Coumarins from Galipea panamensis and Their Activity against Leishmania panamensis.
Two new coumarin compounds (1 and 2), phebalosin (3), its derived artifact murralongin (4), and murrangatin acetonide (5) were isolated from the leaves of Galipea panamensis. The structures of 1 and 2 were assigned as 7-{[(2R*)-3,3-dimethyloxiran-2-yl]methoxy}-8-[(2R*,3R*)-3-isopropenyloxiran-2-yl]-2H-chromen-2-one and 7-methoxy-8-(4-methyl-3-furyl)-2H-chromen-2-one, respectively, on the basis of their spectroscopic data (primarily NMR and MS). Compounds 1-3 were tested against axenic amastigote forms of Leishmania panamensis and displayed 50% effective concentrations (EC(50)) of 9.9, 10.5, and 14.1 microg/mL, respectively. These three compounds also displayed cytotoxicity (IC(50)) at concentrations of 9.7, 33.0, and 20.7 microg/mL, respectively, on human promonocytic U-937 cells.
Arango
Victor
V
Instituto de Quimica, Quimica de Plantas Colombianas, Universidad de Antioquia, A.A 1226, Medellin, Colombia.
Robledo
Sara
S
Séon-Méniel
Blandine
B
Figadère
Bruno
B
Cardona
Wilson
W
Sáez
Jairo
J
Otálvaro
Felipe
F
D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D003105:Colombia; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D006801:Humans; D007891:Leishmania / Q000187:drug effects*; D015394:Molecular Structure; D055017:Monocyte-Macrophage Precursor Cells / Q000187:drug effects; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D027821:Rutaceae / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C550063:7-(((2R*)-3,3-dimethyloxiran-2-yl)methoxy)-8-((2R*,3R*)-3-isopropenyloxiran-2-yl)-2H-chromen-2-one; C550062:7-methoxy-8-(4-methyl-3-furyl)-2H-chromen-2-one; D000981:Antiprotozoal Agents; D003374:Coumarins; C048686:phebalosin