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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences


IMPACT FACTOR 2017: 0.757

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Volume 72, Issue 1

Issues

New oxaphenalene derivative from marine-derived Streptomyces griseorubens sp. ASMR4

Abdelaaty Hamed
  • Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, Germany
  • Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City-Cairo 11884, Egypt
  • Other articles by this author:
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/ Ahmed S. Abdel-Razek
  • Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, Germany
  • Microbial Chemistry Department, Division of Genetic Engineering and Biotechnology Research, National Research Centre, Dokki-Cairo 12622, Egypt
  • Other articles by this author:
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/ Marcel Frese
  • Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, Germany
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/ Daniel Wibberg / Atef F. El-Haddad / Tarek M. A. Ibrahim / Jörn Kalinowski / Norbert Sewald
  • Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, Germany
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/ Mohamed Shaaban
  • Corresponding author
  • Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, Germany
  • Chemistry of Natural Compounds Department, Division of Pharmaceutical Industries, National Research Centre, El-Behoos St. 33, Dokki-Cairo 12622, Egypt
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Published Online: 2016-12-28 | DOI: https://doi.org/10.1515/znb-2016-0145

Abstract

During our search for novel bioactive compounds from extremophilic actinomycetes, the new Streptomyces griseorubens sp. ASMR4 was isolated from a soft coral collected in the Red Sea at the Hurghada coast, Egypt, and characterized taxonomically. It was fermented on large scale using a modified solid rice medium as the first example for actinomycetes so far. Work-up and purification of the strain extract using different chromatographic techniques afforded the new oxaphenalene derivative, 8-hydroxy-2-(2-hydroxypropyl)-7-acetyl-1-oxaphenalene (1a), together with seven known metabolites: ferulic acid (2), glycerol linoleate, linoleic acid methyl ester, (3R,4R)-3,4-dihydroxy-3-methylpentan-2-one/(3S,4R)-3,4-dihydroxy-3-methylpentan-2-one, anthranilic acid, phenylacetic acid, and benzoic acid. The chemical structure of the new compound (1a) was confirmed by extensive 1D and 2D NMR spectroscopy, high-resolution electron impact mass measurements, and by comparison with literature data. The antimicrobial activity of the strain extract and compounds 1a and 2 were studied using a panel of pathogenic microorganisms. The in vitro cytotoxicity of the bacterial extract was studied against the human cervix carcinoma cell line (KB-3-1) and its multi-drug-resistant subclone (KB-V1).

This article offers supplementary material which is provided at the end of the article.

Keywords: antimicrobial activity; cytotoxicity; oxaphenalene derivative; Streptomyces griseorubens sp. ASMR4; taxonomy

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About the article

Received: 2016-06-29

Accepted: 2016-11-03

Published Online: 2016-12-28

Published in Print: 2017-01-01


Citation Information: Zeitschrift für Naturforschung B, Volume 72, Issue 1, Pages 53–62, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2016-0145.

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