Penicillium viridicatum

This chemistry can be very powerful, since the amide product itself offers further possibilities for functionalization by lithiation. The synthesis of the natural product ochra-toxin A illustrates this point. Ochratoxins A 66 and B 67 (Scheme 34) are metabolites of Aspergillus ochraceus and Penicillium viridicatum whose presence in agricultural products... 

Benzodiazepine Alkaloids.—Cyclopenin (49) and cyclopenol (50) are isolated from Penicillium cyclopium. Their biosynthesis would appear to involve one molecule of phenylalanine and one of anthranilic acid and indeed the biosynthetic pathway to viridicatin and viridicatinol in Penicillium viridicatum from these two amino-acids has (49) and (50) as intermediates. ... 

The unique bicyclo[2,2,2]diazaoctane ring system constitutes one of the structural characteristics of brevianamides (Fig. (32)). Brevianamide A (144) was originally isolated from cultures of Penicillium brevicompactum by Birch and Wright in 1969 [98]. Brevianamide A (144) was also isolated from cultures of Penicillium viridicatum by Wilson and coworkers in 1973 [99]. Bird and coworkers observed that 144 is formed only after conidiation has begun in solid cultures of P. brevicompactum [100]. Birch and Russell isolated brevianamide B (145)... 

C30H31 NO,o, Mr565.58, light yellow cryst., mp. 235 °C (decomp.), [a] -12° (C2H5OH). Mycotoxin from Penicillium viridicatum. Biosynthetically, it is a nona-ketide with a monoterpene unit at C-6. V. is toxic (LD50 rat p.o. 122 mg/kg) and can be ingested with moldy food. 

Krogh P, Hasselager E, Friis P (1970) Fvmgal Nephrotoxicity. 2. Isolation of Two Nephrotoxic Compounds from Penicillium viridicatum citrinin and Oxalic Acid. Acta Pathol Microbiol Scand, B Microbiol Immunol 78 401... 

Aspergillus fumigatus, Mucor corticolus CBS, Rhizopus arrhizus (iBS, Streptomyces rimosus NRLL-2234,. V. scabies ATC C-3352, Streptomyces sp. PCC Penicillium viridicatum Euphorbia calyptrata plant cell culture Ipomoea (leaves)... 

Cyclopenase, an enzyme isolable from the mycelia of Penicillium viridicatum and Penicillium cyclopium, catalyses the transformation of the benzodiazepins (108 and 109) to the quinoline derivatives viridicatin (110) and viridicatol (111) ° . This rearrangement, which may also be accomplished with acids in vitro, is accompanied by the elimination of molar quantities of carbon dioxide and methylamine. 5-[ C]-Cyclopenin, biosynthesised from carboxyl labelled [ C]-anthranilic acid (29), gave viridicatin (110) which was devoid of radioactivity. All the radioactivity was found to be present in the carbon dioxide evolved. When the enzymatic transformation was carried out in, 0 or H2 0 there was no significant... 

Paecilomyces victoria Parmelia birulae Peltophorum interme Penicillium brevicompactum Penicillium canescens Penicillium citreo-viride Penicillium citrinum Penicillium cyclopium Penicillium duclauxi Penicillium herquei Penicillium stipitatum Penicillium thomii Penicillium viridicatum Peniophora sanguinea Periconia macrospinosa Pestalotia ramula Pseudomonas yoshitomiensis Pyricularia oryzae... 

Harwig, J., and Y.-K. Chen Some Conditions Favouring Production of Ochratoxin A and Citrinin by Penicillium viridicatum in Wheat and Barley. Canad. J. Plant Sd. 54,17 (1974). 

Scott, P.M., W. van Walbeek, J. Harwig, and D.I. Fennell Occurrence of a Mycotoxin, Ochratoxin A, in Wheat and Isolation of Ochratoxin A and Citrinin Producing Strains of Penicillium viridicatum. Canad. J. Plant Sci. 50, 583 (1970). Sedmera, P., j. Volc, j. Weijer, J. Vokoun, and V. Musilek Xanthomegnin and Viomellein Derivatives from Submerged Cultures of the Ascomycete Nannizzia caje-tani. Collect. Czech. Chem. Comm. 46, 1210 (1981). 

Stack, M.E., R.M. Eppley, P.A. Dreifuss, and A.E. Pohland Isolation and Identification of Xanthomegnin, Viomellein, Rubrosulphin, and Viopurpurin as Metabolites of Penicillium viridicatum. Appl. Environ. Microbiol. 33, 351 (1977). 

Stack, M.E., E.P. Mazzola, and R.M. Eppley Structures of Xanthoviridicatin D and Xanthoviridicatin G. Metabolites of Penicillium viridicatum Application of Proton and Carbon-13 NMR Spectroscopy. Tetrahedron Letters 1979, 4989. 

In the last decade, four nitrogen-containing heterocyclic products have been obtained from Penicillium viridicatum Westling and from PenicilUum cyclopium Westhng. The first of these viridicatin (LIV), 2,3-dihydroxy-4-phenylquinohne,... 

Cunningham, K. G., and G. G. Freeman The isolation and some chemical properties of viridicatin, a metabolic product of Penicillium viridicatum Westling. Bio-chem. J. 53, 328 (1953). 

The proliferation in the number of new and diverse fungal metabolites in recent years complicates a comprehensive survey of their biogenetic origin. The biosynthesis of many metabolites appears to be trivial, because a cursory chemical inspection of the structure allows the formulation of a plausible biosynthetic pathway. For many new metabolites, no toxicological data are available and only the structural elucidation together with a biosynthetic postulate is reported. Thus the biosynthetic origin of viridicatumtoxin (1), a toxic metabolite from Penicillium viridicatum (Kabuto et al., 1976), has not been studied, but is most probably closely modeled on that of the tetracyclines (McCormick, 1967). Similarly, verruculotoxin (2), isolated from cultures of Penicillium verruculosum, is most probably derived from two L-amino acids, phenylalanine and pipecolic acid (Macmillan et aL, 1976). 

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