Cyclic peptides and depsipeptides from cyanobacteria: A review

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.

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.

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.

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.

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.

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.

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.

Cardellina II JH, F-J Marner and RE Moore. 1979. Seaweed dermatitis: structure of lyngbyatoxin A. Science (Washington, DC) 204: 193–195.

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.

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.

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.

Carmichael WW. 1992. Cyanobacteria secondary metabolites—the cyanotoxins. J Appl Bacteriol 72: 445–449.

Carmichael WW. 1994. The toxins of cyanobacteria. Sci Am 270: 78–86.

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.

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.

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.

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.

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.

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.

Francis G. 1878. Poisonous Australian lake. Nature (Lond) 18: 11–12.

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.

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.

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.

Fukuyama T and L Xu. 1993. Total synthesis of (−)-tantazole B. J Am Chem Soc 115: 8449–8450.

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.

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.

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.

Gerwick WH, MA Roberts, PJ Proteau and JL Chen. 1994. Screening cultured marine microalgae for anticancer-type activity. J Appl Phycol 6: 143–149.

Gregson JM, JL Chen, GML Patterson and RE Moore. 1992. Structures of puwainaphycins A-E. Tetrahedron 48: 3727–3734.

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.

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.

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.

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.

Hirsch CF, JM Liesch, MJ Salvatore, RE Schwartz and DF Sesin. 1990. Antifungal fermentation product and method. US Patent 4946835 Aug.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Moore RE. 1982. Toxins, anticancer agents, and tumor promoters from marine prokaryotes. Pure Appl Chem 54: 1919–1934.

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.

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.

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.

Moore RE and JS Mynderse. 1982. Majusculamide C. US Patent 4342751 Aug.

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.

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.

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.

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.

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.

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.

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.

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.

Patterson GML, LK Larsen and RE Moore. 1991. Bioactive natural products from blue-green algae. J Appl Phycol 6: 151–157.

Pergament I and S Carmeli. 1994. Schizotrin A, a novel antimicrobial cyclic peptide from a cyanobacterium. Tetrahedron Lett 36: 8473–8476.

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.

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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.

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.

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.

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.

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