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Volumn 11, Issue 10, 2016, Pages 2838-2846

Genetic and Molecular Basis of Botrydial Biosynthesis: Connecting Cytochrome P450-Encoding Genes to Biosynthetic Intermediates

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; POLYKETIDE; ALDEHYDE; BOTRYDIAL; BRIDGED BICYCLO COMPOUNDS;

EID: 84992221971     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/acschembio.6b00581     Document Type: Article
Times cited : (30)

References (37)
  • 2
    • 0033762670 scopus 로고    scopus 로고
    • Horizontal gene transfer and the evolution of secondary metabolite gene clusters in fungi: An hypothesis
    • Walton, J. D. (2000) Horizontal gene transfer and the evolution of secondary metabolite gene clusters in fungi: An hypothesis Fungal Genet. Biol. 30, 167-171 10.1006/fgbi.2000.1224
    • (2000) Fungal Genet. Biol. , vol.30 , pp. 167-171
    • Walton, J.D.1
  • 3
    • 44649170477 scopus 로고    scopus 로고
    • Evidence for horizontal transfer of a secondary metabolite gene cluster between fungi
    • Khaldi, N., Collemare, J., Lebrun, M. H., and Wolfe, K. H. (2008) Evidence for horizontal transfer of a secondary metabolite gene cluster between fungi Genome Biol. 9, R18 10.1186/gb-2008-9-1-r18
    • (2008) Genome Biol. , vol.9 , pp. R18
    • Khaldi, N.1    Collemare, J.2    Lebrun, M.H.3    Wolfe, K.H.4
  • 6
    • 77955428831 scopus 로고    scopus 로고
    • Secondary metabolism in fungi: Does chromosomal location matter?
    • Palmer, J. M. and Keller, N. P. (2010) Secondary metabolism in fungi: Does chromosomal location matter? Curr. Opin. Microbiol. 13, 431-436 10.1016/j.mib.2010.04.008
    • (2010) Curr. Opin. Microbiol. , vol.13 , pp. 431-436
    • Palmer, J.M.1    Keller, N.P.2
  • 9
    • 34547127883 scopus 로고    scopus 로고
    • Fungal terpene metabolites: Biosynthetic relationships and the control of the phytopathogenic fungus Botrytis cinerea
    • Collado, I. G., Sánchez, A. J. M., and Hanson, J. R. (2007) Fungal terpene metabolites: Biosynthetic relationships and the control of the phytopathogenic fungus Botrytis cinerea Nat. Prod. Rep. 24, 674-686 10.1039/b603085h
    • (2007) Nat. Prod. Rep. , vol.24 , pp. 674-686
    • Collado, I.G.1    Sánchez, A.J.M.2    Hanson, J.R.3
  • 10
    • 78650172778 scopus 로고    scopus 로고
    • Botrylactone: New interest in an old molecule, review of its absolute configuration and related compounds
    • Moraga, J., Pinedo, C., Duran-Patron, R., Collado, I. G., and Hernandez-Galán, R. (2011) Botrylactone: new interest in an old molecule, review of its absolute configuration and related compounds Tetrahedron 67, 417-420 10.1016/j.tet.2010.11.022
    • (2011) Tetrahedron , vol.67 , pp. 417-420
    • Moraga, J.1    Pinedo, C.2    Duran-Patron, R.3    Collado, I.G.4    Hernandez-Galán, R.5
  • 11
    • 58149464324 scopus 로고    scopus 로고
    • Chemistry and structural determination of botcinolides, botcinins, and botcinic acids
    • Shiina, I. and Fukui, H. (2009) Chemistry and structural determination of botcinolides, botcinins, and botcinic acids Chem. Commun. 4, 385-400 10.1039/B814375G
    • (2009) Chem. Commun. , vol.4 , pp. 385-400
    • Shiina, I.1    Fukui, H.2
  • 14
    • 10144257231 scopus 로고    scopus 로고
    • The phytotoxic activity of some metabolites of Botrytis cinerea
    • Rebordinos, L., Cantoral, J. M., Prieto, M. V., Hanson, J. R., and Collado, I. G. (1996) The phytotoxic activity of some metabolites of Botrytis cinerea Phytochemistry 42, 383-387 10.1016/0031-9422(95)00909-4
    • (1996) Phytochemistry , vol.42 , pp. 383-387
    • Rebordinos, L.1    Cantoral, J.M.2    Prieto, M.V.3    Hanson, J.R.4    Collado, I.G.5
  • 15
    • 0036097997 scopus 로고    scopus 로고
    • The putative role of botrydial and related metabolites in the infection mechanism of Botrytis cinerea
    • Colmenares, A. J., Aleu, J., Durán-Patrón, R., Collado, I. G., and Hernández-Galán, R. (2002) The putative role of botrydial and related metabolites in the infection mechanism of Botrytis cinerea J. Chem. Ecol. 28, 997-1005 10.1023/A:1015209817830
    • (2002) J. Chem. Ecol. , vol.28 , pp. 997-1005
    • Colmenares, A.J.1    Aleu, J.2    Durán-Patrón, R.3    Collado, I.G.4    Hernández-Galán, R.5
  • 17
    • 79960505724 scopus 로고    scopus 로고
    • The sesquiterpene botrydial produced by Botrytis cinerea induces the hypersensitive response on plant tissues and its action is modulated by salicylic acid and jasmonic acid signaling
    • Rossi, F. R., Gárriz, A., Marina, M., Romero, F. M., Gonzalez, M. E., Collado, I. G., and Pieckenstain, F. L. (2011) The sesquiterpene botrydial produced by Botrytis cinerea induces the hypersensitive response on plant tissues and its action is modulated by salicylic acid and jasmonic acid signaling Mol. Plant-Microbe Interact. 24 (8) 888-96 10.1094/MPMI-10-10-0248
    • (2011) Mol. Plant-Microbe Interact. , vol.24 , Issue.8 , pp. 888-896
    • Rossi, F.R.1    Gárriz, A.2    Marina, M.3    Romero, F.M.4    Gonzalez, M.E.5    Collado, I.G.6    Pieckenstain, F.L.7
  • 18
    • 0016147862 scopus 로고
    • Botrydial, ein Sesquiterpen-Antibiotikum aus der Nahrlosung des Pilzes Botrytis cinerea
    • Fehlhaber, H. W., Geipel, R., Mercker, H. J., Tschesche, R., Welmar, K., and Schönbeck, F. (1974) Botrydial, ein Sesquiterpen-Antibiotikum aus der Nahrlosung des Pilzes Botrytis cinerea Chem. Ber. 107, 1720-1730 10.1002/cber.19741070530
    • (1974) Chem. Ber. , vol.107 , pp. 1720-1730
    • Fehlhaber, H.W.1    Geipel, R.2    Mercker, H.J.3    Tschesche, R.4    Welmar, K.5    Schönbeck, F.6
  • 19
    • 84982071609 scopus 로고
    • Die Kristall- und Molekulstruktur yon Dihydrobotrydial
    • Lindner, H. J. and von Gross, B. (1974) Die Kristall- und Molekulstruktur yon Dihydrobotrydial Chem. Ber. 107, 3332-3336 10.1002/cber.19741071018
    • (1974) Chem. Ber. , vol.107 , pp. 3332-3336
    • Lindner, H.J.1    Von Gross, B.2
  • 20
    • 0002925635 scopus 로고
    • δ-Lactones. Cotton effect and conformation of the δ-lactone ring
    • Wolf, H. (1966) δ-Lactones. Cotton effect and conformation of the δ-lactone ring Tetrahedron Lett. 7, 5151-5156 10.1016/S0040-4039(01)89297-2
    • (1966) Tetrahedron Lett. , vol.7 , pp. 5151-5156
    • Wolf, H.1
  • 21
    • 37049108854 scopus 로고
    • Studies in terpenoid biosynthesis. Part 24. The formation of the carbon skeleton of the sesquiterpenoid dihydrobotrydial
    • Bradshaw, A. P. W., Hanson, J. R., and Nyfeler, R. (1981) Studies in terpenoid biosynthesis. Part 24. The formation of the carbon skeleton of the sesquiterpenoid dihydrobotrydial J. Chem. Soc., Perkin Trans. 1 1, 1469-1472 10.1039/p19810001469
    • (1981) J. Chem. Soc., Perkin Trans. 1 , vol.1 , pp. 1469-1472
    • Bradshaw, A.P.W.1    Hanson, J.R.2    Nyfeler, R.3
  • 22
    • 37049111166 scopus 로고
    • Studies in terpenoid biosynthesis. Part 25. The fate of the mevalonoid hydrogen atoms in the biosynthesis of the sesquiterpenoid, dihydrobotrydial
    • Bradshaw, A. P. W., Hanson, J. R., Nyfeler, R., and Sadler, I. H. (1982) Studies in terpenoid biosynthesis. Part 25. The fate of the mevalonoid hydrogen atoms in the biosynthesis of the sesquiterpenoid, dihydrobotrydial J. Chem. Soc., Perkin Trans. 1 1, 2187-2192 10.1039/p19820002187
    • (1982) J. Chem. Soc., Perkin Trans. 1 , vol.1 , pp. 2187-2192
    • Bradshaw, A.P.W.1    Hanson, J.R.2    Nyfeler, R.3    Sadler, I.H.4
  • 23
    • 0035799145 scopus 로고    scopus 로고
    • Some keymetabolic intermediates in the biosynthesis of botrydial and related compounds
    • Durán-Patrón, R., Colmenares, A. J., Hernández-Galán, R., and Collado, I. G. (2001) Some keymetabolic intermediates in the biosynthesis of botrydial and related compounds Tetrahedron 57, 1929-1933 10.1016/S0040-4020(01)00016-3
    • (2001) Tetrahedron , vol.57 , pp. 1929-1933
    • Durán-Patrón, R.1    Colmenares, A.J.2    Hernández-Galán, R.3    Collado, I.G.4
  • 24
    • 0001513075 scopus 로고
    • The biosynthesis of some sesquiterpenoids
    • Hanson, J. R. (1981) The biosynthesis of some sesquiterpenoids Pure Appl. Chem. 53, 1155-1162 10.1351/pac198153061155
    • (1981) Pure Appl. Chem. , vol.53 , pp. 1155-1162
    • Hanson, J.R.1
  • 26
    • 80052319576 scopus 로고    scopus 로고
    • Genomic analysis of the necrotrophic fungal pathogens Sclerotinia sclerotiorum and Botrytis cinerea
    • Amselem, J., Cuomo, C. A., and van Kan, J. A. et al. 2011, Genomic analysis of the necrotrophic fungal pathogens Sclerotinia sclerotiorum and Botrytis cinerea PLoS Genet. 7, e1002230 10.1371/journal.pgen.1002230
    • (2011) PLoS Genet. , vol.7 , pp. e1002230
    • Amselem, J.1    Cuomo, C.A.2    Van Kan, J.A.3
  • 27
    • 19544391219 scopus 로고    scopus 로고
    • Functional analysis of the cytochrome P450 monooxygenase gene bcbot1 of Botrytis cinerea indicates that botrydial is a strain-specific virulence factor
    • Siewers, V., Viaud, M., Jimenez-Teja, D., Collado, I. G., Gronover, C. S., Pradier, J.-M.-M., Tudzynski, B., and Tudzynski, P. (2005) Functional analysis of the cytochrome P450 monooxygenase gene bcbot1 of Botrytis cinerea indicates that botrydial is a strain-specific virulence factor Mol. Plant-Microbe Interact. 18, 602-612 10.1094/MPMI-18-0602
    • (2005) Mol. Plant-Microbe Interact. , vol.18 , pp. 602-612
    • Siewers, V.1    Viaud, M.2    Jimenez-Teja, D.3    Collado, I.G.4    Gronover, C.S.5    Pradier, J.-M.-M.6    Tudzynski, B.7    Tudzynski, P.8
  • 29
    • 84355163053 scopus 로고    scopus 로고
    • Cytochrome P450 monooxygenases: An update on perspectives for synthetic application
    • Urlacher, V. B. and Girhard, M. (2012) Cytochrome P450 monooxygenases: an update on perspectives for synthetic application Trends Biotechnol. 30, 26-36 10.1016/j.tibtech.2011.06.012
    • (2012) Trends Biotechnol. , vol.30 , pp. 26-36
    • Urlacher, V.B.1    Girhard, M.2
  • 30
    • 58149142845 scopus 로고    scopus 로고
    • Prediction of a New Pathway to Presilphiperfolanol
    • Wang, S. C. and Tantillo, D. J. (2008) Prediction of a New Pathway to Presilphiperfolanol Org. Lett. 10, 4827-4830 10.1021/ol801898v
    • (2008) Org. Lett. , vol.10 , pp. 4827-4830
    • Wang, S.C.1    Tantillo, D.J.2
  • 31
    • 67650551478 scopus 로고    scopus 로고
    • Biosynthesis of the Sesquiterpene Botrydial in Botrytis cinerea. Mechanism and Stereochemistry of the Enzymatic Formation of Presilphiperfolan-8β-ol
    • Wang, C.-M., Hopson, R., Lin, X., and Cane, D. E. (2009) Biosynthesis of the Sesquiterpene Botrydial in Botrytis cinerea. Mechanism and Stereochemistry of the Enzymatic Formation of Presilphiperfolan-8β-ol J. Am. Chem. Soc. 131, 8360-8361 10.1021/ja9021649
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 8360-8361
    • Wang, C.-M.1    Hopson, R.2    Lin, X.3    Cane, D.E.4
  • 32
    • 79959933873 scopus 로고    scopus 로고
    • The Botrytis cinerea phytotoxin botcinic acid requires two polyketide synthases for production and has a redundant role in virulence with botrydial
    • Dalmais, B., Schumacher, J., Moraga, J., LE Pêcheur, P., Tudzynski, B., Collado, I. G., and Viaud, M. (2011) The Botrytis cinerea phytotoxin botcinic acid requires two polyketide synthases for production and has a redundant role in virulence with botrydial Mol. Plant Pathol. 12, 564-79 10.1111/j.1364-3703.2010.00692.x
    • (2011) Mol. Plant Pathol. , vol.12 , pp. 564-579
    • Dalmais, B.1    Schumacher, J.2    Moraga, J.3    Pêcheur P, L.E.4    Tudzynski, B.5    Collado, I.G.6    Viaud, M.7
  • 33
    • 0015500466 scopus 로고
    • Studies on the biosynthetic conversion of cholesterol into pregnenolone. Side chain cleavage of a t-butyl analog of 20α-hydroxycholesterol, (20R)-20-t-butyl-5-pregnene-3β, 20-diol, a compound completely substituted at C-22
    • Luttrell, B., Hochberg, R. B., Dixon, W. R., Mcdonald, P. D., and Lieberman, S. (1972) Studies on the biosynthetic conversion of cholesterol into pregnenolone. Side chain cleavage of a t-butyl analog of 20α-hydroxycholesterol, (20R)-20-t-butyl-5-pregnene-3β, 20-diol, a compound completely substituted at C-22 J. Biol. Chem. 247 (5) 1462-1472
    • (1972) J. Biol. Chem. , vol.247 , Issue.5 , pp. 1462-1472
    • Luttrell, B.1    Hochberg, R.B.2    Dixon, W.R.3    McDonald, P.D.4    Lieberman, S.5
  • 34
    • 0032030085 scopus 로고    scopus 로고
    • Detoxification of α-tomatine by Botrytis cinerea. Physiol
    • Quidde, T., Osbourn, A. E., and Tudzynski, P. (1998) Detoxification of α-tomatine by Botrytis cinerea. Physiol Physiol. Mol. Plant Pathol. 52, 151-165 10.1006/pmpp.1998.0142
    • (1998) Physiol. Mol. Plant Pathol. , vol.52 , pp. 151-165
    • Quidde, T.1    Osbourn, A.E.2    Tudzynski, P.3
  • 35
    • 4644220750 scopus 로고    scopus 로고
    • Double-joint PCR: A PCR-based molecular tool for gene manipulations in filamentous fungi
    • Yu, J. H., Hamari, Z., Han, K. H., Seo, J. A., Reyes-Domínguez, Y., and Scazzocchio, C. (2004) Double-joint PCR: a PCR-based molecular tool for gene manipulations in filamentous fungi Fungal Genet. Biol. 41 (11) 973-81 10.1016/j.fgb.2004.08.001
    • (2004) Fungal Genet. Biol. , vol.41 , Issue.11 , pp. 973-981
    • Yu, J.H.1    Hamari, Z.2    Han, K.H.3    Seo, J.A.4    Reyes-Domínguez, Y.5    Scazzocchio, C.6
  • 36
    • 84868131357 scopus 로고    scopus 로고
    • The homeobox BcHOX8 gene in Botrytis cinerea regulates vegetative growth and morphology
    • Antal, Z., Rascle, C., Cimerman, A., Viaud, M., Billon-Grand, G., Choquer, M., and Bruel, C. (2012) The homeobox BcHOX8 gene in Botrytis cinerea regulates vegetative growth and morphology PLoS One 7 (10) e48134 10.1371/journal.pone.0048134
    • (2012) PLoS One , vol.7 , Issue.10 , pp. e48134
    • Antal, Z.1    Rascle, C.2    Cimerman, A.3    Viaud, M.4    Billon-Grand, G.5    Choquer, M.6    Bruel, C.7
  • 37
    • 84874956484 scopus 로고    scopus 로고
    • Screening of a Botrytis cinerea one-hybrid library reveals a Cys2His2 transcription factor involved in the regulation of secondary metabolism gene clusters
    • Simon, A., Dalmais, B., Morgant, G., and Viaud, M. (2013) Screening of a Botrytis cinerea one-hybrid library reveals a Cys2His2 transcription factor involved in the regulation of secondary metabolism gene clusters Fungal Genet. Biol. 52, 9-19 10.1016/j.fgb.2013.01.006
    • (2013) Fungal Genet. Biol. , vol.52 , pp. 9-19
    • Simon, A.1    Dalmais, B.2    Morgant, G.3    Viaud, M.4


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