Polyprenylated Phloroglucinols and Xanthones

Biomimetic Organic Synthesis

Volumn 2, Issue , 2011, Pages 433-467

  Dakanali, Marianna ^a   Theodorakis, Emmanuel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Biomimetic synthesis; Caged Garcinia xanthones; Claisen Diels Alder; Polyprenylated phloroglucinols; Polyprenylated xanthones

Indexed keywords

EID: 84885542233     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527634606.ch12     Document Type: Chapter

References (134)

1. Gustafsson, M.H.G., Bittrich, V., and Stevens, P.F. (2002) Int. J. Plant Sci., 163, 1045-1054.
2. Woelk, H. (2000) Br. Med. J., 321, 536-539.
3. Di Carlo, G., Borrelli, F., Ernst, E., and Izzo, A.A. (2001) Trends Pharmacol. Sci., 22, 292-297.
4. Miller, A.L. (1998) Altern. Med. Rev., 3, 18-26.
5. Barnes, J., Anderson, L.A., and Phillipson, J.D. (2001) J. Pharm. Pharmacol., 53, 583-600.
6. Müller, W.E. (2003) Pharmacol. Res., 47, 101-109.
7. Verotta, L. (2002) Phytochem. Rev., 1, 389-407.
8. Rodriguez-Landa, J.F. and Contreras, C.M. (2003) Phytomedicine, 10, 688-699.
9. Medina, M.A., Marti'nez-Poveda, B., Amores-Sa'nchez, M.I., and Quesada, A.R. (2006) Life Sci., 79, 105-111.
10. Ciochina, R. and Grossman, R.B. (2006) Chem. Rev., 106, 3363-3386.
11. Linde, K., Berner, M.M., and Kriston, L. (2008) Cochrane Database Syst. Rev. (Art. No.: CD000448). doi: 10.1002/14651858.CD000448.pub3.
12. Mabberley, D.J. (1997) The Plant-Book: A Portable Dictionary of the Vascular Plants, 2nd edn, Cambridge University Press, New York.
13. Kumar, P. and Baslas, R.K. (1980) Herba Hung., 19, 81-91.
14. Cuesta-Rubio, O., Valez-Castro, H., Frontana-Uribe, B.A., and Cardenas, J. (2001) Phytochemistry, 57, 279-283.
15. Müller, W.E., Singer, A., Wonnemann, M., Hafner, U., Rolli, M., and Schäfer, C. (1998) Pharmacopsychiatry, 31 (Suppl. 1), 16-21.
16. Mennini, T. and Gobbi, M. (2004) Life Sci., 75, 1021-1027.
17. Schempp, C.M., Pelz, K., Wittmer, A., Schöpf, E., and Simon, J.C. (1999) Lancet, 353, 2129.
18. Quiney, C., Billard, C., Salanoubat, C., Fourneron, J.D., and Kolb, J.P. (2006) Leukemia, 20, 1519-1525.
19. Fukuyama, Y., Kuwayama, A., and Minami, H. (1997) Chem. Pharm. Bull., 45, 947-949.
20. Cuesta-Rubio, O., Frontana-Uribe, B.A., Ramirez-Apan, T., and Cardenas, J. (2002) Naturforsch. Teil C, 57, 372-378.
21. Lokvam, J., Braddock, J.F., Reichardt, P.B., and Clausen, T.P. (2000) Phytochemistry, 55, 29-34.
22. Piccinelli, A.L., Cuesta-Rubio, O., China, M.B., Mahmood, N., Pagano, B., Pavone, M., Barone, V., and Rastrelli, L. (2005) Tetrahedron, 61, 8206-8211.
23. Winkelmann, K., Heilmann, J., Zerbe, O., Rali, T., and Sticher, O. (2001) Helv. Chim. Acta, 84, 3380-3392.
24. Weng, J.-R., Tsao, L.-T., Wang, J.-P., Wu, R.-R., and Lin, C.-N. (2004) J. Nat. Prod., 67, 1796-1799.
25. Zuurbier, K.W.M., Fung, S.-Y., Scheffer, J.C., and Verpoorte, R. (1998) Phytochemistry, 49, 2315-2322.
26. Gerhäuser, C. (2005) Eur. J. Cancer, 41, 1941-1954.
27. Adam, P., Arigoni, D., Bacher, A., and Eisenreich, W. (2002) J. Med. Chem., 45, 4786-4793.
28. Drawert, F. and Beier, J. (1974) Phytochemistry, 13, 2149-2155.
29. Drawert, F. and Beier, J. (1976) Phytochemistry, 15, 1693-1694.
30. Drawert, F. and Beier, J. (1976) Phytochemistry, 15, 1695-1696.
31. Klingauf, P., Beuerle, T., Mellenthin, A., El-Moghazy, S.A.M., Boubakir, Z., and Beerhues, L. (2005) Phytochemistry, 66, 139-145.
32. Liu, B., Falkenstein-Paul, H., Schmidt, W., and Beerhues, L. (2003) Plant J., 34, 847-855.
33. Zuurbier, K.W.M., Fung, S.-Y., Scheffer, J.C., and Verpoorte, R. (1995) Phytochemistry, 38, 77-82.
34. Hecht, S., Wungsintaweekul, J., Rohdich, F., Kis, K., Radykewicz, T., Schuhr, C.A., Eisenreich, W., Richter, G., and Bacher, A. (2001) J. Org. Chem., 66, 7770-7775.
35. Eisenreich, W., Rohdich, F., and Bacher, A. (2001) Trends Plant Sci., 6, 78-84.
36. Gabrielsen, M., Rohdich, F., Eisenreich, W., Grawert, T., Hecht, S., Bacher, A., and Hunter, W.N. (2004) Eur. J. Biochem., 271, 3028-3035.
37. Boubakir, Z., Beuerle, T., Benye, L., and Beerhues, L. (2005) Phytochemistry, 66, 51-57.
38. Kuramochi, A., Usuda, H., Yamatsugu, K., Kanai, M., and Shibasaki, M. (2005) J. Am. Chem. Soc., 127, 14200-14201.
39. Siegel, D.R. and Danishefsky, S.J. (2006) J. Am. Chem. Soc., 128, 1048-1049.
40. Ahmad, N.M., Rodeschini, V., Simpkins, N.S., Ward, S.E., and Blake, A.J. (2007) J. Org. Chem., 72, 4803-4815.
41. Tsukano, C., Siegel, D.R., and Danishefsky, S.J. (2007) Angew. Chem. Int. Ed., 46, 8840-8844.
42. Shimizu, Y., Shi, S.-L., Usuda, H., Kanai, M., and Shibasaki, M. (2010) Angew. Chem. Int. Ed., 49, 1103-1106.
43. Rodeschini, V., Ahmad, N.M., and Simpkins, N.S. (2006) Org. Lett., 8, 5283-5285.
44. Nuhant, P., David, M., Pouplin, T., Delpech, B., and Marazano, C. (2007) Org. Lett., 9, 287-289.
45. Qi, J. and Porco, J.A. Jr. (2007) J. Am. Chem. Soc., 129, 12682-12683.
46. Couladouros, E.A., Dakanali, M., Demadis, K.D., and Vidali, V.P. (2009) Org. Lett., 11, 4430-4433.
47. George, J.H., Hesse, M.D., Baldwin, J.E., and Adlington, R.M. (2010) Org. Lett., 12, 3532-3535.
48. Nicolaou, K.C., Pfefferkorn, J.A., Kim, S., and Wei, H.X. (1999) J. Am. Chem. Soc., 121, 4724-4725.
49. Nicolaou, K.C., Pfefferkorn, J.A., Cao, G.-Q., Sanghee, K., and Kessabi, J. (1999) Org. Lett., 1, 807-810.
50. Rodeschini, V., Simpkins, N.S., and Wilson, C. (2007) J. Org. Chem., 72, 4265-4267.
51. Shimizu, Y., Kuramochi, A., Usuda, H., Kanai, M., and Shibasaki, M. (2007) Tetrahedron Lett., 48, 4173-4177.
52. Spessard, S.J. and Stoltz, B.M. (2002) Org. Lett., 4, 1943-1946.
53. Schönwälder, K.-H., Kollatt, P., Stezowski, J.J., and Effenburger, F. (1984) Chem. Ber., 117, 3280-3296.
54. de Oliveira, C.M.A., Porto, A.M., Bittrich, V., Vencato, I., and Marsaioli, A.J. (1996) Tetrahedron Lett., 37, 6427-6430.
55. Abe, M. and Nakada, M. (2007) Tetrahedron Lett., 48, 4873-4877.
56. Abe, M., Saito, A., and Nakada, M. (2010) Tetrahedron Lett., 51, 1298-1302.
57. Kraus, G.A. and Jeon, I. (2008) Tetrahedron Lett., 49, 286-288.
58. Mehta, G. and Bera, M.K. (2009) Tetrahedron Lett., 50, 3519-3522.
59. Mitasev, B. and Porco, J.A. Jr. (2009) Org. Lett., 11, 2285-2288.
60. Takagi, R., Inoue, Y., and Ohkata, K. (2008) J. Org. Chem., 73, 9320-9325.
61. Pouplin, T., Tolon, B., Nuhant, P., Delpech, B., and Marazano, C. (2007) Eur. J. Org. Chem., 5117-5125.
62. Sousa, M.E. and Pinto, M.M.M. (2005) Curr. Med. Chem., 12, 2447-2479.
63. Vieira, L.M.M. and Kijjoa, A. (2005) Curr. Med. Chem., 12, 2413-2446.
64. Silva, A.M.S. and Pinto, D.C.G.A. (2005) Curr. Med. Chem., 12, 2481-2497.
65. Gales, L. and Damas, A.M. (2005) Curr. Med. Chem., 12, 2499-2515.
66. Pinto, M.M.M., Sousa, M.E., and Nascimento, M.S.J. (2005) Curr. Med. Chem., 12, 2517-2538.
67. Riscoe, M., Kelly, J.X., and Winter, R. (2005) Curr. Med. Chem., 12, 2539-2549.
68. Pinto, M.M.M. and Castanheiro, R.A.P. (2009) Curr. Org. Chem., 13, 1215-1240.
69. Pouli, N. and Marakos, P. (2009) Anticancer Agents Med. Chem., 9, 77-98.
70. Han, Q.-B. and Xu, H.-X. (2009) Curr. Med. Chem., 16, 3775-3796.
71. El-Seedi, H.R., El-Ghorab, D.M.H., El-Barbary, M.A., Zayed, M.F., Goransson, U., Larsson, S., and Verpoorte, R. (2009) Curr. Med. Chem., 16, 2581-2626.
72. Sultanbawa, M.U.S. (1980) Tetrahedron, 36, 1465-1506.
73. Ollis, W.D., Ramsay, M.V.J., Sutherland, I.O., and Mongkolsuk, S. (1965) Tetrahedron, 21, 1453-1470.
74. Ahmad, S.A., Rigby, W., and Taylor, R.B. (1966) J. Chem. Soc. (C), 772-779.
75. Leong, Y.-W., Harrison, L.J., Bennett, G.J., and Tan, H.T.-W. (1996) J. Chem. Res. (S), 392-393.
76. Wang, L.L., Li, Z.L., Xu, Y.P., Liu, X.Q., Pei, Y.H., Jing, Y.K., and Hua, H.M. (2008) Chin. Chem. Lett., 19, 1221-1223.
77. Cao, S.-G., Sng, V.H.L., Wu, X.-H., Sim, K.-Y., Tan, B.H.K., Pereira, J.T., and Goh, S.H. (1998) Tetrahedron, 54, 10915-10924.
78. Han, Q.-B., Wang, Y.-L., Yang, L., Tso, T.-F., Qiao, C.-F., Song, J.-Z., Xu, L.-J., Chen, S.-L., Yang, D.-J., and Xu, H.-X. (2006) Chem. Pharm. Bull., 54, 265-267.
79. Tao, S.-J., Guan, S.-H., Wang, W., Lu, Z.-Q., Chen, G.-T., Sha, N., Yue, Q.-X., Liu, X., and Guo, D.-A. (2009) J. Nat. Prod., 72, 117-124.
80. Sukpondma, Y., Rukachaisirikul, V., and Phongpaichit, S. (2005) Chem. Pharm. Bull., 53, 850-852.
81. Asano, J., Chiba, K., Tada, M., and Yoshii, T. (1996) Phytochemistry, 41, 815-820.
82. Nair, P.M. and Venkataraman, K. (1964) Indian J. Chem., 2, 402-404.
83. Lin, L.-J., Lin, L.-Z., Pezzuto, J.M., Cordell, G.A., and Ruangrungsi, N. (1993) Magn. Reson. Chem., 31, 340-347.
84. Thoison, O., Fahy, J., Dumontet, V., Chiaroni, A., Riche, C., van Tri, M., and Sévenet, T. (2000) J. Nat. Prod., 63, 441-446.
85. Thoison, O., Cuong, D.D., Gramain, A., Chiaroni, A., Hung, N.V., and Sévenet, T. (2005) Tetrahedron, 61, 8529-8535.
86. Kosela, S., Cao, S.-G., Wu, X.-H., Vittal, J.J., Sukri, T., Masdianto, M., Goh, S.-H., and Sim, K.-Y. (1999) Tetrahedron Lett., 40, 157-160.
87. Jiangsu New Medical College (1997) Dictionary of Chinese Traditional Medicines, Shanghai Scientific and Technical Publishers, Shanghai.
88. Jinxiang, Y. (1989) Chin. J. Cancer Res., 1, 75-78.
89. Panthong, A., Norkaew, P., Kanjanapothi, D., Taesotikul, T., Anantachoke, N., and Reutrakul, V. (2007) J. Ethnopharmacol., 111, 335-340.
90. Rao, P.L.N. and Verma, S.C.L. (1951) J. Sci. Ind. Res. B, 10, 184-185.
91. Gupta, V.S., Rao, A.V.S.P., and Rao, P.L.N. (1963) Indian J. Exp. Biol., 1, 146-147.
92. Sani, B.P. and Rao, P.L.N. (1966) Indian J. Exp. Biol., 4, 27-28.
93. Santhanam, K. and Rao, P.L.N. (1968) Indian J. Exp. Biol., 6, 158-159.
94. Puttanna, C.R. and Rao, P.L.N. (1968) Indian J. Exp. Biol., 6, 150-152.
95. Santhanam, K. and Rao, P.L.N. (1969) Indian J. Exp. Biol., 7, 34-36.
96. Sani, B.P. and Rao, P.L.N. (1969) Indian J. Chem., 7, 680-684.
97. Verma, S.C.L. and Rao, P.L.N. (1967) Indian J. Exp. Biol., 5, 106-109.
98. Rao, D.R., Gupta, T.R., Gupta, V.S., Rao, K.V.N., and Rao, P.L.N. (1963) Indian J. Chem., 1, 276-277.
99. Batova, A., Lam, T., Wascholowski, V., Yu, A.L., Giannis, A., and Theodorakis, E.A. (2007) Org. Biomol. Chem., 5, 494-500.
100. Chantarasriwong, O., Cho, W.C., Batova, A., Chavasiri, W., Moore, C., Rheingold, A.L., and Theodorakis, E.A. (2009) Org. Biomol. Chem., 7, 4886-4894.
101. Dewick, P.M. (1998) Nat. Prod. Rep., 15, 17-58.
102. Knaggs, A.R. (2003) Nat. Prod. Rep., 20, 119-136.
103. Herrmann, K.M. and Weaver, L.M. (1999) Annu. Rev. Plant Biol., 50, 473-503.
104. Beerhues, L. and Liu, B. (2009) Phytochemistry, 70, 1719-1727.
105. Gottlieb, O.R. (1968) Phytochemistry, 7, 411-421.
106. Dewick, P.M. (2009) Medicinal Natural Products: A Biosynthetic Approach, 3rd edn, John Wiley & Sons, Inc., Hoboken, New Jersey.
107. Locksley, H.D., Moore, I., and Scheinmann, F. (1967) Tetrahedron, 23, 2229-2234.
108. Carpenter, I., Locksley, H.D., and Scheinmann, F. (1969) Phytochemistry, 8, 2013-2025.
109. Bennett, G.J. and Lee, H.-H. (1988) J. Chem. Soc., Chem. Commun., 619-620.
110. Bennett, G.J., Lee, H.-H., and Das, N.P. (1990) J. Chem. Soc., Perkin Trans. I, 2671-2676.
111. Kartha, G., Ramachandran, G.N., Bhat, H.B., Nair, P.M., Raghavan, V.K.V., and Venkataraman, K. (1963) Tetrahedron Lett., 4, 459-472.
112. Quillinan, A.J. and Scheinmann, F. (1971) J. Chem. Soc., Chem. Commun., 966-967.
113. Yemul, S.S. and Rama Rao, A.V. (1974) Org. Mass Spectrom., 9, 1063-1072.
114. Han, Q., Yang, L., Liu, Y., Wang, Y., Qiao, C., Song, J., Xu, L., Yang, D., Chen, S., and Xu, H. (2006) Planta Med., 72, 281-284.
115. Nicolaou, K.C. and Li, J. (2001) Angew. Chem. Int. Ed., 40, 4264-4268.
116. Tisdale, E.J., Slobodov, I., and Theodorakis, E.A. (2003) Org. Biomol. Chem., 1, 4418-4422.
117. Li, N.-G., Wang, J.-X., Liu, X.-R., Lin, C.-J., You, Q.-D., and Guo, Q.-L. (2007) Tetrahedron Lett., 48, 6586-6589.
118. Tisdale, E.J., Slobodov, I., and Theodorakis, E.A. (2004) Proc. Natl. Acad. Sci. U.S.A., 101, 12030-12035.
119. Nicolaou, K.C., Xu, H., and Wartmann, M. (2005) Angew. Chem. Int. Ed., 44, 756-761.
120. Gajewski, J.J. (1980) Acc. Chem. Res., 13, 142-148.
121. Ganem, B. (1996) Angew. Chem. Int. Ed., 35, 936-945.
122. Ganem, B. (1996) Angew. Chem., 108, 1014-1023.
123. Severance, D.L. and Jorgensen, W.L. (1992) J. Am. Chem. Soc., 114, 10966-10968.
124. Gajewski, J.J. (1997) Acc. Chem. Res., 30, 219-225.
125. Tanford, C. (1980) The Hydrophobic Effect, 2nd edn, John Wiley & Sons, Inc., New York.
126. Breslow, R. (2004) Acc. Chem. Res., 37, 471-478.
127. Lindström, U.M. (2002) Chem. Rev., 102, 2751-2772.
128. Grieco, P.A. and Kaufman, M.D. (1999) J. Org. Chem., 64, 6041-6048.
129. Hayden, A.E., Xu, H., Nicolaou, K.C., and Houk, K.N. (2006) Org. Lett., 8, 2989-2992.
130. Nicolaou, K.C., Sasmal, P.K., and Xu, H. (2004) J. Am. Chem. Soc., 126, 5493-5501.
131. Bhamare, N.K., Granger, T., John, C.R., and Yates, P. (1991) Tetrahedron Lett., 32, 4439-4442.
132. Bichan, D.J. and Yates, P. (1972) J. Am. Chem. Soc., 94, 4773-4774.
133. Tisdale, E.J., Chowdhury, C., Vong, B.G., Li, H., and Theodorakis, E.A. (2002) Org. Lett., 4, 909-912.
134. Chantarasriwong, O., Batova, A., Chavasiri, W., and Theodorakis, E.A. (2010) Chem. Eur. J., 16, 9944-9962.