Verrucofortine, a major metabolite of Penicillium verrucosum var. cyclopium, the fungus that produces the mycotoxin verrucosidin.
Verrucofortine [8], an alkaloid derived from tryptophan and leucine, has been isolated from the fungus Penicillium verrucosum var. cyclopium. The structure and absolute configuration have been established by a combination of spectroscopic and chemical techniques. Its structure is unrelated to that of other major metabolite of the organism, the highly toxic pyrone-type polyketide verrucosidin [1], which was previously reported to be a tremorgen. A second novel metabolite, normethylverrucosidin [3], has also been isolated and identified. Small quantities of several other secondary metabolites, ergosterol, cyclopenin [4], cyclopenol [5], and 3-O-methylviridicatin [6], were isolated. They are known fungal metabolites but had not previously been obtained from this fungus. Studies of verrucofortine toxicity in mice showed no apparent toxic effects at doses as high at 160 mg/kg ip.
Hodge
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RP
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235.
Harris
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CM
Harris
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TM
D000470:Alkaloids / Q000096:biosynthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D006576:Heterocyclic Compounds, 4 or More Rings; D006868:Hydrolysis; D007211:Indoles; D009682:Magnetic Resonance Spectroscopy; D009183:Mycotoxins / Q000096:biosynthesis*; D010407:Penicillium / Q000378:metabolism*; D010879:Piperazines; D011753:Pyrones / Q000096:biosynthesis
D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; D009183:Mycotoxins; D010879:Piperazines; D011753:Pyrones; C056012:verrucofortine; C048224:verrucosidin