Abstract
Marine organisms produce novel molecules with remarkable biological activities. Among them, compounds with long carbon chains have become research objectives for chemists and biologists. These molecules, consisting of a long carbon backbone, are usually functionalized with a large number of oxygen atoms, in the form of hydroxyl, ether, and carbonyl groups. This chapter reviews recent developments of these marine-derived bioactive long carbon chain polyethers.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Josefsson B (1980) In: Scheuer PJ (ed) Marine natural products, chemical and biological perspectives, vol 3, Academic, New York, p 1
Westley JW (1983) (ed) Polyether antibiotics, naturally occurring acid ionophores, vol 2: Chemistry, Marcel Dekker, New York
Corey EJ, Cheng X-M (1989) The logic of chemical synthesis, John Wiley, New York
Baker JT, Murphy V (1976) Handbook of marine science, compounds from marine organisms, vol 1, CRC Press, Cleveland, OH
Baker JT, Murphy V (1981) Handbook of marine science, compounds from marine organisms, vol 2, CRC Press, Boca Raton, FL
Faulkner DJ (1984a) Nat. Prod. Rep. 1: 251
Faulkner DJ (1984b) Nat. Prod. Rep. 1: 551
Faulkner DJ (1986) Nat. Prod. Rep. 3: 1
Faulkner DJ (1987) Nat. Prod. Rep. 4: 539.
Faulkner DJ (1988) Nat. Prod. Rep. 5: 613
Moore RE (1985) Prog. Chem. Org. Nat. Prod. 48: 81.
Hirata Y, Uemura D, Ohizumi Y (1988) In: Tu AA (ed) Handbook of natural toxins: marine toxins and venoms, vol 3, Marcel Dekker, New York, p 241
Nakanishi K (1988) In: Fautin DG (ed) Biomedical Importance of marine organisms, California Academy of Sciences, San Francisco, p 59
Yokoyama A, Murata M, Oshima Y. Iwashita T, Yasumoto T (1988) J. Biochem. 104: 184
Tachibana K, Scheuer PJ, Tsukitani Y, Kikuchi, H, Van Engen, D, Clardy J, Gopichand, Y, Schmitz FJ (1981) J. Am. Chem. Soc. 103: 2469
Paul VJ (1988) In: Fautin DG (ed) Biomedical importance of marine organisms, California Academy of Sciences, San Francisco, p 23
Munro MHG, Luibrand RT, Blunt JW (1987) In: Scheuer PJ (ed) Bioorganic Marine Chemistry, vol 1, Springer, Berlin Heidelberg New York, p 93
Fautin DG (1988) (ed) Biomedical importance of marine organisms, California Academy of Sciences, San Francisco
Moore RE, Scheuer PJ (1971) Science 172: 495
Banner AH (1976) In: Jones OA, Endean R (eds) Biology and geology of coral reefs, vol 3, Academic, New York, p 177
Hashimoto Y (1979) In: Marine toxins and other bioactive marine metabolites, Japan Scientific Societies Press, Tokyo p 91
Scheuer PJ (1977) Acc. Chem. Res. 10: 91.
Hashimoto Y, Fusetani N, Kimura S (1969) Bull. Jpn. Soc. Sci. Fish. 35: 1086
Kimura S, Hashimoto Y (1973) Publ. Seto Mar. Biol. Lab. 20: 713
Kimura S, Hashimoto Y, Yamazato K (1973) Toxicon 60: 611
Uemura D, Hirata Y, Iwashita T, Naoki H (1985) Tetrahedron 41: 1007
Armstrong RW, Beau J-M, Cheon SH, Christ WJ, Fujioka H, Ham W-H, Hawkins LD, Jin H, Kang SH, Kishi Y, Martinelli MJ, McWhorter, Jr. WW, Mizuno M, Nakata, M, Stutz AE, Talamas FX, Taniguchi M, Tino JA, Ueda K, Uenishi J, White JB, Yonaga M (1989) J. Am. Chem. Soc. 111: 7525
Uemura D, Ueda K, Hirata Y, Naoki H, Iwashita T (1981) Tetrahedron Lett. 22: 2781
Moore RE, Bartolini G (1981) J. Am. Chem. Soc. 103: 2491
Uemura D, Ueda K, Hirata Y, Katayama C, Tanaka J (1980) Tetrahedron Lett. 21: 4861
Klein LL, McWhorter, Jr. WW, Ko SS, Pfaff K-P, Kishi Y, Uemura D, Hirata Y (1982) J. Am. Chem. Soc. 104: 7362
Ko SS, Finan JM, Yonaga M, Kishi Y, Uemura D, Hirata Y (1982) J. Am. Chem. Soc. 104: 7364
Fujioka H, Christ WJ, Cha JK, Leder J, Kishi Y, Uemura D, Hirata Y (1982) J. Am. Chem. Soc. 104: 7367
Cha JK, Christ WJ, Finan JM, Fujioka H, Kishi Y, Klein LL, Ko SS, Leder J. McWhorter, Jr. WW, Pfaff K-P, Yonaga M, Uemura D, Hirata Y (1982) J. Am. Chem. Soc. 104: 7369
Kishi Y (1983) In: Nozaki H (ed) IUPAC current trends in organic synthesis, Pergamon, Oxford, p 115
Moore RE, Bartolini G, Barchi J, Bothner-By AA (1982) J. Am. Chem. Soc. 104: 3776
Moore RE (1985) Prog. Chem. Org. Nat. Prod. 48: 81 and Moore RE, Helfrich, Patterson GML (1982) Oceanus 25: 54
Amstrong RW, Beau JM, Cheon SH, Christ WJ, Fujioka H, Ham W-H, Hawkins LD, Jin H, Kang SH, Kishi Y, Martinelli MJ, McWhorter, Jr. WW, Mizuno M, Nakata M, Stutz AE, Talamas FX, Taniguchi M. Tino JA, Ueda K, Uenishi J, White JB, Yonaga M (1989) J. Am. Chem. Soc. 111: 7530
Fox JL (1982) Chem. Eng. News 60 (1): 19
Shimizu Y (1983) Nature 302: 212
Stinson SC (1989) Chem. Eng. News 67 (38): 23
Mann J (1989) Nature 342: 227
Wiles JS, Vick JA, Christensen (1974) Toxicon 12: 427
Vick JA, Wiles JS (1975) Toxicol. Appl. Pharmacol. 34: 214
Seltzer RJ (1974) Chem. Eng. News 52 (50): 20
Ito K, Karaki H, Urakawa N (1977) Eur. J. Pharmacol. 46: 9
Ohizumi Y, Shibata S (1980) J. Pharmacol. Exp. Ther. 214: 209
Ozaki H, Nagase H, Urakawa N (1984) J. Pharmacol. Exp. Ther. 231: 153
Ishida Y, Kajiwara A, Takagi K, Ohizumi Y, Shibata S (1985) J. Pharmacol. Exp. Ther. 232: 551
Ahnert-Hilger G, Chhatawal GS, Hessler HJ, Habermann E (1982) Biochim. Biophys. Acta 688: 486
Muramatsu I, Nishio M, Kigoshi S, Uemura D (1988) Br. J. Pharmacol. 93: 811
Muramatsu I, Nishio M (1989) personal communication
Quinn RJ, Kashiwagi M, Moore RE, Norton TR (1974) J. Pharm. Sci. 63: 257
Uemura D, Hirata Y (1989) In: Atta-ur-Rahman (ed) Studies in natural products chemistry, vol 5 (part B), Elsevier, Amsterdam, p 377
Fujiki H, Sugimura T (1987) Advances in Cancer Research 49: 233
Wattenberg EV, Uemura D, Bryron KL, Villereal ML, Fujiki H, Rosner MR (1989) Cancer Res. 49: 5837
Yasumoto T, Yasumura D, Ohizumi Y, Takahashi M, Alcala AC, Alcala LC (1986) Agric. Biol. Chem. 50: 163
Fukui M, Murata M, Inoeu A, Gawel M, Yasumoto T (1987) Toxicon 25: 1121
Maeda M, Kodama T, Tanaka T, Yoshizumi H, Nomoto K, Takemoto T, Fujita T (1985) Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 27: 616
Levine L, Fujiki H, Gjika HB, Vunakis HV (1988) Toxicon 26: 1115
Hirata Y, Uemura D (1986) Pure Appl. Chem. 58: 701
Uemura D, Takahashi K, Yamamoto T, Katayama C, Tanaka J, Okumura Y, Hirata Y (1985) J. Am. Chem. Soc. 107: 4796
Aichar TD, Kishi Y (1987) Tetrahedron Lett. 28: 3463
Aichar TD (1989) Ph.D. Dissertation, Harvard University
Kim S, Salomon RG (1989) Tetrahedron Lett. 30: 6279
Yazawa K, Araki K, Okazaki N, Watanabe K, Ishikawa C, Inoue A, Numao N, Kondo K (1988) J. Biochem. 103: 5
Pettit GR, Herald CL, Doubek DL, Herald DL, Arnold E, Clardy J (1982) J. Am. Chem. Soc. 104: 6846
Pettit GR, Kamano K, Aoyagi R, Herald CL, Doubek DL, Schmidt JM, Rudloe JJ (1985) Tetrahedron 41: 985
Fox JL (1982) Chem. Eng. News 60 (49): 29
Kageyama M, Tamura T, Nantz MH, Roberts JC, Somfai P, Whritenour DC, Masamune S (1990) J. Am. Chem. Soc. 112: 7407
Schmitz FJ, Prasad RS, Gopichand Y, Houssain MB, van der Helm D, Schmidt P (1981) J. Am. Chem. Soc. 103: 2467
Yasumoto T, Murata M, Oshima Y, Sano M, Matsumoto GK, Clardy J (1985) Tetrahedron 41: 1019
Yasumoto T, Murata M, Oshima Y, Matsumoto GK, Clardy J (1984) in: Ragelis EP (ed) Seafood toxins, ACS Symposium Series 262 Am. Chem. Soc., Washington DC, p 207
Yasumoto T, Oshima Y, Yamaguchi M (1978) Bull. Jpn. Soc. Sci. Fish. 44: 1249
Shibata S, Ishida Y, Kitano H, Ohizuni Y, Habon J, Tsukitani Y, Kikuchi H (1982) J. Pharmacol. Exp. Ther. 223: 135
Takai A, Bialojan C, Troschka M, Ruegg JC (1987) FEBS Lett. 217: 81
Bialojan C, Takai A (1988) Biochem J. 256: 283
Cohen P (1989) Ann. Rev. Biochem. 58: 453
Haystead TJ, Sim ATR, Carling D, Honnor RC, Tsukitani Y, Cohen P, Hardie DG (1989) Nature 337: 78
Karaki H, Mitsui M, Nagase H, Ozaki H, Shibata S, Uemura D (1989) Br. J. Pharmacol. 98: 590
Suganuma M, Fujiki H, Suguri H, Yoshizawa S, Hirota M, Nakayama M, Ojika M, Wakamatsu K, Yamada K, Sugimura T (1988) Proc. Natl. Acad. Sci. USA 85: 1768
Cohen P, Holmes CFB, Tsukitani Y (1990) Trends Biochem. Sci. 15: 98
Kato Y, Fusetani N, Matsunaga S, Hashimoto K (1986) J. Am. Chem. Soc. 108: 2780
Ishihara H, Martin BL, Brautigen DL, Karaki H, Ozaki H, Kato Y, Fusetani N, Watabe S, Hashimoto K, Uemura D, Hartshorne DJ (1989) Biochem. Biophys. Res. Commun. 159: 871
Fujiki H, Suganuma M, Yoshizawa S, Kanazawa H, Sugimura T, Manam S, Kahn SM, Jiang W, Hoshina S, Weinstein IB (1989) Molecular Carcinogenesis 2: 184
Fusetani N (1987) In: Scheuer PJ (ed) Bioorganic marine chemistry, vol 1, Springer, Berlin Heidelberg New York, p 61
Kato Y, Fusetani N, Matsunaga S, Hashimoto K (1988) Drugs Exptl. Clin. Res. XIV: 723
Kawakami M, Ikeda Y, Trang NL, Vine W, Cerami A (1984) In: Paton W (ed), Proceedings of IUPHAR, vol 2, MacMillan, London p 377
Cerami A, Ikeda Y, Trang NL, Hotez PJ, Beutler B (1985) Immunol. Lett. 11: 173.
Cput D, Beutler B, Hartog D, Brown-Scheimer S, Cerami A (1986) Proc. Natl. Acad. Sci. USA, 83: 1670
Carswell, Old LJ, Kassel RL, Green S, Fiore N, Williamson B (1975) Proc. Natl. Acad. Sci. USA, 72: 3666
Taguchi T (1986) Jpn. J. Cancer Chemoth. 13: 3491
Nilsson-Ehle P, Schotz MC (1976) J. Lipid Res. 17: 536
Uemura D, Yamamoto T, Yamada K, Okanishi M, Suzuki T, Naito K (1990) unpublished work
Patton JS, Shepard HM, Wilking H, Lewis G, Aggarwal BB, Eessalu TE, Gavin LA, Grunfeld C (1986) Proc. Natl. Acad. Sci. USA 83: 8313
Beutler BA, Cerami A (1985) J. Immunol. 135: 3969
Furue H (1984) Jpn. J. Cancer Chemoth. 11: 186
Ragelis EP (1984) in: Ragelis EP (ed) Seafood toxins, ACS Symposium Series No. 262, Am. Chem. Soc., Washington, D.C., p 25
Yasumota T, Raj U, Bagnis R (1984) In: Seafood poisonings in tropical regions, Toyota Foundation Reports, Tohoku University, Sendai, Japan
Scheuer PJ, Takahashi W, Tsutsumi J, Yoshida T (1967) Science 155: 1267
Nukina M, Tachibana K, Scheuer PJ (1986) In: Harris JB (ed) Natural toxins, Clarendon, Oxford p 46
Nukina M, Koyanagi LM, Scheuer PJ (1984) Toxicon 22: 169
Tachibana K (1980) Ph. D. Dissertation, University of Hawaii, Honolulu
Tachibana K, Nukina M, Joh Y-G, Scheuer PJ (1987) Biol. Bull. 172: 122
Murata M, Legrand AM, Ishibashi Y, Yasumoto T (1989) J. Am. Chem. Soc. 111: 8929
Murata M, Legrand AM, Ishibashi Y, Fukui M, Yasumoto T (1990) J. Am. Chem. Soc. 112: 4380
Ohizumi Y, Shibata S, Tachibana K (1981) J. Pharmacol. Exp. Ther. 217: 475
Ohizumi Y, Ishida Y, Shibata S (1982) J. Pharmacol. Exp. Ther. 221: 748
Tatsumi M, Kajiwara A, Yasumoto T, Ohizumi Y (1985) J. Pharmacol. Exp. Ther. 235: 783
Legrand AM, Bagnis R (1984) In: Ragelis EP (ed) Seafood toxins, ACS Symposium Series 262, Am. Chem. Soc. Washington D.C., p 217
Lewis RJ (1985) In: Anderson DM, White AW, Baden DG (eds) Toxic Dinoflagellates, Elsevier, New York, p 379
Bagnis R, Chanteau S, Chungue E, Hurtel JM, Yasumoto T, Inoue A (1980) Toxicon 18: 199
Nakajima I, Oshima Y, Yasumoto T (1981) Bull. Jpn. Soc. Sci. Fish. 47: 1029
Anderson DM, White AW, Baden DG (eds) (1986) Toxic dinoflagellates, Elsevier, New York
Adachi R, Fukuyo Y (1979) Bull. Jpn. Soc. Sci. Fish. 45: 67
Yasumoto T, Nakajima I, Bagnis R, Adachi R (1977) Bull. Jpn. Soc. Sci. Fish. 43: 1021
Yasumoto T, Inoue A, Bagnis R, Garçon M (1979) Bull. Jpn. Soc. Sci. Fish. 45: 395
Lin Y-Y, Risk M, Ray SM, Van Egen D, Clardy J, Golik J, James JC, Nakanishi K (1981) J. Am. Chem. Soc. 103: 6773
Shimizu Y, Chou H-N, Bando H, van Dyne G, Clardy J (1986) J. Am. Chem. Soc. 108: 514
Shimizu Y (1986) In: Harris JB (ed) Natural toxins, Clarendon, Oxford, p 115
Lee MS, Répéta DJ, Nakanishi K, Zagorski M (1986) J. Am. Chem. Soc. 108: 7855
Chou H-N, Shimizu Y (1987) J. Am. Chem. Soc. 109: 2184
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1991 Springer-Verlag Berlin Heidelberg
About this paper
Cite this paper
Uemura, D. (1991). Bioactive Polyethers. In: Scheuer, P.J. (eds) Bioorganic Marine Chemistry. Bioorganic Marine Chemistry, vol 4. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-76320-5_1
Download citation
DOI: https://doi.org/10.1007/978-3-642-76320-5_1
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-76322-9
Online ISBN: 978-3-642-76320-5
eBook Packages: Springer Book Archive