Purification, identification and activity of phomodione, a furandione from an endophytic Phoma species.
Phomodione, [(4aS(*),9bR(*))-2,6-diacetyl-7-hydroxy-4a,9-dimethoxy-8,9b-dimethyl-4a.9b-dihydrodibenzo[b,d]furan-1,3(2H,4H)-dione], an usnic acid derivative, was isolated from culture broth of a Phoma species, discovered as an endophyte on a Guinea plant (Saurauia scaberrinae). It was identified using NMR, X-ray crystallography, high resolution mass spectrometry, as well as infrared and Raman spectroscopy. In addition to phomodione, usnic acid and cercosporamide, known compounds with antibiotic activity, were also found in the culture medium. Phomodione exhibited a minimum inhibitory concentration of 1.6 microg/mL against Staphylococcus aureus using the disk diffusion assay, and was active against a representative oomycete, ascomycete and basidiomycete at between three and eight micro-grams per mL.
Hoffman
Angela M
AM
Department of Chemistry, University of Portland, Portland, OR 97203, USA. hoffman@up.edu
Mayer
Steven G
SG
Strobel
Gary A
GA
Hess
Wilford M
WM
Sovocool
G Wayne
GW
Grange
Andrew H
AH
Harper
James K
JK
Arif
Atta M
AM
Grant
David M
DM
Kelley-Swift
Elizabeth G
EG
D029041:Actinidiaceae / Q000382:microbiology*; D001203:Ascomycota / Q000737:chemistry* / Q000648:ultrastructure; D001487:Basidiomycota / Q000187:drug effects; D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D008855:Microscopy, Electron, Scanning; D015394:Molecular Structure; D009868:Oomycetes / Q000187:drug effects; D013210:Staphylococcus / Q000187:drug effects
D001572:Benzofurans; C530256:phomodione; C073339:usnic acid; C085452:cercosporamide