Griseofulvin from Penicillium griseofulvum

Griseofulvin [XLIX], first isolated from Penicillium griseofulvum Dierckx, is effective orally in the treatment of ringworm in animals and man. The observations of Gentles , and Cochrane and Tullett , in antifungal experiments, that this antibiotic seems to possess anti-inflammatory properties led... 

The polycyclic antibiotic, griseofulvin, is derived from Penicillium griseofulvum and is perhaps the most important agent in the systemic treatment of dermatophyte infections (Fig. 2). It is used orally for the treatment of superficial fungal infections of nails, hair, and skin, increasing the resistance of keratin to infection. Side effects of therapy are usually mild most common are nausea, diarrhoea and headaches (Swartz 1962). 

McMillan, J. Griseofulvin. Part IX. Isolation of the bromo-analogue from Penicillium griseofulvum and Penicillium nigricans. J. Chem. Soc. 1954, 2585. 

Research on novel fungal secondary metabolites resulted in the isolation of an interesting spiran, griseofulvin (15), from fermentation beers of the mold Penicillium griseofulvum. 

In 1939, the isolation of griseofulvin from mycelia of Penicillium griseofulvum was reported [1], This compound has the empirical formula C17H17CIO6 and Grove et al. [2] determined its structure 1 in 1952. Fermentation conditions for griseofulvin production have appeared infrequently in the scientific literature, because this substance is of great economic importance. It is one of the few antifungal compounds that are... 

XXXVI. The latter could be synthesized from 7 molecules of acetate, with malonyl coenzyme A as an intermediate as it is in the synthesis of fatty acids. 0-Methylation and the introduction of a chlorine atom into the carbon skeleton would be required to yield XXXV. But the biosynthesis of the skeleton itself appears to be independent of the process of chlorination, for dechlorogriseofulvin has been isolated from culture fluids of Penicillium griseofulvum and Penicillium janczewskii, and the bromo analogue of griseofulvin may be formed when chloride in the culture medium is replaced by bromide . ... 

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