메뉴 건너뛰기




Volumn 64, Issue 1, 2011, Pages 45-49

Genome mining and biosynthesis of fumitremorgin-type alkaloids in ascomycetes

Author keywords

biosynthesis; fumitremorgin type alkaloids; genome mining

Indexed keywords

ALKALOID; BREVIANAMIDE F; CYCLOTRYPROSTATIN; FUMITREMORGIN A; FUMITREMORGIN B; FUMITREMORGIN C; SPIROTRYPROSTATIN; TRYPROSTATIN A; TRYPROSTATIN B; UNCLASSIFIED DRUG; VERRUCULOGEN;

EID: 79251612101     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2010.128     Document Type: Review
Times cited : (47)

References (38)
  • 1
    • 73949099311 scopus 로고    scopus 로고
    • Prenylated indole derivatives from fungi: Structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis
    • Li, S.- M. Prenylated indole derivatives from fungi: Structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis. Nat. Prod. Rep. 27, 57-78 (2010).
    • (2010) Nat. Prod. Rep. , vol.27 , pp. 57-78
    • Li, S.-M.1
  • 2
    • 0000644470 scopus 로고    scopus 로고
    • Biosynthesis of prenylated alkaloids derived from tryptophan
    • Williams, R. M., Stocking, E. M. & Sanz-Cervera, J. F. Biosynthesis of prenylated alkaloids derived from tryptophan. Topics Curr. Chem. 209, 97-173 (2000).
    • (2000) Topics Curr. Chem. , vol.209 , pp. 97-173
    • Williams, R.M.1    Stocking, E.M.2    Sanz-Cervera, J.F.3
  • 3
    • 34249104049 scopus 로고    scopus 로고
    • Notoamides A-D: Prenylated indole alkaloids isolated from a marinederived fungus Aspergillus sp
    • Kato,H. et al. Notoamides A-D: Prenylated indole alkaloids isolated from a marinederived fungus, Aspergillus sp. Angew. Chem. Int. Ed. Engl. 46, 2254-2256 (2007).
    • (2007) Angew. Chem. Int. Ed. Engl. , vol.46 , pp. 2254-2256
    • Kato, H.1
  • 4
    • 77956422779 scopus 로고    scopus 로고
    • Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived Aspergillus sp
    • Ding,Y.et al. Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived Aspergillus sp. J. Am. Chem. Soc. 132, 12733-12740 (2010).
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 12733-12740
    • Ding, Y.1
  • 5
    • 0030036459 scopus 로고    scopus 로고
    • Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus: II. physico-chemical properties and structures
    • Cui, C. B., Kakeya, H. & Osada, H. Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. II. Physicochemical properties and structures. J. Antibiot. 49, 534-540 (1996). (Pubitemid 26235661)
    • (1996) Journal of Antibiotics , vol.49 , Issue.6 , pp. 534-540
    • Cui, C.-B.1    Kakeya, H.2    Osada, H.3
  • 6
    • 0030599282 scopus 로고    scopus 로고
    • Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase
    • Cui, C. B., Kakeya, H. & Osada, H. Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase. Tetrahedron 52, 12651-12666 (1996).
    • (1996) Tetrahedron , vol.52 , pp. 12651-12666
    • Cui, C.B.1    Kakeya, H.2    Osada, H.3
  • 7
    • 0031060189 scopus 로고    scopus 로고
    • Novel mammalian cell cycle inhibitors, cyclotryprostatins A-D, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase
    • Cui, C. B., Kakeya, H. & Osada, H. Novel mammalian cell cycle inhibitors, cyclotryprostatins A-D, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase. Tetrahedron 53, 59-72 (1997).
    • (1997) Tetrahedron , vol.53 , pp. 59-72
    • Cui, C.B.1    Kakeya, H.2    Osada, H.3
  • 8
    • 0031687689 scopus 로고    scopus 로고
    • Effects of tryprostatin derivatives on microtubule assembly in vitro and in situ
    • Kondoh, M., Usui, T., Mayumi, T. & Osada, H. Effects of tryprostatin derivatives on microtubule assembly in vitro and in situ. J. Antibiot. 51, 801-804 (1998).
    • (1998) J. Antibiot. , vol.51 , pp. 801-804
    • Kondoh, M.1    Usui, T.2    Mayumi, T.3    Osada, H.4
  • 9
    • 0037061593 scopus 로고    scopus 로고
    • Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines
    • Zhao, S. et al. Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines. J. Med. Chem. 45, 1559-1562 (2002).
    • (2002) J. Med. Chem. , vol.45 , pp. 1559-1562
    • Zhao, S.1
  • 10
    • 0033966957 scopus 로고    scopus 로고
    • Fumitremorgin C reverses multidrug resistance in cells transfected with the breast cancer resistance protein
    • Rabindran, S. K., Ross, D. D., Doyle, L. A., Yang, W. & Greenberger, L. M. Fumitremorgin C reverses multidrug resistance in cells transfected with the breast cancer resistance protein. Cancer Res. 60, 47-50 (2000).
    • (2000) Cancer Res. , vol.60 , pp. 47-50
    • Rabindran, S.K.1    Ross, D.D.2    Doyle, L.A.3    Yang, W.4    Greenberger, L.M.5
  • 11
    • 0000890967 scopus 로고    scopus 로고
    • Potent and specific inhibition of the breast cancer resistance protein multidrug transporter in vitro and in mouse intestine by a novel analogue of fumitremorgin C
    • Allen, J. D. et al. Potent and specific inhibition of the breast cancer resistance protein multidrug transporter in vitro and in mouse intestine by a novel analogue of fumitremorgin C. Mol. Cancer Ther. 1, 417-425 (2002).
    • (2002) Mol. Cancer Ther. , vol.1 , pp. 417-425
    • Allen, J.D.1
  • 12
    • 0242300545 scopus 로고    scopus 로고
    • Reversal of breast cancer resistance protein-mediated drug resistance by tryprostatin A
    • Woehlecke, H., Osada, H., Herrmann, A. & Lage, H. Reversal of breast cancer resistance protein-mediated drug resistance by tryprostatin A. Int. J. Cancer 107, 721-728 (2003).
    • (2003) Int. J. Cancer , vol.107 , pp. 721-728
    • Woehlecke, H.1    Osada, H.2    Herrmann, A.3    Lage, H.4
  • 13
    • 0015382691 scopus 로고
    • Tremorgenic toxin from Penicillium verruculosum
    • Cole, R. J. et al. Tremorgenic toxin from Penicillium verruculosum. Appl. Microbiol. 24, 248-250 (1972).
    • (1972) Appl. Microbiol. , vol.24 , pp. 248-250
    • Cole, R.J.1
  • 14
    • 37049130355 scopus 로고
    • Structure of fumitremorgin B (FTB), a tremorgenic toxin from Aspergillus fumigatus
    • Yamazaki, M., Sasago, K. & Miyaki, K. Structure of fumitremorgin B (FTB), a tremorgenic toxin from Aspergillus fumigatus. J. Chem. Soc. Chem. Commun. 408-409 (1974).
    • (1974) J. Chem. Soc. Chem. Commun. , pp. 408-409
    • Yamazaki, M.1    Sasago, K.2    Miyaki, K.3
  • 15
    • 0016813581 scopus 로고
    • Structure of a tremorgenic metabolite from Aspergillus fumigatus, fumitremorgin A
    • Yamazaki, M., Fujimoto, H. & Kawasaki, T. Structure of a tremorgenic metabolite from Aspergillus fumigatus, fumitremorgin A. Tetrahedron Lett. 1241-1244 (1975).
    • (1975) Tetrahedron Lett. , pp. 1241-1244
    • Yamazaki, M.1    Fujimoto, H.2    Kawasaki, T.3
  • 16
    • 33645693864 scopus 로고
    • Alkaloids from Aspergillus caespitosus
    • Steyn, P. S., Vleggaar, R. & Rabie, C. J. Alkaloids from Aspergillus caespitosus. Phytochemistry 20, 538-539 (1981).
    • (1981) Phytochemistry , vol.20 , pp. 538-539
    • Steyn, P.S.1    Vleggaar, R.2    Rabie, C.J.3
  • 17
    • 15944389537 scopus 로고    scopus 로고
    • Patulin produced by an Aspergillus clavatus isolated from feed containing malting residues associated with a lethal neurotoxicosis in cattle
    • Sabater-Vilar, M., Maas, R. F., De Bosschere, H., Ducatelle, R. & Fink-Gremmels, J. Patulin produced by an Aspergillus clavatus isolated from feed containing malting residues associated with a lethal neurotoxicosis in cattle. Mycopathologia 158, 419-426 (2004).
    • (2004) Mycopathologia , vol.158 , pp. 419-426
    • Sabater-Vilar, M.1    Maas, R.F.2    De Bosschere, H.3    Ducatelle, R.4    Fink-Gremmels, J.5
  • 18
    • 46649120278 scopus 로고    scopus 로고
    • Seven new prenylated indole diketopiperazine alkaloids from holothurian- derived fungus Aspergillus fumigatus
    • Wang, F. et al. Seven new prenylated indole diketopiperazine alkaloids from holothurian- derived fungus Aspergillus fumigatus. Tetrahedron 64, 7986-7991 (2008).
    • (2008) Tetrahedron , vol.64 , pp. 7986-7991
    • Wang, F.1
  • 19
    • 32744470433 scopus 로고
    • Productivity of tremorgenic mycotoxins, fumitremorgins A and B in Aspergillus fumigatus and allied species
    • Horie, Y. & Yamazaki, M. Productivity of tremorgenic mycotoxins, fumitremorgins A and B in Aspergillus fumigatus and allied species. Trans. Mycol. Soc. Jpn. 22, 113-119 (1981).
    • (1981) Trans. Mycol. Soc. Jpn. , vol.22 , pp. 113-119
    • Horie, Y.1    Yamazaki, M.2
  • 20
    • 0024024284 scopus 로고
    • Growth of and fumitremorgin production by Neosartorya fischeri as affected by temperature, light, and water activity
    • Nielsen, P. V., Beuchat, L. R. & Frisvad, J. C. Growth of and fumitremorgin production by Neosartorya fischeri as affected by temperature, light, and water activity. Appl. Environ. Microbiol. 54, 1504-1510 (1988).
    • (1988) Appl. Environ. Microbiol. , vol.54 , pp. 1504-1510
    • Nielsen, P.V.1    Beuchat, L.R.2    Frisvad, J.C.3
  • 21
    • 37049069793 scopus 로고
    • Stereochemical course of ring formation in fumitremorgin B and verruculogen, metabolites of Penicillium verruculosum: Investigation into the loss of stereochemical integrity of the geminal methyl groups
    • Vleggaar, R., Horak, R. M. & Maharaj, V. J. Stereochemical course of ring formation in fumitremorgin B and verruculogen, metabolites of Penicillium verruculosum: Investigation into the loss of stereochemical integrity of the geminal methyl groups. J. Chem. Soc. Chem. Commun. 274-275 (1993).
    • (1993) J. Chem. Soc. Chem. Commun. , pp. 274-275
    • Vleggaar, R.1    Horak, R.M.2    Maharaj, V.J.3
  • 22
    • 0017353822 scopus 로고
    • Production of the tremorgenic mycotoxins verruculogen and fumitremorgin B by Penicillium piscarium Westling
    • Gallagher, R. T. & Latch, G. C. M. Production of the tremorgenic mycotoxins verruculogen and fumitremorgin B by Penicillium piscarium Westling. Appl. Envir. Microbiol. 33, 730-731 (1977).
    • (1977) Appl. Envir. Microbiol. , vol.33 , pp. 730-731
    • Gallagher, R.T.1    Latch, G.C.M.2
  • 23
    • 0018849956 scopus 로고
    • Chemistry of tremorogenic metabolites. I. Fumitremorgin A from Aspergillus fumigatus
    • Yamazaki, M., Fujimoto, H. & Kawasaki, T. Chemistry of tremorogenic metabolites. I. Fumitremorgin A from Aspergillus fumigatus. Chem. Pharm. Bull. 28, 245-254 (1980).
    • (1980) Chem. Pharm. Bull. , vol.28 , pp. 245-254
    • Yamazaki, M.1    Fujimoto, H.2    Kawasaki, T.3
  • 24
    • 33847063916 scopus 로고    scopus 로고
    • Verruculogen associated with Aspergillus fumigatus hyphae and conidia modifies the electrophysiological properties of human nasal epithelial cells
    • Khoufache, K. et al. Verruculogen associated with Aspergillus fumigatus hyphae and conidia modifies the electrophysiological properties of human nasal epithelial cells. BMC. Microbiol. 7, 5 (2007).
    • (2007) BMC. Microbiol. , vol.7 , pp. 5
    • Khoufache, K.1
  • 25
    • 47549092638 scopus 로고    scopus 로고
    • Cytotoxic alkaloids and antibiotic nordammarane triterpenoids from the marine-derived fungus Aspergillus sydowi
    • Zhang, M. et al. Cytotoxic alkaloids and antibiotic nordammarane triterpenoids from the marine-derived fungus Aspergillus sydowi. J. Nat. Prod. 71, 985-989 (2008).
    • (2008) J. Nat. Prod. , vol.71 , pp. 985-989
    • Zhang, M.1
  • 26
    • 0023232162 scopus 로고
    • Biosynthesis of verruculogen, a tremorgenic metabolite of Penicillium verruculosum: Sterochemical course of peroxide ring formation
    • Horak, R. M. & Vleggaar, R. Biosynthesis of verruculogen, a tremorgenic metabolite of Penicillium verruculosum: Sterochemical course of peroxide ring formation. J. Chem. Soc. Chem. Commun. 1568-1570 (1987).
    • (1987) J. Chem. Soc. Chem. Commun. , pp. 1568-1570
    • Horak, R.M.1    Vleggaar, R.2
  • 27
    • 22144479730 scopus 로고    scopus 로고
    • Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus
    • Grundmann, A. & Li, S.- M. Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus. Microbiology 151, 2199-2207 (2005).
    • (2005) Microbiology , vol.151 , pp. 2199-2207
    • Grundmann, A.1    Li, S.-M.2
  • 28
    • 0033020953 scopus 로고    scopus 로고
    • Evidence for an ergot alkaloid gene cluster in Claviceps purpurea
    • Tudzynski, P. et al. Evidence for an ergot alkaloid gene cluster in Claviceps purpurea. Mol. Gen. Genet. 261, 133-141 (1999).
    • (1999) Mol. Gen. Genet. , vol.261 , pp. 133-141
    • Tudzynski, P.1
  • 29
    • 62349088498 scopus 로고    scopus 로고
    • Indole prenyltransferases from fungi: A new enzyme group with high potential for the production of prenylated indole derivatives
    • Steffan, N., Grundmann, A., Yin, W.- B., Kremer, A. & Li, S.- M. Indole prenyltransferases from fungi: A new enzyme group with high potential for the production of prenylated indole derivatives. Curr. Med. Chem. 16, 218-231 (2009).
    • (2009) Curr. Med. Chem. , vol.16 , pp. 218-231
    • Steffan, N.1    Grundmann, A.2    Yin, W.-B.3    Kremer, A.4    Li, S.-M.5
  • 31
    • 65549152187 scopus 로고    scopus 로고
    • Identification of cytochrome P450s required for fumitremorgin biosynthesis in Aspergillus fumigatus
    • Kato, N. et al. Identification of cytochrome P450s required for fumitremorgin biosynthesis in Aspergillus fumigatus. Chembiochem 10, 920-928 (2009).
    • (2009) Chembiochem , vol.10 , pp. 920-928
    • Kato, N.1
  • 32
    • 70349278483 scopus 로고    scopus 로고
    • FtmOx1, a non heme Fe(II) and alpha-ketoglutarate-dependent dioxygenase, catalyses the endoperoxide formation of verruculogen in Aspergillus fumigatus
    • Steffan, N., Grundmann, A., Afiyatullov, A., Ruan, H. & Li, S.- M. FtmOx1, a non heme Fe(II) and alpha-ketoglutarate-dependent dioxygenase, catalyses the endoperoxide formation of verruculogen in Aspergillus fumigatus. Org. Biomol. Chem. 7, 4082-4087 (2009).
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 4082-4087
    • Steffan, N.1    Grundmann, A.2    Afiyatullov, A.3    Ruan, H.4    Li, S.-M.5
  • 33
    • 33745905309 scopus 로고    scopus 로고
    • The fumitremorgin gene cluster of Aspergillus fumigatus: Identification of a gene encoding brevianamide F synthetase
    • Maiya, S., Grundmann, A., Li, S.- M. & Turner, G. The fumitremorgin gene cluster of Aspergillus fumigatus: Identification of a gene encoding brevianamide F synthetase. Chembiochem 7, 1062-1069 (2006).
    • (2006) Chembiochem , vol.7 , pp. 1062-1069
    • Maiya, S.1    Grundmann, A.2    Li, S.-M.3    Turner, G.4
  • 34
    • 64049086756 scopus 로고    scopus 로고
    • Improved tryprostatin B production by heterologous gene expression in Aspergillus nidulans
    • Maiya, S., Grundmann, A., Li, S.- M. & Turner, G. Improved tryprostatin B production by heterologous gene expression in Aspergillus nidulans. Fungal Genet. Biol. 46, 436-440 (2009).
    • (2009) Fungal Genet. Biol. , vol.46 , pp. 436-440
    • Maiya, S.1    Grundmann, A.2    Li, S.-M.3    Turner, G.4
  • 35
    • 54349101019 scopus 로고    scopus 로고
    • FtmPT2, an Nprenyltransferase from Aspergillus fumigatus, catalyses the last step in the biosynthesis of fumitremorgin B
    • Grundmann, A., Kuznetsova, T., Afiyatullov, S. S. & Li, S.- M. FtmPT2, an Nprenyltransferase from Aspergillus fumigatus, catalyses the last step in the biosynthesis of fumitremorgin B. Chembiochem 9, 2059-2063 (2008).
    • (2008) Chembiochem , vol.9 , pp. 2059-2063
    • Grundmann, A.1    Kuznetsova, T.2    Afiyatullov, S.S.3    Li, S.-M.4
  • 36
    • 2442628211 scopus 로고    scopus 로고
    • Fe(II)/alpha-ketoglutarate-dependent hydroxylases and related enzymes
    • Hausinger, R. P. Fe(II)/alpha-ketoglutarate-dependent hydroxylases and related enzymes. Crit. Rev. Biochem. Mol. Biol. 39, 21-68 (2004).
    • (2004) Crit. Rev. Biochem. Mol. Biol. , vol.39 , pp. 21-68
    • Hausinger, R.P.1
  • 37
    • 34248165513 scopus 로고    scopus 로고
    • Production of mycotoxins by Aspergillus lentulus and other medically important and closely related species in section Fumigati
    • Larsen, T. O. et al. Production of mycotoxins by Aspergillus lentulus and other medically important and closely related species in section Fumigati. Med. Mycol. 45, 225-232 (2007).
    • (2007) Med. Mycol. , vol.45 , pp. 225-232
    • Larsen, T.O.1
  • 38
    • 0029820050 scopus 로고    scopus 로고
    • Spirotryprostatin B, a novel mammalian cell cycle inhibitor produced by Aspergillus fumigatus [1]
    • Cui, C. B., Kakeya, H. & Osada, H. Spirotryprostatin B, a novel mammalian cell cycle inhibitor produced by Aspergillus fumigatus. J. Antibiot. 49, 832-835 (1996). (Pubitemid 26308326)
    • (1996) Journal of Antibiotics , vol.49 , Issue.8 , pp. 832-835
    • Cui, C.-B.1    Kakeya, H.2    Osada, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.