Penitrems from Penicillium

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. 

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... 

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. 

In 1983, de Jesus and coworkers isolated tremorogenic mycotoxins named penitrems A (96), B (99), C (100), D (101), E (97), and F (102) from Penicillium cructosum [73, 75]. Penitrems and related compounds are shown in Fig. (17). Penitrems are indole alkaloids combined with... 

In 1992, Penn and coworkers isolated an analog of 96, pennigritrem (103), from Penicillium nigricans [77]. Pennigritrem (103) is a fungal indole-diterpenoid, but 103 has an oxetane ring, like taxol [78] and cephalomannine [79], unique among the members of penitrem family. 

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... 

The amino acid tryptophan is a precursor of several fungal metabolites that affect the central nervous system. We have already met it as a constituent of the ergot alkaloids. Roquefortine (9.25) is a metabolite of Penicillium roqueforti and P. camemberti, which are found on some cheeses. Roquefortine is one of a series of mycotoxins that affect the central nervous system and induce tremors. The more complex penitrems are tremorogenic neurotoxins that are produced by the P. crustosum series. They are biosynthesized from a tryptophan and a triterpene unit. 

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],... 

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]. 

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