Ceramicines U-Z from Chisocheton ceramicus and structure-antimalarial activity relationship study
Document Type
Article
Publication Date
1-1-2024
Abstract
Ceramicines are a series of limonoids which were isolated from the barks of Malaysian Chisocheton ceramicus (Meliaceae), and were known to show various biological activity. Six new limonoids, ceramicines U-Z (1-6), with a cyclopentanonea] phenanthrene ring system with a beta-furyl ring at C-17 were isolated from the barks of C. ceramicus. Their structures were determined on the basis of the 1D and 2D NMR analyses, and their absolute configurations were investigated by CD spectroscopy. Ceramicine W (3) exhibited potent antimalarial activity against Plasmodium falciparum 3D7 strain with IC50 value of 1.2 mu M. In addition, the structure-antimalarial activity relationship (SAR) of the ceramicines was investigated to identify substituent patterns that may enhance activity. It appears that ring B and the functional groups in the vicinity of rings B and C are critical for the antimalarial activity of the ceramicines. In particular, bulky ester substituents with equatorial orientation at C-7 and C-12 greatly increase the antimalarial activity.
Keywords
Ceramicines U-Z, Limonoids, Chisocheton ceramicus, Meliaceae, Antimalarial activity, Structureantimalarial activity relationship
Divisions
CHEMISTRY
Funders
Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT) Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research (KAKENHI)
Publication Title
Journal of Natural Medicines
Volume
78
Issue
1
Publisher
Springer Verlag (Germany)
Publisher Location
SHIROYAMA TRUST TOWER 5F, 4-3-1 TORANOMON, MINATO-KU, TOKYO, 105-6005, JAPAN