Pseudochelin A, a siderophore of Pseudoalteromonas piscicida S2040

Eva C. Sonnenschein; Marc Stierhof; Stephan Goralczyk; Floriane M. Vabre; Leonie Pellissier; Kine Østnes Hanssen; Mercedes de la Cruz; Caridad Díaz; Peter de Witte; Daniëlle Copmans; Jeanette Hammer Andersen; Espen Hansen; Venke Kristoffersen; José R. Tormo; Rainer Ebel; Bruce F. Milne; Hai Deng; Lone Gram; Marcel Jaspars; Jioji N. Tabudravu

doi:10.1016/j.tet.2017.03.051

Pseudochelin A, a siderophore of Pseudoalteromonas piscicida S2040

Eva C. Sonnenschein, Marc Stierhof, Stephan Goralczyk, Floriane M. Vabre, Leonie Pellissier, Kine Østnes Hanssen, Mercedes de la Cruz, Caridad Díaz, Peter de Witte, Daniëlle Copmans, Jeanette Hammer Andersen, Espen Hansen, Venke Kristoffersen, José R. Tormo, Rainer Ebel, Bruce F. Milne, Hai Deng, Lone Gram, Marcel Jaspars, Jioji N. Tabudravu^*

^*Corresponding author for this work

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Abstract

A new siderophore containing a 4,5-dihydroimidazole moiety was isolated from Pseudoalteromonas piscicida S2040 together with myxochelins A and B, alteramide A and its cycloaddition product, and bromo- and dibromoalterochromides. The structure of pseudochelin A was established by spectroscopic techniques including 2D NMR and MS/MS fragmentation data. In bioassays selected fractions of the crude extract of S2040 inhibited the opportunistic pathogen Pseudomonas aeruginosa. Pseudochelin A displayed siderophore activity in the chrome azurol S assay at concentrations higher than 50 μM, and showed weak activity against the fungus Aspergillus fumigatus, but did not display antibacterial, anti-inflammatory or anticonvulsant activity.

Original language	English
Pages (from-to)	2633-2637
Number of pages	5
Journal	Tetrahedron
Volume	73
Issue number	18
Early online date	21 Mar 2017
DOIs	https://doi.org/10.1016/j.tet.2017.03.051
Publication status	Published - 4 May 2017

Keywords

LCMS
NMR
Pseudoalteromonas
Pseudochelin A
Siderophore

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Sonnenschein, E. C., Stierhof, M., Goralczyk, S., Vabre, F. M., Pellissier, L., Hanssen, K. Ø., de la Cruz, M., Díaz, C., de Witte, P., Copmans, D., Andersen, J. H., Hansen, E., Kristoffersen, V., Tormo, J. R., Ebel, R., Milne, B. F., Deng, H., Gram, L., Jaspars, M., & Tabudravu, J. N. (2017). Pseudochelin A, a siderophore of Pseudoalteromonas piscicida S2040. Tetrahedron, 73(18), 2633-2637. https://doi.org/10.1016/j.tet.2017.03.051

Pseudochelin A, a siderophore of Pseudoalteromonas piscicida S2040. / Sonnenschein, Eva C.; Stierhof, Marc; Goralczyk, Stephan; Vabre, Floriane M.; Pellissier, Leonie; Hanssen, Kine Østnes; de la Cruz, Mercedes; Díaz, Caridad; de Witte, Peter; Copmans, Daniëlle; Andersen, Jeanette Hammer; Hansen, Espen; Kristoffersen, Venke; Tormo, José R.; Ebel, Rainer; Milne, Bruce F.; Deng, Hai; Gram, Lone; Jaspars, Marcel ; Tabudravu, Jioji N.

In: Tetrahedron, Vol. 73, No. 18, 04.05.2017, p. 2633-2637.

Research output: Contribution to journal › Article › peer-review

Sonnenschein, EC, Stierhof, M, Goralczyk, S, Vabre, FM, Pellissier, L, Hanssen, KØ, de la Cruz, M, Díaz, C, de Witte, P, Copmans, D, Andersen, JH, Hansen, E, Kristoffersen, V, Tormo, JR, Ebel, R, Milne, BF, Deng, H, Gram, L, Jaspars, M & Tabudravu, JN 2017, 'Pseudochelin A, a siderophore of Pseudoalteromonas piscicida S2040', Tetrahedron, vol. 73, no. 18, pp. 2633-2637. https://doi.org/10.1016/j.tet.2017.03.051

Sonnenschein, Eva C. ; Stierhof, Marc ; Goralczyk, Stephan ; Vabre, Floriane M. ; Pellissier, Leonie ; Hanssen, Kine Østnes ; de la Cruz, Mercedes ; Díaz, Caridad ; de Witte, Peter ; Copmans, Daniëlle ; Andersen, Jeanette Hammer ; Hansen, Espen ; Kristoffersen, Venke ; Tormo, José R. ; Ebel, Rainer ; Milne, Bruce F. ; Deng, Hai ; Gram, Lone ; Jaspars, Marcel ; Tabudravu, Jioji N. / Pseudochelin A, a siderophore of Pseudoalteromonas piscicida S2040. In: Tetrahedron. 2017 ; Vol. 73, No. 18. pp. 2633-2637.

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title = "Pseudochelin A, a siderophore of Pseudoalteromonas piscicida S2040",

abstract = "A new siderophore containing a 4,5-dihydroimidazole moiety was isolated from Pseudoalteromonas piscicida S2040 together with myxochelins A and B, alteramide A and its cycloaddition product, and bromo- and dibromoalterochromides. The structure of pseudochelin A was established by spectroscopic techniques including 2D NMR and MS/MS fragmentation data. In bioassays selected fractions of the crude extract of S2040 inhibited the opportunistic pathogen Pseudomonas aeruginosa. Pseudochelin A displayed siderophore activity in the chrome azurol S assay at concentrations higher than 50 μM, and showed weak activity against the fungus Aspergillus fumigatus, but did not display antibacterial, anti-inflammatory or anticonvulsant activity.",

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author = "Sonnenschein, {Eva C.} and Marc Stierhof and Stephan Goralczyk and Vabre, {Floriane M.} and Leonie Pellissier and Hanssen, {Kine {\O}stnes} and {de la Cruz}, Mercedes and Caridad D{\'i}az and {de Witte}, Peter and Dani{\"e}lle Copmans and Andersen, {Jeanette Hammer} and Espen Hansen and Venke Kristoffersen and Tormo, {Jos{\'e} R.} and Rainer Ebel and Milne, {Bruce F.} and Hai Deng and Lone Gram and Marcel Jaspars and Tabudravu, {Jioji N.}",

note = "Acknowledgements This work was supported by the EU seventh Framework Programme Project {\textquoteleft}PharmaSea{\textquoteright} (Grant agreement no. 312184). BFM acknowledges funding from the Portuguese Foundation for Science and Technology (CONT_DOUT/11/UC/405/10150/18/2008), and thanks DIPC and CFM (UPV/EHU) and the Laboratory for Advanced Computation (University of Coimbra) for support.",

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AU - Sonnenschein, Eva C.

AU - Stierhof, Marc

AU - Goralczyk, Stephan

AU - Vabre, Floriane M.

AU - Pellissier, Leonie

AU - Hanssen, Kine Østnes

AU - de la Cruz, Mercedes

AU - Díaz, Caridad

AU - de Witte, Peter

AU - Copmans, Daniëlle

AU - Andersen, Jeanette Hammer

AU - Hansen, Espen

AU - Kristoffersen, Venke

AU - Tormo, José R.

AU - Ebel, Rainer

AU - Milne, Bruce F.

AU - Deng, Hai

AU - Gram, Lone

AU - Jaspars, Marcel

AU - Tabudravu, Jioji N.

N1 - Acknowledgements This work was supported by the EU seventh Framework Programme Project ‘PharmaSea’ (Grant agreement no. 312184). BFM acknowledges funding from the Portuguese Foundation for Science and Technology (CONT_DOUT/11/UC/405/10150/18/2008), and thanks DIPC and CFM (UPV/EHU) and the Laboratory for Advanced Computation (University of Coimbra) for support.

PY - 2017/5/4

Y1 - 2017/5/4

N2 - A new siderophore containing a 4,5-dihydroimidazole moiety was isolated from Pseudoalteromonas piscicida S2040 together with myxochelins A and B, alteramide A and its cycloaddition product, and bromo- and dibromoalterochromides. The structure of pseudochelin A was established by spectroscopic techniques including 2D NMR and MS/MS fragmentation data. In bioassays selected fractions of the crude extract of S2040 inhibited the opportunistic pathogen Pseudomonas aeruginosa. Pseudochelin A displayed siderophore activity in the chrome azurol S assay at concentrations higher than 50 μM, and showed weak activity against the fungus Aspergillus fumigatus, but did not display antibacterial, anti-inflammatory or anticonvulsant activity.

AB - A new siderophore containing a 4,5-dihydroimidazole moiety was isolated from Pseudoalteromonas piscicida S2040 together with myxochelins A and B, alteramide A and its cycloaddition product, and bromo- and dibromoalterochromides. The structure of pseudochelin A was established by spectroscopic techniques including 2D NMR and MS/MS fragmentation data. In bioassays selected fractions of the crude extract of S2040 inhibited the opportunistic pathogen Pseudomonas aeruginosa. Pseudochelin A displayed siderophore activity in the chrome azurol S assay at concentrations higher than 50 μM, and showed weak activity against the fungus Aspergillus fumigatus, but did not display antibacterial, anti-inflammatory or anticonvulsant activity.

KW - LCMS

KW - NMR

KW - Pseudoalteromonas

KW - Pseudochelin A

KW - Siderophore

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SP - 2633

EP - 2637

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 18

ER -

Pseudochelin A, a siderophore of Pseudoalteromonas piscicida S2040

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Keywords

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