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      Terretonin N: A New Meroterpenoid from Nocardiopsis sp.

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          Abstract

          Terretonin N ( 1), a new highly oxygenated and unique tetracyclic 6-hydroxymeroterpenoid, was isolated together with seven known compounds from the ethyl acetate extract of a solid-state fermented culture of Nocardiopsis sp. Their structures were elucidated by spectroscopic analysis. The structure and absolute configuration of 1 were unambiguously determined by X-ray crystallography. The isolation and taxonomic characterization of Nocardiopsis sp. is reported. The antimicrobial activity and cytotoxicity of the strain extract and compound 1 were studied using different microorganisms and a cervix carcinoma cell line, respectively.

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          Most cited references38

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          Biology and chemistry of endophytes.

          This review focuses on new endophyte-related findings in biology and ecology, and also summarises the various metabolites isolated from endophytes.
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            Terpene synthases are widely distributed in bacteria.

            Odoriferous terpene metabolites of bacterial origin have been known for many years. In genome-sequenced Streptomycetaceae microorganisms, the vast majority produces the degraded sesquiterpene alcohol geosmin. Two minor groups of bacteria do not produce geosmin, with one of these groups instead producing other sesquiterpene alcohols, whereas members of the remaining group do not produce any detectable terpenoid metabolites. Because bacterial terpene synthases typically show no significant overall sequence similarity to any other known fungal or plant terpene synthases and usually exhibit relatively low levels of mutual sequence similarity with other bacterial synthases, simple correlation of protein sequence data with the structure of the cyclized terpene product has been precluded. We have previously described a powerful search method based on the use of hidden Markov models (HMMs) and protein families database (Pfam) search that has allowed the discovery of monoterpene synthases of bacterial origin. Using an enhanced set of HMM parameters generated using a training set of 140 previously identified bacterial terpene synthase sequences, a Pfam search of 8,759,463 predicted bacterial proteins from public databases and in-house draft genome data has now revealed 262 presumptive terpene synthases. The biochemical function of a considerable number of these presumptive terpene synthase genes could be determined by expression in a specially engineered heterologous Streptomyces host and spectroscopic identification of the resulting terpene products. In addition to a wide variety of terpenes that had been previously reported from fungal or plant sources, we have isolated and determined the complete structures of 13 previously unidentified cyclic sesquiterpenes and diterpenes.
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              Marine natural products.

              This review covers the literature published in 2005 for marine natural products, with 704 citations (493 for the period January to December 2005) referring to compounds isolated from marine microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, coelenterates, bryozoans, molluscs, tunicates and echinoderms. The emphasis is on new compounds (812 for 2005), together with their relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.
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                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
                MDPI
                1420-3049
                31 January 2018
                February 2018
                : 23
                : 2
                : 299
                Affiliations
                [1 ]Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, Germany; abdohamed481@ 123456yahoo.com (A.H.); ahmedshukri_sci@ 123456yahoo.com (A.S.A.); marcel.frese@ 123456uni-bielefeld.de (M.F.)
                [2 ]Department of Chemistry, Faculty of Science, Al-Azhar University, Nasr City-Cairo 11884, Egypt; atefel_haddad@ 123456yahoo.com (A.F.E.-H.); tarekmostafaahmedibrahim@ 123456yahoo.com (T.M.A.I.)
                [3 ]Department of Microbial Chemistry, Division of Genetic Engineering and Biotechnology Research, National Research Centre, El-Buhouth St. 33, Dokki-Cairo 12622, Egypt
                [4 ]Department of Chemistry, Inorganic and Structural Chemistry, Bielefeld University, D-33501 Bielefeld, Germany; georg.stammler@ 123456uni-bielefeld.de
                [5 ]Department of Chemistry of Natural Compounds, Pharmaceutical and Drug Industries Research Division, National Research Centre, El-Buhouth St. 33, Dokki-Cairo 12622, Egypt
                Author notes
                [* ]Correspondence: norbert.sewald@ 123456uni-bielefeld.de (N.S.); mshaaba@ 123456gmail.com (M.S.); Tel.: +49-521-106-2051 (N.S.); +20-227-01728-1550 (M.S.)
                Author information
                https://orcid.org/0000-0003-4119-7447
                https://orcid.org/0000-0001-7123-1904
                https://orcid.org/0000-0002-0309-2655
                https://orcid.org/0000-0001-9281-2505
                Article
                molecules-23-00299
                10.3390/molecules23020299
                6017310
                29385078
                62694b85-8fa1-4635-8321-d8a55e7f39b5
                © 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/).

                History
                : 21 December 2017
                : 28 January 2018
                Categories
                Article

                nocardiopsis sp. lgo5,terretonin n,6-hydroxymeroterpenoid,antimicrobial activity,cytotoxicity

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