Bioactive compounds from cyanobacteria and microalgae: An overview

Critical Reviews in Biotechnology

Volumn 25, Issue 3, 2005, Pages 73-95

  Singh, Sawraj ^a   Kate, Bhushan N ^a   Banecjee, U C ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Bioactive compounds; Colorants; Cyanobacteria; Microalgae; Pigments; Toxins

Indexed keywords

ALGAE; DATA REDUCTION; FOOD PRODUCTS; GENETIC ENGINEERING; MICROORGANISMS; PIGMENTS; PROTEINS; TOXIC MATERIALS; VITAMINS;

BIOACTIVE COMPOUNDS; COLORANTS; CYANOBACTERIA; MICROALGAE; TOXINS;

BACTERIA;

8 HYDROXYMANZAMINE A; ANATOXIN A; ANTILLATOXIN; BACTERIAL TOXIN; BARBAMIDE; BETA CAROTENE; BOROPHYCIN; BREVITOXIN; CALCIUM SPIRULAN; CHEMICAL AGENT; COLORING AGENT; CRYPTOPHYCIN 296; CRYPTOPHYCIN 309; CYANOVIRIN N; FUEL; HOMOANATOXIN A; KALKITOXIN; LIPOPEPTIDE; LITOSTEROL; LYCOPENE; MANZAMINE A; NATURAL PRODUCT; NEUROTOXIN; PIGMENT; PROTEIN; SAXITOXIN; SCYPTOLIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; VITAMIN; XANTHOPHYLL;

ALGA; ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; BIOSYNTHESIS; BLUE GREEN ALGA; CYANOBACTERIUM; DRUG MECHANISM; GENETIC ENGINEERING; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; NONHUMAN; PHOTOSYNTHESIS; PRIORITY JOURNAL; PROKARYOTE; QUALITY CONTROL; REVIEW; STRUCTURE ACTIVITY RELATION;

ALGAE; BIOLOGICAL FACTORS; BIOLOGICAL PRODUCTS; BIOTECHNOLOGY; CYANOBACTERIA;

CHLOROPHYTA; CYANOBACTERIA; PROKARYOTA;

EID: 26444539868     PISSN: 07388551     EISSN: None     Source Type: Journal    
DOI: 10.1080/07388550500248498     Document Type: Review

References (89)

1. Abrahamsson, K., Ekdahl, A., Collén, J., and Pedersén, M. 1995. Marine algae-a source of trichloroethylene and perchloroethylene. Limnology and Oceanography. 40: 1321-1326.
2. Antonopoulou, S., Nomikos, T., Oikonomou, A., Kyriacou, A., Andriotis, M., Fragopoulou, E., and Pantazidou, A. 2005. Characterization of bioactive glycolipids from Scytonema julianum. Cyanobacteria. Compar. Biochem. and Physiol part B. 140: 219-231.
3. Arment, A. R., and Carmichael, W. W. 1996. Evidence that microcystin is a thio-template product. J. Phycol. 32: 591-597.
4. Atchison, W. D., Luke, V. S., Narahashi, T., and Vogel, S. M. 1986. Nerve membrane sodium channels as the target site of brevetoxins at neuromuscular junctions. Br. J. Pharmacol. 189: 731-738.
5. Ayehunie, S., Belay, A., Baba, T. W., and Ruprecht, R. M. 1998. Inhibition of HIV-1 replication by an aqueous extract of Spirulina platensis. J. Aquir. Immun. Defic Syndr. Hum. Retrovirol. 18: 7-12.
6. Baden, D. G. 1989. Marine food-borne dinoflagellate toxins. Internat Rev Cytology. 82: 99-150.
7. Baden, D. G., 1983. Brevitoxin: unique polyether dinoflagellate toxins; The FASEB Journal. 3: 1807-1817.
8. Belarbi, E. H., Molina, E., and Chisti, Y. 2000 A process for high yield and scaleable recovery of high purity eicosapentaenoic acid ester from microalgae and fish oil. Enz Microb Technol. 26: 516-529.
9. Ben-Amotz, A., and Avron, M. 1990. The biotechnology of cultivating the halotolarant alga Dunaliella. TIBTECH. 8: 121.
10. Berman, J. 1998. Chemotherapy of leishmaniasis: recent advances in the treatment of visceral disease. Curr. Opin. Infect. Dis. 11: 707-710.
11. Bhat, V. B., and Madyastha, K. M. 2000. C-phycocyanin: a potent peroxyl radical scavenger in vivo and in vitro. Biochem. Biophys. Res. Commun. 275: 20-25.
12. Borowitzka, M. A., and Borowitzka, L. J., 1987. Vitamins and fine chemicals from micro-algae. Micro. Algal. Biotechnol. M. A. Borowitzka and L. J Borowitzka, eds. New York. Cambridge University Press. 153-196.
13. Boyd, M. R. 2001. Anti-cyanovirin antibody with an internal image of gp120, a method of use thereof, and a method of using a cyanovirin to induce an immune response to gp120. United States patent no 6193982.
14. Boyd, M. R. 2002. Methods of using cyanovirins topically to inhibit viral infection. United States patent no 6420336.
15. Boyd, M. R. 2004. Methods of using cyanovirins to inhibit viral infection. United States patent no 6743577.
16. Burja, A. M., Abou-Mansour, Banaigs, E. B., Payri, C., Burgess, J. G., and Wright, P. C. 2002. Culture of marine cyanobacterium, Lyngbya majuscula (Oscillatoriaceae), for bioprocess intensified production of cyclic and linear lipopeptides. J. Microbiol. Meth. 48: 207-219.
17. Burja, A. M., Banaigs, E. B., Abou-Mansour, Burgess, J. G., and Wright, P. C. 2001. Marine cyanobacteria-a prolific source of natural products. Tetrahedron, 57: 9347-9377.
18. Carmichael, W. W., Beasley, V., Bunner, D. L., Eloff, J. N., Falconer, I., Gorham, P., Harada, K.-I., Krishnamurthy, T., Yu, M.-J., Moore, R. E., Rinehart, K., Runnegar, M., Skulberg, O. M., and Watanabe, M. 1988. Naming of cyclic heptapeptide toxins of cyanobacteria (blue-green algae). Toxicon. 26: 971-973.
19. Carmichael, W. W., Biggs, D. F., and Gorham, P. R. 1977. Toxicology and pharmacological action of Anabaena flos-aquae toxin. Science. 187:542-544.
20. Colleluori, D. M., Tien, D., Kang, F., Pagliei, T., Ryan Kuss, R., McCormick, T., Watson, K., McFadden, K., Chaiken, I., Buckheit, Jr, R. W., and Romano, J. W. 2005. Expression, purification, and characterization of recombinant cyanovirin-N for vaginal anti-HIV microbicide development. Protein Expr. Purif. 39: 229-236
21. Chang, Z., Flatt, P., Gerwick W. H., Nguyen, V.-H., Wills, C. L., Sherman, D. H. 2002. The barbamide biosynthetic gene cluster: a novel marine cyanobacterial system of mixed polyketide synthase (PKS)-non ribosomal peptide synthetases (NRPS) origin involving an unusual trichloroleucyl starter unit. Gene. 296: 235-247.
22. Chen, and F., Zhang, Y. 1997. High cell density mixotrophic culture of Spirulina platensis on glucose for phycocyanin production using a fed-batch system. Enz. Microb. Technol. 20: 221-224.
23. Deng, M. D., and Coleman, J. R. 1999. Ethanol synthesis by genetic engineering in Cyanobacteria. Appl. Env. Microbiol. 65: 523-528.
24. Devlin, J. P., Edwards, O. E., Gorham, P. R., Hunter, N. R., Pike, R. K., and Starvick, B. 1977. Anatoxin-a, a toxic alkaloid from Anabaena flos-aquae NCR-44h. Can. J. Chem. 5: 1367-1371.
25. Donia, M., and Hamann, M. T. 2003. Marine natural products and their potential application as anti-infective agents. The Lancet. 3: 338-348.
26. Gerwick, W. H., Jianga, Z. D., Agarwala, S. K., and Farmer, B. T. 1992. Total structure of hormothamnin A, A toxic cyclic undecapeptide from the tropical marine cyanobacterium hormothamnion enteromorphoides. Tetrahedron. 48: 2313-2324.
27. Gorham, P. J., McLachlan, J., Hammer, U. T., and Kim, W. K. 1964. Isolation and toxic strains of Anabaena flos-aquae. de Breb. Verh. Internat. Verein. Limnol. 15: 796-804.
28. Grach-Pogrebinsky, O., Sedmak, B., and Carmeli, S. 2003. Protease inhibitors from a Slovenian Lake Bled toxic water bloom of the cyanobacerium Planktothrix rubescens. Tetrahedron. 59: 8329-8336.
29. Grima, E. M., Belarbi, E. H., Fernandez, F. G. A., Medina, A. R., and Chisti, Y. 2003. Recovery of microalgal biomass and metabolites: process options and economics. Biotech. Adv. 20: 491-515.
30. Gustafson, K., Cardellina, J., Fullar, R. W., Weislow, O. S., Kiser, R. F., Snader, K. M., Patterson, G. M. L., and Boyd, R. M. 1989. AIDS-antiviral sulfolipids from cyanobacteria (blue-green algae). J. National. Cancer. Institute. 81: 1254-1258.
31. Hayashi, O., Hirahashi, T., Katoh, T., Miyajima, H., Hirano, T., and Okuwaki, Y. 1998. Class-specific influence of dietary Spirulina platensis on antibody production in mice. J. Nutr. Sci. Vitaminol. (Tokyo). 44: 841-851.
32. Hayashi, T., and Hayashi, K. 1996. Calcium spirulan, an inhibitor of enveloped virus replication from a Blue-Green Alga Spirulina platensis. J. Nat Prod. 59: 83-87.
33. Hayashi, K., Hayashi, T., and Kojima, I. 1996. A natural sulfated polysaccharide, calcium spirulan, isolated from Spirulina platensis: in vitro and ex vivo evaluation of anti-herpes simplex virus and anti-human immunodeficiency virus activities. AIDS. Res. Hum. Retrovir. 12: 1463-1471.
34. Hayashi, O., Katoh, T., and Okuwaki, Y. 1994. Enhancement of antibody production in mice by dietary Spirulina platensis. J. Nutr. Sci. Vitaminol. (Tokyo) 40: 431-441.
35. Honkanen, R. E., Zwiller, J., Moore, R. E., Daily, S. L., Khatra, B. S., Dukelow, M., and Boynton, A. L. 1990. Chracterization of microcystin-LR, a potent inhibitor of type 1 and type 2A protein phospatases. J. Biol. Chem. 65: 19401-19404.
36. Iwata, K., Inayama, T., and Kato, T. 1990. Effects of Spirulina platensis on plasma lipoprotein lipase activity in fructose-induced hyperlipidemic rats. J. Nutr. Sci. Vitaminol. (Tokyo) 36: 165-171.
37. Jensen, G. S., Ginsberg, D. I., Huerta, P., Citton, M., and Drapeau, C. 2000. Consumption of Aphanizomenon flos aquae has rapid effects on the circulation and function of immune cells in humans. A novel approach to nutritional mobilization of the immune system. JANA. 2: 50-58.
38. Kashihara, N., Toe, S., Nakamura, K., Umezawa, K., Yamamura, S., and Nishiyama, S. 2000. Synthesis and biological activities of hapalosin derivatives with modification at C12 position. Bioorg. Med. Chem. Lett. 10: 101-103.
39. Kerfeld, C. A. 2004. Water soluble carotenoid proteins of cyanobacteria. Archiv. Biochem. Biophys. 430: 2-9.
40. Kim, H. M., Lee, E. H., Cho, H. H., and Moon, Y. H. 1998. Inhibitory effect of mast cell-mediated immediate-type allergic reactions in rats by spirulina. Biochem. Pharmacol. 55: 1071-1076.
41. Koehn, F. E., Longley, R. E., and Reed, J. K. 1992. Microcolins A & B, new immunosuppressive peptidesfrom the blue green alga Lyngbya majuscula. J. Nat. Prod. 55: 613-619.
42. Kushak, R. I., Drapeau, C., Van Cott, E. M., and Winter, H. H. 2000. Favorable effects of blue-green algae Aphanizomenon flos-aquae on rat plasma lipids. JANA. 2: 59-65.
43. Kushak, R. I., VanCott, E., Drapeau, C., and Winter, H. 1999. Effect of algae Aphanizomenon flos-aquae on digestive enzyme activity and polyunsaturated fatty acids level in blood plasma. Gastroenterol. 116:A559.
44. Lai, J.-Y., Yu, J., Mekonnen, B., and Falck, J. R. 1996. Synthesis of curacin A, an antimitotic cydopropane-thiazoline from a marine cyanobacterium Lyngbya majuscula. Tetrahedron Lett. 37: 7167-7170.
45. Li, W. I., Berman, F. W., Okino, T., Yokokawa, F., Shioiri, T., Gerwick, W. H., and Murray, T. F. 2001. Antillatoxin is a marine cyanobacterial toxin that potently activates voltage-gated sodium channels. Proc. Natl. Acad. Sci. 98: 7599-7604.
46. Lilleheil, G., Andersen, R. A., Skulberg, O. M., and Alexander, J. 1997. Effects of a homoanatoxin-A-containing extract from Oscillatoria formosa (Cyanophyceae/Cyanobacteria) on neuromuscular transmission. Toxicon. 35: 1275-1289.
47. Mahmood, N. A., and Carmichael, W. W. 1987. Anatoxin-a(s), an anticholinesterase from the cyanobacterium Anabaena flos-aquae NRC 525-517. Toxicon. 25: 1221-1227.
48. Mahmood, N. A., and Carmichael, W. W. 1986. The pharmacology of anatoxin-a(s), a neurotoxin produced by the freshwater cyanobacterium Anabaena flos-aquae NRC 525-17. Toxicon 24: 425-434.
49. Marahiel, M. A., Stachelhaus, T., and Mootz, H. D. 1997. Modular peptides synthetases involved in nonribosomal peptide synthesis. Chem. Rev. 97: 2651-2673.
50. Matern, U., Oberer, L., Falchetto, R. A., Erhard, M., Konig, W. A., Herdman, M., and Weckesser, J. 2001. Scyptolin A and B, cyclic depsipeptides from axenic cultures of Scytonema hofmanni PCC 7110. Phytochem. 58: 1087-1095.
51. Mathew, B., Sankaranarayanan, R., Nair, P. P., Varghese, C., Somanathan, T., Amma, B. P., Amma, N. S., and Nair, M. K. 1995. Evaluation of chemoprevention of oral cancer with Spirulina fusiformis. Nutr. Cancer. 24: 197-202.
52. Matsunaga, S., Moore, R. E., Niemczura, W. P., and Carmichael, W. W. 1989. Anatoxin-a(s), a potent anticholinesterase from Anabaena flos-aquae. J. Am. Chem. Soc. 111: 8021-8023.
53. Mishima, T., Murata, J., Toyoshima, M., Fujii, H., Nakajima, M., Hayashi, T., Kato, T., and Saiki, I. 1998. Inhibition of tumour invasion and metastasis by calcium spirulan (Ca-SP), a novel sulfated polysaccharide derived from a blue-green alga, Spirulina platensis. Clin. Exp. Metastasis. 16: 541-550.
54. Moore, B. S. 1999. Biosynthesis of marine natural products: microorganisms and microalgae. Nat Prod. Rep. 16: 653-673.
55. Moore, R. E., Ohtani, I., Moore, B. S., De Koning, C. B., Yoshida, W. Y., Runnegar, M. T., and Carmichael, W. W. 1993. Cyanobacterial toxins. Gazz. Chim. Ital. 123: 329-336.
56. Moore, R. E., Chen, J. L., Moore, B. S., Patterson, G. M. L., and Carmichael, W. W. 1991. Biosynthesis of microcystin-LR. Origin of the carbons in the adda and masp units. J. Am. Chem. Soc. 113: 5083-5084.
57. Moreno, J., Vargas, M. A., Rodriguez, H., Rivas, J., and Guerrero, M. G. 2003. Outdoor cultivation of a nitrogen-fixing marine cyanobacterium, Anabaena sp. ATCC 33047. Biomol. Engg. 20: 191-197.
58. Mori, T., Barrientos, L. G., Man, Z. Z., Gronenborn, A. M., Turpin, J. A., and Boyd, M. R. 2002. Functional homologs of cyanovirin-N amenable to mass production in prokaryotic and eukaryotic hosts. Protein. Expr. Purif. 26: 42-49.
59. Mori, T., Gustafson, K. R., Pannell, L. K., Shoemaker, R. H., Wu, L., McMahon, J. B., and Boyd, M. R. 1998. Recombinant production of cyanovirin-N, a potent HIV-inactivating protein derived from cultured cyanobacterium. Protein Expr. Purif. 12: 151-158.
60. Neilan, B. A., Dittmann, E., Rouhiainen, L., Bass, R. A., Schaub, V., Sivonen, K., and Borner, T. 1999. Nonribosomal peptide synthesis and toxigenicity of Cyanobacteria J. Bact. 181: 4089-4097.
61. Olaizola, M. 2003. Commercial development of microalgal biotechnology: from the test tube to the marketplace. Biomol. Eng. 20: 459-466.
62. Orjala, J., Nagle, D. G., Hsu, V. L., and Gerwick, W. H. 1995. Antillatoxin: An exceptionally ichthyotoxic cyclic lipopeptide from the tropical cyanobacterium Lyngbya majuscula. J. Am. Chem. Soc. 117:8281-8282.
63. Otero, A., and Vincenzini, M. 2003. Extracellular polysaccharide synthesis by Nostoc strains as affected by N source and light intensity. J. Biotechnol. 102: 143-152.
64. Panda, D., Deluca, K., Williams, D., Jordan, M. A., and Wilson, L. 1998. Antiproliferative mechanism of action of cryptophycin-52: kinetic stabilization of microtubule dynamics by high-affinity binding to microtubule ends. Cell Biol. 95: 9313-9318.
65. Patel, A., Misra, S., Pawar, R., and Ghosh P. K. 2005. Purification and characterization of C-phycocyanin from cyanobacterial sp. Of marine and fresh water habitat. Protein Expr. Purif. 40: 248-255.
66. Pluotno, A., and Carmeli S. 2005. Banyasin A and banyasides A and B, three novel modified peptides from a water bloom of the cyanobacterium Nostoc sp. Tetrahedron. 61: 575-583.
67. Pugh, N., Ross, S. A., ElSohly, H. N., ElSohly, M. A., and Pasco, D. S. 2001. Isolation of three new polysaccharide preparations with potent immunostimulatory activity from Spirulina platensis, Aphanizomenon flos-aquae and Chlorella pyrenoidosa. Planta Medica 67: 737-742.
68. Pulz, O. 2001. Photobioreactors: production system for phototrophic microorganism. Applied Microb. and Biotech, 57: 287-293.
69. Qureshi, M. A., Garlich, J. D., and Kidd, M. T. 1996. Dietary Spirulina platensis enhances humoral and cell-mediated immune function in chickens. Immunopharmacol Immunotoxicol. 18: 465-476.
70. Reddy, C. M., Bhat, V. B., Kiranmai, G., Reddy, M. N., Reddanna, P., and Madyastha, K. M. 2000. Selective inhibition of cydooxygenase-2 by C-phocyanin, a biliprotein from Spirulina platensis. Biochem. Ciophys. Res. Commun. 3: 599-603.
71. Roman, R. B., Alvarez-Pez, J. M., Fernandez, F. G. A., and Grima, E. M. 2002. Recovery of pure B-phycoerythrin from the microalga Porphyridium cruentum. J. Biotechnol. 93: 73-85.
72. Romay, C., Ledon, N., and Gonzalez, R. 1999. Phycocyanin extract reduces leukotriene B4 levels in arachidonic acid-induced mouse-ear inflammation test. J. Pharm. Pharmacol. 51: 641-642.
73. Schwartz, J., Shklar, G., Reid, S., and Trickier, D. 1988. Prevention of experimental oral cancer by extracts of Spirulina-Dunaliella algae. Nutr Cancer. 11: 127-134.
74. Schwartz, J., and Shklar, G., 1987. Regression of experimental hamster cancer by beta-carotene and algae extracts. J. Oral. Maxillofac. Surg. 45: 510-515.
75. Serval, M. O., Claire, C., Darrien, A., Coiffard, L., De Roeck-Holtzhauer, Y. 1994. Fatty acid composition of some marine microalgae. Phytochem. 36: 691.
76. Shimizu, Y. 2003. Microalgal metabolites. Curr. Opin. Microbiol. 6: 236-243.
77. Shimizu, Y. 1986. Toxigenesis and biosynthesis of saxitoxin analogues. Pure Appl. Chem. 58: 257-262.
78. Shimizu, Y., Norte, M., Hori, A., Genenah, A., and Kobayashi, M. 1984. Biosynthesis of saxitoxin analogs: the unexpected pathway. J. Am. Chem. Soc. 106: 6433-6433.
79. Spivak, C. E., Witkop, B., and Albuquerque, E. X. 1980. Anatoxin-a: a novel, potent agonist at the nicotinic receptor. Mol. Pharmacol. 18: 384-394.
80. Stal, L. J., and Moezelaar, R. 1997. Fermentation in cyanobacteria. FEMS Microbiol Rev 21: 179-211.
81. Tokuda, H., Nishino, H., Shirahashi, H., Murakami, N., Nagatsu, A., and Sakakibara, J. 1996. Inhibition of 12-O-tetradecanoylphorbol-13-acetate promoted mouse skin papilloma by digalactosyl diacylglycerols from the fresh water cyanobacterium Phormidium tenue. Cancer Lett. 104:91-95.
82. Vadiraja, B. B., Gaikwad, N. W., and Madyastha, K. M. 1998. Hepatoprotective effect of C- phycocyanin: protection for carbon tetrachloride and R-(+)-pulegone-mediated hepatotoxicty in rats. Biochem. Biophys. Res. Commun. 249: 428-431.
83. Valencia, A., and Walker, J. 1999. The ability of Aphanizomenon flos-aquae from Klamath Lake to improve the outcome of the treatment for mild traumatic brain injury. Presented at the 3rd World Congress on Brain Injury held in Quebec City, 4.
84. Vlad, M., Bordas, E., Caseanu, E., Uza, G., Creteanu, E., and Polinicenco, C. 1995. Effect of cuprofilin on experimental atherosclerosis. Biol. Trace. Elem. Res. 48: 99-109.
85. When, Z., and Chen, F. 2003. Heterotropic production of eicosapentaenoic acid by microalgae. Biotech. Adv. 21: 273-294.
86. Williams, D. E., Craig, M., Dawe, S. C., Kent, M. L., Andersen, R. J., and Holmes, C. F., 1997. 14C-labeled microcystin-LR administered to Atlantic salmon via intraperitoneal injection provides in vivo evidence for covalent binding of microcystin-LR in salmon livers. Toxicon. 35: 985-989.
87. Wu, M., Okino, T., Nogle, L. M., Marquez, B. L., Williamson, R. T., and Sitchitta, N. 2000. Structure, synthesis, and biological properties of kalkitoxin, a novel neurotoxin from the marine cyanobacterium Lyngbya majuscula. J. Am. Chem. Soc. 122: 12041-12042.
88. Yang, F., Bewley, C. A., Louis, J. M., Gustafson, K. R., Boyd, M. R., Gronenborn, A. M., Clore, G. M., and Wlodawer, A. 1999. Crystal structure of cynovirin-N, a potent HIV-inactivating protein, shows unexpected domain swapping. J. Mol. Biol. 288: 403-412.
89. Yang, H., Lee, E., and Kim, H. 1997 Spirulina platensis inhibits anaphylactic reaction. Life Sci. 61: 1237-1244.