Anti-inflammatory Compounds from New Zealand Marine Organisms

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(1)Journal of Marine Bioscience and Biotechnology. 2006,. p. 137-143. Vol. 1, No. 3. Review. Anti-inflammatory Compounds from New Zealand Marine Organisms Victoria L. Webb1*, A. Norrie Pearce2 and Elizabeth W. Maas1 1. National Institute of Water and Atmospheric Research (NIWA) Ltd, Private Bag 14-901, Kilbirnie, Wellington, New Zealand Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand. 2. Abstract The market for anti‐inflammatory drugs is large and is expanding rapidly as populations age. Key to the development of new drugs are novel chemotypes. Marine organisms harbour a diverse range of unique compounds with applications in a multitude of disease indications. This review looks at anti‐inflammatory compounds isolated from New Zealand marine organisms. Key words : Anti‐inflammatory, marine environment, new chemical entities, New Zealand. Introduction. The importance of natural compounds as drugs or scaffolds Natural compounds are an important direct and indirect source of compounds for drugs, agrochemicals and other applications. They can be direct in that compounds are directly harvested or synthesised for use, and indirect in that they provide templates or chemical starting points from which other compounds can be derived. A review by Newman et al highlights the importance of the structural novelty found in nature for drug development. For example, figures quoted in their review for the percentage of anti-cancer drugs (new and approved 1981-2002) that are non-synthetic, small molecules, new chemical entities (NCE) is 62%. Similarly they quote for anti-hypertensive drugs, 48 of the 74 formally synthetic drugs can be traced to natural product structures/mimics. For NCE with anti-inflammatory indications, from a total of 50, 13 are described as derived from a natural product but that have usually undergone semi-synthetic modifications [28].. Marine environment verses terrestrial as source of new chemical entities The marine environment lags behind the terrestrial * Corresponding author Phone: +64-4-3860-366, Fax: +64-4-3860-574 E-mail: [email protected]. environment as a source of drugs. Currently several marine derived natural products drugs are in phase I, II or III but have yet to reach the market. See, for example http://www.pharmamar.com/en/pipeline/ for a number of marine derived drugs currently in trials by PharmaMar, a company that specialises in marine derived drug discovery and development. Much of the drug discovery focus has been on the sedentary marine invertebrates but marine molluscs have also shown promise as sources of novel chemical structures, for example, an unusual class of analgesics has been identified in a marine cone snail [30,40] The list of other promising candidates is long and is well covered by a number of reviews including that by John Faulkner and references there-in [13]. In contrast for terrestrial based compounds, Hill reports that around 25% of all drugs currently brought to market in the United States are derived from plant-based sources [16]. It is likely that the trend toward bioprospecting in taxonomically richer marine groups, such as sponges, tunicates, bryozoa, seaweeds and microorganisms, will yield a proportionately increased number of NCE. The contribution of compounds derived from marine micro-organisms is growing. They are increasingly being targeted as sources for novel compounds for the pharmaceutical industry, especially anti cancer drugs; and new.

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(6) 142. 3.. 4.. 5.. 6.. 7.. 8. 9.. 10. 11.. 12.. 13. 14.. 15.. 16.. 17.. WEBB et. al.. V. and Copp, B. R. 2002. Kottamides A-D: Novel Bioactive Imidazolone-Containing Alkaloids from the New Zealand Ascidian Pycnoclavella kottae. J. Org. Chem. 67, 5402 - 5404;. Belofsky, G. N., Anguera, M., Jensen, P. R., Fenical, W. and Kock, M. 2000. Oxepinamides A - C and fumiquinazolines H - I: Bioactive metabolites from a marine isolate of a fungus of the genus Acremonium. Chem. Eur. J. 6, 1355-1360. Bhadury, P., Mohammad, B. T. and Wright, P. C. 2006. The current status of natural products from marine fungi and their potential as anti-infective agents. J. Ind. Microbiol. Biotechnol. 33, 325-337. Blunck, L. 1998. The oceans: state of the marine environment and new trends in international law of the sea. Council of Europe Parliamentary Assembly, Committee on the Environment, Regional Planning and Local Authorities. Report Doc. 8177, 9 September 1998. Bowden, B. F. 2000. Aromatic Alkaloids from Ascidians, In Studies in Natural Products Chemistry: Bioactive Natural Products (Part D) Vol. 23 (Ed. A. U. Rahman), Elsevier Science B.V., pp. 233-283. Casolaro, V., Meliota, S., Marino, O., Patella, V., de Paulis, A., Guidi, G. and Marone, G. 1993. Nimesulide, a sulfonanilide nonsteroidal anti-inflammatory drug, inhibits mediator release from human basophils and mast cells. J. Pharmacol. Exp. Ther. 267, 1375-1385. Class, S. 2002. Pharma Overview Chem. Eng. News 80, 39-49. Das, S., Lyla, P. S. and Khan, S. A. 2006. Marine microbial diversity and ecology: Importance and future perspectives Current Science 90, 1325-1335. Davidson, B. S. 1993. Ascidians: producers of amino acid-derived metabolites. Chem. Rev. 93, 1771 - 1791. Davies, N. M. and Jamali, F. 2004. COX-2 selective inhibitors cardiac toxicity: getting to the heart of the matter. J. Pharm. Pharm. Sci. 7, 332-336. Emelyanov, A., Fedoseev, G., Krasnoschekova, O., Abulimity, A., Trendeleva, T. and Barnes, P. J. 2002. Treatment of asthma with lipid extract of New Zealand green-lipped mussel: a randomised clinical trial. Eur. Respir. J. 20, 596-600. Faulkner, D. J. 2002. Marine natural products Nat. Prod. Rep. 19, 1-48. Ferrandiz, M. L., Sanz, M. J., Bustos, G., Paya, M., Alcaraz, M. J. and De Rosa, S. 1994. Avarol and avarone, two new anti-inflammatory agents of marine origin. Eur. J. Pharmacol. 253, 75-82. Halpern, G. M. 2000. Anti-inflammatory effects of a stabilized lipid extract of Perna canaliculus (Lyprinol). Allerg. Immunol. (Paris). 32, 272-278. Hill, A. B. 1999. Trends in the International Market for Genetic and Biochemical Resources: Opportunities for Columbia. Report presented to the BIOTRADE Columbia Initiative Workshop, Villa de Leyva, Columbia, March 23-25, 1999. Jiang, Z.-D., Jensen, P. R. and Fenical, W. 1999. Lobophorins A and B, new antiinflammatory macrolides. 18.. 19.. 20.. 21.. 22.. 23.. 24.. 25.. 26.. 27.. 28.. 29.. 30.. 31.. produced by a tropical marine bacterium. Bioorg. Med. Chem. Lett. 9, 2003-2006. Keyzers, R. A., Berridge, M. V. and Northcote, P. T. 2003. Clathriol B, a New 14β Marine Sterol from the New Zealand Sponge Clathria lissosclera. Aust. J. Chem. 56, 279-282. Keyzers, R. A. and Davies-Coleman, M. T. 2005. Anti-inflammatory metabolites from marine sponges. Chem. Soc. Rev. 34, 355-365. Keyzers, R. A., Northcote, P. T. and Webb, V. 2002. Clathriol, a novel polyoxygenated 14beta steroid isolated from the New Zealand marine sponge Clathria lissosclera. J. Nat. Prod. 65, 598-600. Keyzers, R. A., Northcote, P. T. and Zubkov, O. A. 2004. Novel Anti-Inflammatory Spongian Diterpenes from the New Zealand Marine Sponge Chelonaplysilla violacea. Eur. J. Org. Chem. 2, 419-425. Look, S. A., Fenical, W., Jacobs, R. S. and Clardy, J. 1986. The pseudopterosins: anti-inflammatory and analgesic natural products from the sea whip Pseudopterogorgia elisabethae. Proc. Natl. Acad. Sci. U S A. 83, 6238-6240. McNamara, C. E., Larsen, L., Perry, N. B., Harper, J. L., Berridge, M. V., Chia, E. W., Kelly, M. and Webb, V. L. 2005. Anti-inflammatory sesquiterpene-quinones from the New Zealand sponge Dysidea cf. cristagalli. J. Nat. Prod. 68, 1431-1433. Miller, T. E. and Ormrod, D. 1980. The anti-inflammatory activity of Perna canaliculus (NZ green lipped mussel). N. Z. Med. J. 92, 187-193. Minale, L., Riccio, R. and Sodano, G. 1974. . Avarol, a Novel Sesquiterpenoid Hydroquinone with a Rearranged Drimane Skeleton from the Sponge. Tet. Lett. 38, 3401-3404. Moore, B. S., Trischman, J. A., Seng, D., Kho, D., Jensen, P. R. and Fenical, W., 1999. Salinamides, antiinflammatory depsipeptides from a marine streptomycete. J. Org. Chem. 64, 1145-1150. Murphy, K. J., Mann, N. J. and Sinclair, A. J. 2003. Fatty acid and sterol composition of frozen and freeze-dried New Zealand Green Lipped Mussel (Perna canaliculus) from three sites in New Zealand. Asia. Pac. J. Clin. Nutr. 12, 50-60. Newman, D. J., Cragg, G. M. and Snader, K. M. 2003. Natural products as sources of new drugs over the period 1981-2002. J. Nat. Prod. 66, 1022-1037. Newman, D. J. and Hill, R. T. 2006. New drugs from marine microbes: the tide is turning. J. Ind. Microbiol. Biotechnol. 33, 539-544. Olivera, B. M., Walker, C., Cartier, G. E., Hooper, D., Santos, A. D., Schoenfeld, R., Shetty, R., Watkins, M., Bandyopadhyay, P. and Hillyard, D. R. 1999. Speciation of cone snails and interspecific hyperdivergence of their venom peptides. Potential evolutionary significance of introns. Ann. N. Y. Acad. Sci. 870, 223-237. Renner, M. K., Jensen, P. R. and Fenical, W. 2000. Mangicols: Structures and biosynthesis of a new class of sesterterpene polyols from a marine fungus of the.

(7) Anti-inflammatory Compounds from New Zealand Marine Organisms. genus Fusarium. J. Org. Chem. 65, 4843-4852. 32. Renner, M. K., Shen, Y. C., Cheng, X. C., Jensen, P. R., Frankmoelle, W., Kauffman, C. A., Fenical, W., Lobkovsky, E. and Clardy, J. 1999. Cyclomarins A-C, New Antiinflammatory Cyclic Peptides Produced by a Marine Bacterium (Streptomyces sp.). J. Am. Chem. Soc. 121, 11273-11276. 33. Schweder, T., Lindequist, U. and Lalk, M. 2005. Screening for new metabolites from marine microorganisms. Adv. Biochem. Eng. Biotechnol. 96, 1-48. 34. Stewart, M., Fell, P. M., Blunt, J. W. and Munro, M. H. G. 1997. Avarol and Related Compounds from the New Zealand Marine Sponge Dysidea sp. Aust. J Chem. 50, 341-348. 35. Sugano, M., Sato, A., Iijima, Y., Furuya, K., Haruyama, H., Yoda, K. and Hata, T. 1994. Phomactins, novel PAF antagonists from marine fungus Phoma sp. J. Org. Chem. 59, 564-569. 36. Sugano, M., Sato, A., Iijima, Y., Oshima, T., Furuya, K., Kuwano, H., Hata, T. and Hanzawa, H. 1991. Phomactin A: A novel PAF antagonist from a marine fungus Phoma sp. J. Am. Chem. Soc. 113, 5463-5464. 37. Tan, A. S. and Berridge, M. V. 2000. Superoxide produced by activated neutrophils efficiently reduces the tetrazolium salt, WST-1 to produce a soluble formazan: a simple colorimetric assay for measuring respiratory burst activation and for screening anti-inflammatory agents. J. Immunol. Methods. 238, 59-68. 38. Tenikoff, D., Murphy, K. J., Le, M., Howe, P. R. and Howarth, G. S. 2005. Lyprinol (stabilised lipid extract of New Zealand green-lipped mussel) : a potential. 39.. 40.. 41.. 42.. 43.. 44.. 143. preventative treatment modality for inflammatory bowel disease. J. Gastroenterol. 40, 361-365. Trischman, J. A., Tapiolas, D. M., Jensen, P. R., Dwight, R., Fenical, W., McKee, T. C., Ireland, C. M., Stout, T. J. and Clardy, J. 1994. Salinamides A and B: Antiinflammatory depsipeptides from a marine streptomycete. J. Am. Chem. Soc. 116, 757-758. Walker, C. S., Steel, D., Jacobsen, R. B., Lirazan, M. B., Cruz, L. J., Hooper, D., Shetty, R., DelaCruz, R. C., Nielsen, J. S., Zhou, L. M., Bandyopadhyay, P., Craig, A. G. and Olivera, B. M. 1999. The T-superfamily of Conotoxins. J. Biol. Chem. 274, 30664-30671. West, L. M., Northcote, P. T. and Batteshill, C. N. 1998. Two New Clerodane Diterpenes from the New Zealand Marine Sponge Raspailia sp. Aust. J. Chem. 51, 10971102. West, L. M., Northcote, P. T., Berridge, M. V. and Alvarez, B. 2000. Anti-inflammatory terpenoids isolated from the New Zealand marine sponge Raspailia topsenti Gordon Research Conference-Marine Natural Products, Ventura, CA, USA, 27 Feb-3 Mar 2000. Whitehouse, M. W., Macrides, T. A., Kalafatis, N., Betts, W. H., Haynes, D. R. and Broadbent, J. 1997. Anti-inflammatory Activity of a Lipid Fraction (Lyprinol) from the NZ Green-lipped Mussel. Inflammopharm 5, 237-246. Zhang, L., An, R., Wang, J., Sun, N., Zhang, S., Hu, J. and Kuai, J. 2005. Exploring novel bioactive compounds from marine microbes. Curr. Opin. Microbiol. 8, 276-281..

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