Chapter 15
Potential Novel Therapeutics: Some Biological Aspects of Marine-derived Bioactive Peptides
Ruvini Liyanage,
Barana C. Jayawardana,
Suranga P. Kodithuwakku,
Ruvini Liyanage
Institute of Fundamental Studies, Kandy, Sri Lanka
Search for more papers by this authorBarana C. Jayawardana
Department of Animal Science, Faculty of Agriculture, University of Peradeniya, Peradeniya, Sri Lanka
Search for more papers by this authorSuranga P. Kodithuwakku
Department of Animal Science, Faculty of Agriculture, University of Peradeniya, Peradeniya, Sri Lanka
Search for more papers by this authorRuvini Liyanage,
Barana C. Jayawardana,
Suranga P. Kodithuwakku,
Ruvini Liyanage
Institute of Fundamental Studies, Kandy, Sri Lanka
Search for more papers by this authorBarana C. Jayawardana
Department of Animal Science, Faculty of Agriculture, University of Peradeniya, Peradeniya, Sri Lanka
Search for more papers by this authorSuranga P. Kodithuwakku
Department of Animal Science, Faculty of Agriculture, University of Peradeniya, Peradeniya, Sri Lanka
Search for more papers by this authorBook Editor(s):Se-Kwon Kim,
Se-Kwon Kim
Marine Bioprocess Research Center, Pukyong National University, Busan, Republic of Korea
Department of Chemistry, Pukyoung National University, Nam-Gu, Busan, Republic of Korea
Search for more papers by this authorSummary
This chapter evaluates some of the marine proteins and peptides that have been isolated and their biological activities, giving special emphasis to their bioactivity and potential use as novel therapeutics for very common human complications, such as hypertension, cancers and viral infections. In order to purify a protein or peptide from the original marine source, a huge quantity of the original source is needed. This particular constraint had driven researchers away from working on the same compound in large numbers in depth. Therefore, it is essential to generate novel aquaculture techniques and biotechnologies encompassing the green technologies in order to produce these sources effectively and with more manageable properties, while at the same time having a minimal impact on the environment. It is essential to find the means of fully or partly synthesizing the desired product as well.
References
- Aherne, G. W., Hardcastle, A., Valenti, M., Bryant, A., Rogers, P., Pettit, G. R., Srirangam, J. K., Kelland, L. R. (1996). Antitumour evaluation of dolastatins 10 and 15 and their measurement in plasma by radioimmunoassay. Cancer Chemother Pharmacol 38, 225–232.
- Alexandre, K. B., Gray, E. S., Mufhandu, H., McMahon, J. B., Chakauya, E., O'Keefe, B. R., Chikwamba, R., Morris, L. (2012). The lectins griffithsin, cyanovirin-N and scytovirin inhibit HIV-1 binding to the DC-SIGN receptor and transfer to CD4(+) cells. Virology, 423, 175–186.
- Alexandre, K. B., Gray, E. S., Pantophlet, R., Moore, P. L., McMahon, J. B., Chakauya, E., O'Keefe, B. R., Chikwamba, R., Morris, L. (2011). Binding of the mannose-specific lectin, griffithsin, to HIV-1 gp120 exposes the CD4-binding site. J Virol 85, 9039–9050.
- Andavan, G. S., Lemmens-Gruber, R. (2010). Cyclodepsipeptides from marine sponges: natural agents for drug research. Mar Drugs, 8, 810–834.
- Anderson, H. J., Coleman, J. E., Andersen, R. J., Roberge, M. (1997). Cytotoxic peptides hemiasterlin, hemiasterlin A and hemiasterlin B induce mitotic arrest and abnormal spindle formation. Cancer Chemother Pharmacol, 39, 223–226.
- Andjelic, C. D., Planelles, V., Barrows, L. R. (2008). Characterizing the anti-HIV activity of papuamide A. Mar Drugs, 6, 528–549.
- Aneiros, A., Garateix, A. (2004). Bioactive peptides from marine sources: pharmacological properties and isolation procedures. J Chromatogr B Analyt Technol Biomed Life Sci, 803, 41–53.
- Astwan, M., Wahyuni, M., Yasuhara, T., Yamada, K., Tadokoro, T., Maekawa, A. (1995). Effects of angiotensin I-converting enzyme inhibitory substances derived from Indonesian dried-salted fish on blood pressure of rats. Bioscience, Biotechnology, and Biochemistry, 59, 425–429.
- Bai, R., Pettit, G. R., Hamel, E. (1990). Dolastatin 10, a powerful cytostatic peptide derived from a marine animal: inhibition of tubulin polymerization mediated through the vinca alkaloid binding domain. Biochem Pharmacol, 39, 1941–1949.
- Banerjee, S., Wang, Z., Mohammad, M., Sarkar, F. H., Mohammad, R. M. (2008). Efficacy of selected natural products as therapeutic agents against cancer. J Nat Prod, 71, 492–496.
- Bewley, C. A., Gustafson, K. R., Boyd, M. R., Covell, D. G., Bax, A., Clore, G. M., Gronenborn, A. M. (1998). Solution structure of cyanovirin-N, a potent HIV-inactivating protein. Nat Struct Biol, 5, 571–578.
- Biscardi, M., Caporale, R., Balestri, F., Gavazzi, S., Jimeno, J., Grossi, A. (2005). VEGF inhibition and cytotoxic effect of aplidin in leukemia cell lines and cells from acute myeloid leukemia. Ann Oncol, 16, 1667–1674.
- Bohlin, L., Goransson, U., Alsmark, C., Weden, C., Backlund, A. (2010). Natural products in modern life science. Phytochem Rev, 9, 279–301.
- Bordenave, S., Fruitier, I., Ballandier, I., Sannier, F., Gildberg, A., Batista, I., Piot, J. M. (2002). HPLC preparation of fish waste hydrolysate fractions. Effect on guinea pig ileum and ACE activity. Preparative Biochemistry and Biotechnology, 32, 65–77.
- Bougatef, A., Nedjar-Arroume, N., Ravallec-Plé, R., Leroy, Y., Guillochon, D., Barkia, A., Nasri, M. (2008). Angiotensin I-converting enzyme (ACE) inhibitory activities of sardinelle(Sardinella aurita) by-products protein hydrolysates obtained by treatment with microbial and visceral fish serine proteases. Food Chemistry, 111, 350–356.
- Bruhn, T., Schaller, C., Schulze, C., Sanchez-Rodriguez, J., Dannmeier, C., Ravens, U., Heubach, J. F., Eckhardt, K., Schmidtmayer, J., Schmidt, H., Aneiros, A., Wachter, E., Beress, L. (2001). Isolation and characterisation of five neurotoxic and cardiotoxic polypeptides from the sea anemone Anthopleura elegantissima. Toxicon, 39, 693–702.
- Byun, H. G., Kim, S. K. (2002). Structure and activity of angiotensin I converting enzyme inhibitory peptides derived from Alaskan pollack skin. J Biochem Mol Biol, 35, 239–243.
- Coleman, J. E., Van Soest, R., Andersen, R. J. (1999). New geodiamolides from the sponge Cymbastela sp. collected in Papua New Guinea. J Nat Prod, 62, 1137–1141.
- Crews, C. M., Collins, J. L., Lane, W. S., Snapper, M. L., Schreiber, S. L. (1994). GTP-dependent binding of the antiproliferative agent didemnin to elongation factor 1 alpha. J Biol Chem, 269, 15411–15414.
- Cuadrado, A., Garcia-Fernandez, L. F., Gonzalez, L., Suarez, Y., Losada, A., Alcaide, V., Martinez, T., Fernandez-Sousa, J. M., Sanchez-Puelles, J. M., Munoz, A. (2003). Aplidin induces apoptosis in human cancer cells via glutathione depletion and sustained activation of the epidermal growth factor receptor, Src, JNK, and p38 MAPK. J Biol Chem, 278, 241–250.
- Cushman, D. W., Cheung, H. S. (1971). Spectrophotometric assay and properties of the angiotensin-converting enzyme of rabbit lung. Biochem Pharmacol, 20, 1637–1648.
- Danve-Szatanek, C., Aymard, M., Thouvenot, D., Morfin, F., Agius, G., Bertin, I., Billaudel, S., Chanzy, B., Coste-Burel, M., Finkielsztejn, L., Fleury, H., Hadou, T., Henquell, C., Lafeuille, H., Lafon, M. E., Le Faou, A., Legrand, M. C., Maille, L., Mengelle, C., Morand, P., Morinet, F., Nicand, E., Omar, S., Picard, B., Pozzetto, B., Puel, J., Raoult, D., Scieux, C., Segondy, M., Seigneurin, J. M., Teyssou, R., Zandotti, C. (2004). Surveillance network for herpes simplex virus resistance to antiviral drugs: 3-year follow-up. J Clin Microbiol, 42, 242–249.
- de Vries, D. J., Beart, P. M. (1995). Fishing for drugs from the sea: status and strategies. Trends Pharmacol Sci, 16, 275–279.
- Edler, M. C., Fernandez, A. M., Lassota, P., Ireland, C. M., Barrows, L. R. (2002). Inhibition of tubulin polymerization by vitilevuamide, a bicyclic marine peptide, at a site distinct from colchicine, the vinca alkaloids, and dolastatin 10. Biochem Pharmacol, 63, 707–715.
- Elion, G. B., Furman, P. A., Fyfe, J. A., de Miranda, P., Beauchamp, L., Schaeffer, H. J. (1977). Selectivity of action of an antiherpetic agent, 9-(2-hydroxyethoxymethyl) guanine. Proc Natl Acad Sci USA, 74, 5716–5720.
- Elion, G. B., Furman, P. A., Fyfe, J. A., de Miranda, P., Beauchamp, L., Schaeffer, H. J. (1999). The selectivity of action of an antiherpetic agent, 9-(2-hydroxyethoxymethyl) guanine. Reproduced from Proc. Natl. Acad. Sci. USA 74, 5716–5720 (1977). Rev Med Virol, 9, 147–152; disc. 152–143.
- Emau, P., Tian, B., O'Keefe, B. R., Mori, T., McMahon, J. B., Palmer, K. E., Jiang, Y., Bekele, G., Tsai, C. C. (2007). Griffithsin, a potent HIV entry inhibitor, is an excellent candidate for anti-HIV microbicide. J Med Primatol, 36, 244–253.
- Enari, H., Takahashi, Y., Kawarasaki, M., Tada, M., Tatsuta, K. (2008). Identification of angiotensin I-converting enzyme inhibitory peptides derived from salmon muscle and their antihypertensive effect. Fisheries Sceince, 74.
- Este, J. A., Telenti, A. (2007). HIV entry inhibitors. Lancet, 370, 81–88.
- Fabian, I., Shur, I., Bleiberg, I., Rudi, A., Kashman, Y., Lishner, M. (1995). Growth modulation and differentiation of acute myeloid leukemia cells by jaspamide. Exp Hematol, 23, 583–587.
- Fahmi, A., Morimura, S., Guo, H. C., Shigematsu, T., Kida, K., Uemura, Y. (2004). Production of angiotensin I converting enzyme inhibitory peptides from sea bream scales. Process in Biochemistry, 39, 1195–1200.
- Falardeau, P., Champagne, P., Poyet, P., Hariton, C., Dupont, E. (2001). Neovastat, a naturally occurring multifunctional antiangiogenic drug, in phase III clinical trials. Semin Oncol, 28, 620–625.
- Ferreira, S. H., Bartelt, D. C., Greene, L. J. (1970). Isolation of bradykinin-potentiating peptides from Bothrops jararaca venom. Biochemistry, 9, 2583–2593.
- Fitzgerald, C., Gallagher, E., Tasdemir, D., and Hayes, M. (2011). Heart health peptides from macroalgae and their potential use in functional foods. Journal of Agriculture and Food Chemistry, 59, 6829–6836.
- Fujii, M., Matsumura, N., Mito, K., Shimizu, T., Kuwahara, M., Sugano, S., Karaki, H. (1993). Antihypertensive effects of peptides in autolysate of bonito bowels on spontaneously hypertensive rats. Biosci Biotechnol Biochem, 57, 2186–2188.
- Fujita, H., Yokoyama, K., Yasumoto, R., Yoshikawa, M. (1995). Antihypertensive effect of thermolysin digest of dried bonito in spontaneously hypertensive rat. Clin Exp Pharmacol Physiol Suppl, 22, S304–305.
- Fujita, H., Yoshikawa, M. (1999). LKPNM: a prodrug-type ACE-inhibitory peptide derived from fish protein. Immunopharmacology, 44, 123–127.
- Gamble, W. R., Durso, N. A., Fuller, R. W., Westergaard, C. K., Johnson, T. R., Sackett, D. L., Hamel, E., Cardellina, J. H. 2nd, Boyd, M. R. (1999). Cytotoxic and tubulin-interactive hemiasterlins from Auletta sp. and Siphonochalina spp. sponges. Bioorg Med Chem, 7, 1611–1615.
- Garber, K. (2005). Peptide leads new class of chronic pain drugs. Nat Biotechnol, 23, 399.
- Geldof, A. A., Mastbergen, S. C., Henrar, R. E., Faircloth, G. T. (1999). Cytotoxicity and neurocytotoxicity of new marine anticancer agents evaluated using in vitro assays. Cancer Chemother Pharmacol, 44, 312–318.
- Goetz, F. W., Planas, J. V., MacKenzie, S. (2004). Tumor necrosis factors. Dev Comp Immunol, 28, 487–497.
- Gonzalez-Santiago, L., Suarez, Y., Zarich, N., Munoz-Alonso, M. J., Cuadrado, A., Martinez, T., Goya, L., Iradi, A., Saez-Tormo, G., Maier, J. V., Moorthy, A., Cato, A. C., Rojas, J. M., Munoz, A. (2006). Aplidin induces JNK-dependent apoptosis in human breast cancer cells via alteration of glutathione homeostasis, Rac1 GTPase activation, and MKP-1 phosphatase downregulation. Cell Death Differ, 13, 1968–1981.
- Grabley, S., Thiericke, R. (1999). Bioactive agents from natural sources: trends in discovery and application. Adv Biochem Eng Biotechnol, 64, 101–154.
- Gul, W., Hamann, M. T. (2005). Indole alkaloid marine natural products: an established source of cancer drug leads with considerable promise for the control of parasitic, neurological and other diseases. Life Sci, 78, 442–453.
- Gulavita, N. K., Pomponi, S. A., Wright, A. E., Garay, M., Sills, M. A. (1995). Aplysillin A, a thrombin receptor antagonist from the marine sponge Aplysina fistularis fulva. J Nat Prod, 58, 954–957.
- Gulavita, N. K., Wright, A. E., McCarthy, P. J., Pomponi, S. A., Kelly-Borges, M., Chin, M., Sills, M. A. (1993). Isolation and structure elucidation of 34-sulfatobastadin 13, an inhibitor of the endothelin A receptor, from a marine sponge of the genus Ianthella. J Nat Prod, 56, 1613–1617.
- Gunasekera, S. P., Pomponi, S. A., McCarthy, P. J. (1994). Discobahamins A and B, new peptides from the Bahamian deep water marine sponge Discodermia sp. J Nat Prod, 57, 79–83.
- Hong, S., Secombes, C. J. (2009). Two peptides derived from trout IL–1beta have different stimulatory effects on immune gene expression after intraperitoneal administration. Comp Biochem Physiol B Biochem Mol Biol, 153, 275–280.
- Hwang, J. S., Ko, W. C. (2004). A novel angiotensin I converting enzyme inhibitory peptide from tuna frame protein hydrolysate and its antihypertensive effect in spontaneously hypertensive rats. Food Chemistry, 118, 96–102.
- Itou, K., Akahane, Y. (2004). Antihypertensive effect of heshiko, a fermented mackerel product, on spontaneously hypertensive rats. Fisheries Science, 70, 1121–1129.
- Itou, K., Nagahashi, R., Saitou, M., Akahane, Y. (2007). Antihypertensive effect of Narezushi, a fermented mackerel product, on spontaneously hypertensive rats. Fisheries Science, 73, 1344–1352.
- Jacobsen, R. B., Jimenez, E. C., De la Cruz, R. G., Gray, W. R., Cruz, L. J., Olivera, B. M. (1999). A novel D-leucine-containing Conus peptide: diverse conformational dynamics in the contryphan family. J Pept Res, 54, 93–99.
- Je, J. Y., Park, J. Y., Jung, W. K., Park, P. J., Kim, S. K. (2005a). Isolation of angiotensin I converting enzyme (ACE) inhibitor from fermented oyster sauce, Crassostrea gigas. Food Chemistry, 90, 809–814.
- Je, J. Y., Park, P. J., Byun, H. G., Jung, W. K., Kim, S. K. (2005b). Angiotensin I converting enzyme (ACE) inhibitory peptide derived from the sauce of fermented blue mussel, Mytilus edulis. Bioresour Technol, 96, 1624–1629.
- Je, J. Y., Park, P. J., Kwon, J. Y., Kim, S. K. (2004). A novel angiotensin I converting enzyme inhibitory peptide from Alaska pollack (Theragra chalcogramma) frame protein hydrolysate. J Agric Food Chem, 52, 7842–7845.
- Jeon, Y. J., Byun, H. G., Kim, S. K. (1999). Improvement of functional properties of cod frame protein hydrolysates using ultrafiltration membranes. Process in Biochemistry, 35, 471–478.
- Jung, W. K., Mendis, E., Je, J. Y., Park, P. J., Son, B. W., Kim, H. C., Choi, Y. K., Kim, S. K. (2006). Angiotensin I-converting enzyme inhibitory peptide from yellow fin sole (Limanda aspera) frame protein and its antihypertensive effect in spontaneously hypertensive rats. Food Chemistry, 94, 26–32.
- Kaul, P. N., Daftari, P. (1986). Marine pharmacology: bioactive molecules from the sea. Annu Rev Pharmacol Toxicol, 26, 117–142.
- Kawasaki, T., Seki, E., Osajima, K., Yoshida, M., Asada, K., Matsui, T., Osajima, Y. (2000). Antihypertensive effect of valyl-tyrosine, a short chain peptide derived from sardine muscle hydrolyzate, on mild hypertensive subjects. J Hum Hypertens, 14, 519–523.
- Keeffe, J. R., Gnanapragasam, P. N., Gillespie, S. K., Yong, J., Bjorkman, P. J., Mayo, S. L. (2011). Designed oligomers of cyanovirin-N show enhanced HIV neutralization. Proc Natl Acad Sci USA, 108, 14079–14084.
- Kikuchi, M., Watanabe, Y., Tanaka, M., Akaji, K., Konno, H. (2011). Synthesis and cytotoxicity of the depsipeptides analogues of callipeltin B. Bioorg Med Chem Lett, 21, 4865–4868.
- Kobayashi, M., Natsume, T., Tamaoki, S., Watanabe, J., Asano, H., Mikami, T., Miyasaka, K., Miyazaki, K., Gondo, M., Sakakibara, K., Tsukagoshi, S. (1997). Antitumor activity of TZT-1027, a novel dolastatin 10 derivative. Jpn J Cancer Res, 88, 316–327.
- Kouno, K., Hirano, S., Kuboki, H., Kasai, M., Hatae, K. (2005). Effects of dried bonito (katsuobushi) and captopril, an angiotensin I-converting enzyme inhibitor, on rat isolated aorta: a possible mechanism of antihypertensive action. Biosci Biotechnol Biochem, 69, 911–915.
- Krishnaveni, M., Jayachandran, S. (2009). Inhibition of MAP kinases and down regulation of TNF-alpha, IL-beta and COX-2 genes by the crude extracts from marine bacteria. Biomed Pharmacother, 63, 469–476.
- Lee, J. K., Hong, S., Jeon, J. K., Kim, S. K., Byun, H. G. (2009). Purification and characterization of angiotensin I converting enzyme inhibitory peptides from the rotifer, Brachionus rotundiformis. Bioresource Technology, 100, 5255–5259.
- Lee, S. H., Qian, Z. J., Kim, S. K. (2010). A novel angiotensin I converting enzyme inhibitory peptide from tuna frame protein hydrolysate and its antihypertensive effect in spontaneously hypertensive rats. Food Chemistry, 118, 96–102.
- Liang, J., Moore, R. E., Moher, E. D., Munroe, J. E., Al-awar, R. S., Hay, D. A., Varie, D. L., Zhang, T. Y., Aikins, J. A., Martinelli, M. J., Shih, C., Ray, J. E., Gibson, L. L., Vasudevan, V., Polin, L., White, K., Kushner, J., Simpson, C., Pugh, S., Corbett, T. H. (2005). Cryptophycins-309, 249 and other cryptophycin analogs: preclinical efficacy studies with mouse and human tumors. Invest New Drugs, 23, 213–224.
- Lu, K., Dempsey, J., Schultz, R. M., Shih, C., Teicher, B. A. (2001). Cryptophycin-induced hyperphosphorylation of Bcl-2, cell cycle arrest and growth inhibition in human H460 NSCLC cells. Cancer Chemother Pharmaco,l 47, 170–178.
- Lu, Z., Van Wagoner, R. M., Harper, M. K., Baker, H. L., Hooper, J. N., Bewley, C. A., Ireland, C. M. (2011). Mirabamides E-H, HIV-inhibitory depsipeptides from the sponge Stelletta clavosa. J Nat Prod, 74, 185–193.
- Makarieva, T. N., Tabakmaher, K. M., Guzii, A. G., Denisenko, V. A., Dmitrenok, P. S., Shubina, L. K., Kuzmich, A. S., Lee, H. S., Stonik, V. A. (2011). Monanchocidins B-E: polycyclic guanidine alkaloids with potent antileukemic activities from the sponge Monanchora pulchra. J Nat Prod, 74, 1952–1958.
- Marchbank, T., Elia, G., Playford, R. J. (2009). Intestinal protective effect of a commercial fish protein hydrolysate preparation. Regul Pept, 155, 105–109.
- Marchbank, T., Limdi, J. K., Mahmood, A., Elia, G., Playford, R. J. (2008). Clinical trial: protective effect of a commercial fish protein hydrolysate against indomethacin (NSAID)-induced small intestinal injury. Aliment Pharmacol Ther, 28, 799–804.
- Matsui, T., Matsufuji, H., Seki, E., Osajima, K., Nakashima, M., Osajima, Y. (1993). Inhibition of angiotensin I-converting enzyme by Bacillus licheniformis alkaline protease hydrolyzates derived from sardine muscle. Biosci Biotechnol Biochem, 57, 922–925.
- Matsumoto, K., Ogikubo, A., Yoshino, T., Matsui, T., Osajima, Y. (1994). Separation and purification of angiotensin-I convertingenzyme inhibitory peptide in peptic hydrolyzate of oyster. Journal of Japanese Society of Food Science and Technology, 41, 589–594.
- Mayer, A. M., Gustafson, K. R. (2003). Marine pharmacology in 2000, antitumor and cytotoxic compounds. Int J Cancer, 105, 291–299.
- Mayer, A. M., Gustafson, K. R. (2004). Marine pharmacology in 2001–2, antitumour and cytotoxic compounds. Eur J Cancer, 40, 2676–2704.
- Mayer, A. M., Gustafson, K. R. (2006). Marine pharmacology in 2003–2004, anti-tumour and cytotoxic compounds. Eur J Cancer, 42, 2241–2270.
- Mayer, A. M., Gustafson, K. R. (2008). Marine pharmacology in 2005–2006, antitumour and cytotoxic compounds. Eur J Cancer, 44, 2357–2387.
- 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. Comp Biochem Physiol C Toxicol Pharmacol, 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. Biochim Biophys Acta, 1790, 283–308.
- McIntosh, J. M., Olivera, B. M., Cruz, L. J. (1999). Conus peptides as probes for ion channels. Methods Enzymol, 294, 605–624.
- Meuleman, P., Albecka, A., Belouzard, S., Vercauteren, K., Verhoye, L., Wychowski, C., Leroux-Roels, G., Palmer, K. E., Dubuisson, J. (2011). Griffithsin has antiviral activity against hepatitis C virus. Antimicrob Agents Chemother, 55, 5159–5167.
- Micewicz, E. D., Cole, A. L., Jung, C. L., Luong, H., Phillips, M. L., Pratikhya, P., Sharma, S., Waring, A. J., Cole, A. M., Ruchala, P. (2010). Grifonin-1, a small HIV-1 entry inhibitor derived from the algal lectin, Griffithsin. PLoS One, 5, e14360.
- Molinski, T. F., Dalisay, D. S., Lievens, S. L., Saludes, J. P. (2009). Drug development from marine natural products. Nat Rev Drug Discov, 8, 69–85.
- Morfin, F., Thouvenot, D. (2003). Herpes simplex virus resistance to antiviral drugs. J Clin Virol, 26, 29–37.
- Mori, T., O'Keefe, B. R., Sowder, R. C. 2nd, Bringans, S., Gardella, R., Berg, S., Cochran, P., Turpin, J. A., Buckheit, R. W. Jr, McMahon, J. B., Boyd, M. R. (2005). Isolation and characterization of griffithsin, a novel HIV-inactivating protein, from the red alga Griffithsia sp. J Biol Chem, 280, 9345–9353.
- Nagai, T., Suzuki, N., Nagashima, T. (2006). Antioxidative activities and angiotensin I-converting enzyme inhibitory activities of enzymatic hydrolysates from commercial kamaboko type samples. Food Science and Technology International, 12, 335–346.
- Nakao, Y., Fusetani, N. (2007). Enzyme inhibitors from marine invertebrates. J Nat Prod, 70, 689–710.
- Negri, A., Marco, E., Garcia-Hernandez, V., Domingo, A., Llamas-Saiz, A. L., Porto-Sanda, S., Riguera, R., Laine, W., David-Cordonnier, M. H., Bailly, C., Garcia-Fernandez, L. F., Vaquero, J. J., Gago, F. (2007). Antitumor activity, X-ray crystal structure, and DNA binding properties of thiocoraline A, a natural bisintercalating thiodepsipeptide. J Med Chem, 50, 3322–3333.
- Odaka, C., Sanders, M. L., Crews, P. (2000). Jasplakinolide induces apoptosis in various transformed cell lines by a caspase-3-like protease-dependent pathway. Clin Diagn Lab Immunol, 7, 947–952.
- Oku, N., Gustafson, K. R., Cartner, L. K., Wilson, J. A., Shigematsu, N., Hess, S., Pannell, L. K., Boyd, M. R., McMahon, J. B. (2004). Neamphamide A, a new HIV-inhibitory depsipeptide from the Papua New Guinea marine sponge Neamphius huxleyi. J Nat Prod, 67, 1407–1411.
- Olivera, B. M., Gray, W. R., Zeikus, R., McIntosh, J. M., Varga, J., Rivier, J., de Santos, V., Cruz, L. J. (1985). Peptide neurotoxins from fish-hunting cone snails. Science, 230, 1338–1343.
- Olivera, B. M., Cruz, L. J., de Santos, V., LeCheminant, G. W., Griffin, D., Zeikus, R., McIntosh, J. M., Galyean, R., Varga, J., Gray, W. R. et al. (1987). Neuronal calcium channel antagonists. Discrimination between calcium channel subtypes using omega-conotoxin from Conus magus venom. Biochemistry, 26, 2086–2090.
- Olivera, B. M., Cruz, L. J., Yoshikami, D. (1999a). Effects of Conus peptides on the behavior of mice. Curr Opin Neurobiol, 9, 772–777.
- Olivera, B. M., Walker, C., Cartier, G. E., Hooper, D., Santos, A. D., Schoenfeld, R., Shetty, R., Watkins, M., Bandyopadhyay, P., Hillyard, D. R. (1999b). Speciation of cone snails and interspecific hyperdivergence of their venom peptides. Potential evolutionary significance of introns. Ann N Y Acad Sci 870, 223–237.
- Ono, S., Hosokawa, M., Miyashita, K., Takahashi, K. (2003). Isolation of peptides with Angiotensin I-converting enzyme inhibitory effect derived from hydrolysate of upstream chum salmon muscle. Journal of Food Science, 74, 1611–1614.
- Ono, S., Hosokawa, M., Miyashita, K., Takahashi, K. (2006). Inhibition properties of dipeptides from salmon muscle hydrolysate on angiotensin I-converting enzyme. International Journal of Food Science & Technology, 41, 383–386.
- Ortega-Morales, B. O., Chan-Bacab, M. J., Miranda-Tello, E., Fardeau, M. L., Carrero, J. C., Stein, T. (2008). Antifouling activity of sessile bacilli derived from marine surfaces. J Ind Microbiol Biotechnol, 35, 9–15.
- Ovenden, S. P., Nielson, J. L., Liptrot, C. H., Willis, R. H., Tapiolas, D. M., Wright, A. D., Motti, C. A. (2011). Metachromins U-W: cytotoxic merosesquiterpenoids from an Australian specimen of the sponge Thorecta reticulata. J Nat Prod, 74, 1335–1338.
- Park, C. H., Kim, H. J., Kang, K. T., Park, J. W., Kim, J. S. (2009). Fractionation and angiotensin I-converting enzyme (ACE) inhibitory activity of gelatin hydrolysates from by-products of Alaska Pollock surimi. Journal of Fisheries and Aquaculture Science, 12, 79–85.
- Pettit, G. R. (1997). The dolastatins. Fortschr Chem Org Naturst, 70, 1–79.
- Pettit, G. R., Hogan, F., Xu, J. P., Tan, R., Nogawa, T., Cichacz, Z., Pettit, R. K., Du, J., Ye, Q. H., Cragg, G. M., Herald, C. L., Hoard, M. S., Goswami, A., Searcy, J., Tackett, L., Doubek, D. L., Williams, L., Hooper, J. N., Schmidt, J. M., Chapuis, J. C., Tackett, D. N., Craciunescu, F. (2008). Antineoplastic agents. 536. New sources of naturally occurring cancer cell growth inhibitors from marine organisms, terrestrial plants, and microorganisms (1a). J Nat Prod, 71, 438–444.
- Plaza, A., Gustchina, E., Baker, H. L., Kelly, M., Bewley, C. A. (2007). Mirabamides A-D, depsipeptides from the sponge Siliquariaspongia mirabilis that inhibit HIV-1 fusion. J Nat Prod, 70, 1753–1760.
- Prasad, P., Aalbersberg, W., Feussner, K. D., Van Wagoner, R. M. (2011). Papuamides E and F, cytotoxic depsipeptides from the marine sponge Melophlus sp. Tetrahedron, 67, 8529–8531.
- Qian, Z. J., Je, J. Y., Kim, S. K. (2007). Antihypertensive effect of angiotensin I converting enzyme-inhibitory peptide from hydrolysates of bigeye tuna dark muscle, Thunnus obesus. Journal of Agricultural and Food Chemistry, 55, 8398–8403.
- Rao, P. V., Gupta, N., Bhaskar, A. S., Jayaraj, R. (2002). Toxins and bioactive compounds from cyanobacteria and their implications on human health. J Environ Biol, 23, 215–224.
- Rashid, M. A., Gustafson, K. R., Boswell, J. L., Boyd, M. R. (2000). Haligramides A and B, two new cytotoxic hexapeptides from the marine sponge Haliclona nigra. J Nat Prod, 63, 956–959.
- Rashid, M. A., Gustafson, K. R., Cartner, L. K., Shigematsu, N., Pannell, L. K., Boyd, M. R. (2001). Microspinosamide, a new HIV-inhibitory cyclic depsipeptide from the marine sponge Sidonops microspinosa. J Nat Prod, 64, 117–121.
- Rawat, D. S., Joshi, M. C., Joshi, P., Atheaya, H. (2006). Marine peptides and related compounds in clinical trial. Anticancer Agents Med Chem, 6, 33–40.
- Rho, S. J., Lee, J. S., Chung, Y. I., Kim, Y. W., Lee, H. G. (2009). Purification and identification of an angiotensin I-converting enzyme inhibitory peptide from fermented soybean extract. Process in Biochemistry, 44, 490–493.
- Rinehart, K. L. Jr, Gloer, J. B., Hughes, R. G. Jr, Renis, H. E., McGovren, J. P., Swynenberg, E. B., Stringfellow, D. A., Kuentzel, S. L., Li, L. H. (1981). Didemnins: antiviral and antitumor depsipeptides from a caribbean tunicate. Science 212, 933–935.
- Rinehart, K. L., Kishore, V., Bible, K. C., Sakai, R., Sullins, D. W., Li, K. M. (1988a). Didemnins and tunichlorin: novel natural products from the marine tunicate Trididemnum solidum. J Nat Prod, 51, 1–21.
- Rinehart, K. L., Kishore, V., Bible, K. C., Sakai, R., Sullins, D. W., Li, K. M. (1988b). Erratum—‘didemnins and tunichlorin: novel natural products from the marine tunicate trididemnum solidum’. J Nat Prod, 51, 624.
- Rivier, J., Galyean, R., Gray, W. R., Azimi-Zonooz, A., McIntosh, J. M., Cruz, L. J., Olivera, B. M. (1987). Neuronal calcium channel inhibitors: synthesis of omega-conotoxin GVIA and effects on 45Ca uptake by synaptosomes. J Biol Chem, 262, 1194–1198.
- Sagar, S., Kaur, M., Minneman, K. P. (2010). Antiviral lead compounds from marine sponges. Mar Drugs, 8, 2619–2638.
- Sakai, R., Rinehart, K. L., Guan, Y., Wang, A. H. (1992). Additional antitumor ecteinascidins from a Caribbean tunicate: crystal structures and activities in vivo. Proc Natl Acad Sci USA, 89, 11456–11460.
- Sato, K., Horibe, K., Amano, K., Mitusi-Saito, M., Hori, M., Matsunaga, S., Fusetani, N., Ozaki, H., Karaki, H. (2001). Membrane permeabilization induced by discodermin A, a novel marine bioactive peptide. Toxicon, 39, 259–264.
- Sauerbrei, A., Deinhardt, S., Zell, R., Wutzler, P. (2010). Testing of herpes simplex virus for resistance to antiviral drugs. Virulence, 1, 555–557.
- Shan, J., Ogawa, Y., Watabe, T., Morimoto, R., Oota, S., Seiki, M., Miyamoto, T. (2007). Angiotensin I-converting enzyme inhibitory activity of fermented surimi by lactic acid bacteria. Journal of the Japanese Society of Food Sciene and Technology—Nippon Shokukin Kagaku Kogaku Kaishi, 54, 160–166.
- Sheih, I. C., Fang, T. J., Wu, T. K. (2009). Isolation and characterization of a novel angiotensin I-converting enzyme (ACE) inhibitory peptide from the algae protein waste. Food Chemistry, 115, 279–284.
- Shih, C., Teicher, B. A. (2001). Cryptophycins: a novel class of potent antimitotic antitumor depsipeptides. Curr Pharm Des, 7, 1259–1276.
- Shiozaki, K., Shiozaki, M., Masuda, J., Yamauchi, A., Ohwada, S., Nakano, T., Yamaguchi, T., Saito, T., Muramoto, K., Sato, M. (2010). Identification of oyster-derived hypotensive peptide acting as angiotensin-I-converting enzyme inhibitor. Fisheries Science, 76, 865–872.
- Simmons, T. L., Andrianasolo, E., McPhail, K., Flatt, P., Gerwick, W. H. (2005). Marine natural products as anticancer drugs. Mol Cancer Ther, 4, 333–342.
- Smith, J. R., Rayner, C. R., Donner, B., Wollenhaupt, M., Klumpp, K., Dutkowski, R. (2011). Oseltamivir in seasonal, pandemic, and avian influenza: a comprehensive review of 10-years clinical experience. Adv Ther, 28, 927–959.
- Suetsuna, K. N. T. (1986). Identification of an antihypertensive peptide from peptic digest of wakame (Undaria pinnatifida). Journal of Nutritional Biochemistry, 11, 450–454.
- Suetsuna, K. N. T. (2000). Identification of an antihypertensive peptide from peptic digest of wakame (Undaria pinnatifida). J ournal of Nutritional Biochemistry, 11, 450–454.
- Sugiyama, K., Takada, K., Egawa, M., Yamamoto, I., Onzuka, H., Oba, K. (1991). Hypotensive effect of fish-protein hydrolysate. Journal of the Japan Society for Bioscience Biotechnology and Agrochemistry—Nippon Nogeikagaku Kaishi, 65, 35–43.
- Sugumaran, M., Robinson, W. E. (2010). Bioactive dehydrotyrosyl and dehydrodopyl compounds of marine origin. Mar Drugs, 8, 2906–2935.
- Sun, H. F., Li, X. M., Meng, L., Cui, C. M., Gao, S. S., Li, C. S., Huang, C. G., Wang, B. G. (2012). Asperolides A-C, tetranorlabdane diterpenoids from the marine alga-derived endophytic fungus Aspergillus wentii EN-48. J Nat Prod, 75, 148–152.
- Tamura, K., Nakagawa, K., Kurata, T., Satoh, T., Nogami, T., Takeda, K., Mitsuoka, S., Yoshimura, N., Kudoh, S., Negoro, S., Fukuoka, M. (2007). Phase I study of TZT-1027, a novel synthetic dolastatin 10 derivative and inhibitor of tubulin polymerization, which was administered to patients with advanced solid tumors on days 1 and 8 in 3-week courses. Cancer Chemother Pharmacol, 60, 285–293.
- Tanabe, K., Lamping, E., Adachi, K., Takano, Y., Kawabata, K., Shizuri, Y., Niimi, M., Uehara, Y. (2007). Inhibition of fungal ABC transporters by unnarmicin A and unnarmicin C, novel cyclic peptides from marine bacterium. Biochem Biophys Res Commun, 364, 990–995.
- Tsai, C. C., Emau, P., Jiang, Y., Agy, M. B., Shattock, R. J., Schmidt, A., Morton, W. R., Gustafson, K. R., Boyd, M. R. (2004). Cyanovirin-N inhibits AIDS virus infections in vaginal transmission models. AIDS Res Hum Retroviruses, 20, 11–18.
- Tsai, J. S., Chen, J. L., Pan, B. S. (2008). ACE-inhibitory peptides identified from the muscle protein hydrolysate of hard clam (Meretrix lusoria). Process in Biochemistry, 43, 743–747.
- Tziveleka, L. A., Vagias, C., Roussis, V. (2003). Natural products with anti-HIV activity from marine organisms. Curr Top Med Chem, 3, 1512–1535.
- Vera, M. D., Joullie, M. M. (2002). Natural products as probes of cell biology: 20 years of didemnin research. Med Res Rev, 22, 102–145.
- Vercruysse, L., Van Camp, J., Smagghe, G. (2005). ACE inhibitory peptides derived from enzymatic hydrolysates of animal muscle protein: a review. J Agric Food Chem, 53, 8106–8115.
- Vijaykrishna, D., Smith, G. J., Pybus, O. G., Zhu, H., Bhatt, S., Poon, L. L., Riley, S., Bahl, J., Ma, S. K., Cheung, C. L., Perera, R. A., Chen, H., Shortridge, K. F., Webby, R. J., Webster, R. G., Guan, Y., Peiris, J. S. (2011). Long-term evolution and transmission dynamics of swine influenza A virus. Nature, 473, 519–522.
- Vo, T. S., Kim, S. K. (2010). Potential anti-HIV agents from marine resources: an overview. Mar Drugs, 8, 2871–2892.
- Wang, Y. K., He, H. L., Chen, X. L., Sun, C. Y., Zhang, Y. Z., Zhou, B. C. (2008). Production of novel angiotensin I-converting enzyme inhibitory peptides by fermentation of marine shrimp Acetes chinensis with Lactobacillus fermentum SM 605. Appl Microbiol Biotechnol, 79, 785–791.
- Wang, Y. K., He, H. L., Wang, G. F., Wu, H., Zhou, B. C., Chen, X. L., Zhang, Y. Z. (2010). Oyster (Crassostrea gigas) hydrolysates produced on a plant scale have antitumor activity and immunostimulating effects in BALB/c mice. Mar Drugs, 8, 255–268.
- Watanabe, J., Minami, M., Kobayashi, M. (2006). Antitumor activity of TZT-1027 (Soblidotin). Anticancer Res, 26, 1973–1981.
- Wijesekara, I., Kim, S. K. (2010). Angiotensin-I-converting enzyme (ACE) inhibitors from marine resources: prospects in the pharmaceutical industry. Mar Drugs, 8, 1080–1093.
- Wu, H., He, H. L., Chen, X. L., Sun, C. Y., Zhang, Y. Z., Zhou, B. C. (2008). Purification and identification of novel angiotensin-I-converting enzyme inhibitory peptides from shark meat hydrolysate. Process in Biochemistry, 43, 457–461.
- Yamamoto, N., Andoh, M., Kawahara, M., Fukuoka, M., Niitani, H. (2009). Phase I study of TZT-1027, a novel synthetic dolastatin 10 derivative and inhibitor of tubulin polymerization, given weekly to advanced solid tumor patients for 3 weeks. Cancer Sci, 100, 316–321.
- Yasuhara-Bell, J., Lu, Y. (2010). Marine compounds and their antiviral activities. Antiviral Res, 86, 231–240.
- Yokoyama, K., Chiba, H., Yoshikawa, M. (1992). Peptide inhibitors for angiotensin I-converting enzyme from thermolysin digest of dried bonito. Biosci Biotechnol Biochem, 56, 1541–1545.
- Yoshikawa, M., Fujita, H., Matoba, N., Takenaka, Y., Yamamoto, T., Yamauchi, R., Tsuruki, H., Takahata, K. (2000). Bioactive peptides derived from food proteins preventing lifestyle-related diseases. Biofactors, 12, 143–146.
- Zhao, Y., Li, B., Dong, S., Liu, Z., Zhao, X., Wang, J., Zeng, M. (2009). A novel ACE inhibitory peptide isolated from Acaudina molpadioidea hydrolysate. Peptides, 30, 1028–1033.
- Zhao, Y., Li, B., Liu, Z., Dong, S., Zhao, X., Zeng, M. (2007). Antihypertensive effect and purification of an ACE inhibitory peptide from seaz cucumber gelatin hydrolysate. Process in Biochemistry, 42, 1586–1591.
- Zheng, L. H., Wang, Y. J., Sheng, J., Wang, F., Zheng, Y., Lin, X. K., Sun, M. (2011). Antitumor peptides from marine organisms. Mar Drugs, 9, 1840–1859.
