Journal of Industrial Microbiology

, Volume 16, Issue 2, pp 134–143 | Cite as

Cyclic peptides and depsipeptides from cyanobacteria: A review

  • R E Moore


An elaborate array of structurally-novel and biologically-active cyclic peptides and depsipeptides are found in blue-green algae (cyanobacteria). Several of these compounds possess structures that are similar to those of natural products from marine invertebrates. Most of these cyclic peptides and depsipeptides, such as the microcystins and the lyngbyatoxins, will probably only be useful as biochemical research tools. A few, however, have the potential for development into useful commercial products. For example, cryptophycin-1, a novel inhibitor of microtubule assembly fromNostoc sp GSV 224, shows impressive activity against a broad spectrum of solid tumors implanted in mice, including multidrug-resistant ones, and majusculamide C, a microfilament-depolymerizing agent fromLyngbya majuscula, shows potent fungicidal activity and may have use in the treatment of resistant fungal-induced diseases of domestic plants and agricultural crops.


cyanobacteria natural products hepatotoxins fungicides antitumor agents enzyme inhibitors 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Aimi N, H Odaka, S Sakai, H Fujiki, M Suganuma, RE Moore and GML Patterson. 1990. Lyngbyatoxins B and C, two new irritants fromLyngbya majuscula. J Nat Prod 53: 1593–1596.PubMedGoogle Scholar
  2. 2.
    Andersen RJ, DL Burgoyne, DE Williams, F Kong, ED de Silva, S Miao, TM Allen, CFB Holmes, D Chen and M Kent. 1993. New natural products from marine invertebrates. Gazz Chim Ital 123: 293–300.Google Scholar
  3. 3.
    Andersen RJ, HA Luu, DZX Chen, CFB Holmes, ML Kent, M Le Blanc, FJR ‘Max’ Taylor and DE Williams. 1993. Chemical and biological evidence links microcystin-LR to salmon ‘netpen liver disease’. Toxicon 31: 1315–1323.PubMedGoogle Scholar
  4. 4.
    Barrow R, T Hemscheidt, S Paik, J Liang, RE Moore and MA Tius. 1995. Total synthesis of cryptophycins. Revision of the structures of cryptophycins A and C. J Am Chem Soc 117: 2479–2490.Google Scholar
  5. 5.
    Bishop CT, EFLJ Anet and PR Gorham. 1959. Isolation and identification of the fast-death factor inMicrocystis aeruginosa NRC-1. Can J Biochem Physiol 37: 453–471.PubMedGoogle Scholar
  6. 6.
    Botes DP, AA Tuinman, PL Wessels, CC Viljoen, H Kruger, DH Williams, S Santikarn, RJ Smith and SJ Hammond. 1984. The structure of cyanoginosin-LA, a cyclic heptapeptide toxin from the cyanobacteriumMicrocystis aeruginosa. J Chem Soc Perkin Trans 1: 2311–2318.Google Scholar
  7. 7.
    Botes DP, PL Wessels, H Kruger, MTC Runnegar, S Santikarn, RJ Smith, JCJ Barna and DH Williams. 1985. Structural studies on cyanoginosins-LR,-YR,-YA and-YM, peptide toxins fromMicrocystis aeruginosa. J Chem Soc Perkin Trans I: 2747–2748.Google Scholar
  8. 8.
    Cardellina II JH, F-J Marner and RE Moore. 1979. Seaweed dermatitis: structure of lyngbyatoxin A. Science (Washington, DC) 204: 193–195.Google Scholar
  9. 9.
    Carmeli S, RE Moore and GML Patterson. 1991. Mirabazoles, minor tantazole-related cytotoxins from the terrestrial blue-green algaScytonema mirabile. Tetrahedron Lett 32: 2593–2596.Google Scholar
  10. 10.
    Carmeli S, RE Moore, GML Patterson, TH Corbett and FA Valeriote. 1990. Tantazoles, unusual cytotoxic alkaloids from the blue-green algaScytonema mirabile. J Am Chem Soc 112: 8195–8197.Google Scholar
  11. 11.
    Carmeli S, S Paik, RE Moore, GML Patterson and WY Yoshida. 1993. Revised structures and biosynthetic studies of tantazoles A and B. Tetrahedron Lett 34: 6681–6684.Google Scholar
  12. 12.
    Carmichael WW. 1992. Cyanobacteria secondary metabolites—the cyanotoxins. J Appl Bacteriol 72: 445–449.PubMedGoogle Scholar
  13. 13.
    Carmichael WW. 1994. The toxins of cyanobacteria. Sci Am 270: 78–86.PubMedGoogle Scholar
  14. 14.
    Carmichael WW, V Beasley, DL Bunner, JN Eloff, I Falconer, P Gorham, K Harada, T Krishnamurthy, Y Min-Juan, RE Moore, K Rinehart, M Runnegar, OM Skulberg and M Watanabe. 1988. Letter to the editor. Naming of cyclic heptapeptide toxins of cyanobacteria (blue-green algae). Toxicon 26: 971–973.PubMedGoogle Scholar
  15. 15.
    Carter DC, RE Moore, JS Mynderse, WP Niemczura and JS Todd. 1984. Structure of majusculamide C, a cyclic depsipeptide fromLyngbya majuscula. J Org Chem 49: 236–241.Google Scholar
  16. 16.
    de Silva ED, DE Williams, RJ Andersen, H Klix, CFB Holmes and TM Allen. 1992. Motuporin, a potent protein phosphatase inhibitor isolated from the Papua New Guinea spongeTheonella swinhoei Gray. Tetrahedron Lett 33: 1561–1564.Google Scholar
  17. 17.
    Degnan BM, CJ Hawkins, MF Lavin, EJ McCaffrey, DL Parry, AL van den Brenk and DJ Watters. 1989. New cyclic peptides with cytotoxic activity from the ascidianLissoclinum patella. J Med Chem 32: 1349–1354.PubMedGoogle Scholar
  18. 18.
    Degnan BM, CJ Hawkins, MF Lavin, EJ McCaffrey, DL Parry and DJ Watters. 1989. Novel cytotoxic compounds from the ascidianLissoclinum bistratum. J Med Chem 32: 1354–1359.PubMedGoogle Scholar
  19. 19.
    Falconer IR, AM Beresford and MTC Runnegar. 1983. Evidence of liver damage by toxin from a bloom of the blue-green alga,Microcystis aeruginosa. Med J Aust 1: 511–514.PubMedGoogle Scholar
  20. 20.
    Francis G. 1878. Poisonous Australian lake. Nature (Lond) 18: 11–12.Google Scholar
  21. 21.
    Frankmölle WP, G Knübel, RE Moore and GML Patterson. 1992. Antifungal cyclic peptides from the blue-green algaAnabaena laxa. II. Structures of laxaphycins A, B, D and E. J Antibiotics 45: 1458–1466.Google Scholar
  22. 22.
    Frankmölle WP, LK Larsen, F Caplan, GML Patterson, G Knübel, IA Levine and RE Moore. 1992. Antifungal cyclic peptides from the bluegreen algaAnabaena laxa. I. Isolation and biological properties. J Antibiotics 45: 1451–1457.Google Scholar
  23. 23.
    Fujiki H, M Suganuma, H Hakii, G Bartolini, RE Moore, S Takayama and T Sugimura. 1984. A two-stage mouse skin carcinogenesis study of lyngbyatoxin A. J Cancer Res Clin Oncol 108: 174–176.PubMedGoogle Scholar
  24. 24.
    Fukuyama T and L Xu. 1993. Total synthesis of (−)-tantazole B. J Am Chem Soc 115: 8449–8450.Google Scholar
  25. 25.
    Golakoti T, J Ogino, CE Heltzel, TL Husebo, CM Jensen, LK Larsen, GML Patterson, RE Moore, SL Mooberry, TH Corbett and FA Valeriote. 1995. Structure determination, conformational analysis, chemical stability studies and antitumor evaluation of the cryptophycins. Isolation of eighteen new analogs fromNostoc sp strain GSV 224. J Am Chem Soc 117: 12030–12049.Google Scholar
  26. 26.
    Gerwick WH, ZD Jiang, SK Agarwal and BT Farmer. 1992. Total structure of hormothamnin A, a toxic cyclic undecapeptide from the tropical marine cyanobacteriumHormothamnion enteromorphoides. Tetrahedron 48: 2313–2324.Google Scholar
  27. 27.
    Gerwick WH, CH Mrozek, MF Moghaddam and SK Agarwal. 1989. Novel cytotoxic peptides from the tropical marine cyanobacteriumHormothamnion enteromorphoides. 1. Discovery, isolation and initial chemical and biological characterization of the hormothamnins from wild and cultured material. Experientia 45: 115–121.PubMedGoogle Scholar
  28. 28.
    Gerwick WH, MA Roberts, PJ Proteau and JL Chen. 1994. Screening cultured marine microalgae for anticancer-type activity. J Appl Phycol 6: 143–149.Google Scholar
  29. 29.
    Gregson JM, JL Chen, GML Patterson and RE Moore. 1992. Structures of puwainaphycins A-E. Tetrahedron 48: 3727–3734.Google Scholar
  30. 30.
    Hambley TW, CJ Hawkins, MF Lavin, A Van den Brenk and DJ Watters. 1991. Cycloxazoline: a cytotoxic cyclic hexapeptide from the ascidianLissoclinum bistratum. Tetrahedron 48: 341–348.Google Scholar
  31. 31.
    Harada K-i, K Fujii, T Shimada, M Suzuki, H Sano, K Adachi and WW Carmichael. 1995. Two cyclic peptides, anabaenopeptins, a third group of bioactive compounds from the cyanobacteriumAnabaena flos-aquae NRC 525-17. Tetrahedron Lett 36: 1511–1514.Google Scholar
  32. 32.
    Harada K-i, T Mayumi, T Shimada, M Suzuki, F Kondo and MF Watanabe. 1993. Occurrence of four depsipeptides, aeruginopeptins, together with microcystins from toxic cyanobacteria. Tetrahedron Lett 34: 6091–6094.Google Scholar
  33. 33.
    Helms GL, RE Moore, WP Niemczyra, GML Patterson, KB Tomer and ML Gross. 1988. Scytonemin A, a novel calcium antagonist from a blue-green alga. J Org Chem 53: 1298–1307.Google Scholar
  34. 34.
    Hirsch CF, JM Liesch, MJ Salvatore, RE Schwartz and DF Sesin. 1990. Antifungal fermentation product and method. US Patent 4946835 Aug.Google Scholar
  35. 35.
    Honkanen RE, FR Caplan, KK Baker, CL Baldwin, SC Bobzin, CM Bolis, GM Cabrera, LA Johnson, LK Larsen, IA Levine, RE Moore, CS Nelson, GML Patterson, KD Tschappat, GD Tuang, AL Boynton, AR Arment, J An, WW Carmichael, KD Rodland, BE Magun and RA Lewin. 1995. Protein phosphatase inhibitory activity in extracts of cultured blue-green algae (Cyanophyta). J Phycol 31: 478–486.Google Scholar
  36. 36.
    Honkanen RE, J Zwiller, RE Moore, SL Daily, BS Khatra, M Dukelow and AL Boynton. 1990. Characterization of microcystin, a potent inhibitor of type 1 and type 2A protein phosphatases. J Biol Chem 265: 19401–19404.PubMedGoogle Scholar
  37. 37.
    Honkanen RE, J Zwiller, SL Daily, BS Khatra, M Dukelow and AL Boynton. 1991. Identification, purification, and characterization of a novel serine/threonine protein phosphatase from bovine brain. J Biol Chem 266: 6614–6619.PubMedGoogle Scholar
  38. 38.
    Honkanen RE, M Dukelow, J Zwiller, RE Moore, BS Khatra and AL Boynton. 1991. Cyanobacterial nodularin is a potent inhibitor of type 1 and type 2A protein phosphatases. Mol Pharm 40: 577–583.Google Scholar
  39. 39.
    Ishida K, M Murakami, H Matsuda and K Yamaguchi. 1995. Micropeptin 90, a plasmin and trypsin inhibitor from the blue-green algaMicrocystis aeruginosa (NIES-90). Tetrahedron Lett 36: 3535–3538.Google Scholar
  40. 40.
    Ishitsuka MO, T Kusumi, H Kakisawa, K Kaya and MM Watanabe. 1990. Microviridin: a novel tricyclic depsipeptide from the toxic cyanobacteriumMicrocystis viridis. J Am Chem Soc 112: 8180–8182.Google Scholar
  41. 41.
    Izumi AK and RE Moore. 1987. Seaweed (Lyngbya majuscula) dermatitis. In: Clinics in Dermatology (Aquatic Dermatology) (Mandojana R, ed), pp 92–100, Harper and Row, Scranton, PA.Google Scholar
  42. 42.
    Jakobi C, L Oberer, C Quiquerez, WA König and J Weckesser. 1995. Cyanopeptolin S, a sulfate-containing depsipeptide from a water bloom ofMicrocystis sp. FEMS Microbiol Lett 129: 129–134.PubMedGoogle Scholar
  43. 43.
    Kobayashi J, M Sato, M Ishibashi, H Shigemori, T Nakamura and Y Ohizumi. 1991. Keramamide A, a novel peptide from the Okinawan marine spongeTheonella sp. J Chem Soc Perkin Trans 1: 2609–2611.Google Scholar
  44. 44.
    Kobayashi J, M Sato, T Murayama, M Ishibashi, MR Wälchi, M Kanai, J Shoji and Y Ohizumi. 1991. Konbamide, a novel peptide with calmodulan antagonistic activity from the Okinawan marine spongeTheonella sp. J Chem Soc Chem Commun: 1050–1052.Google Scholar
  45. 45.
    Kobayashi M, S Aoki, N Ohyabu, M Kurosu, W Wang and I Kitagava. 1994. Arenastatin A, a potent cytotoxic depsipeptide from the Okinawan marine spongeDysidea arenaria. Tetrahedron Lett 35: 7969–7972.Google Scholar
  46. 46.
    Kobayashi M, M Kurosu, N Ohyabu, W Wang, S Fujii and I Kitagawa. 1994. The absolute stereostructure of arenastatin A, a potent cytotoxic depsipeptide fom the Okinawan marine spongeDysidea arenaria. Chem Pharm Bull 42: 2196–2198.Google Scholar
  47. 47.
    Kobayashi M, M Kurosu, W Wang and I Kitagawa. 1994. A total synthesis of arenastatin A, an extremely potent cytotoxic depsipeptide, from the Okinawan marine spongeDysidea arenaria. Chem Pharm Bull 42: 2394–2396.Google Scholar
  48. 48.
    Lau AF, J Siedlecki, J Anleitner, GML Patterson, FR Caplan and RE Moore. 1993. Inhibition of reverse transcriptase activity by extracts of cultured blue-green algae. Planta Medica 59: 148–151.PubMedGoogle Scholar
  49. 49.
    Lee AY, TA Smitka, R Bonjouklian and J Clardy. 1994. Atomic structure of the trypsin-A90720A complex: a unified approach to structure and function. Chem Biol 1: 113–117.PubMedGoogle Scholar
  50. 50.
    MacKintosh C, KA Beattie, S Klumpp, P Cohen and GA Codd. 1990. Cyanobacterial microcystin-LR is a potent and specific inhibitor of protein phosphatases 1 and 2A from both mammals and higher plants. FEBS Lett 264: 187–192.PubMedGoogle Scholar
  51. 51.
    Martin C, L Oberer, T Ino, WA König, M Busch and J Weckesser. 1993. Cyanopeptolins, new depsipeptides from the cyanobacteriumMicrocystis sp PCC 7806. J Antibiotics 46: 1550–1556.Google Scholar
  52. 52.
    Moon S-S, JL Chen, RE Moore and GML Patterson. 1992. Calophycin, a fungicidal cyclic decapeptide from the terrestrial blue-green algaCalothrix fusca. J Org Chem 57: 1097–1103.Google Scholar
  53. 53.
    Moore RE. 1982. Toxins, anticancer agents, and tumor promoters from marine prokaryotes. Pure Appl Chem 54: 1919–1934.Google Scholar
  54. 54.
    Moore RE. 1984. Public health and toxins from marine blue-green algae. In: Seafood Toxins (ACS Symposium Series, no 262) (Ragelis EP, ed), pp 369–376, Am Chem Soc, Washington.Google Scholar
  55. 55.
    Moore RE, AJ Blackman, CE Cheuk, JS Mynderse, GK Matsumoto, J Clardy, RW Woodard and JC Craig. 1984. Absolute stereochemistries of the aplysiatoxins and oscillatoxin A. J Org Chem 49: 2484–2489.Google Scholar
  56. 56.
    Moore RE, V Bornemann, WP Niemczura, JM Gregson, JL Chen, TR Norton, GML Patterson and GL Helms. 1989. Puwainaphycin C, a cardioactive cyclic peptide from the blue-green algaAnabaena BQ-16-1. Use of two-dimensional13C−13C and13C−15N correlation spectroscopy in sequencing the amino acid units. J Am Chem Soc 111: 6128–6132.Google Scholar
  57. 57.
    Moore RE and JS Mynderse. 1982. Majusculamide C. US Patent 4342751 Aug.Google Scholar
  58. 58.
    Moore RE, GML Patterson and WW Carmichael. 1988. New pharmaceuticals from cultured blue-green algae. In: Biomedical Importance of Marine Organisms (Fautin D, ed), pp 143–150, Cal Acad Sci, San Francisco.Google Scholar
  59. 59.
    Nishiwaki-Matsushima R, T Ohta, S Nishiwaki, M Suganuma, K Kohyama, T Ishikawa, WW Carmichael and H Fujiki. 1992. Liver tumor promotion by the cyanobacterial cyclic peptide toxin microcystin-LR. J Cancer Res Clin Oncol 118: 420–424.PubMedGoogle Scholar
  60. 60.
    Ohta T, E Sueoka, N Iida, A Komori, M Suganuma, R Nishiwaki, M Tatematsu, S-J Kim, WW Carmichael and H Fujiki. 1994. Nodularin, a potent inhibitor of protein phosphatases 1 and 2A, is a new environmental carcinogen in male F344 rat liver. Cancer Res 54: 6402–6406.PubMedGoogle Scholar
  61. 61.
    Okino T, M Murakami, R Haraguchi, H Munekata, H Matsuda and K Yamaguchi. 1993. Micropeptins A and B, plasmin and trypsin inhibitors from the blue-green algaMicrocystis aeruginosa. Tetrahedron Lett 34: 8131–8134.Google Scholar
  62. 62.
    Orjala J, DG Nagle, V Hsu and WH Gerwick. 1995. Antillatoxin, an exceptionally ichthyotoxic cyclic lipopeptide from the tropical cyanobacteriumLyngbya majuscula. J Am Chem Soc 117: 8281–8282.Google Scholar
  63. 63.
    Pattenden G and SM Thom. 1993. Naturally occurring linear fused thiazoline-thiazole containing metabolites: total synthesis of (−)-didehydromirabazole A, a cytotoxic alkaloid from blue-green algae. J Chem Soc Perkin Trans I: 1629–1636.Google Scholar
  64. 64.
    Patterson GML, KK Baker, CL Baldwin, CM Bolis, FR Caplan, LK Larsen, IA Levine, RE Moore, CS Nelson, KD Tschappat, GD Tuang, MR Boyd, JH Cardellina II, RP Collins, KR Gustafson, KM Snader and OS Weislow. 1993. Antiviral activity of cultured blue-green algae (Cyanophyta). J Phycol 29: 125–130.Google Scholar
  65. 65.
    Patterson GML, CL Baldwin, CM Bolis, FR Caplan, H Karuso, LK Larsen, IA Levine, RE Moore, CS Nelson, KD Tschappat, GD Tuang, E Furusawa, S Furusawa, TR Norton and RB Raybourne. 1991. Anti-neoplastic activity of cultured blue-green algae (Cyanophyta). J Phycol 27: 530–536.Google Scholar
  66. 66.
    Patterson GML, LK Larsen and RE Moore. 1991. Bioactive natural products from blue-green algae. J Appl Phycol 6: 151–157.Google Scholar
  67. 67.
    Pergament I and S Carmeli. 1994. Schizotrin A, a novel antimicrobial cyclic peptide from a cyanobacterium. Tetrahedron Lett 36: 8473–8476.Google Scholar
  68. 68.
    Pettit GR, Y Kamano, CL Herald, C Dufresne, RL Cerny, DL Herald, JM Schmidt and H Kizu. 1989. Isolation and structure of the cytostatic depsipeptide dolastatin 13 from the sea hareDolabella auricularia. J Am Chem Soc 111: 5015–5017.Google Scholar
  69. 69.
    Pettit GR, Y Kamano, CW Holzapfel, WJ Van Zyl, AA Tuinman, CL Herald, L Baczynskyj and JM Schmidt. 1987. Antineoplastic agents. 150. The structure and synthesis of dolastatin 3. J Am Chem Soc 109: 7581–7582.Google Scholar
  70. 70.
    Pettit GR, Y Kamano, H Kizu, C Dufresne, CL Herald, RJ Bontems, JM Schmidt, FE Boettner and RA Nieman. 1989. Isolation and structure of the cell growth inhibitory depsipeptides dolastatins 11 and 12. Heterocycles 28: 553–558.Google Scholar
  71. 71.
    Prinsep MR, RE Moore, IA Levine and GML Patterson. 1992. Westiellamide, a bistratamide-related cyclic peptide from the blue-green algaWestiellopsis prolifica. J Nat Prod 55: 140–142.PubMedGoogle Scholar
  72. 72.
    Prinsep MR, FR Caplan, RE Moore, GML Patterson, RE Honkanen and AL Boynton. 1991. Microcystin-LA from a blue-green alga belonging to the Stigonematales. Phytochemistry 31: 1247–1248.Google Scholar
  73. 73.
    Rinehart KL, K Harada, M Namikoshi, C Chen, CA Harvis, MHG Munro, JW Blunt, PE Mulligan, VR Beasley, AM Dahlem and WW Carmichael. 1988. Nodularin, microcystin, and the configuration of Adda. J Am Chem Soc 110: 8557–8558.Google Scholar
  74. 74.
    Rinehart KL, M Namikoshi and BW Choi. 1994. Structure and biosynthesis of toxins from blue-green algae (cyanobacteria). J Appl Phycol 6: 159–176.Google Scholar
  75. 75.
    Sakai S, Y Hitotsuyanagi, N Aimi, H Fujiki, M Suganuma, T Sugimura, Y Endo and K Shudo. 1986. Absolute configuration of lyngbyatoxin A (teleocidin A-1) and teleocidin A-2. Tetrahedron Lett 27: 5219–5220.Google Scholar
  76. 76.
    Santikarn S, DH Williams, RJ Smith, SJ Hammond, DP Botes, A Tuinman, PL Wessels, CC Viljoen and H Kruger. 1983. A partial structure for the toxin BE-4 from the blue-green algaMicrocystis aeruginosa. J Chem Soc Chem Commun: 652–654.Google Scholar
  77. 77.
    Schwartz RE, CF Hirsch, DF Sesin, JE Flor, M Chartrain, RE Fromtling, GH Harris, MJ Salvatore, JM Liesch and K Yudin. 1990. Pharmaceuticals from cultured algae. J Ind Microbiol 5: 113–124.Google Scholar
  78. 78.
    Shin HJ, M Murakami, H Matsuda, K Ishida and K Yamaguchi. 1995. Oscillapeptin, an elastase and chymotrypsin inhibitor from the cyanobacteriumOscillatoria agardhii (NIES-204). Tetrahedron Lett 36: 5235–5238.Google Scholar
  79. 79.
    Sims JK and RD Zandee Van Rilland. 1981. Escharotic stomatitis caused by the ‘stinging seaweed’Microcoleus lyngbyaceus (formerlyLyngbya majuscula): a case report and review of literature. Hawaii Med J 40: 243–248.PubMedGoogle Scholar
  80. 80.
    Smith CD, X Zhang, SL Mooberry, GML Patterson and RE Moore. 1994. Cryptophycin, a new microtubule depolymerizing agent from cyanobacteria. Cancer Res 54: 3779–3784.PubMedGoogle Scholar
  81. 81.
    Stratmann, K, DL Burgoyne, RE Moore and GML Patterson. 1994. Hapalosin, a cyanobacterial cyclic depsipeptide with multidrug-resistance reversing activity. J Org Chem 59: 7219–7226.Google Scholar
  82. 82.
    Trimurtulu G, I Ohtani, GML Patterson, RE Moore, TH Corbett, FA Valeriote and L Demchik. 1994. Total structures of cryptophycins, potent antitumor depsipeptides from the blue-green algaNostoc sp strain GSV 224. J Am Chem Soc 116: 4729–4737.Google Scholar
  83. 83.
    Tsukamoto S, P Painuly, KA Young, X Yang, Y Shimizu and L Cornell. 1993. Microcystilide A, a novel cell-differentiation-promoting depsipeptide fromMicrocystis aeruginosa NO-15-1840. J Am Chem Soc 115: 11046–11047.Google Scholar
  84. 84.
    Valeriote F, RE Moore, GML Patterson, VP Paul, PJ Scheuer and T Corbett. 1994. Discovery of natural products from microalgae and marine organisms. In: Anticancer Drug Discovery and Development: Natural Products and New Molecular Models (Valeriote FA, TH Corbett and LH Baker, eds), pp 1–25, Kluwer Academic Publishers, Norwell.Google Scholar
  85. 85.
    Wilkinson CR. 1979. Nutrient translocation from symbiotic cyanobacteria to coral reef sponges. In: Biologie de Spongiaires (Sponge Biology) Vol 291 (Levi C and N Boury Esnault, eds), pp 373–380, Colloq Internat CNRS, Paris.Google Scholar
  86. 86.
    Williams DE, DL Burgoyne, SJ Rettig, RJ Anderson, ZR Fathi-Afshar and TM Allen. 1993. The isolation of majusculamide C from the spongePtilocaulis trachys collected in Enewetak and determination of the absolute configuration of the 2-methyl-3-aminopentanoic acid residue. J Nat Prod 56: 545–551.Google Scholar
  87. 87.
    Yoshizawa S, R Matsushima, MF Watanabe, K-i Harada, A Ichihara, WW Carmichael and H Fujiki. 1990. Inhibition of protein phosphatases by microcystin and nodularin associated with hepatotoxicity. J Cancer Res Clin Oncol 116: 609–614.PubMedGoogle Scholar
  88. 88.
    Yu S-Z. 1989. Drinking water and primary liver cancer. In: Primary Liver Cancer (Tang ZY, MC Wu and SS Xia, eds), pp 30–37, Springer-Verlag, Berlin/Heidelberg.Google Scholar

Copyright information

© Society for Industrial Microbiology 1996

Authors and Affiliations

  • R E Moore
    • 1
  1. 1.Department of ChemistryUniversity of HawaiiHonoluluUSA

Personalised recommendations