Recent advances in the chemistry and biology of natural dimeric quinones

Studies in Natural Products Chemistry

Volumn 46, Issue , 2015, Pages 447-517

  Hussain, Hidayat ^a   Al Harrasi, Ahmed ^a   Green, Ivan R ^b   Hassan, Zahid ^a   Ahmed, Ishtiaq ^c  

^a UNIVERSITY OF NIZWA   (Oman)

^b STELLENBOSCH UNIVERSITY   (South Africa)

^c KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

dimeric quinone chemistry biosynthesis biology

Indexed keywords

EID: 84946183679     PISSN: 15725995     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-444-63462-7.00010-5     Document Type: Chapter

References (347)

1. B.M. Mbala, PhD Thesis, Ghent University, Belgium, 2011.
2. P. Phuwapraisirisan, J. Rangsan, P. Siripong, and S. Tip-Pyang Nat. Prod. Res. 23 2009 1063 1071
3. C.-J. Zheng, C.-L. Shao, Z.-Y. Guo, J.-F. Chen, D.-S. Deng, K.-L. Yang, Y.-Y. Chen, X.-M. Fu, Z.-G. She, and Y.-C. Lin J, Nat. Prod 75 2012 189 197
4. C.-H. Huang, J.-H. Pan, B. Chen, M. Yu, H.-B. Huang, X. Zhu, Y.-J. Lu, Z.-G. She, and Y.-C. Lin Mar. Drugs 9 2011 832 843
5. C. Huang, H. Jin, B. Song, X. Zhu, H. Zhao, J. Cai, Y. Lu, B. Chen, and Y. Lin Appl. Microbiol. Biotechnol. 93 2012 777 785
6. K. Kitagiri, and S. Nishiyama Ann. Rep. Shionogi Res. Lab. 19 1969 63 65
7. S. Matsuura, O. Shiratori, Y. Harada, and K. Katagiri Ann. Rep. Shionogi Res. Lab. 19 1969 66 72
8. H. Kanzaki, G. Kawabat, A. Kobayashi, and K. Kawazu Biosic. Biotech. Biochem. 57 1993 2104 2106
9. N.R. Ferrigni, J.E. Putnam, B. Anderson, L.B. Jacobson, D.E. Nichols, D.S. Moore, and J.L. Maclaughlin J. Nat. Prod. 45 1982 679 686
10. K.D. Beattie, D.R. Thompson, E. Tiralongo, D. Ratkowsky, T.W. May, and M. Gill Tetrahedron Lett. 52 2011 5448 5451
11. N. Li, J. Xu, X. Li, and P. Zhang Fitoterapia 84 2013 85 88
12. A. Debbab, A.H. Aly, R. Edrada-Ebel, V. Wray, W.E.G. Muller, F. Totzke, U. Zirrgiebel, C. Schachtele, M.H.G. Kubbutat, W. Han Lin, M. Mosaddak, A. Hakiki, P. Proksch, and R. Ebel J. Nat. Prod. 72 2009 626 631
13. R. Salazar, V. Rivas, G. González, and N. Waksman Fitoterapia 77 2006 398 400
14. M. Tsaffack, J.R. Nguemeving, V. Kuete, B.S.N. Tchize, P. Mkounga, V.P. Beng, P.G. Hultin, E. Tsamo, and A.E. Nkengfack Chem. Pharm. Bull. 57 2009 1113 1118
15. K.C. Nicolaou, Y.H. Lim, and J. Becker Angew. Chem. Int. Ed. 48 2009 3444 3448
16. A.M. Socha, D. Garcia, R. Sheffer, and D.C. Rowley J. Nat. Prod. 69 2006 1070 1073
17. A.M. Socha, K.L. LaPlante, and D.C. Rowley Bioorg. Med. Chem. 14 2006 8446 8454
18. A. Piñeyro-López, L. Martínez, and R. González Toxicology 92 1994 217 227
19. J. Sepúlveda-Saavedra, I.J. Van der Klei, I. Keizer, A. Piñeyro-López, W. Harder, and M. Veenhuis FEMS Microbiol. Lett. 91 1992 207 212
20. R. Salazar-Aranda, J. Sepúlveda-Saavedra, N. Waksman de Torres, A. Piñeyro-López, and M. Moreno-Sepúlveda FEMS Microbiol Lett. 158 1998 255 260
21. K.H. Shin, W.S. Woo, S.S. Lim, C.S. Shim, H.S. Chung, E.J. Kennelly, and A.D. Kinghorn J. Nat. Prod. 60 1997 1180 1182
22. G. Bringmann, J. Mutanyatta-Comar, K. Maksimenka, J.M. Wanjohi, M. Heydenreich, R. Brun, W.E.G. Mueller, M.G. Peter, J.O. Midiwo, and A. Yenesew Chem. Eur. J. 14 2008 1420 1429
23. A.A. Wube, F. Bucar, K. Asres, S. Gibbons, L. Rattray, and S.L. Croft Phytother. Res. 19 2005 472 476
24. T.J. Dougherty, C.J. Gomer, B.W. Henderson, G. Jori, D. Kessel, M. Korbelik, J. Moan, and Q. Peng J. Natl. Cancer Inst. 90 1998 889 905
25. D.E. Dolmans, D. Fukumara, and R.K. Jain Nat. Rev. Cancer 3 2003 380 387
26. M.R. Hamblin, and T. Hasan Photochem. Photobiol. Sci. 3 2004 436 450
27. S. Yano, S. Hirohara, M. Obata, Y. Hagiya, S. Ogura, A. Ikeda, H. Kataoka, M. Tanaka, and T. Joh J. Photochem. Photobiol. C 12 2011 46 67
28. S. Braese, F. Gläser, G. Kramer, S. Lindner, A.M. Linsenmeier, K.S. Masters, A.C. Meister, B.M. Ruff, and S. Zhong The Chemistry of Mycotoxins, Progress in the Chemistry of Organic Natural Products 2013 Springer-Verlag Wien Vienna
29. S. Sagar, M. Kaur, K.P. Minneman, and V.B. Bajic Eur. J. Med. Chem. 45 2010 3519 3530
30. B. Hazra, P. Sur, D.K. Roy, and A. Banerjee Planta Med. 51 1984 295 297
31. B. Hazra, S. Pal, R. Ghosh, and A. Banerjee Med. Sci. Res. 22 1994 621 623
32. B. Hazra, B. Kumar, S. Biswas, B.N. Pandey, and K.P. Mishra Toxicol. Lett. 157 2005 109 117
33. C.Y. Ting, C.T. Hsu, H.T. Hsu, J.S. Su, T.Y. Chen, W.Y. Tarn, Y.H. Kuo, J. Whang-Peng, L.F. Liu, and J. Hwang Biochem. Pharmacol. 66 2003 1981 1991
34. V. Yardley, D. Snowdon, S. Croft, and B. Hazra Phytother. Res. 10 1996 559 562
35. B. Hazra, R. Ghosh, A. Banerjee, G.C. Kirby, D.C. Warhurst, and J.D. Phillipson Phytother. Res. 9 1995 72 74
36. G.K. Poch, and J.B. Gloer J. Nat. Prod. 55 1992 1093 1099
37. S. Ray, B. Hazra, B. Mittra, A. Das, and H.K. Majumder Mol. Pharmacol. 54 1998 994 999
38. A.A. Wube, B. Streit, S. Gibbons, K. Asres, and F. Bucar J. Ethnopharmacol. 102 2005 191 196
39. K. Ishiguro, H. Oku, and T. Kato Phytother. Res. 14 2000 54 56
40. H. Oku, K. Ishiguro, and T. Kato Biol. Pharm. Bull. 25 2002 137 139
41. K.C. Nicolaou, Y.H. Lim, J.L. Piper, and C.D. Papageorgiou J. Am. Chem. Soc. 129 2007 4001 4013
42. K.C. Nicolaou, Y.H. Lim, C.D. Papageorgiou, and J.L. Piper Angew. Chem. 117 2005 8131 8135
43. E.E. Podlesny, and M.C. Kozlowski Org. Lett. 14 2012 1408 1411
44. E.E. Podlesny, and M.C. Kozlowski J. Org. Chem. 78 2013 466 476
45. F.M. Hauser, and P.J.F. Gauuan Org. Lett. 1 1999 671 672
46. K.C. Nicolaou, J. Becker, Y.H. Lim, A. Lemire, T. Neubauer, and A. Montero J. Am. Chem. Soc. 131 2009 14812 14826
47. Z. Li, Y. Gao, Y. Tang, M. Dai, G. Wang, Z. Wang, and Z. Yang Org. Lett. 10 2008 3017 3020
48. S. Govender, E.M. Mmutlane, W.A.L. van Otterlo, and C.B. Koning Org. Biomol. Chem. 5 2007 2433 2440
49. R.A. Fernandes, and S.V. Mulay J. Org. Chem. 75 2010 7029 7032
50. K.C. Nicolaou, and D. Gray Angew. Chem. Int. Ed. 40 2001 761 763
51. K.C. Nicolaou, and D.L.F. Gray J. Am. Chem. Soc. 126 2004 607 612
52. C.L.L. Chai, J.A. Elix, and F.K.E. Moore J. Org. Chem. 71 2006 992 1001
53. M. Yoshida, and K. Mori Eur. J. Org. Chem. 2000 1313 1317
54. R.N. Khanna, P.K. Sharma, and R.H. Thomson J. Chem. Soc. Perkin Trans. 1 1987 1821 1824
55. J.-P. Lumb, and D. Trauner Org. Lett. 7 2005 5865 5868
56. G. Bringmann, C. Günther, M. Ochse, O. Schupp, and S. Tasler Prog. Chem. Org. Nat. Prod. 82 2001 1 249
57. S. Braese, A. Encinas, J. Keck, and C.F. Nising Chem. Rev. 109 2009 3903 3990
58. B.H. Howard, and H. Raistrick Biochem. J. 56 1954 56 65
59. B.H. Howard, and H. Raistrick Biochem. J. 57 1954 212 222
60. O. Tanaka Chem. Pharm. Bull. 6 1958 203 206
61. S. Gatenbeck Acta Chem. Scand. 14 1960 102 106
62. N. Takeda, S. Seo, Y. Ogihara, U. Sankawa, I. Iitaka, I. Kitagawa, and S. Shibata Tetrahedron 29 1973 3703 3719
63. O. Tanaka, and C. Kaneko Pharm. Bull. 3 1955 284 286
64. S. Shibata, J. Shoji, A. Ohta, and M. Watanabe Pharm. Bull. 5 1957 380 382
65. S. Natori, F. Sato, and S.I. Udagawa Chem. Pharm. Bull. 13 1965 385 389
66. I. Yosioka, K. Morimoto, K. Murata, H. Yamauchi, and I. Kitagawa Chem. Pharm. Bull. 19 1971 2420 2422
67. R. Huot, and P. Brassard Phytochemistry 11 1972 2879
68. J. Santesson Acta Chem. Scand. 24 1970 3331 3334
69. A. Agusta, K. Ohashi, and H. Shibuya Chem. Pharm. Bull. 54 2006 579 582
70. J. Breen, J.C. Dacre, H. Raistrick, and G. Smith Biochem. J. 60 1955 618 626
71. S. Nakamura, F. Nii, S. Inoue, I. Nakanishi, and M. Shimizu Japan J. Microbiol. 18 1974 1 7
72. H. Yamazaki, N. Koyama, S. Omura, and H. Tomoda Org. Lett. 12 2010 1572 1575
73. Y. Ogihara, N.M. Kobayashi, and S. Shibata Tetrahedron Lett. 9 1968 1881 1886
74. U. Sankawa, S. Seo, N. Kobayashi, Y. Ogihara, and S. Shibata Tetrahedron Lett. 9 1968 5557 5560
75. N. Kobayashi, Y. Iitaka, and S. Shibata Acta Cryst. B26 1970 188 201
76. P. Sedmera, M. Podojil, J. Vokoun, V. Betina, and P. Nemec Folia Microbiol. 23 1978 64 67
77. S.F. Brady, M.P. Singh, J.E. Janso, and J. Clardy Org. Lett. 2 2000 4047 4049
78. H. Ejiri, U. Sankawa, and S. Shibata Phytochemistry 14 1975 277 279
79. A. Wirz, U. Simmen, J. Heilmann, I. Calis, B. Meier, and O. Sticher Phytochemistry 55 2000 941 947
80. M.J. Don, Y.J. Huang, R.L. Huang, and Y.L. Lin Chem. Pharm. Bull. 52 2004 866 869
81. R. Suemitsu, T. Sano, M. Yamamoto, Y. Arimoto, F. Morimatsu, and T. Nabeshima Agric. Biol. Chem. 48 1984 2611 2613
82. R. Suemitsu, T. Ueshima, T. Yamamoto, S. Yanagawase, and C. Alterporriol Phytochemistry 27 1988 3251 3254
83. R. Suemitsu, K. Horiuchi, M. Kubota, and T. Okamatse Phytochemistry 29 1990 1509 1511
84. A. Pretsch, P. Proksch, A. Debbab, Novel Anthraquinone Derivatives, Patent WO/2010/135,759, December 2, 2010.
85. N. Okamura, H. Haraguchi, K. Hashimoto, and A. Yagi Phytochemistry 34 1993 1005 1009
86. J. Lou, L. Fu, Y. Peng, and L. Zhou Molecules 18 2013 5891 5935
87. S. Kanamaru, M. Honma, T. Murakami, T. Tsushima, S. Kudo, K. Tanaka, K.I. Nihei, T. Nehira, and M. Hashimoto Chirality 24 2012 137 146
88. J. Koyama, I. Morita, K. Tagahara, and M. Aqil Phytochemistry 56 2001 849 851
89. J. Koyama, I. Morita, K. Tagahara, M. Ogata, T. Mukainaka, H. Tokuda, and H. Nishino Cancer Lett. 170 2001 15 18
90. J. Koyama, I. Morita, K. Tagahara, J. Bakari, and M. Aqil Chem. Pharm. Bull. 50 2002 1103 1105
91. J.G. Shi, C. Li, Y.P. Zhang, and C.Z. Zhang Chin. Chem. Lett. 11 2000 135
92. C. Li, J.G. Shi, Y.P. Zhang, and C.Z. Zhang J. Nat. Prod. 63 2000 653 656
93. L.Y. Foo, and K.R. Tare Experientia 33 1977 1271 1272
94. D. Mcgrath Geoderma 7 1972 167 176
95. D. McGrath Nature 215 1967 1414
96. D. McGrath Chem. Ind. 42 1970 1353
97. Y. Matsui, and K. Kumada Soil Sci. Plant Nutr. 20 1974 333 341
98. N. Fujitake, J. Azuma, T. Hamasaki, H. Nakajima, and K. Saiki Geoderma 48 1991 83 91
99. N. Fujitake, J. Azuma, and T. Hamasaki Soil Sci. Plant Nutr. 37 1991 619 627
100. N. Fujitake, T. Suzuki, M. Fukumoto, and Y. Oji J. Nat. Prod. 61 1998 189 192
101. K. Gluchoff, N. Arpin, M.-P. Dangy-Caye, P. Lebreton, W. Steglich, E. Topper, H. Porurrat, F. Regerat, and D. Deruaz Compt. Rend. 274 1972 1739 1742
102. W. Steglich, E.Z. Topfer-Petersen, W. Reininger, K. Gluchoff, and N. Arpin Phytochemistry 11 1972 3299 3304
103. A.G. Gonza'lez, R. Freire, R. Herna'ndez, J.A. Salazar, and E. Suarez Chem. Ind. 1973 851 852
104. A. Ulubelen, and E. Tuzlaci Phytochemistry 24 1985 2923 2924
105. A. Ulubelen, B. Terem, and E. Tuzlaci Fitoterapia 59 1988 159
106. A. Ulubelen, E. Tuzlaci, and N. Atilan Phytochemistry 28 1989 649 650
107. M. Gill Nat. Prod. Rep. 11 1994 67 90
108. T. Rezanka, and V.M. Dembitsky Nat. Prod. Res. 20 2006 969 980
109. S.C. Nunez-Montoya, A.M. Agnese, and J.L. Cabrera J. Nat. Prod. 69 2006 801 803
110. F. Delle-Monache, I.L. D'Albuquerque, A. De Andrade Chiappeta, and J.F. De Mello Phytochemistry 31 1992 259 261
111. W. Steglich, and K.F. Jedtke Z. Naturforsch. 31C 1976 197 198
112. G. Alemayehu, B. Woldeyesus, and B.M. Abegaz Bull. Chem. Soc. Ethiop. 11 1997 25 29
113. G. Alemayehu, B.M. Abegaz, G. Snatzke, and H. Duddeck Phytochemistry 27 1988 3255 3258
114. B.M. Abegaz, M. Bezabeh, G. Alemayehu, and H. Duddeck Phytochemistry 35 1994 465 468
115. G. Alemayehu, and B.M. Abegaz Phytochemistry 41 1996 919 921
116. S. Kitanaka, and M. Takido Phytochemistry 39 1995 717 718
117. H. Kushida, S. Nakajima, T. Koyama, H. Suzuki, K. Ojiri, H. Suda, Antitumoric BE-43472 manufacture with streptomyces, patent JP 08143569, 1996.
118. H. Rahman, B. Austin, W.J. Mitchell, P.C. Morris, D.J. Jamieson, D.R. Adams, A.M. Spragg, and M. Schweizer Mar. Drugs 8 2010 498 518
119. K. Zaman, M.R. Khan, M. Ali, and D.J. Maitland J. Asian Nat. Prod. Res. 13 2011 62 67
120. X. Wei, J.S. Jiang, Z.M. Feng, and P.C. Zhang Chem. Pharm. Bull. 56 2008 1248 1252
121. W. Steglich, and B. Oertel Sydowia 37 1984 284 295
122. M.S. Buchanan, M. Gill, and A. Gimenez Aust. J. Chem. 51 1998 103 109
123. B. Oertel, B.; Dissertation, University of Bonn, 1994.
124. J. Atherton, B.W. Bycroft, P. Roey, and M.F. Wilcox J. Chem. Soc. C 1968 2560
125. M. Gill, W. Steglich, in: W. Herz, H. Grisebach, G.W. Kirby (Eds.), Progress in the Chemistry of Organic Natural Products, Springer, Vienna, 1987, vol. 51, pp. 125-174.
126. G. Billen, U. Karl, T. Scholl, K.D. Stroech, W. Steglich, in: Atta-ur-Rahman, P.W. Le Quesne, (Eds.) Natural Products Chemistry III, Springer, Berlin, 1988, p. 305.
127. M. Gill, A. Gimenez, A.G. Jhingran, and A.R. Palfreyman Aust. J. Chem. 43 1990 1475 1478
128. M. Gill, A. Gimenez, A.G. Jhingran, and A.R. Palfreyman Tetrahedron Asymmetr. 1 1990 621 634
129. R. Bara, I. Zerfass, A.H. Aly, H.G. Gecke, V. Raghavan, P. Sass, A. Mándi, V. Wray, P.L. Polavarapu, A. Pretsch, W.H. Lin, T. Kurtán, A. Debbab, H. Brötz-Oesterhelt, and P. Proksch J. Med. Chem. 56 2013 3257 3272
130. M. Gill, A. Gimenez, and R.W. McKenzie J. Nat. Prod. 51 1988 1251 1256
131. M. Gill, and A. Gimenez Phytochemistry 30 1991 951 955
132. P.M. Morgan, BSc. (Honours) Thesis, University of Melbourne, 1992.
133. Gimenez A., PhD. Thesis, University of Melbourne, 1990.
134. A.R. Palfreyman, BSc. (Honours) Thesis, University of Melbourne, 1989.
135. B. Gasparini Aust. Mycol. 20 2001 87 91
136. J.M. Wanjohi, A. Yenesew, J.O. Midiwo, M. Heydenreich, M.G. Peter, M. Dreyer, M. Reichert, and G. Bringmann Tetrahedron 61 2005 2667 2674
137. A. Yenesew, J.A. Ogur, and H. Duddeck Phytochemistry 34 1993 1442 1444
138. V. Rivas, G. Cuevas, L. Garza, and N. Waksman ARKIVOC xii 2005 224 233
139. L. Pérez, V. Rivas-Galindo, R. Ramírez-Durón, A. Piñeyro-López, and N. Waksman Ciencia UANL VI 2 2003 196
140. A. Pérez, R. Ramírez-Durón, A. Piñeyro-López, N. Waksman, M. Reichert, and G. Bringmann Tetrahedron 60 2004 8547 8552
141. N. Waksman, and R. Ramirez Rev. Latinoam Quim. 23 1992 25 27
142. V. Rivas, and N. Waksman Nat. Prod. Lett. 15 2001 243 251
143. N. Waksman, G. Benavides, and V. Rivas Phytochemistry 50 1999 1041 1046
144. R. Lanzetta, M. Parrilli, M. Adinolfi, T. Aquila, and M.M. Corsaro Tetrahedron 46 1990 1287 1294
145. G. Alemayehu, B. Abegaz, G. Snatzke, and H. Duddeck Phytochemistry 32 1993 1273 1277
146. E. Dagne, E. Berhanu, and W. Steglich Bull. Chem. Soc. Ethiop. 1 1987 32 35
147. M. Endo, and H. Naoki Tetrahedron 36 1980 2449 2452
148. S. Kitanaka, and M. Takido Chem. Phram. Bull. 37 1989 511 512
149. G. Alemayehu, A. Hailu, and B.M. Abega Phytochemistry 42 1996 1423 1425
150. A.A. El-Gamal, K. Takeya, H. Itokawa, A.F. Halim, M.M. Amer, H.E.A. Saad, and S.A. Awad Phytochemistry 40 1995 245 251
151. Q.Y. Yang, C.S. Yao, and W.S. Fang Fitoterapia 81 2010 59 62
152. K.A. Shaaban, M. Shaaban, I. Grün-Wollny, A. Maier, H.H. Fiebig, and H. Laatsch J. Nat. Prod. 70 2007 1545 1550
153. N. Tsuji, and K. Nagashima Tetrahedron 27 1971 1557 1563
154. N. Tsuji Tetrahedron 24 1968 1765 1776
155. N. Tsuji, and K. Nagashima Tetrahedron 24 1968 4233 4247
156. N. Tsuji, and K. Nagashima Tetrahedron 25 1969 2999 3005
157. N. Tsuji, and K. Nagashima Tetrahedron 27 1971 5719 5729
158. N. Tsuji, and K. Nagashima Tetrahedron 25 1969 3017 3031
159. N. Tsuji, and K. Nagashima Tetrahedron 26 1970 5201 5213
160. N. Tsuji, and K. Nagashima Tetrahedron 25 1969 3007 3015
161. F. Eilbert, H. Anke, and O. Sterner J. Antibiot. 53 2000 1123 1129
162. H. Dave, and L. Ledwani Indian J. Nat. Prod. Res. 3 2012 291 319
163. M. Gill Nat. Prod. Rep. 16 1999 301 317
164. M.A. Brimble, L.J. Duncalf, and M.R. Nairn Nat. Prod. Rep. 16 1999 267 281
165. M. Gill Nat. Prod. Rep. 13 1996 513 528
166. M.S. Buchanan, M. Gill, and J. Yu J. Chem. Soc. Perkin Trans. 1 1997 919 926
167. M.S. Buchanan, M. Gill, and J. Yu Aust. J. Chem. 50 1997 1081 1090
168. H. Brockmann, and H. Pini Naturwissenschaften 34 1947 190
169. H. Brockmann, H. Pini, and O. von Plotho Chem. Ber. 83 1950 161 167
170. S. Horinouchi, O. Hara, and T. Beppu J. Bacteriol. 155 1983 1238 1248
171. S. Horinouchi, and T. Beppu Agric. Biol. Chem. 48 1984 2131 2133
172. H. Brockmann, and V. Loeschcke Chem. Ber. 88 1955 778 788
173. H. Brockmann, and E. Hieronymus Chem. Ber. 88 1955 1379 1390
174. H. Brockmann, A. Zeeck, K. van der Merwe, and W. Mueller Justus Liebigs Ann. Chem. 698 1966 209 229
175. H. Brockmann, W. Mueller, and K. van der Merwe Naturwissenschaften 49 1962 131
176. H. Brockmann, and K. van der Merwe Naturwissenschaften 49 1962 130
177. B. Krone, and A. Zeeck Liebigs Ann. Chem. 1983 510 518
178. C.P. Gorst-Allman, B.A.M. Rudd, C.-J. Chang, and H.G. Floss J. Org. Chem. 46 1981 455 456
179. B. Krone, and A. Zeeck Liebigs Ann. Chem. 1987 751 758
180. A. Zeeck, and P. Christiansten Justus Liebigs Ann. Chem. 724 1969 172 182
181. H. Brockmann, and A. Zeeck Chem. Ber. 101 1968 4221 4229
182. R.A. Nelson, J.A. Pope Jr., G.M. Luedemann, L.E. McDaniel, and C.P. Schaffner J. Antibiot. 39 1986 335 344
183. D. Ling, L.S. Shield, and K.L. Reinhart Jr. J. Antibiot. 39 1986 345 353
184. W.L. Russell, R.C. Pandey, C.P. Schaffner, and H.M. Fales J. Antibiot. 41 1988 149 156
185. R.A. Nelson, J.A. Pope Jr., R.C. Pandey, L.E. McDaniel, C.P. Schaffner, R.L. Beveridge, P.H. Hoops, and F. Jorden J. Antibiot 41 1988 1659 1667
186. S.R. Jammula, S.B. Pepalla, H. Telikepalli, K.V.J. Rao, and R.H. Thomson Phytochemistry 30 1991 3741 3744
187. J.P.E. Human, A.W. Johnston, S.F. MacDonald, and A.R. Todd J. Chem. Soc. 1950 477 485
188. H. Duewell, A.W. Johnston, S.F. MacDonald, and A.R. Todd J. Chem. Soc. 1950 485 490
189. B.R. Brown, T. Ekstrand, A.W. Johnston, S.F. MacDonald, and A.R. Todd J. Chem. Soc. 1952 4925 4928
190. H.J. Banks, and D.W. Cameron Aust. J. Chem. 25 1972 2199 2207
191. K.S. Brown Jr. Chem. Soc. Rev. 4 1975 263 288
192. J.H. Bowie, and D.W. Cameron J. Chem. Soc. (C) 1967 708 711
193. J.H. Bowie, and D.W. Cameron J. Chem. Soc. (C) 1967 720 723
194. H. Brockmann, and P. Christiansen Chem. Ber. 103 1970 708 717
195. A. Zeeck, and M. Mardin Justus Liebigs Ann. Chem. 1974 1063 1099
196. B. Krone, and A. Zeeck Liebigs Ann. Chem. 1983 471 502
197. M. Horikawa, T. Hashimoto, Y. Asakawa, S. Takaoka, M. Tanaka, H. Kaku, T. Nishii, K. Yamaguchi, H. Masu, M. Kawase, S. Suzuki, M. Sato, and T. Tsunoda Tetrahedron 62 2006 9072 9076
198. R.S. Kapil, and M.M. Dhar J. Sci. Industr. Res. 20B 1961 498 500
199. A.K. Ganguly, and T.R. Govindachari Tetrahedron Lett. 7 1966 3373 3376
200. G.S. Sidhu, and M. Pardhasaradhi Tetrahedron Lett. 8 1967 1313 1316
201. G.S. Sidhu, and M. Pardhasaradhi Indian J. Chem. 8 1970 569 571
202. W.T. Harrison, and O.C. Musgrave Acta Crystallogr. C 60 2004 399 401
203. T.J. Lillie, O.C. Musgrave, and D. Skoyles J. Chem. Soc. Perkin Trans. 1 1976 2155 2161
204. J.A.D. Jeffreys, M.B. Zakaria, and P.G. Waterman Phytochemistry 22 1983 1832 1833
205. S.-M. Zhong, P.G. Waterman, and J.A.D. Jeffreys Phytochemistry 23 1984 1067 1072
206. M.A. Ferreira, M.A.C. Costa, A.C. Alves, and M. Helena Phytochemistry 13 1974 1587 1589
207. L.M. van der Vijver, and K.W. Gerritsma Phytochemistry 13 1974 2322 2323
208. B.A. Adeniyi, H.H. Fong, J.M. Pezzuto, L. Luyengi, and H.A. Odelola Phytother. Res. 14 2000 112 117
209. A.C. Alves, M.A. Costa, and M.I. Paul Planta Med. 47 1983 121 124
210. S. Ganapaty, P.S. Thomas, S. Fotso, and H. Laatsch Phytochemistry 65 2004 1265 1271
211. S. Ganapaty, P.S. Thomas, G. Karagianis, and P.G. Waterman Nat. Prod. Res. 20 2006 783 787
212. A. Joubert, F. van der Kooy, J.J.M. Meyer, and N. Lall Chromatographia 64 2006 399 403
213. L.T. Byrne, S.M. Colegate, P.R. Dorling, and C.R. Huxtable Aust. J. Chem. 40 1987 1315 1320
214. A.R. Jassbi, P. Singh, S. Jain, and S. Tahara Helv. Chim. Acta 87 2004 820 824
215. X.B. Xiao, Y.X. Lin, G.B. Xu, X.B. Gong, Y. Gu, J.F. Tong, and J. Yang Helv. Chim. Acta 94 2011 404 409
216. K. Mori-Yasumoto, R. Izumoto, H. Fuchino, T. Ooi, Y. Agatsuma, T. Kusumi, M. Satake, and S. Sekita Bioorg. Med. Chem. 20 2012 5215 5219
217. H. Liu, Y.S. Jin, Y. Song, X.N. Yang, X.W. Yang, D.S. Geng, and H.S. Chen J. Asian Nat. Prod. Res. 12 2010 286 292
218. T.L.G. Lemos, S.M.O. Costa, O.D.L. Pessoa, and R. Braz-Filho Magn. Reson. Chem. 37 1999 908 911
219. L.M.A. Macambira, C.H.S. Andrade, F.J.A. Matos, and A.A. Craveiro Cienc. Cult. Supl. 37 1985 502 507
220. P.K. Sharma, R.N. Khanna, B.K. Rohatgi, and R.H. Thomsom Phytochemistry 27 1988 632 633
221. J.C. Krishna, and P.G. Singh Ind. J. Chem. 14B 1976 637
222. R. Dayal, and T.R. Seshadri J. Ind. Chem. Soc. 56 1979 940 941
223. A.G. Gonzalez, J.T. Barroso, R.J. Cardona, J.M. Medina, and F. Rodriguezluis Ann. Quim. 73 1977 538 545
224. A.W. Salae, C. Karalai, C. Ponglimanont, A. Kanjana-Opas, and S. Yuenyongsawad Can. J. Chem. 88 2010 922 927
225. A.H. Uc-Cachon, G.M. Molina-Salinas, S. Said-Fernandez, M. Mendez-Gonzalez, M. Caceres-Farfan, and R. Borges-Argaez Nat. Prod. Res. 27 2013 1174 1178
226. A. Correia-Alves, and M.A. Cruz-Costa Tetrahedron Lett. 21 1980 2459 2460
227. B. Adeniyi, M. Robert, H. Chai, and H. Fong Phytother. Res. 17 2003 282 284
228. H. Oku, and K. Ishiguro Biol. Pharm. Bull. 25 2002 658 660
229. S. Ganapaty, P.S. Thomas, B.N. Mallika, S. Balaji, G. Karagianis, and P.G. Waterman Biochem. Syst. Ecol. 33 2005 313 315
230. R.M. Khan, and E. Rwekika Phytochemistry 49 1998 2501 2503
231. J.G. Tangomouo, D. Lonsti, F.N. Ngooumou, V. Kuete, A.L. Meli, R.N. Manfouo, H.W. Kamdem, P. Tane, V.P. Peng, B.L. Sondengam, and J.D. Conolly Bull. Chem. Soc. Ethiop. 19 2005 81 88
232. T.J. Lillie, O.C. Musgrave, and D. Skoyles J. Chem. Soc. Perkin Trans. 1 1976 2546
233. M.A. Ernst-Russell, J.A. Elix, C.L.L. Chai, A.C. Willis, N. Hamada, and T.H. Nash Tetrahedron Lett. 40 1999 6321 6324
234. P. Babula, V. Adam, L. Havel, and R. Kizek Curr. Pharm. Anal. 5 2009 47 68
235. M. Pardhasaradhi, and G.S. Sidhu Tetrahedron Lett. 13 1972 4201 4204
236. M. Pardhasaradhi, and G.S. Sidhu Phytochemistry 18 1979 684 685
237. M. Higa Chem. Pharm. Bull. 36 1988 3234 3236
238. A.R. Mehendale, and R.H. Thomson Phytochemistry 14 1975 801 802
239. P. Panichayupakaranan, H. Noguchi, W. De-Eknamkul, and U. Sankawa Phytochemistry 40 1995 1141 1143
240. H. Itokawa, Z.Z. Ibraheim, Y.F. Qiao, and K. Takeya Chem. Pharm. Bull. 41 1993 1869 1872
241. J.P. Lumb, and D. Trauner J. Am. Chem. Soc. 127 2005 2870 2871
242. Y.F. Qiao, K. Takeya, H. Itokawa, and Y. Iitaka Chem. Pharm. Bull. 38 1990 2896 2898
243. H.Y. Bai, S. Li, F. Yin, and L.H. Hu J. Nat. Prod. 68 2005 1159 1163
244. H.S. Santos, S.M.O. Costa, O.D.L. Pessoa, M.O. Moraes, C. Pessoa, S. Fortier, E.R. Silveira, and T.L.G. Lemos Z. Naturforsch. C Biosci. 58 2003 517 520
245. Z.Z. Ibraheim, and Y.G. Gouda Bull. Pharm. Sci. Assiut Univ. 33 2010 225 233
246. K.O. Eyong, K. Krohn, H. Hussain, G.N. Folefoc, A.E. Nkengfack, B. Schulz, and Q. Hu Chem. Pharm. Bull. 53 2005 616 619
247. K.O. Eyong, G.N. Folefoc, V. Kuete, V.P. Beng, K. Krohn, H. Hussain, A.E. Nkengfack, M. Saeftel, S.R. Sarite, and A. Hoerauf Phytochemistry 67 2006 605 609
248. M. Gill, and A. Gimenez Tetrahedron Lett. 31 1990 3505 3508
249. M. Gill, and A. Gimiinez J. Chem. Soc. Perkin Trans. 1 1995 645 651
250. A.M. Aguinaldo, O.P.M. Ocampo, B.F. Bowden, A.I. Gray, and P.G. Waterman Phytochemistry 33 1993 933 935
251. R. Lacret, R.M. Varela, J.M.G. Molinillo, C. Nogueiras, and F.A. Macías J Chem. Ecol. 37 2011 1341 1348
252. X. Wei, J.S. Jiang, Z.M. Feng, and P.C. Zhang Chin. Chem. Lett. 18 2007 412 414
253. J.O. Midwo, and Y. Ghebremeskel Bull. Chem. Soc. Ethiop. 7 1993 67 90
254. L.O.A. Manguro, J.O. Midiwo, W. Kraus, and I. Ugi Phytochemistry 64 2003 855 862
255. H. Ogawa, and S. Natori Phytochemistry 7 1968 773 782
256. H. Ogawa, and S. Natori Chem. Pharm. Bull. 16 1968 1709 1720
257. H. Ogawa, S. Natori, K. Yoshihira, and S. Natori Tetrahedron Lett. 11 1968 1387 1392
258. Y. Fukuyama, Y. Kiriyama, and M. Kodama Chem. Pharm. Bull. 46 1998 1770 1775
259. L.K. Yang, C. Khoo-Beattie, K.L. Goh, B.L. Chng, K. Yoganathan, Y.H. Lai, and M.S. Butler Phytochemistry 58 2001 1235 1238
260. B.L. Ndonsta, J.S.N. Tatsimo, D. Csupor, P. Forgo, R. Berkecz, A. Berenyi, M. Tene, J. Molnar, I. Zupko, J. Hohmann, and P. Tane Phytochemistry Lett. 4 2011 227 230
261. B.L. Ndontsa, M.F. Tala, F.M. Talontsi, H.K. Wabo, M. Tene, H. Laatsch, and P. Tane Phytochemistry Lett. 5 2012 463 466
262. S. Shibata Pure Appl. Chem. 33 1973 109 128
263. S. Seo, U. Sankawa, Y. Ogihara, Y. Iitaka, and S. Shibata Tetrahedron 29 1973 3721 3726
264. D.-M. Yang, U. Sankawa, Y. Ebizuka, and S. Shibata Tetrahedron 32 1976 333 335
265. U.R. Kalkote, S.R. Ghorpade, S.P. Chavan, and T. Ravindranathan J. Org. Chem. 66 2001 8277 8281
266. C. Hertweck, and W. Boland J. Prakt. Chem. 341 1999 83 87
267. P.K. Jadhav, K.S. Bhat, T. Perumal, and H.C. Brown J. Org. Chem. 51 1986 432 439
268. K.C. Nicolaou, and K.H. Ahn Tetrahedron Lett. 30 1989 1217 1220
269. D.J. Kopecky, and S.D. Rychnovsky J. Am. Chem. Soc. 123 2001 8420 8421
270. X. Li, J. Yang, and M.C. Kozlowski Org. Lett. 3 2001 1137 1140
271. M.C. Kozlowski, X. Li, P.J. Carroll, and Z. Xu Organometallics 21 2002 4513 4522
272. X. Xie, P.-W. Phuan, and M.C. Kozlowski Angew. Chem. Int. Ed. 42 2003 2168 2170
273. C.A. Mulrooney, X. Li, E.S. DiVirgilio, and M.C. Kozlowski J. Am. Chem. Soc. 125 2003 6856 6857
274. X. Li, J.B. Hewgley, C.A. Mulrooney, J. Yang, and M.C. Kozlowski J. Org. Chem. 68 2003 5500 5511
275. B.J. Morgan, X. Xie, P.-W. Phuan, and M.C. Kozlowski J. Org. Chem. 72 2007 6171 6182
276. J.B. Hewgley, S.S. Stahl, and M.C. Kozlowski J. Am. Chem. Soc. 130 2008 12232 12233
277. F. Ullman, and J. Bielecki Chem. Ber. 34 1901 2174 2185
278. G. Bringman, R. Walter, and R. Weirich Angew. Chem. Int. Ed. Engl. 29 1990 977 991
279. P.E. Fanta Synthesis 1974 9 21
280. P.E. Fanta Chem. Rev. 38 1946 139 196
281. F.M. Hauser, R.P. Rhee, S.M. Weinreb, and J.H. Dodd Synthesis 1980 72 74
282. V. Arkley, G.I. Attenburrow, G.I. Gregory, and T. Walker J. Chem. Soc. 1962 1260 1268
283. G.I. Gregory, P.J. Holton, H. Robinson, and T. Walker J. Chem. Soc. 1962 1269 1276
284. B.W. Bycroft, P.J. Holton, J.C. Roberts, J. Chem. Soc., (1963) 4868-4872; F.M. Hauser, D. Sengupta, S.A. Corlett, J. Org. Chem. 59 (1994) 1967-1969.
285. J.A. Marshall, M.M. Yanik, N.D. Adams, K.C. Ellis, and H.R. Chobanian Org. Synth. 81 2005 157
286. S. Nahm, and S.M. Weinreb Tetrahedron Lett. 22 1981 3815 3818
287. M.P. Sibi Org. Prep. Proc. Int. 25 1993 15 40
288. M. Mentzel, and H.M.R. Hoffmann J. Prakt. Chem. 339 1997 517 524
289. J. Singh, N. Satyamurthi, and I.S. Aidhen J. Prakt. Chem. 342 2000 340 347
290. K.C. Nicolaou, D.J. Edmonds, and P.G. Bulger Angew. Chem., Int. Ed. 45 2006 7134 7186
291. L.F. Tietze, G. Brasche, and K. Gericke Domino Reactions in Organic Synthesis 2006 Wiley-VCH Weinheim p 672
292. K.C. Nicolaou, T. Montagnon, and S.A. Snyder Chem. Commun. 2003 551 564
293. J. Tsuji, H. Nagashima, and K. Hori Chem. Lett. 1980 257 260
294. V. Snieckus Chem. Rev 90 1990 879 933
295. S. Danishefsky, R.K. Singh, and R.B. Gammill J. Org. Chem. 43 1978 379 380
296. S. Danishefsky, C.-F. Yan, R.K. Sungh, R.B. Gammill, P.M. McMurry Jr., N. Fritsch, and J. Clardy J. Am. Chem. Soc. 101 1979 7001 7008
297. G.A. Kraus, J. Li, M.S. Gordon, and J.H. Jensen J. Org. Chem. 60 1995 1154 1159
298. M.A. Hossain, S. Lucarini, D. Powell, and K. Bowman-James Inorg. Chem. 43 2004 7275 7277
299. J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, and M. Lemaire Chem. Rev. 102 2002 1359 1469
300. J.C. Anderson, and D.J. Pearson J. Chem. Soc. Perkin Trans. 1 1998 2023 2030
301. H. Gross, A. Rieche, and G. Mattey Chem. Ber. 96 1963 308 313
302. R. Hayakawa, K. Nozawa, K. Kimura, and M. Shimizu Tetrahedron 55 1999 7519 7528
303. K. Mashima, T. Nakamura, Y. Matsuo, and K. Tani J. Organomet. Chem. 607 2000 51 56
304. E.J. Corey, and P.L. Fuchs Tetrahedron Lett. 36 1972 3769 3772
305. G. Delogu, M.A. Dettori, A. Patti, S. Pepotti, and G. Casalone Tetrahedron Asymmetr. 14 2003 2467 2474
306. D.J. Cram, R.A. Carmack, G.M. Lein, I. Goldberg, C.B. Knobler, E.F. Maverick, and K.N. Trueblood J. Am. Chem. Soc. 109 1987 7068 7074
307. E.L. Larghi, and T.S. Kaufman Synthesis 2006 187 220
308. P. Contant, M. Haess, J. Riegl, M. Scalone, and M. Visnick Synthesis 1999 821 828
309. S. Iyer, and L.S. Liebeskind J. Am. Chem. Soc. 109 1987 2759 2770
310. H. Sletter, and H. Kuhlmann Synthesis 1979 29 30
311. C.P. Casey, C.R. Jones, and H. Tukada J. Org. Chem. 46 1981 2089 2092
312. A.R. Martin, and J.F. Caputo J. Org. Chem. 39 1974 1811 1814
313. L. Syper, K. Kloc, J. Mlochowski, and Z. Szulc Synthesis 1979 521 522
314. T. Inaba, I. Umezawa, M. Yuasa, T. Inoue, S. Mihashi, H. Itokawa, and K. Ogura J. Org. Chem. 52 1987 2957 2958
315. C.M. Beaudry, J.P. Malerich, and D. Trauner Chem. Rev. 105 2005 4757 4778
316. L. Guillonneau, D. Taddei, and C.J. Moody Org. Lett. 10 2008 4505 4508
317. B.M. Trost, and R.J. Kulawiec J. Am. Chem. Soc. 115 1993 2027 2036
318. C.R.H.I. DeJong, H.J. Hageman, G. Hoentjen, and W.J. Mus Org. Synth. 6 1988 412 413
319. K.A. Parker, D. Taveras, in Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons Ltd, Chichester, 1995, vol. 6, pp. 4423-4425.
320. Y. Fukuyama, Y. Kiriyama, M. Kodama, H. Iwaki, S. Hosozawa, S. Aki, and K. Matsui Chem. Pharm. Bull. 42 1994 2211 2213
321. U. Sankawa, Y. Ebizuka, and S. Shibata Tetrahedron Lett. 14 1973 2125 2128
322. K. Ohnishi, H. Tanabe, S. Hayashi, and R. Suemitsu Biosci. Biotech. Biochem. 56 1992 42 43
323. K. Ohnishi, R. Suemitsu, M. Kubota, H. Matano, and Y. Yamada Phytochemistry 30 1991 2593 2595
324. D.H. Sherman, M.J. Bibb, T.J. Simpson, D. Johnson, F. Malpartida, M. Fernandez-Moreno, E. Martinez, C.R. Hutchinson, and D.A. Hopwood Tetrahedron 47 1991 6029 6043
325. S. Govender, PhD Thesis, University of the Witwatersrand, South Africa, 2005.
326. J.N. Collie J. Chem. Soc. 91 1907 1806 1813
327. A.J. Birch Science 156 1967 202
328. H.G. Floss, and J.M. Beale Angew. Chem. Int. Ed. Engl. 28 1989 146 177
329. D. O'Hagan Nat. Prod. Rep. 9 1992 447 479
330. K. Kawai, T. Kato, H. Mori, J. Kitamura, and Y. Nozawa Toxicol. Lett. 20 1984 155 160
331. S. Krivobok, F. Seigle-Murandi, R. Steiman, D.R. Marzin, and V. Betina Mut. Res. 279 1992 1 8
332. Y. Yanagi, M. Nakata, and N. Suzuki J. Pest. Sci. 1 1976 107
333. Y. Ueno, K. Uemori, E.-C. Niimi, S.-I. Tanuma, S. Nagata, M. Sugamata, T. Ihara, M. Sekijima, K-i. Kawai, I. Ueno, and F. Tashiro Nat. Toxins 3 1995 129 137
334. F. Vargas, C. Rivas, T. Zoltan, V. López, J. Ortega, C. Izzo, M. Pineda, J. Medina, E. Medina, and L. Rosales Av. Quim. 3 2008 7
335. N. Sato, Y. Ueno, and I. Ueno J. Toxicol. Sci. 2 1977 261
336. Y. Ueno, N. Sato, T. Ito, I. Ueno, M. Enomoto, and H. Tsunoda Preliminary Surveys in Mice J. Toxicol. Sci 5 1980 295 302
337. H. Mori, K. Kawai, F. Ohbayashi, T. Kuniyasu, M. Yamazaki, T. Hamasaki, and G.M. Williams Cancer Res. 44 1984 2918 2923
338. Y. Ueno, I. Ueno, N. Sato, Y. Iitoi, M. Saito, M. Enomoto, and H. Tsunoda Toxicological Jpn. J. Exp. Med. 41 1971 177 178
339. S. Mori, K. Kawai, Y. Nozawa, and Y. Ogihara Nat. Toxins 6 1998 85 90
340. L.R. Comini, S.C. Nunez Montoya, M. Sarmiento, J.L. Cabrera, and G.A. Arguello J. Photochem. Photobiol. A 188 2007 185 191
341. L.R. Comini, S.C. Nunez Montoya, P.L. Paez, G.A. Arguello, I. Albesa, and J.L. Cabrera J. Photochem. Photobiol. B 102 2011 108 114
342. I. Fernandez, L. Comini, A. Nigra, S. Nunez, B. Rumie Vittar, J. Cabrera, and V.A. Rivarola Biocell. 33 2009 A266
343. B. Hazra, P. Sur, A. Banerjee, and D.K. Roy J. Ind. Chem. Soc. 58 1981 627 628
344. R. Hayeshi, S. Mukanganyama, B. Hazra, B. Abegaz, and J. Hasler Phytother. Res. 18 2004 877 883
345. M. Chang, Y.G. Shin, R.B. van Breemen, S.Y. Blond, and J.L. Bolton Biochemistry 40 2001 4811 4820
346. G. Gaudiano, T.H. Koch, M. Lo Bello, M. Nuccetelli, G. Ravagnan, A. Serafino, and P. Sinibaldi-Vallebona Biochem. Pharmacol. 60 2000 1915 1923
347. A.W. Norhanom, and B. Hazra Phytother. Res. 11 1997 588 590