Verrucofortine, a major metabolite of Penicillium verrucosum var. cyclopium, the fungus that produces the mycotoxin verrucosidin

Richard P. Hodge, Constance M. Harris, Thomas M. Harris

Research output: Contribution to journalArticle

53 Citations (Scopus)

Abstract

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 the 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.

Original languageEnglish (US)
Pages (from-to)66-73
Number of pages8
JournalJournal of Natural Products
Volume51
Issue number1
StatePublished - 1988
Externally publishedYes

Fingerprint

Penicillium verrucosum
Mycotoxins
Poisons
Penicillium
Metabolites
Fungi
tryptophan-leucine
mycotoxins
Pyrones
metabolites
Polyketides
Ergosterol
fungi
Alkaloids
pyrones
polyketides
ergosterol
toxicity testing
tryptophan
secondary metabolites

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Verrucofortine, a major metabolite of Penicillium verrucosum var. cyclopium, the fungus that produces the mycotoxin verrucosidin. / Hodge, Richard P.; Harris, Constance M.; Harris, Thomas M.

In: Journal of Natural Products, Vol. 51, No. 1, 1988, p. 66-73.

Research output: Contribution to journalArticle

Hodge, Richard P. ; Harris, Constance M. ; Harris, Thomas M. / Verrucofortine, a major metabolite of Penicillium verrucosum var. cyclopium, the fungus that produces the mycotoxin verrucosidin. In: Journal of Natural Products. 1988 ; Vol. 51, No. 1. pp. 66-73.
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