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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...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2018
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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. |
format | Online Article Text |
id | pubmed-6212950 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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