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      New Cytotoxic Cyclic Peptide from the Marine Sponge-Associated Nocardiopsis sp. UR67

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          Abstract

          A new cyclic hexapeptide, nocardiotide A ( 1), together with three known compounds—tryptophan ( 2), kynurenic acid ( 3), and 4-amino-3-methoxy benzoic acid ( 4)—were isolated and identified from the broth culture of Nocardiopsis sp. UR67 strain associated with the marine sponge Callyspongia sp. from the Red Sea. The structure elucidation of the isolated compounds were determined based on detailed spectroscopic data including 1D and 2D nuclear magnetic resonance (NMR) experimental analyses in combination with high resolution electrospray ionization mass spectrometry (HR-ESI-MS), while the absolute stereochemistry of all amino acids components of nocardiotide A ( 1) was deduced using Marfey’s method. Additionally, ten known metabolites were dereplicated using HR-ESI-MS analysis. Nocardiotide A ( 1) displayed significant cytotoxic effects towards the murine CT26 colon carcinoma, human HeLa cervix carcinoma, and human MM.1S multiple myeloma cell lines. The results obtained revealed sponge-associated Nocardiopsis as a substantial source of lead natural products with pronounced pharmacological activities.

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          The genus Nocardiopsis represents a phylogenetically coherent taxon and a distinct actinomycete lineage: proposal of Nocardiopsaceae fam. nov.

          N Rainey, R M Kroppenstedt, E Stackebrandt … (1996)
          The genus Nocardiopsis was shown to be phylogenetically coherent and to represent a distinct lineage within the radiation of the order Actinomycetales. The closest relatives of the genus Nocardiopsis are members of the genera Actinomadura, Thermomonospora, Streptosporangium, and Microtetraspora. The intrageneric structure of the genus Nocardiopsis is shown to consist of a highly related species group containing Nocardiopsis dassonvillei, Nocardiopsis alborubida, and Nocardiopsis antarctica and a second group of less highly related species comprising Nocardiopsis alba subsp. alba, Nocardiopsis alba subsp. prasina, and Nocardiopsis listeri. Nocardiopsis lucentensis occupies a position intermediate between the two species groups. The results of a 16S ribosomal DNA sequence analysis are generally consistent with the available chemotaxonomic, phenotypic, and DNA-DNA hybridization data. The phylogenetic position and the morpho- and chemotaxonomic properties of Nocardiopsis species support the creation of a family for the genus Nocardiopsis, Nocardiopsaceae fam. nov.
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            Pharmaceutically active secondary metabolites of marine actinobacteria.

            Il-kwon Kim, Jayachandran Venkatesan, Panchanathan Manivasagan … (2014)
            Marine actinobacteria are one of the most efficient groups of secondary metabolite producers and are very important from an industrial point of view. Many representatives of the order Actinomycetales are prolific producers of thousands of biologically active secondary metabolites. Actinobacteria from terrestrial sources have been studied and screened since the 1950s, for many important antibiotics, anticancer, antitumor and immunosuppressive agents. However, frequent rediscovery of the same compounds from the terrestrial actinobacteria has made them less attractive for screening programs in the recent years. At the same time, actinobacteria isolated from the marine environment have currently received considerable attention due to the structural diversity and unique biological activities of their secondary metabolites. They are efficient producers of new secondary metabolites that show a range of biological activities including antibacterial, antifungal, anticancer, antitumor, cytotoxic, cytostatic, anti-inflammatory, anti-parasitic, anti-malaria, antiviral, antioxidant, anti-angiogenesis, etc. In this review, an evaluation is made on the current status of research on marine actinobacteria yielding pharmaceutically active secondary metabolites. Bioactive compounds from marine actinobacteria possess distinct chemical structures that may form the basis for synthesis of new drugs that could be used to combat resistant pathogens. With the increasing advancement in science and technology, there would be a greater demand for new bioactive compounds synthesized by actinobacteria from various marine sources in future. Copyright © 2013 Elsevier GmbH. All rights reserved.
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              Phylogenetic diversity of bacteria associated with the marine sponge Rhopaloeides odorabile.

              Koa N. Webster, Linda Blackall, Kyle Hill … (2000)
              Molecular techniques were employed to document the microbial diversity associated with the marine sponge Rhopaloeides odorabile. The phylogenetic affiliation of sponge-associated bacteria was assessed by 16S rRNA sequencing of cloned DNA fragments. Fluorescence in situ hybridization (FISH) was used to confirm the presence of the predominant groups indicated by 16S rDNA analysis. The community structure was extremely diverse with representatives of the Actinobacteria, low-G+C gram-positive bacteria, the beta- and gamma-subdivisions of the Proteobacteria, Cytophaga/Flavobacterium, green sulfur bacteria, green nonsulfur bacteria, planctomycetes, and other sequence types with no known close relatives. FISH probes revealed the spatial location of these bacteria within the sponge tissue, in some cases suggesting possible symbiotic functions. The high proportion of 16S rRNA sequences derived from novel actinomycetes is good evidence for the presence of an indigenous marine actinomycete assemblage in R. odorabile. High microbial diversity was inferred from low duplication of clones in a library with 70 representatives. Determining the phylogenetic affiliation of sponge-associated microorganisms by 16S rRNA analysis facilitated the rational selection of culture media and isolation conditions to target specific groups of well-represented bacteria for laboratory culture. Novel media incorporating sponge extracts were used to isolate bacteria not previously recovered from this sponge.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Mar Drugs
                Journal ID (iso-abbrev): Mar Drugs
                Journal ID (publisher-id): marinedrugs
                Title: Marine Drugs
                Publisher: MDPI
                ISSN (Electronic): 1660-3397
                Publication date (Electronic): 21 August 2018
                Publication date Collection: September 2018
                Volume: 16
                Issue: 9
                Electronic Location Identifier: 290
                Affiliations
                [1 ]Department of Pharmacognosy, Faculty of Pharmacy, Sohag University, 82524 Sohag, Egypt; dralyaahatem@ 123456gmail.com
                [2 ]Department of Pharmacognosy, Faculty of Pharmacy, Minia University, 61519 Minia, Egypt; eman_zekry@ 123456mu.edu.eg (E.Z.A.); drsamaryehia@ 123456gmail.com (S.Y.D.); m_fouad2000@ 123456yahoo.com (M.A.F.)
                [3 ]Department of Biochemistry, Faculty of Science, Center for Science and Medical Research, University of Jeddah, 80203 Jeddah, Saudi Arabia; dhajjar@ 123456uj.edu.sa
                [4 ]Division of Molecular Internal Medicine, Department of Internal Medicine II, University Hospital Würzburg, Röntenring 11, 97070 Würzburg, Germany; Mohamed_M@ 123456klinik.uni-wuerzburg.de (M.A.A.); harald.wajant@ 123456uni-wuerzburg.de (H.W.)
                [5 ]Division of Genetic Engineering and Biotechnology, Department of Microbial Biotechnology, National Research Centre, El Buhouth St., Dokki, 12622 Giza, Egypt
                [6 ]Department of Pharmacognosy, Faculty of Pharmacy, Deraya University, Universities Zone, 61111 New Minia City, Egypt; mskamel@ 123456yahoo.com
                [7 ]Biosystems Chemistry, Department of Chemistry and Center for Integrated Protein Science Munich (CIPSM), Technical University of Munich, Lichtenbergstraβe 4, 85748 Garching, Germany
                Author notes
                [* ]Correspondence: tobias.gulder@ 123456ch.tum.de (T.A.M.G.); usama.ramadan@ 123456mu.edu.eg (U.R.A.); Tel.: +49-89-289-13833 (T.A.M.G.); +20-86234-9075 (U.R.A.); Fax: +20-86237-6678 (U.R.A.)
                Author information
                https://orcid.org/0000-0002-2005-3949
                https://orcid.org/0000-0002-1014-6922
                Article
                Publisher ID: marinedrugs-16-00290
                DOI: 10.3390/md16090290
                PMC ID: 6174345
                PubMed ID: 30134565
                SO-VID: 348407c7-98da-4aea-8bc3-67951e1bc85c
                Copyright © © 2018 by the authors.
                License:

                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/).

                History
                Date received : 30 July 2018
                Date accepted : 17 August 2018
                Categories
                Subject: Article

                ScienceOpen disciplines: Pharmacology & Pharmaceutical medicine
                Keywords: nocardiopsis,cyclic hexapeptide,cytotoxicity,marine actinomycetes,sponges
                Data availability:
                ScienceOpen disciplines: Pharmacology & Pharmaceutical medicine
                Keywords: nocardiopsis, cyclic hexapeptide, cytotoxicity, marine actinomycetes, sponges

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