Indoles from Penicillium crustosum

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

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. 

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],... 

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. 

Neurotoxic mycotoxins of the indole alkaloid type from many mold fungi of the genus Penicillium. e.g., P. roqueforti. P cyclopium, P. commune, P crustosum, P. chrysogenum, P. griseofulvum. The R. occur in blue cheese and cotton seeds and have also been found in beer. The main alkaloid is R. C. R. can lead to abortions in animal experiments. Today, toxin-free strains are used for the production of cheese. R. C and R. D are formed from tryptophan, histidine (diketopipera-zine part) and mevalonic acid. R. A and R.B are alkaloids of the clavine type (see ergot alkaloids). The LD50 for mice (i.p.) is 15 mg R.C/kg. 

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