메뉴 건너뛰기




Volumn 9, Issue 6, 2014, Pages 789-794

Structure revision of N-mercapto-4-formylcarbostyril produced by Pseudomonas fluorescens G308 to 2-(2-hydroxyphenyl)thiazole-4-carbaldehyde [aeruginaldehyde]

Author keywords

(Enantio)pyochelin; Aeruginaldehyde; Aeruginol; IQS; N mercapto 4 formylcarbostyril; Pseudomonas fluorescens; Pseudomonas protegens

Indexed keywords

2 (2 HYDROXYPHENYL)THIAZOLE 4 CARBALDEHYDE [AERUGINALDEHYDE]; CARBOSTYRIL DERIVATIVE; N MERCAPTO 4 FORMYLCARBOSTYRIL; QUINOLINE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84903644534     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1400900615     Document Type: Article
Times cited : (31)

References (46)
  • 1
    • 0035861340 scopus 로고    scopus 로고
    • Isolation and identification of N-mercapto-4-formylcarbostyril, an antibiotic produced by Pseudomonas fluorescens
    • DOI 10.1016/S0031-9422(01)00344-2, PII S0031942201003442
    • Fakhouri W, Walker F, Vogler B, Armbruster W, Buchennauer H. (2001) Isolation and identification of N-mercapto-4-formylcarbostyril, an antibiotic produced by Pseudomonas fluorescens. Phytochemistry, 58, 1297-1303. (Pubitemid 34019503)
    • (2001) Phytochemistry , vol.58 , Issue.8 , pp. 1297-1303
    • Fakhouri, W.1    Walker, F.2    Vogler, B.3    Armbruster, W.4    Buchenauer, H.5
  • 2
    • 0142216387 scopus 로고    scopus 로고
    • Quinoline, quinazoline and acridone alkaloids
    • Michael JP. (2003) Quinoline, quinazoline and acridone alkaloids. Natural Product Reports, 20, 476-493.
    • (2003) Natural Product Reports , vol.20 , pp. 476-493
    • Michael, J.P.1
  • 3
    • 33749426542 scopus 로고    scopus 로고
    • Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents
    • DOI 10.2174/092986706778521968
    • Kulkarni MV, Kulkarni GM, Lin C-H, Sun C-M. (2006) Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents. Current Medicinal Chemistry, 13, 2795-2818. (Pubitemid 44509726)
    • (2006) Current Medicinal Chemistry , vol.13 , Issue.23 , pp. 2795-2818
    • Kulkarni, M.V.1    Kulkarni, G.M.2    Lin, C.-H.3    Sun, C.-M.4
  • 5
    • 15944393796 scopus 로고    scopus 로고
    • Biosynthesis and regulation of anti-fungal metabolites by Pseudomonads
    • Morrissey JP, Cullinane M, Abbas A, Mark GL, O'Gara F. (2004) Biosynthesis and regulation of anti-fungal metabolites by Pseudomonads. Pseudomonas, 3, 637-670.
    • (2004) Pseudomonas , vol.3 , pp. 637-670
    • Morrissey, J.P.1    Cullinane, M.2    Abbas, A.3    Mark, G.L.4    O'Gara, F.5
  • 6
    • 2342530935 scopus 로고    scopus 로고
    • Siderophores of the Pseudomonadaceae sensu stricto (fluorescent and non-fluorescent Pseudomonas spp.)
    • Budzikiewics H. (2004) Siderophores of the Pseudomonadaceae sensu stricto (fluorescent and non-fluorescent Pseudomonas spp.). Progress in the Chemistry of Organic Natural Products, 87, 81-237.
    • (2004) Progress in the Chemistry of Organic Natural Products , vol.87 , pp. 81-237
    • Budzikiewics, H.1
  • 7
    • 25644446964 scopus 로고    scopus 로고
    • Influence of growth conditions on Pseudomonas fluorescens strains: A link between metabolite production and the PLFA profile
    • DOI 10.1016/j.femsle.2005.08.003, PII S0378109705005501
    • Fouchard S, Abdellaoui-Maâne Z, Boulanger A, Llopiz P, Neunlist S. (2005) Influence of growth conditions on Pseudomonas fluorescens strains: A link between metabolic production and PLFA profile. FEMS Microbiology Letters, 251, 211-218. (Pubitemid 41383871)
    • (2005) FEMS Microbiology Letters , vol.251 , Issue.2 , pp. 211-218
    • Fouchard, S.1    Abdellaoui-Maane, Z.2    Boulanger, A.3    Llopiz, P.4    Neunlist, S.5
  • 8
    • 0242416601 scopus 로고    scopus 로고
    • Isolation and antifungal and antioomycete activities of aerugine produced by Pseudomonas fluorescens strain MM-B16
    • DOI 10.1128/AEM.69.4.2023-2031.2003
    • Lee JY, Moon SS, Hwang BK. (2003) Isolation and antifungal and antioomycete activities of aerugine produced by Pseudomonas fluorescens strain MM-B16. Applied and Environmental Microbiology, 69, 2023-2031. (Pubitemid 36443615)
    • (2003) Applied and Environmental Microbiology , vol.69 , Issue.4 , pp. 2023-2031
    • Lee, J.Y.1    Moon, S.S.2    Hwang, B.K.3
  • 10
    • 48449097928 scopus 로고    scopus 로고
    • Accumulation of Pseudomonas-derived 2,4-diacetylphloroglucinol on wheat seedling roots is influenced by host cultivar
    • Okubara PA, Bonsall RF. (2008) Accumulation of Pseudomonas-derived 2,4-diacetylphloroglucinol on wheat seedling roots is influenced by host cultivar. Biological Control, 46, 322-331.
    • (2008) Biological Control , vol.46 , pp. 322-331
    • Okubara, P.A.1    Bonsall, R.F.2
  • 12
    • 32644468762 scopus 로고    scopus 로고
    • Gluconic acid: An antifungal agent produced by Pseudomonas species in biological control of take-all
    • DOI 10.1016/j.phytochem.2005.12.011, PII S0031942205007077
    • Kaur R, Macleod J, Foley W, Nayudu M. (2006) Gluconic acid: An antifungal agent produced by Pseudomonas species in biological control of take-all. Phytochemistry, 67, 595-604. (Pubitemid 43247617)
    • (2006) Phytochemistry , vol.67 , Issue.6 , pp. 595-604
    • Kaur, R.1    Macleod, J.2    Foley, W.3    Nayudu, M.4
  • 13
    • 3042854222 scopus 로고    scopus 로고
    • Rapid analysis of antimicrobial metabolites monoacetylphloroglucinol and 2,4-diacetylphlorogucinol using capillary zone electrophoresis
    • Guihen E, Glennon JD, Cullinane M, O'Gara F. (2004) Rapid analysis of antimicrobial metabolites monoacetylphloroglucinol and 2,4- diacetylphloroglucinol using capillary zone electrophoresis. Electrophoresis, 25, 1536-1542. (Pubitemid 38885815)
    • (2004) Electrophoresis , vol.25 , Issue.10-11 , pp. 1536-1542
    • Guihen, E.1    Glennon, J.D.2    Cullinane, M.3    O'Gara, F.4
  • 14
    • 79959249312 scopus 로고    scopus 로고
    • Does Pseudomonas fluorescens produce N-mercapto-4-formylcarbostyril?
    • Christophersen C, Hammerich O. (2011) Does Pseudomonas fluorescens produce N-mercapto-4-formylcarbostyril? Natural Product Communications, 6, 921-922.
    • (2011) Natural Product Communications , vol.6 , pp. 921-922
    • Christophersen, C.1    Hammerich, O.2
  • 17
    • 33746274916 scopus 로고    scopus 로고
    • 13C NMR spectra of complex organic molecules by DFT methods: Application to natural substances
    • 13C NMR spectra of complex organic molecules by DFT methods: application to natural substances. Chemistry - A European Journal, 12, 5514-5525.
    • (2006) Chemistry - A European Journal , vol.12 , pp. 5514-5525
    • Bagno, A.1    Rastrelli, F.2    Saielli, G.3
  • 18
    • 0033952910 scopus 로고    scopus 로고
    • Quinolobactin, a new siderophore of Pseudomonas fluorescens ATCC 17400, the production of which is repressed by the cognate pyoverdine
    • DOI 10.1128/AEM.66.2.487-492.2000
    • Mossialos D, Meyer JM, Budzikiewicz H, Wolff U, Koedam N, Baysse C, Anjaiah V, Cornelis P. (2000) Quinolobactin, a new siderophore of Pseudomonas fluorescens ATCC 17400, the production of which is repressed by the cognate pyoverdine. Applied and Environmental Microbiology, 66, 487-492. (Pubitemid 30082731)
    • (2000) Applied and Environmental Microbiology , vol.66 , Issue.2 , pp. 487-492
    • Mossialos, D.1    Meyer, J.-M.2    Budzikiewicz, H.3    Wolff, U.4    Koedam, N.5    Baysse, C.6    Anjaiah, V.7    Cornelis, P.8
  • 20
    • 33846062870 scopus 로고    scopus 로고
    • Thioquinolobactin, a Pseudomonas siderophore with antifungal and anti-Pythium activity
    • DOI 10.1111/j.1462-2920.2006.01154.x
    • Matthijs S, Tehrani KA, Laus G, Jackson RW, Cooper RM, Cornelis P. (2007) Thioquinolobactin, a Pseudomonas siderophore with antifungal and anti-Pythium activity. Environmental Microbiology, 9, 425-434. (Pubitemid 46072128)
    • (2007) Environmental Microbiology , vol.9 , Issue.2 , pp. 425-434
    • Matthijs, S.1    Tehrani, K.A.2    Laus, G.3    Jackson, R.W.4    Cooper, R.M.5    Cornelis, P.6
  • 21
    • 58149149905 scopus 로고    scopus 로고
    • Biosynthesis of aurachins A-L in Stigmatella aurantiaca: A feeding study
    • and references cited therein
    • Höfle G, Kunze B. (2008) Biosynthesis of aurachins A-L in Stigmatella aurantiaca: A feeding study. Journal of Natural Products, 71, 1843-1849, and references cited therein.
    • (2008) Journal of Natural Products , vol.71 , pp. 1843-1849
    • Höfle, G.1    Kunze, B.2
  • 22
    • 48149111001 scopus 로고    scopus 로고
    • Burkholderia pseudomallei, B. thailandensis, and B. ambifaria produce 4-hydroxy-2-alkylquinoline analogues with a methyl group at the 2 position that is required for quorum-sensing regulation
    • and references cited therein
    • Vial L, Lépine F, Milot S, Groleau MC, Dekimpe V, Woods DE, Déziel E. (2008) Burkholderia pseudomallei, B. thailandensis, and B. ambifaria produce 4-hydroxy-2-alkylquinoline analogues with a methyl group at the 2 position that is required for quorum-sensing regulation. Journal of Bacteriology, 190, 5339-5352, and references cited therein.
    • (2008) Journal of Bacteriology , vol.190 , pp. 5339-5352
    • Vial, L.1    Lépine, F.2    Milot, S.3    Groleau, M.C.4    Dekimpe, V.5    Woods, D.E.6    Déziel, E.7
  • 24
    • 33845281397 scopus 로고
    • First isolation of a stable aliphatic thioaldehyde, tris(trimethylsilyl) ethanethial
    • Okazaki R, Ishii A, Inamoto N. (1987) First isolation of a stable aliphatic thioaldehyde, tris(trimethylsilyl)ethanethial. Journal of the American Chemical Society, 109, 279-280.
    • (1987) Journal of the American Chemical Society , vol.109 , pp. 279-280
    • Okazaki, R.1    Ishii, A.2    Inamoto, N.3
  • 25
    • 0032623349 scopus 로고    scopus 로고
    • X-ray diffraction and self condensation reaction of thionicotinamide S-oxide
    • Corradi BA, Boga C, Forlani L, Sgarabotto P. (1999) X-ray diffraction and self-condensation reaction of thionicotinamide S-oxide. Journal of Chemical Crystallography, 29, 115-119. (Pubitemid 129325418)
    • (1999) Journal of Chemical Crystallography , vol.29 , Issue.1 , pp. 115-119
    • Corradi, A.B.1    Boga, C.2    Forlani, L.3    Sgarabotto, P.4
  • 28
    • 0031736408 scopus 로고    scopus 로고
    • Dihydroaeruginoic acid synthetase and pyochelin synthetase, products of the pchEF genes, are induced by extracellular pyochelin in Pseudomonas aeruginosa
    • Reimmann C, Serino L, Beyeler M, Hass D. (1998) Dihydroaeruginoic acid synthetase and pyochelin synthetase, products of the pchEF genes, are induced by extracellular pyochelin in Pseudomonas aeruginosa. Microbiology, 144, 3135-3148. (Pubitemid 28515593)
    • (1998) Microbiology , vol.144 , Issue.11 , pp. 3135-3148
    • Reimmann, C.1    Serino, L.2    Beyeler, M.3    Haas, D.4
  • 29
    • 0031020825 scopus 로고    scopus 로고
    • Biosynthesis of pyochelin and dihydroaeruginoic acid requires the iron- regulated pchDCBA operon in Pseudomonas aeruginosa
    • Serino L, Reimmann C, Visca P, Beyeler M, Chiesa VD, Hass D. (1997) Biosynthesis of pyochelin and dihydroaeruginoic acid requires the ironregulated pchDCBA operon in Pseudomonas aeruginosa. Journal of Bacteriology, 179, 248-257. (Pubitemid 26428488)
    • (1997) Journal of Bacteriology , vol.179 , Issue.1 , pp. 248-257
    • Serino, L.1    Reimmann, C.2    Visca, P.3    Beyeler, M.4    Chiesa, V.D.5    Haas, D.6
  • 33
    • 0034614591 scopus 로고    scopus 로고
    • An improved stereocontrolled synthesis of pyochelin, siderophore of Pseudomonas aeruginosa and Burkholderia cepacia
    • PII S0040402099009461
    • Zamri A, Abdallah MA. (2000) An improved stereocontrolled synthesis of pyochelin, siderophore of Pseudomonas aeruginosa and Burkholderia capacia. Tetrahedron, 56, 249-256. (Pubitemid 30048053)
    • (2000) Tetrahedron , vol.56 , Issue.2 , pp. 249-256
    • Zamri, A.1    Abdallah, M.A.2
  • 35
    • 9644289519 scopus 로고    scopus 로고
    • Synthesis of new thiazole analogues of pyochelin, a siderophore of Pseudomonas aeruginosa and Burkholderia cepacia. A new conversion of thiazolines into thiazoles
    • DOI 10.1016/j.tet.2004.10.030, PII S0040402004017193
    • Mislin GL, Burger A, Abdallah A. (2004) Synthesis of new thiazole analogues of pyochelin, a siderophore of Pseudomonas aeruginosa and Burkholderia cepacia. A new conversion of thiazolines into thiazoles. Tetrahedron, 60, 12139-12145. (Pubitemid 39572647)
    • (2004) Tetrahedron , vol.60 , Issue.52 , pp. 12139-12145
    • Mislin, G.L.1    Burger, A.2    Abdallah, M.A.3
  • 37
    • 0027525635 scopus 로고
    • Aeruginol [2-(2'-hydroxyphenyl)-4-hydroxymethylthiazole], a new secondary metabolite from Pseudomonas aeruginosa
    • DOI 10.1021/np50101a021
    • Yang W, Dostal L, Rosazza JPN. (1993) Aeruginol [2-(2′- hydroxyphenyl)-4-hydromethylthiazole], a new secondary metabolite from Pseudomonas aeruginosa. Journal of Natural Products, 56, 1993-1994. (Pubitemid 23348577)
    • (1993) Journal of Natural Products (Lloydia) , vol.56 , Issue.11 , pp. 1993-1994
    • Yang, W.1    Dostal, L.2    Rosazza, J.P.N.3
  • 38
    • 0023727902 scopus 로고
    • Synthesis and biological activity of pyochelin, a siderophore of Pseudomonas aeruginosa
    • Ankenbauer RG, Toyokuni T, Staley A, Rinehart, Jr KL, Cox CD. (1988) Synthesis and biological activity of pyochelin, a siderophore of Pseudomonas aeruginosa. Journal of Bacteriology, 170, 5344-5351. (Pubitemid 18259469)
    • (1988) Journal of Bacteriology , vol.170 , Issue.11 , pp. 5344-5351
    • Ankenbauer, R.G.1    Toyokuni, T.2    Staley, A.3    Rinehart Jr., K.L.4    Cox, C.D.5
  • 39
    • 79952153983 scopus 로고    scopus 로고
    • Synthesis of fluorescent probes based on the pyochelin siderophore scaffold
    • Noël S, Guillon L, Schalk IJ, Mislin LA. (2011) Synthesis of fluorescent probes based on the pyochelin siderophore scaffold. Organic Letters, 13, 844-847.
    • (2011) Organic Letters , vol.13 , pp. 844-847
    • Noël, S.1    Guillon, L.2    Schalk, I.J.3    Mislin, L.A.4
  • 41
    • 70350736705 scopus 로고    scopus 로고
    • Genomics of secondary metabolite production by Pseudomonas spp
    • Gross H, Loper JE. (2009) Genomics of secondary metabolite production by Pseudomonas spp. Natural Product Reports, 29, 1408-1446.
    • (2009) Natural Product Reports , vol.29 , pp. 1408-1446
    • Gross, H.1    Loper, J.E.2
  • 42
    • 0035979338 scopus 로고    scopus 로고
    • In vitro reconstitution of the Pseudomonas aeruginosa nonribosomal peptide synthesis of pyochelin: Characterization of backbone tailoring thiazoline reductase and N-methyltransferase activities
    • and references cited herein
    • Patel HM, Walsh CT. (2001) In vitro reconstitution of the Pseudomonas aeruginosa nonribosomal peptide synthesis of pyochelin: Characterization of backbone tailoring thiazoline reductase and N-methyltransferase activities. Biochemistry, 40, 9023-9031 and references cited herein.
    • (2001) Biochemistry , vol.40 , pp. 9023-9031
    • Patel, H.M.1    Walsh, C.T.2
  • 43
    • 0028029847 scopus 로고
    • (+)-(S)-dihydroaeruginoic acid, an inhibitor of Septoria tritici and other phytopathogenic fungi and bacteria, produced by Pseudomonas fluorescens
    • DOI 10.1021/np50111a002
    • Carmi R, Carmeli S, Levy E, Gough FJ. (1994) (+)-(S)-Dihydroaeruginoic acid, an inhibitor of Septoria tritici and other phytopathogenic fungi and bacteria, produced by Pseudomonas fluorescens. Journal of Natural Products, 57, 1200-1205. (Pubitemid 24333028)
    • (1994) Journal of Natural Products , vol.57 , Issue.9 , pp. 1200-1205
    • Carmi, R.1    Carmeli, S.2    Levy, E.3    Gough, F.J.4
  • 44
    • 49249099787 scopus 로고    scopus 로고
    • Accumulation of mupirocin H and mupiric acid during in vivo mutational analysis of the mupirocin gene cluster reveals labile points in the biosynthetic pathway: The "leaky hosepipe" mechanism
    • Wu J-E, O'Connell Y, Shields JA, Cox RJ, Crosby J, Hothersall J, Simpson TJ, Thomas CM, Willis CL. (2008) Accumulation of mupirocin H and mupiric acid during in vivo mutational analysis of the mupirocin gene cluster reveals labile points in the biosynthetic pathway: the "leaky hosepipe" mechanism. ChemBioChem, 9, 1500-1508.
    • (2008) ChemBioChem , vol.9 , pp. 1500-1508
    • Wu, J.-E.1    O'Connell, Y.2    Shields, J.A.3    Cox, R.J.4    Crosby, J.5    Hothersall, J.6    Simpson, T.J.7    Thomas, C.M.8    Willis, C.L.9
  • 45
    • 0025165769 scopus 로고
    • Possible role of bacterial siderophores in inflammation. Iron bound to the Pseudonomas siderophore pyochelin can function as a hydroxyl radical catalyst
    • Coffman TJ, Cox CD, Edeker BL, Britigan BE. (1990) Possible role of bacterial siderophores in inflammation: iron bound to the Pseudomonas siderophore pyochelin can function as a hydroxyl radical catalyst. Journal of Clinical Investigations, 86, 1030-1037. (Pubitemid 20370405)
    • (1990) Journal of Clinical Investigation , vol.86 , Issue.4 , pp. 1030-1037
    • Coffman, T.J.1    Cox, C.D.2    Edeker, B.L.3    Britigan, B.E.4
  • 46
    • 84903578496 scopus 로고    scopus 로고
    • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery, Jr. JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann, RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski, JW, Martin RL, Morokuma K, Zakrzewski, VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. (2010), Gaussian, Inc., Wallingford CT
    • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery, Jr. JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann, RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski, JW, Martin RL, Morokuma K, Zakrzewski, VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. (2010), Gaussian, Inc., Wallingford CT.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.