Mycotoxins, drugs and other extrolites produced by species in Penicillium subgenus Penicillium

Jens Christian Frisvad, Jørn Smedsgaard, Thomas Ostenfeld Larsen, R.A. Samson

    Research output: Contribution to journalJournal articleResearchpeer-review

    Abstract

    The 58 species in Penicillium subgenus Penicillium produce a large number of bioactive extrolites (secondary metabolites), including several mycotoxins. An overview of these extrolites is presented with original references to the reports on their production and their chemical constitution. 132 extrolite families are reported from the subgenus with an average of 5 extrolite families per species. This is an underestimate as several pigments, volatiles and uncharacterized extrolites are not included in this average. Several reported producers are reidentified and new producers of known extrolites are reported for the first time. Several extrolites are unique for one species, but most of the metabolites are produced by more than one species. The most widespread extrolites were roquefortine C, which is produced by 25 species, the cyclopenins that are produced by 17 species, patulin which is produced by 13 species, penicillic acid which is produced by 10 species, and terrestric acid and 2-methyl isoborneol that are produced by 8 species. Most species produce both polyketides, terpenes and amino acid derived extrolites and a large number of the species produce bioactive metabolites. The nephrotoxic mycotoxin ochratoxin A is produced by P. verrucosum and P. nordicum, and another nephrotoxin, citrinin, is produced by P. expansum, P. radicicola and P. verrucosum. Patulin is produced by P. carneum, P. clavigerum, P. concentricum, P. coprobium, P. dipodomyicola, P. expansum, P. glandicola, P. gladioli, P. griseofulvum, P. marinum, P. paneum, P. sclerotigenum and P. vulpinum. Another polyketide mycotoxin, penicillic acid, is produced by P. aurantiogriseum, P. carneum, P. cyclopium, P. freii, P. melanoconidium, P. neoechinulatum, P. polonicum, P. radicicola, P. tulipae and P. viridicatum. The tremorgenic verrucosidin is produced by P. aurantiogriseum, P. melanoconidium and P. polonicum, while another tremorgen, penitrem A, is produced by P. carneum, P. clavigerum, P. crustosum, P. flavigenum, P. glandicola, P. melanoconidium and P. tulipae. Asteltoxin is produced by P. cavernicola, P. concentricum, P. confertum, P. formosanum and P. tricolor. The mutagenic mycotoxin botryodiploidin is produced by P. brevicompactum and P. paneum. The chaetoglobosins are produced by P. discolor, P. expansum and P. marinum. The cytotoxic communesins are produced by P. expansum and P. marinum. Cyclopiazonic acid is produced by P. camemberti, P. commune, P. dipodomyicola, P. griseofulvum and P. palitans. The fumitremorgins, verruculogen.. isochromantoxins and viriditoxin are produced by P. mononematosum. The immunosuppressive extrolite mycophenolic acid is produced by P. bialowiezense, P. brevicompactum, P. carneum and P. roqueforti. PR-toxin is produced by P. chrysogenum and P. roqueforti. Secalonic acid is produced by P. chrysogenum and P. confertum. The territrems are produced by P. cavernicola and P. echinulatum. Viridic acid is produced by P. nordicum and P. viridicatum, while viridicatumtoxin is produced by P. aethiopicum. The hepatotoxins xanthomegnin, viomellein and vioxanthin are produced by P. clavigerum, P. cyclopium, P. freii, P. melanoconidium, P. tricolor and P. viridicatum. Apart from these mycotoxins several alkaloids, such as festuclavine, rugulovasine, and roquefortine C are also produced by several species in Penicillium subgenus Penicillium. In most cases these extrolites are produced consistently by all isolates examined in a species. The important antibiotic penicillin is produced by all members of series Chrysogena and P. griseofulvum. The cholesterol-lowering agent compactin is produced by P. so A large number of interesting lead-compounds are produced by species in the subgenus.
    Original languageEnglish
    JournalStudies in Mycology
    Volume49
    Pages (from-to)201-241
    ISSN0166-0616
    Publication statusPublished - 2004

    Cite this

    @article{8d47dcb06f39462c982e7c235cfd2333,
    title = "Mycotoxins, drugs and other extrolites produced by species in Penicillium subgenus Penicillium",
    abstract = "The 58 species in Penicillium subgenus Penicillium produce a large number of bioactive extrolites (secondary metabolites), including several mycotoxins. An overview of these extrolites is presented with original references to the reports on their production and their chemical constitution. 132 extrolite families are reported from the subgenus with an average of 5 extrolite families per species. This is an underestimate as several pigments, volatiles and uncharacterized extrolites are not included in this average. Several reported producers are reidentified and new producers of known extrolites are reported for the first time. Several extrolites are unique for one species, but most of the metabolites are produced by more than one species. The most widespread extrolites were roquefortine C, which is produced by 25 species, the cyclopenins that are produced by 17 species, patulin which is produced by 13 species, penicillic acid which is produced by 10 species, and terrestric acid and 2-methyl isoborneol that are produced by 8 species. Most species produce both polyketides, terpenes and amino acid derived extrolites and a large number of the species produce bioactive metabolites. The nephrotoxic mycotoxin ochratoxin A is produced by P. verrucosum and P. nordicum, and another nephrotoxin, citrinin, is produced by P. expansum, P. radicicola and P. verrucosum. Patulin is produced by P. carneum, P. clavigerum, P. concentricum, P. coprobium, P. dipodomyicola, P. expansum, P. glandicola, P. gladioli, P. griseofulvum, P. marinum, P. paneum, P. sclerotigenum and P. vulpinum. Another polyketide mycotoxin, penicillic acid, is produced by P. aurantiogriseum, P. carneum, P. cyclopium, P. freii, P. melanoconidium, P. neoechinulatum, P. polonicum, P. radicicola, P. tulipae and P. viridicatum. The tremorgenic verrucosidin is produced by P. aurantiogriseum, P. melanoconidium and P. polonicum, while another tremorgen, penitrem A, is produced by P. carneum, P. clavigerum, P. crustosum, P. flavigenum, P. glandicola, P. melanoconidium and P. tulipae. Asteltoxin is produced by P. cavernicola, P. concentricum, P. confertum, P. formosanum and P. tricolor. The mutagenic mycotoxin botryodiploidin is produced by P. brevicompactum and P. paneum. The chaetoglobosins are produced by P. discolor, P. expansum and P. marinum. The cytotoxic communesins are produced by P. expansum and P. marinum. Cyclopiazonic acid is produced by P. camemberti, P. commune, P. dipodomyicola, P. griseofulvum and P. palitans. The fumitremorgins, verruculogen.. isochromantoxins and viriditoxin are produced by P. mononematosum. The immunosuppressive extrolite mycophenolic acid is produced by P. bialowiezense, P. brevicompactum, P. carneum and P. roqueforti. PR-toxin is produced by P. chrysogenum and P. roqueforti. Secalonic acid is produced by P. chrysogenum and P. confertum. The territrems are produced by P. cavernicola and P. echinulatum. Viridic acid is produced by P. nordicum and P. viridicatum, while viridicatumtoxin is produced by P. aethiopicum. The hepatotoxins xanthomegnin, viomellein and vioxanthin are produced by P. clavigerum, P. cyclopium, P. freii, P. melanoconidium, P. tricolor and P. viridicatum. Apart from these mycotoxins several alkaloids, such as festuclavine, rugulovasine, and roquefortine C are also produced by several species in Penicillium subgenus Penicillium. In most cases these extrolites are produced consistently by all isolates examined in a species. The important antibiotic penicillin is produced by all members of series Chrysogena and P. griseofulvum. The cholesterol-lowering agent compactin is produced by P. so A large number of interesting lead-compounds are produced by species in the subgenus.",
    author = "Frisvad, {Jens Christian} and J{\o}rn Smedsgaard and Larsen, {Thomas Ostenfeld} and R.A. Samson",
    year = "2004",
    language = "English",
    volume = "49",
    pages = "201--241",
    journal = "Studies in Mycology",
    issn = "0166-0616",
    publisher = "Centraalbureau voor Schimmelcultures",

    }

    Mycotoxins, drugs and other extrolites produced by species in Penicillium subgenus Penicillium. / Frisvad, Jens Christian; Smedsgaard, Jørn; Larsen, Thomas Ostenfeld; Samson, R.A.

    In: Studies in Mycology, Vol. 49, 2004, p. 201-241.

    Research output: Contribution to journalJournal articleResearchpeer-review

    TY - JOUR

    T1 - Mycotoxins, drugs and other extrolites produced by species in Penicillium subgenus Penicillium

    AU - Frisvad, Jens Christian

    AU - Smedsgaard, Jørn

    AU - Larsen, Thomas Ostenfeld

    AU - Samson, R.A.

    PY - 2004

    Y1 - 2004

    N2 - The 58 species in Penicillium subgenus Penicillium produce a large number of bioactive extrolites (secondary metabolites), including several mycotoxins. An overview of these extrolites is presented with original references to the reports on their production and their chemical constitution. 132 extrolite families are reported from the subgenus with an average of 5 extrolite families per species. This is an underestimate as several pigments, volatiles and uncharacterized extrolites are not included in this average. Several reported producers are reidentified and new producers of known extrolites are reported for the first time. Several extrolites are unique for one species, but most of the metabolites are produced by more than one species. The most widespread extrolites were roquefortine C, which is produced by 25 species, the cyclopenins that are produced by 17 species, patulin which is produced by 13 species, penicillic acid which is produced by 10 species, and terrestric acid and 2-methyl isoborneol that are produced by 8 species. Most species produce both polyketides, terpenes and amino acid derived extrolites and a large number of the species produce bioactive metabolites. The nephrotoxic mycotoxin ochratoxin A is produced by P. verrucosum and P. nordicum, and another nephrotoxin, citrinin, is produced by P. expansum, P. radicicola and P. verrucosum. Patulin is produced by P. carneum, P. clavigerum, P. concentricum, P. coprobium, P. dipodomyicola, P. expansum, P. glandicola, P. gladioli, P. griseofulvum, P. marinum, P. paneum, P. sclerotigenum and P. vulpinum. Another polyketide mycotoxin, penicillic acid, is produced by P. aurantiogriseum, P. carneum, P. cyclopium, P. freii, P. melanoconidium, P. neoechinulatum, P. polonicum, P. radicicola, P. tulipae and P. viridicatum. The tremorgenic verrucosidin is produced by P. aurantiogriseum, P. melanoconidium and P. polonicum, while another tremorgen, penitrem A, is produced by P. carneum, P. clavigerum, P. crustosum, P. flavigenum, P. glandicola, P. melanoconidium and P. tulipae. Asteltoxin is produced by P. cavernicola, P. concentricum, P. confertum, P. formosanum and P. tricolor. The mutagenic mycotoxin botryodiploidin is produced by P. brevicompactum and P. paneum. The chaetoglobosins are produced by P. discolor, P. expansum and P. marinum. The cytotoxic communesins are produced by P. expansum and P. marinum. Cyclopiazonic acid is produced by P. camemberti, P. commune, P. dipodomyicola, P. griseofulvum and P. palitans. The fumitremorgins, verruculogen.. isochromantoxins and viriditoxin are produced by P. mononematosum. The immunosuppressive extrolite mycophenolic acid is produced by P. bialowiezense, P. brevicompactum, P. carneum and P. roqueforti. PR-toxin is produced by P. chrysogenum and P. roqueforti. Secalonic acid is produced by P. chrysogenum and P. confertum. The territrems are produced by P. cavernicola and P. echinulatum. Viridic acid is produced by P. nordicum and P. viridicatum, while viridicatumtoxin is produced by P. aethiopicum. The hepatotoxins xanthomegnin, viomellein and vioxanthin are produced by P. clavigerum, P. cyclopium, P. freii, P. melanoconidium, P. tricolor and P. viridicatum. Apart from these mycotoxins several alkaloids, such as festuclavine, rugulovasine, and roquefortine C are also produced by several species in Penicillium subgenus Penicillium. In most cases these extrolites are produced consistently by all isolates examined in a species. The important antibiotic penicillin is produced by all members of series Chrysogena and P. griseofulvum. The cholesterol-lowering agent compactin is produced by P. so A large number of interesting lead-compounds are produced by species in the subgenus.

    AB - The 58 species in Penicillium subgenus Penicillium produce a large number of bioactive extrolites (secondary metabolites), including several mycotoxins. An overview of these extrolites is presented with original references to the reports on their production and their chemical constitution. 132 extrolite families are reported from the subgenus with an average of 5 extrolite families per species. This is an underestimate as several pigments, volatiles and uncharacterized extrolites are not included in this average. Several reported producers are reidentified and new producers of known extrolites are reported for the first time. Several extrolites are unique for one species, but most of the metabolites are produced by more than one species. The most widespread extrolites were roquefortine C, which is produced by 25 species, the cyclopenins that are produced by 17 species, patulin which is produced by 13 species, penicillic acid which is produced by 10 species, and terrestric acid and 2-methyl isoborneol that are produced by 8 species. Most species produce both polyketides, terpenes and amino acid derived extrolites and a large number of the species produce bioactive metabolites. The nephrotoxic mycotoxin ochratoxin A is produced by P. verrucosum and P. nordicum, and another nephrotoxin, citrinin, is produced by P. expansum, P. radicicola and P. verrucosum. Patulin is produced by P. carneum, P. clavigerum, P. concentricum, P. coprobium, P. dipodomyicola, P. expansum, P. glandicola, P. gladioli, P. griseofulvum, P. marinum, P. paneum, P. sclerotigenum and P. vulpinum. Another polyketide mycotoxin, penicillic acid, is produced by P. aurantiogriseum, P. carneum, P. cyclopium, P. freii, P. melanoconidium, P. neoechinulatum, P. polonicum, P. radicicola, P. tulipae and P. viridicatum. The tremorgenic verrucosidin is produced by P. aurantiogriseum, P. melanoconidium and P. polonicum, while another tremorgen, penitrem A, is produced by P. carneum, P. clavigerum, P. crustosum, P. flavigenum, P. glandicola, P. melanoconidium and P. tulipae. Asteltoxin is produced by P. cavernicola, P. concentricum, P. confertum, P. formosanum and P. tricolor. The mutagenic mycotoxin botryodiploidin is produced by P. brevicompactum and P. paneum. The chaetoglobosins are produced by P. discolor, P. expansum and P. marinum. The cytotoxic communesins are produced by P. expansum and P. marinum. Cyclopiazonic acid is produced by P. camemberti, P. commune, P. dipodomyicola, P. griseofulvum and P. palitans. The fumitremorgins, verruculogen.. isochromantoxins and viriditoxin are produced by P. mononematosum. The immunosuppressive extrolite mycophenolic acid is produced by P. bialowiezense, P. brevicompactum, P. carneum and P. roqueforti. PR-toxin is produced by P. chrysogenum and P. roqueforti. Secalonic acid is produced by P. chrysogenum and P. confertum. The territrems are produced by P. cavernicola and P. echinulatum. Viridic acid is produced by P. nordicum and P. viridicatum, while viridicatumtoxin is produced by P. aethiopicum. The hepatotoxins xanthomegnin, viomellein and vioxanthin are produced by P. clavigerum, P. cyclopium, P. freii, P. melanoconidium, P. tricolor and P. viridicatum. Apart from these mycotoxins several alkaloids, such as festuclavine, rugulovasine, and roquefortine C are also produced by several species in Penicillium subgenus Penicillium. In most cases these extrolites are produced consistently by all isolates examined in a species. The important antibiotic penicillin is produced by all members of series Chrysogena and P. griseofulvum. The cholesterol-lowering agent compactin is produced by P. so A large number of interesting lead-compounds are produced by species in the subgenus.

    M3 - Journal article

    VL - 49

    SP - 201

    EP - 241

    JO - Studies in Mycology

    JF - Studies in Mycology

    SN - 0166-0616

    ER -