Structures of cordypyridones A-D, antimalarial N-hydroxy- and N-methoxy-2-pyridones from the insect pathogenic fungus Cordyceps nipponica.
Bioassay-guided fractionation of the extracts from the insect pathogenic fungus Cordyceps nipponica BCC 1389 led to the isolation of N-hydroxy- and N-methoxy-2-pyridones, cordypyridones A-D (1-4). Structures of these compounds, including absolute configuration, were determined by spectroscopic methods, chemical conversions and single-crystal X-ray diffraction analyses. Codypyridones A and B, atropisomers of each other, exhibited potent in vitro antimalarial activity with IC(50) values of 0.066 and 0.037 microg/mL, respectively, while their cytotoxicity was much weaker.
Isaka
M
M
National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Bangkok 10400, Thailand. isaka@biotec.or.th
Tanticharoen
M
M
Kongsaeree
P
P
Thebtaranonth
Y
Y
D000818:Animals; D000962:Antimalarials / Q000737:chemistry* / Q000302:isolation & purification; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D005260:Female; D005658:Fungi / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010963:Plasmodium falciparum / Q000187:drug effects; D011728:Pyridones / Q000737:chemistry / Q000302:isolation & purification; D013057:Spectrum Analysis; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
D000962:Antimalarials; D011728:Pyridones; C437383:cordypyridone A; C437384:cordypyridone B; C437385:cordypyridone C; C437386:cordypyridone D