: Tits
authors.forename: Georges
authors.initials: G
authors.lastname: Dive
authors.forename: Luc
authors.initials: L
authors.lastname: Angenot
authors.forename: Michel
authors.initials: M
authors.lastname: Frédérich
mesh_terms: D000962:Antimalarials / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D002163:Cameroon; D002227:Carbazoles / Q000737:chemistry / Q000302:isolation & purification; D002738:Chloroquine / Q000494:pharmacology; D026121:Indole Alkaloids / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000737:chemistry; D010963:Plasmodium falciparum / Q000187:drug effects; D013331:Strychnine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D031451:Strychnos / Q000737:chemistry*; D014117:Toxiferine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D000962:Antimalarials; D002227:Carbazoles; D026121:Indole Alkaloids; C000589834:strychnobaillonine; C472945:strychnohexamine; C053959:bisnordihydrotoxiferine; C464946:sungucine; D002738:Chloroquine; D014117:Toxiferine; D013331:Strychnine