Medicinal and pharmaceutical uses of seaweed natural products: A review

Journal of Applied Phycology

Volumn 16, Issue 4, 2004, Pages 245-262

  Smit, Albertus J ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

biological activity; macroalga; medicine; pharmaceuticals; pharmacology; seaweeds

Indexed keywords

MEDICINAL PLANT; SEAWEED;

ALGAE; BRYOPSIS; CHLOROPHYTA; DELISEA; DELISEA PULCHRA; EUKARYOTA; PHAEOPHYCEAE; RHODOPHYTA;

EID: 8744287436     PISSN: 09218971     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:JAPH.0000047783.36600.ef     Document Type: Review

References (199)

1. Abe S, Kaneda T (1975) Studies on the effects of marine products on cholesterol metabolism in rats. XI. isolation of a new betaine, ulvaline, from a green laver Monostroma nitidum and its depressing effect on plasma cholesterol levels. Bull. Japan Soc. Fish. 41: 567-571.
2. Al Hassan JM, Ali M, Thomson M, Fatima T, Gubler CJ, Criddle RS (1987) Prostaglandin associated mortality following intravenous injection of catfish epidermal secretions in rabbits. Prosta. Leukotr. Med. 28: 95-102.
3. Angulo Y, Lomonte B (2003) Inhibitory effect of fucoidan on the activities of crotaline snake venom myotoxic phospholipases A(2). Biochem Pharmacol. 66: 1993-2000.
4. Ara J, Sultana V, Qasim Rahmad VU (2002) Hypolipidaemic activity of seaweed from Karachi coast. Phytother. Res. 16: 479-483.
5. Baba M, Snoeck R, Pauwels R, De Clercq E (1988) Sulfated polysaccharides are potent and selective inhibitors of various enveloped viruses, including herpes simplex virus, cytomegalovirus, vesicular stromatitis virus, and human immunodeficiency virus. Antimicrob. Agents Chemother. 32: 1742-1745.
6. Barbier P, Guise S, Huitorel P, Amade P, Pesando D, Briand C, Peyrot V (2001) Caulerpenyne from Caulerpa taxifolia has an antiproliferative activity on tumor cell line SK-N-SH and modifies the microtubule network. Life Sci. 70: 415-429.
7. Barcelo A, Claustre J, Moro F, Chayvaille JA, Cuber JC, Plaisancie P (2000) Mucin secretion is modulated by luminal factors in the isolated vascularly perfused rat colon. Gut 46: 218-224.
8. Barriault L, Boulet SL, Fujiwara K, Murai A, Paquette LA (1999) Synthesis and biological evaluation of analogs of the marine toxin polycavernoside A. Bioorg. Med. Chem. Lett. 9: 2069-2072.
9. Bates S (1998) Ecophysiology and metabolism of ASP toxin production. In Anderson DM, Cembella AD, Hallegraeff GM (eds), Physiological Ecolology of Harmful Algal Blooms, Springer-Verlag, Heidelberg, pp. 405-426.
10. Bates S (2000) Domoic-acid-producing diatoms: another genus added! J. Phycol. 36: 978-985.
11. Ben-Ari Y, Cossart R (2000) Kainate, a double agent that generates seizures: two decades of progress. Trends Neurosci. 23: 580-587.
12. Benevides NMB, Holanda ML, Melo FR, Freitas ALP, Sampaio AH (1998) Purification and partial characterisation of the lectin from the marine red alga Enantiocladia duperreyi (C. Agardh) Falkenberg. Bot. Mar. 41: 521-525.
13. Bird KT, Chiles TC, Longley RE, Kendrick AF, Kinkema MD (1992) Agglutinins from marine macroalgae of the southeastern United States. J. Appl. Phycol. 5: 213-218.
14. Bitou N, Ninomiya M, Tsujita T, Okuda H (1999) Screening of lipase inhibitors from marine algae. Lipids 34: 441-445.
15. Blumenthal PD (1988) Prospect comparison of Dilapan and Laminaria for pretreatment of the cervix in second trimester induction of abortion. Obstet. Gynecol. 72: 243-246.
16. Bond GR, van Zee A (1994) Overdosage of misoprostol in pregnancy. Am. J. Obstet. Gynecol. 171: 561-562.
17. Boyd WC, Reguera RM (1949) Hemagglutinating substances in various plants. J. Immunol. 62: 333-339.
18. Buckle PJ, Baldo BA, Taylor KM (1980) The anti-inflammatory activity of marine natural products-6-n-tridecylsalicylic acid, flexibilide and dendalone 3-hydroxybutyrate. Agents and Actions. 10: 361-367.
19. Cáceres PJ, Carlucci MJ, Damonte EB, Matsuhiro B, Zúñiga EA (2000) Carrageenans from Chilean samples of Stenogramme intermpta (Phyllophoraceae): Structural analysis and biological activity. Phytochemistry 53: 81-86.
20. Carcache LM, Rodriguez J, Rein KS (2003) The structural basis for kainoid selectivity at AMPA receptors revealed by low-mode docking calculations. Bioorg. Med. Chem. 11: 551-559.
21. Carlucci MJ, Ciancia M, Matulewicz MC, Cerezo AS, Damonte EB (1999a) Antiherpetic activity and mode of action of natural carrageenans of diverse structural types. Antivir. Res. 43: 93-102.
22. Carlucci MJ, Pujol CA, Ciancia M, Noseda MD, Matulewicz MC, Damonte EB, Cerezo AS (1997) Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: correlation between structure and biological activity. Int. J. Biol. Macromol 20: 97-105.
23. Carlucci MJ, Scolaro LA, Damonte EB (1999b) Inhibitory action of natural carrageenans on Herpes simplex virus infection of mouse astrocytes. Chemotheraphy 45: 429-436.
24. Carthew P (2002) Safety of carrageenan in foods. Env. Health Perspect. 110: A176.
25. Chapman VJ (1970) Seaweeds and Their Uses, 2nd edn, The Camelot Press Ltd., London, 304 pp.
26. Chen H, Sun P, Song Q (1995) Lectins, a powerful defensive weapon of aquatic animals. J. Oceanogr. Huanghai Bohai Seas 13: 61-71.
27. Chen J, Gerwick WH, Shatzman R, Laney M (1994) Isorawsonol and related TMP dehydrogenase inhibitors from the tropical green alga Avminvillea rawsonii. J. Nat. Prod. 57: 947-952.
28. Chertkov KS, Davydova SA, Nesterova TA, Zviagintseva TN, Eliakova LA (1999) Efficiency of polysaccharide translam for early treatment of acute radiation illness. Radiats Biol Radioecol. 39: 572-577.
29. Church FC, Meade JB, Treanor RE, Whinna HC (1989) Antithrombin activity of fucoidan. J. biol. Chem. 264: 3618-3623.
30. Cisar JO, Sandberg AL, Abeygunawardana C, Reddy GP, Bush CA (1995) Lectin recognition of host-like saccharide motifs in streptococcal cell wall polysaccharides. Glycobiol. 5: 655-662.
31. Colliec S, Fischer AM, Tapon-Bretaudiere, J, Boisson C, Durand P, Jozefonvicz J (1991) Anticoaggulant properties of a fucoidan fraction. Thromb. Res. 64: 143-154.
32. Coombe DR, Parish CR, Ramshaw IE, Snowden JM (1987) Analysis of the inhibition of tumour metastasis by sulphated polysaccharides. Int. J. Cancer 39: 82-88.
33. Cordell GA (2000) Biodiversity and drug discovery - a symbiotic relationship. Phytochemistry 55: 463-480.
34. Culioli G, Daoudi M, Ortalo-Magne A, Valls R, Piovetti L (2001) (S)-12-hydroxygeranylgeraniol-derived diterpenes from the brown alga Bifurcaria bifurcata. Phytochemistry 57: 529-535.
35. Dalmo RA, Bogwald J, Ingebrigtsen K, Seljelid R (1996) The immunomodulatory effect of laminaran [β-(1,3)-D-glucan] on Atlantic salmon, Salmo salar L., anterior kidney leucocytes after intraperitoneal, peroral and peranal administration. J. Fish Dis. 19: 449-457.
36. Dalmo RA, Seljelid R (1995) The immunomodulatory effect of LPS, laminaran and sulphated laminaran [β-(1,3)-D-glucan] on Atlantic salmon, Salmo salar L., macrophages in vitro. J. Fish Dis. 18: 175-185.
37. Damonte EB, Neyts J, Pujol CA, Snoeck R, Andrei G, Ikeda S, Witvrouw M, Reymen D, Haines H, Matulewicz MC, Cerezo A, Coto CE, De Clercq E (1994) Antiviral activity of a sulfated polysaccharide from the red seaweed Nothogenia fastigiata. Biochem. Pharmacol. 47: 2187-2192.
38. Dannhardt G, Kiefer W (2001) Cyclooxygenase inhibitors - current status and future prospects. Eur. J. Med. Chem. 36: 109-126.
39. Davies LP, Jamieson DD, Baird-Lambert JA, Kazlauskas R (1984) Halogenated pyrrolopyrimidine analogues of adenosine from marine organisms: pharmacological activities and potent inhibition of adenosine kinase. Biochem. Pharmacol. 33: 347-355.
40. Davyt D, Entz W, Fernandez R, Mariezcurrena R, Mombru AW, Saldana J, Dominguez L, Coll J, Manta E (1998) A new indole derivative from the red alga Chondria atropurpurea. Isolation, structure determination, and anthelmintic activity. J. Nat. Prod. 61: 1560-1563.
41. Davyt D, Fernandez R, Suescun L, Mombru AW, Saldana J, Dominguez L, Coll J, Fujii MT, Manta E (2001) New sesquiterpene derivatives from the red alga Laurencia scoparia. Isolation, structure determination, and anthelmintic activity. J. Nat. Prod. 64: 1552-1555.
42. De Clercq E (1996) Chemotheraphy of human immunodeficiency virus (HIV) infection: anti-HIV agents targeted at early stages in the virus replicative cycle. Biomed. Pharmacother. 50: 207-215.
43. De Clercq E (2000) Current lead natural products for the Chemotheraphy of human immunodeficiency virus (HIV) infection. Med. Res. Rev. 20: 323-349.
44. Della Pieta F, Bilia AR, Breschi MC, Cinelli F, Morelli I, Scatizzi R (1993) Crude extracts and two linear diterpenes from Cystoseira balearica and their activity. Planta Med. 59: 135-138.
45. Della Pieta F, Breschi MC, Scatizzi R, Cinelli F (1995) Relaxing activity of two linear diterpenes from Cystoseira brachycarpa var. balearica on the contractions of intestinal preparations. Planta Med. 61: 493-496.
46. Dumelod BD, Ramirez RP, Tiangson CL, Barrios EB, Panlasigui LN (1999) Carbohydrate availability of arroz caldo with λ-carrageenan. Int. J. Food Sci. Nutr. 50: 283-289.
47. el Refaey H, Templeton A (1995) Induction of abortion in the second trimester by a combination of misoprostol and mifepristone: a randomized comparison between two misoprostol regimen. Hum. Reprod. 10: 475-478.
48. el Sayed KA, Bartyzel P, Shen X, Perry TL, Zjawiony JK, Hamann MT (2000) Marine natural products as antituberculosis agents. Tetrahedron 56: 949-953.
49. Entzeroth M, Blackman AJ, Mynderse JS, Moore RE (1985) Structures and stereochemistries of oscillatoxin B, 31-noroscillatoxin B, oscillatoxin D, and 30-methyloscillatoxin D. J. Org. Chem. 50: 1255-1259.
50. Featonby-Smith BC, van Staden J (1984) Identification and seasonal variation of endogenous cytokinins in Ecklonia maxima (Osbeck) Papenf. Bot. Mar. 27:527-531.
51. Feldman SC, Reynaldi S, Stortz CA, Cerezo AS, Damont EB (1999) Antiviral properties of fucoidan fractions from Leathesia difformis. Phytomed. 6: 335-340.
52. Fischel JL, Lemée R, Formento P, Caldani C, Moll JL, Pesando D, Meinesz A, Grelier P, Pietra F, Gueniero A, Milano G (1995) Cell growth inhibitory effects of caulerpenyne, as esquiterpenoid from the marine alga Caulerpa taxifolia. Anticancer Res. 15: 2155-2160.
53. 2 in prostaglandin biosynthesis. Biochem. Pharmacol. 25: 285-291.
54. Francisco C, Banaigs B, Vails R, Codomier L (1985) Mediterraneol a, a novel rearranged diterpenoid-hydroquinone from the marine alga Cystoseira mediterranea. Tetrahedron Lett. 26: 2629-2632.
55. Fujiki H, Suganuma M (1996) Naturally-derived tumor promoters and inhibitors of carcinogenesis. J. Toxicol. 15: 129-156.
56. Fujiki H, Suganuma M, Yoshizawa S, Nishiwaki S, Winyar B, Sugimura T (1991) Mechanisms of action of okadaic acid class tumor promoters on mouse skin. Env. Health Persp. 93: 211-214.
57. Fukuyama Y, Kodama M, Miura I, Kinzyo Z, Kido M, Mori H, Nakayama Y, Takahashi M (1989) Structure of an anti-plasmin inhibitor, eckol, isolated from the brown alga Ecklonia kurome Okamura and inhibitory activities of its derivatives on plasma plasmin inhibitors. Chem. Pharm. Bull. 37: 349-353.
58. Fukuyama Y, Kodama M, Miura I, Kinzyo Z, Mori H, Nakayama Y, Takahashi M (1990) Anti-plasmin inhibitor. VI. Structure of phlorofucofuroeckol A, a novel phlorotannin with both dibenzo-1,4-dioxin and dibenzofuran elements, from Ecklonia kurome Okamura. Chem. Pharm. Bull. 38: 133-135.
59. 2: a candidate for causative agent of 'ogonori' poisoning. Bull. Jpn. Soc. Sci. Fish. 50: 463-469.
60. Galgani I, Pesando D, Porthe-Nibelle J, Fossat B, Girard JP (1996) Effect of caulerpenyne, a toxin extracted from Caulerpa taxifolia on mechanisms regulating intracellular pH in sea urchin eggs and sea bream hepatocytes. J. Giochem. Toxicol. 11: 243-250.
61. Gerwick WH, Bernart MW (1993) Eicosanoids and related compounds from marine algae. In Attaway DH, Zaborsky OR (eds), Marine Biotechnology, Vol.1, Pharmaceutical and Bioactive Natural Products, Plenum Press, NY, pp. 101-152.
62. Gerwick WH, Proteau PJ, Nagle DG, Wise ML, Jiang ZD, Bernart MW, Hamberg M (1993) Biologically active oxylipins from seaweeds. Hydrobiol. Ogia 260/261: 653-665.
63. Goetz G, Nakao Y, Scheur PJ (1997) Two acyclic kahalalides from the sacoglossan mollusk Elysia rufescens. J. Nat. Prod. 60: 562-567.
64. Graber DJ, Meier KH (1991) Acute misoprostol toxicity. Ann. Emerg. Med. 20: 549-551.
65. Graufel V, Kloareg B, Mabeau S, Durand P, Jozefonvicz J (1989) New natural polysaccharides with potent antithrombic activity: fucans from brown algae. Biomaterials 10: 363-368.
66. 2α in a plant - the red alga Gracilaria lichenoides. Tetrahedron Lett. 46: 4505-4506.
67. Griffin RL, Rogers DJ, Spencer-Phillips PT, Swain L (1995) Lectin from Codium fragile ssp. tomentosoides conjugated to colloidal gold: a new histochemical reagent. Br. J. Biomed. Sci. 52: 225-227.
68. Gurr MI, Harwood JL (1991) Lipid biochemistry, an introduction. 4th ed., Chapman and Hall, London, p.406.
69. Haefner B (2003) Drugs from the deep: marine natural products as drug candidates. Drug Discov. Today 8: 536-544.
70. Hamann MT, Scheuer PJ (1993) Kahalalide F: A bioactive depsipeptide from the sacoglossan mollusk, Elysia rufescens and the Green Alga Bryopsis sp. J. Am. Chem. Soc. 115: 5825-5826.
71. Hamann MT, Otto CS, Scheuer PJ, Dunbar DC (1996) Kahalalides: Bioactive peptides from a marine mollusk Elysia rufescens and its algal diet Biyopsis sp. J. Org. Chem. 61: 6594-6600.
72. Hennings H, Lowry DT, Robinson VA, Morgan DL, Fujiki H, Yuspa SH (1992) Activity of diverse tumor promoters in a keratinocyte co-culture model of initiated epidermis. Carcinogenesis 13: 2145-2151.
73. Higa T, Kuniyoshi M (2000) Toxins associated with medicinal and edible seaweeds. J. Toxicol. Tox. Rev. 19: 119-137.
74. Høiby N (2002) Understanding bacterial biofilms in patients with cystic fibrosis: current and innovative approaches to potential therapies. J. Cystic Fibrosis 1: 249-254.
75. Hopkins KJ, Wang G-J, Schmued LC (2000) Temporal progression of kainic acid induced neuronal and myelin degeneration in the rat forebrain. Brain Res. 864: 69-80.
76. Horgen FD, delos Santos DB, Goetz G, Sakamoto B, Kan Y, Nagai H, Scheuer PJ (2000) A new depsipeptide from the sacoglossan mollusk Elysia ornata and the green alga Bryopsis species. J. Nat. Prod. 63: 152-154.
77. Hori K, Miyazawa K, Fusetani N, Hashimoto K, Ito K (1986) Hypnins, low-molecular weight peptidic agglutinins isolated from a marine red alga, Hypnea japonica. Biochim. Biophys. Acta. 873: 228-236.
78. Imbs AB, Vologodskaya AV, Nevshupova NV, Khotimchenko SV, Titlyanov EA (2001) Response of prostaglandin content in the red alga Gracilaria verrucosa to season and solar irradiance. Phytochemistry 58: 1067-1072.
79. Impellizzeri G, Mangiafico S, Oriente G, Piatelli M, Sciuto S, Fattorusso E, Magno S, Santacroce C, Sica D (1975) Amino acids and low molecular weight carbohydrates of some marine red algae. Phytochemistry 14: 1549-1557.
80. Ireland CM, Copp BR, Foster MP, McDonald LA, Radisky DC, Swersey JC (1993) Biomedical potential of marine natural products. In Attaway DH, Zaborsky OR (eds), Marine Biotechnology, Vol. 1, Pharmaceutical and Bioactive Natural Products, Plenum Press, NY, pp. 1-43.
81. Ito E, Nagai H (1998) Morphological observations of diarrhea in mice caused by aplysiatoxin; the causative agent of the red alga Gracilaria coronopifolia poisoning in Hawaii. Toxicon 36: 1913-1920.
82. Ito E, Nagai H (2000) Bleeding from the small intestine caused by aplysiatoxin, the causative agent of the red alga Gracilaria coronopifolia poisoning. Toxicon 38: 123-132.
83. Ito K, Tsuchida Y (1972) The effect of algal polysaccharides on depressing of plasma cholesterol level in rats. Proc. Int. Seaweed Symp. 7: 451-155.
84. Jacobs RS, Bober MA, Pinto I, Williams AB, Jacobson PB, de Carvalho MS (1993) In Attaway DH, Zaborsky OR (eds), Marine Biotechnology, Vol. 1, Pharmaceutical and Bioactive Natural Products, Plenum Press, NY, pp. 77-99.
85. Jurd KM, Rogers DJ, Blunden G, McLellan DS (1995) Anticoagulant properties of sulphated polysaccharides and a proteoglycan from Codium fragile ssp. atlanticum. J. Appl. Phycol. 7: 339-345.
86. Kaeffer B, Benard C, Lahaye M, Blottiere HM, Cherbut C (1999) Biological properties of ulvan, a new source of green seaweed sulfated polysaccharides, on cultured normal and cancerous colonie epithelial cells. Planta Med. 65: 527-531.
87. Kakita H, Fukuoka S, Obika H, Li ZF, Kamishima H (1997) Purification and properties of a high molecular weight hemagglutinin from the red alga, Gracilaria verrucosa. Bot. mar. 40: 241-247.
88. Kakita H, Kitamura T (2003) Hemagglutinating activity in the cultivated red alga Gracilaria chorda Holmes, from Japan. In Chapman ARO, Anderson RJ, Vreeland VJ, Davison IR (eds), Proceedings of the 17th International Seaweed Symposium, Oxford University Press, Oxford, pp. 175-182.
89. Kan Y, Fujita T, Nagai H, Sakamoto B, Hokama Y (1998) Malyngamides M and N from the Hawaiian red alga Gracilaria coronopifolia. J. Nat. Prod. 61: 152-155.
90. Kato Y, Scheuer PJ (1974) Aplysiatoxin and debromoaplysiatoxin, constituents of the marine mollusk Stylocheilus longicauda (Quoy and Gaimard, 1824). J. Am. Chem. Soc. 96: 2245-2246.
91. Kawakubo A, Makino H, Ohnishi J-I, Hirohara H, Hori K (1997) The marine red alga Eucheuma serra J. Agardh, a high yielding source of two isolectins. J. Appl. Phycol. 9: 331-338.
92. Kazlauskas R, Mulder J, Murphy PT, Wells RJ (1980) New metabolites from the brown alga Caulacystis caphalornithos. Aust. J. Chem. 33: 2097-2101.
93. Kjelleberg S, Steinberg P (2001) Surface warfare in the sea. Microbiology Today 28: 134-135.
94. Kelecom A (2002) Secondary metabolites from marine microorganisms. An. Acad. Bras. Cienc. 74: 151-170.
95. Kiriyama S, Okazaki Y, Yoshida A (1968) Hypocholesterolemic effect of polysaccharides and polysaccharide foodstuffs in cholesterol fed rats. J. Nutr. 97: 382-388.
96. Kolender AA, Matulewicz MC, Cerezo AS (1995) Structural analysis of antiviral sulfated α-D-(13)-linked mannans. Carbohyd. Res. 273: 179-185.
97. Kris-Etherton PM, Hecker KD, Bonanome A, Coval SM, Binkoski AE, Hilpert KF, Griel AE, Etherton TD (2002) Bioactive compounds in foods: their role in the prevention of cardiovascular disease and cancer. Am. J. Med. 113: 71S-88S.
98. Kuznetsova TA, Krylova NV, Besednova NN, Vasil'eva VN, Zviagintseva TN, Krashevskii SV, Eliakova LA (1994) The effect of translam on the natural resistance indices of the irradiated organism. Radiats Biol Radioecol. 34: 236-239.
99. Lamela M, Anca J, Villar R, Otero J, Calleja JM (1989) Hypoglycemic activity of several seaweed extracts. J. Ethnopharmacol. 27: 35-43.
100. Laycock MV, de Freitas ASW, Wright JLC (1989) Glutamate agonists from marine algae. J. Appl. Phycol. 1: 113-122.
101. 2α instillation for termination in second-trimester pregnancy. J. Matern-Fetal Invest. 8:134-138.
102. Levine L (1998) Proteolysis negatively regulates agonist-stimulated arachidonic acid metabolism. Cell. Signal. 10: 653-659.
103. Lima HC, Costa FHF, Sampaio AH, Neves SA, Benevides NMB, Teixeira DIA, Rogers DJ, Freitas ALP (1998) Induction and inhibition of human lymphocyte transformation by the lectin from the red marine alga Amansia multifida. J. Appl. Phycol. 10: 153-162.
104. Lincoln RA, Strupinski K, Walker JM (1991) Bioactive compounds from algae. Life Chem. Rep. 8: 97-183.
105. Llovo J, Lopez A, Fabregas J, Munoz A (1993) Interaction of lectins with Cryptosporidium parvum. J. Infect. Dis. 167: 1477-1480.
106. Maeda M, Kodama T, Saito M, Tanaka T, Yoshizumi H, Nomoto K, Fujita T (1987) Neuromuscular action of insecticidal domoic acid on the American cockroach. Pest. Biochem. Biophysiol. 28: 85-92.
107. Maeda M, Kodama T, Tanaka T, Ohfune Y, Nomoto K, Nishimura K, Fujita T (1984) Insecticidal and neuromuscular activities of domoic acid and its related compounds. J. Pest. Sci. 9: 27-32.
108. Maeda M, Kodama T, Tanaka T, Yoshizumi H, Takemoto T, Nomoto K, Fujita T (1986) Structures of isodomoic acids A, B and C, novel insecticidal amino acids from the red alga Chondria armata. Chem. Pharmaceut. Bull. 34: 4892-4895.
109. Majczak GAH, Richartz RRTB, Duarte MER, Noseda MD (2003) Antiherpetic activity of heterofucans isolated from Sargassum stenophyllum (Fucales, Phaeophyta). In Chapman ARO, Anderson RJ, Vreeland VJ, Davison IR (eds), Proceedings of the 17th International Seaweed Symposium, Oxford University Press, Oxford, pp. 169-174.
110. Malhotra R, Ward M, Bright H, Priest R, Foster MR, Hurle M, Blair E, Bird M (2003) Isolation and characterisation of potential respiratory syncytial virus receptor(s) on epithelial cells. Microbes Infect. 5: 123-133.
111. Manefield M, Harris L, Rice SA, De Nys R, Kjelleberg S (2000) Inhibition of luminescence and virulence in the black tiger prawn (Penaeus monodon) pathogen Vibrio harveyi by intercellular signal antagonists. Appl. Environ. Microbiol. 66: 2079-2084.
112. Manefield M, Welch M, Givskov M, Salmond GPC, Kjelleberg S (2001) Halogenated furanones from the red alga, Delisea pulchra, inhibit carbapenem antibiotic synthesis and exoenzyme virulence factor production in the phytopathogen Erwinia carotovora. FEMS Microbiol. Lett. 205: 131-138.
113. Maruyama H, Nakajima J, Yamamoto I (1987) A study on the anticoagulant and fibrinolytic activities of a crude fucoidan from the edible brown seaweed Laminaria religiosa, with special reference to its inhibitory effect on the growth of sarcoma-180 ascites cells subcutaneously implanted into mice. Kitasato Arch. Exp. Med. 60: 105-121.
114. Matou S, Helley D, Chabut D, Bros A, Fischer A-M (2002) Effect of fucoidan on fibroblast growth factor-2-induced angiogenesis in vitro. Thromb. Res. 106: 213-221.
115. Matsubara K, Matsuura Y, Hori K, Miyazawa K (2000) An anticoagulant proteoglycan from the marine green alga, Codium pugniformis. J. Appl. Phycol. 12: 9-14.
116. Mayer AMS, Lehmann VKB (2000) Marine pharmacology in 1998: Marine compounds with antibacterial, anticoagulant, antifungal, antiinflammatory, 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.
117. Mayer AMS, Paul VJ, Fenical W, Norris JM, de Carvalho MS, Jacobs RS (1993) Phospholipase A2 inhibitors from marine algae. Hydrobiologia 260/261: 521-529.
118. Mazumder S, Ghosal PK, Pujol CA, Carlucci MJ, Damonte EB, Ray B (2002) Isolation, chemical investigation and antiviral activity of polysaccharides from Gracilaria corticata (Gracilariaceae, Rhodophyta). Int. J. biol. Macromol. 31: 87-95.
119. Moore RE (1982) Toxins, anticancer agents, and tumor promoters from marine prokaryotes. Pure and Appl. Chem. 54: 1919-1934.
120. Mullin JM, McGinn MT, Snock KV, Imaizumi S (1990) The effects of teleocidin and aplysiatoxin tumor promoters on epithelial tight junctions and transepithelial permeability: comparison to phorbol esters. Carcinogen. 11: 377-385.
121. Mynderse JS, Moore RE (1978) Toxins from blue-green algae: Structures of oscillatoxin A and three related bromine-containing toxins. J. Org. Chem. 43: 2301-2303.
122. Nagai H, Yasumoto T, Hokama Y (1996) Aplysiatoxin and debromoaplysiatoxin as the causative agents of a red alga Gracilaria coronopifolia poisoning in Hawaii. Toxicon 34: 753-761.
123. Nagai H, Yasumoto T, Hokama Y (1997) Manauealides, some of the causative agents of a red alga Gracilaria coronopifolia poisoning in Hawaii. J. Nat. Prod. 60: 925-928.
124. Nakamura H, Moriya M (1999) Purification and partial characterization of a lectin-like protein from the sea algae Laminaria diabolica that induces fertilization envelope formation in sea urchin eggs. Zool. Sci. 16: 247-253.
125. Nakashima H, Kido Y Kobayashi N, Motoki Y Neushul M, Yamamoto N (1987a) Antiretroviral activity in a marine red alga; reverse transcriptase inhibition by an aqueous extract of Schizymenia pacifica. J. Cancer Res. Clin. Onc. 113: 413-416.
126. Nakashima H, Kido Y Kobayashi N, Motoki Y, Neushul M, Yamamoto N (1987b) Purification and characterization of an avian myeloblastosis and human immunodeficiency virus reverse transcriptase inhibitor, sulfated polysaccharides extracted from sea algae. Antimicrob. Agents Chemotheraphy 31: 1524-1528.
127. Neves SA, Dias-Baruff M, Freitas AL, Roque-Barreira MC (2001) Neutrophil migration induced in vivo and in vitro by marine algal lectins. Inflam. Res. 50: 486-490.
128. Ng TB, Li WW, Yeung HW (1989) Effects of lectins with various carbohydrate binding specificities on lipid metabolism in isolated rat and hamster adipocytes. Int. J. Biochem. 21: 149-155.
129. Nishide E, Anzai H, Uchida H (1993) Effects of alginates on the ingestion and excretion of cholesterol in the rat. J. Appl. Phycol. 5: 207-211.
130. Nishide E, Uchida H (2003) Effects of Ulva powder on the ingestion and excretion of cholesterol in rats. In Chapman ARO, Anderson RJ, Vreeland VJ, Davison IR (eds), Proceedings of the 17th International Seaweed Symposium, Oxford University Press, Oxford, pp. 165-168.
131. Nishino T, Nagumo T (1991) The sulfate-content dependence of the anticoagulant activity of a fucan sulfate from the brown seaweed Ecklonia kurome. Carbohyd. Res. 214: 193-197.
132. Nishino T, Nagumo T (1992) Anticoagulant and antithrombin activities of oversulfated fucans. Carbohyd. Res. 229: 355-362.
133. Noa M, Mas R, Carbajal D, Valdés S (2000) Effect of D-002 on acetic acid-induced colitis in rats at single and repeated doses. Pharmacol. Res. 41: 391-395.
134. Noguchi T, Matsui T, Miyazawa K, Asakawa M, Iijima N, Shida, Fuse M, Hosaka Y, Kirigaya C, Watabe K, Usui S, Kukagawa A (1994) Poisoning by the red alga 'ogonori' (Gracilaria verrucosa) on the Nojima Coast, Yokohama, Kanagawa Prefecture, Japan. Toxicon 32: 1533-1538.
135. Nomura K, Nakamura H, Suzuki N (2000) False fertilization in sea urchin eggs induced by diabolin, a 120K kelp protein. Biochem. Biophys. Res. Comm. 273: 691-693.
136. Nuijen B, Bouma M, Talsma H, Manada C, Jimeno JM, Lopez-Lazaro L, Bult A, Beijnen JH (2000) Development of a lyophilized parenteral pharmaceutical formulation of the investigational polypeptide marine anticancer agent kahalalide F. Drug Dev. Ind. Pharm. 27: 767-780.
137. Oehninger S, Clark GF, Acosta AA, Hodgen GD (1991) Nature of the inhibitory effect of complex saccharide moieties on the tight binding of human spermatozoa to the human zona pellucida. Fertil. Steril. 55: 165-169.
138. Ohta T, Sasaki S, Oohori T, Yoshikawa S, Kurihara H (2002) β-Glucosidase inhibitory activity of a 70% methanol extract from ezoishige (Pelvetia babingtonii de Toni) and its effect on the elevation of blood glucose level in rats. Biosci. Biotechnol. Biochem. 66: 1552-1554.
139. Okamura H, Kuroda S, Ikegami S, Tomita K, Sugimoto Y, Sakaguchi S, Ito Y, Katsuki T, Yamaguchi M (1993) A formal synthesis of aplysiatoxin: enantioselective synthesis of Kishi's aldehyde. Tetrahedron 49: 10531-10554.
140. Okamura H, Kuroda S, Tomita K, Ikegami S, Sugimoto Y, Sakaguchi S, Katsuki T, Yamaguchi M (1991) Synthesis of aplysiatoxin: stereoselective synthesis of key fragments. Tetrahedrom Lett. 32: 5137-5140.
141. Osborne NJT, Webb PM, Shaw GR (2001) The toxins of Lyngbya majuscula and their human and ecological health effects. Env. Int. 27: 381-392.
142. Panlasigui LN, Baello OQ, Dimatangal JM, Dumelod BD (2003) Blood cholesterol and lipid-lowering effects of carrageenan on human volunteers. Asia-Pac. J. Clin. Nutr. 12: 209-214.
143. Palermo JA, Flower BP, Seldes AM (1992) Chondriamides A and B, new indolic metabolites from the red alga Chondria sp. Tetrahedron Lett. 33: 3097-3100.
144. Parent-Massin D, Fournier V, Amade P, Lemee R, Durand-Clement M, Delescluse C, Pesando D (1996) Evaluation of the lexicological risk to humans of caulerpenyne using human hematopoietic progenitors, melanocytes, and keratinocytes in culture. J. Toxicol. Env. Health 47: 47-59.
145. Patankar MS, Oehninger S, Barnett T, Williams RL, Clark GF (1993) A revised structure for fucoidan may explain some of its biological activities. J. Biol. Chem. 268: 21770-21776.
146. Patchett RA, Kelly AF, Kroll RG (1991) The adsorption of bacteria to immobilized lectins. J. Appl. Bacteriol. 71: 277-284.
147. Patier P, Yvin J, Kloareg B, Liénart Y, Rochas C (1993) Seaweed liquid fertilizer from Ascophyllum nodosum contains elicitors of plant D-glycanases. J. Appl. Phycol. 5: 343-349.
148. Pedrotti ML, Lemee R (1996) Effect of microalgae treated with natural toxins on the nutrition and development of filter-feeding sea-urchin larvae. Mar. Env. Res. 48: 177-192.
149. Pesando D, Huitorel P, Dolcini V, Amade P, Girard JP (1998) Caulerpenyne interferes with microtubule-dependent events during the first mitotic cycle of sea urchin eggs. Eur. J. Cell Biol. 77: 19-26.
150. Pesando D, Lemée R, Ferrua C, Amade P, Girard J-P (1996) Effects of caulerpenyne, the major toxin from Caulerpa taxifolia on mechanisms related to sea urchin egg cleavage. Aquat. Toxicol. 35: 139-155.
151. Ponce NMA, Pujol CA, Damonte EB, Flores ML, Stortz CA (2003) Fucoidans from the brown seaweed Adenocystis utricularis: extraction methods, antiviral activity and structural studies. Carbohyd. Res. 338: 153-165.
152. Premakumara GAS, Ratnasooriya WD, Tillekeratne LMV (1995) Studies on the post-coital contraceptive mechanisms of crude extract of Sri Lankan marine red alga, Gelidiella acerosa. Contraception 52: 203-207.
153. Premakumara GAS, Ratnasooriya WD, Tillekeratne LMV (1996) Isolation of a non-steroidal contragestative agent from Sri Lankan marine red alga, Gelidiella acerosa. Contraception 54: 379-383.
154. Ramsey UR Bird CJ, Shacklock PF, Laycock MV, Wright JL (1994) Kainic acid and 1′-hydroxykainic acid from Palmariales. Nat. Toxins 2: 286-292.
155. Rasmussen TB, Manefield M, Andersen JB, Eberl L, Anthoni U, Christophersen C, Steinberg P, Kjelleberg S, Givskov M (2000) How Delisea pulchra furanones affect quorum sensing and swarming motility in Serratia liquefaciens MG1. Microbiology 146: 3237-3244.
156. Religa P, Kazi M, Thyberg J, Gaciong Z, Swedenborg J, Hedin U (2000) Fucoidan inhibits smooth muscle cell proliferation and reduces mitogen-activated protein kinase activity. Eur. J. Vasc. Endovasc. Surg. 20: 419-426.
157. Renn DW (1997) Biotechnology and the red seaweed polysaccharide industry: status, needs and prospects. Tibtech 15: 9-14.
158. Renn DW, Noda H, Amano H, Nishino T, Nishizana K (1994a) Antihypertensive and antihyperlipidemic effects of funoran. Fisheries Sci. 60: 423-427.
159. Renn DW, Noda H, Amano H, Nishino T, Nishizana K (1994b) Study on hypertensive and antihyperlipidemic effect of marine algae. Fisheries Sci. 60: 83-88.
160. Rogers DJ, Hori K (1993) Marine algal lectins: New developments. Hydrobiologia 260/261: 589-261.
161. Saito K, Nishijima M, Ohno N (1992) Structure and antitumor activity of the less-branched derivatives of an alkali-soluble glucan isolated from Omphalia lapidescens. Chem. Pharmaceut. Bull. 40: 261-263.
162. 2 in the red algae, Gracilaria asiatica and G. rhodocaudata. Fisheries Sci. 63: 128-131.
163. Sajiki J, Kakimi H (1998) Identification of eicosanoids in the red alga, Gracilaria asiatica, using high-performance liquid chromatography and electrospray ionization mass spectrometry. J. Chromatogr. 795: 227-237.
164. Sato M, Nakano T, Takeuchi M, Kanno N, Nagahisa E, Sato Y (1996) Distribution of neuroexitatory amino acids in marine algae. Phytochemistry 42: 1595-1597.
165. Schaeffer DJ, Krylov VS (2000) Anti-HIV activity of extracts and compounds from algae and cyanobacteria. Ecotox. Env. Safe. 45: 208-227.
166. Scheuer PJ, Haman MT, Gravalos DG (2000) Cytotoxic and antiviral compound. US Patent Number 601 1010.
167. Serdula M, Bartolini G, Moore RE, Gooch J, Wiebenga N (1982) Seaweed itch on windward Oahu, Hawaii. Med. J. 41: 200-201.
168. Shanmugam M, Mody KH, Ramavat BK, Murthy ASK, Siddhanta AK (2002) Screening of Codiacean algae (Chlorophyta) of the Indian coasts for blood anticoagulant activity. Indian Ind. J. mar. Sci. 31: 33-38.
169. Sharma GM, Sahni MK (1993) Marine proteins and clinical chemistry. In Attaway DH, Zaborsky OR (eds), Marine Biotechnology, Vol. 1. Pharmaceutical and Bioactive Natural Products. Plenum Press, NY, pp. 153-180.
170. Shibata H, Kimura-Takagi I, Nagaoka M, Hashimoto S, Aiyama R, Iha M,
171. Smith DS, Kitts DD (1994) A competitive enzyme-linked immunoassay for domoic acid determination in human body fluids. Food Chem. Toxicol. 32: 1147-1154.
172. Sparidans RW, Stokvis E, Jimeno JM, Lopez-Lazaro L, Schellens JH, Beijnen JH (2001) Chemical and enzymatic stability of a cyclic depsipeptide, the novel, marine-derived, anti-cancer agent kahalalide F. Anticancer Drugs 12: 575-582.
173. Spieler R (2002) Seaweed compound's anti-HIV efficacy will be tested in southern Africa. Lancet 359: 1675.
174. Stefanov K, Konaklieva M, Brechany EY, Christie WW (1988) Fatty acid composition of some algae from the Black Sea. Phytochemistry 27: 3495-3497.
175. Stokvis E, Rosing H, López-Lázaro L, Rodriguez I, Jimeno JM, Supko JG, Schellens JHM, Beijnen JH (2002) Quantitative analysis of the novel depsipeptide anticancer drug Kahalalide F in human plasma by high-performance liquid chromatography under basic conditions coupled to electrospray ionization tandem mass spectrometry. J. mass Spectrom. 37: 992-1000.
176. Sugawara I, Itoh W, Kimura S, Mori S, Shimada K (1989) Further characterization of sulfated homopolysaccharides as anti-HIV agents. Experientia 45: 996-998.
177. Takemoto T, Daigo K (1958) Constituents of Chondria armata and their pharmacological effects. Chem. Pharmaceut. Bull. 6: 578-580.
178. Takikawa M, Uno K, Ooi T, Kusumi T, Akera S, Muramatsu M, Mega H, Horita C (1998) Crenulacetal C, a marine diterpene, and its synthetic mimics inhibiting Polydora websterii, a harmful lugworm damaging pearl cultivation. Chem. Pharmaceut. Bull. 46: 462-466.
179. Tanabe H, Kamishima H, Kobayashi Y (1993) Inhibitory effect of red alga lectin and skipjack fat on the growth of the red tide plankton Chattonella antiqua. J. Ferment. Bioeng. 75: 387-388.
180. Tobacman JK (2001) review of harmful gastrointestinal effects of carrageenan in animal experiments. Env. Health Perspect. 109: 983-994.
181. Trento F, Cattaneo F, Pescador R, Porta R, Ferro R (2001) Antithrombin activity of an algal polysaccharide. Thromb. Res. 102: 457-465.
182. Ueyama H, Sasaki I, Shimomura K, Suganuma M (1995) Specific protein interacting with a tumor promoter, debromoaplysiatoxin, in bovine serum is α-1-acid glycoprotein. J. Cancer Res. Clin. Onc. 121: 211-218.
183. Urones JG, Basabe P, Marcos IS, Pineda J, Lithgow AM, Moro RF, Brito Palma FMS, Araujo MEM, Gravalos MDG (1992) Meroterpenes from Cystoseira usneoides. Phytochemistry 31: 179-182.
184. Valls R, Piovetti L, Banaigs B, Archavlis A, Pellegrini M (1995) (S)-13-hydroxygeranylgeraniol-derived furanoditerpenes from Bifurcaria bifurcata. Phytochemistry 39: 145-149.
185. Wakamiya T, Nakamoto H, Shibata T (1984) Structural determination of Carnosadine, a new cyclopropyl amino acid, from the alga Grateloupia carnosa. Tetrahedron Lett. 25: 4411-4412.
186. Wallace JL (1999) Distribution and expression of cyclooxygenase (COX) isoenzymes, their physiological roles, and the categorization of nonsteroidal anti-inflammatory drugs (NSAIDs). Am. J. Med. 107: 11S-17S.
187. Watanabe K, Miyakado M, Ohno N, Okada A, Yanagi K, Moriguchi K (1989) A polyhalogenated insecticidal monoterpene from the red alga, Plocamium telfairiae. Phytochemistry 28: 77-78.
188. Watanabe K, Umeda K, Kurita Y, Takayama C, Miyakado M (1990) Two insecticidal monoterpenes, telfairine and aplysiaterpenoid A, from the red alga Plocamium telfairiae: structure elucidation, biological activity, and molecular topographical consideration by a semiempirical molecular orbital study. Pest. Biochem. Physiol. 37: 275-286.
189. White JD, Blakemore PR, Browder CC, Hong EJ, Robarge LA (2001) Total synthesis of the marine toxin polycavernoside A via selective macrolactonization of a trihydroxy carboxylic acid. J. Am. Chem. Soc. 123: 8593-8595.
190. Witvrouw M, Este JA, Mateu MQ, Reymen D, Andrei G, Snoeck R, Ikeda S, Pauwels R, Bianchini NV, Desmyter J, de Clercq E (1994) Activity of a sulfated polysaccharide extracted from the red seaweed Aghardhiella tenera against human immunodeficiency virus and other enveloped viruses. Antiviral Chem. Chemotheraphy 5: 297-303.
191. Wu AM, Wu JH, Watkins WM, Chen CP, Song SC, Chen YY (1998) Differential binding of human blood group Sd(a+) and Sd(a-) Tamm-Horsfall glycoproteins with Dolichos biflorus and Vicia villosa-B4 agglutinins. FEBS Lett. 429: 323-326.
192. Wu AM, Wu JH, Watkins WM, Chen CP, Tsai MC (1996) Binding properties of a blood group Le(a+) active sialoglycoprotein, purified from human ovarian cyst, with applied lectins. Biochim. Biophys. Acta - Mol. Basis Dis. 1316: 139-144.
193. Yoshizawa Y, Ametani A, Tsunehiro J, Nomura K, Itoh M, Fukui F, Kaminogawa S (1995) Macrophage stimulation activity of the polysaccharide fraction from a marine alga (Porphyra yezoensis): structure-function relationships and improved solubility. Biosci. Biotech. Biochem. 59: 1933-1937.
194. Yotsu-Yamashita M, Haddock RL, Yasumoto T (1993) Polycavernoside A: a novel glycosidic macrolide from the red alga Polycavernosa tsudai (Gracilaria edulis). J. Am. Chem. Soc. 115: 1147-1148.
195. Yotsu-Yamashita M, Seki T, Paul VJ, Naoki H, Yasumoto T (1995) Four new analogs for polycavernoside A. Tetrahedron Lett. 36: 5563-5566.
196. Zaman L, Arakawa O, Shimosu A, Onoue Y Nishio S, Shida Y, Noguchi T (1997) Two new isomers of domoic acid from a red alga, Chondria armata. Toxicon 35: 205-212.
197. Zaporozhets TA, Zvyagintseva TN, Besednova NN, Elyakova LA (1995) Influence of translam for the immune response irradiated mice. Radiobiol. 35: 260-263.
198. Zeitlin L, Whaley KJ, Hegarty TA, Moench TR, Cone RA (1997) Tests of vaginal microbicides in the mouse genital herpes model. Contraception 56: 329-335.
199. Zhu W, Ooi VEC, Chan PKS, Ang Jr PO (2003) Inhibitory effect of extracts of marine algae from Hong Kong against Herpes simplex viruses. In Chapman ARO, Anderson RJ, Vreeland VJ, Davison IR (eds), Proceedings of the 17th International Seaweed Symposium, Oxford University Press, Oxford, pp. 159-164.