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Bioactive diterpenes from the fruits of Detarium microcarpum.
J Nat Prod. 2006 May; 69(5):768-73.JN

Abstract

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.

Authors+Show Affiliations

Cavin AL
Laboratory of Pharmacognosy and Phytochemistry, School of Pharmaceutical Sciences, University of Geneva, CH-1211 Geneva 4, Switzerland.
Hay AE
No affiliation info available
Marston A
No affiliation info available
Stoeckli-Evans H
No affiliation info available
Scopelliti R
No affiliation info available
Diallo D
No affiliation info available
Hostettmann K
No affiliation info available

MeSH

Antifungal AgentsCholinesterase InhibitorsCladosporiumCrystallography, X-RayDiterpenes, ClerodaneFabaceaeFruitMaliMolecular ConformationMolecular StructurePlants, Medicinal

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16724838

Citation

Cavin, Anne-Laure, et al. "Bioactive Diterpenes From the Fruits of Detarium Microcarpum." Journal of Natural Products, vol. 69, no. 5, 2006, pp. 768-73.
Cavin AL, Hay AE, Marston A, et al. Bioactive diterpenes from the fruits of Detarium microcarpum. J Nat Prod. 2006;69(5):768-73.
Cavin, A. L., Hay, A. E., Marston, A., Stoeckli-Evans, H., Scopelliti, R., Diallo, D., & Hostettmann, K. (2006). Bioactive diterpenes from the fruits of Detarium microcarpum. Journal of Natural Products, 69(5), 768-73.
Cavin AL, et al. Bioactive Diterpenes From the Fruits of Detarium Microcarpum. J Nat Prod. 2006;69(5):768-73. PubMed PMID: 16724838.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Bioactive diterpenes from the fruits of Detarium microcarpum. AU - Cavin,Anne-Laure, AU - Hay,Anne-Emmanuelle, AU - Marston,Andrew, AU - Stoeckli-Evans,Helen, AU - Scopelliti,Rosario, AU - Diallo,Drissa, AU - Hostettmann,Kurt, PY - 2006/5/27/pubmed PY - 2006/7/14/medline PY - 2006/5/27/entrez SP - 768 EP - 73 JF - Journal of natural products JO - J Nat Prod VL - 69 IS - 5 N2 - 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. SN - 0163-3864 UR - https://www.unboundmedicine.com/medline/citation/16724838/Bioactive_diterpenes_from_the_fruits_of_Detarium_microcarpum_ DB - PRIME DP - Unbound Medicine ER -