Penicillium roqueforti

Nielsen KF et ai, Production of metabolites from the Penicillium roqueforti complex., JAgric Food Chem 54 3756-3763, 2006. 

Esberg Boysen, M. (1999). In "Molecular Identification and quantification of the Penicillium roqueforti group", 154, Agraria Acta Universitatis Agriculturae Sueciae, Upsala (Doctoral Thesis, Swedish University of Agricultural Sciences) Upsala, 150 pp. 

Scheme 23.4 Production of methylketones from fatty acids by Penicillium roqueforti. 1 ATP-de-pendent acylcoenzyme A (acyl-CoA) synthase 2 flavin adenine dinucleotidedependent acyl-CoA dehydrogenase 3 enoyl-CoA hydratase 4 NAD-dependent 3-hydroxyacyl-CoA dehydrogenase 5 3-oxoacyl-CoA thiolase 6 3-oxoacyl-CoA thiolester hydrolase and 3-oxoacid decarboxylase. (Adapted from [46])...

Rhizomucor miehei secretes a lipase that is reported to give satisfactory results in Italian cheese manufacture. This enzyme has been characterized and is commercially available as Piccantase . Lipases secreted by selected strains of Penicillium roqueforti and P. candidum are considered to be potentially useful for the manufacture of Italian and other cheese varieties. 

Blue cheeses undergo very extensive lipolysis during ripening up to 25% of all fatty acids may be released. The principal lipase in Blue cheese is that produced by Penicillium roqueforti, with minor contributions from indigenous milk lipase and the lipases of starter and non-starter lactic acid bacteria. The free fatty acids contribute directly to the flavour of Blue cheeses but, more importantly, they undergo partial /J-oxidation to alkan-2-ones (methyl O... 

Figure 10.18 /1-Oxidation of fatty acids to methyl ketones by Penicillium roqueforti and subsequent reduction to secondary alcohols.

Kinsella, J.E. and Hwang, D.H. (1976) Enzymes of Penicillium roqueforti involved in the biosynthesis of cheese flavour. CRC Crtt. Rev. Food Sci. Nutr., 8, 191-228. 

Gripon, J. C., Desmazaud, M. J., Le Bars, D. and Bergere, J. L. 1977. Role of proteolytic enzymes of Streptococcus lactis, Penicillium roqueforti, and Penicillium caseicolum during cheese ripening. J. Dairy Sci., 60, 1532-1538. 

Kinsella, J. E. and Hwang, D. H. 1976. Methyl ketone formation during germination of Penicillium roqueforti. J. Agr. Food Chem. 24, 443-448. 

Czulak, J. 1960. Growth of Penicillium roqueforti on a whey medium. Aust. J. Dairy TechnoL 15, 118-120. 

Gripon, J. C. 1977B, The proteolytic system of Penicillium roqueforti. V. Purification and properties of an alkaline aminopeptidase. Biochemie 59, 679-686. 

Le Bairs, D. and Gripon, J. E. 1981. Role of Penicillium roqueforti proteinases during blue cheese ripening. J. Dairy Res. 48, 479-487. 

Trieu-Cuot, P. and Gripon, J. C. 1981. Casein hydrolysis by Penicillium caseicolum and Penicillium roqueforti proteinases A study with isoelectric focusing and two-dimensional electrophoresis. Neth Milk Dairy J. 35, 353-357. 

These alkaloids possess most unusual structural features, namely the 1-methoxyindoline ring, the two nitrogen atoms directly attached to position 2 of this ring, giving a triaminomethane type of structure, and a dimethylallyl group at position 3 of the indole system. A related alkaloid, roquefortine, has been isolated (76E140) from Penicillium roqueforti, but does not possess a 1-methoxyl group. 

Metabolites of the ergoline type [as (128)], as well as those of type (119), have been isolated from Penicillium roqueforti. The incorporation has been observed of radioactive samples of tryptophan and mevalonate into both series of metabolites, and of histidine into those of type (119).44 Diversion from tryptophan into the two independent biosynthetic pathways is initiated on the one hand by the formation of (122) and on the other by reaction with histidine to give a diketopiperazine precursor for metabolites such as (119). Which route is followed is temperature-dependent. 

A Russian group has isolated360 roquefortine and 3,17-dihydroroquefortine from Penicillium roqueforti Thom F-141 the latter metabolite is presumably identical with Alkaloid Z (roquefortine D), isolated from the same microorganism by Abe s group.36d... 

Secondary starter organisms (e.g., Penicillium roqueforti, P. camem-berti, Propionibacterium sp., smear bacteria)... 

Penicillium roqueforti and P. camemberti produce very active extracellular lipases, which are the principal lipolytic agents in mold-ripened cheeses. They preferentially hydrolyze the short-chain fatty acids in milk fat. P. roqueforti produces two lipases, one with an alkaline pH optimum and the other most active at pH 6 6.5, with slightly differing fatty acid specificities (Menassa and Lamberet, 1982). P. camemberti secretes a single lipase with optimal activity at pH 9 (Lamberet and Lenoir, 1976). 

Kinsella, J.E., Hwang, D. 1976. Biosynthesis of flavors by Penicillium roqueforti. Biotechnol. Bioeng. 18, 927-938. 

CARUTHERS, J. M., KANG, I., RYNKIEWICZ, M. J., CANE, D. E., CHRISTIANSON, D. W., Crystal structure determination of aristolochene synthase from the blue cheese mold, Penicillium roqueforti, J. Biol. Chem., 2000, 275, 25533-25539. 

A second stereoselective total synthesis of ( )-eremophilone (243) has been accomplished using 7-epinootkatone (242) as intermediate.109 The latter compound was synthesized from (—)-/3-pinene (241) by modification of the published procedure"0 and subsequently converted into eremophilone (243) by the series of functional-group transformations shown in Scheme 30. A mycotoxin isolated from Penicillium roqueforti has been assigned the highly oxygenated eremophilane structure (244) on the basis of chemical and spectroscopic evidence."1 The structure and... 

In 1976 Scott et al. (186) isolated the neurotoxin roquefortine (144) from the fungus Penicillium roqueforti. Structure 144 was deduced on the basis of spectroscopic data and degradative products. The alkaloid appeared to be the same as roquefortine C, isolated by Ohmomo et al. in 1975 (187). The latter authors confirmed the structure by spectroscopic evidence (188) they also isolated roquefortine D. Reduction of roquefortine D with zinc in acetic acid yielded two dihydro derivatives. The properties of roquefortine C and of one of the isomers correlated very well. Thus, roquefortine D is dihydro-roquefortine C (189). The stereochemistry still remains to be solved. 

The biosynthesis of roquefortine was investigated by feeding labeled mevalonic acid lactone, tryptophan, and histidine to Penicillium roqueforti these compounds were incorporated (190,191). A biogenetic pathway for roquefortine obtained from Stilton cheese has been suggested (191). 

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