Amphidinolides, bioactive macrolides from symbiotic marine dinoflagellates

Natural Product Reports

Volumn 21, Issue 1, 2004, Pages 77-93

  Kobayashi, Jun'ichi ^a,b,c,d   Tsuda, Masashi ^a,b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b Hokkaido University ^*

^c MITSUBISHI KASEI INST OF LIFE SCI   (Japan)

^d UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL FACTOR; FUSED HETEROCYCLIC RINGS; LACTONE; MACROLIDE;

ANIMAL; BIOLOGY; CHEMICAL STRUCTURE; CHEMISTRY; DINOFLAGELLATE; ISOLATION AND PURIFICATION; REVIEW;

ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; BIOLOGICAL FACTORS; DINOFLAGELLIDA; LACTONES; MACROLIDES; MARINE BIOLOGY; MOLECULAR STRUCTURE;

AMPHIDINIUM; ANIMALIA; DINOPHYCEAE; PLATYHELMINTHES;

EID: 1342311401     PISSN: 02650568     EISSN: None     Source Type: Journal    
DOI: 10.1039/b310427n     Document Type: Review

References (88)

1. J. Kobayashi and M. Ishibashi, Chem. Rev., 1993, 93, 1753.
2. M. Ishibashi and J. Kobayashi, Heterocycles, 1997, 44, 543.
3. J. Kobayashi, M. Ishibashi, in Comprehensive Natural Products Chemistry, Vol. 8. Miscellaneous Natural Products Including Marine Products, Pheromones, Plant Hormones, and Aspects of Ecology, ed. K. Mori, Elsevier Science, Oxford, 1999, pp. 415-650.
4. J. Kobayashi, M. Tsuda and M. Ishibashi, Pure Appl. Chem., 1999, 71, 1123.
5. J. Kobayashi, K. Shimbo, T. Kubota and M. Tsuda, Pure Appl. Chem., 2003, 75, 337.
6. T. K. Chakraborty and S. Das, Curr. Med. Chem., Anti-cancer Agents, 2001, 1, 131.
7. Y. Shimizu, Curr. Opin. Microbiol., 2003, 6, 236.
8. A. H. Daranas, M. Norte and J. J. Fernández, Toxicon, 2001, 31, 1101.
9. B. S. Moore, Nat. Prod. Rep., 1999, 16, 653.
10. K. S. Rein and J. Borrone, Comp. Biotechnol. Physiol., B: Biochem. Mol. Biol., 1999, 124, 117.
11. T. Yasumoto and M. Satake, Chimia, 1998, 52, 63.
12. T. Yasumoto and M. Satake, J. Toxicol., Toxin Rev., 1996, 15, 91.
13. J. Kobayashi, M. Ishibashi, H. Nakamura, Y. Hirata, T. Yamasu, T. Sasaki and Y. Ohizumi, Experientia, 1988, 44, 800.
14. J. Kobayashi, M. Ishibashi, H. Nakamura, Y. Hirata, T. Ohizumi and Y. Ohizumi, J. Chem. Soc., Perkin Trans. 1, 1989, 101-103.
15. T. Yamasu and A. Okazaki, Galaxea, 1987, 6, 61.
16. L. Provasoli, in Culture and Collection of Algae, ed. A. Watanabe and A. Hattori, Japanese Society of Plant Physiology, Tokyo, 1968, pp. 63-75.
17. H. Iwasaki, in Sourui Kenkyuhou, ed. K. Nishizawa and M. Chihara, Kyouritsu-Shuppan, Tokyo, 1979, pp. 281-293.
18. J. Kobayashi, M. Ishibashi, H. Nakamura, Y. Ohizumi, T. Yamasu, T. Sasaki and Y. Hirata, Tetrahedron Lett., 1986, 27, 5755.
19. M. Ishibashi, Y. Ohizumi, M. Hamashima, H. Nakamura, Y. Hirata, T. Sasaki and J. Kobayashi, J. Chem. Soc., Chem. Commun., 1987, 1127.
20. J. Kobayashi, M. Ishibashi, H. Nakamura, Y. Ohizumi, T. Yamasu, Y. Hirata, T. Sasaki, T. Ohta and S. Nozoe, J. Nat. Prod., 1989, 52, 1036.
21. J. Kobayashi, M. Ishibashi, M. R. Walchli, H. Nakamura, Y. Hirata, T. Sasaki and Y. Ohizumi, J. Am. Chem. Soc., 1988, 110, 490.
22. J. Kobayashi, M. Ishibashi, T. Murayama, M. Takamatsu, M. Iwamura, Y. Ohizumi and T. Sasaki, J. Org. Chem., 1990, 55, 3421.
23. J. Kobayashi, M. Sato and M. Ishibashi, J. Org. Chem., 1993, 58, 2645.
24. M. Ishibashi, M. Sato and J. Kobayashi, J. Org. Chem., 1993, 58, 6928.
25. J. Kobayashi, N. Yamaguchi and M. Ishibashi, J. Org. Chem., 1994, 59, 4698.
26. M. Ishibashi, N. Yamaguchi, T. Sasaki and J. Kobayashi, J. Chem. Soc., Chem. Commun., 1994, 1445.
27. M. Ishibashi, M. Takahashi and J. Kobayashi, J. Org. Chem., 1995, 60, 6062.
28. J. Kobayashi, M. Takahashi and M. Ishibashi, Tetrahedron Lett., 1996, 37, 1449.
29. M. Ishibashi, M. Takahashi and J. Kobayashi, Tetrahedron, 1997, 53, 7827.
30. T. Kubota, M. Tsuda and J. Kobayashi, Tetrahedron Lett., 2000, 41, 713.
31. J. Kobayashi, N. Yamaguchi and M. Ishibashi, Tetrahedron Lett., 1994, 35, 7049.
32. J. Kobayashi, H. Shigemori, M. Ishibashi, T. Yamasu, H. Hirota and T. Sasaki, J. Org. Chem., 1991, 56, 5221.
33. M. Tsuda, T. Sasaki and J. Kobayashi, J. Org. Chem., 1994, 59, 3734.
34. J. Kobayashi, M. Tsuda, M. Ishibashi, H. Shigemori, T. Yamasu, H. Hirota and T. Sasaki, J. Antibiot., 1991, 44, 1259.
35. M. Tsuda, T. Endo and J. Kobayashi, J. Org. Chem., 2000, 65, 1349.
36. J. Kobayashi, T. Kubota, T. Endo and M. Tsuda, J. Org. Chem., 2001, 66, 134.
37. T. Kubota, T. Endo, M. Tsuda, M. Shiro and J. Kobayashi, Tetrahedron, 2001, 57, 6175.
38. M. Tsuda. T. Endo and J. Kobayashi, Tetrahedron, 1999, 55, 14565.
39. J. Kobayashi, J. K. Simbo, K. Sato and M. Tsuda, J. Org. Chem., 2002, 67, 6585.
40. K. Shimbo, M. Tsuda, N. Izui and J. Kobayashi, J. Org. Chem., 2002, 67, 1020.
41. M. Tsuda, N. Izui, K. Shimbo, M. Sato, E. Fukushi, J. Kawabata, K. Katsumata, T. Horiguchi and J. Kobayashi, J. Org. Chem., 2003, 68, 5339.
42. M. Tsuda, N. Izui, K. Shimbo, M. Sato, E. Fukushi, J. Kawabata and J. Kobayashi, J. Org. Chem., 2003, 68, 9109.
43. J. Kobayashi, M. Ishibashi and H. Hirota, J. Nat. Prod., 1991, 54, 1435.
44. H. W. Lam and G. Pattenden, Angew. Chem., Int. Ed., 2002, 41, 508.
45. R. E. Maleczka, Jr., L. R. Terrell, F. Geng and J. S. Ward, III, Org. Chem., 2002, 4, 2841.
46. B. M. Trost, J. D. Chisholm, S. T. Wrobleski and M. Jung, J. Am. Chem. Soc., 2002, 124, 12421.
47. K. Matsunaga, K. Nakatani, M. Ishibashi, J. Kobayashi and Y. Ohizumi, Biochim. Biophys. Acta, 1999, 1427, 24.
48. I. Bauer, L. Maranda, Y. Shimizu, R. W. Peterson and L. Cornell, J. Am. Chem. Soc., 1994, 116, 2657.
49. L. Maranda and Y. Shimizu, J. Phycol., 1996, 32, 873.
50. M. Ishibashi, H. Ishiyama and J. Kobayashi, Tetrahedron Lett., 1994, 35, 8241.
51. J. Kobayashi, K. Shimbo, M. Sato, M. Shiro and M. Tsuda, Org. Lett., 2000, 2, 2805.
52. H. Ishiyama, T. Takemura, M. Tsuda and J. Kobayashi, Tetrahedron, 1999, 55, 4583.
53. H. Ishiyama, T. Takemura, M. Tsuda and J. Kobayashi, J. Chem. Soc., Perkin Trans 1, 1999, 1163.
54. H. Ishiyama, Ph.D. thesis, 2000, Hokkaido University, Sapporo.
55. M. B. Cid and G. Pattenden, Tetrahedron Lett., 2000, 41, 7373.
56. K. Ohi, K. Shima, K. Hamada and S. Nishiyama, in Symposium Papers of 41st Symposium on The Chemistry of Natural Products, in Nagoya, Minoru Isobe, Nagoya, 1999, pp. 31-36.
57. T. Kubota, M. Tsuda and J. Kobayashi, Org. Lett., 2001, 3, 1363.
58. H. Ishiyama, M. Ishibashi and J. Kobayashi, Chem. Pharm. Bull., 1996, 44, 1819.
59. N. Matsumori, D. Kaneno, M. Murata, H. Nakamura and K. Tachibana, J. Org. Chem., 1999, 64, 866.
60. I. Ohtani, T. Kusumi, Y. Kashman and H. Kakisawa, J. Am. Chem. Soc., 1991, 113, 4092.
61. T. Kubota, M. Tsuda and J. Kobayashi, J. Org. Chem., 2002, 67, 1651.
62. D. R. Williams and W. S. Kissel, J. Am. Chem. Soc., 1998, 120, 11198.
63. D. R. Williams and K. G. Meyer, J. Am. Chem. Soc., 2001, 123, 765.
64. I. Bauer, L. Maranda, K. A. Young, Y. Shimizu, C. Fairchild, L. Cornell, J. MacBeth and S. Huang, J. Org. Chem., 1995, 60, 1084.
65. D. R. Williams, K. G. Meyer and L. Mi, Org. Lett., 2000, 2, 945.
66. A. Fürstner, C. Aïssa, R. Riveiros and J. Ragot, Angew. Chem., Int. Ed., 2002, 41, 4763.
67. A. K. Ghosh and C. Liu, J. Am. Chem. Soc., 2003, 125, 2374.
68. J. Kobayashi, M. Takahashi and M. Ishibashi, J. Chem. Soc., Chem. Commun., 1995, 1639.
69. M. Tsuda, T. Kubota, Y. Sakuma and J. Kobayashi, Chem. Pharm. Bull., 2001, 49, 1366.
70. T. Kubota, M. Tsuda and J. Kobayashi, Tetrahedron, 2001, 57, 5975.
71. M. Sato, K. Shimbo, M. Tsuda and J. Kobayashi, Tetrahedron Lett., 2000, 41, 503.
72. M. Tsuda, N. Izui, M. Sato and J. Kobayashi, Chem. Pharm. Bull., 2002, 50, 976.
73. Y. Doi, M. Ishibashi, H. Nakamichi, T. Kosaka, T. Ishikawa and J. Kobayashi, J. Org. Chem., 1997, 62, 3820.
74. T. Kubota, M. Tsuda, Y. Doi, A. Takahashi, H. Nakamichi, M. Ishibashi, E. Fukushi, J. Kawabata and J. Kobayashi, Tetrahedron, 1998, 54, 14455.
75. M. Satake, M. Murata, T. Yasumoto, T. Fujita and H. Naoki, J. Am. Chem. Soc., 1991, 113, 9859.
76. G. K. Paul, N. Matusmori, M. Murata and K. Tachibana, Tetrahedron Lett., 1995, 36, 6279.
77. G. K. Paul, N. Matusmori, K. Konoki, M. Sasaki, M. Murata and K. Tachibana, in Harmful and Toxic Algal Blooms, ed. T. Yasumoto, Y. Oshima and Y. Fukuyo, UNESCO, Paris, 1996, pp. 503-506.
78. G. K. Paul, N. Matusmori, K. Konoki, M. Murata and K. Tachibana, J. Mar. Biotechnol., 1997, 5, 124.
79. M. Murata, S. Matsuoka, N. Matsumori, G. K. Paul and K. Tachibana, J. Am. Chem. Soc., 1999, 121, 870.
80. T. Houdai, S. Matsuoka, M. Murata, M. Satake, S. Ota, Y. Oshima and L. L. Rhodes, Tetrahedron, 2001, 57, 5551.
81. J. Kobayashi, T. Kubota, M. Takahashi, M. Ishibashi, M. Tsuda and H. Naoki, J. Org. Chem., 1999, 64, 1478.
82. T. Kubota, M. Tsuda, M. Takahashi, M. Ishibashi, N. Naoki and J. Kobayashi, J. Chem. Soc., Perkin Trans. 1, 1999, 3483.
83. T. Kubota, M. Tsuda, M. Takahashi, M. Ishibashi, S. Oka and J. Kobayashi, Chem. Pharm. Bull., 2000, 48, 1447.
84. R. K. Trench and H. Winsor, Symbiosis, 1987, 3, 1.
85. R. V. Snyder, P. D. L. Gibbs, A. Palacios, L. Abiy, R. Dickey, J. V. Lopez and K. S. Rein, Mar. Biotechnol., 2003, 5, 1.
86. T. Yasumoto, Y. Ohshima, W. Sugawara, Y. Fukuyo, H. Oguri, T. Igarashi and N. Fujita, Bull. Jpn. Soc. Sci. Fish., 1980, 46, 1397.
87. Y. Y. Lin, M. Risk, S. M. Ray, D. Van Engen, J. Clardy, J. Golik, J. C. James and K. Nakanishi, J. Am. Chem. Soc., 1981, 103, 6773.
88. T. Horiguchi, Phycol. Res., 1995, 43, 129.