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New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157

Fractionation of the bioactive extract of a culture of the marine derived actinomycete Streptomyces cyaneofuscatus M-157 led to the isolation of the known 3-hydroxyquinaldic acid (4), its amide (5) and three new derivatives (1–3) containing different amino acid residues. The structures of the new mo...

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Autores principales: Ortiz-López, Francisco Javier, Alcalde, Elsa, Sarmiento-Vizcaíno, Aida, Díaz, Caridad, Cautain, Bastien, García, Luis A., Blanco, Gloria, Reyes, Fernando
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6212950/
https://www.ncbi.nlm.nih.gov/pubmed/30297652
http://dx.doi.org/10.3390/md16100371
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author Ortiz-López, Francisco Javier
Alcalde, Elsa
Sarmiento-Vizcaíno, Aida
Díaz, Caridad
Cautain, Bastien
García, Luis A.
Blanco, Gloria
Reyes, Fernando
author_facet Ortiz-López, Francisco Javier
Alcalde, Elsa
Sarmiento-Vizcaíno, Aida
Díaz, Caridad
Cautain, Bastien
García, Luis A.
Blanco, Gloria
Reyes, Fernando
author_sort Ortiz-López, Francisco Javier
collection PubMed
description Fractionation of the bioactive extract of a culture of the marine derived actinomycete Streptomyces cyaneofuscatus M-157 led to the isolation of the known 3-hydroxyquinaldic acid (4), its amide (5) and three new derivatives (1–3) containing different amino acid residues. The structures of the new molecules (1–3), including their absolute configuration, were determined by the analysis of their ESI-TOF MS and one-dimensional (1D) and two-dimensional (2D) NMR spectra and advanced Marfey’s analysis of their hydrolyzation products. Compound 3 spontaneously dimerized in solution to give the disulfide derivative 6. Unfortunately, none of the new compounds isolated confirmed the antimicrobial activity found in the bacterial extract, perhaps indicating that such antibacterial activity might be due to presence in the extract at the trace level of larger bioactive 3-hydroxyquinaldic acid derivatives from which compounds 1–3 are biosynthetic precursors. Cytotoxicity tests confirmed the moderate and weak IC(50) values of 15.6 and 51.5 µM for compounds 5 and 1, respectively.
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spelling pubmed-62129502018-11-09 New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157 Ortiz-López, Francisco Javier Alcalde, Elsa Sarmiento-Vizcaíno, Aida Díaz, Caridad Cautain, Bastien García, Luis A. Blanco, Gloria Reyes, Fernando Mar Drugs Article Fractionation of the bioactive extract of a culture of the marine derived actinomycete Streptomyces cyaneofuscatus M-157 led to the isolation of the known 3-hydroxyquinaldic acid (4), its amide (5) and three new derivatives (1–3) containing different amino acid residues. The structures of the new molecules (1–3), including their absolute configuration, were determined by the analysis of their ESI-TOF MS and one-dimensional (1D) and two-dimensional (2D) NMR spectra and advanced Marfey’s analysis of their hydrolyzation products. Compound 3 spontaneously dimerized in solution to give the disulfide derivative 6. Unfortunately, none of the new compounds isolated confirmed the antimicrobial activity found in the bacterial extract, perhaps indicating that such antibacterial activity might be due to presence in the extract at the trace level of larger bioactive 3-hydroxyquinaldic acid derivatives from which compounds 1–3 are biosynthetic precursors. Cytotoxicity tests confirmed the moderate and weak IC(50) values of 15.6 and 51.5 µM for compounds 5 and 1, respectively. MDPI 2018-10-08 /pmc/articles/PMC6212950/ /pubmed/30297652 http://dx.doi.org/10.3390/md16100371 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Ortiz-López, Francisco Javier
Alcalde, Elsa
Sarmiento-Vizcaíno, Aida
Díaz, Caridad
Cautain, Bastien
García, Luis A.
Blanco, Gloria
Reyes, Fernando
New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157
title New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157
title_full New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157
title_fullStr New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157
title_full_unstemmed New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157
title_short New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157
title_sort new 3-hydroxyquinaldic acid derivatives from cultures of the marine derived actinomycete streptomyces cyaneofuscatus m-157
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6212950/
https://www.ncbi.nlm.nih.gov/pubmed/30297652
http://dx.doi.org/10.3390/md16100371
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