The biosynthesis of 4-hydroxycoumarin and dicoumarol by Aspergillus fumigatus Fresenius.
A strain of Aspergillus fumigatus Fresenius, isolated from spoiled hay, converts melilotic acid (o-hydroxyphenylpropionic acid) and o-coumaric acid into 4-hydroxycoumarin and dicoumarol. The sequence is shown to be melilotic acid (I) [Formula: see text] coumaric acid (IV) [Formula: see text] beta-hydroxymelilotic acid (II) [Formula: see text] beta-oxomelilotic acid (III) [Formula: see text] 4-hydroxycoumarin (VI), on the basis of (1) studies on the formation of postulated intermediates, (2) experiments with isotopically labelled materials and (3) sequential enzyme induction. In the presence of semicarbazide, o-coumaraldehyde is formed from o-coumaric acid: there is no evidence, however, that this lies on the normal metabolic pathway.
D001230:Aspergillus / Q000378:metabolism*; D001578:Benzopyrans / Q000096:biosynthesis*; D002247:Carbon Isotopes; D001728:Dicumarol / Q000096:biosynthesis*; D004790:Enzyme Induction; D007259:Infrared Rays; D007783:Lactones / Q000096:biosynthesis*; D013057:Spectrum Analysis; D014316:Tritium; D014466:Ultraviolet Rays
D001578:Benzopyrans; D002247:Carbon Isotopes; D007783:Lactones; D014316:Tritium; D001728:Dicumarol