Natural marine antiviral products

Studies in Natural Products Chemistry

Volumn 35, Issue C, 2008, Pages 101-134

  Abad Martinez, Maria Jose ^a   Bedoya Del Olmo, Luis Miguel ^a   Bermejo Benito, Paulina ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77954792707     PISSN: 15725995     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1572-5995(08)80005-1     Document Type: Chapter

References (142)

1. Che C. Drug Dev. Res 23 (1991) 201-218
2. Donia M., and Hamann M.T. Lancet Infect. Dis 3 (2003) 338-348
3. Gusdtafson K.R., Oku N., and Milanowski D.J. Curr. Med. Chem. Anti-infective Agents 3 (2004) 233-249
4. Mayer A.M., and Hamann M.T. Mar. Biotechnol. (NY) 6 (2004) 3752
5. Mayer A.M., and Hamann M.T. Comp. Biochem. Physiol 140 (2005) 265-286
6. Rinehart K.C., Holt T.G., Fregeau N.L., Keifer P.A., Wilson G.R., Perun Jr. T.J., Sakai-Thompson A.G., Stroh J.C., and Shield L.S. J. Nat. Prod 53 (1990) 771-792
7. Gudbjarnason S. Rit. Fiskideildar 16 (1999) 107-110
8. Sponga F., Cavaletti L., Lazzarini A., Borghi A., Ciciliato I., Losi D., and Marinella F. J. Biotechnol 70 (1999) 65-69
9. Luescher-Mattli M. Curr. Med. Chem. Anti-infective Agents 2 (2003) 219-225
10. Tziveleka L.A., Vogian C., and Roussis V. Curr. Top. Med. Chem 3 (2003) 1512-1535
11. Hayashi K., Hamada J., and Hayashi T. Phytother. Res 10 (1996) 233-237
12. Schaeffer D.J., and Krylov V.S. Ecotoxicol. Environ. Safety 45 (2000) 208-227
13. Nakamura H., Ohnuki N., S adamasu K., S ekine H., Tanaka J., Okada Y., and Okuyama T. Nat. Med 48 (1994) 173-179
14. Hudson J.B., Kim J.H., Lee M.K., DeWreede R.E., and Hong Y.K. J. Appl. Phycol 10 (1998) 427-434
15. Ahn M.J., Yoon K.D., Kim C.Y., Min S.Y., Kim Y.V., Kim H.J., Shin C.G., Lee C.K., Kim T.G., Kim S.H., Huh H., and Kim J. J. Appl. Phycol 14 (2002) 325-329
16. Ayehunie S., Belay A., Baba T.W., and Ruprecht R.M. J. AIDS Hum. Retrovirol 18 (1998) 7-12
17. Berge J.P., Bourgougnon N., Alban S., Pojer F., Billaudel S., Chermann J.C., Robert J.M., and Franz G. Planta Med 65 (1999) 604-609
18. Nicoletti E., Della Prieta F., Calderone V., Bandecchi P., Pistello M., Morelli I., and Cinelli F. Phytother. Res 13 (1999) 245-247
19. Miao B., Geng M., Li J., Li F., Chen H., Guan H., and Ding J. Biochem. Pharmacol 68 (2004) 641-649
20. Beutler J.A., McKee T.C., Fuller R.W., Tischler M., Cardellina J.H., Snader K.M., McCloud T.G., and Boyd M.R. Antiviral Chem. Chemother 4 (1993) 167-172
21. Witvrouw M., and De Clercq E. Gen. Pharmacol 29 (1997) 497-511
22. Hayashi K., Hayashi T., and Koj ima I. AIDS Res. Hum. Retroviruses 12 (1996) 1463-1471
23. Hayashi T., Hayashi K., Kojima I., and Maeda M. J. Nat. Prod 59 (1996) 83-87
24. Kolender A.A., Matulewicz M.C., and Cerezo A.S. Carbohydr. Res 273 (1995) 179-185
25. Bourgougnon N., Lahaye M., Chermann J.C., and Kornprobst J.M. Bioorg. Med. Chem. Lett 3 (1993) 1141-1146
26. Beress A., Wassermann O., Bruhn T., Beress L., Kraiserburd E.N., Gonzalez L.V., De Motta G.E., and Chavez P.I. J. Nat. Prod 56 (1993) 478-488
27. Hasui M., Matsuda M., Okatuni K., and Shigeta S. Int. J. Biol. Macromol 17 (1995) 293-297
28. Hashimoto K., Kodama E., Mori S., Watanabe J., Baba M., Okutani K., Matsuda M., and Shigeta S. Antiviral Chem. Chemother 7 (1996) 189-196
29. Botos I., O'Keefe B.R., Shenoy S.R., Cartner L.K., Ratner D.M., Seeberger P.H., Boyd M.R., and Wlodawer A. J. Biol. Chem 277 (2002) 34336-34342
30. Boyd M.R., Gustafson K.R., Mc Machon J.B., Shoemaker R.H., O'Keefe B.R., Mori T., Gulakowski R.J., Wu L., Rivera M.I., Laurencot C.M., Currens M.J., Cardellina J.H., Buckheit R.W., Nara P.L., Pannell L.K., Sowder R.C., and Henderson L.E. Antimicrob. Agents Chemother 41 (1997) 1521-1530
31. McMahon J.B., Beutler J.A., O'Keefe B.R., Goodrum C.B.B., Myers M.A., and Boyd M.R. J. Biomol. Scree (2000) 169-176 S
32. Bolmstedt A.J., O'Keefe B.R., Shenoy S.R., McMahon J.B., and Boyd M.R. Mol. Pharmacol 59 (2001) 949-954
33. Mori T., and Boyd M.R. Antimicrob. Agents Chemother 45 (2001) 664-672
34. Botos I., and Wlodawer A. Cell Mol. Life Sci 60 (2003) 277-287
35. Gustafson K.R., Sowder R.C., Henderson L.E., Cardellina J.H., McMahon J.B., Rajamani V., Pannell L.K., and Boyd M.R. Biochem. Biophys. Res. Commun 238 (1997) 223-228
36. Barrientos L.G., and Gronenborn A.M. Mini Rev. Med. Chem 5 (2005) 21-31
37. Mori T., O'Keefe B.R., Sowder II R.C., Bringan S., Gardella R., Berg S., Cochran P., Turpin J.A., Bucheit Jr. R.W., McMahon J.B., and Boyd M.R. J. Biol. Chem 280 (2005) 9345-9353
38. O'Keefe B.R., Beutler J.A., Cardellina II J.H., ; Gulakowski R.J., Krepps B.L., McMahon J.B., Sowder R.C., Henderson II L.E., Pannell L.K., Pomponi S.A., and Boyd M.R. Eur. J. Biochem 245 (1997) 47-53
39. Rajaganapathi J., Kathiresan K., and Singh T.P. Marine Biotechnol 4 (2002) 447-453
40. Bokesch H.R., O'Keefe B.R., McKee T.C., Pannell L.K., Patterson G.M.L., Gardella R.S., Sowder R.C., Turpin J., Watson K., Buckheit R.W., and Boyd M.R. Biochemistry 42 (2003) 2578-2584
41. Hirsch S., Rudi A., Kashman Y., and Loya Y. J. Nat. Prod. 54 (1991) 92-97
42. Schroder H.C., Begin M.E., Mocking R., Mathes E., Sarma A.S., Gasic M., and Muller W.E.G. Virus Res 21 (1991) 213-223
43. Cooper G.J., and Davies-Coleman M.T. Tetrahedron Lett 36 (1995) 3265-3268
44. Rashid M.A., Gustafson K.R., and Boyd M.R. J. Nat. Prod 63 (2000) 531-533
45. McKee T.C., Bokesch H.R., McCormick J.L., Rashid M.A., Spielvogel D., Gustafson K.R., Alavanja M.M., Cardellina J.H., and Boyd M.R. J. Nat. Prod 60 (1997) 431-438
46. Barbosa J.P., Pereira R.C., Abrantes J.L., Cirue dos Santos C.C., Rebello M.A., Frugulhetti I.C., and Teixeira V.L. Planta Med 70 (2004) 856-860
47. Pereira M.S., Leao-Ferreira L.R., Maussatche N., Teixeira V.L., Cavalcanti D.N., Costa L.J., Diaz R., and Frugulhetti I.C. Antiviral Res 64 (2004) 69-76
48. McKee T.C., Cardellina J.H., Riccio II R., D'Auria M.V., Iorizzi M., Minale L., Moran R.A., Gulakowski R.J., McMahon J.B., and Buckheit R.W. J. Med. Chem 37 (1994) 793-797
49. Bifulco G., Bruno I., Minale L., and Riccio R. J. Nat. Prod 57 (1994) 164-167
50. Rashid M.A., Gustafson K.R., Cartner L.K., Shigematsu N., Pannell L.K., and Boyd M.R. J. Nat. Prod 64 (2001) 117-121
51. Oku N., Gustafson K.R., Cartner L.K., Wilson J.A., Shigematsu N., Hess S., Pannell L.K., Boyd M.R., and McMahon J.B. J. Nat. Prod 67 (2004) 1407-1411
52. Hamann M.T., Otto C.S., Scheuer P.J., and Dunbar D.C. J. Org. Chem 61 (1996) 6594-6600
53. El-Sayed K.A., Nelly M., Kara U.A.K., Ang K.K.H., Katsuyama I., Dunbar D.C., Khan A.A., and Hamann M.T. J. Am. Chem. Soc 123 (2001) 1804-1808
54. Perry T.L., Dickerson A., Khan A.A., Kondru R.K., Beratan D.N., Wipf P., Nelly M., and Hamann M.T. Tetrahedron 57 (2001) 1483-1487
55. Reddy M., Venkata R., Rao M.R., Rhodes D., Hansen M.S.T., Rubins K., Bushman F.D., Venkateswarlu Y., and Faulkner D.J. J. Med. Chem 42 (1999) 1901-1907
56. Cutignano A., Bifulco G., Bruno I., Casapullo A., GomezPaloma L., and Riccio R. Tetrahedron 56 (2000) 3743-3748
57. Bailly C. Curr. Med. Chem. Anti-cancer Agents 4 (2004) 363-378
58. Peng J., Hu J.F., Kazi A.B., Li Z., Avery M., Peraud O., Hill R.T., Franzblau S.G., Zhang F., Schinazi R.F., Wirtz S.S., Tharnish P., Kelly M., Wahyuono S., and Hamann M.T. J. Am. Chem. Soc 125 (2003) 13382-13386
59. Yousaf M., Hammond N.L., Peng J., Wahyuono S., McIntosh K.A., Charman W.N., Mayer A.M., and Hamann M.T. J. Med. Chem 47 (2004) 3512-3517
60. Goud T.V., Srinavoso R.N., Raghavendra S.N., Siva R.T., and Venkateswarlu Y. Biol. Pharm. Bull 26 (2003) 1498-1501
61. Chang L.C., Whittaker N.F., and Bewley C.A. J. Nat. Prod 66 (2003) 1490-1494
62. Bringmann G., Lang G., Muhlbacher J., Schaumann K., Steffens S., Rytik P.G., Hentschel V., Morschhauser J., and Muller W.E. Prog. Mol. Subcell. Biol 37 (2003) 231-253
63. Loya S., Tal R., Hizi A., Issacs S., Kashman Y., and Loya I. J. Nat. Prod 56 (1993) 2120-2125
64. Bifulco G., Bruno I., Minale L., Riccio R., Debitus C., Bourdy G., Vassas A., and Lavayre J. J. Nat. Prod 58 (1995) 1444-1449
65. Ahn M.J., Yoon K.D., Min S.Y., Lee J.S., Kim J.H., Kim T.G., Kim S.H., Kim N.G., Huh H., and Kim J. Biol. Pharm. Bull 27 (2004) 544-547
66. Kim J.H., Hudson J.B., Huang A.M., Bannister K., Jin H., Choi T.J., Towers G.H.N., Hong Y.K., and De Wreede R.E. Can. J. Bot 75 (1997) 1656-1660
67. Ohta S., Ono F., Shiomi Y., Nakao T., Aozasa O., Nagate T., Kitamura K., Yamaguchi S., Nishi M., and Miyata H. J. Appl. Phycol 10 (1998) 349-355
68. Santos M.G.M., Lagrota M.H.C., Miranda M.M.F.S., Yoneshique-Valentin Y., and Wigg M.D. Bot. Mar 42 (1999) 227230
69. Serkedjieva J. Z. Naturforsch 55 (2000) 830-835
70. Serkedj ieva J. Phytother. Res 18 (2004) 480-483
71. Chamorro G., Salazar M., Araujo K.G.D., Dos Santos C.P., Ceballos G., and Castillo L.F. Arch. Latinoam. Nutr 52 (2002) 232240
72. Hernández A., Nieves I., Meckes M., Chamorro G., and Barron B.L. Antiviral Res 56 (2002) 279-285
73. Lee J.B., Srisomporn P., Hayashi K., Tanaka T., Sankawa V., and Hayashi T. Chem. Pharm. Bull 49 (2001) 108-110
74. Huleihel M., Ishanu V., Tal J., and Arad-Shoshana M. J. Appl. Phycol 13 (2001) 127-134
75. Huleihel M., Ishanu V., Tal J., and Arad-Shoshana M. J. Biochem. Biophys. Meth 50 (2002) 189-200
76. Zhu W., Ooi V.E.C., Chan P.K.S., and Ang P.O. Biochem. Cell Biol 81 (2003) 25-33
77. Zhu W., Chiu L.C., Ooi V.E., Chan P.K., and Ang Jr. P.D. Int. J. Antimicrob. Agents 24 (2004) 279-283
78. Hoshino T., Hayashi T., Hayashi K., Hamada J., Lee J.B., and Sankawa V. Biol. Pharm. Bull 21 (1998) 730-734
79. Preeprame S., Hayashi K., Lee J.B., Sankawa V., and Hayashi T. Chem. Pharm. Bull 49 (2001) 484-485
80. Lee J.B., Hayashi K., Maeda M., and Hayashi T. Planta Med 70 (2004) 813-817
81. Ghosh P., Adhikari V., Ghosal P.K., Pujol C.A., Carlucci M.J., Damonte E.B., and Ray B. Phytochemistry 65 (2004) 3151-3157
82. Carlucci M.J., Pujol C.A., Ciancio M., Noseda M.D., Matulewicz M.C., Damonte E.B., and Cerezo A.S. Int. J. Biol. Macromol 20 (1997) 97-105
83. Carlucci M.J., Scolaro L.A., and Damonte E.B. J. Med. Virol 68 (2002) 92-98
84. Carlucci M.J., Ciencia M., Matulewicz M.C., Cerezo A.S., and Damonte E.B. Antiviral Res 43 (1999) 93-102
85. Caceres P.J., Carlucci M.J., Damonte E.B., Matsuhiro B., and Zuñiga E.A. Phytochemistry 53 (2000) 81-86
86. Talarico L.B., Zibetti R.G., Faria P.C., Scolaro L.A., Duarte M.F., Nocedal M.D., Pujol C.A., and Damonte E.B. Int. J. Biol. Macromol 34 (2004) 63-71
87. Thompson K.D., and Dragar C. Phytother. Res 18 (2004) 551-555
88. Duarte M.E., Canduro J.P., Noseda D.G., Noseda M.D., Gonzalves A.G., Pujol C.A., Damonte E.B., and Cerezo A.S. Carbohydr. Res 339 (2004) 335-347
89. Duarte M.E.R., Noseda D.G., Noseda M.D., Tulio S., Pujol C.A., and Damonte E.B. Phytomedicine 8 (2001) 53-58
90. Pujol C.A., Errea M.I., Matulewicz M.C., and Damonte E.B. Phytother. Res 10 (1996) 410-413
91. Carlucci M.J., Scolaro L.A., Errea M.I., Matulewicz M.C., and Damonte E.B. Planta Med 63 (1997) 429-432
92. Kolender A.A., Pujol C.A., Damonte E.B., Matulewicz M.C., and Cerezo A.S. Carbohydr. Res 304 (1997) 53-60
93. Ponce N.M.A., Pujol C.A., Damonte E.B., Flores M.L., and Stortz C.A. Carbohydr. Res 338 (2003) 153-165
94. Siamopoulou P., Bimplakis A., Iliopoulou D., Vagias C., Cos P., Vanden Berghe D., and Roussis V. Phytochemistry 65 (2004) 20252030
95. Knubel G., Larsen L.K., Moore R.E., Levine I.A., and Patterson G.M. J. Antibiot 43 (1990) 1236-1239
96. Larsen L.K., Moore R.E., and Patterson G.M.L. J. Nat. Prod 57 (1994) 419-421
97. Betancour G.L., Zuluaga C., Arno M., Gonzalez M.A., and Zaragoza R.J. J. Nat. Prod 65 (2002) 189-192
98. Rodriguez I.L., Shi Y.P., Garcia O.J., Rodriguez A.D., Mayer A.M., Sanchez J.A., Ortega-Barrio E., and Gonzalez J. J. Nat. Prod 67 (2004) 1672-1680
99. Tanaka J.I., Ogawa N., Liang J., Higa T., and Garcia-Gravalos D. Tetrahedron 49 (1993) 811-822
100. El Sabed K.A., Hamann M.T., Hashish N.E., Shier W.T., Kelly M., and Khan A.A. J. Nat. Prod 64 (2001) 522-524
101. Maier M.S., Rocatagliata A.J., Kuriss A., Chludil H., Seldes A.M., Pujol C.A., and Damonte E.B. J. Nat. Prod 64 (2001) 732-736
102. Comin M.J., Maier M.S., Rocatagliata A.J., Pujol C.A., and Damonte E.B. Steroids 64 (1999) 335-340
103. Coutinho A.F., Chanas B., Souza T.M.L.E., Frugrulhetti I.C.P.P., and Epifanio R.D. Heterocycles 57 (2002) 1265-1272
104. Ichiba T., Corgiat J.M., Scheuer P.J., and Kelly-Borges M. J. Nat. Prod 57 (1994) 168-170
105. Matsuda M., Shigeta S., and Okutani K. Marine Biotechnol 1 (1999) 68-73
106. Kanekiyo K., Lee J.B., Hayashi K., Takenaka H., Hayakawa Y., Endo S., and Hayashi T. J. Nat. Prod 68 (2005) 1037-1041
107. Davidson B.S., and Schumacher R.W. Tetrahedron 49 (1993) 65696574
108. Rowley D.C., Kelly S., Kauffman C.A., Jensen P.R., and Fenical W. Bioorg. Med. Chem 11 (2003) 4263-4274
109. Rowley D.C., Kelly S., Jensen P., and Fenical W. Bioorg. Med. Chem 12 (2004) 4929-4936
110. Bonnard I., and Rinehart K.L. Tetrahedron 60 (2004) 2987-2992
111. Patra A., and Majundar A. Arkivoc 9 (2003) 133-139
112. Damonte E.B., Matulewicz M.C., and Cerezo A.S. Curr. Med. Chem 11 (2004) 2399-2419
113. Blinkova L.P., Gorobets O.B., and Baturo A.P. Zh. Mikrobiol. Epidemiol. Immunobiol 2 (2001) 114-118
114. Iwashima M., Mori J., Ting X., Matsunaga T., Hayashi K., Shinoda D., Saito H., Sankawa U., and Hayashi T. Biol. Pharm. Bull 28 (2005) 374-377
115. S erkedj ieva J., Konaklieva M., Dimitrova-Konaklieva S., Ivanova V., Stefanov K., and Popov S. Z. Naturforsch 55 (2000) 8793
116. Wegner V., Mundt S., Kliefoth C., Meyer B., Lindequist U., and Menter R. Hyg. Med 25 (2000) 75-78
117. Zainuddin E.N., Mundt S., Wegner V., and Mentel R. Med. Microbiol. Immunol 191 (2002) 181-182
118. Nowotny A., Mentel R., Wegner V., Mundt S., and Lindequist U. Phytother. Res 11 (1997) 93-96
119. Mundt S., Nowotny A., Mentel R., Lesnau A., and Lindequist U. Pharm. Pharmacol. Lett 7 (1997) 161-163
120. Chatterji A., Ansari Z.A., Ingole B.S., Bichurina M.A., Sovetova M., and Boikov Y.A. Curr. Sci 82 (2002) 1279-1282
121. Ivanova V., Rouseva R., Kolarova M., S erkedj ieva J., Racheu R., and Manolova N. Prep. Biochem 24 (1994) 83-97
122. Ahmad A.S., Matsuda M., Shigeta S., and Okutani K. Marine Biotechnol 1 (1999) 102-106
123. Wright A.E., Rueth S.A., and Cross S.S. J. Nat. Prod 54 (1991) 1108-1111
124. Premanathan M., Kathiresan K., Chandra K., and Bajpai S.K. Indian J. Med. Res 99 (1994) 236-238
125. Nakano T., and Kamei Y. Bot. Mar 48 (2005) 84-86
126. Fabregas J., Garcia D., Fernandez-Alonso M., Rocha A.I., Gomez-Puertas P., Escribano J.M., Otero A., and Coll J.M. Antiviral Res 44 (1999) 67-73
127. Premanathan M., Kathiresan K., and Chandra K. Int. J. Pharmacogn 33 (1995) 75-77
128. Romanos M., Andrada-Serpa M.J., Dos S., Ribeiro A., Yoneshique-Valentin Y., Costa S.S., and Wigg M.D. Cancer Invest 20 (2002) 154-155
129. Direkbusarakom S., Yoshimizu M., Ezura Y., Ruangpan L., and Danayadol Y. J. Mar. Biotechnol 6 (1998) 266-267
130. Rajaganapathi J., Thyagarajan S.P., and Edward J.K. Indian J. Exp. Biol 38 (2000) 519-520
131. Huleihel M., and Arad S. Anticancer Res 21 (2001) 2073-2078
132. Yim J.H., Kim S.J., Ahn S.H., Lee C.K., Rhie K.T., and Lee H.K. Marine Biotechnol 6 (2004) 17-25
133. Pardee K.I., Ellis P., Bouthillier M., Towers G.H.N., and French C.J. Can. J Bot 82 (2004) 304-309
134. Reunov A., Nagorskaya V., Lapshina L., Yermak I., and Barabanova A. J. Plant Dis. Protect 111 (2004) 165-172
135. Gauvin A., Smadja J., Aknin M., F aure R., and Gaydon E.M. Can. J. Chem 78 (2000) 986-992
136. Gunasekera S.P., and Cross S.S. J. Nat. Prod (1992) 509-512 SS
137. Silvestri I., Albonici L., Ciotti M., Lombardi M.P., Sinibaldi P., Manzani V., Orlando P., Carretta F., Strazzullo G., and Grippo P. Experientia 51 (1995) 1076-1080
138. Koehn F.E., Gunasekera S.P., Niel D.N., and Cross S.S. Tetrahedron Lett 32 (1991) 169-172
139. Venkateswarlu Y., Reddy M.V.R., Ramesh P., and Tao J.V. Indian J. Chem 38 (1999) 254-256
140. Rader T.H., Yamada Y., and Ankel H. Antiviral Res 16 (1991) 341355
141. Mehta A.S., Gu B., Conyers B., Ouzounov S., Wang L., Moriarty R.M., Dwek R.A., and Block T.M. Antimicrob. Agents Chemother 48 (2004) 2085-2090
142. Shih S.R., Tsai K.N., Li Y.S., Chueh C.C., and Chan E.C. J. Med. Virol 70 (2003) 119-125