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http://dx.doi.org/10.4062/biomolther.2016.067

Marine Sponges as a Drug Treasure  

Anjum, Komal (Ocean College, Zhejiang University)
Abbas, Syed Qamar (Faculty of Pharmacy, Gomal University D.I.Khan)
Shah, Sayed Asmat Ali (Ocean College, Zhejiang University)
Akhter, Najeeb (Ocean College, Zhejiang University)
Batool, Sundas (Department of Molecular Biology, University of Heidelberg)
Hassan, Syed Shams ul (Ocean College, Zhejiang University)
Publication Information
Biomolecules & Therapeutics / v.24, no.4, 2016 , pp. 347-362 More about this Journal
Abstract
Marine sponges have been considered as a drug treasure house with respect to great potential regarding their secondary metabolites. Most of the studies have been conducted on sponge's derived compounds to examine its pharmacological properties. Such compounds proved to have antibacterial, antiviral, antifungal, antimalarial, antitumor, immunosuppressive, and cardiovascular activity. Although, the mode of action of many compounds by which they interfere with human pathogenesis have not been clear till now, in this review not only the capability of the medicinal substances have been examined in vitro and in vivo against serious pathogenic microbes but, the mode of actions of medicinal compounds were explained with diagrammatic illustrations. This knowledge is one of the basic components to be known especially for transforming medicinal molecules to medicines. Sponges produce a different kind of chemical substances with numerous carbon skeletons, which have been found to be the main component interfering with human pathogenesis at different sites. The fact that different diseases have the capability to fight at different sites inside the body can increase the chances to produce targeted medicines.
Keywords
Sponges; Pharmacokinetics; Antitumor; Antiviral; Pathogenesis; Microbes;
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1 Hill, R. T., Hamann, M., Peraud, O. and Kasanah, N., inventors; University of Maryland Biotechnology Institute, assignee. Manzamineproducing actinomycetes. United States patent US 20050244938 A1. 2005 Nov 3.
2 Hood, K. A., West, L. M., Rouwe, B., Northocote, P. T., Berridge, M. V., Wakefield, S. J. and Miller, J. H. (2002) Peloruside A, a novel antimitotic agent with paclitaxel-like microtubule-stabilizing activity. Cancer Res. 62, 3356-3360.
3 Hooper, J. N. A. and van Soest, R. W. M. (2002) Systema porifera: a guide to the classification of sponges. Kluwer Academic/Plenum Publishers, New York.
4 Hu, G. P., Yuan, J., Sun, L., She, Z. G., Wu, J. H., Lan, X. J., Zhu, X., Lin, Y. C. and Chen, S. P. (2011) Statistical research on marine natural products based on data obtained between 1985 and 2008. Mar. Drugs 9, 514-525.   DOI
5 Hua, H. M., Peng, J., Fronczek, F. R., Kelly, M. and Hamann, M. T. (2004) Crystallographic and NMR studies of antiinfective tricyclic guanidine alkaloids from the sponge Monanchora unguifera. Bioorg. Med. Chem. 12, 6461-6464.   DOI
6 Hultgren, K. M. and Duffy, J. E. (2010) Sponge host characteristics shape the community structure of their shrimp associates. Mar. Ecol. Prog. Ser. 407, 1-12.   DOI
7 Ikenaga, M., Higaki, Y., Saku, K. and Uehara, Y. (2016) High-Density Lipoprotein Mimetics: a Therapeutic Tool for Atherosclerotic Diseases. J. Atheroscler. Thromb. 23, 385-394.   DOI
8 Jang, K. H., Chung, S. C., Shin, J., Lee, S. H., Kim, T. I., Lee, H. S. and Oh, K. B. (2007). Aaptamines as sortase A inhibitors from the tropical sponge Aaptos aaptos. Bioorg. Med. Chem. Lett. 17, 5366-5369.   DOI
9 Jares-Erijman, E. A., Sakai, R. and Rinehart, K. L. (1991) Crambescidins: new antiviral and cytotoxic compounds from the sponge Crambe crambe. J. Org. Chem. 56, 5712-5715.   DOI
10 Juagdan, E. G., Kalindindi, R. S., Scheuer, P. J. and Kelly-Borges, M. (1995) Elenic acid, an inhibitor of topoisomerase II, from a sponge, Plakinastrella sp. Tetrahedron Lett. 36, 2905-2908.   DOI
11 Kalinin, V. I., Ivanchina, N. V., Krasokhin, V. B., Makarieva, T. N. and Stonik, V. A. (2012). Glycosides from marine sponges (Porifera, Demospongiae): structures, taxonomical distribution, biological activities and biological roles. Mar. Drugs 10, 1671-1710.   DOI
12 Kang, J.-H. (2014) Protein kinase C (PKC) isozymes and cancer. New J. Sci. 2014, 231418.
13 Kitagawa, I., Kobayashi, M., Kitanaka, K., Kido, M. and Kyogoku, Y. (1983) Marine natural products, XII: on the chemical constituents of the Okinawan marine sponge Hymeniacidon aldis. Chem. Pharm. Bull. 31, 2321-2328.   DOI
14 Kobayashi, J. and Ishibashi, M. (1993) Bioactive metabolites of symbiotic marine microorganisms. Chem. Rev. 93, 1753-1769.   DOI
15 Konig, G. M., Wright, A. D. and Angerhofer, C. K. (1996) Novel potent antimalarial diterpene isocyanates, isothiocyanates, and isonitriles from the tropical marine sponge Cymbastela hooperi. J. Org. Chem. 61, 3259-3267.   DOI
16 Kossuga, M. H., Nascimento, A. M., Reimao, J. Q., Tempone, A. G., Taniwaki, N. N., Veloso, K., Ferreira, A. G., Cavalcanti, B. C., Pessoa, C., Moraes, M. O., Mayer, A. M., Hajdu, E. and Berlinck, R. G. (2008) Antiparasitic, antineuroinflammatory, and cytotoxic polyketides from the marine sponge Plakortis angulospiculatus collected in Brazil. J. Nat.Prod. 71, 334-339.   DOI
17 Linington, R. G., Robertson, M., Gauthier, A., Finlay, B. B., MacMillan, J. B., Molinski, T. F., van Soest, R. and Andersen, R. J. (2006) Caminosides BD, Antimicrobial Glycolipids Isolated from the Marine Sponge Caminus s phaeroconia. J. Nat. Prod. 69, 173-177.   DOI
18 Kolodziejczyk, J. and Ponczek, M. B. (2013) The role of fibrinogen, fibrin and fibrin (ogen) degradation products (FDPs) in tumor progression. Contemp. Oncol. (Pozn.) 17, 113-119.
19 Laport, M. S., Santos, O. C. and Muricy, G. (2009) Marine sponges:potential sources of new antimicrobial drugs. Curr. Pharm. Biotechnol. 10, 86-105.   DOI
20 Leal, M. C., Puga, J., Serodio, J., Gomes, N. C. M. and Calado, R. (2012) Trends in the discovery of new marine natural products from invertebrates over the last two decades - where and what are we bioprospecting? PLoS ONE 7, e30580.   DOI
21 Liu, B., Timar, J., Howlett, J., Diglio, C. A. and Honn, K. V. (1991) Lipoxygenase metabolites of arachidonic and linoleic acids modulate the adhesion of tumor cells to endothelium via regulation of protein kinase C. Cell Regul. 2, 1045-1055.   DOI
22 Loya, S. and Hizi, A. (1990) The inhibition of human immunodeficiency virus type 1 reverse transcriptase by avarol and avarone derivatives. FEBS Lett. 269, 131-134.   DOI
23 Lundberg, U. (1995) Methods and applications of stress research. Technol. Health Care 3, 3-9.
24 Maldonado, M., Carmona, C., Velasquez, Z., Puig, A., Cruzado, A., Lopez, A. and Young, C. M. (2005) Siliceous sponges as a silicon sink: An overlooked aspect of the benthopelagic coupling in the marine silicon cycle. Limnol. Oceanogr. 50, 799-809.   DOI
25 Maria, M., Lone, G. and Thomas, O. L. (2011) Production of bioactive secondary metabolites by marine vibrionaceae. Mar. Drugs 9, 1440-1468.   DOI
26 Mayer, A. M., Rodriguez, A. D., Berlinck, R. G. and Fusetani, N. (2011) Marine pharmacology in 2007-8: Marine compounds with antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiprotozoal, antituberculosis, and antiviral activities; affecting the immune and nervous system, and other miscellaneous mechanisms of action. Comp. Biochem. Physiol. C Toxicol. Pharmacol. 153, 191-222.   DOI
27 Martins, A., Vieira, H., Gaspar, H. and Santos, S. (2014) Marketed marine natural products in the pharmaceutical and cosmoceutical industries: tips for success. Mar. Drugs 12, 1066-1101.   DOI
28 Maryanoff, B. E., Qiu, X., Padmanabhan, K. P., Tulinsky, A., Almond, H. R., Andrade-Gordon, P., Greco, M. N., Kauffman, J. A., Nicolaou, K. C., Liu, A., Brungs, P. H. and Fusetani, N. (1993) Molecular basis for the inhibition of human alpha-thrombin by the macrocyclic peptide cyclotheonamide A. Proc. Natl. Acad. Sci. U.S.A. 90, 8048-8052.   DOI
29 Matsunaga, S., Fusetani, N. and Konosu, S. (1985) Bioactive marine metabolites, VII: structures of discodermins B, C, and D, antimicrobial peptides from the marine sponge Discodermia kiiensis. Tetrahedron Lett. 26, 855-856.   DOI
30 Mayer, A. M. and Hamann, M. T. (2004) Marine pharmacology in 2000:marine compounds with antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiplatelet, antituberculosis, and antiviral activities; affecting the cardiovascular, immune, and nervous systems and other miscellaneous mechanisms of action. Mar. Biotechnol. 6, 37-52.   DOI
31 Mayer, A. M. S. and Jacobs, R. S. (1988) Manoalide: an anti-inflammatory and analgesic marine natural product. Mem. Calif. Acad. Sci. 13, 133.
32 Miyamoto, S., Izumi, M., Hori, M., Kobayashi, M., Ozaki, H. and Karaki, H. (2000) Xestospongin C, a selective and membrane-permeable inhibitor of $IP_3$ receptor, attenuates the positive inotropic effect of ${\alpha}$-adrenergic stimulation in guinea-pig papillary muscle. Br. J. Pharmacol. 130, 650-654.   DOI
33 Mayer, A. M. S. and Lehmann, V. K. B. (2000) Marine pharmacology in 1998: marine compounds with antibacterial, anticoagulant, antifungal, anti-inflammatory, anthelmintic, antiplatelet, antiprotozoal, and antiviral activities; with actions on the cardiovascular, endocrine, immune, and nervous systems; and other miscellaneous mechanisms of action. Pharmacologist 42, 62-69.
34 McCaffrey, E. J. and Endeau, R. (1985) Antimicrobial activity of tropical and subtropical sponges. Mar. Biol. 89, 1-8.   DOI
35 Mishra, S. K., Satpathy, S. K. and Mohanty, S. (1999) Survey of malaria treatment and deaths. Bull. World Health Organ. 77, 1020.
36 Miyaoka, H., Shimomura, M., Kimura, H., Yamada, Y., Kim, H. S. and Wataya, Y. (1998) Antimalarial activity of kalahinol A and new relative diterpenoids from the Okinawan sponge, Acanthella sp. Tetrahedron 54, 13467-13474.   DOI
37 Mol, V. P. L., Raveendran, T. V. and Parameswaran, P. S. (2009) Antifouling activity exhibited by secondary metabolites of the marine sponge, Haliclona exigua (Kirkpatrick). Int. Biodeterior. Biodegrad. 63, 67-72.   DOI
38 Momparler, R. L. (2013) Optimization of cytarabine (ARA-C) therapy for acute myeloid leukemia. Exp. Hematol. Oncol. 2, 20.   DOI
39 Morton, S. L., Moeller, P. D., Young, K. A. and Lanoue, B. (1998) Okadaic acid production from the marine dinoflagellate Prorocentrum belizeanum Faust isolated from the Belizean coral reef ecosystem. Toxicon. 36, 201-206.   DOI
40 Moura, R. M., Queiroz, A. F., Fook, J. M., Dias, A. S., Monteiro, N. K., Ribeiro, J. K., Moura, G. E., Macedo, L. L., Santos, E. A. and Sales, M. P. (2006) CvL, a lectin from the marine sponge Cliona varians: Isolation, characterization and its effects on pathogenic bacteria and Leishmania promastigotes. Comp. Biochem. Physiol., Part A Mol. Integr. Physiol. 145, 517-523.   DOI
41 Muller, W. G., Sobel, C., Diehl-Seifert, B., Maidhof, A. and Schroder, H. C. (1987) Influence of the antileukemic and anti-human immunodeficiency virus agent avarol on selected immune responses in vitro and in vivo. Biochem. Pharmacol. 36, 1489-1494.   DOI
42 Muller, W. E., Schröder, H. C., Wiens, M., Perovic-Ottstadt, S., Batel, R. and Muller, I. M. (2004) Traditional and modern biomedical prospecting: Part II-the benefits. Evid. Based Complement. Alternat. Med. 1, 133-144.   DOI
43 Nausch, B., Heppner, T. J. and Nelson, M. T. (2010) Nerve-released acetylcholine contracts urinary bladder smooth muscle by inducing action potentials independently of $IP_3$-mediated calcium release. Am. J. Physiol. Regul. Integr. Comp. Physiol. 299, R878-R888.   DOI
44 Northcote, P. T., Blunt, J. W. and Munro, M. H. G. (1991) Pateamine: a potent cytotoxin from the New Zealand marine sponge, mycale sp. Tetrahedron Lett. 32, 6411-6414.   DOI
45 Oclarit, J. M., Okada, H., Ohta, S., Kaminura, K., Yamaoka, Y., Iizuka, T., Miyashiro, S. and Ikegami, S. (1994) Anti-bacillus substance in the marine sponge, Hyatella species, produced by an associated Vibrio species bacterium. Microbios 78, 7-16.
46 Oh, K. B., Mar, W., Kim, S., Kim, J. Y., Lee, T. H., Kim, J. G., Shin, D., Sim, C. J. and Shin, J. (2006) Antimicrobial activity and cytotoxicity of bis (indole) alkaloids from the sponge Spongosorites sp. Biol. Pharm. Bull. 29, 570-573.   DOI
47 Petit, G. R. and Knight, J. C., inventors; Arizona Board of Regents, assignee. Cribrostatins 3-5. United States patent US 6437128 B1. 2002 Aug 20.
48 O'Rourke, A., Kremb, S., Bader, T. M., Helfer, M., Schmitt-Kopplin, P., Gerwick, W. H., Brack-Werner, R. and Voolstra, C. R. (2016) Alkaloids from the sponge Stylissa carteri present prospective scaffolds for the inhibition of human immunodeficiency Virus 1 (HIV-1). Mar. Drugs 14, 28.   DOI
49 Pattenden, G., Critcher, D. J. and Remuinan, M. (2004) Total synthesis of ()-pateamine A, a novel immunosuppressive agent from Mycale sp. Can. J. Chem. 82, 353-365.   DOI
50 Perry, N. B., Blunt, J. W., Munro, M. H. G. and Thompson, A. M. (1990) Antiviral and antitumor agents from a New Zealand sponge, Mycale sp. 2. Structures and solution conformations of mycalamides A and B. J. Org. Chem. 55, 223-227.   DOI
51 Pettit, R. K., Fakoury, B. R., Knight, J. C., Weber, C. A., Pettit, G. R., Cage, G. D. and Pon, S. (2004) Antibacterial activity of the marine sponge constituent cribrostatin 6. J. Med. Microbiol. 53, 61-65.   DOI
52 Piel, J. (2004) Metabolites from symbiotic bacteria. Nat Prod Rep. 21, 519-538.   DOI
53 Piel, J. (2006) Bacterial symbionts: prospects for the sustainable production of invertebrate-derived pharmaceuticals. Curr. Med. Chem. 13, 39-50.   DOI
54 Pika, J., Tischler, M. and Andersen, R. J. (1992) Glaciasterols A and B, 9,11-secosteroids from the marine sponge Aplysilla glacialis. Can. J. Chem. 70, 1506-1510.   DOI
55 Plaza, A., Gustchina, E., Baker, H. L., Kelly, M. and Bewley, C. A. (2007) Mirabamides A-D, depsipeptides from the sponge Siliquariaspongia mirabilis that inhibit HIV-1 fusion. J. Nat. Prod. 70, 1753-1760.   DOI
56 Quinn, R. J., Gregson, R. P., Cook, A. F. and Bartlett, A. F. (1980) Isolation and synthesis of 1-methylisoguanisine, a potent pharmacologically active constituent from the marine sponge Tedania digitata. Tetrahedron Lett. 21, 567-568.   DOI
57 Ponton, J., Ruchel, R., Clemonds, K. V., Coleman, D. C., Grillot, R., Guarro, J., Aldebert, D., Ambroise-Thomas, P., Cano, J., Carrillo-Munoz, A. J., Gene, J., Pinel, C., Stevens, D. A. and Sullivan, D. (2000) Emerging pathogens. Med. Mycol. 38, 225-236.   DOI
58 Proksch, P., Edrada, R. A. and Ebel, R. (2002) Drugs from the seascurrent status and microbiological implications. Appl. Microbiol. Biotechnol. 59, 125-134.   DOI
59 Proksch, P., Putz, A., Ortlepp, S., Kjer, J. and Bayer, M. (2010) Bioactive natural products from marine sponges and fungal endophytes. Phytochem. Rev. 9, 475-489.   DOI
60 Qureshi, A. and Faulkner, D. J. (1999) Haplosamates A and B: new steroidal sulfamate esters from two haplosclerid sponges. Tetrahedron 55, 8323-8330.   DOI
61 Rahden-Staron, I. (2002) The inhibitory effect of the fungicides captan and captafol on eukaryotic topoisomerases in vitro and lack of recombinagenic activity in the wing spot test of Drosophila melanogaster. Mutat. Res. 518, 205-213.   DOI
62 Ramel, G. (2010) Phylum Porifera [cited 2013 Jan]. Available from:http://www.earthlife.net/inverts/porifera.html/.
63 Rao, V. K., Kasanah, N., Wahyuono, S., Tekwani, B. L., Schinazi, R. F. and Hamann, M. T. (2004) Three new manzamine alkaloids from a common indonesian sponge and their activity against infectious and tropical parasitic diseases. J. Nat. Prod. 67, 1314-1318.   DOI
64 Rice, L. B. (2006) Antimicrobial resistance in gram-positive bacteria. Am. J. Infect. Control 34, S11-S19.   DOI
65 Sakai, R., Higa, T., Jefford, C. W. and Bernardinelli, G. (1986) Manzamin, A., a novel antitumor alkaloid from a sponge. J. Am. Chem. Soc. 108, 6404-6405.   DOI
66 Romo, D., Rzasa, R. M., Shea, H. A., Park, K., Langenhan, J. M., Sun, L., Akhiezer, A. and Liu, J. O. (1998) Total synthesis and immunosuppressive activity of (-)-pateamine A and related compounds: implementation of a b-lactambased macrocyclization. J. Am. Chem. Soc. 120, 12237-12254.   DOI
67 Rubio, B. K., van Soest, R. W. and Crews, P. (2007) Extending the record of meroditerpenes from Cacospongia marine sponges. J. Nat. Prod. 70, 628-631.   DOI
68 Sagar, S., Kaur, M., Minneman, K. P. (2010) Antiviral lead compounds from marine sponges. Mar. Drugs 8, 2619-2638.   DOI
69 Sandven, P. (2000) Epidemiology of candidemia. Rev. Iberoam. Micol. 17, 73-81.
70 Schaschke, N. and Sommerhoff, P. C. (2010) Upgrading a natural product: inhibition of human ${\beta}$-tryptase by cyclotheonamide analogues. Chem. Med. Chem. 5, 367-370.   DOI
71 Schwartsmann, G. (2000) Marine organisms and other novel natural sources of new cancer drugs. Ann. Oncol. 11, 235-243.
72 Shimosaka, A. (2002) Role of NKT cells and a-galactosyl ceramide. Int. J. Hematol. 76, 277-279.   DOI
73 Shuman, R.T., Rothenberger, R. B., Campell, C. S., Smith, G. F., Gifford-Moore, D. S. and Gesellchen, P. D. (1993) Highly selective tripeptide thrombm inhibitors. J. Med. Chem. 36, 314-319.   DOI
74 Sipkema, D., Osinga, R., Schatton, W., Mendola, D., Tramper, J. and Wijffels, R. H. (2005) Large scale production of pharmaceuticals by marine sponges: Sea, cell, or biosynthesis. Biotechnol. Bioeng. 90, 201-222.   DOI
75 Ang, K. K., Holmes, M. J. and Kara, U. A. (2001) Immunemediated parasite clearance in mice infected with Plasmodium berghei following treatment with manzamine A. Parasitol. Res. 87, 715-721.   DOI
76 Amade, P., Charroin, G., Baby, C. and Vacelet, J. (1987) Antimicrobial activity of marine sponges of Mediterranean. Sea. Mar. Biol. 94, 271-275.   DOI
77 Amade, P. H., Pesando, D. and Chevolot, L. (1982) Antimicrobial activities of marine from French Polynesia and Brittany. Mar. Biol. 70, 223-228.   DOI
78 Amigo, M., Terencio, M. C., Paya, M., Iodice, C. and De Rosa, S. (2007) Synthesis and evaluation of diverse thio avarol derivatives as potential UVB photoprotective candidates. Bioorg. Med. Chem. Lett. 17, 2561-2565.   DOI
79 Arimoto, H., Hayakawa, I., Kuramoto, M. and Uemura, D. (1998) Absolute stereochemistry of halichlorine; a potent inhibitor of VCAM-1 induction. Tetrahedron Lett. 39, 861-862.   DOI
80 Souza, T. M., Abrantes, J. L., de A Epifanio, R., Leite Fontes, C. F. and Frugulhetti, I. C. (2007) The alkaloid 4-methylaaptamine isolated from the sponge Aaptos aaptos impairs Herpes simplex virus Type 1 penetration and immediate early protein synthesis. Planta Med. 73, 200-205.   DOI
81 Stead, P., Hiscox, S., Robinson, P, S., Pike, N. B., Sidebottom, P. J., Roberts, A. D., Taylor, N. L., Wright, A. E., Pomponi, S. A. and Langley, D. (2000) Eryloside F, a novel penasterol disaccharide possessing potent thrombin receptor antagonist activity. Bioorg. Med. Chem. Lett. 10, 661-664.   DOI
82 Suzuki, H., Shindo, K., Ueno, A., Miura, T., Takei, M., Sakakibara, M., Fukamachi, H., Tanaka, J. and Higa, T. (1999) S1319: A novel ${\beta}2$-adrenoceptor agonist from a marine sponge Dysidea sp. Bioorg. Med. Chem. Lett. 9, 1361-1364.   DOI
83 Takei, M., Burgoyne, D. L. and Andersen, R. J. (1994) Effect of contignasterol on histamine release induced by anti-immunoglobulin E from rat peritoneal mast cells. J. Pharm. Sci. 83, 1234-1235.   DOI
84 Tan, P., Luscinskas, F. W. and Homer-Vanniasinkam, S. (1997) Cellular and molecular mechanisms of inflammation and thrombosis. Eur. J. Vasc. Endovasc. Surg. 17, 373-389.
85 Tasdemir, D., Topaloglu, B., Perozzo, R., Brun, R., O'Neill, R., Carballeira, N. M., Zhang, X., Tonge, P. J., Linden, A. and Ruedi, P. (2007) Marine natural products from the Turkish sponge Agelas oroides that inhibit the enoyl reductases from Plasmodium falciparum, Mycobacterium tuberculosis and Escherichia coli. Bioorg. Med. Chem. 15, 6834-6845.   DOI
86 Ter Haar, E., Kowalski, R. J., Hamel, E., Lin, C. M., Longley, R. E., Gunasekera, S. P., Rosenkranz, H. S. and Day, B. W. (1996) Discodermolide, a cytotoxic marine agent that stabilizes microtubules more potently than taxol. Biochemistry 35, 243-250.   DOI
87 Barrese, V. and Taglialatela, M. (2013) New advances in beta-blocker therapy in heart failure. Front. Physiol. 4, 323.
88 Ashok, P., Ganguly, S. and Murugesan S. (2014) Manzamine alkaloids:isolation, cytotoxicity, antimalarial activity and SAR studies. Drug Discovr. Today 19, 1781-1791.   DOI
89 Aviles, E. and Rodriguez, A. D. (2010) Monamphilectine A, a Potent Antimalarial ${\beta}$-Lactam from Marine Sponge Hymeniacidon sp:Isolation, Structure, Semisynthesis, and Bioactivity. Org. Lett. 12, 5290-5293.   DOI
90 Baird, J. K. (2013) Evidence and implications of mortality associated with acute Plasmodium vivax malaria. Clin. Microbiol. Rev. 26, 36-57.   DOI
91 Bergmann, W. and Feeney, R. J. (1950) The isolation of a new thymine pentoside from sponges. J. Am. Chem. Soc. 72, 2809-2810.
92 Bergmann, W. and Feeney, R. J. (1951) Contribution to the study of marine products. J. Org. Chem. 16, 981-987.   DOI
93 Bergmann, W. and Swift, A. N. (1951) Contributions to the study of marine products. XXX. Component acids of lipids sponges. I. J. Org. Chem. 16, 1206-1221.   DOI
94 Blackburn, C. L., Hopmann, C., Sakowicz, R., Berdelis, M, S., Goldstein, L. S. B. and Faulkner, D. J. (1999) Adociasulfates 1-6, inhibitors of kinesin motor proteins from the sponge Haliclona (aka Adocia) sp. J. Org. Chem. 64, 5565-5570.   DOI
95 Blunt, J. W., Copp, B. R., Keyzers, R. A., Munroa, M. H. and Prinsep, M. R. (2013) Marine natural products. Nat. Prod. Rep. 30, 237-323.   DOI
96 Blunt, J. W., Copp, B. R., Munro, M. H., Northcote, P. T. and Prinsep, M. R. (2005) Marine natural products. Nat. Prod. Rep. 22, 15-61.   DOI
97 Urban, S., De Almeida Leone, P., Carroll, A. R., Fechner, G. A., Smith, J., Hooper, J. N. and Quinn, R. J. (1999) Axinellamines A-D, novel imidazo-azolo-imidazole alkaloids from the australian marine sponge Axinella sp. J. Org. Chem. 64, 731-735.   DOI
98 Thomas, T. R., Kavlekar, D. P., and LokaBharathi, P. A. (2010) Marine drugs from sponge-microbe association-a review. Mar. Drugs 8, 1417-1468.   DOI
99 Torres, Y. R., Berlink, R. G., Nascimento, G. G., Fortier, S. C., Pessoa, C. and de Moraes, M. O. (2002) Antibacterial activity against resistant bacteria and cytotoxicity of four alkaloid toxins isolated from the marine sponge Arenosclera brasiliensis. Toxicon. 40, 885-891.   DOI
100 Turk, T., Ambrozic Avgustin, J., Batista, U., Strugar, G., Kosmina, R., Civovic, S., Janussen, D., Kauferstein, S., Mebs, D. and Sepcic, K. (2013) Biological activities of ethanolic extracts from deep-sea antarctic marine sponges. Mar. Drugs 11, 1126-1139.   DOI
101 Uriz, M. J., Martin, D. and Rosell, D. (1992) Relationships of biological and taxonomic characteristics to chemically mediated bioactivity in Mediterranean littoral sponges. Mar. Biol. 113, 287-297.
102 Vik, A., Hedner, E., Charnock, C., Tangen, L. W., Samuelsen, O., Larsson, R., Bohlin, L. and Gundersen, L. L. (2007) Antimicrobial and cytotoxic activity of agelasine and agelasimine analogs. Bioorg. Med. Chem. 15, 4016-4037.   DOI
103 Wakimoto, T., Maruyama, A., Matsunaga, S., Fusetani, N., Shinoda, K. and Murphy, P. T. (1999) Octa- and nonaprenylhydroquinone sulfates, inhibitors of a1,3-fucosyltransferase VII, from an Australian marine sponge Sarcotragus sp. Bioorg. Med. Chem. Lett. 9, 727-730.   DOI
104 Bradshaw, D., Hill, C. H., Nixon, J. S. and Wilkinson, S. E. (1993) Therapeutic potential of protein kinase C inhibitors. Agents Actions 38, 135-147.   DOI
105 Blunt, J. W., Copp, B. R., Munro, M. H., Northcote, P. T. and Prinsep, M. R. (2006) Marine natural products. Nat. Prod. Rep. 23, 26-78.   DOI
106 Boonlarppradab, C. and Faulkner, D. J. (2007) Eurysterols A and B, cytotoxic and antifungal steroidal sulfates from a marine sponge of the genus Euryspongia. J. Nat. Prod. 70, 846-848.   DOI
107 Borchard, U. (1998) Pharmacological properties of b-adrenoreceptor blocking drugs. J. Clin. Basic Cardiol. 1, 5-9.
108 Brazilian Health Ministry (2002) Epidemiological survey of malaria in Brazil, Funasa, Brasilia. Available from: http://www.funasa.gov.br/.
109 Burkholder, P. R. and Ruetzler, K. (1969) Antimicrobial activity of some marine sponges. Nature 222, 983-984.   DOI
110 Capon, R. J., Skene, C., Lacey, E., Gill, J. H., Wadsworth, D. and Friedel, T. (1999) Geodin A magnesium salt: a novel nematocide from a southern Australian marine sponge, Geodia. J. Nat. Prod. 62, 1256-1259.   DOI
111 Capon, R. J., Vuong, D., McNally, M., Peterle, T., Trotter, N., Lacey, E. and Gill, J. H. (2005) (+)-Echinobetaine B: isolation, structure elucidation, synthesis and preliminary SAR studies on a new nematocidal betaine from a southern Australian marine sponge, Echinodictyum sp. Org Biomol. Chem. 3, 118-122.   DOI
112 Caraballo, H. and King, K. (2014) Emergency department management of mosquito-borne illness: malaria, dengue, and west nile virus. Emerg. Med. Pract. 16, 1-23.
113 White, D. E. and Fenner, F. J. (1986) Medical Virology. Academic Press., San Diego.
114 Walsh, T. J., Groll, A., Hiemenz, J., Fleming, R., Roilides, E. and Anaissie, E. (2004) Infections due to emerging and uncommon medically important fungal pathogens. Clin. Microbiol. Infect. 10, 48-66.   DOI
115 Walter, S. (2005) Drug discovery: a history. p. 258. Wiley, New York.
116 Wellington, K. D., Cambie, R. C., Rutledge, P. S. and Bergquist, P. R. (2000) Chemistry of Sponges. 19. Novel Bioactive Metabolites from Hamigeratarangaensis. J. Nat. Prod. 63, 79-85.   DOI
117 WHO (2015) World Malaria report. World Health Organization, Geneva.
118 Wiedbrauk, D. L. and Johnston, S. L. G. (1992) Manual of Clinical Virology. Raven Press., New York.
119 Xue, S., Zhanga, H. T., Wua, P. C., Zhanga, W. and Yuana, Q. (2004) Study on bioactivity of extracts from marine sponges in Chinese Sea. J. Exp. Mar. Biol. Ecol. 298, 71-78.   DOI
120 Yasuhara-Bell, J. and Lu, Y. (2010) Marine compounds and their antiviral activities. Antiviral Res. 86, 231-240.   DOI
121 Yousaf, M., El Sayed, K. A., Rao, K. V., Lim, C. W., Hu, J. F., Kelly, M., Franzblau, S. G, Zhang, F., Peraud, O., Hill, R. T. and Hamann, M. T. (2002) 12,34-Oxamanzamines, novel biocatalytic and natural products from rnanzamine producing Indo-Pacific sponges. Tetrahedron 58, 7397-7402.   DOI
122 Zabriskie, T. M., Klocke, J. A., Ireland, C. M., Marcus, A. H., Molinski, T. F., Faulkner, D. J., Xu, C. and Clardy, J. C. (1986) Jaspamide, a modified peptide from a Jaspis sponge, with insecticidal and antifungal activity. J. Am. Chem. Soc. 108, 3123-3124.   DOI
123 Costantino, V., Fattorusso, E., Mangoni, A., Di Rosa, M. and Ianaro, A. (1999) Glycolipids from sponges, VII: simplexides, novel immunosuppressive glycolipids from the Caribbean sponge Plakortis simplex. Bioorg. Med. Chem. Lett. 9, 271-276.   DOI
124 Carroll, J., Johnsson, E. N., Ebel, R., Hartman, M. S., Holman, T. R. and Crews, P. (2001) Probing sponge-derived terpenoids for human 15-L-lipoxygenase inhibitors. J. Org. Chem. 66, 6847-6851.   DOI
125 Chackalamannil, S. and Xia, Y. (2006) Thrombin receptor (PAR-1) antagonists as novel antithrombotic agents. Expert Opin. Ther. Pat. 16, 493-505.   DOI
126 Cheng, S., Wen, Z., Chiou, S., Hsu, C., Wang, S., Dai, C., Chiang, M. Y. and Duh, C. (2008) Durumolides A-E, anti-inflammatory and antibacterial cembranolides from the soft coral Lobophytum durum. Tetrahedron 64, 9698-9704.   DOI
127 Cutignano, A., Bifulco, G., Bruno, I., Casapullo, A., Gomez-Paloma, L. and Riccio, R. (2000) Dragmacidin F: A New Antiviral Bromoindole Alkaloid from the Mediterranean Sponge Halicortex sp. Tetrahe-dron 56, 3743-3748.   DOI
128 D Ambrosio, M., Guerriero, A., Deharo, E., Debitus, C., Munoz, V. and Pietra, F. (1998) New types of potentially antimalarial agents: epidioxy-substituted norditerpene and norsesterpenes from the marine sponge Diacarnuslevii. Helv. Chim. Acta 81, 1285-1292.   DOI
129 de Almeida Leone, P., Redburn, J., Hooper, J. N. and Quinn, R. J. (2000) Polyoxygenated dysidea sterols that inhibit the binding of [I125] IL-8 to the human recombinant IL-8 receptor type A. J. Nat. Prod. 63, 694-697.   DOI
130 De Clercq, E. (2002) New anti-HIV agents and targets. Med. Res. Rev. 22, 531-565.   DOI
131 De Clercq, E. (2004) Antiviral drugs in current clinical use. J. Clin. Virol. 30, 115-133.   DOI
132 Ebada, S. S., Wray, V., de Voogd, N. J., Deng, Z., Lin, W. and Proksch, P. (2009) Two new jaspamide derivatives from the marine sponge Jaspis splendens. Mar. Drugs 7, 435-444.   DOI
133 Zapolska-Downar, D., Zapolska-Downar, A., Markiewski, M., Ciechanowicz, M., Kaczmarczyk, M. and Naruszewicz, M. (2001) Selective inhibition by procubol of vascular cell adhesion molecule 1(VCAM-1) expression in human vascular endothelial cells. Atherosclerosis 155, 123-130.   DOI
134 Dennedy, M. C., Houlihan, D. D., McMillan, H. and Morrison, J. J. (2002) b2- and b3-Adrenoreceptor agonists: human myometrial selectivity and effects on umbilical artery tone. Am. J. Obstet. Gynecol. 187, 641-647.   DOI
135 de Silva, E. D. and Scheuer, P. J. (1980) Manoalide, an antibiotic sesterterpenoid from the marine sponge luffariella variabilis (polejaeff). Tetrahedron. Lett. 21, 1611-1614.   DOI
136 Donia, M. and Hamann, M. T. (2003) Marine natural products and their potential applications as anti-infective agents. Lancet Infect. Dis. 3, 338-348.   DOI
137 Dunbar, D. C., Rimoldi, J. M., Clark, A. M., Kelly, M. and Hamann, M. T. (2000) Anti-cryptococcal and nitric oxide synthase inhibitory imidazole alkaloids from the calcareous sponge Leucetta cf chagosensis. Tetrahedron 56, 8795-8798.   DOI
138 Edgar, V. A., Cremaschi, G. A., Sterin-Borda, L. and Genaro, A. M. (2002) Altered expression of autonomic neurotransmitter receptors and proliferative responses in lymphocytes from a chronic mild stress model of depression: effects of fluoxetine. Brain Behav. Immun. 16, 333-350.   DOI
139 Elhady, S. S., El-Halawany, A. M., Alahdal, A. M., Hassanean, H. A. and Ahmed, S. A. (2016) A new bioactive metabolite isolated from the red sea marine sponge Hyrtios erectus. Molecules 21, 82.   DOI
140 Elyakov, G. B., Kuznetsova, T., Mikhailov, V. V., Maltsev, I. I., Voinov, V. G. and Fedoreyev, S. A. (1991) Brominated diphenyl ethers from a marine bacterium associated with the sponge Dysidea sp. Experientia 47, 632-633.   DOI
141 Fedoreev, S. A., Prokof'eva, N. G., Denisenko, V. A. and Rebachuk, N. M. (1988) Cytotoxic activity of aaptamines from suberitid marine sponges. Pharm. Chem. J. 22, 615-618.   DOI
142 Faulkner, D. J. (2000) Marine natural products. Nat. Prod. Rep. 17, 7-55.   DOI
143 Faulkner, D. J. (2001) Marine natural products. Nat. Prod. Rep. 18, 1-49.   DOI
144 Faulkner, D. J. (2002) Marine natural products. Nat. Prod. Rep. 19, 1-48.
145 Ford, P. W., Gustafson, K. R., McKee, T. C., Shigematsu, N., Maurizi, L. K., Pannell, L. K., Williams, D. E., De Silva, E. D., Lassota, P., Alien, T. M., Van Soest, R., Andersen, R. J. and Boyd, M. R. (1999) Papuamides A-D, HIV-inhibitory and cytotoxic depsipeptides from the sponges Theonella mirabilis and Theonella swinhoei collected in Papua New Guinea. J. Am. Chem. Soc. 121, 5899-5909.   DOI
146 Frakes, M. A. (2001) Muscle relaxant choices for rapid sequence induction. Air Med. J. 20, 20-21.   DOI
147 Gafni, J., Munsch, J. A., Lam, T. H., Catlin, M. C., Costa, L. G., Molinski, T. F. and Pessah, I. N. (1997) Xestospongins: potent membrane permeable blockers of the inositol 1,4,5-triphosphate receptor. Neuron 19, 723-733.   DOI
148 Garcia-Ruiz, J. C., Amutio, E. and Ponton, J. (2004) Invasive fungal infection in immunocompromised patients. Rev. Iberoam. Micol. 21, 55-62.
149 Gaspar, H., Santos, S., Carbone, M., Rodrigues, A. S., Rodrigues, A. I., Uriz, M. J., Savluchinske Feio, S. M., Melck, D., Humanes, M. and Gavagnin, M. (2008) Isomeric furanosesquiterpenes from the Portuguese marine sponge Fasciospongia sp. J. Nat. Prod. 71, 2049-2052.   DOI
150 Giusiano, G., Mangiaterra, M., Rojas, F. and Gamez, V. (2004) Yeasts species distribution in Neonatal Intensive Care Units in northeast Argentina. Mycoses 47, 300-303.   DOI
151 Giusiano, G., Mangiaterra, M., Rojas, F. and Gamez, V. (2005) Azole Resistance in Neonatal Intensive Care Units in Argentina. J. Chemother. 17, 347-350.   DOI
152 Greve, H., Meis, S., Kassack, M. U., Kehraus, S., Krick, A., Wright, A. D. and Konig, G. M. (2007) New iantherans from the marine sponge Ianthella quadrangulata: novel agonists of the P2Y(11) receptor. J. Med. Chem. 50, 5600-5607.   DOI
153 Griffith, O. W. and Gross, S. S. (1996) Inhibitors of nitric oxide synthases. In Methods in nitric oxide research (J. Stamler and M. Feelish, Ed.), pp. 187-208. Wiley & Sons, New York.
154 Grimwood, K. and Lambert, S. B. (2009) Rotavirus vaccines: opportunities and challenges. Hum. Vaccin. 5, 57-69.   DOI
155 Hadas, E., Shpigel, M. and Ilan, M. (2009) Particulate organic matter as a food source for a coral reef sponge. J. Exp. Biol. 212, 3643-3650.   DOI
156 Hertiani, T., Edrada-Ebel, R., Ortlepp, S., van Soest, R. W., de Voogd, N. J., Wray, V., Hentschel, U., Kozytska, S., Muller, W. E. and Proksch, P. (2010) From anti-fouling to biofilm inhibition: New cytotoxic secondary metabolites from two Indonesian Agelas sponges. Bioorg. Med. Chem. 18, 1297-1311.   DOI
157 Hibbs, R. E. and Zambon, A. C. (2011) Control of muscle spasms and rigidity. Agents acting at the neuromuscular junction and autonomic ganglia. In Goodman & Gilman's the pharmacological basis of therapeutics (L. L. Brunton, B. A. Chabner, B. C. Knollman, Ed.), pp. 266-276. McGraw-Hill, New York.