Indole alkaloids from Muntafara sessilifolia with antiplasmodial and cytotoxic activities.
Four vobasinyl-iboga bisindole and one 2-acyl monomeric indole alkaloids were isolated from the stem bark of Muntafara sessilifolia along with eleven known compounds. Their structures and relative stereochemistry were elucidated on the basis of spectroscopic data including 1D and 2D NMR and mass spectrometry (MS). All isolated compounds were evaluated in vitro for antiplasmodial activity against the chloroquine-resistant strain FcB1 of Plasmodium falciparum, and for cytotoxicity against the human lung cell line MRC-5 and the rat skeletal muscle cell line L-6. 3'-Oxo-tabernaelegantine A exhibited antiplasmodial activity (4.4 μM IC(50)) associated with non-significant cytotoxicity (selectivity index of 48). Tabernaelegantine B and D displayed the highest cytotoxicity with IC(50) values of 0.47 and 1.89 μM on MRC-5 cells, and 0.42 and 2.7 μM on L-6 cells, respectively.
UMR 7245 CNRS-MNHN Molécules de Communication et Adaptation des Micro-organismes, Département Régulations, Développement et Diversité Moléculaire, Muséum National d'Histoire Naturelle, 57 rue Cuvier CP 54, 75231 Paris Cedex 05, France.
Marion
M
Girardot
Christiane
C
Deregnaucourt
Alexandre
A
Deville
Lionel
L
Dubost
Roger
R
Joyeau
Lucile
L
Allorge
Philippe
P
Rasoanaivo
Lengo
L
Mambu
D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D029062:Apocynaceae / Q000737:chemistry*; D002738:Chloroquine; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010963:Plasmodium falciparum / Q000187:drug effects*; D051381:Rats; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
C570161:3'-oxo-tabernaelegantine A; D000962:Antimalarials; D000972:Antineoplastic Agents, Phytogenic; D026121:Indole Alkaloids; D013729:Terpenes; C570162:tabernaelegantine B; C570163:tabernaelegantine D; D002738:Chloroquine