Vet Med - Czech, 2012, 57(4):177-184 | DOI: 10.17221/5914-VETMED
Biologically active substances from water invertebrates: a review
- 1 Faculty of Fisheries and Protection of Waters, Vodnany, University of South Bohemia in Ceske Budejovice, Czech Republic
- 2 Faculty of Agriculture, University of South Bohemia in Ceske Budejovice, Czech Republic
Some species of invertebrates especially bryozoans (Bryozoa syn. Ectoprocta) and marine sponges (Porifera) are very important sources of pharmacologically exploitable compounds. These substances are probably produced to protect themselves from fish predators and may be an advantage in competition. The real sources of compounds with these antipredatory effects are probably not marine invertebrates themselves, but microscopic symbionts or food which they feed on. Bryostatins from bryozoan species Bugula neritina are produced by a bacterial symbiont called Candidatus Endobugula sertula. They have significant anti-cancer effects, but also other therapeutic benefits. Compounds with the structure of bryostatins were also discovered in some other invertebrates. Sponges are a source of many compounds, e.g., ara-A (vidarabine), manzamine, lasonolides, spongistatins, peloruside and others with antimicrobial, anti-cancer, immunosuppressive and similar activities. Other important sources of compounds with medical effects are tunicates (Tunicata syn. Urochordata) and some snails (Mollusca). One drug was developed from tunicates - Yondelis against refractory soft-tissue sarcomas. Certain other drugs originate from snails: e.g., prialt, which acts against chronic pain in spinal cord injury.
Keywords: bioactive substances; antipredatory effect; competition; bryozoan; bryostatin; Bugula neritina; symbiont; marine sponges; isocyano terpenes; tunicates; snails
Published: April 30, 2012 Show citation
References
- Affeld SH, Waegele S, Avila C, Kehraus, Koenig GM (2007): Distribution of homarine in some Opisthobranchia (Gastropoda: Mollusca). Bonner Zoologische Beitraege 55, 181-190.
- Alvarez P, Ferrari LF, Levine JD (2011): Muscle pain in models of chemotherapy-induced and alcohol-induced peripheral neuropathy. Annals of Neurology 70, 101-109.
Go to original source...
Go to PubMed...
- Ariza ME, Ramakrishnan R, Singh NP, Chauhan A, Nagarkatti PS, Nagarkatti M (2011): Bryostatin-1, a naturally occurring antineoplastic agent, Acts as a Toll-like receptor 4(TLR-4) ligand and induces unique cytokines and chemokines in dendritic cells. Journal of Biological Chemistry 286, 24-34.
Go to original source...
Go to PubMed...
- Chaves-Fonnegra A, Lopez-Victoria M, Parra-Velandia F, Zea S (2005): Chemical ecology of the excavating sponges Cliona aprica, C. caribbaea, C. delitrix and C. tenuis. Boletin de Investigaciones Marinas y Costeras 34, 43-67.
Go to original source...
- Dahms HU, Gao QF, Hwang JS (2007): Optimized maintenance and larval production of the bryozoan Bugula neritina (Bugulidae: Gymnolaemata) in the laboratory. Aquaculture 265, 169-175.
Go to original source...
- Davidson SK, Haygood MK (1999): Identification of sibling species of the bryozoan Bugula neritina that produce different anticancer bryostatins and harbor distinct strains of the bacterial symbiont "Candidatus endobugula sertula". Biological Bulletin 196, 273-280.
Go to original source...
Go to PubMed...
- Davidson SK, Allen SW, Lim GE, Anderson CM, Haygood MG (2001): Evidence for the Biosynthesis of Bryostatins by the Bacterial Symbiont "Candidatus Endobugula sertula" of the Bryozoan Bugula neritina. Applied Environental Microbiology 67, 4531-4537.
Go to original source...
Go to PubMed...
- Debbab A, Aly AH, Proksch P (2011): Bioactive secondary metabolites from endophytes and associated marine derived fungi. Fungal Diversity 49, 1-12.
Go to original source...
- Dunlap WC, Battershill CN, Liptrot CH, Coob RE, Bourne DG, Jaspars M, Long PF, Newman DJ (2007): Biomedicinals from the phytosymbionts of marine invertebrates: A molecular approach. Methods 42, 358-376.
Go to original source...
Go to PubMed...
- Ebada SS, Lin WH, Proksch P (2010): Bioactive sesterterpenes and triterpenes from marine sponges: occurrence and pharmacological significance. Marine Drugs 8, 313-346.
Go to original source...
Go to PubMed...
- Green AP, Lee ATL, Thomas EJ (2011): Total synthesis of a 20-deoxybryostatin. Chemical Communications 47, 7200-7202.
Go to original source...
Go to PubMed...
- Hale KJ, Manaviazar S (2010): New approaches to the total synthesis of the bryostatin antitumor macrolides. Chemistry-An Asian Journal 5, 704-754.
Go to original source...
Go to PubMed...
- Keck GE, Poudel YB, Cummins TJ, Rudra A, Covel JA (2011): Total synthesis of bryostatin 1. Journal of the American Chemical Society 133, 744-747.
Go to original source...
Go to PubMed...
- Kedei N, Telek A, Czap A, Lubart ES, Czifra G, Yang DZ, Chen JQ, Morrison T, Goldsmith PK, Lim LS, Mannan P, Garfield SH, Kraft MB, Li W, Keck GE, Blumberg PM (2011): The synthetic bryostatin analog Merle 23 dissects distinct mechanisms of bryostatin activity in the LNCap human prostate cancer cell line. Biochemical Pharmacology 81, 1296-1308.
Go to original source...
Go to PubMed...
- Kubanek J, Whalen KE, Engel S, Kelly SR, Henkel TP, Fenical W, Pawlik JR (2002): Multiple defensive roles for triterpene glycosides from two Caribbean sponges. Oecologia (Berlin) 131, 125-136.
Go to original source...
Go to PubMed...
- Kuzirian AM, Epstein HT, Gagliardi CJ, Nelson TJ, Sakakibara M, Taylor C, Scioletti AB, Alkon DL (2006): Bryostatin enhancement of memory in Hermissenda. Biological Bulletin 210, 201-214.
Go to original source...
Go to PubMed...
- Laport MS, Santos OCS, Muricy G (2005): Marine sponges: potential sources of new antimicrobial drugs. Current Pharmaceutical Biotechnology 10, 86-105.
Go to original source...
Go to PubMed...
- Lopanik N, Lindquist N, Targett N, (2004a): Potent cytotoxins produced by a microbial symbiont protect host larvae from predation. Oecologia 139, 131-139.
Go to original source...
Go to PubMed...
- Lopanik N, Gufson KR, Lindquist N (2004b): Structure of bryostatin 20: A symbiont-produced chemical defense for larvae of the host bryozoan, Bugula neritina. Journal of Natural Products 67, 1412-1414.
Go to original source...
Go to PubMed...
- Lopanik N, Targett N, Linguist N (2006): Ontogeny of a symbiont-produced chemical defense in Bugula neritina (Bryozoa). Marine Ecology-Progress Series 327, 183-191.
Go to original source...
- Lopez-Abarrategui C, Alba A, Lima LA, Maria-Neto S, Vasconcelos IM, Oliveira JTA, Dias SC, Otero-Gonzalez AJ, Franco OL (2012): Screening of antimicrobials from Caribbean Sea animals and isolation of bactericidal proteins from the littoral mollusk Cenchritis muricatus. Current Microbiology 64, 501-505.
Go to original source...
Go to PubMed...
- Lu Y, Woo SK, Krische MJ (2011): Total synthesis of bryostatin 7 via C-C bond-forming hydrogenation. Journal of the American Chemical Society 133, 13876-13879.
Go to original source...
Go to PubMed...
- Manaviazar S, Hale KJ (2011): Total synthesis of bryostatin 1: A short route. Angewandte-Chemie International Edition 50, 8786-8789.
Go to original source...
Go to PubMed...
- Manning TJ, Land M, Rhodes E, Chamberlin L, Rudloe J, Phillips D, Lam TT, Purcell J, Cooper HJ, Emmett MR, Marshall AG (2005): Identifying bryostatins and potential precursors from the Bugula neritina. Natural Product Research 19, 467-491.
Go to original source...
Go to PubMed...
- Manning TJ, Rhodes E, Land M, Parkman R, Sumner B, Lam TT, Marshall AG, Phillips D (2006): Impact of environmental conditions on the marine natural product bryostatin 1. Natural Product Research 20, 611-628.
Go to original source...
Go to PubMed...
- Mayer AMS, Gustafson KR (2008): Marine pharmacology in 2005-2006: Antitumour and cytotoxic compounds. European Journal of Cancer 44, 2357-2387.
Go to original source...
Go to PubMed...
- McGovern MT, Hellberg HE (2003): Cryptic species, cryptic endosymbionts, and geographical variation in chemical defences in the bryozoan Bugula neritina. Molecular Ecology 12, 1207-1215.
Go to original source...
Go to PubMed...
- Md SH, Fareed S, Ansari S, Khan MS (2012): Marine natural products: A lead for Anti-cancer. Indian Journal of Geo-Marine Sciences 41, 27-39.
- Mehla R, Bivalkar-Mehla S, Zhang R, Handy I, Albrecht H, Giri S, Nagarkatti P, Nagarkatti M, Chauhanet A (2010): Bryostatin modulates latent HIV-1 infection via PKC and AMPK signaling but inhibits acute infection in a receptor independent manner. PLoS ONE 5, 11160.
Go to original source...
Go to PubMed...
- Mendla D (2003): Aquaculture of three phyla of marine invertebrates to yield bioactive metabolites: process developments and economics. Biomolecular Engineering 20, 441-458.
Go to original source...
Go to PubMed...
- Molinski TF, Dalisay DS, Lievens SL, Saludes JP (2009): Drug development from marine natural products. Nature Rewiew Drug Discovery 8, 69-85.
Go to original source...
Go to PubMed...
- Nakagawa-Goto K, Crimmins MT (2011a): Synthetic approaches to the bottom half fragment for bryostatin 11. Synlett 11, 1555-1558.
Go to original source...
- Nakagawa-GotoK, Crimmins MT (2011b): Formal synthesis of the bryostatin northern Hemisphere: asymmetric synthesis of the B Ring and C1-C9 fragment. Synlett 11, 1413-1418.
Go to original source...
- Odintsova NA, Usheva LN, Yakovlev KV, Kiselev KV (2011): Naturally occurring and artificially induced tumor-like formations in marine invertebrates: A search for permanent cell lines. Journal of Experimental Marine Biology and Ecology 407, 241-249.
Go to original source...
- Park Y (2011): Mining invertebrate natural products for future therapeutic treasure. Natural Product Communications 6, 1403-1408.
Go to original source...
Go to PubMed...
- Paul VJ, Arthur K, Ritson-Williams R, Ross C, Kotty S (2007): Chemical defenses: From Compounds to Communities. Biological Bulletin 213, 226-251.
Go to original source...
Go to PubMed...
- Pawlik JR, Chanas B, Toonen RJ, Fenical W (1995): Defenses of Caribbean sponges against predatory reef fish. 1. Chemical Deterrency. Marine Ecology-Progress Series 127, 183-194.
Go to original source...
- Pawlik JR, McFall G, Zea S (2002): Does the odor from sponges of the genus Ircinia protect them from fish predators? Journal of Chemical Ecology 28, 1103-1115.
Go to original source...
Go to PubMed...
- Pettit GR, Cichacz ZA, Gao F, Herold CL, Boyd MR (1993): Isolation and structure of the remarkable human cancer cell-growth inhibitors spongistatin-2 and spongistatin-3 from an eastern Indian ocean Spongia sp. Journal of the Chemical Society - Chemical Communications 14, 1166-1168.
Go to original source...
- Prinsep MR, Yao B, Nicholson BK, Gordon DP (2004): The pterocellins, bioactive alkaloids from the marine bryozoan Pterocella vesiculosa. Phytochemistry Reviews 3, 325-331.
Go to original source...
- Schmidt EW (2005): From chemical structure to environmental biosynthetic pathways: navigating marine invertebrate-bacteria associations. Trends in Biotechnology 23, 437-440.
Go to original source...
Go to PubMed...
- Sharp KH, Davidson SK, Haygood MG (2007): Localization of 'Candidatus Endobugula sertula' and the bryostatins throughout the life cycle of the bryozoan Bugula neritina. Isme Journal 1, 693-702.
Go to original source...
Go to PubMed...
- Sun MK, Alkon DL (2006): Bryostatin-1: Pharmacology and therapeutic potential as a CNS drug. CNS Drug Reviews 12, 1-8.
Go to original source...
Go to PubMed...
- Trindade-Silva AE, Lim-Fong GE, Sharp KH, Haygood MG (2010): Bryostatins: biological context and biotechnological prospects. Current Opinion in Biotechnology 21, 834-842.
Go to original source...
Go to PubMed...
- Wach JY, Gademann K (2012): Reduce to the maximum: truncated natural products as powerful modulators of biological processes. Synlett 163-170.
Go to original source...
- Wender PA, Reuber J (2011): Function oriented synthesis: preparation and initial biological evaluation of new A-ring-modified bryologs. Tetrahedron 67, 9998-10005.
Go to original source...
Go to PubMed...
- Wender PA, Schrier AJ (2011): Total synthesis of bryostatin 9. Journal of the American Chemical Society 133, 9228-9231.
Go to original source...
Go to PubMed...
- Wender PA, Baryza JL, Brenner SE, DeChristopher BA, Loy BA, Schrier AJ, Verma VA (2011): Design, synthesis and evaluation of potent bryostatin analogs that modulate PKC translocation selectivity. Proceedings of the National Academy of Sciences of the United States of America 108, 6721-6726.
Go to original source...
Go to PubMed...
- Winston JE, Woollacott RM (2008): Redescription and revision of some red-pigmented Bugula species. Bulletin of the Museum of Comparative Zoology 159, 179-212.
Go to original source...
- Zhu JB, Wan XY, Zhu YP, Ma XL, Zheng YW, Zhang TB (2010): Toxicity of bryostatin-1 on the embryo-fetal development of Sprague-Dawley Rats. Birth Defects Research part B - Developmental and Reproductive Toxicology 89, 171-174.
Go to original source...
Go to PubMed...
- Zohar O, Lavy R, Zi XM, Nelson TJ, Hongpaisan J, Pick CG, Alkon DL (2011): PKC activator therapeutic for mild traumatic brain injury in mice. Neurobilogy of Disease 41, 329-337.
Go to original source...
Go to PubMed...
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