Cercophorins A-C: novel antifungal and cytotoxic metabolites from the coprophilous fungus Cercophora areolata.
Cercophorins A-C (3-5), three novel isocoumarin derivatives with antifungal and cytotoxic activities, have been isolated from the coprophilous fungus Cercophora areolata (JS 166 = UAMH 7495), a colonist of porcupine dung. Two additional new isocoumarins, decarboxy-citrinone (1) and 4-acetyl-8-hydroxy-6-methoxy-5-methylisocoumarin (2), and a known tricothecene mycotoxin, roridin E (6), were also obtained from this species. Compounds 1-6 were isolated from ethyl acetate extracts of mycelia and liquid cultures of C. areolata through bioassay-guided fractionation and are the first metabolites to be reported from a member of the genus Cercophora. Their structures were assigned on the basis of MS, selective INEPT, and 2D-NMR experiments.
Whyte
A C
AC
Department of Chemistry, University of Iowa, Iowa City 52242, USA.
Gloer
J B
JB
Scott
J A
JA
Malloch
D
D
D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification*; D001203:Ascomycota / Q000737:chemistry* / Q000187:drug effects / Q000378:metabolism; D001412:Bacillus subtilis / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000935:Antifungal Agents; D003374:Coumarins; C102974:cercophorin A; C102975:cercophorin B; C102976:cercophorin C