Verrucine F, a quinazoline from Penicillium verrucosum.
Verrucine F (3), a quinazoline similar to verrucines A (1) and B (2), contains one anthranilic acid residue, one L-glutamine residue, and one alpha,beta-unsaturated phenylalanine residue, as determined by NMR, MS, and chemical methods. Compounds 1 and 3, but not 2, were produced by Penicillium verrucosum J255 and eight additional P. verrucosum strains. Verrucines were typically more concentrated in the inner (older) parts of the colony, and 3 peaked 4-8 days after 1, but at 10-fold lower concentrations (approximately 200 microg/g). Verrucine F (3) formed spontaneously from 1 in buffered water solutions, probably by oxidation at C-1 followed by water elimination.
Leong
Su-Lin
SL
Department of Microbiology, Swedish University of Agricultural Sciences, P.O. Box 7025, SE-750 07 Uppsala, Sweden.
Schnürer
Johan
J
Broberg
Anders
A
D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010407:Penicillium / Q000737:chemistry*; D011799:Quinazolines / Q000737:chemistry / Q000302:isolation & purification*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013056:Spectrophotometry, Ultraviolet
D011799:Quinazolines; C533329:verrucine F