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Bioactive Compounds from the Marine Sponge Geodia Barretti

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Bioactive Compounds from the Marine Sponge Geodia Barretti Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Pharmacy 32 Bioactive Compounds from the Marine Sponge Geodia barretti Characterization, Antifouling Activity and Molecular Targets MARTIN SJÖGREN ACTA UNIVERSITATIS UPSALIENSIS ISSN 1651-6192 UPPSALA ISBN 91-554-6534-X 2006 urn:nbn:se:uu:diva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eodia barretti , s y m ' i " Balanus improvius a ' 56C! ! %& ' ! ' ( )*+' ' ,-*)./0 ' # E ./0' #$ 4..5 $6$%# 4.5 %676$768 6$3%3 )" == ,B,= F G 6$3%3+ Till Mia, Tilda och min familj Cover picture by Tomas Lundälv List of Papers This thesis is based on the following papers, which will be referred to by their Roman numerals: I Antifouling activity of brominated cyclopeptides from the marine sponge Geodia barretti Sjögren, M., Göransson, U., Johnsson, AL., Dahlström, M., Andersson, R., Bergman, J., Bohlin, L. Journal of Natural Products 2004, 67, 368-372. II Synthesis of barettin Johnson, AL., Bergman, J., Sjögren, M., Bohlin, L. Tetrahedron 2004, 60, 961-965 III Recruitment in the field of Balanus improvisus and Mytilus edulis in response to the antifouling cyclopeptides barettin and 8,9- dihydrobarettin from the marine sponge Geodia barretti Sjögren, M., Dahlström, M., Göransson, U., Jonsson, PR., Bohlin, L. Biofouling 2004, 6, 291-297 IV Antifouling activity of synthesized structure analogs of the sponge metabolite barettin Sjögren, M., Johnson. AL., Hedner, E., Dahlström, M., Göransson, U., Shirani, H., Bergman, J., Bohlin, L. Accepted for publication in Peptides V Brominated cyclodipeptides from the marine sponge Geodia barrette as selective 5-HT ligands Sjögren, M., Hedner, E., Frändberg, PA., Johansson, T., Göransson, U., Dahlström, M., Jonsson, PR., Nyberg, F., Bohlin, L. In manuscript Contents 1. Introduction...............................................................................................11 1. 1 Secondary metabolites.......................................................................11 1.2 Host defence interactions as a basis for finding new bioactive compounds ...............................................................................................13 1.3 Bioactive compounds of marine origin with the potential of serving as drug leads .................................................................................................14 1.4. Bioactivity of Swedish marine organisms – focus on the sponge Geodia barretti.........................................................................................15 1.5. Marine secondary metabolites as antifoulants...................................16 1.5.1. Study organism: biology of sponges..........................................16 1.5.2 Marine biofouling and antifouling compounds of marine origin17 1.6. History of barettin .............................................................................18 1.7. Synthesis of natural products ............................................................19 1.8. Bioactivity of diketopiperazines........................................................20 1.9. Analogs of bioactive natural products...............................................20 1.10. Molecular target; highlighting G protein-coupled receptors ...........21 1.11. Aims of the present study................................................................23 2. Methodological considerations .................................................................24 2.1. Bioassay-guided fractionation and isolation .....................................24 2.2. Structure elucidation ........................................................................25 2.3. Rearing of barnacle cypris larvae......................................................26 2.4. Experimental design..........................................................................27 2.5. Synthesis of barettin and 8,9-dihydrobarettin ...................................28 2.6. Methods in field experiments............................................................29 2.7. Analogs of the dipeptides barettin and dipodazine............................29 2.7.1 Peptide synthesis.........................................................................29 2.8. Receptor ligand binding assay...........................................................31 3. Results and discussion ..............................................................................32 3.1. Settlement inhibition displayed by barettin and 8,9-dihydrobarettin 32 3.2. Synthesised barettins as antifouling compounds...............................33 3.3. Field experiment to evaluate antifouling activity..............................33 3.4. Analogs as antifouling compounds ...................................................36 3.5. Barettins as selective serotonin ligands.............................................39 Concluding remarks......................................................................................42 Populärvetenskaplig sammanfattning ...........................................................45 Acknowledgement ........................................................................................47 References.....................................................................................................49 Abbreviations aa amino acid Ala Alanine Arg Arginine AcN Acetonitrile Br Bromine DKP:s Diketopiperazines DMSO Dimethylsulphoxide EC50 Effective Concentration (50%) EtOH Ethanol FSW Filtered Seawater GPCR G protein-coupled receptors His Histidine HPLC High Performance Liquid Chromatography LC Liquid Chromatography Leu Leucine MS Mass Spectrometry MW Molecular weight NMR Nuclear Magnetic Resonance Phe Phenylalanine Pro Proline RP Reversed Phase RP-SPE Reversed Phase-Solid Phase Extraction SPC Self Polishing Copolymer SPE Solid Phase Extraction TBTO Tributyltinoxide Tyr Tyrosine Trp Tryptophan Val Valine 1. Introduction 1. 1 Secondary metabolites Fossil records indicate that humans have used plants for medicinal purposes since at least the Mid Paleolithic age (app. 60 000 years ago) (Solecki and Shanidar, 1975). Apart from archeological records, there are written records dating back at least 5000 years that report on plants for medicinal use (Raskin et al., 2002). The rich variety of bioactive compounds originating from natural sources such as terrestrial plants, fungi and bacteria has been a very valuable source both for compounds used as drugs and as leads in drug discovery (Fabricant and Farnsworth, 2001). Well-known examples with a direct use as drugs are antibiotics from actinomycetes, the antitumor agent paclitaxel from the yew tree Taxus brevifolia and morphine, vinblastine, vincristine and reserpine from different plant sources. It is estimated that 122 compounds from 94 species of plants are used globally as drugs. The number of described higher plants is estimated at 250 000 (but may be much higher) and only 6% of these have been screened for biological activity (Fabricant and Farnsworth, 2001). The bioactive natural compounds stem from the development in terrestrial as well as aquatic organisms of means to produce sophisticated chemical compounds that partake in various interactions among species. These compounds are not directly involved in the maintenance of cells and cell primary metabolism, but are instead believed to have evolved to contribute to the overall fitness of the organism (Qi et al., 2004). The production of such compounds is often referred to as the secondary chemistry of the organism and the compounds themselves are termed secondary metabolites. The role and adaptive significance of secondary metabolites have been under debate for some time (Williams et al., 1989; Stone and Williams, 1992). Traditionally, secondary metabolites have been regarded as evolutionary neutral or waste products. However, the presently most accepted view is that many secondary metabolites are adaptive and play key roles in the host defence against pathogens, parasites, predators, competitors and epibiota, reviewed by (Harper et al., 2001). Although a striking number of secondary metabolites have been discovered from a wide array of organisms, molecules possessing a potent biological activity, i.e. displaying activity in the submicromolar range, are still quite rare (Firn and Jones, 2000). Firn and Jones (2000) recently 11 proposed a model for the evolution of secondary metabolism, which reconciles both secondary metabolites, which display a lack of biological activity and molecules with very potent
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