Penicillium crustosum

Gonzalez MC, Lull C, Moya P, Ayala I, Primo J, Yufera EP (2003) Insecticidal Activity of Penitrems, Including Penitrem G, a New Member of the Family Isolated from Penicillium crustosum. J Agric Food Chem 51 2156... 

Rundberget T, Wilkins AL (2002) Thomitrems A and E, Two Indole-Alkaloid Isoprenoids from Penicillium crustosum Thom. Phytochemistry 61 979... 

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... 

Species of Penicillium fungi are rich sources of indole metabolites, such as thomitrem A 71 and thomitrem E 72, isolated from Penicillium crustosum <2002P979>. They are structurally similar to previously described penitrem derivatives <1996CHEC-II(2)207> but lack the characteristic penitrem 17(18)-ether linkage. 

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. 

Taiwan Penicillium citrinum, Penicillium crustosum, Penicillium implicatum... 

Indole-alkaloid isoprenoid was isolated from extracts of Penicillium crustosum grown on rice. This compound, designated thomitrem (53), contains a 18(19)-double bond and lacks the characteristic penitrem 17(18)-ether linkage [100],... 

Similar structural features are also demonstrated by penitrems A to F (Fig. 18), which form a small family of tremorgenic mycotoxins produced by the ergot fungus Penicillium crustosum. The structure of these alkaloids was elucidated by Steyn and co-workers (238-241), and an approach to the total synthesis of penitrem D was also presented (242). 

Penitrem D (226) (Scheme 41) is one member of the penitrem family, which is a small family of structurally complex tremorgenic mycotoxins, and was isolated from the ergot fungus Penicillium crustosum by Steyn and coworkers in 1981 [90]. 

Kawai K, Nozawa K, Yamaguchi T, Nakajima S, Udagawa S (1992) Two Chemotypes of Penicillium crustosum Based on the Analysis of Indolic Components. Mycotoxins 36 19... 

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. 

In a particularly provocative study, Gorst-Allman et al. fed [ 1,2--labeled acetate and [2,3- C]-labeled mevalonic acid lactone to cultures of Penicillium roqueforti and Penicillium crustosum [45] The NMR spectrum of the roquefortine showed that both C(26) and C(27) were coupled to C(23) (Fig. 9). This interesting result mandates that, during the incorporation of dimethylallyl pyrophosphate, the methyl groups become quasi-equivalent. 

The intermediacy of roquefortine in the biosynthesis of oxaline was established next using [benzene rmg-U- C, 6- C, 5- N] roquefortine obtained from cultures of Penicillium crustosum supplemented with (2RS)-[indole-2- C, 2-15N] tryptophan (incorporation 4.3 %, dilution 10.1). The labeled roquefortine was very efficiently incorporated into oxaline (24.3 %) but the relatively high dilution of 29.8 precluded the observation of the one-bond ( C- N)-coupling for the C(2) resonance in the NMR spectrum. 

Cole RJ, Domer JW, Cox RH, Raymond LW (1983) Two elasses of alkaloid myeotoxins produced by Penicillium crustosum Thom isolated from contaminated beer. J Agric Food Chem 31 655-657... 

Kawai, K., Nozawa, K., Yamaguchi, T., Nakajima, S. and Udagawa, S. (1992) Two chemotypes of Penicillium crustosum based on the analysis of indolic components. Proc.Jpn. Assoc. MycotoxicoL, 36,19-24. 

Cocculus laurifolius Papaver sormiferum Claviceps paspali Claviceps paspali Penicillium crustosum Cephalosporium aaremonium Penicillium chrysogenum Festuca arundinacea Pseudomonas aureofaciens Doliohothele sphaerioa Phoma lingam Pyrenoohaeta terrestris Deoodon vertidllatus,... 

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