Bioactive dimeric carbazole alkaloids from Murraya koenigii

Journal of Natural Products

Volumn 76, Issue 6, 2013, Pages 993-1000

  Uvarani, Chokkalingam ^a,c   Sankaran, Mathan ^a   Jaivel, Nanjundan ^b   Chandraprakash, Kumarasamy ^a   Ata, Athar ^c   Mohan, Palathurai S ^a  

^a BHARATHIAR UNIVERSITY   (India)

^b TAMIL NADU AGRICULTURAL UNIVERSITY   (India)

^c UNIVERSITY OF WINNIPEG   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; ANTIOXIDANT; BISGERAYAFOLINE A; BISGERAYAFOLINE B; BISGERAYAFOLINE C; CARBAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CYTOTOXICITY; DNA BINDING; FRUIT; IN VITRO STUDY; MURRAYA KOENIGII; NONHUMAN; PROTEIN INTERACTION;

ALKALOIDS; ALPHA-GLUCOSIDASES; ANTINEOPLASTIC AGENTS, PHYTOGENIC; ANTIOXIDANTS; CARBAZOLES; CHLOROFORM; DNA; DRUG SCREENING ASSAYS, ANTITUMOR; FRUIT; HCT116 CELLS; HELA CELLS; HUMANS; INDIA; MOLECULAR STRUCTURE; MURRAYA;

MURRAYA KOENIGII;

EID: 84879680816     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np300464t     Document Type: Article

References (79)

1. Chevallier, A. The Encyclopedia of Medicinal Plants; Dorling Kindersley: London, 1996.
2. Bringmann, G.; Ledermann, A.; Francois, G. Heterocycles 1995, 40, 293
3. Rahman, A.; Zaidi, R.; Firdous, S. Fitoterapia 1988, LIX, 494-495
4. Ramsewak, R. S.; Nair, M. G.; Strasburg, G. M.; DeWitt, D. L.; Nitiss, J. L. J. Agric. Food Chem. 1999, 47, 444-447
5. Chowdhury, B. K.; Jha, S.; Bhattacharyya, P.; Mukherjee, J. Indian J. Chem. 2001, 40B, 490-494
6. Rahman, M. M.; Gray, A. I. Phytochemistry 2005, 66, 1601-1606
7. Wang, Y. S.; He, H. P.; Shen, M. Y.; Hong, X.; Hao, X. J. J. Nat. Prod. 2003, 66, 416-418
8. Meragelman, K. M.; McKee, C. T.; Boyd, R. M. J. Nat. Prod. 2000, 63, 427-428
9. Fiebig, M.; Pezzuto, J. M.; Soejarto, D. D.; Kinghorn, A. D. Phytochemistry 1985, 24, 3041-3043
10. Ito, C.; Itoigawa, M.; Nakao, K.; Murata, T.; Tsuboi, M.; Kaneda, N.; Furukawa, H. Phytomedicine 2006, 13, 359-365
11. Chakraborty, D. P. Fortschr. Chem. Org. Naturst. 1977, 34, 299
12. Chakraborty, M.; Nath, A. C.; Khasnobis, S.; Chakraborty, M.; Konda, Y.; Harigaya, Y.; Komiyama, K. Phytochemistry 1997, 46, 751-755
13. Itoigawa, M.; Kashiwada, Y.; Ito, C.; Furukawa, H.; Tachibana, Y.; Bastow, K. F.; Lee, K. H. J. Nat. Prod. 2000, 63, 893-897
14. Ito, C.; Itoigawa, M.; Aizawa, K.; Yoshida, K.; Ruangrungsi, N.; Furukawa, H. J. Nat. Prod. 2009, 72, 1202-1204
15. Potterat, O. Curr. Org. Chem. 1997, 1, 415-440
16. Kato, S.; Kawai, H.; Kawasaki, T.; Toda, Y.; Urata, T.; Hayakawa, Y. J. Antibiot. 1989, XLII, 1879-1881
17. Iwatsuki, M.; Niki, E.; Kato, S. BioFactors 1993, 4, 123-128
18. Kato, S.; Shindo, K.; Kataoka, Y.; Yamagishi, Y.; Mochizuki, J. J. Antibiot. 1991, 44, 903-907
19. Tanaka, M.; Shin-ya, K.; Furihata, K.; Seto, H. J. Antibiot. 1995, 48, 326-328
20. Roy, M. K.; Thalang, V. N.; Trakoontivakorn, G.; Nakahara, K. Biochem. Pharmacol. 2004, 67, 41-51
21. Brooker, R.; Gajjar, K. T. Curr. Sci. 1953, 22, 44-45
22. Kirtikar, K. R.; Basu, B. D. Ind. Med. Plants 1960, 1, 473
23. Narasimhan, N. S.; Paradhar, M. V.; Chitguppi, V. P. Tetrahedron Lett. 1968, 53, 5501-5504
24. Chowdhury, B. K.; Chakraborty, D. P. Phytochemistry 1971, 10, 1967-1970
25. Chakraborty, D. P.; Roy, S.; Ruha, R. J. Indian Chem. Soc. 1978, 55, 1114-1115
26. Rao, R. A. V.; Rhide, K. S.; Mujumdar, R. B. Chem. Ind. 1980, 17, 697-698
27. Bhattacharyya, L.; Roy, S. K.; Chakraborty, D. P. Phytochemistry 1982, 21, 2432-2433
28. Roy, S.; Bhattacharyya, L.; Roy, S. K.; Chakraborty, D. P. J. Indian Chem. Soc. 1982, 59, 1369-1371
29. Bhattacharyya, P.; Chowdhury, B. K. Indian J. Chem. 1985, 24B, 452-452
30. Ito, C.; Thoyama, Y.; Omura, M.; Kajiura, I.; Furukawa, H. Chem. Pharm. Bull. 1993, 41, 2096-2100
31. Reisch, J.; Adebajo, A. C.; Kumar, V.; Aladesanmi, A. J. Phytochemistry 1994, 36, 1073-1076
32. Saha, C.; Chowdhury, B. K. Phytochemistry 1998, 48, 363-366
33. Nutan, M. T. H.; Hasan, C. M.; Rashid, M. A. Fitoterapia 1999, 70, 130-133
34. Knolker, H. J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303-4427
35. Adebajo, A. C.; Reisch, J. Fitoterapia 2000, 71, 334-337
36. Narasimhan, N. S.; Paradkar, M. V.; Kelkar, S. L. Indian J. Chem. 1970, 8, 473-474
37. Narasimhan, N. S.; Paradkar, M. V.; Chitguppi, V. P.; Kelkar, S. L. Indian J. Chem. 1975, 13, 993-999
38. Roglic, G.; Unwin, N. Diabetes Res. Clin. Pract. 2010, 87, 15-19
39. Kordik, C. P.; Reitz, A. B. J. Med. Chem. 1991, 42, 181
40. Berrino, F.; Verdecchia, A.; Lutz, J. M.; Lombardo, C.; Micheli, A.; Capocaccia, R. Eur. J. Cancer 2009, 45, 901-908
41. Goss, P. E.; Baker, M. A.; Carver, J. P.; Dennis, J. W. Clin. Cancer Res. 1995, 1, 935
42. Pace, G. W.; Leaf, C. D. Free Radical Biol. Med. 1995, 4, 523-528
43. Bendich, A. Adv. Exp. Med. Biol. 1990, 262, 1-12
44. Broek, V.; Leon, A. G. M. Carbohydrate Drug Design; New York, 1997; p 471.
45. Dervan, P. B. Bioorg. Med. Chem. 2001, 9, 2215-2235
46. Demeunynck, M.; Bailly, C.; Wilson, W. D. From small molecules to drugs. DNA and RNA Binders; Wiley-VCH: Weinheim, 2002; pp 482-497.
47. Berrino, F.; Verdecchia, A.; Lutz, J. M.; Lombardo, C.; Micheli, A.; Capocaccia, R. Eur. J. Cancer 2009, 45, 901-908
48. Bush, J. A.; Long, B. H.; Catino, J. J.; Bradner, W. T.; Tomita, K. J. Antibiotics 1987, 40, 668
49. Rodrigues Pereira, E.; Belin, L.; Sancelme, M.; Prudhomme, M.; Ollier, M.; Rapp, M.; Severe, D.; Riou, J. F.; Fabbro, D.; Meyer, T. J. Med. Chem. 1996, 39, 4471-4477
50. Mollataghi, A.; Coudiere, E.; Hadi, A. H. A.; Mukhtar, M. R.; Awang, K.; Litaudon, M.; Ata, A. Fitoterapia 2012, 83, 298-302
51. Kingston, D. G. I. J. Nat. Prod. 2011, 74, 496-511
52. Chakraborty, D. P. Progress in the Chemistry of Organic Natural Products; Herz, W.; Grisebach, H.; Kirby, G. W., Eds.; Springer-Verlag: New York, 1977; Vol. 34, p 299.
53. Bhattacharyya, D. P.; Chakraborty, D. P. Progress in the Chemistry of Organic Natural Products; Herz, W.; Grisebach, H.; Kirby, G. W., Eds.; Springer-Verlag: New York, 1987; Vol. 52, p 159.
54. Chakraborty, D. P.; Roy, S. Progress in the Chemistry of Organic Natural Products; Herz, W.; Grisebach, H.; Kirby, G. W., Eds.; Springer-Verlag: New York, 1991; Vol. 57, p 71.
55. Yukari, T.; Hiroe, K.; Nordin, H. L.; Nobuji, N. J. Agric. Food Chem. 2003, 51, 6461-6467
56. Cuong, N. M.; Hung, T. Q.; Sung, T. V.; Taylor, W. C. Chem. Pharm. Bull. 2004, 52, 1175-1178
57. Botha, J. J.; Ferreira, D.; Roux, D. G. J. Chem. Soc., Perkin Trans. 1 1981, 1235-1245
58. Shen, Y. C.; Cheng, Y. B.; Lan, T. W.; Liaw, C. C.; Liou, S. S.; Kuo, Y. H.; Khalil, A. T. J. Nat. Prod. 2007, 70, 1139-1145
59. Chen, M.; Kilgore, N.; Lee, K. H.; Chen, D. F. J. Nat. Prod. 2006, 69, 1697-1701
60. Ferreira, D.; Marais, J. P. J.; Slade, D. Phytochemistry 2005, 66, 2216-2237
61. Gill, M.; Steglich, W. Progress in the Chemistry of Organic Natural Products; Springer Verlag: Wien, 1987; Vol 51, pp 1-317.
62. Ito, C.; Wu, T. S.; Furukawa, H. Chem. Pharm. Bull. 1990, 38 (5) 1143-1145
63. Ito, C.; Furukawa, H. Chem. Pharm. Bull. 1990, 38 (6) 1548-1550
64. Furukawa, H.; Wu, T. S.; Kuoh, C. S. Chem. Pharm. Bull. 1985, 38 (6) 2611-2613
65. Ito, C.; Furukawa, H. Chem. Pharm. Bull. 1991, 39 (5) 1355-1357
66. Wang, Y. S.; He, H. P.; Shen, M. Y.; Hong, X.; Zhao, Q.; Hao, X. J. Chin. Chem. Lett. 2002, 13, 849-850
67. Furukawa, H.; Wu, T. S.; Ohta, T. Chem. Pharm. Bull. 1983, 31 (11) 4202-4205
68. Chakraborty, M.; Mukhopadhyay, S. Tetrahedron Lett. 2010, 51, 3732
69. Wu, T.-S.; Huang, S.-C.; Wu, P.-L. Tetrahedron Lett. 1996, 37, 7819
70. Wu, T.-S.; Wang, M.-L.; Lai, J.-S.; Chihiro, I.; Furukawa, H. Phytochemistry 1991, 30, 1052
71. Tysoe, S. A.; Morgan, R. J.; Baker, A. D.; Strekas, T. C. J. Phys. Chem. 1993, 97, 1707-1711
72. Haworth, I. S.; Elcock, A. H.; Freemann, J.; Rodger, A.; Richards, W. G. J. J. Biomol. Struct. Dyn. 1991, 9, 23-44
73. Raja, D. S.; Bhuvanesh, N. S. P.; Natarajan, K. Eur. J. Med. Chem. 2011, 46, 4584-4594
74. Shahabuddin, M. S.; Gopal, M.; Raghavan, S. C. J. Cancer Mol. 2007, 3, 139-146
75. Bailly, C.; Qu, X.; Chaires, J. B.; Colson, P.; Houssier, C.; Ohkubo, M.; Nishimure, S.; Yoshinari, T. J. Med. Chem. 1999, 42, 2927-2935
76. Tanious, F. A.; Ding, D.; Patrick, D. A.; Tidwell, R. R.; Wilson, W. D. Biochemistry 1997, 36, 15315-15325
77. Raja, D. S.; Bhuvanesh, N. S. P.; Natarajan, K. Inorg. Chem. 2011, 50, 12852-12866
78. Raja, D. S.; Paramaguru, G.; Bhuvanesh, N. S. P.; Reibenspies, J. H.; Renganathan, R.; Natarajan, K. Dalton Trans. 2011, 40, 4548-4559
79. Hu, Y.; Yang, Y.; Dai, C.; Liu, Y.; Xiao, X. Biomacromolecules 2010, 11, 106-112