Penicillium oxalicum

Larena, I., Melgarejo, R, and De Cal, A., Drying of conidia of Penicillium oxalicum, a biological control agent against Fusarium wilt of tomato, J. Phytopath., 151, 600, 2003. 

Larena, I. et al.. Biocontrol of Fusarium and Verticillium wilt of tomato by Penicillium oxalicum under greenhouse and field conditions, J. Phytopath, 151, 507, 2003. Hashem, A.M., Purification and properties of a milk-clotting enzyme produced by Penicillium oxalicum, Biores. Technol, 75, 219, 2000. 

Details of the elucidation of the structure of oxaline, a metabolite of the microfungus Penicillium oxalicum,33a have now been published.34... 

Oxaline (143) was isolated in 1974 by Nagel et al. (183,184) from cultures of the toxicogenic fungus Penicillium oxalicum. The compound may be classified as an indole alkaloid, but it is one of the three indole alkaloids known at present that also contains an imidazole substituent the other indole alkaloids being roquefortine (144) and neoxaline (145). The structure of oxaline was deduced from physicochemical data and confirmed by single-crystal X-ray analysis. It has been suggested that in the biosynthesis of oxaline, nature makes use of the amino acids tryptophan and histidine (184). 

A 500-inL flask with 100 inL of a medium (adjusted to pH 6.5) containing 1 % glucose and 1 % corn steep liquor is autoclaved at 120 C for 20 min. After cooling, the flask contents arc inoculated with spores from an agar slant culture of Penicillium oxalicum IFO 7000. The flask is then incubated at 26.5 °C for 2 d on a rotary shaking machine. 3/ -Hvdroxyandrost-5-en-17-one (1) is suspended in a 0.1 % Tween 80 soln under ultrasonication and added to the flask contents up to an end concentration of 5 g/L. The incubation is continued for 3 d under the above conditions. 10-mL samples are removed and extracted with 30 mL of EtOAc. A portion of the extract is analyzed by silica gel TLC (CllClyacetone 2 1 and cyclohexane/toluene/ EtOH 8 2 2.5), as well as by OLC yield 0.225 g (45.0%). 

Kadowaki S, Saskiawan I, Watanabe J, Yamamoto K, Bunno M, Ichihara Y, Kumagai H. Transglycosylation activity of P-A-acetylhexosaminidase from Penicillium oxalicum and its application to synthesis of a drug carrier. J. Perm. Bioeng. 1997 83 341-345. 

Many other examples of Az-peptides are listed in the literature and suggest that Az-amino acids are usually more stable than the E isomers [76]. However, some dehydropeptides like the neurotoxins roquefortine 11 and oxaline 12, isolated from Penicillium roqueforti and Penicillium oxalicum, respectively, both contain a A His residue (Fig. 13.13) [77]. Phomopsin A 13 (Fig. 13.13), an antimitotic agent produced by Phomopsis leptostromiformis, is also a A -peptide as it contains A Asp and A Ile residues [78,79]. 

The structure of oxaline (36), the principal alkaloid of a toxigenic strain of Penicillium oxalicum, represents a departure from those hitherto encountered in this area. The molecule possesses several unusual features, viz. the N—OMe group, the dehydrohistidine unit, the reversed isopentenyl group at C-3 (the only other example known to date is metabolite LL-S490j8), and the presence of three nitrogen functionalities attached to a single carbon atom (C-2). 

Oxaline was first isolated as a new alkaloid from a toxigenic strain of Penicillium oxalicum M-555. No bioactivity was reported for this compound which was originally characterized by x ray crystallography [64, 65]. 

Penicillium oxalicum was shown to produce two forms of glucoamylase and an a-D-glucosidase. The a-D-glucosidase has been isolated from the mycelia in an electrophoretically homogeneous form, and its properties have been investigated. The enzyme had a pH optimum at 3.5 with maltose as substrate. The enzyme hydrolysed maltose, maltotriose, phenyl a-maltoside, isomaltose, panose, isomaltotriose, amylose, and soluble starch liberating D-glucose, but not... 

Penicillium oxalicum has been shown to produce two forms of glucoamylase and an a-D-glucosidase. ... 

Liao H, Xu C, Tan S, WeiZ, Ling N, Yu G, Raza W, Zhang R, ShenQ,Xu Y. (2012). Production and characterization of acidophilic xylanolytic enzymes from Penicillium oxalicum GZ-2. Bioresour Technol, 123, 117-124. 

Kinoshita, T., and S. Minato Structural studies on anthglutin, an inhibitor of y-glutamyl transpeptidase, from Penicillium oxalicum. Bull. Chem. Soc. Japan 51, 3282 (1978). 

Roquefortine (Fig. 8) is a neurotoxic mold metabolite produced by Penicillium roqueforti that was first isolated by Polonsky et al. 1976 [43]. Roquefortine is also produced by Penicillium crustosum and Penicillium oxalicum. This substance is derived from the oxidative cyclization of tryptophan, histidine, and dimethylallyl pyrophosphate. 

Steyn and Vleggaar [50] have also studied the biosynthetic relationship between roquefortine and oxaline. The co-occurrence of roquefortine and oxaline in cultures of Penicillium oxalicum led these workers to speculate that roque-... 

Vinokurova NG, Reshetilova TA, Adanin VM, Kozlovskii AG (1991) Alkaloid composition of Penicillium palitans and Penicillium oxalicum. Appl Biochem Microbiol 27 644—648... 

---