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      “Head-to-Side-Chain” Cyclodepsipeptides of Marine Origin

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          Abstract

          Since the late 1980s, a large number of depsipeptides that contain a new topography, referred to as “head-to-side-chain” cyclodepsipeptides, have been isolated and characterized. These peptides present a unique structural arrangement that comprises a macrocyclic region closed through an ester bond between the C-terminus and a β-hydroxyl group, and terminated with a polyketide moiety or a more simple branched aliphatic acid. This structural pattern, the presence of unique and complex residues, and relevant bioactivity are the main features shared by all the members of this new class of depsipeptides, which are reviewed herein.

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          Big effects from small changes: possible ways to explore nature's chemical diversity.

          Helge Bode, Barbara Bethe, Regina Höfs … (2002)
          Fungi or bacteria that produce secondary metabolites often have the potential to bring up various compounds from a single strain. The molecular basis for this well-known observation was confirmed in the last few years by several sequencing projects of different microorganisms. Besides well-known examples about induction of a selected biosynthesis (for example, by high- or low-phosphate cultivation media), no overview about the potential in this field for finding natural products was given. We have investigated the systematic alteration of easily accessible cultivation parameters (for example, media composition, aeration, culture vessel, addition of enzyme inhibitors) in order to increase the number of secondary metabolites available from one microbial source. We termed this way of revealing nature's chemical diversity the 'OSMAC (One Strain-Many Compounds) approach' and by using it we were able to isolate up to 20 different metabolites in yields up to 2.6 g L(-1) from a single organism. These compounds cover nearly all major natural product families, and in some cases the high production titer opens new possibilities for semisynthetic methods to enhance even more the chemical diversity of selected compounds. The OSMAC approach offers a good alternative to industrial high-throughput screening that focuses on the active principle in a distinct bioassay. In consequence, the detection of additional compounds that might be of interest as lead structures in further bioassays is impossible and clearly demonstrates the deficiency of the industrial procedure. Furthermore, our approach seems to be a useful tool to detect those metabolites that are postulated to be the final products of an amazing number of typical secondary metabolite gene clusters identified in several microorganisms. If one assumes a (more or less) defined reservoir of genetic possibilities for several biosynthetic pathways in one strain that is used for a highly flexible production of secondary metabolites depending on the environment, the OSMAC approach might give more insight into the role of secondary metabolism in the microbial community or during the evolution of life itself.
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            Chemistry. The renaissance of natural products as drug candidates.

            Ian Paterson, Judy Anderson (2005)
            Article 0 comments Cited 112 times – based on 0 reviews     Review now
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              New aspects of natural products in drug discovery.

              Dominic M. K. Lam (2007)
              During the past 15 years, most large pharmaceutical companies have decreased the screening of natural products for drug discovery in favor of synthetic compound libraries. Main reasons for this include the incompatibility of natural product libraries with high-throughput screening and the marginal improvement in core technologies for natural product screening in the late 1980s and early 1990 s. Recently, the development of new technologies has revolutionized the screening of natural products. Applying these technologies compensates for the inherent limitations of natural products and offers a unique opportunity to re-establish natural products as a major source for drug discovery. Examples of these new advances and technologies are described in this review.
              Article 0 comments Cited 101 times – based on 0 reviews     Review now
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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 May 2013
                Publication date Collection: May 2013
                Volume: 11
                Issue: 5
                Pages: 1693-1717
                Affiliations
                [1 ]Institute for Research in Biomedicine (IRB Barcelona), Baldiri Reixac 10, Barcelona 08028, Spain
                [2 ]CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Baldiri Reixac 10, Barcelona 08028, Spain
                [3 ]Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1-11, Barcelona 08028, Spain
                [4 ]School of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South Africa
                Author notes
                [* ] Authors to whom correspondence should be addressed; E-Mails: marta.pelay@ 123456irbbarcelona.org (M.P.-G.); judit.tulla@ 123456irbbarcelona.org (J.T.-P.); albericio@ 123456irbbarcelona.org (F.A.); Tel.: +34-93-403-70-88; Fax: +34-93-403-71-26.
                Article
                Publisher ID: marinedrugs-11-01693
                DOI: 10.3390/md11051693
                PMC ID: 3707169
                PubMed ID: 23697952
                SO-VID: efda7c1e-e3a8-48a9-966f-71090bbabdde
                Copyright © © 2013 by the authors; licensee MDPI, Basel, Switzerland.
                License:

                This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

                History
                Date received : 12 March 2013
                Date revision received : 07 April 2013
                Date accepted : 23 April 2013
                Categories
                Subject: Review

                ScienceOpen disciplines: Pharmacology & Pharmaceutical medicine
                Keywords: natural products,peptides,polyketides,therapeutic agents
                Data availability:
                ScienceOpen disciplines: Pharmacology & Pharmaceutical medicine
                Keywords: natural products, peptides, polyketides, therapeutic agents

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