Marine sponges as a source of new bioactive substances
Main Article Content
Abstract
Marine sponges (Porifera) have drawn the attention from a broad number of researchers all over the world. These animals and their simbionts are specialized in chemical warfare, producing biologically active chemical substances as an effective defense against predators. They have been considered a goldmine to chemists, from which have been discovered more than 6000 novel structures; many of them, with enormous biomedical applications, mainly against cancer, but also against bacteria, viruses and other diseases. Some of the sponge-derived drugs are available in the market, such as: Ara-A (antiviral) and Ara-C (anticancer), but there are diverse bioactive compounds under clinical trials. In Cuba, the researches related to the isolation of compounds from marine sponges are scarce and the initial studies were about pharmacological evaluations of extracts and fractions. In recent studies, three sponges were investigated (Agelas cerebrum, Niphates digitalis and Pandaros acanthifolium), from which were isolated and identified 45 metabolites, two of them were isolated for the first time as natural products, including the discovery of 30 novel metabolites, dividing in two new families of steroidal saponins with uncommon chemical characteristics and potential against several parasitic protozoa and tumor human cell lines.
Article Details
How to Cite
RegaladoE. L., LagunaA., & MartínezJ. R. (2020). Marine sponges as a source of new bioactive substances. Cub@: Medio Ambiente Y Desarrollo, 10(19). Retrieved from https://cmad.ama.cu/index.php/cmad/article/view/152
Section
Original Article
References
Anderson, H. J.; Coleman, J. E.; Andersen, R. J.; Roberge, M. 1997. Cytotoxic peptides hemiasterlin, hemiasterlin A, and hemiasterlin B include mitotic arrest and abnormal spindle formation. Cancer Chemotherapy and Pharmacology 39: 223-226.
Aneiros, A.; Garateix, A.; García, T.; Palmero, A.; Valdés, A; Arteaga, F; Cuquerella, E. 2000. Informe Final del Proyecto No. 004-03-216 .Resultado 02 “ Evaluación de nuevas sustancias de origen marino con potencialidades como biofármacos”, Archivos del PNCT “Desarrollo de Productos Biotecnológicos, Farmacéuticos y de Medicina Verde”.
Aneiros, A.; Garateix, A.; García, T.; Palmero, A.; Valdés, A; Arteaga, F; Cuquerella, E. 2002. Informe Final del Proyecto “Obtención de nuevos compuestos de origen marino de aplicación en biomedicina“ No.067 Resultado 02 Archivos de la Agencia de Medio Ambiente, CITMA.
Bergmann, W.; Feeney, R. J. 1950. The isolation of a new thymine pentoside from sponges. Journal of the American Chemical Society 72: 2809-2810.
Bergmann, W.; Feeney, R. J. 1951. Constributions to the study of marine products. XXXII. The nucleosides of sponges. Journal of Organic Chemistry 16: 981-987.
Bergmann, W.; Burke, D. C. 1955. The nucleosides of sponges. 3. Spongothymidine and spongouridine (from Cryptotethia crypta). Journal of Organic Chemistry 20: 1501-1507.
Bergquist, P. R., Sponges. Hutchinson University library: Londres, 1978; 268 pages.
Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. 2005. Marine natural products. Natural Product Reports 20: 15-61.
Blunt, J. W.; Copp, B. R.; Hu, W.-P.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. 2007. Marine natural products. Natural Product Reports 24: 31-86.
Blunt, J. W.; Copp, B. R.; Hu, W.-P.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. 2008. Marine natural products (A review). Natural Product Reports 25 (1): 35-94.
Bramley, A. M.; Langlands, J. M.; Jones, A. K.; Burgoyne, D. L.; Li, Y.; Andersen, R. J.; Salari, H. 1995. Effects of IZP-94005 (contignasterol) on antigen-induced bronchial responsiveness in ovalbuminsensitized guinea-pigs. British Journal of Pharmacology 115: 1433-1438.
Bubb, M. R.; Senderowicz, A. M. J.; Sausville, E. A.; Duncan, K. L. K.; Korn, E. D. 1994. Jasplakinolide, a cytotoxic natural product, induces actin polymerization and competitively inhibits the binding of phalloidin to F-actin. Journal of Biological Chemistry 269: 14869-14871.
Burgoyne, D. L.; Andersen, R. J. 1992. Contignasterol, a highly oxygenated steroid with the “unnatural” 14 β configuration from the marine sponge Petrosia contignata Thiele, 1899. Journal of Organic Chemistry 57: 525-528.
Cachet, N.; Regalado, E. L.; Genta-Jouve, G.; Mehiri, M.; Amade, P.; Thomas, O. P. 2009. Steroidal glycosides from the marine sponge Pandaros acanthifolium. Steroids 74: 746-750.
Coleman, J. E.; de Silva, E. D.; Kong, F.; Andersen, R. J.; Allen, T. M. 1995. Cytotoxic peptides from the marine sponge Cymbastela sp. Tetrahedron 51: 10653-10662.
Corredor, J. E.; Wilkinson, C. R.; Vicente, V. P.; Morrel, J. M.; Otero, E. 1988. Nitrate release by Caribbeean reef sponges. Limnology and Oceanography 33 (1): 114-120.
El Sayed, K. A.; Kelly, M.; Kara, U. A. K.; Ang, K.; Katsuyama, I.; Dunbar, D. C.; Khan, A. A.; Hamman, M. T. 2001. New manzamines alkaloids with potent activity against infectious diseases. Journal of the American Chemical Society 123 (9): 1804-1808.
Gamble, W. R.; Durso, N. A.; Fuller, R. W.; Westergaard, C. K.; Johnson, T. R.; Sackett, D. L.; Hamel, E.; Cardellina, J. H.; Boyd, M. R. 1999. Cytotoxic and tubulin-interactive hemiasterlins from Auletta sp and Siphonochalina sp sponges. Bioorganic & Medicinal Chemistry 7: 1611-1615.
Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. 1990. Discodermolide: a new bioactive polyhydroxylated lactone from the marine sponge Discodermia dissoluta. Journal of Organic Chemistry 55: 4912-4915.
Hirata, Y.; Uemura, D. 1986. Halichondrins-antitumor polyether macrolides from a marine sponge. Pure and Applied Chemistry 58: 701-710.
Iijima, H.; Kimura, K.; Sakai, T.; Uchimura, A.; Shimizu, T.; Ueno, H.; Natori, T.; Koezuka, Y. 1998. Structure-activity relationship and conformational analysis of monoglycosylceramides on the syngeneic mixed leukocyte reaction. Bioorganic & Medicinal Chemistry 6: 1905-1910.
Jain, R.; Tiwari, A. 2007. Sponges: An invertebrate of bioactive potential. Current Science 93: 444-445.
Kobayashi, E.; Motoki, K.; Uchida, T.; Fukushima, H.; Koezuka, Y. 1995. KRN7000, a novel immunomodulator, and its antitumor activities. Oncology Research 7: 529-534.
Kuznetsov, G.; Towle, M. J.; Cheng, H.; Kawamura, T.; TenDyke, K.; Liu, D.; Kishi, Y.; Yu, M. J.; Littlefield, B. A. 2004. Induction of morphological and biochemical apoptosis following prolonged mitotic blockage by halichondrin B macrocyclic ketone analog E7389. Cancer Research 64: 5760-5766.
Loganzo, F.; Discafani, C. M.; Annable, T.; Beyer, C.; Musto, S.; Hari, M.; Tan, X.; Hardy, C.; Hernandez, R.; Baxter, M.; Singanallore, T.; Khafizova, G.; Poruchynsky, M. S.; Fojo, T.; Nieman, J. A.; Ayral-Kaloustian, S.; Zask, A.; Andersen, R. J.; Greenberger, L. M. 2003. HTI-286, a synthetic analogue of the tripeptide hemiasterlin, is a potent antimicrotubule agent that circumvents P-Glycoprotein-mediated resistance in vitro and in vivo. Cancer Research 63: 1838-1845.
Mayer, A. M.; Rodriguez, A. D.; Berlinck, R. G.; Hamann, M. T. 2007. Marine pharmacology in 2003–4: Marine compounds with anthelmintic, antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiplatelet, antiprotozoal, antituberculosis, and antiviral activities; affecting the cardiovascular, immune, and nervous systems and other miscellaneous mechanisms of action. Comparative Biochemistry and Physiology, C: Comparative Pharmacology and Toxicology 145: 553-581.
Mayer, A. M.; Rodriguez, A. D.; Berlinck, R. G.; Hamann, M. T. 2009. Marine pharmacology in 2005–6: Marine compounds with anthelmintic, antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiprotozoal, antituberculosis, and antiviral activities; affecting the cardiovascular, immune, and nervous systems and other miscellaneous mechanisms of action. Biochimica et Biophysica Acta 1790: 283-308.
Mayer, A. M. S.; Hamann, M. T. 2002. Marine compounds with anthelmintic, antibacterial, anticoagulant, antidiabetic, antifungal, anti-inflammatory, antimalarial, antiplatelet, antiprotozoal, and antiviral activities; affecting the cardiovascular, immune, and nervous systems and other miscellaneous mechanisms of action. Comparative Biochemistry and Physiology, C: Comparative Pharmacology and Toxicology 140: 265-286.
Munro, M. H. G.; Blunt, J. W., Marine Literatura DataBase (MarinLit), University de Canterbury, New Zealand, 2009.
Natori, T.; Y., K.; Higa, T. 1993. Agelasphins, novel alpha-galactosylceramides from the marine sponge Agelas mauritianus. Tetrahedron Letters 34: 5591-5592.
Natori, T.; Morita, M.; K., A.; Koezuka, Y. 1994. Agelasphins, novel antitumor and immunostimulatory cerebrosides from the marine sponge Agelas mauritianus. Tetrahedron 50: 2771-2784.
Orhan, I.; Şener, B.; Kaiser, M.; Brun, R.; Tasdemir, D. 2010. Inhibitory activity of marine sponge-derived natural products against parasitic Protozoa. Marine Drugs 5: 47-58.
Paterson, I.; Lyothier, I. 2004. Total synthesis of (+)-discodermolide: an improved endgame exploiting a Still-Gennari-type olefination with a C1-C8 b-ketophosphonate Fragment. Organic Letters 6: 4933-4936.
Rao, K. V.; Santarsiero, B. D.; Mesecar, A. D.; Schinazi, R. F.; Tezwani, B. L.; Hamman, M. T. 2003. New manzamine alkaloids with activity agains infectious and tropical parasitic diseases from an Indonesian sponge. Journal of Natural Products 66 (6): 823-828.
Rao, K. V.; Kasanah, N.; Wahyuono, S.; Tekwani, B. L.; Schinazi, R. F.; Hamman, M. T. 2004. Three new manzamine alkaloids from a common Indonesian sponge and their activity against infectious and tropical parasitic diseases. Journal of Natural Products 67 (8): 1314-1318.
Rao, K. V.; Donia, M. S.; Peng, J. N.; García-Palomero, E.; Alonso, D.; Martínez, A.; Medina, M.; Franzblau, S. G.; Tekwani, B. L.; Khan, S. I.; Wahyuono, S.; Willett, K. L.; Hamann, M. T. 2006. Manzamine B and E and ircinal A related alkaloids from an Indonesian Achanthostrongylophora sponge and their activity against infectious, tropical parasitic, and Alzheimer´s diseases. Journal of Natural Products 69 (7): 1034-1040.
Rayl, A. J. S. 1999. Oceans: medicine chests of the future? The Scientist 13: 1.
Regalado, E. L. 2010a. Aislamiento e identificación de metabolitos bioactivos a partir de esponjas del Caribe. Tesis en opción al título de Doctor en Ciencias Químicas. Universidad de La Habana, La Habana, Cuba.
Regalado, E. L.; Laguna, A.; Mendiola, J.; Nogueiras, C.; Thomas, O. P. 2010b. Bromopyrrole alkaloids from the Caribbean sponge Agelas cerebrum. Quimica Nova (in press).
Regalado, E. L.; Mendiola, J.; Laguna, A.; Nogueiras, C.; Thomas, O. P. 2010c. Polar alkaloids from the marine sponge Niphates digitalis. Natural Product Communications 5 (8): 1187-1190.
Regalado, E. L.; Tasdemir, D.; Kaiser, A.; Cachet, N.; Amade, P.; Thomas, O. P. 2010d. Antiprotozoal steroidal saponins from the marine sponge Pandaros acanthifolium. Journal of Natural Products 73: 1404–1410.
Regalado, E. L.; Jiménez, C. M.; Genta-Jouve, G.; Kaiser, M.; Tasdemir, D.; Amade, A.; Nogueiras, C.; Thomas, O. P. 2010e. Acanthifoliosides, minor steroidal saponins from the Caribbean sponge Pandaros acanthifolium. Tetrahedron (in press).
Rudi, A.; Kashman, Y.; Benayahu, Y.; Schleyer, M. 1994. Amino acid derivatives from the marine sponge Jaspis digonoxea. Journal of Natural Products 57: 829-832.
Rützler, K.; Feller, C. 1987. Mangrove swamp communities. Oceanus 30 (4): 16-24.
Sakai, R.; Higa, T.; Jefford, C. W.; Bernardinelli, G. 1986. Manzamine A; an antitumor alkaloid from a sponge. Journal of the American Chemical Society 108: 6404-6405.
Scheuer, P. J., Marine metabolites as drug leads-retrospect and prospect. In Biochemical Aspects of Marine Pharmacology [Online] Lazarovici, P.; Spira, M. E.; Zlotkin, E., Eds. Alaken, Inc: Fort Collins, Colorado, 1996; pp. 1-12.
Shen, Y.; Burgoyne, D. L. 2002. Efficient synthesis of IPL576,092: a novel anti-asthma agent. Journal of Organic Chemistry 67: 3908-3910.
Simmons, T. L.; Andrianasolo, E.; McPhail, K.; Flatt, P.; Gerwick, W. H. 2005. Marine natural products as anticancer drugs. Molecular Cancer Therapeutics 4: 333-342.
Simmons, T. L.; Coates, R. C.; Clark, B. R.; Engene, N.; Gonzalez, D.; Esquenazi, E.; Dorrestein, P. C.; Gerwick, W. H. 2008.
Biosynthetic origin of natural products isolated from marine microorganism–invertebrate assemblages. PNAS 105 (12): 4587–4594.
Simmons, T. L.; Gerwick, W. H., In Oceans and human health, Walsh, P.; Solo-Gabriele, H.; Fleming, L. E.; Smith, S. L.; Gerwick, W. H., Eds. Elsevier: New York, 2008.
Smith, A. B.; Freeze, B. S.; Xian, M.; Hirose, T. 2005. Total synthesis of (+)-discodermolide: a highly convergent fourth-generation approach. Organic Letters 7: 1825-1828.
Soriente, A.; De Rosa, M.; Scettri, A.; Sodano, G.; Terencio, M. C.; Paya, M.; Alcaraz, M. J. 1999. Manoalide. Current Medicinal Chemistry 6: 415-431.
Sweetman, S. C., The Complete Drug Reference. In Martindale ed.; Pharmaceutical Press: London, 2000; pp 484-487.
Talpir, R.; Benayahu, Y.; Kashman, Y.; Pannell, L.; Schleyer, M. 1994. Hemiasterlin and geodiamolide TA; two new cytotoxic peptides from the marine sponge Hemiasterella minor (Kirkpatrick). Tetrahedron Letters 35: 4453-4456.
Thakur, N. L.; Müller, W. E. G. 2004. Biotechnological potential of marine sponges. Current Science 86 (11): 1506-1512.
Towbin, H.; Bair, K. W.; DeCaprio, J. A.; Eck, M. J.; Kim, S.; Kinder, F. R.; Morollo, A.; Mueller, D. R.; Schindler, P.; Song, H. K.; van, O. J.; Versace, R. W.; Voshol, H.; Wood, J.; Zabludoff, S.; Phillips, P. E. 2003. Proteomics-based target identification: bengamides as a new class of methionine aminopeptidase inhibitors. Journal of Biological Chemistry 278: 52964-52971.
Uemura, D.; Takahashi, K.; Yamamoto, T.; Katayama, C.; Tanaka, J.; Okumura, Y.; Hirata, Y. 1985. Norhalichondrin A: an antitumor polyether macrolide from a marine sponge. Journal of the American Chemical Society 107: 4796-4798.
Wilkinson, C. R. 1983. Net primary productivity in coral reef sponges. Science 219: 410-412.
Yousaf, M.; Hammond, N. L.; Peng, J.; Wahyuono, S.; McIntosh, K. A.; Charman, W. N.; Mayer, A. M. S.; Hamman, M. T. 2004. New manzamine alkaloids from an Indo-Pacific sponge. Pharmacokinetic, oral avialability, and the significant activity of several manzamines against HIV-I, AIDS opportunistic infections, and inflammatory diseases. Journal of Medicinal Chemistry 47 (14): 3512-3517.
Aneiros, A.; Garateix, A.; García, T.; Palmero, A.; Valdés, A; Arteaga, F; Cuquerella, E. 2000. Informe Final del Proyecto No. 004-03-216 .Resultado 02 “ Evaluación de nuevas sustancias de origen marino con potencialidades como biofármacos”, Archivos del PNCT “Desarrollo de Productos Biotecnológicos, Farmacéuticos y de Medicina Verde”.
Aneiros, A.; Garateix, A.; García, T.; Palmero, A.; Valdés, A; Arteaga, F; Cuquerella, E. 2002. Informe Final del Proyecto “Obtención de nuevos compuestos de origen marino de aplicación en biomedicina“ No.067 Resultado 02 Archivos de la Agencia de Medio Ambiente, CITMA.
Bergmann, W.; Feeney, R. J. 1950. The isolation of a new thymine pentoside from sponges. Journal of the American Chemical Society 72: 2809-2810.
Bergmann, W.; Feeney, R. J. 1951. Constributions to the study of marine products. XXXII. The nucleosides of sponges. Journal of Organic Chemistry 16: 981-987.
Bergmann, W.; Burke, D. C. 1955. The nucleosides of sponges. 3. Spongothymidine and spongouridine (from Cryptotethia crypta). Journal of Organic Chemistry 20: 1501-1507.
Bergquist, P. R., Sponges. Hutchinson University library: Londres, 1978; 268 pages.
Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. 2005. Marine natural products. Natural Product Reports 20: 15-61.
Blunt, J. W.; Copp, B. R.; Hu, W.-P.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. 2007. Marine natural products. Natural Product Reports 24: 31-86.
Blunt, J. W.; Copp, B. R.; Hu, W.-P.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. 2008. Marine natural products (A review). Natural Product Reports 25 (1): 35-94.
Bramley, A. M.; Langlands, J. M.; Jones, A. K.; Burgoyne, D. L.; Li, Y.; Andersen, R. J.; Salari, H. 1995. Effects of IZP-94005 (contignasterol) on antigen-induced bronchial responsiveness in ovalbuminsensitized guinea-pigs. British Journal of Pharmacology 115: 1433-1438.
Bubb, M. R.; Senderowicz, A. M. J.; Sausville, E. A.; Duncan, K. L. K.; Korn, E. D. 1994. Jasplakinolide, a cytotoxic natural product, induces actin polymerization and competitively inhibits the binding of phalloidin to F-actin. Journal of Biological Chemistry 269: 14869-14871.
Burgoyne, D. L.; Andersen, R. J. 1992. Contignasterol, a highly oxygenated steroid with the “unnatural” 14 β configuration from the marine sponge Petrosia contignata Thiele, 1899. Journal of Organic Chemistry 57: 525-528.
Cachet, N.; Regalado, E. L.; Genta-Jouve, G.; Mehiri, M.; Amade, P.; Thomas, O. P. 2009. Steroidal glycosides from the marine sponge Pandaros acanthifolium. Steroids 74: 746-750.
Coleman, J. E.; de Silva, E. D.; Kong, F.; Andersen, R. J.; Allen, T. M. 1995. Cytotoxic peptides from the marine sponge Cymbastela sp. Tetrahedron 51: 10653-10662.
Corredor, J. E.; Wilkinson, C. R.; Vicente, V. P.; Morrel, J. M.; Otero, E. 1988. Nitrate release by Caribbeean reef sponges. Limnology and Oceanography 33 (1): 114-120.
El Sayed, K. A.; Kelly, M.; Kara, U. A. K.; Ang, K.; Katsuyama, I.; Dunbar, D. C.; Khan, A. A.; Hamman, M. T. 2001. New manzamines alkaloids with potent activity against infectious diseases. Journal of the American Chemical Society 123 (9): 1804-1808.
Gamble, W. R.; Durso, N. A.; Fuller, R. W.; Westergaard, C. K.; Johnson, T. R.; Sackett, D. L.; Hamel, E.; Cardellina, J. H.; Boyd, M. R. 1999. Cytotoxic and tubulin-interactive hemiasterlins from Auletta sp and Siphonochalina sp sponges. Bioorganic & Medicinal Chemistry 7: 1611-1615.
Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. 1990. Discodermolide: a new bioactive polyhydroxylated lactone from the marine sponge Discodermia dissoluta. Journal of Organic Chemistry 55: 4912-4915.
Hirata, Y.; Uemura, D. 1986. Halichondrins-antitumor polyether macrolides from a marine sponge. Pure and Applied Chemistry 58: 701-710.
Iijima, H.; Kimura, K.; Sakai, T.; Uchimura, A.; Shimizu, T.; Ueno, H.; Natori, T.; Koezuka, Y. 1998. Structure-activity relationship and conformational analysis of monoglycosylceramides on the syngeneic mixed leukocyte reaction. Bioorganic & Medicinal Chemistry 6: 1905-1910.
Jain, R.; Tiwari, A. 2007. Sponges: An invertebrate of bioactive potential. Current Science 93: 444-445.
Kobayashi, E.; Motoki, K.; Uchida, T.; Fukushima, H.; Koezuka, Y. 1995. KRN7000, a novel immunomodulator, and its antitumor activities. Oncology Research 7: 529-534.
Kuznetsov, G.; Towle, M. J.; Cheng, H.; Kawamura, T.; TenDyke, K.; Liu, D.; Kishi, Y.; Yu, M. J.; Littlefield, B. A. 2004. Induction of morphological and biochemical apoptosis following prolonged mitotic blockage by halichondrin B macrocyclic ketone analog E7389. Cancer Research 64: 5760-5766.
Loganzo, F.; Discafani, C. M.; Annable, T.; Beyer, C.; Musto, S.; Hari, M.; Tan, X.; Hardy, C.; Hernandez, R.; Baxter, M.; Singanallore, T.; Khafizova, G.; Poruchynsky, M. S.; Fojo, T.; Nieman, J. A.; Ayral-Kaloustian, S.; Zask, A.; Andersen, R. J.; Greenberger, L. M. 2003. HTI-286, a synthetic analogue of the tripeptide hemiasterlin, is a potent antimicrotubule agent that circumvents P-Glycoprotein-mediated resistance in vitro and in vivo. Cancer Research 63: 1838-1845.
Mayer, A. M.; Rodriguez, A. D.; Berlinck, R. G.; Hamann, M. T. 2007. Marine pharmacology in 2003–4: Marine compounds with anthelmintic, antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiplatelet, antiprotozoal, antituberculosis, and antiviral activities; affecting the cardiovascular, immune, and nervous systems and other miscellaneous mechanisms of action. Comparative Biochemistry and Physiology, C: Comparative Pharmacology and Toxicology 145: 553-581.
Mayer, A. M.; Rodriguez, A. D.; Berlinck, R. G.; Hamann, M. T. 2009. Marine pharmacology in 2005–6: Marine compounds with anthelmintic, antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiprotozoal, antituberculosis, and antiviral activities; affecting the cardiovascular, immune, and nervous systems and other miscellaneous mechanisms of action. Biochimica et Biophysica Acta 1790: 283-308.
Mayer, A. M. S.; Hamann, M. T. 2002. Marine compounds with anthelmintic, antibacterial, anticoagulant, antidiabetic, antifungal, anti-inflammatory, antimalarial, antiplatelet, antiprotozoal, and antiviral activities; affecting the cardiovascular, immune, and nervous systems and other miscellaneous mechanisms of action. Comparative Biochemistry and Physiology, C: Comparative Pharmacology and Toxicology 140: 265-286.
Munro, M. H. G.; Blunt, J. W., Marine Literatura DataBase (MarinLit), University de Canterbury, New Zealand, 2009.
Natori, T.; Y., K.; Higa, T. 1993. Agelasphins, novel alpha-galactosylceramides from the marine sponge Agelas mauritianus. Tetrahedron Letters 34: 5591-5592.
Natori, T.; Morita, M.; K., A.; Koezuka, Y. 1994. Agelasphins, novel antitumor and immunostimulatory cerebrosides from the marine sponge Agelas mauritianus. Tetrahedron 50: 2771-2784.
Orhan, I.; Şener, B.; Kaiser, M.; Brun, R.; Tasdemir, D. 2010. Inhibitory activity of marine sponge-derived natural products against parasitic Protozoa. Marine Drugs 5: 47-58.
Paterson, I.; Lyothier, I. 2004. Total synthesis of (+)-discodermolide: an improved endgame exploiting a Still-Gennari-type olefination with a C1-C8 b-ketophosphonate Fragment. Organic Letters 6: 4933-4936.
Rao, K. V.; Santarsiero, B. D.; Mesecar, A. D.; Schinazi, R. F.; Tezwani, B. L.; Hamman, M. T. 2003. New manzamine alkaloids with activity agains infectious and tropical parasitic diseases from an Indonesian sponge. Journal of Natural Products 66 (6): 823-828.
Rao, K. V.; Kasanah, N.; Wahyuono, S.; Tekwani, B. L.; Schinazi, R. F.; Hamman, M. T. 2004. Three new manzamine alkaloids from a common Indonesian sponge and their activity against infectious and tropical parasitic diseases. Journal of Natural Products 67 (8): 1314-1318.
Rao, K. V.; Donia, M. S.; Peng, J. N.; García-Palomero, E.; Alonso, D.; Martínez, A.; Medina, M.; Franzblau, S. G.; Tekwani, B. L.; Khan, S. I.; Wahyuono, S.; Willett, K. L.; Hamann, M. T. 2006. Manzamine B and E and ircinal A related alkaloids from an Indonesian Achanthostrongylophora sponge and their activity against infectious, tropical parasitic, and Alzheimer´s diseases. Journal of Natural Products 69 (7): 1034-1040.
Rayl, A. J. S. 1999. Oceans: medicine chests of the future? The Scientist 13: 1.
Regalado, E. L. 2010a. Aislamiento e identificación de metabolitos bioactivos a partir de esponjas del Caribe. Tesis en opción al título de Doctor en Ciencias Químicas. Universidad de La Habana, La Habana, Cuba.
Regalado, E. L.; Laguna, A.; Mendiola, J.; Nogueiras, C.; Thomas, O. P. 2010b. Bromopyrrole alkaloids from the Caribbean sponge Agelas cerebrum. Quimica Nova (in press).
Regalado, E. L.; Mendiola, J.; Laguna, A.; Nogueiras, C.; Thomas, O. P. 2010c. Polar alkaloids from the marine sponge Niphates digitalis. Natural Product Communications 5 (8): 1187-1190.
Regalado, E. L.; Tasdemir, D.; Kaiser, A.; Cachet, N.; Amade, P.; Thomas, O. P. 2010d. Antiprotozoal steroidal saponins from the marine sponge Pandaros acanthifolium. Journal of Natural Products 73: 1404–1410.
Regalado, E. L.; Jiménez, C. M.; Genta-Jouve, G.; Kaiser, M.; Tasdemir, D.; Amade, A.; Nogueiras, C.; Thomas, O. P. 2010e. Acanthifoliosides, minor steroidal saponins from the Caribbean sponge Pandaros acanthifolium. Tetrahedron (in press).
Rudi, A.; Kashman, Y.; Benayahu, Y.; Schleyer, M. 1994. Amino acid derivatives from the marine sponge Jaspis digonoxea. Journal of Natural Products 57: 829-832.
Rützler, K.; Feller, C. 1987. Mangrove swamp communities. Oceanus 30 (4): 16-24.
Sakai, R.; Higa, T.; Jefford, C. W.; Bernardinelli, G. 1986. Manzamine A; an antitumor alkaloid from a sponge. Journal of the American Chemical Society 108: 6404-6405.
Scheuer, P. J., Marine metabolites as drug leads-retrospect and prospect. In Biochemical Aspects of Marine Pharmacology [Online] Lazarovici, P.; Spira, M. E.; Zlotkin, E., Eds. Alaken, Inc: Fort Collins, Colorado, 1996; pp. 1-12.
Shen, Y.; Burgoyne, D. L. 2002. Efficient synthesis of IPL576,092: a novel anti-asthma agent. Journal of Organic Chemistry 67: 3908-3910.
Simmons, T. L.; Andrianasolo, E.; McPhail, K.; Flatt, P.; Gerwick, W. H. 2005. Marine natural products as anticancer drugs. Molecular Cancer Therapeutics 4: 333-342.
Simmons, T. L.; Coates, R. C.; Clark, B. R.; Engene, N.; Gonzalez, D.; Esquenazi, E.; Dorrestein, P. C.; Gerwick, W. H. 2008.
Biosynthetic origin of natural products isolated from marine microorganism–invertebrate assemblages. PNAS 105 (12): 4587–4594.
Simmons, T. L.; Gerwick, W. H., In Oceans and human health, Walsh, P.; Solo-Gabriele, H.; Fleming, L. E.; Smith, S. L.; Gerwick, W. H., Eds. Elsevier: New York, 2008.
Smith, A. B.; Freeze, B. S.; Xian, M.; Hirose, T. 2005. Total synthesis of (+)-discodermolide: a highly convergent fourth-generation approach. Organic Letters 7: 1825-1828.
Soriente, A.; De Rosa, M.; Scettri, A.; Sodano, G.; Terencio, M. C.; Paya, M.; Alcaraz, M. J. 1999. Manoalide. Current Medicinal Chemistry 6: 415-431.
Sweetman, S. C., The Complete Drug Reference. In Martindale ed.; Pharmaceutical Press: London, 2000; pp 484-487.
Talpir, R.; Benayahu, Y.; Kashman, Y.; Pannell, L.; Schleyer, M. 1994. Hemiasterlin and geodiamolide TA; two new cytotoxic peptides from the marine sponge Hemiasterella minor (Kirkpatrick). Tetrahedron Letters 35: 4453-4456.
Thakur, N. L.; Müller, W. E. G. 2004. Biotechnological potential of marine sponges. Current Science 86 (11): 1506-1512.
Towbin, H.; Bair, K. W.; DeCaprio, J. A.; Eck, M. J.; Kim, S.; Kinder, F. R.; Morollo, A.; Mueller, D. R.; Schindler, P.; Song, H. K.; van, O. J.; Versace, R. W.; Voshol, H.; Wood, J.; Zabludoff, S.; Phillips, P. E. 2003. Proteomics-based target identification: bengamides as a new class of methionine aminopeptidase inhibitors. Journal of Biological Chemistry 278: 52964-52971.
Uemura, D.; Takahashi, K.; Yamamoto, T.; Katayama, C.; Tanaka, J.; Okumura, Y.; Hirata, Y. 1985. Norhalichondrin A: an antitumor polyether macrolide from a marine sponge. Journal of the American Chemical Society 107: 4796-4798.
Wilkinson, C. R. 1983. Net primary productivity in coral reef sponges. Science 219: 410-412.
Yousaf, M.; Hammond, N. L.; Peng, J.; Wahyuono, S.; McIntosh, K. A.; Charman, W. N.; Mayer, A. M. S.; Hamman, M. T. 2004. New manzamine alkaloids from an Indo-Pacific sponge. Pharmacokinetic, oral avialability, and the significant activity of several manzamines against HIV-I, AIDS opportunistic infections, and inflammatory diseases. Journal of Medicinal Chemistry 47 (14): 3512-3517.