Penicillium mycotoxin

Palal, Srinivasan A, Vig PVS, Desaiah D, Modulation ofcahnoduhn and protein kinase C activities by Penicillium mycotoxins, Int JToxicol 18 91—96, 1999. 

The natural product verrucofortine, 282, contains a pyrrolopyrrolopyrazine structural unit. This compound is a major metabolite of Penicillium verrucosum var. cyclopium, the fungus that produces the mycotoxin verrucosidin < 1988JNP66>. 

Most mycotoxin-producing Penicillium species are primarily known as storage pathogens however, some may be found in the field environment and these will be addressed here. 

Overy DP and Frisvad JC. 2005. Mycotoxin production and postharvest storage rot of ginger (Zingiber officinale) by Penicillium brevicompactum. J Food Prot 68 607-609. 

In the bacterium Penicillium chrysogenum the genomic PPTase is similar to others. When the gene was knocked out, the bacteria needed lysine to survive and no longer produced penicillin or pigmentation. However the bacterium still completed the syntheses of roquefortine, another mycotoxin, and fatty acids. This work suggests that the pptase gene is not needed for the synthesis of fatty acids and roquefortine in this species of bacteria. 

Penicillium spp. produce a wide range of mycotoxins, of which patulin (an unsaturated lactone) is common as a possible food contaminant. The species of this genus disseminate efficiently by the production of airborne conidia. 

Penicillium expansum is the major producer of the mycotoxins patulin and citrinin. Patulin is a mycotoxin mainly found in apple and apple products. P. expansum grows from 3 to 35°C, with an optimum of 25°C. Patulin is synthesized from 0 to 25°C with its optimum at 25°C. Citrinin is also produced along with patulin by P. expansum. 

Streptoverticillium album K-25l/ the antitumoral bis-indole alkaloids vinblastine and vincristine/ verruculogen, a very potent mycotoxin produced by several Penicillium species and melatonin, a hormone found in all living creatures from algae to humans, just to mention the most important ones. 

Ochratoxin, citrinin Contaminant (mycotoxin) Produced by Penicillium strains nephropathy (endemic Balkan nephropathy)... 

Neoxaline, C23H25N5O4, a new metabolite of Aspergillus japonicus, exhibits similarities to oxaline in its i.r. and n.m.r. spectra, and may be an indole derivative, but nothing further is known of its constitution as yet.38a Similarly, three new tremorgenic mycotoxins from Penicillium janthinellum, janthitrems A, B, and C, may also be indole derivatives.386... 

Botrytized wines, being produced from mold-affected grapes, might be expected to be contaminated with OTA. Although Botrytis itself has never been reported to produce mycotoxins, associated Penicillium and Aspergillus species might be involved in toxin production. To date, studies on botrytized wine have either not detected or found low OTA levels. 

The main metabolites of this group of fungi (Fusarium, Aspergillus, Penicillium, and Alternaria) are not only mycotoxins but also hormonally active compounds as well as enzymes, for instance amylase, chitinase, cellulase, glucanase, xylanase, or protease (Pawelzik et al. 1998). 

Six mycotoxins, penitrems A—F [(16a)—(16f)], derived from tryptophan (with loss of the side-chain) and a diterpene unit (with loss of a carbon atom), have been isolated from Penicillium crustosum iSe of these, penitrem A was first isolated15/in 1968 from P. cyclopium, and penitrems B and C in 197l15 from a micro-organism originally presumed to be P. palitans, but now classified as P. crustosum. The occurrence of penitrem A in P. cyclopium has recently been confirmed, and the presence of penitrem B was also demonstrated.156... 

Citreoviridin (79), luteoskyrin (80), and cyclochlorotine (81) are historical mycotoxins studied in Japan. Citreoviridin was isolated as a toxin from Penicillium citreoviride associated with a disease called cardiac beriberi or shoshin kakke .164 Luteoskyrin and cyclochlorotine were isolated from Penicillium islandicum, which was infected into toxic yellowed rice.165 Genes responsible for biosynthesis of these compounds are not obtained. 

Phomopsin A (83 in Figure 18) was isolated from Phomopsis leptostromiformis as the hepatotoxic metabolite responsible for lupinosis, which is a disease in animals caused by ingestion of Lupinus species infected with the fungus.169 Penicillium species produce other significant mycotoxins such as penitrem A (84), PR toxin (85), and rubratoxin B (86).170 Fusarin C (87) and fusaproliferin (88) are known as mycotoxins produced by Fusarium... 

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... 

Steyn PS Mycotoxins, general view, chemistry and structure. Toxicol Lett 1995 82 843-851. Yamaguchi T, Nozawa K, Hosoc T, Nakajima S, Kawai KL Indoloditerpenes related to tremorgenic mycotoxin penitrems, from Penicillium crustosum. Phytochemistry 1993 32 1177-1181. Penn J, Swift R, Wigley LJ, Mantle PG, Bilton JN, Sheppard RN Janthitrems B and C, two principal indole-diterpenoids produced by Penicillium janthinellum. Phytochemistry 1993 32 1431-1434. 

Another mycotoxin is patulin, produced by certain species of the moulds Penicillium and Aspergillus, which may grow on apples. There have been occasions when apple juice has been contaminated with patuhn but, provided producers remove infected apples and levels are monitored, there is not normally a danger from exposure (see Chapter 12). 

Mycotoxins are defined as mould derived secondary metabohtes and include Ochratoxin A (OTA). OTA, produced by Aspergillus ochraeus and Penicillium ver-rucosum, can be found as a contaminant in grain, beer, coffee and meat. OTA is nephrotoxic, hepatotoxic and carcinogenic [197]. 

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