The isoxazole alkaloids

Alkaloids: Chemistry and Biology

Volumn 57, Issue C, 2001, Pages 185-233

  Rahbœk, Lisa ^a   Christophersen, Carsten ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ISOXAZOLE DERIVATIVE;

AGARICALES; ANIMAL; BACTERIUM; CHEMISTRY; METABOLISM; PLANT; REVIEW; SPONGE (PORIFERA);

AGARICALES; ALKALOIDS; ANIMALS; BACTERIA; ISOXAZOLES; PLANTS; PORIFERA;

EID: 0035231836     PISSN: 10994831     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0099-9598(01)57004-2     Document Type: Review

References (190)

1. Kochetkov N.K., and Sokolov S.D. In: Katritzky A.R. (Ed). Advances in Heterocyclic Chemistry Vol. 2 (1963), Academic Press, New York 365
2. Lewis J.R. Nat. Prod. Rep. 1 (1984) 387
3. Lewis J.R. Nat. Prod. Rep. 5 (1988) 351
4. Lewis J.R. Nat. Prod. Rep. 6 (1989) 503
5. Lewis J.R. Nat. Prod. Rep. 9 9 (1992) 81
6. Lewis J.R. Nat. Prod. Rep. 11 (1994) 395
7. Lewis J.R. Nat. Prod. Rep. 12 (1995) 135
8. Lewis J.R. Nat. Prod. Rep. 13 (1996) 435
9. Lewis J.R. Nat. Prod. Rep. 15 (1998) 371
10. Lewis J.R. Nat. Prod. Rep. 15 (1998) 417
11. Lewis J.R. Nat. Prod. Rep. 16 (1999) 389
12. Lewis J.R. Nat. Prod. Rep. 17 (2000) 57
13. Lewis J.R. Nat. Prod. Rep. 18 (2001) 95
14. Faulkner D.J. Nat. Prod. Rep. 1 (1984) 551
15. Faulkner D.J. Nat. Prod. Rep. 3 (1986) 1
16. Faulkner D.J. Nat. Prod. Rep. 4 (1987) 539
17. Faulkner D.J. Nat. Prod. Rep. 8 (1991) 97
18. Faulkner D.J. Nat. Prod. Rep. 9 (1992) 323
19. Faulkner D.J. Nat. Prod. Rep. 10 (1993) 497
20. Faulkner D.J. Nat. Prod. Rep. 11 (1994) 355
21. Faulkner D.J. Nat. Prod. Rep. 12 (1995) 223
22. Faulkner D.J. Nat. Prod. Rep. 13 (1996) 75
23. Faulkner D.J. Nat. Prod. Rep. 14 (1997) 259
24. Faulkner D.J. Nat. Prod. Rep. 15 (1998) 113
25. Faulkner D.J. Nat. Prod. Rep. 16 (1999) 155
26. Faulkner D.J. Nat. Prod. Rep. 17 (2000) 7
27. Faulkner D.J. Nat. Prod. Rep. 18 (2001) 1
28. Christophersen C. In: Brossi A. (Ed). The Alkaloids Vol. 24 (1985), Academic Press, Orlando 25
29. Kobayashi J., and Ishibashi M. In: Brossi A., and Cordell G.A. (Eds). The Alkaloids Vol. 41 (1992), Academic Press, San Diego 42-124
30. Fenical W. In: Pelletier S.W. (Ed). Alkkaloids,: Chemical and Biological Perspectives Vol. 4 (1986), John Wiley & Sons, Inc, New York 275
31. Antkowiak R., and Antkowiak W.Z. In: Brossi A. (Ed). The Alkaloids Vol. 40 (1991), Academic Press, San Diego 189-340
32. R. P. Buhs, I. Putter, R. Ormond, J. E. Lyons, L. Chaiet, F. A. Kuehl Jr, F. J. Wofl, N.R. Trenner, R. L. Peck, E. Howe, B. E. Hunnewell, G. Downing, E. Newstead, and K. Folkers, J. Am. Chem. Soc. 77, 234.
33. Hidy P.H., Hodge E.B., Young V.V., Harried R.L., Brewer G.A., Phillips W.F., Runge W.F., Stavely H.E., Pohland A., Boaz H., and Sullivan H.R. J. Am. Chem. Soc. 77 (1955) 2345
34. Hatfield G.M. In: Kinghorn A.D. (Ed). Toxic Plants (1979), Columbia University Press, New York 7
35. Stammer C.H., Wilson A.N., Holly F.W., and Folkers K. J. Am. Chem. Soc. 77 (1955) 2346
36. Miller J.L., Neuhaus F.C., Lassen F.O., and Stammer C.H. J. Org. Chem. 33 (1968) 3908
37. Lassen F.O., and Stammer C.H. J. Org. Chem. 35 (1971) 2631
38. Sammes P.G. In: Herz W., Grisebach H., and Kirby G.W. (Eds). Progress in the Chemistry of Organic Natural Products Vol. 32 (1975), Springer-Verlag, Wien 51
39. McCullough W.G., and Merkal R.S. J. Bacteriol. 137 (1979) 243
40. Martin D.G., Duchamp D.J., and Chidester C.G. Tetrahedron Lett. (1973) 2549
41. Haka L.J., Martin D.G., and Neil G.L. Cancer Chemother. Rep., Part 1 57 (1973) 141
42. Houchens D.P., Ovejera A.A., Sheridan M.A., Johnson R.K., Bogden A.E., and Neil G.L. Cancer Treat. Rep. 63 (1979) 473
43. Ha_ka L.J., and Dietz A. Antimicrob. Agents Chemother. 3 (1973) 425
44. Ha_ka L.J., Gerpheide S.A., Spieles P.R., Martin D.G., Belter P.A., Coleman T.A., and Meyer H.F. Antimicrob. Agents Chemother. 7 (1975) 807
45. Mzengeza S., Yang C.M., and Whitney R.A. J. Am. Chem. Soc. 109 (1987) 276
46. Griesbeck A.G., Hirt J., Peters K., Peters E.-M., and von Schnering H.-G. Liebigs Ann. (1995) 619
47. Ahluwalia G.S., Grem J.L., Hao Z., and Cooney D.A. Pharmacol. Ther. 46 (1990) 243
48. Martin D.G., Chidester C.G., Mizsak S.A., Duchamp D.J., Baczynskyj L., Krueger W.C., Wnuk R.J., and Meulman P.A. J. Antibiot. 28 (1975) 91
49. Martin D.G., Hanka L.J., and Neil G.L. Cancer Chemother. Rep., Part 1 58 (1974) 935
50. Cooney D.A., Jayaram H.N., Ryan J.A., and Bono V.H. Cancer Chemother. Rep., Part 1 58 (1974) 793
51. Gould S.J., and Ju S. J. Am. Chem. Soc. 111 (1989) 2329
52. Gould S.J., and Ju S. J. Am. Chem. Soc. 114 (1992) 10166
53. Kobinata K., Sekido S., Uramoto M., Ubukata M., Osada H., Yamaguchi I., and Isono K. Agric. Biol. Chem. 55 (1991) 1415
54. Harada S., Tsubotani S., Hida T., Ono H., and Okazaki H. Tetrahedron Letters 27 (1986) 6229
55. Harada S., Tsubotani S., Hida T., Koyama K., Kondo M., and Ono H. Tetrahedron 44 (1988) 6589
56. Nozaki Y., Katayama N., Ono H., Tsubotani S., Harada S., Okazaki H., and Nakao Y. Nature 325 (1987) 179
57. Tamura N., Matsushita Y., Kawano Y., and Yoshioka K. Chem. Pharm. Bull. 38 (1990) 116
58. Nozaki Y., Katayama N., Harada S., Ono H., and Okazaki H. J. Antibiot. 42 (1989) 84
59. Natsugari H., Kawano Y., Morimoto A., Yoshioka K., and Ochiai M. J. Chem. Soc., Chem. Commun. (1987) 62
60. Nakao Y. Spec. Publ.- Royal Soc. Chem. (1989) 119
61. Anthoni U., Christophersen C., Nielsen P.H., Gram L., and Petersen B.O. J. Nat. Prod. 58 (1995) 1786
62. Hamada M., Kondo S., Nakamura H., Ikeda T., Ikeda D., Iinuma K., Gomi S., Ikeda Y., Takeuchi T., Umezawa H., and Iitaka Y. J. Antibiot. 36 (1983) 445
63. Imai H., Suzuki K.-I., Miyazaki S., Tanaka K., Watanabe S., and Iwanami M. J. Antibiot. 36 (1983) 911
64. Tsubotani S., Funabashi Y., Takamoto M., Hakoda S., and Harada S. Tetrahedron 47 (1991) 8079
65. Hakoda S., Tsubotani S., Iwasa T., Suzuki M., Kondo M., and Harada S. J. Antibiot. 45 (1992) 854
66. Iwama T., Nagai Y., Tamura N., Harada S., and Nagaoka A. Eur. J. Pharamcol. 197 (1991) 187
67. Tamura N., Iwama T., and Itch K. Chem. Pharm. Bull. 40 (1992) 381
68. Ikegami F., Kamiya M., Kuo Y.-H., Lambein F., and Murakoshi I. Biol. Pharm. Bull. 19 (1996) 1214
69. Krogsgaard-Larsen P., Brehm L., and Schaumburg K. Acta Chem. Scand. B35 (1981) 311
70. Konda Y., Takahashi H., and Onda M. Chem. Pharm. Bull. 33 (1985) 1083
71. Chilton W.S., and Ott J. Lloydia 39 (1976) 150
72. Benjamin D.R. Mushrooms: poisons and panaceas: a handbook for naturalists, mycologists, and physicians (1995), W. H. Freeman and Company 1-422 New York
73. Krogsgaard-Larsen P., and Christensen S.B. Acta Chem. Scand. B30 (1976) 281
74. Frolund B., Tagmose L., Liljefors T., Stensbøl T.B., Engblom C., Kristiansen U., and Krogsgaard-Larsen P. J. Med. Chem. 43 (2000) 4930
75. De Amici M., De Micheli C., and Misani V. Tetrahedron 46 (1990) 1975
76. Takemoto T., and Nakajima T. Yakugaku Zasshi 84 (1964) 1183
77. Takemoto T., and Nakamiya T. Yakugaku Zasshi 84 (1964) 1230
78. Iwasaki H., Kamiya T., Oka O., and Ueyanagi J. Chem. Pharm. Bull. 13 (1965) 753
79. Kamiya T. Chem Pharm. Bull. 14 (1966) 1307
80. Wagner I., and Musso H. Angew. Chem. Int. Ed. Engl. 22 (1983) 816
81. Wagner I., and Musso H. Angew. Chem. 95 (1983) 827
82. Döpp H., and Musso H. Chem. Ber. 106 (1973) 3473
83. Döpp H., Maurer S., Sasaki A.N., and Musso H. Liebigs Ann. Chem. 254 (1982)
84. Kuo Y.-H., Lambein F., Mellor L.C., Adlington R.M., and Baldwin J.E. Phytochemistry 37 (1994) 713
85. Lambein F., Kuo Y.-H., and Parijs R.V. Heterocycles 4 (1976) 567
86. De Bruyn A., Verhegge G., and Lambein F. Magn. Res. Chem. 29 (1991) 641
87. Lambein F., and Van Parijs R. Biochem. Biophys. Res. Commun. 32 (1968) 474
88. Kuo Y.-H., and Lambein F. Phytochemistry 30 (1991) 3241
89. Lambein F., Ongena G., and Kuo Y.-H. Phytochemistry 29 (1990) 3793
90. Kuo Y.-H., Khan J.K., and Lambein F. Phytochemistry 35 (1994) 911
91. Lambein F., Schamp N., Vandendriessche L., and Van Parijs R. Biochem. Biophys. Res. Commun. 37 (1969) 375
92. Ikegami F., De Blauwe M., and Lambein F. Arch. Int. Physiol. Biochim. 89 (1981) B174
93. Schenk S.U., and Werner D. Phytochemistry 30 (1991) 467
94. Lambein F., and De Vos B. Arch. Int. Physiol. Biochim. 89 (1981) B66
95. Van Rompuy L., Lambein F., De Gussem R., and Van Parijs R. Biochem. Biophys. Res. Commun. 56 (1974) 199
96. Pasteels J.M., Braekman J.C., and Daloze D. Tetrahedron 38 (1982) 1891
97. Van Rompuy L., Lambein F., Van Parijs R., and Ressler C. Experientia 30 (1974) 1379
98. Ikegami F., Tajima Y., Ohmiya S., Lambein F., and Murakoshi I. Chem. Pharm. Bull. 32 (1984) 2450
99. Lambein F., and Van Parijs R. Biochem. Biophys. Res. Commun. 61 (1974) 155
100. Kuo Y.-H., Lambein F., and Van Parijs R. Arch. Int. Physiol. Biochim. 40 (1970) 557
101. Lambien F., Khan J.K., Becu C., and Bruyn A.D. Phytochemistry 31 (1992) 887
102. Lambein F., and Van Parijs R. Biochem. Biophys. Res. Commun. 40 (1970) 557
103. Murakoshi I., Ikegami F., Kato F., Haginiwa J., Lambein F., Van Rompuy L., and Van Parijs R. Phytochemistry 14 (1975) 1515
104. Kuo Y.-H., Lambein F., and Van Parijs R. Arch. Int. Physiol. Biochim. 84 (1976) 169
105. Kusumi T., Chang C.C., Wheeler M., Kubo I., Nakanishi K., and Naoki H. Tetrahedron Letters 22 (1981) 3451
106. Karelson M.M. J. Chem. Soc. Perkin Trans. 2 (1990) 195
107. Sugii M., Miura H., and Nagata K. Phytochemistry 20 (1981) 451
108. Barik B.R., Bhowmik T., Dey A.K., Patra A., Chatterjee A., Joy S., Susan T., Alam M., and Kundu A.B. Fitoterapia 63 (1992) 295
109. Yinghua L., Yamin C., Ximin W., Hongen W., Cunshen M., Ronglon Z., and Dequan Y. Chin. Chem. Lett. 4 (1993) 609
110. Yinghua L., Yamin C., Ximin W., Hongen W., Cunshen M., Ronglon Z., and Dequan Y. C. A. 120 (1994) 73332r
111. Morita Y., Hesse M., Schmid H., Banerji A., Banerji J., Chatterjee A., and Oberhänsli W.E. Helv. Chim. Acta 60 (1977) 1419
112. Achenbach H., Waibel R., and Zwanzger M. Phytochemistry 37 (1994) 1737
113. Zhang G.-L., Rücker G., Breitmaier E., Nieger M., Mayer R., and Steinbeck C. Phytochemistry 40 (1995) 299
114. Tsuda M., Hirano K., Kubota T., and Kobayashi J. Tetrahedron Lett. 40 (1999) 4819
115. Hirano K., Kubota T., Tsuda M., Mikami Y., and Kobayashi J. Chem. Pharm. Bull. 48 (2000) 974
116. Sarma A.S., Daum T., and Mtiller W.E.G. Secondary Metabolites from Marine Sponges (1993), Ullstein Mosby GmbH & Co. KG 56-64 Berlin
117. Ireland C.M., Molinsky T.F., Roll D.M., Zabriskie T.M., McKee T.C., Swersey J.C., and Foster M.P. In: Scheuer P.J. (Ed). Bioorganic Marine Chemistry Vol. 3 (1989), SpringerVerlag, Berlin 1
118. Krebs H.C. In: Herz W., Griesebach H., Kirby G.W., and Tamm C. (Eds). Progress in the Chemistry of Organic Natural Products Vol. 49 (1986), Springer-Verlag, Wien 151
119. Gribble G.W. In: Herz W., Kirby G.W., Moore R.E., Steglich W., and Tamm C. (Eds). Progress in the Chemistry of Organic Natural Products Vol. 68 (1996), Springer-Verlag, Wien 1
120. Cimino G., Sodano G., Self R., and Fenwick R.G. Gazz. Chim. Ital. 114 (1984) 533
121. Bergquist P.R. Sponges (1978), Hutchinson & Co (publishers) Ltd, London 178-179
122. Carney J.R., and Rinehart K.L. J. Nat. Prod. 58 (1995) 971
123. Ciminiello P., Dell'Aversano C., Fattorusso E., Magno S., and Pansini M. J. Nat. Prod. 63 (2000) 263
124. Kelecom A., and Kannengiesser G.J. An. Acad. Brasil Cienc. 51 (1979) 633
125. Garson M.J. Nat. Prod. Rep. 6 (1989) 143
126. Garson M.J. Chem. Rev. 93 (1993) 1699
127. Vacelet J. J. Microsc. (Paris) 23 (1975) 271
128. Vacelet J. J. Microsc. (Paris) 9 (1970) 333
129. Vacelet J. J. Microsc. (Paris) 12 (1971) 363
130. Thompson J.E., Barrow K.D., and Faulkner D.J. Acta Zoologica 64 (1983) 199
131. Turon X., Becerro M.A., and Uriz M.J. Cell Tissue Res. 301 (2000) 311
132. Vacelet J., and Donadey C. J. Exp. Mar. Biol. Ecol. 30 (1977) 301
133. Christophersen C. Comp. Biochem. Physiol. 98B (1991) 427
134. Christophersen C. In: Atta-ur-Rahman (Ed). Studies in Natural Products Chemistry Vol. 18 (1996), Elsevier Science B. V, Amsterdam 677
135. Bewley C.A., and Faulkner D.J. Angew. Chem. Int. Ed. 37 (1998) 2162
136. de Rosa M., Minale L., and Sodano G. Comp. Biochem. Physiol., B 45 (1973) 883
137. Tymiak A., and Rinehart Jr. K.L. J. Am. Chem. Soc. 103 (1981) 6763
138. Andersen R.J., and Faulkner D.J. Tetrahedron Lett. (1973) 1175
139. Kobayashi J., Honma K., Sasaki T., and Tsuda M. Chem. Pharm Bull. 43 (1995) 403
140. Longeon, Guyot M., and Vacelet J. Experientia 46 (1990) 548
141. Roll D.M., Chang C.W.J., Scheuer P.J., Gray G.A., Schoolery J.N., Matsumoto G.K., Van Duyne G.D., and Clardy J. J. Am. Chem. Soc. 107 (1985) 2916
142. Munro M.H.G., Luibrand R.T., and Blunt J.W. In: Scheuer P.J. (Ed). Biorganic Marine Chemistry Vol. 1 (1987), Springer-Verlag, Berlin 93
143. Eber R., Marin A., and Proksch P. Biochem. Syst. Ecol. 27 (1999) 769
144. Ebel R., Brenzinger M., Kunze A., Gross H.J., and Proksch P. J. Chem. Ecol. 23 (1997) 1451
145. Goldstein K., Fendert T., Proksch P., and Winterfeldt E. Tetrahedron 56 (2000) 4173
146. Weiss B., Ebel R., Elbraechter M., Kirchner M., and Proksch P. Biochem. Syst. Ecol. 24 (1996) 1
147. Thompson J.E. Mar. Biol. (Berlin) 88 (1985) 23
148. Walker R.P., Thompson J.E., and Faulkner D.J. Mar. Biol. 88 (1985) 27
149. Snider B.B., and Shi B. Tetrahedron Lett. 42 (2001) 1639
150. Ciminiello P., Fattorusso E., Magno S., and Pansini M. Biochem. Syst. Ecol. 24 (1996) 105 and correction
151. Ciminiello P., Fattorusso E., Magno S., and Pansini M. Biochem. Syst. Ecol. 24 (1996) 355
152. Ciminiello P., Costantino V., Fattorusso E., Magno S., Mangoni A., and Pansini M. J. Nat. Prod. 57 (1994) 705
153. Pulitzer-Finali G. Ann. Mus. civ., St. Nat. Genova 86 (1986) 65
154. Ciminiello P., Dell'Aversano C., Fattorusso E., Magno S., and Pansini M. J. Nat. Prod. 62 (1999) 590
155. Rodríguez A.D., and Piña I.C. J. Nat. Prod. 56 (1993) 907
156. Gopichand Y., and Schmitz F.J. Tetrahedron Lett. (1979) 3921
157. Mancini I., Guella G., Laboute P., Debitus C., and Pietra F. J. Chem. Soc., Perkin Trans. 1 (1993) 3121
158. Cimino G., DeRosa S., De Stefano S., Self R., and Sodano G. Tetrahedron Lett. 24 (1983) 3029
159. Ciminiello P., Fattorusso E., Forino M., Magno S., and Pansini M. Tetrahedron 53 (1997) 6565
160. Nishiyama S., and Yamamura S. Bull. Chem. Soc. Jpn. 58 (1985) 3453
161. Gunasekera M., and Gunasekera S.P. J. Nat. Prod. 52 (1989) 753
162. Fendert T., Wray V., van Soest R.W.M., and Proksch P. Z. Naturforsch. 54c (1999) 246
163. Nakamura H., Wu H., Kobayashi J., Nakamura Y., Ohizumi Y., and Hirata Y. Tetrahedron Lett. 26 (1985) 4517
164. Nakamura Y., Kobayashi M., Nakamura H., Wu H., Kobayashi J., and Ohizumi Y. Eur. J. Biochem. 167 (1987) 1
165. Benharref A., Païs M., and Debitus C. J. Nat. Prod. 59 (1996) 177
166. Kobayashi J., Tsuda M., Agemi K., Shigemori H., Ishibashi M., Sasaki T., and Mikami Y. Tetrahedron 47 (1991) 6617
167. Ciminiello P., Fattorusso E., Magno S., and Pansini M. J. Nat. Prod. 57 (1994) 1564
168. Ciminiello P., Dell'Aversano C., Fattorusso E., Magno S., Carrano L., and Pansini M. Tetrahedron 52 (1996) 9863
169. Aiello A., Albrizio S., Ciminello P., Costantino V., Fatturusso E., Magno S., Mangoni A., Menna M.L., and Pansini M. Seventh International Symposium on Marine Natural Products. Capri, Italy (1992) Contribution C8
170. Aiello A., Fattorusso E., Menna M., and Pansini M. Biochem. Syst. Ecol. 23 (1995) 377
171. Morris S.A., and Andersen R.J. Can. J. Chem. 67 (1989) 677
172. Gao H., Kelly M., and Hamann M.T. Tetrahedron 55 (1999) 9717
173. James D.M., Kunze H.B., and Faulkner D.J. J. Nat. Prod. 54 (1991) 1137
174. Copp B.R., Ireland C.M., and Barrows L.R. J. Nat. Prod. 55 (1992) 822
175. Tsukamoto S., Kato H., Hirota H., and Fusetani N. Tetrahedron 52 (1996) 8181
176. Ichiba T., Scheuer P.J., and Kelly-Borges M. J. Org. Chem. 58 (1993) 4149
177. Liu S., Fu X., Schmitz F.J., and Kelly-Borges M. J. Nat. Prod. 60 (1997) 614
178. Fattorusso E., Minale L., Sodano G., Moody K., and Thomson R.H. J. Chem. Soc., Chem. Commun. 752 (1970)
179. Moody K., Thomson R.H., Fattorusso E., Minale L., and Sodano G. J. Chem. Soc. Perkin 1 (1972) 18
180. McMillan J.A., Paul I.C., Goo Y.M., Rinehart Jr. K.L., Krueger W.C., and Pschigoda L.M. Tetrahedron Lett. 22 (1981) 39
181. Acosta A.L., and Rodríguez A.D. J. Nat. Prod. 55 (1992) 1007
182. Keman M.R., Cambie R.C., and Bèrgquist P.R. J. Nat. Prod. 53 (1990) 615
183. Schmitz F.J., and Gopichand Y. Lloydia 41 (1978) 654
184. Fattorusso E., Minale L., Moody K., Sodano G., and Thomson R.H. Gazz. Chim. Ital. 101 (1971) 61
185. Ciminiello P., Dell'Aversano C., Fattorusso E., and Magno S. Eur. J. Org. Chem. 55 (2001)
186. Gunasekera S.P., and Cross S.S. J. Nat. Prod. 55 (1992) 509
187. König G.M., and Wright A.D. Heterocycles 36 (1993) 1351
188. Compagnone R.S., Avila R., Suárez A.I., Abrams O.V., Rangel H.R., Arvelo F., Pina I.C., and Merentes E. J. Nat. Prod. 62 (1999) 1443
189. Encarnación R.D., Sandoval E., Malmstrom J., and Christophersen C. J. Nat. Prod. 63 (2000) 874
190. Rotem M., Carmely S., Kashman Y., and Loya Y. Tetrahedron 39 (1983) 667