Catalytic inhibition of eukaryotic topoisomerases i and II by flavonol glycosides extracted from vicia faba and lotus edulis

Journal of Natural Products

Volumn 74, Issue 11, 2011, Pages 2362-2370

  Tselepi, Maria ^a   Papachristou, Evaggelia ^a   Emmanouilidi, Aikaterini ^a   Angelis, Apostolos ^b   Aligiannis, Nektarios ^b   Skaltsounis, Alexios Leandros ^b   Kouretas, Demetrios ^a   Liadaki, Kalliopi ^a  

^a UNIVERSITY OF THESSALY   (Greece)

^b UNIVERSITY OF ATHENS   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DNA TOPOISOMERASE; DNA TOPOISOMERASE (ATP HYDROLYSING); DNA TOPOISOMERASE INHIBITOR; ETOPOSIDE; FLAVONOID GLYCOSIDE; KAEMPFEROL 3 O (5 O ACETYL ALPHA DEXTRO APIOFURANOSYL) 7 O ALPHA LEVO RHAMNOPYRANOSIDE; KAEMPFEROL 3 O (ALPHA LEVO RHAMNOPYRANOSYL[1-2] BETA DEXTRO GLUCOPYRANOSYL) 7 O ALPHA LEVO RHAMNOPYRANOSIDE; KAEMPFEROL 3 O (ALPHA LEVO RHAMNOPYRANOSYOL[1-2] BETA DEXTRO GALACTOPYRANOSYL) 7 O ALPHA LEVO RHAMNOPYRANOSIDE; KAEMPFEROL 3 O ALPHA LEVO ARABINOPYRANOSYL 7 O ALPHA LEVO RHAMNOPYRANOSIDE; KAEMPFEROL 3 O ALPHA LEVO RHAMNOPYRANOSYL 7 O ALPHA LEVO RHAMNOPYRANOSIDE; KAEMPFEROL 3 O BETA DEXTRO APIOFURANOSYL 7 O ALPHA LEVO RHAMNOPYRANOSIDE; KAEMPFEROL 3 O BETA DEXTRO GALACTOPYRANOSYL 7 O ALPHA LEVO RHAMNOPYRANOSIDE; KAEMPFEROL 3 O BETA DEXTRO GLUCOPYRANOSYL 7 O ALPHA LEVO RHAMNOPYRANOSIDE; POLYPHENOL DERIVATIVE; QUERCETIN 3 O (ALPHA LEVO RHAMNOPYRANOSYL[1-2] BETA DEXTRO GALACTOPYRANOSYL) 7 O ALPHA LEVO RHAMNOPYRANOSIDE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CELL STRAIN HEPG2; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SPECIFICITY; FEMALE; HELA CELL; HUMAN; HUMAN CELL; IC 50; LOTUS; LOTUS EDULIS; VICIA FABA; WHEAT GERM;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; DRUG SCREENING ASSAYS, ANTITUMOR; FLAVONOLS; GLYCOSIDES; GREECE; HELA CELLS; HEP G2 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; LOTUS; MOLECULAR STRUCTURE; TOPOISOMERASE I INHIBITORS; TOPOISOMERASE II INHIBITORS; VICIA FABA;

EID: 82355187638     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np200292u     Document Type: Article

References (64)

1. Venn, B. J.; Mann, J. I. Eur. J. Clin. Nutr. 2004, 58, 1443
2. Xu, B. J.; Yuan, S. H.; Chang, S. K. C. J. Food Sci. 2007, 72, S522
3. Mathers, J. C. Br. J. Nutr. 2002, 88, S273
4. Messina, M. J. Am. J. Clin. Nutr. 1999, 70, S439
5. Kushi, L. H.; Meyer, K. A.; Jacobs, D. R. Am. J. Clin. Nutr. 1999, 70, S451
6. Geil, P. B.; Anderson, J. W. J. Am. Coll. Nutr. 1994, 13, 549
7. Kris-Etherton, P. M.; Hecker, K. D.; Bonanome, A.; Coval, S. M.; Binkoski, A. E.; Hilpert, K. F.; Griel, A. E.; Etherton, T. D. Am. J. Med. 2002, 113, S71
8. Champ, M. M. Br. J. Nutr. 2002, 88, S307
9. Chang, K. C. In Functional Foods: Biochemical and Processing Aspects; Shi, J.; Mazz, J.; Maguer, M. L., Eds.; CRC Press: New York, 2002; Vol. II, pp 39-69.
10. Beninger, C. W.; Hosfield, G. L. J. Agric. Food Chem. 2003, 51, 7879
11. Madhujith, T.; Naczk, M.; Shahidi, F. J. Food Lipids 2004, 11, 220
12. Xu, B. J.; Chang, S. K. C. J. Food Sci. 2007, 72, S159
13. Xu, B. J.; Yuan, S. H.; Chang, S. K. C. J. Food Sci. 2007, 72, S167
14. Webb, A. L.; McCullough, M. L. Nutr. Cancer 2005, 51, 117
15. Barnes, S.; Boersma, B.; Patel, R.; Kirk, M.; Darley-Usmar, V. M.; Kim, H.; Xu, J. Biofactors 2000, 12, 209
16. Ren, W.; Qiao, Z.; Wang, H.; Zhu, L.; Zhang, L. Med. Res. Rev. 2003, 23, 519
17. Fresco, P.; Borges, F.; Diniz, C.; Marques, M. P. Med. Res. Rev. 2006, 26, 747
18. Yang, C. S.; Landau, J. M.; Huang, M. T.; Newmark, H. L. Annu. Rev. Nutr. 2001, 21, 381
19. Champoux, J. J. Annu. Rev. Biochem. 2001, 70, 369
20. Wang, J. C. Annu. Rev. Biochem. 1985, 54, 665
21. Wang, J. C. Nat. Rev. Mol. Cell. Biol. 2002, 3, 430
22. Li, T. K.; Liu, L. F. Annu. Rev. Pharmacol. Toxicol. 2001, 41, 53
23. Liu, L. F. Annu. Rev. Biochem. 1989, 58, 351
24. Ross, W. E. Biochem. Pharmacol. 1985, 34, 4191
25. D?Arpa, P.; Liu, L. F. Biochim. Biophys. Acta 1989, 989, 163
26. Drlica, K.; Malik, M. Curr. Top. Med. Chem. 2003, 3, 249
27. Li, M.; Miao, Z. H.; Chen, Z.; Chen, Q.; Gui, M.; Lin, L. P.; Sun, P.; Yi, Y. H.; Ding, J. Ann. Oncol. 2010, 21, 597
28. Wang, P.; Ownby, S.; Zhang, Z.; Yuan, W.; Li, S. Bioorg. Med. Chem. Lett. 2010, 20, 2790
29. Huang, H.; Chen, Q.; Ku, X.; Meng, L.; Lin, L.; Wang, X.; Zhu, C.; Wang, Y.; Chen, Z.; Li, M.; Jiang, H.; Chen, K.; Ding, J.; Liu, H. J. Med. Chem. 2010, 53, 3048
30. Goodell., J. R.; Ougolkov, A. V.; Hiasa, H.; Kaur, H.; Remmel, R.; Billadeau, D. D.; Ferguson, D. M. J. Med. Chem. 2008, 51, 179
31. Shinkre, B. A.; Raisch, K. P.; Fan, L.; Velu, S. E. Bioorg. Med. Chem. Lett. 2007, 17, 2890
32. Sadiq, A. A.; Patel, M. R.; Jacobson, B. A.; Escobedo, M.; Ellis, K.; Oppegard, L. M.; Hiasa, H.; Kratzke, R. A. Invest. New Drugs 2010, 28, 20
33. Spanou, C.; Bourou, G.; Dervishi, A.; Aligiannis, N.; Angelis, A.; Komiotis, D.; Skaltsounis, A. L.; Kouretas, D. J. Agric. Food Chem. 2008, 56, 6967
34. Hasan, A.; Ahmad, I.; Khan, M. A.; Choudhary, M. I. Phytochemistry 1996, 43, 1115
35. Nakano, K.; Takatani, M.; Tomimatsu, T.; Nohara, T. Phytochemistry 1983, 22, 2831
36. Mulinacci, N.; Vincieri, F. F.; Baldi, A.; Bambagiotti-Alberti, M.; Sendl, A.; Wagner, H. Phytochemistry 1995, 38, 531
37. Yoshimitsu, H.; Nishida, M.; Hashimoto, F.; Tanaka, M.; Sakata, Y.; Okawa, M.; Nohara, T. J. Nat. Med. 2007, 61, 334
38. Yahara, S.; Kohjyouma, M.; Kohoda, H. Phytochemistry 2000, 53, 469
39. Tomás-Lorente, F.; García-Grau, M. M.; Tomás- Barberán, F. A.; Nieto, J. L. Phytochemistry 1989, 28, 1993
40. Liu, Q.; Liu, M.; Mabry, T. J.; Dixon, R. A. Phytochemistry 1994, 36, 229
41. Agrawal, P. K. Carbon-13 NMR of Flavonoids; Elsevier Science Publishing Co.: Amsterdam, 1989.
42. Takaya, Y.; Kondo, Y.; Furukawa, T.; Niwa, M. J. Agric. Food Chem. 2003, 51, 8061
43. Crozier, A.; Clifford, M. N.; Ashihara, H. In Plant Secondary Metabolites. Occurrence, Structure and Role in the Human Diet; Crozier, A.; Clifford, M. N.; Ashihara, H., Eds.; Blackwell Publishing: Oxford, 2006.
44. Stagos, D.; Kazantzoglou, G.; Magiatis, P.; Mitaku, S.; Anagnostopoulos, K.; Kouretas, D. Int. J. Mol. Med. 2005, 15, 1013
45. Cho, K. H.; Pezzuto, J. M.; Bolton, J. L.; Steele, V. E.; Kelloff, G. J.; Lee, S. K.; Constantinou, A. Eur. J. Cancer 2000, 36, 2146
46. Constantinou, A.; Mehta, R.; Runyan, C.; Rao, K.; Vaughan, A.; Moon, R. J. Nat. Prod. 1995, 58, 217
47. Webb, M. R.; Ebeler, S. E. Biochem. J. 2004, 384, 527
48. Bandele, O. J.; Osheroff, N. Biochemistry 2007, 46, 6097
49. Mizushina, Y.; Ishidoh, T.; Kamisuki, S.; Nakazawa, S.; Takemura, M.; Sugawara, F.; Yoshida, H.; Sakaguchi, K. Biochem. Biophys. Res. Commun. 2003, 301, 480
50. Naowaratwattana, W.; De-Eknamkul, W.; De Mejia, E. G. J. Med. Food 2010, 13, 1045
51. Boege, F.; Straub, T.; Kehr, A.; Boesenberg, C.; Christiansen, K.; Andersen, A.; Jakob, F.; Köhrle, J. J. Biol. Chem. 1996, 271, 2262
52. Bandele, O. J.; Clawson, S. J.; Osheroff, N. Chem. Res. Toxicol. 2008, 21, 1253
53. Bandele, O. J.; Osheroff, N. Biochemistry 2007, 46, 6097
54. López-Lázaro, M.; Martín-Cordero, C.; Toro, M. V.; Ayuso, M. J. J. Enzyme Inhib. Med. Chem. 2002, 17, 25
55. López-Lázaro, M.; Willmore, E.; Austin, C. A. Mutat. Res. 2010, 696, 41
56. Moon, S. S.; Rahman, M. A.; Manir, M. M.; Jamal Ahamed, V. S. Arch. Pharm. Res. 2010, 33, 1169
57. Yang, J. H.; Kondratyuk, T. P.; Marler, L. E.; Qiu, X.; Choi, Y.; Cao, H.; Yu, R.; Sturdy, M.; Pegan, S.; Liu, Y.; Wang, L. Q.; Mesecar, A. D.; Van Breemen, R. B.; Pezzuto, J. M.; Fong, H. H.; Chen, Y. G.; Zhang, H. J. Phytochemistry 2010, 71, 641
58. Ibrahim, L. F.; Kawashty, S. A.; El-Hagrassy, A. M.; Nassar, M. I.; Mabry, T. J. Carbohydr. Res. 2008, 343, 155
59. Li, Y. L.; Gan, G. P.; Zhang, H. Z.; Wu, H. Z.; Li, C. L.; Huang, Y. P.; Liu, Y. W.; Liu, J. W. J. Ethnopharmacol. 2007, 113, 115
60. Li, Y.; Fang, H.; Xu, W. Mini Rev. Med. Chem. 2007, 7, 663
61. Kandaswami, C.; Lee, L. T.; Lee, P. P.; Hwang, J. J.; Ke, F. C.; Huang, Y. T.; Lee, M. T. In Vivo 2005, 19, 895
62. López-Lázaro, M. Curr. Med. Chem. Anticancer Agents 2002, 2, 691
63. Manach, C.; Donovan, J. L. Free Radical Res. 2004, 38, 771
64. Scudiero, D. A.; Shoemaker, R, H.; Paull, K. D.; Monks, A.; Tierney, S.; Nofziger, T. H.; Currens, M. J.; Seniff, D.; Boyd, M. R. Cancer Res. 1988, 48, 4827