title: Antifungal azaphilones from the fungus Chaetomium cupreum CC3003.
abstract: 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.
authors.affiliation: Department of Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand. somdej@kku.ac.th
authors.forename: Somdej
authors.initials: S
authors.lastname: Kanokmedhakul
authors.forename: Kwanjai
authors.initials: K
authors.lastname: Kanokmedhakul
authors.forename: Pitak
authors.initials: P
authors.lastname: Nasomjai
authors.forename: Sysavad
authors.initials: S
authors.lastname: Louangsysouphanh
authors.forename: Kasem
authors.initials: K
authors.lastname: Soytong
authors.forename: Minoru
authors.initials: M
authors.lastname: Isobe
authors.forename: Palangpon
authors.initials: P
authors.lastname: Kongsaeree
authors.forename: Samran
authors.initials: S
authors.lastname: Prabpai
authors.forename: Apichart
authors.initials: A
authors.lastname: Suksamrarn
mesh_terms: 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
chemical_list: D000935:Antifungal Agents; D001578:Benzopyrans; D010860:Pigments, Biological; C494154:azaphilone