Clerodane and labdane diterpenoids from Nuxia sphaerocephala.
Seven diterpenoids including four clerodane and three labdane derivatives, (13S)-ent-7beta-hydroxy-3-cleroden-15-oic acid (1), ent-7beta-hydroxy-2-oxo-3-cleroden-15-oic acid (2), ent-2,7-dioxo-3-clero-den-15-oic acid (3), ent-18-(E)-caffeoyloxy-7beta-hydroxy-3-cleroden-15-oic acid (4) (13S)-ent-18-(E)-coumaroyloxy-8(17)-labden-15-oic acid (5), ent-18-(E)-caffeoyloxy-8(17)-labden-15-oic acid (6), ent-15-(E)-caffeoyloxy-8(17)-labden-18-oic acid (7), have been isolated from an ethyl acetate extract of the leaves of Nuxia sphaerocephala, together with 17 known compounds. 3-Oxolup-20(29)-en-30-al (3-oxolupenal) (8) and 3beta-hydroxylup-20(29)-en-30-al (3beta-hydroxy-lupenal) (9) showed the best inhibitory activity against Plasmodium falciparum with the IC(50) values between 1.55 and 4.67 microg/ml in vitro, respectively. The structure and the relative stereochemistry of the compounds were established on the basis of their spectroscopic properties. The absolute configuration at C-13 of 1 and 5 was determined by the PGME amide procedure.
Mambu
Lengo
L
USM 0502-UMR5154 CNRS Chimie et Biochimie des substances naturelles, Département Régulations, Développement, Diversité Moléculaire, Muséum National d'Histoire Naturelle, 63 rue Buffon, 75231 Paris Cedex 05, France. mambu@mnhn.fr
Grellier
Philippe
P
Florent
Loic
L
Joyeau
Roger
R
Ramanitrahasimbola
David
D
Rasoanaivo
Philippe
P
Frappier
François
F
D000818:Animals; D000962:Antimalarials / Q000737:chemistry* / Q000494:pharmacology*; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D045785:Diterpenes, Clerodane / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D015394:Molecular Structure; D021261:Parasitic Sensitivity Tests; D010936:Plant Extracts / Q000737:chemistry* / Q000494:pharmacology; D010963:Plasmodium falciparum / Q000187:drug effects
D000962:Antimalarials; D004224:Diterpenes; D045785:Diterpenes, Clerodane; D010936:Plant Extracts