Structure Revision of N -Mercapto-4-formylcarbostyril Produced by Pseudomonas fluorescens G308 to 2-(2-Hydroxyphenyl)thiazole-4-carbaldehyde [aeruginaldehyde]
Free accessResearch articleFirst published online June, 2014
Structure Revision of N -Mercapto-4-formylcarbostyril Produced by Pseudomonas fluorescens G308 to 2-(2-Hydroxyphenyl)thiazole-4-carbaldehyde [aeruginaldehyde]
An antibiotic substance isolated from Pseudomonas fluorescens strain G308 was earlier assigned the structure of N-mercapto-4-formylcarbostyril, but computational predictions of the 1H and 13C NMR magnetic shielding tensors show this structure to be incompatible with the published spectroscopic data. The same is true for six quinoline derivatives related to N-mercapto-4-formylcarbostyril by permutation of the O and S atoms. In contrast, 2-(2-hydroxyphenyl)thiazole-4-carbaldehyde [aeruginaldehyde], isolated from Pseudomonas protegens Pf-5, together with the reduced derivative aeruginol, displays spectroscopic data identical with those of the alleged carbostyril derivative. In addition, the published 1H and 13C NMR data are in agreement with those calculated for aeruginaldehyde. We propose that aeruginaldehyde and aeruginol originate from the non-ribosomal peptide synthetase enzymes involved in the siderophores enantio-pyochelin (or pyochelin) biosynthetic pathways.
FakhouriW., WalkerF., VoglerB., ArmbrusterW., BuchennauerH. (2001) Isolation and identification of N-mercapto-4-formylcarbostyril, an antibiotic produced by Pseudomonas fluorescens. Phytochemistry, 58, 1297–1303.
KulkarniM.V., KulkarniG.M., LinC-H, SunC-M. (2006) Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents. Current Medicinal Chemistry, 13, 2795–2818.
4.
HeebS., FletcherM.P., ChabraS.R., DiggleS.P., WilliamsP., CámaraM. (2011) Quinolones: from antibiotics to autoinducers. FEMS Microbiological Reviews, 35, 247–274.
5.
MorrisseyJ.P., CullinaneM., AbbasA., MarkG.L., O'GaraF. (2004) Biosynthesis and regulation of anti-fungal metabolites by Pseudomonads. Pseudomonas, 3, 637–670.
6.
BudzikiewicsH. (2004) Siderophores of the Pseudomonadaceae sensu stricto (fluorescent and non-fluorescent Pseudomonas spp.). Progress in the Chemistry of Organic Natural Products, 87, 81–237.
7.
FouchardS., Abdellaoui-MaâneZ., BoulangerA., LlopizP., NeunlistS. (2005) Influence of growth conditions on Pseudomonas fluorescens strains: A link between metabolic production and PLFA profile. FEMS Microbiology Letters, 251, 211–218.
8.
LeeJ.Y., MoonS.S., HwangB.K. (2003) Isolation and antifungal and antioomycete activities of aerugine produced by Pseudomonas fluorescens strain MM-B16. Applied and Environmental Microbiology, 69, 2023–2031.
9.
Polanski-CordovanoG., RomanoL., MarottaL.L.C., JacobS., HooJ.S., TartagliaE., AsokanD., KarS., DemainA.L. (2013) Nutritional studies on production of antibacterial activity by the zebra mussel antagonist, Pseudomonas fluorescens CL0145A. Journal of Microbiology and Biotechnology, 23, 656–660.
10.
OkubaraP.A., BonsallR.F. (2008) Accumulation of Pseudomonas-derived 2,4-diacetylphloroglucinol on wheat seedling roots is influenced by host cultivar. Biological Control, 46, 322–331.
11.
Abou El-HawaM.E., El-ShirbinyE.A., El-ZawahryY.A., El-SayedA., GalalA.M., Abd El-ShafiS. (2006) Extraction, purification and characterization of two antiphytiviral substance (s) produced by Zucchini yellow mosaic virus. International Journal of Agriculture & Biology, 8, 745–753.
12.
KaurR., MacleodJ., FoleyW., NayuduM. (2006) Gluconic acid: An antifungal agent produced by Pseudomonas species in biological control of take-all. Phytochemistry, 67, 595–604.
13.
GuihenE., GlennonJ.D., CullinaneM., O'GaraF. (2004) Rapid analysis of antimicrobial metabolites monoacetylphloroglucinol and 2,4-diacetylphloroglucinol using capillary zone electrophoresis. Electrophoresis, 25, 1536–1542.
14.
ChristophersenC., HammerichO. (2011) Does Pseudomonas fluorescens produce N-mercapto-4-formylcarbostyril?Natural Product Communications, 6, 921–922.
15.
BaroneG., Gomez-PalomaL., DucaD., SilvestriA., RiccioR., BifulcoG. (2002) Structure validation of natural products by quantum-mechanical GIAO calculations of 13C NMR chemical shifts. Chemistry – A European Journal, 8, 3233–3239.
16.
CiminoP., Gomez-PalomaL., DucaD., RiccioR., BifulcoG. (2004) Comparison of different theory models and basis sets in the calculation of 13C NMR chemical shifts of natural products. Magnetic Resonance in Chemistry, 42, S26–S33.
17.
BagnoA., RastrelliF., SaielliG. (2006) Toward the complete prediction of the 1H and 13C NMR spectra of complex organic molecules by DFT methods: application to natural substances. Chemistry – A European Journal, 12, 5514–5525.
18.
MossialosD., MeyerJ.M., BudzikiewiczH., WolffU., KoedamN., BaysseC., AnjaiahV., CornelisP. (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.
19.
MatthijsS., BaysseC., KoedamN., TehraniK.A., VerheydenL., BudzikiewiczH., SchäferM., HoorelbekeB., MeyerJ.M., De GreveH., CornelisP. (2004) The Pseudomonas siderophore quinolobactin is synthesized from xanthurenic acid, an intermediate of the kynurenine pathway. Molecular Biology, 52, 371–384.
20.
MatthijsS., TehraniK.A., LausG., JacksonR.W., CooperR.M., CornelisP. (2007) Thioquinolobactin, a Pseudomonas siderophore with antifungal and anti-Pythium activity. Environmental Microbiology, 9, 425–434.
21.
HöfleG., KunzeB. (2008) Biosynthesis of aurachins A-L in Stigmatella aurantiaca: A feeding study. Journal of Natural Products, 71, 1843–1849, and references cited therein.
22.
VialL., LépineF., MilotS., GroleauM.C., DekimpeV., WoodsD.E., DézielE. (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.
23.
DézielE., LépineF., MilotS., HeJ., MindrinosM.N., TompkinsR.G., RahmeL.G. (2004) Analysis of Pseudomonas aeruginosa 4-hydroxy-2-alkylquinolines (HAQs) reveals a role for 4-hydroxy-2-heptylquinoline in cell-to-cell communication. Proceedings of the National Academy of Sciences, 101, 1339–1344.
24.
OkazakiR., IshiiA., InamotoN. (1987) First isolation of a stable aliphatic thioaldehyde, tris(trimethylsilyl)ethanethial. Journal of the American Chemical Society, 109, 279–280.
25.
CorradiB.A., BogaC., ForlaniL., SgarabottoP. (1999) X-ray diffraction and self-condensation reaction of thionicotinamide S-oxide. Journal of Chemical Crystallography, 29, 115–119.
26.
LeeT.M., SiegelM.M., MortonG.O., GoodmanJ.J., TestaR., BordersD.B. (1995) Sulfinemycin, a new anthelmintic antibiotic: fermentation, isolation and structure determination. The Journal of Antibiotics, 48, 282–285.
27.
HassanK.A., JohnsonA., ShafferB.T., RenQ., KidarsaT.A., ElbourneL.D.H., HartneyS., DuboyR., GoebelN.C., ZabriskieT.M., PaulsenI.T., LoperJ.E. (2010) Inactivation of the GacA response regulator in Pseudomonas fluorescens Pf-5 has far-reaching transcriptomic consequences. Environmental Microbiology, 12, 899–915.
28.
ReimmannC., SerinoL., BeyelerM., HassD. (1998) Dihydroaeruginoic acid synthetase and pyochelin synthetase, products of the pchEF genes, are induced by extracellular pyochelin in Pseudomonas aeruginosa. Microbiology, 144, 3135–3148.
29.
SerinoL., ReimmannC., ViscaP., BeyelerM., ChiesaV.D., HassD. (1997) Biosynthesis of pyochelin and dihydroaeruginoic acid requires the iron-regulated pchDCBA operon in Pseudomonas aeruginosa. Journal of Bacteriology, 179, 248–257.
30.
BukovitsG.J., MohrN., BudzikiewiczH., KorthH., PulvererG. (1982) 2-Phenylthiazol-derivate aus Pseudomonas cepacia, Zeitschrift für Naturforschung, 37b, 877–880.
31.
CuppelsD.A., StipanovicR.D., StoesslA., StothersJ.B. (1987) The constitution and properties of a pyochelin-zinc complex. Canadian Journal of Chemistry, 65, 2126–2130.
32.
LeeJ., WuJ., DengY., WangJ., WangC., WangJ., ChangC., DongY., WilliamsP., ZhangL-H. (2013) A cell-cell communication signal integrates quorum sensing and stress response. Nature Chemical Biology, 9, 339–343.
33.
ZamriA., AbdallahM.A. (2000) An improved stereocontrolled synthesis of pyochelin, siderophore of Pseudomonas aeruginosa and Burkholderia capacia. Tetrahedron, 56, 249–256.
34.
RinehartK.L., StaleyA.L., WilsonS.R., AnkenbauerR.G., CoxC.D. (1995) Stereochemical assignment of the pyochelins. Journal of Organic Chemistry, 60, 2786–2791.
35.
MislinG.L., BurgerA., AbdallahA. (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.
36.
ByrneS., DurbinM., JonesA., MontgomeryC., QuevedoC., LiuG., SedenP., BatailleC., GuillermoA., DaviesS., WestwoodR., RussellA., WynneG., NaylorA. (2013) Preparation of phenylthiazolylmethylene substituted thiazolidinones as Pim kinase inhibitors.British UK Patent Application, GB 2497858 A 20130626.
37.
YangW., DostalL., RosazzaJ.P.N. (1993) Aeruginol [2-(2′-hydroxyphenyl)-4-hydromethylthiazole], a new secondary metabolite from Pseudomonas aeruginosa. Journal of Natural Products, 56, 1993–1994.
38.
AnkenbauerR.G., ToyokuniT., StaleyA., RinehartK.L.Jr., CoxC.D. (1988) Synthesis and biological activity of pyochelin, a siderophore of Pseudomonas aeruginosa. Journal of Bacteriology, 170, 5344–5351.
39.
NoëlS., GuillonL., SchalkI.J., MislinL.A. (2011) Synthesis of fluorescent probes based on the pyochelin siderophore scaffold. Organic Letters, 13, 844–847.
40.
WalshC.T., ChenH., KeatingT.A., HubbardB.K., LoseyH.C., LuoL., MarshallC.G., MillerD.A., PatelN.M. (2001) Tailoring enzymes that modify nonribosomal peptides during and after chain elongation on NRPS assembly lines. Current Opinion in Chemical Biology, 5, 525–534.
41.
GrossH., LoperJ.E. (2009) Genomics of secondary metabolite production by Pseudomonas spp. Natural Product Reports, 29, 1408–1446.
42.
PatelH.M., WalshC.T. (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.
43.
CarmiR., CarmeliS., LevyE., GoughF.J. (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.
44.
WuJ-E, O'ConnellY., ShieldsJ.A., CoxR.J., CrosbyJ., HothersallJ., SimpsonT.J., ThomasC.M., WillisC.L. (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.
45.
CoffmanT.J., CoxC.D., EdekerB.L., BritiganB.E. (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.
Please find the following supplemental material available below.
For Open Access articles published under a Creative Commons License, all supplemental material carries the same license as the article it is associated with.
For non-Open Access articles published, all supplemental material carries a non-exclusive license, and permission requests for re-use of supplemental material or any part of supplemental material shall be sent directly to the copyright owner as specified in the copyright notice associated with the article.
