Subcellular Localization and Activity of Gambogic Acid

ChemBioChem

Volumn 13, Issue 8, 2012, Pages 1191-1198

  Guizzunti, Gianni ^b   Batova, Ayse ^a   Chantarasriwong, Oraphin ^a,c   Dakanali, Marianna ^a   Theodorakis, Emmanuel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b INSTITUT PASTEUR   (France)

^c KING MONGKUT'S UNIVERSITY OF TECHNOLOGY THONBURI   (Thailand)

Author keywords

Apoptosis; Caged Garcinia xanthone; Membranes; Mitocan; Mitochondria

Indexed keywords

GAMBOGIC ACID;

APOPTOSIS; ARTICLE; CELL FUNCTION; CELL ORGANELLE; CELL STRUCTURE; CELLULAR DISTRIBUTION; CONTROLLED STUDY; HUMAN; HUMAN CELL; INCUBATION TIME; MITOCHONDRION; PRIORITY JOURNAL;

APOPTOSIS; CELL GROWTH PROCESSES; CELL LINE, TUMOR; HELA CELLS; HUMANS; MITOCHONDRIA; SUBCELLULAR FRACTIONS; XANTHONES;

ANIMALIA; GARCINIA;

EID: 84861451018     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201200065     Document Type: Article

References (85)

1. M. H. G. Gustafsson, V. Bittrich, P. F. Stevens, Int. J. Plant Sci. 2002, 163, 1045-1054;
2. M. U. S. Sultanbawa, Tetrahedron 1980, 36, 1465-1506;
3. P. Kumar, R. K. Baslas, Herba Hung. 1980, 19, 81-91.
4. P. Yates, S. S. Karmarkar, D. Rosenthal, G. H. Stout, V. F. Stout, Tetrahedron Lett. 1963, 4, 1623-1629;
5. A. Anthony, G. R. Desiraju, Supramol. Chem. 2001, 13, 11-23;
6. T. J. R. Weakley, S. X. Cai, H.-Z. Zhang, J. F. W. Keana, J. Chem. Crystallogr. 2001, 31, 501-505.
7. For biosynthetic approaches toward the synthesis of caged Garcinia xanthones see:
8. E. J. Tisdale, I. Slobodov, E. A. Theodorakis, Proc. Natl. Acad. Sci. USA 2004, 101, 12030-12035;
9. K. C. Nicolaou, J. Li, Angew. Chem. 2001, 113, 4394-4398; Angew. Chem. Int. Ed. 2001, 40, 4264-4268;
10. E. J. Tisdale, C. Chowdhury, B. G. Vong, H. Li, E. A. Theodorakis, Org. Lett. 2002, 4, 909-912;
11. K. C. Nicolaou, P. K. Sasmal, H. Xu, K. Namoto, A. Ritzén, Angew. Chem. 2003, 115, 4357-4361; Angew. Chem. Int. Ed. 2003, 42, 4225-4229;
12. E. J. Tisdale, I. Slobodov, E. A. Theodorakis, Org. Biomol. Chem. 2003, 1, 4418-4422;
13. E. J. Tisdale, B. G. Vong, H. Li, S. H. Kim, C. Chowdhury, E. A. Theodorakis, Tetrahedron 2003, 59, 6873-6887.
14. For selected recent reviews on the chemistry and biology of caged Garcinia xanthones see:
15. O. Chantarasriwong, A. Batova, W. Chavasiri, E. A. Theodorakis, Chem. Eur. J. 2010, 16, 9944-9962;
16. N. Pouli, P. Marakos, Anti-Cancer Agents Med. Chem. 2009, 9, 77-98;
17. Q.-B. Han, H.-X. Xu, Curr. Med. Chem. 2009, 16, 3775-3796.
18. J. Asano, K. Chiba, M. Tada, T. Yoshii, Phytochemistry 1996, 41, 815-820;
19. O. Thoison, J. Fahy, V. Dumontet, A. Chiaroni, C. Riche, M. V. Tri, T. Sévenet, J. Nat. Prod. 2000, 63, 441-446;
20. O. Thoison, D. D. Cuong, A. Gramain, A. Chiaroni, N. V. Hung, T. Sévenet, Tetrahedron 2005, 61, 8529-8535;
21. H.-Z. Zhang, S. Kasibhatla, Y. Wang, J. Herich, J. Guastella, B. Tseng, J. Drewe, S. X. Cai, Bioorg. Med. Chem. 2004, 12, 309-317;
22. J. Kuemmerle, S. Jiang, B. Tseng, S. Kasibhatla, J. Drewe, S. X. Cai, Bioorg. Med. Chem. 2008, 16, 4233-4241.
23. A. Batova, T. Lam, V. Wascholowski, A. L. Yu, A. Giannis, E. A. Theodorakis, Org. Biomol. Chem. 2007, 5, 494-500;
24. O. Chantarasriwong, W. C. Cho, A. Batova, W. Chavasiri, C. Moore, A. L. Rheingold, E. A. Theodorakis, Org. Biomol. Chem. 2009, 7, 4886-4894;
25. A. Batova, D. Altomare, O. Chantarasriwong, K. L. Ohlsen, K. E. Creek, Y.-C. Lin, A. Messersmith, A. L. Yu, J. Yu, E. A. Theodorakis, Mol. Cancer Ther. 2010, 9, 2869-2878;
26. G. Guizzunti, E. A. Theodorakis, A. L. Yu, C. Zurzolo, A. Batova, Invest. New Drugs 2011; DOI:
27. L. Qiang, Y. Yang, Q.-D. You, Y.-J. Ma, L. Yang, F.-F. Nie, H.-Y. Gu, L. Zhao, N. Lu, Q. Qi, W. Liu, X.-T. Wang, Q.-L. Guo, Biochem. Pharmacol. 2008, 75, 1083-1092;
28. Y. Yang, L. Yang, Q.-D. You, F.-F. Nie, H.-Y. Gu, L. Zhao, X.-T. Wang, Q.-L. Guo, Cancer Lett. 2007, 256, 259-266;
29. Q. Guo, Q. Qi, Q. You, H. Gu, L. Zhao, Z. Wu, Basic Clin. Pharmacol. Toxicol. 2006, 99, 178-184;
30. L. Zhao, C. Zhen, Z. Wu, R. Hu, C. Zhou, Q. Guo, Drug Chem. Toxicol. 2010, 33, 88-96;
31. K. Hao, X. Q. Liu, G. J. Wang, X. P. Zhao, Eur. J. Drug Metab. Pharmacokinet. 2007, 32, 63-68.
32. Z. T. Zhou, J. W. Wang, Chin. J. New Drugs 2007, 16, 79-82.
33. A. Deorukhkar, S. Krishnan, S. Gautam, B. B. Aggarwal, Expert Opin. Invest. Drugs 2007, 16, 1753-1773;
34. R. Kim, K. Tanabe, Y. Uchida, M. Emi, H. Inoue, T. Toge, Cancer Chemother. Pharmacol. 2002, 50, 343-352.
35. For selected reviews on this topic see:
36. S. Fulda, K.-M. Debatin, Oncogene 2006, 25, 4798-4811;
37. S. Elmore, Toxicol. Pathol. 2007, 35, 495-516.
38. E. A. Slee, C. Adrain, S. J. Martin, J. Biol. Chem. 2001, 276, 7320-7326;
39. K. M. Boatright, G. S. Salvesen, Curr. Opin. Cell Biol. 2003, 15, 725-731.
40. D. Acehan, X. Jiang, D. G. Morgan, J. E. Hauser, X. Wang, C. W. Akey, Mol. Cell 2002, 9, 423-432;
41. S. J. Riedl, G. S. Salvesen, Nat. Rev. Mol. Cell Biol. 2007, 8, 405-413.
42. H. Li, H. Zhu, C.-J. Xu, J. Yuan, Cell 1998, 94, 491-501;
43. B. C. Barnhart, E. C. Alappat, M. E. Peter, Semin. Immunol. 2003, 15, 185-193.
44. X. Wang, Y. Chen, Q.-b. Han, C.-y. Chan, H. Wang, Z. Liu, C. H.-k. Cheng, D. T. Yew, M. C. M. Lin, M.-l. He, H.-x. Xu, J. J. Y. Sung, H.-f. Kung, Proteomics 2009, 9, 242-253;
45. J. Davenport, J. R. Manjarrez, L. Peterson, B. Krumm, B. S. Blagg, R. L. Matts, J. Nat. Prod. 2011, 74, 1085-1092.
46. S. Kasibhatla, K. A. Jessen, S. Maliartchouk, J. Y. Wang, N. M. English, J. Drewe, L. Qiu, S. P. Archer, A. E. Ponce, N. Sirisoma, S. Jiang, H.-Z. Zhang, K. R. Gehlsen, S. X. Cai, D. R. Green, B. Tsang, Proc. Natl. Acad. Sci. USA 2005, 102, 12095-12100.
47. E. Ortiz-Sánchez, T. R. Daniels, G. Helguera, O. Martinez-Maza, B. Bonavida, M. L. Penichet, Leukemia 2009, 23, 59-70.
48. Y. Qin, L. Meng, C. Hu, W. Duan, Z. Zuo, L. Lin, X. Zhang, J. Ding, Mol. Cancer Ther. 2007, 6, 2429-2440.
49. M. K. Pandey, B. Sung, K. S. Ahn, A. B. Kunnumakkara, M. M. Chaturvedi, B. B. Aggarwal, Blood 2007, 110, 3517-3525;
50. X. Zhu, H.. Zhang, Y. Lin, P. Chen, J. Min, Z. Wang, W. Xiao, B. Chen, J. Chemother. 2009, 21, 666-672;
51. X. Wang, N. Lu, Q. Yang, D. Gong, C. Lin, S. Zhang, M. Xi, Y. Gao, L. Wei, Q. Guo, Q. You, Eur. J. Med. Chem. 2011, 46, 1280-1290.
52. J. Yu, Q.-L. Guo, Q.-D. You, L. Zhao, H.-Y. Gu, Y. Yang, H.-w. Zhang, Z. Tan, X. Wang, Carcinogenesis 2006, 28, 632-638.
53. Z.-Q. Wu, Q.-L. Guo, Q.-D. You, L. Zhao, H.-Y. Gu, Biol. Pharm. Bull. 2004, 27, 1769-1774;
54. J. Yu, Q.-L. Guo, Q.-D. You, S.-S. Lin, Z. Li, H.-Y. Gu, H.-w. Zhang, Z. Tan, X. Wang, Cancer Chemother. Pharmacol. 2006, 58, 434-443;
55. Q. Zhao, Y. Yang, J. Yu, Q.-D. You, S. Zeng, H.-Y. Gu, N. Lu, Q. Qi, W. Liu, X.-T. Wang, Q.-L. Guo, Cancer Lett. 2008, 262, 223-231;
56. Q.-L. Guo, S.-S. Lin, Q.-D. You, H.-Y. Gu, J. Yu, L. Zhao, Q. Qi, F. Liang, Z. Tan, X. Wang, Life Sci. 2006, 78, 1238-1245;
57. J. Chen, H.-Y. Gu, N. Lu, Y. Yang, W. Liu, Q. Qi, J.-J. Rong, X.-T. Wang, Q.-D. You, Q.-L. Guo, Life Sci. 2008, 83, 103-109.
58. H. Gu, X. Wang, S. Rao, J. Wang, J. Zhao, F. L. Ren, R. Mu, Y. Yang, Q. Qi, W. Liu, N. Lu, H. Ling, Q. You, Q. Guo, Mol. Cancer Ther. 2008, 7, 3298-3305;
59. J.-J. Rong, R. Hu, Q. Qi, H.-Y. Gu, Q. Zhao, J. Wang, R. Mu, Q.-D. You, Q.-L. Guo, Cancer Lett. 2009, 284, 102-112;
60. H.-Y. Gu, Q.-L. Guo, Q.-D. You, W. Liu, Q. Qi, L. Zhao, S.-T. Yuan, K. Zhang, Chin. J. Nat. Med. 2005, 3, 168-172.
61. F. Nie, X. Zhang, Q. Qi, L. Yang, Y. Yang, W. Liu, N. Lu, Z. Wu, Q. You, Q. Guo, Toxicology 2009, 260, 60-67.
62. W. Liu, Q.-L. Guo, Q.-D. You, L. Zhao, H.-Y. Gu, S.-T. Yuan, World J. Gastroenterol. 2005, 11, 3655-3659;
63. D. Zhai, C. Jin, C.-w. Shiau, S. Kitada, A. C. Satterthwait, J. C. Reed, Mol. Cancer Ther. 2008, 7, 1639-1646;
64. X. Xu, Y. Liu, L. Wang, J. He, H. Zhang, X. Chen, Y. Li, J. Yang, J. Tao, Int. J. Dermatol. 2009, 48, 186-192.
65. K. Hirschberg, C. M. Miller, J. Ellenberg, J. F. Presley, E. D. Siggia, R. D. Phair, J. Lippincott-Schwartz, J. Cell Biol. 1998, 143, 1485-1503.
66. T. E. McGraw, L. Greenfield, F. R. Maxfield, J. Cell Biol. 1987, 105, 207-214.
67. D. R. Green, J. C. Reed, Science 1998, 281, 1309-1312;
68. B. Mignotte, J.-L. Vayssiere, Eur. J. Biochem. 1998, 252, 1-15;
69. S. W. G. Tait, D. R. Green, Nat. Rev. Mol. Cell Biol. 2010, 11, 621-632.
70. V. R. Fantin, M. J. Berardi, L. Scorrano, S. J. Korsmeyer, P. Leder, Cancer Cell 2002, 2, 29-42;
71. P. Constantini, E. Jacotot, D. Decaudin, G. Kroemer, J. Natl. Cancer Inst. 2002, 92, 1042-1053;
72. V. R. Fantin, P. Leder, Oncogene 2006, 25, 4787-4797.
73. J. S. Armstrong, Br. J. Pharmacol. 2006, 147, 239-248.
74. S. J. Ralph, P. Low, L. Dong, A. Lawen, J. Neuzil, Recent Pat. Anti-Cancer Drug Discovery 2006, 1, 327-346;
75. J. Neuzil, X.-F. Wang, L.-F. Dong, P. Low, S. J. Ralph, FEBS Lett. 2006, 580, 5125-5129.
76. S. J. Ralph, J. Neuzil, Mol. Nutr. Food Res. 2009, 53, 9-38;
77. S. J. Ralph, S. Rodríguez-Enríquez, J. Neuzil, R. Moreno-Sánchez, Mol. Aspects Med. 2010, 31, 29-59.
78. S. Borrello, M. E. De Leo, T. Galeotti, Mol. Aspects Med. 1993, 14, 253-258.
79. S. Fulda, G. Kroemer, Drug Discovery Today 2009, 14, 885-890;
80. N. Hail, Jr., H. J. Kim, R. Lotan, Apoptosis 2006, 11, 1677-1694;
81. J. Dörrie, H. Gerauer, Y. Wachter, S. J. Zunino, Cancer Res. 2001, 61, 4731-4739;
82. J. Neuzil, J. C. Dyason, R. Freeman, L.-F. Dong, L. Prochazka, X.-F. Wang, I. Scheffer, S. J. Ralph, J. Bioenerg. Biomembr. 2007, 39, 65-72.
83. A. Lemarie, S. Grimm, Oncogene 2011, 30, 3985-4003;
84. L.-F. Dong, R. Freeman, J. Liu, R. Zobalova, A. Marin-Hernandez, M. Stantic, J. Rohlena, K. Valis, S. Rodriguez-Enriquez, B. Butcher, J. Goodwin, U. T. Brunk, P. K. Witting, R. Moreno-Sanchez, I. E. Scheffler, S. J. Ralph, J. Neuzil, Clin. Cancer Res. 2009, 15, 1593-1600.
85. For selected manuscripts on the synthesis of GA and related compounds see: ref. [3a, b, e, f].