Structure determination and biosynthesis of a novel metabolite of Fusarium culmorum, apotrichodiol.
A novel dead-end metabolite of Fusarium culmorum was isolated and characterized (Zamir, L. O., and Devor, K. A. (1987) J. Biol. Chem. 15348-15353). This 3 alpha, 13-dihydroxy-apotrichothec-9-ene is herein given the trivial name of apotrichodiol to indicate its basic structure. The characterization of apotrichodiol was established through the application of spectroscopic techniques (ultraviolet, 1H-NMR, 13C-NMR, COSY, and DEPT experiments) on the natural product as well as on its diacetate derivative. The mode of folding of its precursor farnesyl pyrophosphate was derived from feeding experiments with 3,4-[13C2]mevalonolactone. 13C-NMR assignments were also made of 3-acetyldeoxynivalenol and sambucinol which were derived from these feedings with enriched mevalonolactone.
Zamir
L O
LO
Université du Québec, Institut Armand-Frappier, Laval, Canada.
Devor
K A
KA
Nadeau
Y
Y
Sauriol
F
F
D002851:Chromatography, High Pressure Liquid; D005670:Fusarium / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008798:Mevalonic Acid / Q000031:analogs & derivatives / Q000378:metabolism; D012717:Sesquiterpenes / Q000096:biosynthesis*; D014255:Trichothecenes / Q000096:biosynthesis*
D012717:Sesquiterpenes; D014255:Trichothecenes; C054185:apotrichodiol; C043247:3-acetyldeoxynivalenol; C015367:mevalonolactone; C054183:sambucinol; D008798:Mevalonic Acid