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Review Article

Marine natural product drug discovery: Leads for treatment of inflammation, cancer, infections, and neurological disorders

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Pages 228-237 | Received 30 Jul 2009, Accepted 29 Aug 2009, Published online: 05 May 2010

References

  • Cragg GM, Newman DJ. Chemical diversity: a function of biodiversity. Trends Pharmacol Sci 2002;23: 404–405.
  • Cragg GM, Grothaus PG, Newman DJ. Impact of natural products on developing new anti-cancer agents. Chem Rev ACS ASAP 2009;109(7):3012–43.
  • Mantovani A, Allavena P, Sica A, Balkwill F. Cancer-related inflammation. Nature 2008;454 (7203): 436–444.
  • Villoslada P, Moreno B, Melero I, Pablos JL, Martino G, Uccelli A, et al. Immunotherapy for neurological diseases. Clin Immunol 2008;128 (3): 294–305.
  • Strangman WK, Kwon HC, Broide D, Jensen PR, Fenical W. Potent inhibitors of pro-inflammatory cytokine production produced by a marine-derived bacterium. J Medicl Chem 2009;52(8): 2317–2327.
  • Renner MK, Shen YC, Cheng XC, Jensen PR, Frankmoelle W, Kauffman CA, et al.Cyclomarins A-C, new antiinflammatory cyclic peptides produced by a marine bacterium (Streptomyces sp.). J Am Chem Soc 1999;121 (49): 11273–11276.
  • Edwards DJ, Marquez BL, Nogle LM, McPhail K, Goeger DE, Roberts MA, et al. Structure and biosynthesis of the jamaicamides, new mixed polyketide-peptide neurotoxins from the marine cyanobacterium Lyngbya majuscula. Chem Biol 2004;11 (6): 817–833.
  • Gerwick WH, Proteau PJ, Nagle DG, Hamel E, Blokhin A, Slate DL. Structure of curacin-A, a novel antimitotic, antiproliferative, and brine shrimp toxic natural product from the marine cyanobacterium Lyngbya-majuscula. J Organ Chem 1994;59 (6): 1243–1245.
  • Gerwick WH, Tan LT, Sitachitta N. Nitrogen-containing metabolites from marine cyanobacteria. Alkaloids Chem Biol 2001;57: 75–184.
  • Tidgewell K, Clark BR, Gerwick WH. The natural products chemistry of cyanobacteria. In comprehensive natural products chemistry, 2nd ed., Moore B, Crews P, eds. Oxford, UK: Elsevier, 2009; in press.
  • Fenical W, Jensen PR. Developing a new resource for drug discovery: Marine actinomycete bacteria. Nat Chem Biol 2006;2 (12): 666–673.
  • Beck PL, Wallace JL. Cytokines in inflammatory bowel disease. Mediat Inflamm 1997;6 (2): 95–103.
  • Carroll G, Bell M, Wang H, Chapman H, Mills J. Antagonism of the Il-6 cytokine subfamily - a potential strategy for more effective therapy in rheumatoid arthritis. Inflammat Res 1998;47 (1): 1–7.
  • Norrby-Teglund A, Stevens DL. Novel therapies in streptococcal toxic shock syndrome: Attenuation of virulence factor expression and modulation of the host response. Curr Opin Infect Dis 1998;11 (3): 285–291.
  • MacMicking J, Xie QW, Nathan C. Nitric oxide and macrophage function. Annu RevImmunol 1997;15: 323–350.
  • Martel-Pelletier J. Pathophysiology of osteoarthritis. Osteoarth Cartilage 1998;6 (6): 374–376.
  • Abad MJ, Bedoya LM, Bermejo P. Natural marine anti-inflammatory products. Mini-Rev Med Chem 2008;8 (8): 740–754.
  • Zhang LH, Longley RE, Koehn FE. Antiproliferative and immunosuppressive properties of microcolin A, a marine-derived lipopeptide. Life Sci 1997;60 (10): 751–762.
  • Takamatsu S, Nagle DG, Gerwick WH. Secondary metabolites from marine cyanobacteria and algae inhibit LFA-1/ICAM-1 mediated cell adhesion. Planta Med 2004;70 (2): 127–131.
  • Stevenson CS, Capper EA, Roshak AK, Marquez B, Eichman C, Jackson JR, Mattern M et al. The identification and characterization of the marine natural product scytonemin as a novel antiproliferative pharmacophore. J Pharmacol Exp Ther 2002;303 (2): 858–866.
  • Blumberg PM, Acs G, Acs P, Areces LB, Kazanietz MG, Lewin NE, Szallasi Z. Protein kinase C in cell signaling: strategies for the development of selective inhibitors. Agents Actions Suppl 1995;47: 87–100.
  • Stevenson CS, Capper EA, Roshak AK, Marquez B, Grace K, Gerwick WH, et al. Scytonemin - a marine natural product inhibitor of kinases key in hyperproliferative inflammatory diseases. Inflammat Res 2002;51 (2): 112–114.
  • Appleton DR, Sewell MA, Berridge MV, Copp BR. A new biologically active malyngamide from a New Zealand collection of the sea hare Bursatella leachii. J Natural Prods 2002;65 (4): 630–631.
  • Romay C, Armesto J, Remirez D, Gonzalez R, Ledon N, Garcia I. Antioxidant and anti-inflammatory properties of C-phycocyanin from blue-green algae. Inflammat Res 1998;47 (1): 36–41.
  • Remirez D, Gonzalez R, Merino N, Rodriguez S, Ancheta O. Inhibitory effects of Spirulina in zymosan-induced arthritis in mice. Mediat Inflamm 2002;11 (2): 75–79.
  • Garbacki N, Gloaguen V, Damas J, Hoffmann L, Tits M, Angenot L. Inhibition of croton oil-induced oedema in mice ear skin by capsular polysaccharides from cyanobacteria. Naunyn-Schmiedebergs Arch Pharmacol 2000;361 (4): 460–464.
  • Guzman S, Gato A, Lamela M, Freire-Garabal M, Calleja JM. Anti-inflammatory and immunomodulatory activities of polysaccharide from Chlorella stigmatophora and Phaeodactylum tricomutum. Phytother Res 2003;17 (6): 665–670.
  • Park YK, Rasmussen HE, Ehlers SJ, Blobaum KR, Lu F, Schlegal VL, et al. Repression of proinflammatory gene expression by lipid extract of Nostoc commune var sphaeroides kutzing, a blue-green alga, via inhibition of nuclear factor-kappa B in raw 264.7 macrophages. Nutr Res 2008;28 (2): 83–91.
  • Carter NJ, Keam, SJ. Trabectedin: A review of its use in the management of soft tissue sarcoma and ovarian cancer. Drugs 2007;67 (15): 2257–2276.
  • Hallock YF, Cragg GM. National cooperative drug discovery groups (ncddgs): A successful model for public private partnerships in cancer drug discovery; Swets Zeitlinger Publishers, 2003;78–91.
  • Feling RH, Buchanan GO, Mincer TJ, Kauffman CA, Jensen PR, Fenical W. Salinosporamide A. a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus salinospora. Angew. Chem Int Ed Engl 2003;42 (3):355–357.
  • Twombly R. First proteasome inhibitor approved for multiple myeloma. J NCI 2003, 95(12): 845.
  • Williams PG. Panning for chemical gold: marine bacteria as a source of new therapeutics. Trends Biotech 2009;27: 45–52.
  • Pettit GR, Kamano Y, Herald CL, Tuinman AA, Boettner FE, Kizu H, et al. The isolation and structure of a remarkable marine animal antineoplastic constituent: dolastatin 10. J Am Chem Soc 1987;109 (22): 6883–6885.
  • Bai R, Pettit GR, Hamel E. Binding of dolastatin 10 to tubulin at a distinct site for peptide antimitotic agents near the exchangeable nucleotide and vinca alkaloid sites. J Biol Chem 1990;265 (18):17141–17149.
  • Pitot HC, McElroy EA, Reid JM, Windebank AJ, Sloan JA, Erlichman C, et al. Phase I trial of dolastatin-10 (nsc 376128) in patients with advanced solid tumors. Clin Cancer Res 1999;5 (3):525–31.
  • Vaishampayan U, Glode M, Du W, Kraft A, Hudes G, Wright J, et al. Phase II study of dolastatin 10 in patients with hormone-refractory metastatic prostate adenocarcinoma. Clin Cancer Res 2000;6 (11): 4205–4208.
  • Hoffman M, Blessing J, Lentz S. A phase II Trial of dolastatin-10 in recurrent platinum-sensitive ovarian carcinoma: a Gynecologic Oncology Group study. Gynecol Oncol 2003;89 (1): 95–98.
  • Miyazaki K, Kobayashi M, Natsume T, Gondo M, Mikami T, Sakakibara K, et al. Synthesis and antitumor activity of novel dolastatin 10 analogs. Chem Pharma Bull 1995;43 (10):1706–1718.
  • Nogle LM, Gerwick WH. Somocystinamide A, a novel cytotoxic disulfide dimer from a Fijian marine cyanobacterial mixed assemblage. Org Lett 2002;4 (7):1095–1098.
  • Barnhart BC, Legembre P, Pietras E, Bubici C, Franzoso G, Peter ME. CD95 ligand induces motility and invasiveness of apoptosis-resistant tumor cells. EMBO J 2004;23(15):3175–85.
  • Wrasidlo W, Mielgo A, Torres VA, Barbero S, Stoletov K, Suyama TL, et al. The marine lipopeptide somocystinamide A triggers apoptosis via caspase 8. Proc. Natl Acad Sci U S A 2008;105 (7): 2313–2318.
  • Suyama TL, Gerwick WH. Stereospecific total synthesis of somocystinamide A. Org Lett 2008;10 (20): 4449–4452.
  • Medina RA, Goeger DE, Hills P, Mooberry SL, Huang N, Romero LI, et al. Coibamide A, a potent antiproliferative cyclic depsipeptide from the Panamanian marine cyanobacterium Leptolyngbya sp. J Am Chem Soc 2008;130 (20): 6324.
  • Kresse H, Belsey Mark J, Rovini H. The antibacterial drugs market. Nat Rev Drug Discovery 2007;6 (1): 19–20.
  • Katz ML, Mueller LV, Polyakov M, Weinstock SF. Where have all the antibiotic patents gone? Nat Biotechnol 2006;24 (12): 1529–1531.
  • Clardy J, Fischbach MA, Walsh CT. New antibiotics from bacterial natural products. Nat Biotechnol 2006;24 (12): 1541–1550.
  • Jayaraman A, Wood TK. Bacterial quorum sensing: signals, circuits, and implications for biofilms and disease. Annu Rev Biomed Eng 2008;10: 145–167.
  • Miller MB, Bassler BL. Quorum sensing in bacteria. Annu Rev Microbiol 2001;55 (1): 165–199.
  • Skindersoe ME, Ettinger-Epstein P, Rasmussen TB, Bjarnsholt T, de Nys R, Givskov M. Quorum sensing antagonism from marine organisms. Mar Biotechnol 2008;10 (1): 56–63.
  • Lombardo D, Dennis EA. Cobra venom phospholipase A2 inhibition by manoalide. A novel type of phospholipase inhibitor. J Biol Chem., 1985;260 (12): 7234–7240.
  • Givskov M, de Nys R, Manefield M;, Gram L, Maximilien R, Eberl L, et al. Eukaryotic interference with homoserine lactone-mediated D prokaryotic signalling. J Bacteriol 1996;178 (22): 6618–6622.
  • Cueto M, Jensen PR, Kauffman C, Fenical W, Lobkovsky E, Clardy J. Pestalone, a new antibiotic produced by a marine fungus in response to bacterial challenge. J Nat Prod 2001;64 (11): 1444–1446.
  • Carmichael WW. Cyanobacteria secondary metabolites - the cyanotoxins. J Appl Bacteriol 1992;72 (6): 445–459.
  • Carmichael W. W. Toxins of cyanobacteria. Sci Am. 1994;270 (1): 78–86.
  • Ouellette AJA, Wilhelm SW. Toxic cyanobacteria: the evolving molecular toolbox. Front Ecol Environ 2003;1 (7): 359–366.
  • Simpson DM, Gracies JM, Graham HK, Miyasaki, JM, Naumann M, Russman B, et al. Assessment: botulinum neurotoxin for the treatment of spasticity (an evidence-based review). Report of the Therapeutics and Technology Assessment Subcommittee of the American Academy of Neurology. Neurology 2008;70 (19):1691–1698.
  • Trung NP, Fitches E, Gatehouse JA. A fusion protein containing a lepidopteran-specific toxin from the South Indian red scorpion (Mesobuthus tamulus) and snowdrop lectin shows oral toxicity to target insects. BMC Biotechnol 2006;6:18.
  • Singh S, Kate BN, Banerjee UC. Bioactive compounds from cyanobacteria and microalgae: an overview. Crit Rev Biotechnol 2005;25 (3): 73–95.
  • LePage KT, Goeger D, Yokokawa F, Asano T, Shioiri T, Gerwick W. H, et al.The neurotoxic lipopeptide kalkitoxin interacts with voltage-sensitive sodium channels in cerebellar granule neurons. ToxicolLetts 2005;158 (2): 133–139.
  • Wu M, Okino T, Nogle LM, Marquez BL, Williamson RT, Sitachitta N, et al. Structure, synthesis, and biological properties of kalkitoxin, a novel neurotoxin from the marine cyanobacterium Lyngbya majuscula. J Am Chem Soc 2000;122 (48): 12041–12042.
  • Li WI, Berman FW, Okino T, Yokokawa F, Shioiri T, Gerwick W. H, et al.Antillatoxin is a marine cyanobacterial toxin that potently activates voltage-gated sodium channels. Proc Natl Acad Sci U S A 2001;98 (13): 7599–7604.
  • Chang ZX, Flatt P, Gerwick WH, Nguyen VA, Willis CL, Sherman DH. The barbamide biosynthetic gene cluster: A novel marine cyanobacterial system of mixed polyketide synthase (PKS)-non-ribosomal peptide synthetase (NRPS) origin involving an unusual trichloroleucyl starter unit. Gene 2002;296 (1–2): 235–247.
  • Shimizu Y. Microalgal metabolites. Curr Opin Microbiol 2003;6 (3): 236–243.
  • Flatt PM, O’Connell SJ, McPhail KL, Zeller G, Willis CL, Sherman DH, et al. Characterization of the initial enzymatic steps of barbamide biosynthesis. J Natural Prod. 2006;69 (6): 938–944.
  • Galonic DP, Vaillancourt FH, Walsh CT. Halogenation of unactivated carbon centers in natural product biosynthesis: Trichlorination of leucine during barbamide biosynthesis. J Am Chem Soc 2006;128 (12): 3900–3901.
  • Dawson R. M. The toxicology of microcystins. Toxicon 1998;36 (7): 953–962.
  • Rao, PVL, Gupta N, Bhaskar ASB, Jayaraj R. Toxins and bioactive compounds from cyanobacteria and their implications on human health. J Environ Biol 2002;23 (3): 215–224.
  • Gulledge BM, Aggen JB, Huang HB, Nairn AC, Chamberlin AR. The microcystins and nodularins: Cyclic polypeptide inhibitors of PP1 and PP2A. Curr Med Chem 2002;9 (22): 1991–2003.
  • Hitzfeld BC, Hoger SJ, Dietrich DR. Cyanobacterial toxins: Removal during drinking water treatment, and human risk assessment. Environ Health Perspect 2000;108: 113–122.
  • Harada K. Recent advances of toxic cyanobacteria researches. J Health Sci 1999;45 (3): 150–165.
  • Falconer IR. In An overview of problems caused by toxic blue-green algae (cyanobacteria) in drinking and recreational water. New York: John Wiley & Sons Inc, 1999; pp. 5–12.
  • Harada K, Ogawa K, Matsuura K, Murata H, Suzuki M, Watanabe M.F, et al.. Structural determination of geometrical-isomers of microcystins LR and RR from cyanobacteria by 2-dimensional NMR spectroscopic techniques. Chem Res Toxicol 1990;3 (5): 473–481.
  • Rudolphbohner S, Mierke DF, Moroder L. Molecular-structure of the cyanobacterial tumor-promoting microcystins. FEBS Lett 1994;349 (3): 319–323.
  • An JS, Carmichael WW. Use of a colorimetric protein phosphatase inhibition assay and enzyme-linked-immunosorbent-assay for the study of microcystins and nodularins. Toxicon 1994;32 (12): 1495–1507.
  • Matsushima R, Yoshizawa S, Watanabe MF, Harada K, Furusawa M, Carmichael WW, et al. In vitro and in vivo effects of protein phosphatase inhibitors, microcystins and nodularin, on mouse skin and fibroblasts. Biochem Biophys Res Commun 1990;171 (2): 867–874.
  • Yoshizawa S, Matsushima R, Watanabe MF, Harada K, Ichihara A, Carmichael WW, et al. Inhibition of protein phosphatases by Microcystis and Nodularin associated with hepatotoxicity. J Cancer Res Clin Oncol 1990;116 (6): 609–614.
  • Cohen P. The structure and regulation of protein phosphatases. Annu Rev Biochem 1989;58: 453–508.
  • Hunter T. Protein-kinases and phosphatases - the yin and yang of protein-phosphorylation and signaling. Cell 1995;80 (2): 225–236.
  • Agrawal MK, Zitt A, Bagchi D, Weckesser J, Bagchi SN, von Elert E. In Characterization of proteases in guts of Daphnia magna and their inhibition by Microcystis aeruginosa pcc 7806. New York: John Wiley & Sons Inc, 2005; pp. 314–322.
  • Agrawal MK, Bagchi D, Bagchi SN. Acute inhibition of protease and suppression of growth in zooplankter, Moina macrocopa, by Microcystis blooms collected in Central India. Hydrobiologia 2001;464 (1–3): 37–44.
  • Codd GA, Morrison LF, Metcalf JS. Cyanobacterial toxins: risk management for health protection. Toxicol Appl Pharmacol 2005;203 (3): 264–272.
  • Namikoshi M, Rinehart KL. Bioactive compounds produced by cyanobacteria. J Ind Microbiol Biotechnol 1996, 17 (5–6): 373–384.
  • Mansell HL. Synthetic approaches to anatoxin-A. Tetrahedron 1996;52 (17): 6025–6061.
  • Koskinen AMP, Rapoport H. Synthetic and conformational studies on anatoxin-A - a potent acetylcholine agonist. J Med Chem 1985;28 (9): 1301–1309.
  • Devlin JP, Edwards OE, Gorham PR, Hunter NR, Pike RK, Stavric B. Anatoxin-A, a toxic alkaloid from Anabaena-flos-aquae NRC-44H. Can J Chem Rev Can Chim 1977;55 (8): 1367–1371.
  • Mahmood NA, Carmichael WW. Anatoxin-A(s), an anticholinesterase from the cyanobacterium Anabaena-flos-aquae NRC-525-17. Toxicon 1987;25 (11): 1221–1227.
  • Mahmood NA, Carmichael WW, Pfahler D. Anticholinesterase poisonings in dogs from a cyanobacterial (blue-green-algae) bloom dominated by Anabaena-flos-aquae. Am J Vet Res 1988;49 (4): 500–503.
  • Cook WO, Beasley VR, Dahlem AM, Dellinger JA, Harlin KS, Carmichael WW. Comparison of effects of anatoxin-A(s) and paraoxon, physostigmine and pyridostigmine on mouse-brain cholinesterase activity. Toxicon 1988;26 (8): 750–753.
  • Moore BS, Ohtani I, Dekoning CB, Moore RE, Carmichael WW. Biosynthesis of anatoxin-A(s) - origin of the carbons. Tetrahedron Lett 1992;33 (44): 6595–6598.
  • Bordner J, Thiessen WE, Bates HA, Rapoport H. Structure of a crystalline derivative of saxitoxin - structure of saxitoxin. J Am Chem Soc 1975;97 (21): 6008–6012.
  • Wong JL, Oesterli R, Rapoport H. Structure of saxitoxin. J Am Chem Soc 1971;93 (26): 7344.
  • Schantz EJ, Lynch JM, Vayvada G, Matsumot K, Rapoport H. Purification and characterization of poison produced by Gonyaulax catenella in Axenic culture. Biochemistry 1966;5 (4): 1191.
  • Jackim E, Gentile J. Toxins of a blue-green alga—similarity to saxitoxin. Science 1968;162 (3856): 915.
  • Kao CY, Nishiyama A. Actions of saxitoxin on peripheral neuromuscular systems. J Physiol -London 1965;180 (1): 50.
  • Oshima Y, Buckley LJ, Alam M, Shimizu Y. Heterogeneity of paralytic shellfish poisons - 3 new toxins from cultured Gonyaulax-tamarensis cells, Mya-aren aria and Saxidomus-giganteus. Comp Biochem Physiol C-Pharmacol Toxicol Endocrinol 1977;57 (1): 31–34.
  • Watkins SM, Reich A, Fleming LE, Hammond, R. Neurotoxic shellfish poisoning. Mar Drugs 2008;6 (3):431–55.
  • Lin Y, Risk M, Ray SM, Van Engen D, Clardy J, Golik J et al. Isolation and structure of brevetoxin B from the “red tide” dinoflagellate Gymnodinium breve. J Am Chem Soc 1981;103 (22): 6773.
  • Gawley RE, Rein KS, Kinoshita M, Baden DG. Binding of brevetoxins and ciguatoxin to the voltage-sensitive sodium channel and conformational analysis of brevetoxin B Toxicon 1992;30 (7):780–785.
  • George J, Dravid SM, Prakash A, Xie J, Peterson J, Jabba SV, et al.Sodium channel activation augments NMDA receptor function and promotes neurite outgrowth in immature cerebrocortical neurons. J Neurosci 2009;29 (10): 3288–301.
  • Bourdelais AJ, Campbell S, Jacocks H, Naar J, Wright JLC, Carsi J, et al.Brevenal is a natural inhibitor of brevetoxin action in sodium channel receptor binding assays: Honoring John William Daly, Part II. CellMolecul Neurobiol. 2004;24 (4): 553–563.
  • Weise G, Drews G, Jann B, Jann K. Identification and analysis of a lipopolysaccharide in cell walls of blue-green alga Anacystis-nidulans. Archiv Fur Mikrobiologie 1970;71 (1): 89.
  • Weckesser J, Drews G, Mayer H. Lipopolysaccharides of photosynthetic prokaryotes. Annu Rev Microbiol 1979;33: 215–239.
  • Keleti G, Sykora JL. Production and properties of cyanobacterial endotoxins. Appl Environ Microbiol 1982;43 (1): 104–109.
  • Codd GA. Toxins of fresh-water cyanobacteria. Microbioll Sciences 1984;1 (2): 48–52.
  • Stewart I, Schluter PJ, Shaw GR. Cyanobacterial lipopolysaccharides and human health—a review. Environ Health 2006;5 (7): 1–23.

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