Penicillium urticae

A simple lactone, parasorbic acid, from the fruit of mountain ash, inhibits seed germination and also has antibacterial action (75). Another such compound, patulin, is produced by several fungi, including Penicillium urticae, which produced large amounts of the substance when growing on wheat straw (76). 

Collie s hypothesis that aromatic compounds are made biologically from ethanoic acid was greatly expanded by A. J. Birch to include an extraordinary number of diverse compounds. The generic name acetogenin has been suggested as a convenient classification for ethanoate (acetate)-derived natural products, but the name polyketides also is used. Naturally occurring aromatic compounds and quinones are largely made in this way. An example is 2-hydroxy-6-methylbenzoic acid formed as a metabolite of the mold Penicillium urticae ... 

Despite the apparent connections between formation of antibiotics and spores, it has become clear that antibiotic production is not obligatory for spore formation [192]. The most damaging evidence to the antibiotic-spore obligatory hypothesis is the existence of mutants which form no antibiotic but still sporulate. Such mutants have been found in the cases of bacitracin (Bacillus licheniformis), myco-bacillin (Bacillus subtilis), linear gramicidin (B. brevis), tyrocidine (B. brevis), gramicidin S (B. brevis), oxytetracycline (Streptomyces rimosus), streptomycin (S. griseus), methylenomycin A (Streptomyces coelicolor), and patulin (Penicillium urticae). 

Sekiguchi, J., Kuroda, H., Yamada, Y., and Okada, H. (1985). Structure of patulolide A, a new macrolide from Penicillium urticae mutants. Tetrahedron Lett. 26, 2341 -2342. 

The biosynthetic study of griseofulvin by Penicillium urticae and microbial transformation of (-)- and (+)-dehydrogriseofulvin (4) and their derivatives by Streptomyces cinereocrocatus followed by NMR... 

SEKIGUCHI, J., GAUCHER, G.M., Conidiogenesis and secondary metabolism in Penicillium urticae, Appl. Environ. Microbiol., 1977,33, 147-158. 

Biosynthesis In Penicillium urticae from 6-methyl-salicylic acid - m-cresol - m-hydroxybenzyl alcohol -> gentisic acid. In plants possibly by hydroxyla-tion of benzoic acid. 

The antibiotic ff-(+)-patulolide (17), first isolated in 1985 from the culture broth of Penicillium urticae mutant S11R59, was obtained from hydrox-... 

Bu Lock JD, Shepherd D, Winstanley DJ (1969) Regulation of 6-Methylsalicylate and Pamlin Synthesis in Penicillium urticae. Can J Microbiol 15 279... 

Fig. 5.7. (a b) Biogenesis of patulin in Penicillium urticae (modified from Stoessl, 1981 used with permission of the copyright owner, Academic Press, New York). 

Additional data were subsequently obtained with diethyl [ C]malonate using the related organism Penicillium urticae (syn. P. patulum) and con-lirmed that malonate was not utilized for the priming reaction responsible for 6-methylsalicylate synthesis (Bu Lock et al., 1962). Application of these techniques verified that similar condensations by this acetate-malonate... 

Risi and Burke [29, 30] synthesized (+)-patulolide C, which is a macrocyhc compound isolated from a Penicillium urticae mutant via an asymmetric sequential hydroformylation-(intramolecular Wittig olefination) reaction applying... 

The ylidenebutenolide patulin (10) occupies a somewhat special place in organic chemistry. This structurally simple molecule, which is produced by the mold Penicillium urticae (synonym, P,patulum, P.flexuosum) was isolated independently by several groups of workers during the early 1940 s. It aroused immediate and widespread interest because of its potent antibiotic properties, but this interest evaporated almost as... 

Forrester, P. L, and G. M. Gaucher Conversion of 6-Methylsalicylic Acid into Patulin by Penicillium urticae. Biochemistry 11, 1102 (1972). 

It has been postulated that the antibiotic patulin, an unsaturated lactone produced by Penicillium urticae, is one of the most likely phytotoxins arising... 

Ehrensvard, G. Some observations on aromatic biosynthesis in Penicillium urticae Bainier. Exptl. Cell. Research, Suppl. 3, 102 (1955). 

L vova, L. E. Physiological characteristics of griseofulvin producers, Penicillium nigricans and Penicillium urticae, cultivated on synthetic media. Chem. Abstr. 63, 1191 (1965). 

Since this chapter was written, a new epoxide, isoepoxydon, was isolated (Sekiguchi and Gaucher, 1979 a,b Gaucher, 1979). Its structure was characterized as a partially reduced derivative of ( —)-phyllostine, and its stereochemistry was elucidated. Isoepoxydon was successfully converted into patulin by a cell-free preparation from Penicillium urticae, Isoepoxydon and phyllostine are interconvertible by an NADPH-dependent dehydrogenase. 

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