Chapter 4 Nitrogen-Containing Metabolites from Marine Bacteria

Alkaloids: Chemistry and Biology

Volumn 53, Issue C, 1999, Pages 239-285

  Gerwick, William H ^a   Sitachitta, Namthip ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77956655441     PISSN: 10994831     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1099-4831(08)60062-0     Document Type: Chapter

References (106)

1. Fenical W., and Jensen P. In: Attaway D.H., and Zaborsky O.R. (Eds). Marine Biotechnology: Pharmaceutical and Bioactive Natural Products 1 (1993), Plenum Press, New York 419-458
2. Fenical W. Chem. Rev. 93 (1993) 1673
3. Jensen P.R., and Fenical W. J. Ind. Micro. 17 (1996) 346
4. Davidson B.S. Curr. Opin. Biotech. 6 (1995) 284
5. Pietra F. Nat. Prod. Rep. 14 (1997) 453
6. Izumida H., Adachi K., Nishijima M., Endo M., and Miki W. J. Mar. Biotechnol. 2 (1995) 115
7. Izumida H., Adachi K., Mihara A., Yasuzawa T., and Sano H. J. Antibiot. 50 (1997) 916
8. Acebal C., Alcazar R., Canedo L.M., De La Calle F., Rodriguez P., Romero F., and Fernandez Puentes J.L. J. Antibiot. 51 (1998) 64
9. Wright A.E., Forleo D.A., Gunawardana G.P., Gunasekera S.P., Koehn F.E., and McConnell O.J. J. Org. Chem. 55 (1990) 4508
10. Rinehart K.L., Holt T.G., Fregeau N.L., Stroh J.G., Keifer P.A., Sun F., Li L.H., and Martin D.G. J. Org. Chem. 55 (1990) 4512
11. Powell R.G., Smith Jr. C.R., Weisleder D., Matsumotot G.K., Clardy J., and Kozlowski J. J. Am. Chem. Soc. 105 (1983) 3739
12. Gorst-Allman C.P., Steyn P.S., Vleggaar R., and Grobbelaar N. J. Chem. Soc., Perkin Trans. I 1311 (1984)
13. Stierle D.B., and Stierle A.A. Experientia 48 (1992) 1165
14. Shiozawa H., Kagasaki T., Kinoshita T., Haruyama H., Domon H., Utsui Y., Kodama K., and Takahashi S. J. Antibiot. 46 (1993) 1834
15. Shiozawa H., Kagasaki T., Torikata A., Tanaka N., Fujimoto K., Hata T., Furukawa Y., and Takahashi S. J. Antibiot. 48 (1995) 907
16. Shiozawa H., Shimada A., and Takahashi S. J. Antibiot. 50 (1997) 449
17. Shiozawa H., and Takahashi S. J. Antibio. 47 (1994) 851
18. Shigemori H., Bae M.A., Yazawa K., Sasaki T., and Kobayashi J. J. Org. Chem. 57 (1992) 4317
19. Ito S., and Hirata Y. Bull. Chem. Soc. Japan 50 (1977) 1813
20. Gunasekera S.P., Gunasekera M., and McCarthy P. J. Org. Chem. 56 (1991) 4830
21. Gil-Turnes M.S., Hay M.E., and Fenical W. Science 246 (1989) 116
22. Kameyama T., Takahashi A., Kurasawa S., Ishizuka M., Okami Y., Takeuchi T., and Umezawa H. J. Antibiot. 45 (1987) 1664
23. Takahashi A., Nakamura H., Kameyama T., Kurasawa S., Nagamawa H., Okami Y., Takeuchi T., Umezawa H., and Iitaka Y. J. Antibiot. 45 (1987) 1671
24. Bergeron R.J., and McManis J.S. Tetrahedron 45 (1989) 4939
25. Reid R.T., and Butler A. Limnol. Oceanogr. 36 (1991) 1783
26. Reid R.T., Live D.H., Faulkner D.J., and Butler A. Nature 366 (1993) 455
27. Deng J., Hamada Y., and Shioiri T. J. Am. Chem. Soc. 117 (1995) 7824
28. Rapoport H., and Holden K.G. J. Am. Chem. Soc. 84 (1962) 635
29. Williams R.P., and Hearn W.R. In: Gottlieb D., and Shaw P.D. (Eds). Antibiotics 2 (1967), Springer-Verlag, Berlin 410
30. Gerber N.N. Tetrahedron Lett. 24 (1983) 2797
31. Laatsch H., Thomson R.H., and Cox P.J. J. Chem. Soc., Perkin Trans. II 1331 (1984)
32. Ballantine J.A., Beer R.J.S., Crutchley D.J., Dodd G.M., and Palmer D.R. J. Chem. Soc. 2292 (1960)
33. Gauthier M.J. Can. J. Microbiol. 22 (1976) 138
34. Hoshino T., Kondo T., Uchiyama T., and Ogasawara N. Agric. Biol. Chem. 51 (1987) 965
35. Hoshino T., Takano T., Hori S., and Ogasawara N. Agric. Biol. Chem. 51 (1987) 2733
36. Hoshino T., and Ogasawara N. Agric. Biol. Chem. 54 (1990) 2339
37. Andersen R.J., Wolfe M.S., and Faulkner D.J. Mar. Biol. 27 (1974) 281
38. Burkholder P.R., Pfister R.M., and Leitz F.H. Appl. Microbiol. 14 (1966) 649
39. Yoshikawa K., Takadera T., Adachi K., Nishijima M., and Sano H. J. Antibio. 50 (1997) 949
40. Kobayashi J., Mikami S., Shigemori H., Takao T., Shimonishi Y., Izuta S., and Yoshida S. Tetrahedron 51 (1995) 10487
41. Oclarit J.M., Ohta S., Kamimura K., Yamaoka Y., and Ikegami S. Fish. Sci. 60 (1994) 559
42. Lovell F.M. J. Am. Chem. Soc. 88 (1966) 4510
43. Hanessian S., and Kaltenbronn J.S. J. Am. Chem. Soc. 88 (1966) 4509
44. Laatsch H., and Pudleiner H. Liebigs Ann. Chem. 863 (1989)
45. Hanefeld U., Floss H.G., and Laatsch H. J. Org. Chem. 59 (1994) 3604
46. Wratten S.J., Wolfe M.S., Andersen R.J., and Faulkner D.J. Antimicrob. Agts. Chemother. 11 (1977) 411
47. Wells I.C. J. Biol. Chem. 196 (1952) 331
48. Jayatilake G.S., Thornton M.P., Leonard A.C., Grimwade J.E., and Baker B.J. J. Nat. Prod. 59 (1996) 293
49. Gandhi N.M., Nazreth J., Divekar P.V., Kohl H., and De Souza N.J. J. Antibio. 26 (1973) 797
50. Kohl H., Bhat S.V., Patell J.R., Gandhi N.M., Nazareth J., Divekar P.V., De Souza N.J., Berscheid H.G., and Fehlhaber H.W. Tetrahedron Lett. 983 (1974)
51. Imamura N., Adachi K., and Sano H. J. Antibiotics 47 (1994) 257
52. Yasumoto T., Yasumura D., Yotsu M., Michishita T., Endo A., and Kotaki Y. Agric. Biol. Chem. 50 (1986) 793
53. Yotsu M., Yamazaki T., Meguro Y., Endo A., Murata M., Naoki H., and Yasumoto T. Toxicon 25 (1987) 225
54. Izumida H., Imamura N., and Sano H. J. Antibio. 49 (1996) 76
55. Needham J., Kelly M.T., Ishige M., and Andersen R.J. J. Org. Chem. 59 (1994) 2058
56. Oclarit J., Okada H., Ohta S., Kaminura K., Yamaoka Y., Lizuka T., Miyashiro S., and Ikegami S. Microbios 78 (1994) 7
57. Gerard J., Lloyd R., Barsby T., Haden P., Kelly M.T., and Andersen R.J. J. Nat. Prod. 60 (1997) 223
58. Kobayashi M., Aoki S., Gato K., Matsunami K., Kurosu M., and Kitagawa I. Chem. Pharm. Bull. 42 (1994) 1587
59. Noguchi T., Jeon J.K., Arakawa O., Sugita H., Deguchi Y., Shida Y., and Hashimoto K. J. Biochem. 99 (1986) 311
60. Noguchi T., Hwang D.F., Arakawa O., Sugita H., Deguchi Y., Shida Y., and Hashimoto K. Marine Biology 94 (1987) 625
61. Narita H., Matsubara S., Miwa N., Akahane S., Murakami M., Goto T., Nara M., Noguchi T., Saito T., Shida Y., and Hashimoto K. Nippon Suisan Gakkaishi 53 (1987) 617
62. Hwang D.F., Arakawa O., Saito T., Noguchi T., Tsukamoto K., Shida Y., and Hashimoto K. Marine Biology 100 (1989) 327
63. Hwang D.F., Cheng C.A., Chen H.C., Jeng S.S., Noguchi T., Ohwada K., and Hashimoto K. Fish. Sci. 60 (1994) 567
64. Bell R., Carmeli S., and Sar N. J. Nat. Prod. 57 (1994) 1587
65. Jalal M.A.F., Hossain M.B., van der Helm D., Sanders-Loehr J., Actis L.A., and Crosa J.H. J. Am. Chem. Soc. 111 (1989) 292
66. Crosa J.H. Nature 283 (1980) 566
67. Actis L.A., Fish W., Crosa J.H., Kellerman K., Ellenberger S.R., Hauser F.M., and Sanders-Loehr J. J. Bacteriol. 167 (1986) 57
68. Stierle A.C., Cardellina II J.H., and Singleton F.L. Experientia 44 (1988) 1021
69. Schmitz F.J., Vanderah D.J., Hollenbeak K.H., Enwall C.E.L., Gopichand Y., Sengupta P.K., Hossain M.B., and van der Helm C. J. Org. Chem. 48 (1983) 3941
70. Stierle A.A., Cardellina II J.H., and Singleton F.L. Tetrahedron Lett. 32 (1991) 4847
71. Fusetani N., Ejima D., Matsunaga S., Hashimoto K., Itagaki K., Akagi Y., Taga N., and Suzuki K. Experientia 43 (1987) 464
72. Wang S., Kuramoto M.G.Y., Yamada K., Yazawa K., and Uemura D. Chem. Lett. 791 (1995)
73. Gerard J., Haden P., Kelly M.T., and Andersen R.J. Tetrahedron Lett. 37 (1996) 7201
74. Peypoux F., Pommier M.T., Marion D., Ptak M., Das B.C., and Michel G. J. Antibiot. 39 (1986) 636
75. Trischman J.A., Jensen P.R., and Fenical W. Tetrahedron Lett. 35 (1995) 5571
76. Kalinovskaya N.I., Kuznetsova T.A., Rashkes Y.V., Mil'grom Y.M., Mil'grom E.G., Willis R.H., Wood A.I., Kurtz H.A., Carabedian C., Murphy P., and Elyakov G.B. Russ. Chem. Bull. 44 (1995) 951
77. Naruse N., Tenmyo O., Kobaru S., Kamei H., Miyaki T., Konishi M., and Oki T. J. Antibiot. 43 (1990) 267
78. Harrigan G.G., Harrigan B.L., and Davidson B.S. Tetrahedron 53 (1997) 1577
79. Canedo L.M., Fernandez J.L., Perez Faz J., Acebal C., de la Calle F., Garcia Fravalos D., and Garcia de Quesada T. J. Antibiot. 50 (1997) 175
80. Imamura N., Nishijima M., Takadera T., Adachi K., Sakai M., and Sano H. J. Antibiot. 50 (1997) 8
81. Imamura N., Nishijima M., Adachi K., and Sano H. J. Antibiot. 46 (1993) 241
82. Abidi S.L., and Adams B.R. Magn. Reson. Chem. 25 (1987) 1078
83. Biabami M.A.F., Baake M., Lovisetto B., Laatsch H., Helmke E., and Weyland H. J. Antibiot. 51 (1998) 333
84. Davidson B.S., and Shumacher R.W. Tetrahedron 49 (1993) 6569
85. Adamczeski M., Quinoa E., and Crews P. J. Am. Chem. Soc. 111 (1989) 647
86. Jiang Z.D., Jensen P.R., and Fenical W. Tetrahedron Lett. 38 (1997) 5065
87. Bernan V.S., Montenegro D.A., Korshalla J.D., Maiese W.M., Steinberg D.A., and Greenstein M. J. Antibiot. 47 (1994) 1417
88. Zaccardi J., Alluri M., Ashcroft J., Bernan V., Korshalla J.D., Morton G.O., Siegel M., Tsao R., Williams D.R., Maiese W., and Ellestad G.A. J. Org. Chem. 59 (1994) 4045
89. Palaniswamy V.A., and Gould S.J. J. Am. Chem. Soc. 108 (1986) 5651
90. Zmijewski Jr. M.J. J. Antibiot. 38 (1985) 819
91. Williams R.M., and Herberich B. J. Am. Chem. Soc. 120 (1998) 10272
92. Pathirana C., Jensen P.R., Dwight R., and Fenical W. J. Org. Chem. 57 (1992) 740
93. Pusecker K., Laatsch H., Helmke E., and Weyland H. J. Antibiot. 50 (1997) 479
94. Takahashi A., Kurasawa S., Ikeda D., Okami Y., and Takeuchi T. J. Antibiot. 42 (1989) 1556
95. Takahashi A., Ikeda D., Nakamura H., Naganawa H., Kurasawa S., Okami Y., Takeuchi T., and Iitaka Y. J. Antibiot. 42 (1989) 1562
96. Trischman J.A., Tapiolas D.M., Jensen P.R., Dwight R., Fenical W.H., McKee T.C., Ireland C.M., Stout T.J., and Clardy J. J. Am. Chem. Soc. 116 (1994) 757
97. Miao S., Anstee M.R., LaMarco K., Matthew J., Huang L.H.T., and Brasseur M.M. J. Nat. Prod. 60 (1997) 858
98. Moore B.S., and Seng D. Tetrahedron Lett. 39 (1998) 3915
99. Bae M.A., Yamada K., Ijuin Y., Tsuji T., Yazawa K., Tomono Y., and Uemura D. Heterocyclic Commun. 2 (1996) 315
100. Takahashi C., Takada T., Yamada T., Minoura K., Uchida K., Matsumura E., and Numata A. Tetrahedron Lett. 35 (1994) 5013
101. Batrakov S.G., Nikitin D.I., and Pitryuk I.A. Biochim. Biophys. Acta 1302 (1996) 167
102. Morishita T., Sato A., Hisamoto M., Oda T., Matsuda K., Ishii A., and Kodama K. J. Antibiot. 50 (1997) 457
103. Kosuge T., Tsuji K., and Hirai K. Chem. Pharm. Bull. 30 (1982) 3255
104. Kosuge T., Tsuji K., Hirai K., and Fukuyama T. Chem. Pharm. Bull. 33 (1985) 3059
105. Bewley C.A., Holland N.D., and Faulkner D.J. Experientia 52 (1996) 716
106. Schmidt E.W., Bewley C.A., and Faulkner D.J. J. Org. Chem. 63 (1998) 1254