Pencillium

Consonant with the present interest in chiral synthesis, two additional contributions can be cited. Sih al utilized a combined microbiological and organic chemical sequence in which key chirality establishing steps include the conversion of to chiral, but unstable, 18 by enzymic reduction using the fungus Diplodascus uninucleatus. Lower side-chain synthon was prepared by reduction of achiral with Pencillium decumbens. 

Succinic acid Turpentine oil Mycophenolic acid Pencillium brevi, compactum... 

Rob T et ai, A new compound from Pencillium thiomiiy an endophytic fungus, isolated from the root of Terminalia chebula Retz (Haritaki),/Bangladesh Chem... 

Modler, H., Brunner, J. R. and Stine, C. M. 1974. Extracellular protease of Pencillium roqueforti. II. Characterization of a purified enzyme preparation. J. Dairy Sci. 57, 528-534. 

Some of the most exciting natural products discovered in recent years are the cholesterollowering agents derived from fungi. These drugs inhibit 3-hydroxy-3-methylglutaryl coenzyme A reductase (HMG-COA reductase), an enzyme critical in the biosynthesis of cholesterol. The first HMG-COA reductase inhibitors were isolated from Pencillium sp. 

Menassa, A., Lamberet, G. 1982. Contribution a l etude du systeme lipolytique de Pencillium roqueforti. Caracteres compares de deux activites exocellulaires. Lait 62, 32-43. 

Streptomyces nodosus Streptomyces verticillus Cephalosporium sp. Saccharopolyspora erythraea Micromonospora purpurea Aspergillus terreus Streptomyces fradiae Pencillium chrysogenum Streptomyces ambofaciens Streptomyces aureofaciens Streptomyces orientalis... 

Citrinin is a benzopyran metabolite produced by the toxic strains of Pencillium ochraceus and Aspergillus verruco-sum. Some hepatotoxic effects have been reported for citrinin but the lethal effects are largely due to the nephrotoxicity. The specific mechanism of action in the kidneys is not known, but it leads to acute tubular necrosis. In pigs, rats, and rabbits, the proximal segments are affected. Histopathological findings in different species of animals... 

The first "statin" was discovered by Endo and coworkers at Sankyo in Tokyo in 1976. After testing over 8,000 microbial extracts, they found a compound, named mevastatin (ML-236B) (Figure 9), from Penicillium citrinum which showed specific inhibition of HMG CoA reductase and functioned in vivo, lowering serum cholesterol levels. Further development of mevastatin was curtailed because inhibition of cholesterol biosynthesis was not restricted to the liver. The compound enters the lens and adrenals, where it blocks the essential biosynthesis of cholesterol. The same compound was also isolated by a team at the Beecham Research Laboratories in Brockham Park, Surrey. Whilst screening for antifungal activity, they isolated the compound, which they named compactin, from Pencillium brevicompactum, but apparently failed to recognise it as a potent inhibitor of HMG CoA reductase. 

The j8-galactosidase from the Pencillium simplicissimum isolated from soil has high galactosyltransferase activity Synthesis of galactoohgosaccharides from 3 to 4 units of monosaccharide. When monosaccharides are present in the reaction system, the transfer activity of the enzyme will be inhibited, so only by the enzyme from P. simplicissimum cultured under the non-optimum hydrolysis conditions, galactooligosaccharide production can reach the maximum. For example, the lactose solution (concentration of 60%) incubated at pH 6.5 and 50 C obtained the maximum conversion rate. The product composition was 30.5% galacto-ohgosaccharide, 27.5% residual lactose and 42% free monosaccharides. 

Fig. 6.3 Pencillium ear rot caused by ochratoxin-producing fungi. (Courtesy of the University of Illinois Extension)...

Table 6.11 The structures of penicillins isolated from Pencillium chrysogenum.

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