Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

Emmanuel T. Oluwabusola; Olusoji O. Adebisi; Fernando Reyes; Kojo S. Acquah; Mercedes De la Cruz; Larry L. Mweetwa; Joy E. Rajakulendran; Digby F. Warner; Deng Hai; Rainer Ebel; Marcel Jaspars

doi:10.3762/bjoc.17.156

Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

Emmanuel T. Oluwabusola, Olusoji O. Adebisi, Fernando Reyes, Kojo S. Acquah, Mercedes De la Cruz, Larry L. Mweetwa, Joy E. Rajakulendran, Digby F. Warner, Deng Hai, Rainer Ebel, Marcel Jaspars

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Abstract

Five new phenolic siderophores 1-5 were isolated from the organic extract of a culture broth in a modified SGG medium of Pseu-domonas sp. UIAU-6B, obtained from sediments collected from the Oyun river in North Central Nigeria. The structure of the new compounds, pseudomonin A-C (1-3) and pseudomobactin A and B (4 and 5) isolated alongside two known compounds, pseudomonine (6) and salicylic acid (7), were elucidated based on high-resolution mass spectrometry, 1D and 2D NMR analyses. The absolute configuration of the threonine residue in compounds 1-5 was determined by Marfey analysis. The antimicrobial eval-uation of compound 4 exhibited the most potent activity against vancomycin-sensitive Enterococcus faecium VS144754, followed by 3 and 5, with MIC values ranging from 8 to 32 mu g/mL. Compounds 2 and 3 exhibited moderate activity against Mycobacterium tuberculosis H37Rv, with MIC values of 7.8 and 15.6 mu g/mL, respectively. Plausible biosynthetic hypotheses toward the new com-pounds 1-5 were proposed.

Original language	English
Pages (from-to)	2390-2398
Number of pages	9
Journal	Beilstein journal of organic chemistry
Volume	17
DOIs	https://doi.org/10.3762/bjoc.17.156
Publication status	Published - 13 Sept 2021

Bibliographical note

We thank Russell Gray, Subha Arjuna, and Shan Wang of the Marine Biodiscovery Centre, Aberdeen for assisting in NMR, mass spectrometry and Marfey analyses, respectively. We also appreciate the support of Dr. Soji Fakoya and Blessing Akinboyo of Ondo State University of Science and Technology, Okitipupa, Nigeria, for their support in the collection of sediments.
This work was supported by funding from TETFund, Nigeria for a University Senate Based research.

Keywords

Mycobacterium tuberculosis
Phenolic siderophores
pseudomonine
Pseudomonas sp
vancomycin-sensitive Enterococcus faecium

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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Cite this

Oluwabusola, E. T., Adebisi, O. O., Reyes, F., Acquah, K. S., De la Cruz, M., Mweetwa, L. L., Rajakulendran, J. E., Warner, D. F., Hai, D., Ebel, R., & Jaspars, M. (2021). Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B. Beilstein journal of organic chemistry, 17, 2390-2398. https://doi.org/10.3762/bjoc.17.156

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title = "Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B",

abstract = "Five new phenolic siderophores 1-5 were isolated from the organic extract of a culture broth in a modified SGG medium of Pseu-domonas sp. UIAU-6B, obtained from sediments collected from the Oyun river in North Central Nigeria. The structure of the new compounds, pseudomonin A-C (1-3) and pseudomobactin A and B (4 and 5) isolated alongside two known compounds, pseudomonine (6) and salicylic acid (7), were elucidated based on high-resolution mass spectrometry, 1D and 2D NMR analyses. The absolute configuration of the threonine residue in compounds 1-5 was determined by Marfey analysis. The antimicrobial eval-uation of compound 4 exhibited the most potent activity against vancomycin-sensitive Enterococcus faecium VS144754, followed by 3 and 5, with MIC values ranging from 8 to 32 mu g/mL. Compounds 2 and 3 exhibited moderate activity against Mycobacterium tuberculosis H37Rv, with MIC values of 7.8 and 15.6 mu g/mL, respectively. Plausible biosynthetic hypotheses toward the new com-pounds 1-5 were proposed.",

keywords = "Mycobacterium tuberculosis, Phenolic siderophores, pseudomonine, Pseudomonas sp, vancomycin-sensitive Enterococcus faecium",

author = "Oluwabusola, {Emmanuel T.} and Adebisi, {Olusoji O.} and Fernando Reyes and Acquah, {Kojo S.} and {De la Cruz}, Mercedes and Mweetwa, {Larry L.} and Rajakulendran, {Joy E.} and Warner, {Digby F.} and Deng Hai and Rainer Ebel and Marcel Jaspars",

note = "We thank Russell Gray, Subha Arjuna, and Shan Wang of the Marine Biodiscovery Centre, Aberdeen for assisting in NMR, mass spectrometry and Marfey analyses, respectively. We also appreciate the support of Dr. Soji Fakoya and Blessing Akinboyo of Ondo State University of Science and Technology, Okitipupa, Nigeria, for their support in the collection of sediments. This work was supported by funding from TETFund, Nigeria for a University Senate Based research.",

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AU - Oluwabusola, Emmanuel T.

AU - Adebisi, Olusoji O.

AU - Reyes, Fernando

AU - Acquah, Kojo S.

AU - De la Cruz, Mercedes

AU - Mweetwa, Larry L.

AU - Rajakulendran, Joy E.

AU - Warner, Digby F.

AU - Hai, Deng

AU - Ebel, Rainer

AU - Jaspars, Marcel

N1 - We thank Russell Gray, Subha Arjuna, and Shan Wang of the Marine Biodiscovery Centre, Aberdeen for assisting in NMR, mass spectrometry and Marfey analyses, respectively. We also appreciate the support of Dr. Soji Fakoya and Blessing Akinboyo of Ondo State University of Science and Technology, Okitipupa, Nigeria, for their support in the collection of sediments. This work was supported by funding from TETFund, Nigeria for a University Senate Based research.

PY - 2021/9/13

Y1 - 2021/9/13

N2 - Five new phenolic siderophores 1-5 were isolated from the organic extract of a culture broth in a modified SGG medium of Pseu-domonas sp. UIAU-6B, obtained from sediments collected from the Oyun river in North Central Nigeria. The structure of the new compounds, pseudomonin A-C (1-3) and pseudomobactin A and B (4 and 5) isolated alongside two known compounds, pseudomonine (6) and salicylic acid (7), were elucidated based on high-resolution mass spectrometry, 1D and 2D NMR analyses. The absolute configuration of the threonine residue in compounds 1-5 was determined by Marfey analysis. The antimicrobial eval-uation of compound 4 exhibited the most potent activity against vancomycin-sensitive Enterococcus faecium VS144754, followed by 3 and 5, with MIC values ranging from 8 to 32 mu g/mL. Compounds 2 and 3 exhibited moderate activity against Mycobacterium tuberculosis H37Rv, with MIC values of 7.8 and 15.6 mu g/mL, respectively. Plausible biosynthetic hypotheses toward the new com-pounds 1-5 were proposed.

AB - Five new phenolic siderophores 1-5 were isolated from the organic extract of a culture broth in a modified SGG medium of Pseu-domonas sp. UIAU-6B, obtained from sediments collected from the Oyun river in North Central Nigeria. The structure of the new compounds, pseudomonin A-C (1-3) and pseudomobactin A and B (4 and 5) isolated alongside two known compounds, pseudomonine (6) and salicylic acid (7), were elucidated based on high-resolution mass spectrometry, 1D and 2D NMR analyses. The absolute configuration of the threonine residue in compounds 1-5 was determined by Marfey analysis. The antimicrobial eval-uation of compound 4 exhibited the most potent activity against vancomycin-sensitive Enterococcus faecium VS144754, followed by 3 and 5, with MIC values ranging from 8 to 32 mu g/mL. Compounds 2 and 3 exhibited moderate activity against Mycobacterium tuberculosis H37Rv, with MIC values of 7.8 and 15.6 mu g/mL, respectively. Plausible biosynthetic hypotheses toward the new com-pounds 1-5 were proposed.

KW - Mycobacterium tuberculosis

KW - Phenolic siderophores

KW - pseudomonine

KW - Pseudomonas sp

KW - vancomycin-sensitive Enterococcus faecium

U2 - 10.3762/bjoc.17.156

DO - 10.3762/bjoc.17.156

M3 - Article

SN - 1860-5397

VL - 17

SP - 2390

EP - 2398

JO - Beilstein journal of organic chemistry

JF - Beilstein journal of organic chemistry

ER -

Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

Abstract

Bibliographical note

Keywords

UN SDGs

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