Bioactive diterpenes from the fruits of Detarium microcarpum.
A fruit pulp extract of Detarium microcarpum showed inhibition of the growth of the plant pathogenic fungus Cladosporium cucumerinum and of the enzyme acetylcholinesterase, implicated in Alzheimer's disease. Fractionation of this extract led to the isolation of four new clerodane diterpenes, 3,4-epoxyclerodan-13E-en-15-oic acid (1), 5alpha,8alpha(2-oxokolavenic acid) (2), 3,4-dihydroxyclerodan-13E-en-15-oic acid (4), and 3,4-dihydroxyclerodan-13Z-en-15-oic acid (5). Also isolated were 2-oxokolavenic acid (3) and copalic acid (6). Structure elucidation of the compounds was carried out by spectroscopic data interpretation and by the X-ray crystallography of 2 and 4. Three of the new clerodane diterpenes (1, 2, and 5) showed both antifungal activity and inhibition of acetylcholinesterase, and 3 showed a slight inhibition of this enzyme.
Cavin
Anne-Laure
AL
Laboratory of Pharmacognosy and Phytochemistry, School of Pharmaceutical Sciences, University of Geneva, CH-1211 Geneva 4, Switzerland.
Hay
Anne-Emmanuelle
AE
Marston
Andrew
A
Stoeckli-Evans
Helen
H
Scopelliti
Rosario
R
Diallo
Drissa
D
Hostettmann
Kurt
K
D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002800:Cholinesterase Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002963:Cladosporium / Q000187:drug effects; D018360:Crystallography, X-Ray; D045785:Diterpenes, Clerodane / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007887:Fabaceae / Q000737:chemistry*; D005638:Fruit / Q000737:chemistry; D008302:Mali; D008968:Molecular Conformation; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*
D000935:Antifungal Agents; D002800:Cholinesterase Inhibitors; D045785:Diterpenes, Clerodane