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Volumn 6, Issue 12, 2014, Pages 3281-3295

Biosynthetic pathways of ergot alkaloids

Author keywords

Biosynthetic pathway; Ergot alkaloids; Fungi; Mycotoxins; Natural products; Secondary metabolism

Indexed keywords

ERGOCRYPTINE; ERGOMETRINE; ERGOT ALKALOID; ERGOTAMINE; LYSERGIC ACID; MYCOTOXIN; CHANOCLAVINE; ERGOLINE DERIVATIVE;

EID: 84919798995     PISSN: None     EISSN: 20726651     Source Type: Journal    
DOI: 10.3390/toxins6123281     Document Type: Review
Times cited : (93)

References (71)
  • 2
    • 85026471548 scopus 로고    scopus 로고
    • Ergot and its alkaloids
    • Schiff, P.L. Ergot and its alkaloids. Am. J. Pharm. Educ. 2006, 70, 1–10.
    • (2006) Am. J. Pharm. Educ , vol.70 , pp. 1-10
    • Schiff, P.L.1
  • 4
    • 79952014752 scopus 로고    scopus 로고
    • Ergot alkaloids: Structure diversity, biosynthetic gene clusters and functional proof of biosynthetic genes
    • Wallwey, C.; Li, S.M. Ergot alkaloids: Structure diversity, biosynthetic gene clusters and functional proof of biosynthetic genes. Nat. Prod. Rep. 2011, 28, 496–510.
    • (2011) Nat. Prod. Rep , vol.28 , pp. 496-510
    • Wallwey, C.1    Li, S.M.2
  • 6
    • 27644568753 scopus 로고    scopus 로고
    • Screening for ergot alkaloid producers among microscopic fungi by means of the polymerase chain reaction
    • Boichenko, L.V.; Boichenko, D.M.; Vinokurova, N.G.; Reshetilova, T.A.; Arinbasarov, M.U. Screening for ergot alkaloid producers among microscopic fungi by means of the polymerase chain reaction. Microbiology 2001, 70, 306–310.
    • (2001) Microbiology , vol.70 , pp. 306-310
    • Boichenko, L.V.1    Boichenko, D.M.2    Vinokurova, N.G.3    Reshetilova, T.A.4    Arinbasarov, M.U.5
  • 7
    • 84871932944 scopus 로고    scopus 로고
    • Parasitic fungus Claviceps as a source for biotechnological production of ergot alkaloids
    • Hulvova, H.; Galuszka, P.; Frebortova, J.; Frebort, I. Parasitic fungus Claviceps as a source for biotechnological production of ergot alkaloids. Biotechnol. Adv. 2013, 31, 79–89.
    • (2013) Biotechnol. Adv , vol.31 , pp. 79-89
    • Hulvova, H.1    Galuszka, P.2    Frebortova, J.3    Frebort, I.4
  • 8
    • 36649023737 scopus 로고    scopus 로고
    • Comparison of ergot alkaloid biosynthesis gene clusters in Claviceps species indicates loss of late pathway steps in evolution of C. Fusiformis
    • Lorenz, N.; Wilson, E.V.; Machado, C.; Schardl, C.L.; Tudzynski, P. Comparison of ergot alkaloid biosynthesis gene clusters in Claviceps species indicates loss of late pathway steps in evolution of C. fusiformis. Appl. Environ. Microbiol. 2007, 73, 7185–7191.
    • (2007) Appl. Environ. Microbiol , vol.73 , pp. 7185-7191
    • Lorenz, N.1    Wilson, E.V.2    Machado, C.3    Schardl, C.L.4    Tudzynski, P.5
  • 9
    • 79851472311 scopus 로고    scopus 로고
    • Genome sequencing and comparative transcriptomics of the model entomopathogenic fungi Metarhizium anisopliae and M. Acridum
    • Gao, Q.; Jin, K.; Ying, S.H.; Zhang, Y.; Xiao, G.; Shang, Y.; Duan, Z.; Hu, X.; Xie, X.Q.; Zhou, G.; et al. Genome sequencing and comparative transcriptomics of the model entomopathogenic fungi Metarhizium anisopliae and M. acridum. PLoS. Genet. 2011, doi:10.1371/journal.pgen.1001264.
    • (2011) Plos. Genet
    • Gao, Q.1    Jin, K.2    Ying, S.H.3    Zhang, Y.4    Xiao, G.5    Shang, Y.6    Duan, Z.7    Hu, X.8    Xie, X.Q.9    Zhou, G.10
  • 10
    • 79959916233 scopus 로고    scopus 로고
    • Physiological and biochemical characteristics of the genus Penicillium fungi as producers of ergot alkaloids and quinocitrinins
    • Kozlovsky, A.G.; Zhelifonova, V.P.; Antipova, T.V.; Zelenkova, N.F. Physiological and biochemical characteristics of the genus Penicillium fungi as producers of ergot alkaloids and quinocitrinins. Appl. Biochem. Microbiol. 2011, 47, 426–430.
    • (2011) Appl. Biochem. Microbiol , vol.47 , pp. 426-430
    • Kozlovsky, A.G.1    Zhelifonova, V.P.2    Antipova, T.V.3    Zelenkova, N.F.4
  • 11
    • 65649086400 scopus 로고    scopus 로고
    • Bioactive alkaloids from endophytic Aspergillus fumigatus
    • Ge, H.M.; Yu, Z.G.; Zhang, J.; Wu, J.H.; Tan, R.X. Bioactive alkaloids from endophytic Aspergillus fumigatus. J. Nat. Prod. 2009, 72, 753–755.
    • (2009) J. Nat. Prod , vol.72 , pp. 753-755
    • Ge, H.M.1    Yu, Z.G.2    Zhang, J.3    Wu, J.H.4    Tan, R.X.5
  • 12
    • 84871338784 scopus 로고    scopus 로고
    • Fungi of the genus Penicillium as producers of physiologically active compounds
    • Kozlovsky, A.G.; Zhelifonova, V.P.; Antipova, T.V. Fungi of the genus Penicillium as producers of physiologically active compounds. Appl. Biochem. Microbiol. 2013, 49, 1–10.
    • (2013) Appl. Biochem. Microbiol , vol.49 , pp. 1-10
    • Kozlovsky, A.G.1    Zhelifonova, V.P.2    Antipova, T.V.3
  • 13
    • 84861866197 scopus 로고    scopus 로고
    • Genome mining reveals the presence of a conserved gene cluster for the biosynthesis of ergot alkaloid precursors in the fungal family Arthrodermataceae
    • Wallwey, C.; Heddergott, C.; Xie, X.; Brakhage, A.A.; Li, S.M. Genome mining reveals the presence of a conserved gene cluster for the biosynthesis of ergot alkaloid precursors in the fungal family Arthrodermataceae. Microbiology 2012, 158, 1634–1644.
    • (2012) Microbiology , vol.158 , pp. 1634-1644
    • Wallwey, C.1    Heddergott, C.2    Xie, X.3    Brakhage, A.A.4    Li, S.M.5
  • 14
    • 84881375936 scopus 로고    scopus 로고
    • Differential allocation of seed-borne ergot alkaloids during early ontogeny of morning glories (Convolvulaceae)
    • Beaulieu, W.T.; Panaccione, D.G.; Hazekamp, C.S.; Mckee, M.C.; Ryan, K.L.; Clay, K. Differential allocation of seed-borne ergot alkaloids during early ontogeny of morning glories (Convolvulaceae). J. Chem. Ecol. 2013, 39, 919–930.
    • (2013) J. Chem. Ecol , vol.39 , pp. 919-930
    • Beaulieu, W.T.1    Panaccione, D.G.2    Hazekamp, C.S.3    McKee, M.C.4    Ryan, K.L.5    Clay, K.6
  • 15
    • 50649097975 scopus 로고    scopus 로고
    • Biosynthesis and accumulation of ergoline alkaloids in a mutualistic association between Ipomoea asarifolia (Convolvulaceae) and a Clavicipitalean fungus
    • Markert, A.; Steffan, N.; Ploss, K.; Hellwig, S.; Steiner, U.; Drewke, C.; Li, S.M.; Boland, W.; Leistner, E. Biosynthesis and accumulation of ergoline alkaloids in a mutualistic association between Ipomoea asarifolia (Convolvulaceae) and a Clavicipitalean fungus. Plant Physiol. 2008, 147, 296–305.
    • (2008) Plant Physiol , vol.147 , pp. 296-305
    • Markert, A.1    Steffan, N.2    Ploss, K.3    Hellwig, S.4    Steiner, U.5    Drewke, C.6    Li, S.M.7    Boland, W.8    Leistner, E.9
  • 18
    • 77956679296 scopus 로고    scopus 로고
    • Biochemistry of ergot alkaloids—Achievements and challenges
    • Gröger, D.; Floss, H.G. Biochemistry of ergot alkaloids—Achievements and challenges. Alkaloids Chem. Biol. 1998, 50, 171–218.
    • (1998) Alkaloids Chem. Biol , vol.50 , pp. 171-218
    • Gröger, D.1    Floss, H.G.2
  • 19
    • 0028261642 scopus 로고
    • Structural study of alkaloids from Securidaca longipedunculata roots II. Isolation and characterization by supercritical fluid chromatography/mass spectrometry
    • Scandola, M.; Games, D.E.; Costa, C.; Allegri, G.; Bertazzo, A.; Curcuruto, O.; Traldi, P. Structural study of alkaloids from Securidaca longipedunculata roots II. Isolation and characterization by supercritical fluid chromatography/mass spectrometry. J. Heterocycl. Chem. 1994, 31, 219–224.
    • (1994) J. Heterocycl. Chem , vol.31 , pp. 219-224
    • Scandola, M.1    Games, D.E.2    Costa, C.3    Allegri, G.4    Bertazzo, A.5    Curcuruto, O.6    Traldi, P.7
  • 20
    • 33750412469 scopus 로고    scopus 로고
    • Post genome research on the biosynthesis of ergot alkaloids
    • Li, S.M.; Unsöld, I.A. Post genome research on the biosynthesis of ergot alkaloids. Planta Med. 2006, 72, 1117–1120.
    • (2006) Planta Med , vol.72 , pp. 1117-1120
    • Li, S.M.1    Unsöld, I.A.2
  • 21
    • 0017228327 scopus 로고
    • Biosynthesis of ergot alkaloids and related compounds
    • Floss, H.G. Biosynthesis of ergot alkaloids and related compounds. Tetrahedron 1976, 32, 873–912.
    • (1976) Tetrahedron , vol.32 , pp. 873-912
    • Floss, H.G.1
  • 22
    • 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. Top. Curr. Chem. 2000, 209, 97–173.
    • (2000) Top. Curr. Chem , vol.209 , pp. 97-173
    • Williams, R.M.1    Stocking, E.M.2    Sanz-Cervera, J.F.3
  • 23
    • 0026751389 scopus 로고
    • Purification and characterization of dimethylallyl tryptophan synthase from Claviceps purpurea
    • Gebler, J.C.; Poulter, C.D. Purification and characterization of dimethylallyl tryptophan synthase from Claviceps purpurea. Arch. Biochem. Biophys. 1992, 296, 308–313.
    • (1992) Arch. Biochem. Biophys , vol.296 , pp. 308-313
    • Gebler, J.C.1    Poulter, C.D.2
  • 24
    • 0028858379 scopus 로고
    • The Claviceps purpurea gene encoding dimethylallyltryptophan synthase, the committed step for ergot alkaloid biosynthesis
    • Tsai, H.F.; Wang, H.; Gebler, J.C.; Poulter, C.D.; Schardl, C.L. The Claviceps purpurea gene encoding dimethylallyltryptophan synthase, the committed step for ergot alkaloid biosynthesis. Biochem. Biophys. Res. Commun. 1995, 216, 119–125.
    • (1995) Biochem. Biophys. Res. Commun , vol.216 , pp. 119-125
    • Tsai, H.F.1    Wang, H.2    Gebler, J.C.3    Poulter, C.D.4    Schardl, C.L.5
  • 26
    • 20444414907 scopus 로고    scopus 로고
    • The ergot alkaloid gene cluster in Claviceps purpurea: Extension of the cluster sequence and intra species evolution
    • Haarmann, T.; Machado, C.; Lübbe, Y.; Correia, T.; Schardl, C.L.; Panaccione, D.G.; Tudzynski, P. The ergot alkaloid gene cluster in Claviceps purpurea: Extension of the cluster sequence and intra species evolution. Phytochemistry 2005, 66, 1312–1320.
    • (2005) Phytochemistry , vol.66 , pp. 1312-1320
    • Haarmann, T.1    Machado, C.2    Lübbe, Y.3    Correia, T.4    Schardl, C.L.5    Panaccione, D.G.6    Tudzynski, P.7
  • 27
    • 70350742023 scopus 로고    scopus 로고
    • The ergot alkaloid gene cluster: Functional analyses and evolutionary aspects
    • Lorenz, N.; Haarmann, T.; Pazoutova, S.; Jung, M.; Tudzynski, P. The ergot alkaloid gene cluster: Functional analyses and evolutionary aspects. Phytochemistry 2009, 70, 1822–1932.
    • (2009) Phytochemistry , vol.70 , pp. 1822-1932
    • Lorenz, N.1    Haarmann, T.2    Pazoutova, S.3    Jung, M.4    Tudzynski, P.5
  • 28
    • 36049021933 scopus 로고    scopus 로고
    • Use of a nonhomologous end joining deficient strain (Deltaku70) of the ergot fungus Claviceps purpurea for identification of a nonribosomal peptide synthetase gene involved in ergotamine biosynthesis
    • Haarmann, T.; Lorenz, N.; Tudzynski, P. Use of a nonhomologous end joining deficient strain (Deltaku70) of the ergot fungus Claviceps purpurea for identification of a nonribosomal peptide synthetase gene involved in ergotamine biosynthesis. Fungal Genet. Biol. 2008, 45, 35–44.
    • (2008) Fungal Genet. Biol , vol.45 , pp. 35-44
    • Haarmann, T.1    Lorenz, N.2    Tudzynski, P.3
  • 31
    • 20444396966 scopus 로고    scopus 로고
    • Abundant respirable ergot alkaloids from the common airborne fungus Aspergillus fumigatus
    • Panaccione, D.G.; Coyle, C.M. Abundant respirable ergot alkaloids from the common airborne fungus Aspergillus fumigatus. Appl. Environ. Microbiol. 2005, 71, 3106–3111.
    • (2005) Appl. Environ. Microbiol , vol.71 , pp. 3106-3111
    • Panaccione, D.G.1    Coyle, C.M.2
  • 33
    • 0017176386 scopus 로고
    • Purification and properties of dimethylallylpyrophosphate: Tryptophan dimethylallyl transferase, the first enzyme of ergot alkaloid biosynthesis in Claviceps. sp. SD 58
    • Lee, S.L.; Floss, H.G.; Heinstein, P. Purification and properties of dimethylallylpyrophosphate: Tryptophan dimethylallyl transferase, the first enzyme of ergot alkaloid biosynthesis in Claviceps. sp. SD 58. Arch. Biochem. Biophys. 1976, 177, 84–94.
    • (1976) Arch. Biochem. Biophys , vol.177 , pp. 84-94
    • Lee, S.L.1    Floss, H.G.2    Heinstein, P.3
  • 34
    • 20444387174 scopus 로고    scopus 로고
    • An ergot alkaloid biosynthesis gene and clustered hypothetical genes from Aspergillus fumigatus
    • Coyle, C.M.; Panaccione, D.G. An ergot alkaloid biosynthesis gene and clustered hypothetical genes from Aspergillus fumigatus. Appl. Environ. Microbiol. 2005, 71, 3112–3118.
    • (2005) Appl. Environ. Microbiol , vol.71 , pp. 3112-3118
    • Coyle, C.M.1    Panaccione, D.G.2
  • 35
    • 19044365898 scopus 로고    scopus 로고
    • Overproduction, purification and characterization of FgaPT2, a dimethylallyltryptophan synthase from Aspergillus fumigatus
    • Unsöld, I.A.; Li, S.M. Overproduction, purification and characterization of FgaPT2, a dimethylallyltryptophan synthase from Aspergillus fumigatus. Microbiology 2005, 151, 1499–1505.
    • (2005) Microbiology , vol.151 , pp. 1499-1505
    • Unsöld, I.A.1    Li, S.M.2
  • 36
    • 34547450158 scopus 로고    scopus 로고
    • Chemoenzymatic synthesis of prenylated indole derivatives by using a 4-dimethylallyltryptophan synthase from Aspergillus fumigatus
    • Steffan, N.; Unsöld, I.A.; Li, S.M. Chemoenzymatic synthesis of prenylated indole derivatives by using a 4-dimethylallyltryptophan synthase from Aspergillus fumigatus. Chembiochem 2007, 8, 1298–1307.
    • (2007) Chembiochem , vol.8 , pp. 1298-1307
    • Steffan, N.1    Unsöld, I.A.2    Li, S.M.3
  • 37
    • 67349244074 scopus 로고    scopus 로고
    • Increasing structure diversity of prenylated diketopiperazine derivatives by using a 4-dimethylallyltryptophan synthase
    • Steffan, N.; Li, S.M. Increasing structure diversity of prenylated diketopiperazine derivatives by using a 4-dimethylallyltryptophan synthase. Arch. Microbiol. 2009, 191, 461–466.
    • (2009) Arch. Microbiol , vol.191 , pp. 461-466
    • Steffan, N.1    Li, S.M.2
  • 38
    • 70149099367 scopus 로고    scopus 로고
    • The structure of dimethylallyl tryptophan synthase reveals a common architecture of aromatic prenyltransferases in fungi and bacteria
    • Metzger, U.; Schall, C.; Zocher, G.; Unsöld, I.; Stec, E.; Li, S.-M.; Heide, L.; Stehle, T. The structure of dimethylallyl tryptophan synthase reveals a common architecture of aromatic prenyltransferases in fungi and bacteria. Proc. Natl. Acad. Sci. USA 2009, 106, 14309–14314.
    • (2009) Proc. Natl. Acad. Sci. USA , vol.106 , pp. 14309-14314
    • Metzger, U.1    Schall, C.2    Zocher, G.3    Unsöld, I.4    Stec, E.5    Li, S.-M.6    Heide, L.7    Stehle, T.8
  • 39
    • 70349620845 scopus 로고    scopus 로고
    • Mechanism of dimethylallyltryptophan synthase: Evidence for a dimethylallyl cation intermediate in an aromatic prenyltransferase reaction
    • Luk, L.Y.P.; Tanner, M.E. Mechanism of dimethylallyltryptophan synthase: Evidence for a dimethylallyl cation intermediate in an aromatic prenyltransferase reaction. J. Am. Chem. Soc. 2009, 131, 13932–13933.
    • (2009) J. Am. Chem. Soc , vol.131 , pp. 13932-13933
    • Luk, L.1    Tanner, M.E.2
  • 40
    • 68149159889 scopus 로고    scopus 로고
    • Phylogenetic analyses reveal monophyletic origin of the ergot alkaloid gene dmaW in fungi
    • Liu, M.; Panaccione, D.G.; Schardl, C.L. Phylogenetic analyses reveal monophyletic origin of the ergot alkaloid gene dmaW in fungi. Evol. Bioinform. 2009, 5, 15–30.
    • (2009) Evol. Bioinform , vol.5 , pp. 15-30
    • Liu, M.1    Panaccione, D.G.2    Schardl, C.L.3
  • 41
    • 84867031524 scopus 로고    scopus 로고
    • Prenyltransferases of the dimethylallyltryptophan synthase superfamily
    • Yu, X.; Li, S.M. Prenyltransferases of the dimethylallyltryptophan synthase superfamily. Methods Enzymol. 2012, 516, 259–278.
    • (2012) Methods Enzymol , vol.516 , pp. 259-278
    • Yu, X.1    Li, S.M.2
  • 42
    • 84868218912 scopus 로고    scopus 로고
    • Expansion of enzymatic Friedel-Crafts alkylation on indoles: Acceptance of unnatural beta-unsaturated allyl diphospates by dimethylallyl-tryptophan synthases
    • Liebhold, M.; Xie, X.; Li, S.-M. Expansion of enzymatic Friedel-Crafts alkylation on indoles: Acceptance of unnatural beta-unsaturated allyl diphospates by dimethylallyl-tryptophan synthases. Org. Lett. 2012, 14, 4884–4885.
    • (2012) Org. Lett , vol.14 , pp. 4884-4885
    • Liebhold, M.1    Xie, X.2    Li, S.-M.3
  • 43
    • 84887936603 scopus 로고    scopus 로고
    • Regiospecific benzylation of tryptophan and derivatives catalyzed by a fungal dimethylallyl transferase
    • Liebhold, M.; Li, S.M. Regiospecific benzylation of tryptophan and derivatives catalyzed by a fungal dimethylallyl transferase. Org. Lett. 2013, 15, 5834–5837.
    • (2013) Org. Lett , vol.15 , pp. 5834-5837
    • Liebhold, M.1    Li, S.M.2
  • 44
    • 69949164572 scopus 로고    scopus 로고
    • Applications of dimethylallyltryptophan synthases and other indole prenyltransferases for structural modification of natural products
    • Li, S.M. Applications of dimethylallyltryptophan synthases and other indole prenyltransferases for structural modification of natural products. Appl. Microbiol. Biotechnol. 2009, 84, 631–639.
    • (2009) Appl. Microbiol. Biotechnol , vol.84 , pp. 631-639
    • Li, S.M.1
  • 45
    • 55249116787 scopus 로고    scopus 로고
    • Ergot alkaloid biosynthesis in Aspergillus fumigatus: Overproduction and biochemical characterisation of a 4-dimethylallyltryptophan N-methyltransferase
    • Rigbers, O.; Li, S.M. Ergot alkaloid biosynthesis in Aspergillus fumigatus: Overproduction and biochemical characterisation of a 4-dimethylallyltryptophan N-methyltransferase. J. Biol. Chem. 2008, 283, 26859–26868.
    • (2008) J. Biol. Chem , vol.283 , pp. 26859-26868
    • Rigbers, O.1    Li, S.M.2
  • 46
    • 77749260568 scopus 로고    scopus 로고
    • The alkaloid cluster gene ccsA of the ergot fungus Claviceps purpurea encodes the chanoclavine-I-synthase, an FAD-containing oxidoreductase mediating the transformation of N-methyl-dimethylallyltryptophan to chanoclavine-I
    • Lorenz, N.; Olšovská, J.; Šulc, M.; Tudzynski, P. The alkaloid cluster gene ccsA of the ergot fungus Claviceps purpurea encodes the chanoclavine-I-synthase, an FAD-containing oxidoreductase mediating the transformation of N-methyl-dimethylallyltryptophan to chanoclavine-I. Appl. Environ. Microbiol. 2010, 76, 1822–1830.
    • (2010) Appl. Environ. Microbiol , vol.76 , pp. 1822-1830
    • Lorenz, N.1    Olšovská, J.2    Šulc, M.3    Tudzynski, P.4
  • 47
    • 79958280118 scopus 로고    scopus 로고
    • Ergot cluster-encoded catalase is required for synthesis of chanoclavine-I in Aspergillus fumigatus
    • Goetz, K.E.; Coyle, C.M.; Cheng, J.Z.; O’Connor, S.E.; Panaccione, D.G. Ergot cluster-encoded catalase is required for synthesis of chanoclavine-I in Aspergillus fumigatus. Curr. Genet. 2011, 57, 201–211.
    • (2011) Curr. Genet , vol.57 , pp. 201-211
    • Goetz, K.E.1    Coyle, C.M.2    Cheng, J.Z.3    O’Connor, S.E.4    Panaccione, D.G.5
  • 48
    • 0010739008 scopus 로고
    • Probing ergot alkaloid biosynthesis: Intermediates in the formation of ring C
    • Kozikowski, A.P.; Chen, C.; Wu, J.P.; Shibuya, M.; Kim, C.G.; Floss, H.G. Probing ergot alkaloid biosynthesis: Intermediates in the formation of ring C. J. Am. Chem. Soc. 1993, 115, 2482–2488.
    • (1993) J. Am. Chem. Soc , vol.115 , pp. 2482-2488
    • Kozikowski, A.P.1    Chen, C.2    Wu, J.P.3    Shibuya, M.4    Kim, C.G.5    Floss, H.G.6
  • 49
    • 84875264267 scopus 로고    scopus 로고
    • Partial reconstruction of the ergot alkaloid pathway by heterologous gene expression in Aspergillus nidulans
    • Ryan, K.L.; Moore, C.T.; Panaccione, D.G. Partial reconstruction of the ergot alkaloid pathway by heterologous gene expression in Aspergillus nidulans. Toxins 2013, 5, 445–455.
    • (2013) Toxins , vol.5 , pp. 445-455
    • Ryan, K.L.1    Moore, C.T.2    Panaccione, D.G.3
  • 50
    • 84908115795 scopus 로고    scopus 로고
    • The important ergot alkaloid intermediate chanoclavine-I produced in the yeast Saccharomyces cerevisiae by the combined action of EasC and EasE from Aspergillus japonicus
    • Nielsen, C.; Folly, C.; Hatsch, A.; Molt, A.; Schroder, H.; O’Connor, S.E.; Naesby, M. The important ergot alkaloid intermediate chanoclavine-I produced in the yeast Saccharomyces cerevisiae by the combined action of EasC and EasE from Aspergillus japonicus. Microb. Cell Fact. 2014, 13, doi:10.1186/s12934-014-0095-2.
    • (2014) Microb. Cell Fact , vol.13
    • Nielsen, C.1    Folly, C.2    Hatsch, A.3    Molt, A.4    Schroder, H.5    O’Connor, S.E.6    Naesby, M.7
  • 51
    • 76949092773 scopus 로고    scopus 로고
    • Ergot alkaloid biosynthesis in Aspergillus fumigatus: Conversion of chanoclavine-I to chanoclavine-I aldehyde catalyzed by a short-chain alcohol dehydrogenase FgaDH
    • Wallwey, C.; Matuschek, M.; Li, S.M. Ergot alkaloid biosynthesis in Aspergillus fumigatus: Conversion of chanoclavine-I to chanoclavine-I aldehyde catalyzed by a short-chain alcohol dehydrogenase FgaDH. Arch. Microbiol. 2010, 192, 127–134.
    • (2010) Arch. Microbiol , vol.192 , pp. 127-134
    • Wallwey, C.1    Matuschek, M.2    Li, S.M.3
  • 52
    • 84863102933 scopus 로고    scopus 로고
    • In vitro conversion of chanoclavine-I aldehyde to the stereoisomers festuclavine and pyroclavine controlled by the second reduction step
    • Matuschek, M.; Wallwey, C.; Wollinsky, B.; Xie, X.; Li, S.M. In vitro conversion of chanoclavine-I aldehyde to the stereoisomers festuclavine and pyroclavine controlled by the second reduction step. RSC Adv. 2012, 2, 3662–3669.
    • (2012) RSC Adv , vol.2 , pp. 3662-3669
    • Matuschek, M.1    Wallwey, C.2    Wollinsky, B.3    Xie, X.4    Li, S.M.5
  • 53
    • 77953634748 scopus 로고    scopus 로고
    • An old yellow enzyme gene that controls the branch point between Aspergillus fumigatus and Claviceps purpurea ergot alkaloid pathways
    • Coyle, C.M.; Cheng, J.Z.; O’Connor, S.E.; Panaccione, D.G. An old yellow enzyme gene that controls the branch point between Aspergillus fumigatus and Claviceps purpurea ergot alkaloid pathways. Appl. Environ. Microbiol. 2010, 76, 3898–3903.
    • (2010) Appl. Environ. Microbiol , vol.76 , pp. 3898-3903
    • Coyle, C.M.1    Cheng, J.Z.2    O’Connor, S.E.3    Panaccione, D.G.4
  • 54
    • 77954637647 scopus 로고    scopus 로고
    • Ergot alkaloid biosynthesis in Aspergillus fumigatus: Conversion of chanoclavine-I aldehyde to festuclavine by the festuclavine synthase FgaFS in the presence of the old yellow enzyme FgaOx3
    • Wallwey, C.; Matuschek, M.; Xie, X.L.; Li, S.M. Ergot alkaloid biosynthesis in Aspergillus fumigatus: Conversion of chanoclavine-I aldehyde to festuclavine by the festuclavine synthase FgaFS in the presence of the old yellow enzyme FgaOx3. Org. Biomol. Chem. 2010, 8, 3500–3508.
    • (2010) Org. Biomol. Chem , vol.8 , pp. 3500-3508
    • Wallwey, C.1    Matuschek, M.2    Xie, X.L.3    Li, S.M.4
  • 55
    • 80052963332 scopus 로고    scopus 로고
    • Formyl migration product of chanoclavine-I aldehyde in the presence of the old yellow enzyme FgaOx3 from Aspergillus fumigatus: A NMR structure elucidation
    • Xie, X.; Wallwey, C.; Matuschek, M.; Steinbach, K.; Li, S.M. Formyl migration product of chanoclavine-I aldehyde in the presence of the old yellow enzyme FgaOx3 from Aspergillus fumigatus: A NMR structure elucidation. Magn Reson. Chem. 2011, 49, 678–681.
    • (2011) Magn Reson. Chem , vol.49 , pp. 678-681
    • Xie, X.1    Wallwey, C.2    Matuschek, M.3    Steinbach, K.4    Li, S.M.5
  • 56
    • 77956636524 scopus 로고    scopus 로고
    • Controlling a structural branch point in ergot alkaloid biosynthesis
    • Cheng, J.Z.; Coyle, C.M.; Panaccione, D.G.; O’Connor, S.E. Controlling a structural branch point in ergot alkaloid biosynthesis. J. Am. Chem. Soc. 2010, 132, 12835–12837.
    • (2010) J. Am. Chem. Soc , vol.132 , pp. 12835-12837
    • Cheng, J.Z.1    Coyle, C.M.2    Panaccione, D.G.3    O’Connor, S.E.4
  • 57
    • 79956275333 scopus 로고    scopus 로고
    • New insights into ergot alkaloid biosynthesis in Claviceps purpurea: An agroclavine synthase EasG catalyses, via a non-enzymatic adduct with reduced glutathione, the conversion of chanoclavine-I aldehyde to agroclavine
    • Matuschek, M.; Wallwey, C.; Xie, X.; Li, S.M. New insights into ergot alkaloid biosynthesis in Claviceps purpurea: An agroclavine synthase EasG catalyses, via a non-enzymatic adduct with reduced glutathione, the conversion of chanoclavine-I aldehyde to agroclavine. Org. Biomol. Chem. 2011, 9, 4328–4335.
    • (2011) Org. Biomol. Chem , vol.9 , pp. 4328-4335
    • Matuschek, M.1    Wallwey, C.2    Xie, X.3    Li, S.M.4
  • 58
    • 70350523605 scopus 로고    scopus 로고
    • Ergot alkaloid biosynthesis in Aspergillus fumigatus: FgaAT catalyses the acetylation of fumigaclavine B
    • Liu, X.; Wang, L.; Steffan, N.; Yin, W.B.; Li, S.M. Ergot alkaloid biosynthesis in Aspergillus fumigatus: FgaAT catalyses the acetylation of fumigaclavine B. ChemBioChem 2009, 10, 2325–2328.
    • (2009) Chembiochem , vol.10 , pp. 2325-2328
    • Liu, X.1    Wang, L.2    Steffan, N.3    Yin, W.B.4    Li, S.M.5
  • 59
    • 30444438065 scopus 로고    scopus 로고
    • Reverse prenyltransferase in the biosynthesis of fumigaclavine C in Aspergillus fumigatus: Gene expression, purification and characterization of fumigaclavine C synthase FgaPT1
    • Unsöld, I.A.; Li, S.M. Reverse prenyltransferase in the biosynthesis of fumigaclavine C in Aspergillus fumigatus: Gene expression, purification and characterization of fumigaclavine C synthase FgaPT1. ChemBioChem 2006, 7, 158–164.
    • (2006) Chembiochem , vol.7 , pp. 158-164
    • Unsöld, I.A.1    Li, S.M.2
  • 60
    • 84861116464 scopus 로고    scopus 로고
    • Nonribosomal peptide synthetase genes pesL and pes1 are essential for fumigaclavine C production in Aspergillus fumigatus
    • O’Hanlon, K.A.; Gallagher, L.; Schrettl, M.; Jochl, C.; Kavanagh, K.; Larsen, T.O.; Doyle, S. Nonribosomal peptide synthetase genes pesL and pes1 are essential for fumigaclavine C production in Aspergillus fumigatus. Appl. Environ. Microbiol. 2012, 78, 3166–3176.
    • (2012) Appl. Environ. Microbiol , vol.78 , pp. 3166-3176
    • O’Hanlon, K.A.1    Gallagher, L.2    Schrettl, M.3    Jochl, C.4    Kavanagh, K.5    Larsen, T.O.6    Doyle, S.7
  • 61
    • 2042438359 scopus 로고
    • Microsomal oxygenases involved in ergoline alkaloid biosynthesis of various Claviceps strains
    • Maier, W.; Schumann, B.; Gröger, D. Microsomal oxygenases involved in ergoline alkaloid biosynthesis of various Claviceps strains. J. Basic Microbiol. 1988, 28, 83–93.
    • (1988) J. Basic Microbiol , vol.28 , pp. 83-93
    • Maier, W.1    Schumann, B.2    Gröger, D.3
  • 62
    • 2042479983 scopus 로고
    • Conversion of elymoclavine to paspalic acid by a particulate fraction from an ergotamine-producing strain of Claviceps sp
    • Kim, S.U.; Cho, Y.J.; Floss, H.G.; Anderson, J.A. Conversion of elymoclavine to paspalic acid by a particulate fraction from an ergotamine-producing strain of Claviceps sp. Planta Med. 1983, 48, 145–148.
    • (1983) Planta Med , vol.48 , pp. 145-148
    • Kim, S.U.1    Cho, Y.J.2    Floss, H.G.3    Anderson, J.A.4
  • 63
    • 33645781037 scopus 로고    scopus 로고
    • Identification of the cytochrome P450 monooxygenase that bridges the clavine and ergoline alkaloid pathways
    • Haarmann, T.; Ortel, I.; Tudzynski, P.; Keller, U. Identification of the cytochrome P450 monooxygenase that bridges the clavine and ergoline alkaloid pathways. ChemBioChem 2006, 7, 645–652.
    • (2006) Chembiochem , vol.7 , pp. 645-652
    • Haarmann, T.1    Ortel, I.2    Tudzynski, P.3    Keller, U.4
  • 64
    • 84907270592 scopus 로고    scopus 로고
    • Heterologous expression of lysergic acid and novel ergot alkaloids in Aspergillus fumigatus
    • Robinson, S.L.; Panaccione, D.G. Heterologous expression of lysergic acid and novel ergot alkaloids in Aspergillus fumigatus. Appl. Environ. Microbiol. 2014, doi:10.1128/AEM.02137-14.
    • (2014) Appl. Environ. Microbiol
    • Robinson, S.L.1    Panaccione, D.G.2
  • 65
    • 0030002729 scopus 로고    scopus 로고
    • D-Lysergyl peptide synthetase from the ergot fungus Claviceps purpurea
    • Riederer, B.; Han, M.; Keller, U. D-Lysergyl peptide synthetase from the ergot fungus Claviceps purpurea. J. Biol. Chem. 1996, 271, 27524–27530.
    • (1996) J. Biol. Chem , vol.271 , pp. 27524-27530
    • Riederer, B.1    Han, M.2    Keller, U.3
  • 66
    • 0031105296 scopus 로고    scopus 로고
    • Mechanism of alkaloid cyclopeptide synthesis in the ergot fungus Claviceps purpurea
    • Walzel, B.; Riederer, B.; Keller, U. Mechanism of alkaloid cyclopeptide synthesis in the ergot fungus Claviceps purpurea. Chem. Biol. 1997, 4, 223–230.
    • (1997) Chem. Biol , vol.4 , pp. 223-230
    • Walzel, B.1    Riederer, B.2    Keller, U.3
  • 67
    • 0346968186 scopus 로고    scopus 로고
    • Molecular cloning and analysis of the ergopeptine assembly system in the ergot fungus Claviceps purpurea
    • Correia, T.; Grammel, N.; Ortel, I.; Keller, U.; Tudzynski, P. Molecular cloning and analysis of the ergopeptine assembly system in the ergot fungus Claviceps purpurea. Chem. Biol. 2003, 10, 1281–1292.
    • (2003) Chem. Biol , vol.10 , pp. 1281-1292
    • Correia, T.1    Grammel, N.2    Ortel, I.3    Keller, U.4    Tudzynski, P.5
  • 68
    • 65449145993 scopus 로고    scopus 로고
    • Combinatorial assembly of simple and complex D-lysergic acid alkaloid peptide classes in the ergot fungus Claviceps purpurea
    • Ortel, I.; Keller, U. Combinatorial assembly of simple and complex D-lysergic acid alkaloid peptide classes in the ergot fungus Claviceps purpurea. J. Biol. Chem. 2009, 284, 6650–6660.
    • (2009) J. Biol. Chem , vol.284 , pp. 6650-6660
    • Ortel, I.1    Keller, U.2
  • 69
    • 84892680928 scopus 로고    scopus 로고
    • Cyclolization of D-lysergic acid alkaloid peptides
    • Havemann, J.; Vogel, D.; Loll, B.; Keller, U. Cyclolization of D-lysergic acid alkaloid peptides Chem. Biol. 2014, 21, 146–155.
    • (2014) Chem. Biol , vol.21 , pp. 146-155
    • Havemann, J.1    Vogel, D.2    Loll, B.3    Keller, U.4


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