Next Article in Journal
Optimization of Growth and Carotenoid Production by Haloferax mediterranei Using Response Surface Methodology
Previous Article in Journal
Characterization of a Novel N-Acylhomoserine Lactonase RmmL from Ruegeria mobilis YJ3
Previous Article in Special Issue
Aspergixanthones I–K, New Anti-Vibrio Prenylxanthones from the Marine-Derived Fungus Aspergillus sp. ZA-01
Article Menu

Export Article

Open AccessArticle
Mar. Drugs 2018, 16(10), 371; https://doi.org/10.3390/md16100371

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

1
Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 3, Parque Tecnológico de Ciencias de la Salud, E-18016 Granada, Spain
2
Departamento de Biología Funcional, Área de Microbiología, and Instituto Universitario de Oncología del Principado de Asturias, Universidad de Oviedo, 33006 Oviedo, Spain
3
Departamento de Ingeniería Química y Tecnología del Medio Ambiente, Área de Ingeniería Química, Universidad de Oviedo, 33006 Oviedo, Spain
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 13 September 2018 / Revised: 4 October 2018 / Accepted: 4 October 2018 / Published: 8 October 2018
(This article belongs to the Special Issue Isolation and Structure Elucidation of Marine Secondary Metabolites)
Full-Text   |   PDF [1313 KB, uploaded 10 October 2018]   |  

Abstract

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 (13) containing different amino acid residues. The structures of the new molecules (13), 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 13 are biosynthetic precursors. Cytotoxicity tests confirmed the moderate and weak IC50 values of 15.6 and 51.5 µM for compounds 5 and 1, respectively. View Full-Text
Keywords: 3-hydroxyquinaldic acid; Streptomyces cyaneofuscatus; deep-sea actinobacteria; Cantabrian Sea 3-hydroxyquinaldic acid; Streptomyces cyaneofuscatus; deep-sea actinobacteria; Cantabrian Sea
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

Ortiz-López, F.J.; Alcalde, E.; Sarmiento-Vizcaíno, A.; Díaz, C.; Cautain, B.; García, L.A.; Blanco, G.; Reyes, F. New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157. Mar. Drugs 2018, 16, 371.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top