Antifungal azaphilones from the fungus Chaetomium cupreum CC3003.
Three new azaphilones named rotiorinols A-C (1-3), two new stereoisomers, (-)-rotiorin (4) and epi-isochromophilone II (5), and a known compound, rubrorotiorin (6), were isolated from the fungus Chaetomium cupreum CC3003. Structures were established on the basis of spectroscopic evidence. The absolute configuration of 1 was determined by the modified Mosher's method along with an X-ray analysis of its acetate derivative, as well as by chemical transformation. Compounds 1, 3, 4, and 6 exhibited antifungal activity against Candida albicans with IC50 values of 10.5, 16.7, 24.3, and 0.6 microg/mL, respectively.
Kanokmedhakul
Somdej
S
Department of Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand. somdej@kku.ac.th
Kanokmedhakul
Kwanjai
K
Nasomjai
Pitak
P
Louangsysouphanh
Sysavad
S
Soytong
Kasem
K
Isobe
Minoru
M
Kongsaeree
Palangpon
P
Prabpai
Samran
S
Suksamrarn
Apichart
A
D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001578:Benzopyrans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D002597:Chaetomium / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010860:Pigments, Biological / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism; D013785:Thailand
D000935:Antifungal Agents; D001578:Benzopyrans; D010860:Pigments, Biological; C494154:azaphilone