Bioactive peroxides as potential therapeutic agents

European Journal of Medicinal Chemistry

Volumn 43, Issue 2, 2008, Pages 223-251

  Dembitsky, Valery M ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Alkaloids; Anticancer; Cytotoxic; Fatty acids; Peptides; Peroxides; Steroids; Terpenoids

Indexed keywords

1,2 DIOXOLANE PEROXIDE ACID DERIVATIVE; ACETOGENIN PEROXIDE DERIVATIVE; ALKALOID DERIVATIVE; ANDAVADOIC ACID; ANTINEOPLASTIC AGENT; ARTEMISININ; ASCARIDOLE; CHONDRILLIN; DIHYDROASCARIDOLE; EPIPLAKINIC ACID; FATTY ACID; FATTY ACID DERIVATIVE; GINSENOYNE K; HATERUMADIOXIN B; MANADIC ACID A; MYCAPEROXIDE H; NORSESTERTERPENE 1,2 DIOXANE DERIVATIVE; PEPTIDE DERIVATIVE; PEROXIDE; PLAKINIC ACID; PLAKORIN; PLAKORTIDE DERIVATIVE; SIGMOSCOTRELLIN DERIVATIVE; STEROID; STOLONIC ACID DERIVATIVE; STOLONOXIDE A; TASNEMOXIDE DERIVATIVE; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; XESTIN DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIMALARIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; CYTOTOXICITY; DRUG ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; LAND BIOME; MARINE ENVIRONMENT; NONHUMAN; REVIEW; SPONGE (PORIFERA);

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; PEROXIDES;

EID: 38949159992     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2007.04.019     Document Type: Review

References (250)

1. Dembitsky V.M., Gloriozova T.A., and Poroikov V.V. Mini Rev. Med. Chem. 7 (2007) 571-589
2. Casteel D.A. Nat. Prod. Rep. 16 (1999) 55-73
3. Jung M., Kim H., Lee K., and Park M. Mini Rev. Med. Chem. 3 (2003) 159-165
4. Casteel D.A. Nat. Prod. Rep. 9 (1992) 289-312
5. Lee K.R. Saengyak Hakhoechi (in Korean) 22 (1991) 145-155
6. Matsugo S., Kayamori N., and Konishi T. Niigata Yakka Daigaku Kenkyu Hokoku (in Japanese) 6 (1986) 23-37
7. Omari A., and Garner P. Clin. Evid. 9 (2003) 850-860
8. Omari A., and Garner P. Clin. Evid. 11 (2004) 1047-1057
9. Jefford C.W. Curr. Opin. Investig. Drugs 5 (2004) 866-872
10. Tang Y., Dong Y., and Vennerstrom J.L. Med. Res. Rev. 24 (2004) 425-428
11. McCullough K.J., and Nojima M. Curr. Org. Chem. 5 (2001) 601-636
12. In: Ando W. (Ed). Organic Peroxides (1992), J. Wiley & Sons, New York, NY
13. Ghezai M., Ming W., Bala S., and Daryle H. Coord. Chem. Rev. 219-221 (2001) 789-820
14. Collins A.N., Sheldrake G.N., and Crosby J. Chirality in Industry (1998), J. Wiley & Sons, New York
15. Sanfilippo C., Patti A., Piattelli M., and Nicolosi G. Tetrahedron: Asymmetry 9 (1998) 2809-2817
16. Sanfilippo C., Patti A., and Nicolosi G. Tetrahedron: Asymmetry 10 (1999) 3273-3276
17. Dembitsky V.M. Tetrahedron 59 (2003) 4701-4720
18. Franssen M.C.R. Catalysis Today 22 (1994) 441-457
19. Sekera A., and Rahm J. Cesk. Farm. 1 (1952) 471-477
20. Ziemann H. Rundschau Deut. Tech. 18 (1938) 9
21. Naves Y.R. Parfums de France 13 (1935) 4-13
22. Duviau G. J. Med. Bord. 130 (1953) 44-51
23. Wautie A. Parasitica, 2 (1946) 44-67
24. Guimaraes F. C. R. Seances Soc. Biol. Fil. 96 (1927) 1251-1253
25. Faust E.C. JAMA, J. Am. Med. Assoc. 108 (1937) 386-392
26. Opdyke D.L.J. Food Cosmet. Toxicol. 14 Suppl. (1976) 713-715
27. Bhargava A., Shukla S., and Ohri D. J. Med. Arom. Plant Sci., 27 (2005) 309-319
28. Harder A. Parasitol. Res., 88 (2002) 477-480
29. Wells R.J. Tetrahedron Lett., 17 (1976) 2637-2638
30. A.D. Patil, PCT Int. Appl. US Patent 86-825920 19860204, 1987, 29 pp.
31. Patil A.D., Freyer A.J., Bean M.F., Carte B.K., Westley J.W., and Johnson R.K. Tetrahedron, 52 (1996) 377-394
32. Davidson B.S. J. Org. Chem. 56 (1991) 6722-6724
33. Horton P.A., Longley R.E., Kelly-Borges M., McConnell O.J., and Ballas L.M. J. Nat. Prod. 57 (1994) 1374-1381
34. Sandler J., Colin P.L., Hooper J.N.A., and Faulkner D.J. J. Nat. Prod. 65 (2002) 1258-1261
35. Rudi A., Afanii R., Gravalos L.G., Aknin M., Gaydou E., Vacelet J., and Kashman Y. J. Nat. Prod. 66 (2003) 682-685
36. Holzwarth M., Trendel J.-M., Albrecht P., Maier A., and Michaelis W. J. Nat. Prod. 68 (2005) 759-761
37. Shen Y.C., Prakash C.V., and Kuo Y.H. J. Nat. Prod. 64 (2001) 324-327
38. Higgs M.D., and Faulkner D.J. J. Org. Chem. 43 (1978) 3454-3457
39. Longley R.E., McConnell O.J., Essich E., and Harmody D. J. Nat. Prod. 56 (1993) 915-920
40. T. Higa, S. Sakemi Jr., C. Christophersen, PCT Int. Appl. WO 8704709 A1 19870813 Application WO87-US135 19870121, 1987, 31 pp.
41. De Guzman F.S., and Schmitz F.J. J. Nat. Prod. 53 (1990) 926-931
42. Murayama T., Ohizumi Y., Nakamura H., Sasaki T., and Kobayashi J. Experientia 45 (1989) 898-899
43. J. Kobayashi, T. Murayama, Y. Oizumi, Jpn. Kokai Tokkyo Koho, Japanese Patent JP 02229185, 1990.
44. Dussault P.H., Eary C.T., Woller K.R., and Org J. Chem. 64 (1999) 1789-1797
45. Sakemi S., Higa T., Anthoni U., and Christophersen C. Tetrahedron 43 (1987) 263-268
46. Quinoa E., Kho E., Manes L.V., Crews P., and Bakus G.J. J. Org. Chem. 51 (1986) 4260-4264
47. Takada N., Watanabe M., Yamada A., Suenaga K., Yamada K., Ueda K., and Uemura D. J. Nat. Prod. 64 (2001) 356-359
48. Gochfeld D.J., and Hamann M.T. J. Nat. Prod. 64 (2001) 1477-1479
49. Patil A.D., Freyer A.J., Carte B., Johnson R.K., and Lahouratate P. J. Nat. Prod. 59 (1996) 219-223
50. Fattorusso E., Taglialatela-Scafati O., Di Rosa M., and Ianaro A. Tetrahedron 56 (2000) 7959-7967
51. Hu J.-F., Gao H.-F., Kelly M., and Hamann M.T. Tetrahedron 57 (2001) 9379-9383
52. Del Sol Jimenez M., Garzon S.P., and Rodriguez A.D. J. Nat. Prod. 66 (2003) 655-661
53. Harrison B., and Crews P. J. Nat. Prod. 61 (1998) 1033-1037
54. Lim C.W., Cha Y.J., and Kim J.S. J. Fisheries Sci. Technol. 8 (2005) 6-9
55. Fattorusso E., Parapini S., Campagnuolo C., Basilico N., Taglialatela-Scafati O., Taramelli D., and Antimicrob J. Chemother. 50 (2002) 883-888
56. Berrue F., Thomas O.P., Funel-Le Bon C., Reyes F., and Amade P. Tetrahedron 61 (2005) 11843-11849
57. Williams D.E., Allen T.M., Van Soest R., Behrisch H.W., and Andersen R.J. J. Nat. Prod. 64 (2001) 281-285
58. Chen Y., Killday K.B., McCarthy P.J., Schimoler R., Chilson K., Selitrennikoff C., Pomponi S.A., and Wright A.E. J. Nat. Prod. 64 (2001) 262-264
59. Bums D.J., Bloomenthal J., Lee M., and Bell R.M. J. Biol. Chem. 265 (1990) 12044-12051
60. Basta P., Strickland M.B., Holmes W., Loomis C.R., Ballas L.M., and Burns D.J. Biochem. Biophys. Acta 1132 (1992) 154-160
61. Davidson B.S. Tetrahedron Lett. 32 (1991) 7167-7170
62. See Ref. [35].
63. Perry T.L., Dickerson A., Khan A.A., Kondru R.K., Beratan D.N., Wipf P., Kelly M., and Hamann M.T. Tetrahedron 57 (2001) 1483-1487
64. Rudi A., Talpir R., Kashman Y., Benayahu Y., and Schleyer M. J. Nat. Prod. 56 (1993) 2178-2182
65. Gunasekera S.P., Gunasekera M., Gunawardana G.P., McCarthy P., and Burres N. J. Nat. Prod. 53 (1990) 669-674
66. Pettit G.R., Nogawa T., Knight J.C., Doubek D.L., and Hooper J.N.A. J. Nat. Prod. 67 (2004) 1611-1613
67. Ichiba T., Scheuer P.J., and Kelly-Borges M. Tetrahedron 51 (1995) 12195-12202
68. Toth S.I., and Schmitz F.J. J. Nat. Prod. 57 (1994) 123-127
69. Davies-Coleman M.T., Cantrell C.L., Gustafson K.R., Beutler J.A., Pannell L.K., and Boyd M.R. J. Nat. Prod. 63 (2000) 1411-1413
70. Fontana A., Gonzalez M.C., Gavagnin M., Templado J., and Cimino G. Tetrahedron Lett. 41 (2000) 429-432
71. Duran R., Zubi{dotless}'a E., Ortega M.J., Naranjo S., and Salva J. Tetrahedron 56 (2000) 6031-6037
72. R. Duran, E. Zubia, M.J. Ortega, J. Salva, J.L. Fernandez Puentes, D. Garcia Gravalos, L. Naranjo, PCT Int. Appl., Great Britain Patent WO 2001083477 A1 20011108, 2001, 24 pp.
73. Fontana A., Cimino G., Gavagnin M., Gonzalez M.C., and Estornell E. J. Med. Chem. 44 (2001) 2362-2365
74. Compagnone R.S., Pina I.C., Rangel H.R., Dagger F., Suarez A.I., Reddy M.V.R., and Faulkner D.J. Tetrahedron 54 (1998) 3057-3068
75. Qureshi A., Salva J., Harper M.K., and Faulkner D.J. J. Nat. Prod. 61 (1998) 1539-1542
76. Chen Y., McCarthy P.J., Harmody D.K., Schimoler-O'Rourke R., Chilson K., Selitrennikoff C., Pomponi S.A., and Wright A.E. J. Nat. Prod. 65 (2002) 1509-1512
77. Stierle D.B., and Faulkner D.J. J. Org. Chem. 44 (1979) 964-968
78. Phillipson D.W., and Rinehart Jr. K.L. J. Am. Chem. Soc. 105 (1983) 7735-7736
79. Hirakura K., Morita M., Nakajima K., Ikeya Y., and Mitsuhashi H. Phytochemistry 31 (1992) 899-903
80. K. Hirakura, H. Mihashi, T. Fujihashi, T. Okuma, Jpn. Kokai Tokkyo Koho, Japanese Patent JP 04352742 A2 19921207 Heisei, 1992, 10 pp.
81. Yosief T., Rudi A., Wolde-ab Y., and Kashman Y. J. Nat. Prod. 61 (1998) 491-493
82. Fontana A., D'Ippoloto G., D'Souza L., Mollo E., Parameswaram P.S., and Cimino G. J. Nat. Prod. 64 (2001) 131-133
83. Dussault P., Xu C., and Raible J.M. Abstracts of Papers (2005), 229th ACS National Meeting, San Diego, CA, United States, March pp. 13-17
84. Youssef D.T. J. Nat. Prod. 67 (2004) 112-114
85. Guo Y., Gavagnin M., Mollo E., Trivellone E., Cimino G., Hamdy N.A., Fakhr I., and Pansini M. Nat. Prod. Lett. 9 (1996) 105-112
86. Tanaka J., Higa T., Suwanborirux K., Kokpol U., Bernardinelli G., and Jefford C.W. J. Org. Chem. 58 (1993) 2999-3002
87. J.-I. Tanaka, T. Higa, K. Suwanoborirux, C.W. Jefford, G. Bernardinelli, D.G. Gravalos, Eur. Pat. Appl. European Patent EP 610076 A1 19940810, 1994, 8 pp.
88. Capon R.J., Rochfort S.J., Ovenden S.P.B., and Metzger R.P. J. Nat. Prod. 61 (1998) 525-528
89. Phuwapraisirisan P., Matsunaga S., Fusetani N., Chaitanawisuti N., Kritsanapuntu S., and Menasveta P. J. Nat. Prod. 66 (2003) 289-291
90. Phuwapraisirisan P., Matsunaga S., and Fusetani N. Org. Lett. 26 (2005) 2233-2236
91. Youssef D.T., Yoshida W.Y., Kelly M., and Scheuer P.J. J. Nat. Prod. 64 (2001) 1332-1335
92. Sokoloff S., Halevy S., Usieli V., Colorni A., and Sarel S. Experientia 38 (1982) 337-338
93. Sperry S., Valeriote F.A., Corbett T.H., and Crews P. J. Nat. Prod. 61 (1998) 241-247
94. Albericci M., Braekman J.C., Daloze D., and Tursch B. Tetrahedron 38 (1982) 1881-1890
95. Albericci M., Collart-Lempereur M., Braekman J.C., Daloze D., Tursch B., Declercq J.P., Germain G., and Van Meerssche M. Tetrahedron Lett. 29 (1979) 2687-2690
96. Pare P.W., Zajicek J., Ferracini V.L., and Melo I.S. Biochem. Syst. Ecol. 21 (1993) 649-653
97. Pollack Y., Segal R., and Golenser J. Parasitol. Res. 76 (1990) 570-572
98. Kiuchi F., Itano Y., Uchiyama N., Honda G., Tsubouchi A., Nakajima-Shimada J., and Aoki T. J. Nat. Prod. 65 (2002) 509-512
99. Monzote L., Montalvo A.M., Almanonni S., Scull R., Miranda M., and Abreu J. Chemotherapy 52 (2006) 130-136
100. Efferth T., Olbrich A., Sauerbrey A., Ross D.D., Gebhart E., and Neugebauer M. Anticancer Res. 22C (2002) 4221-4224
101. V.M. Dembitsky, S. Abu-Lafi, L.O. Hanus, Biores. Technol. 98 (2007) in press.
102. Smith B.D. Proc. Natl. Acad. Sci. USA. 103 (2006) 12223-12228
103. Beckett A.H., Donbrow M., Jolliffe G.O., and Pharm J. Pharmacol. 7 (1955) 55-65
104. Beckett A.H., Jolliffe G.O., and Pharm J. Pharmacol. 7 (1955) 606-607
105. Kliks M.M. Soc. Sci. Med. 21 (1985) 879-886
106. MacDonald D., VanCrey K., Harrison P., Rangachari P.K., Rosenfeld J., Warren C., and Sorger G. J. Ethnopharmacol. 92 (2004) 215-221
107. Okuyama E., Umeyama K., Saito Y., Yamazaki M., and Satake M. Chem. Pharm. Bull. 41 (1993) 1309-1311
108. Van Duuren B.L., Orris L., and Nelson N. J. Natl. Cancer Inst. 35 (1965) 707-717
109. Cavalli J.-F., Tomi F., Bernardini A.-F., and Casanova J. Phytochem. Anal. 15 (2004) 275-279
110. Chowdhury J.U., Yusuf M., Begum J., Taniya A.J., Hossain M.E., and Hossain M.A. Indian Perfumer. 49 (2005) 61-65
111. Paget H. J. Chem. Soc. (1938) 829-833
112. Carballeira L., Mosquera R.A., and Rios M.A. J. Comput. Chem. 10 (1989) 911-920
113. Rebello S., da Costa S.F.G., and Rico J.T. C.R. Seances Soc. Biol. Fil. 98 (1928) 995-997
114. Tan R.X., Zheng W.F., and Tang H.Q. Planta Med. 64 (1998) 295-302
115. Koo H.-N., Hong S.-H., Jeong H.-J., Lee E.-H., Kim N.-G., Choi S.-D., Ra K.-W., Kim K.-S., Kang B.-K., Kim J.-J., Oh J.G., and Kim H.-M. Immunopharm. Immunotoxicol. 24 (2002) 441-453
116. Lee T.E., Park S.W., and Min T.J. J. Biochem. Mol. Biol. 32 (1999) 585-593
117. Li Y., Li M., Wang L., Jiang Z., Li W., and Li H. Sichuan Da Xue Xue Bao Yi Xue Ban 35 (2004) 337-339
118. Kwon H.C., Choi S.U., and Lee K.R. Archiv. Pharmacal Res. 23 (2000) 151-154
119. Ruecker G., Manns D., and Wilbert S. Phytochemistry 31 (1992) 340-342
120. Li Y., and Wu Y.L. Med. Trop. (Mars) 58 Suppl. 3 (1998) 9-12
121. Singh N.P., and Lai Henry C. Anticancer Res. 24 (2004) 2277-2780
122. Woerdenbag H.J., Moskal T.A., Pras N., Malingre T.M., El-Feraly F.S., Kampinga H.H., and Konings A.W. J. Nat. Prod. 56 (1993) 849-856
123. Balachandran S., Vishwakarma R.A., and Popli S.P. Indian J. Pharm. Sci. 49 (1987) 152-154
124. Kim H.-S., Nagai Y., Ono K., Begum K., Wataya Y., Hamada Y., Tsuchiya K., Masuyama A., Nojima M., and McCullough K.J. J. Med. Chem. 44 (2001) 2357-2361
125. Gonzalez A.G., Martin J.D., Perez C., Rovirosa J., Tagle B., and Clardy J. Chem. Lett. 10 (1984) 1649-1652
126. Sy L.-K., and Brown G.D. Tetrahedron 54 (1998) 4345-4356
127. Beekman A.C., Wierenga P.K., Woerdenbag H.J., Van Uden W., Pras N., Konings A.W., El-Feraly F.S., Galal A.M., and Wikstrom H.V. Planta Med. 64 (1998) 615-619
128. Stojanovic G., Radulovic N., Hashimoto T., and Palic R. J. Ethnopharmacol. 101 (2005) 185-190
129. Barel S., Segal R., and Yashphe J. J. Ethnopharmacol. 33 (1991) 187-191
130. Bezic N., Skocibusic M., Dunkic V., and Radonic A. Phytother. Res. 17 (2003) 1037-1040
131. Unlu M., Daferera D., Donmez E., Polissiou M., Tepe B., and Sokmen A. J. Ethnopharmacol. 83 (2002) 117-121
132. Kundakovic T., Stanojkovic T., Juranic Z., and Kovacevic N. Pharmazie 60 (2005) 319-320
133. Tsankova E., Jacobsson Kempe U., Norin T., and Ognyanov I. Phytochemistry 20 (1981) 1436-1438
134. Trifunovic S., Vajs V., Juranic Z., Zizak Z., Tesevic V., Macura S., and Milosavljevic S. Phytochemistry 67 (2006) 887-893
135. Bohlmann F., and Knoll K.H. Phytochemistry 18 (1979) 995-1001
136. Duh C.-Y., Chia M.-C., Wang S.-K., Chen H.-J., El-Gamal A.A.H., and Dai C.F. J. Nat. Prod. 64 (2001) 1028-1031
137. Erickson K.L., Beutler J.A., Gray G.N., Cardellina II J.H., and Boyd M.R. J. Nat. Prod. 58 (1995) 1848-1860
138. Nam N.-H., Kim H.-M., Bae K.-H., and Ahn B.-Z. Phytotherapy Res. 17 (2003) 107-111
139. Le T.C., Nguyen Q.H., Le M.P., Le V.H., Le T.T., Pham D.M., Nguyen T.D., Nguyen T.L.H., and Nguyen V.B. Tap Chi Duoc Hoc (Vietnam) 2-3 (1987) 12-17
140. Xu X.-H., Kong C.-H., Lin C.-J., Wang X., Zhu Y.-D., and Yang H.-S. Chin. J. Chem. 21 (2003) 1506-1509
141. Handa S.S., Kinghorn A.D., Cordell G.A., and Farnsworth N.R. J. Nat. Prod. 46 (1983) 123-126
142. Alam M., Martin G.E., Zektzer A.S., Weinheimer A.J., Sanduja R., and Ghuman M.A. J. Nat. Prod. 56 (1993) 774-779
143. Araya J.E., Neira I., da Silva S., Mortara R.A., Manque P., Cordero E., Sagua H., Loyola A., Borquez J., Morales G., and Gonzalez J. Memorias do Instituto Oswaldo Cruz (Sao Paulo, Brazil) 98 (2003) 413-418
144. Doskotch R.W., El-Feraly F.S., Fairchild E.H., and Huang C.T. J. Chem. Soc. Chem. Commun. (1976) 402
145. Zheng G.C., Ichikawa A., Ishitsuka M.O., Kusumi T., Yamamoto H., and Kakisawa H. J. Org. Chem. 55 (1990) 3677-3679
146. Schulte K.E., Glauch G., and Rucker G. Nardosinon, ein neuer inhaltsstoff von nardostachys chinensis batalin. Tetrahedron Lett. 35 (1965) 3083-3084
147. Rucker G., Kahrs K.H., and Hembeck H.W. Arch. Pharm. (Weinheim) 308 (1975) 858-862
148. Itokawa H., Masuyama K., Morita H., and Takeya K. Chem. Pharm. Bull. (Tokyo) 41 (1993) 1183-1184
149. Zhang Y., Lu Y., Zhang L., Zheng Q.T., Xu L.Z., and Yang S.L. J. Nat. Prod. 68 (2005) 1131-1133
150. Ruecker G., Shide L., and Olbrich A. Arch. Pharm. (Weinheim) 323 (1990) 171-175
151. Li P., Matsunaga K., Yamamoto K., Yoshikawa R., Kawashima K., and Ohizumi Y. Neurosci. Lett. 273 (1999) 53-56
152. Li P., Matsunaga K., Yamakuni T., and Ohizumi Y. Brain Res. Dev. Brain Res. 145 (2003) 177-183
153. Yamada Y. Yakugaku Zasshi 122 (2002) 727-743
154. Ahmed A.F., Kuo Y.-H., Dai C.-F., and Sheu J.-H. J. Nat. Prod. 68 (2005) 1208-1212
155. Hashidoko Y., Tahara S., and Mizutani J. Phytochemistry 31 (1992) 779-782
156. Liang X. In: Chang H.M. (Ed). Advances in Chinese Medical Materials Research, International Symposium (1985), World Sci., Singapore, Singapore 427-432
157. Adams R.P. Junipers of the World: The Genus Juniperus (2004), Trafford Publ., Vancouver, B.C., Canada p. 282
158. Angioni A., Barra A., Russo M.T., Coroneo V., Dessi S., and Cabras P. J. Agric. Food Chem. 51 (2003) 3073-3078
159. Barrero A.F., Quilez del Moral J.F., Herrador M.M., Akssira M., Bennamara A., Akkad S., and Aitigri M. Phytochemistry 65 (2004) 2507-2515
160. Wijeratne E.M.K., Liu M.X., Kantipudi N.B., Brochini C.B., Gunatilaka A.A.L., and Canfield L.M. Bioorg. Med. Chem. 14 (2006) 7875-7879
161. H. Takayama, S. Yamada, K. Nakayama, T. Suda, Vitamin D3 derivatives, European Patent EP 81793 A1 19830622, Application EP 82-111302 19821207, 1983, 11 pp.
162. H. Takayama, Jpn. Kokai Tokkyo Koho, Japanese Patent JP 58032823 A2 19830225 Showa, 1983, 4 pp.
163. Sheu J.H., Wang G.H., Sung P.J., Chiu Y.H., and Duh C.Y. Planta Med. 63 (1997) 571-572
164. Lo J.M., Wang W.L., Chiang Y.M., and Chen C.M. J. Chin. Chem. Soc. 48 (2001) 821-826
165. Guyot M., Morel E., and Belaud C. J. Chem. Res. Synop. 8 (1983) 188-189
166. Sheu J.H., Liaw C.-C., and Duh C.-Y. J. Nat. Prod. 58 (1995) 1521-1526
167. Lee D., Cuendet M., Axelrod F., Cahvez P.I., Fong H.H.S., Pezzuto J.M., and Kinghorn A.D. Tetrahedron 57 (2001) 7107-7112
168. Sheu J.-H., Huang S.-Y., and Duh C.-Y. Cytotoxic oxygenated desmosterols of the red alga Galaxaura marginata. J. Nat. Prod. 59 (1996) 23-26
169. Sheu J.-H., Huang S.-Y., Wang G.-H., and Duh C.-Y. J. Nat. Prod. 60 (1997) 900-903
170. Sheu J.H., Wang G.H., Sung P.J., and Duh C.-Y. J. Nat. Prod., 62 (1999) 224-247
171. Jung B.S., and Shin M.K. Hyang-Yak (Saeng-Yak) Dae-Sa-Jeon (1990), Young Lim Publications, Seoul pp. 380-381
172. Park J.G., Hyun J.W., Lim K.H., Shin J.E., Won Y.J., Yi Y.D., Shin K.H., and Chang I.M. Korean J. Pharmacog. 24 (1993) 223-230
173. Kitts D.D., and Lim K.-T. J. Toxicol. Environ. Health 64A (2001) 357-371
174. Lee I.S., Oh S.R., Ahn K.S., and Lee H.K. Chem. Pharm. Bull. 49 (2001) 1024-1026
175. Ruecker G., Manns D., Schenkel E.P., Hartmann R., and Heinzmann B.M. Arch. Pharm. (Weinheim) 336 (2003) 205-207
176. Takaishi Y., Uda M., Ohashi T., Nakano K., Murakami K., and Tommiatsu T. Phytochemistry 30 (1991) 4117-4120
177. Matsueda S., Shimoyama M., Imaizumi T., and Tsushima Y. Yakugaku Zasshi 102 (1982) 347-351
178. Kahlos K., Kangas L., and Hiltunen R. Planta Med. 55 (1989) 389-390
179. Kuo Y.C., Wenig S.C., Chou C.J., Chang T.T., and Tsai W.J. Br. J. Pharmacol. 140 (2003) 895-906
180. Im K.S., Nam K.I., Sim C.J., and Jung J.H. Saengyak Hakhoechi 31 (2000) 401-406
181. Nam K.S., Jo Y.S., Kim Y.H., Hyun J.W., and Kim H.W. Life Sci. 69 (2001) 229-237
182. Lee S.H., Shim S.H., Kim J.S., and Kang S.S. Arch. Pharm. Res. 29 (2006) 479-483
183. Macias F.A., Chinchilla N., Varela R.M., and Molinillo J.M. Steroids 71 (2006) 603-608
184. Takei T., Yoshida M., Ohnishi-Kameyama M., and Kobori M. Biosci. Biotechnol. Biochem. 69 (2005) 212-215
185. Bok J.W., Lermer L., Chilton J., Klingeman H.G., and Towers G.H.N. Phytochemistry 51 (1999) 891-898
186. Iwashima M., Terada I., Iguchi K., and Yamori T. Chem. Pharm. Bull. 50 (2002) 1286-1289
187. Sheu J.-H., Chang K.-C., and Duh C.-Y. J. Nat. Prod. 63 (2000) 149-151
188. Gonzalez C., Pareja A., Marquez M.E., Marquez D.M., Martinez A., and Higuita E. Acta Farmaceutica Bonaerense (Colombia) 24 (2005) 75-79
189. Gauvin A., Smadja J., Aknin M., Faure R., and Gaydou E.-M. Canadian J. Chem. 78 (2000) 986-992
190. Kobori M., Yoshida M., Ohnishi-Kameyama M., Takei T., and Shinmoto H. Biol. Pharm. Bull. 29 (2006) 755-759
191. Lin C.N., Tome W.P., and Won S.J. J. Nat. Prod. 54 (1991) 998-1002
192. Hamzah S., and Yusof A. Br. J. Sports Med. 37 (2003) 464-470
193. Itokawa H., Kishi E., Morita H., Takeya K., and Iitaka Y. Chem. Lett. (1991) 2221-2222
194. Morita H., Kishi E., Takeya K., Itokawa H., and Iitaka Y. Phytochemistry 34 (1993) 765-771
195. Ruecker G., Manns D., Hartmann R., and Bonsels U. Arch. Pharm. (Weinheim) 328 (1995) 725-730
196. Chatterjee S.S., Noldner M., Koch E., and Erdelmeier C. Pharmacopsychiatry 31 (1998) 7-15
197. Koch E., and Chatterjee S.S. Pharmacopsychiatry 34 Suppl. 1 (2001) S70-S73
198. Shen Y.C., Prakash C.V.S., and Guh J.-H. Tetrahedron Lett. 45 (2004) 2463-2465
199. Patel M., Horan A.C., Gullo V.P., Loebenberg D., Marquez J.A., Miller G.H., and Waitz J.A. J. Antibiot. 37 (1984) 413-415
200. Wright J.J.K., Merill Y., Puar M.S., and McPhail A.T. J. Chem. Soc. Chem. Commun. 7 (1984) 473-474
201. Takahashi S., Nakano T., Koiwa T., Noshita T., Funayama S., Koshino H., and Nakagawa A. J. Antibiot. (Tokyo) 53 (2000) 163-170
202. Nakano T., Koiwa T., Takahashi S., and Nakagawa A. J. Antibiot. (Tokyo) 53 (2000) 12-18
203. Chen W.S., Chen Y.T., Wan X.Y., Friedrichs E., Puff H., and Breitmaier E. Liebigs Ann. Chem. 10 (1981) 1880-1885
204. Zhenjun D., and Lown J.W. Photochem. Photobiol. 52 (1990) 609-616
205. Fang L.Z., Qing C., Shao H.J., Yang Y.D., Dong Z.J., Wang F., Zhao W., Yang W.Q., and Liu J.K. J. Antibiot. (Tokyo) 59 (2006) 351-354
206. Shen Y., Rong X., and Gao Z. Zhongguo 27 (2002) 674-676
207. Kishi T., Tahara S., Taniguchi N., Tsuda M., Tanaka C., and Takahashi S. Planta Med. 57 (1991) 376-379
208. Diwu Z. Photochem. Photobiol. 61 (1995) 529-539
209. Diwu Z., Zhang C., and Lown J.W. Anticancer Drug 8 (1993) 129-143
210. Hudson J.B., Zhou J., Chen J., Harris L., Yip L., and Towers G.H.N. Photochem. Photobiol. 60 (1994) 253-255
211. Diwu Z., and Lown J.W. J. Photochem. Photobiol. 18B (1993) 145-154
212. Jegorov A., Matha V., Sedmera P., Havlicek V., Stuchlik J., Seidel P., and Simek P. Phytochemistry 38 (1995) 403-407
213. Matha V., Jegorov A., Weiser J., and Pillai J.S. Cytobios 69 (1992) 163-170
214. Sedmera P., Havlicek V., Jegorov A., and Segre A.L. Tetrahedron Lett. 36 (1995) 6953-6956
215. Uramoto M., Tanabe M., Hirotsu K., and Clardy J. Heterocycles 17 (1982) 349-354
216. Yamazaki M. Seikagaku 61 (1989) 207-210
217. Eickman N., Clardy J., Cole R.J., and Kirksey J.W. Tetrahedron Lett. 12 (1975) 1051-1054
218. Bunger J., Westphal G., Monnich A., Hinnendahl B., Hallier E., and Muller M. Toxicology 202 (2004) 199-211
219. Chavasiri W. Tetrahedron Lett. 44 (2003) 6759-6761
220. Nassi L., Epe B., Schiffmann D., Adam W., Beinhauer A., and Griesbeck A. Carcinogenesis 8 (1987) 947-953
221. Emmanouilidou E., Ioannou P.C., Christopoulos T.K., and Polizois K. Anal. Biochem. 313 (2003) 97-105
222. Sugii M., Ohkita M., Taniguchi M., Baba K., Kawai Y., Tahara C., Takaoka M., and Matsumura Y. Biol. Pharm. Bull. 28 (2005) 607-610
223. Fujita T., Sakuma S., Sumiya T., Nishida H., Fujimoto Y., Baba K., and Kozawa M. Res. Commun. Chem. Pathol. Pharmacol. 77 (1992) 227-240
224. Matsuura M., Kimura Y., Nakata K., Baba K., and Okuda H. Planta Med. 67 (2001) 230-235
225. Baba K., Taniguchi M., and Nakata K. Foods and Food Ingredients (Japan) 178 (1998) 52-60
226. T. Enoki, E. Kobayashi, K. Ogawa, Y. Kudo, M. Tanabe, K. Sugiyama, H. Ohnogi, H. Sagawa, I. Kato, PCT Int. Appl. Japanese Patent WO 2004096198 A1 20041111, 2004, 289 pp.
227. M. Kimura, H. Iwagaki, M. Tsunenaga, and S. Inoue, PCT Int. Appl. Japanese Patent JP 6017 20050330, 2005, 40 pp.
228. K. Hirasawa, Mi. Murakami, Y. Sato, Jpn. Kokai Tokkyo Koho, Japanese Patent JP 63014788 A2 19880121 Showa, 1988, 8 pp.
229. K. Hirasawa, M. Murakami, Y. Sato, Jpn. Kokai Tokkyo Koho, Japanese Patent JP 63014720 A2 19880121 Showa, 1988, 3 pp.
230. Spiteller G. Free Radic. Biol. Med. 41 (2006) 362-387
231. Maccarrone M., Melino G., and Finazzi-Agro A. Cell Death Differ. 8 (2001) 776-784
232. Sandstrom P.A., Pardi D., Tebbey P.W., Dudek R.W., Terrian D.M., Folks T.M., and Buttke T.M. FEBS Lett. 365 (1995) 66-70
233. Hébert M.-J., Takano T., Holthöfer H., and Brady H.R. J. Immunol. 157 (1996) 3105-3115
234. Aoshima H., Satoh T., Sakai N., Yamada M., Enokido Y., Ikeuchi T., and Hatanaka H. Biochim. Biophys. Acta 1345 (1997) 35-42
235. Liberles S.D., and Schreiber S.L. Chem. Biol. 7 (2000) 365-372
236. Miyamoto S., Dupas C., Murota K., and Terao J. Lipids 38 (2003) 641-649
237. Guidarelli A., and Cantoni O. Biochem. J. 366 (2002) 307-314
238. Spiteller G. Ann. N. Y. Acad. Sci. 959 (2002) 30-44
239. Lapenna D., Ciofani G., Bruno C., Pierdomenico S.D., and Cuccurullo F. Br. J. Pharm. 133 (2001) 739-745
240. Castoria R., De Luca C., Fabbri A.A., Passi S., and Fanelli C. J. Toxicol. Toxin Rev. 8 (1989) 349-360
241. Spiteller P., Kern W., Reiner J., and Spiteller G. Biochim. Biophys. Acta 1531 (2001) 188-208
242. Yin H., and Porter N.A. Antioxid. Redox Signal. 7 (2005) 170-184
243. Medina-Navarro R., Duran-Reyes G., and Hicks J.J. Endocr. Res. 25 (1999) 263-280
244. Griveau J.F., Dumont E., Renard P., Callegari J.P., and Le Lannou D. J. Reprod. Fertil. 103 (1995) 17-26
245. Torinuku W., and Miura T. Singlet oxygen and ultraweak chemiluminescence in rat skin. Tohoku J. Exp. Med. 135 (1981) 387-393
246. Cavallini L., Bindoli A., and Macri F. Chem. Biol. Interact. 28 (1979) 139-146
247. Gisler G.C., Diaz J., and Duran N. Physiol. Chem. Phys. 14 (1982) 335-342
248. Di Mascio P., Catalani L.H., and Bechara E.J.H. Free Radic. Biol. Med. 12 (1992) 471-478
249. Hautfenne A., Loncin M., and Paquot C. Oleagineux (Paris) 21 (1966) 303-308
250. Adam W., Andler S., Ballmaier D., Emmert S., Epe B., Grimm G., Mielke K., Moller M., Runger T.M., Saha-Moller C.R., Schonberger A., and Stopper H. Recent Results Cancer Res. 143 (1997) 21-34