Antioxidant and anticancer activity of 3′-formyl-4′, 6′-dihydroxy-2′-methoxy-5′-methylchalcone and (2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone

Journal of Pharmacy and Pharmacology

Volumn 59, Issue 4, 2007, Pages 553-559

  Ye, Chun Lin ^a   Liu, Yu ^a   Wei, Dong Zhi ^b  

^a ZHEJIANG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 3' FORMYL 4', 6' DIHYDROXY 2 METHOXY 5 METHYLCHALCONE; 8 FORMYL 5 HYDROXY 7 METHOXY 6 METHYLFLAVANONE; ALPHA TOCOPHEROL; FLAVONOID; NITROBLUE TETRAZOLIUM; PHENAZINE METHOSULFATE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; SCAVENGER; SUPEROXIDE; UNCLASSIFIED DRUG; (2S) 8 FORMYL 5 HYDROXY 7 METHOXY 6 METHYLFLAVANONE; (2S)-8-FORMYL-5-HYDROXY-7-METHOXY-6-METHYLFLAVANONE; 2,2-DIPHENYL-1-PICRYLHYDRAZYL; 3' FORMYL 4', 6' DIHYDROXY 2' METHOXY 5' METHYLCHALCONE; 3'-FORMYL-4', 6'-DIHYDROXY-2'-METHOXY-5'-METHYLCHALCONE; ANTINEOPLASTIC AGENT; ANTIOXIDANT; CHALCONE DERIVATIVE; FLAVANONE DERIVATIVE; HERBACEOUS AGENT; PICRIC ACID;

ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; HUMAN; HUMAN CELL; IC 50; LIPID PEROXIDATION; CHEMISTRY; COMPARATIVE STUDY; DOSE RESPONSE; DRUG EFFECT; FLOWER; ISOLATION AND PURIFICATION; MEDICINAL PLANT; MYRTACEAE; PHYTOTHERAPY; TUMOR CELL LINE;

ALPHA-TOCOPHEROL; ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; CELL LINE, TUMOR; CHALCONES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUGS, CHINESE HERBAL; FLAVANONES; FLAVONOIDS; FLOWERS; FREE RADICAL SCAVENGERS; HUMANS; LIPID PEROXIDATION; MYRTACEAE; PHYTOTHERAPY; PICRATES; PLANTS, MEDICINAL; SUPEROXIDES;

EID: 34250191810     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/jpp.59.4.0010     Document Type: Article

References (45)

1. Abdulla, M., Gruber, P. (2000) Role of diet modification in cancer prevention. Biofactors 12: 45-51
2. Adams, J. D., Odunze, I. N. (1991) Oxygen free radicals and Parkinson disease. Free Radical Biol. Med. 10: 161-169
3. Blois, M. S. (1958) Antioxidant determinations by the use of a stable free radical. Nature 29: 1199-1200
4. Cadenas, E., Davies, K. J. A. (2000) Mitochondrial free radical generation, oxidative stress, and aging. Free Radic. Biol. Med. 29: 222-230
5. Cerutti, P. (1994) Oxy-radicals and cancer. Lancet 344: 862-863
6. Cushman, M., Nagarathnam, D. (1991) Cytotoxicities of some flavonoid analogues. J. Nat. Prod. 54: 1556-1660
7. Davies, K. J., Hochstein, P. (1982) Ubisemiquinone radicals in liver implications for a mitochondrial Q cycle in vivo. Biochem. Biophys. Res. Commun. 107: 1292-1299
8. Fukai, T., Marumo, A., Kaitou, K., Kanda, T., Terada, S., Nomura, T. (2002) Anti-helicobacter pylori flavonoids from licorice extract. Life Sci. 71: 1449-1463
9. Gulcin, I., Buyukokuroglu, M. E., Oktay, M., Kufrevioglu, O. I. (2002) On the in vitro antioxidant properties of melatonin. J. Pineal Res. 33: 167-171
10. Harman, D. (1980) Free radical theory of aging: origin of life, evolution and aging. Age 3: 100-102
11. Hertog, M. G. L., Feskens, E. J. M., Hollman, P. C. H., Katan, M. B., Kromhout, D. (1993) Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen elderly study. Lancet 342: 1007-1011
12. Hirano, T., Oka, K., Akiba, M. (1989) Antiproliferative effects of synthetic and naturally occurring flavonoids on tumor cells of the human breast carcinoma cell ZR-75-1. Res. Commun. Chem. Pathol. Pharmacol. 64: 69-78
13. Hollman, P. C. H., Katan, M. B. (1997) Absorption, metabolism, and health effects of dietary flavonoids in man. Biomed. Pharmacother. 51: 305-310
14. Husain, S. R., Cillard, J., Cillard, P. (1987) Hydroxyl radical scavenging activity of flavonoids. Phytochemistry 26: 2489-2491
15. Ikezoe, T., Chen, S. S., Heber, D., Taguchi, H., Koeffler, H. P. (2001) Baicalin is a major component of PC-SPES which inhibits the proliferation of human cancer cells via apoptosis and cell cycle arrest. Prostate 49: 285-292
16. Kajimoto, S., Takanashi, N., Kajimoto, T., Xu, M., Cao, J., Masuda, Y., Aiuchi, T., Nakajo, S., Ida, Y., Nakaya, K. (2002) Sophoranone, extracted from a traditional Chinese medicine Shan Dou Gen, induces apoptosis in human leukemia U937 cells via formation of reactive oxygen species and opening of mitochondrial permeability transition pores. Int. J. Cancer 99: 879-890
17. Kanazawa, M., Satomi, Y., Mizutani, Y., Ukimura, O., Kawauchi, A., Sakai, T., Baba, M., Okuyama, T., Nishino, H., Miki, T. (2003) Isoliquiritigenin inhibits the growth of prostate cancer. Eur. Urol. 43: 580-586
18. Lin, Y. M., Chen, F. C., Lee, K. H. (1989) Hinokiflavone, a cytotoxicity of the related biflavonoids. Planta Med. 55: 166-168
19. Liu, F., Ng, T. B. (2000) Antioxidative and free radical scavenging activities of selected medicinal herbs. Life Sci. 66: 725-735
20. Middleton, E. (1996) Biological properties of plant flavonoids: an overview. Int. J. Pharmacol. 34: 344-348
21. Mier, S., Kaner, J., Akiri, B., Hadas, S. P. (1995) Determination and involvement of aqueous reducing compounds in oxidative defense systems of various senescing leaves. J. Agric. Food Chem. 43: 1813-1817
22. Mistuda, H., Yuasumoto, K., Iwami, K. (1996) Antioxidation action of indole compounds during the autoxidation of linoleic acid. Nihon Eiyo Shokuryo Gakkai Shi 19: 210-214
23. Mori, A., Nishino, C., Enoki, N., Tawata, S. (1988) Cytotoxicity of plant flavonoids against Hela cells. Phytochemistry 27: 1017-1020
24. Moskovitz, J., Yim, K. A., Choke, P. B. (2002) Free radicals and disease. Arch. Biochem. Biophys. 397: 354-349
25. Mosmann, T. (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65: 55-63
26. Oyaizu, M. (1986) Studies on products of browning reaction - anti-oxidative activities of products of browning reaction prepared from glucosamine. Jpn J. Nutr. 44: 307-315
27. Parmar, V. S., Bracke, M. E., Philippe, J., Wengel, J., Jain, S. C., Olsen, C. E., Bisht, K. S., Sharma, N. K., Courtens, A., Sharma, S. K., Vennekens, K., Marck, V. V., Singh, S. K., Kumar, N., Kumar, A, Malhotra, S., Malhotra, R., Rajwanshi, V. K., Jain, R., Mareel, M. M. (1997) Anti-invasive activity of alkaloids and polyphenolics in vitro. Bioorg. Med. Chem. 5: 1609-1619
28. Pezzuto, J. M. (1997) Plant-derived anticancer agents. Biochem Pharmacol 53: 121-33
29. Pietta, P. G. (2000) Flavonoids as antioxidants. J. Nat. Prod. 63: 1035-1042
30. Rice-Evans, C. A., Miller, N. J. (1996) Antioxidant activities of flavonoids as bioactive components of food. Biochem. Soc. Trans. 24: 790-795
31. Russo, A., Cardile, V., Lombardob, L., Vanella, L., Vanella, A., Garbarino, J. A. (2005) Antioxidant activity and antiproliferative action of methanolic extractof Geum quellyon Sweet roots in human tumor cell lines. J. Ethnopharmacol. 100: 323-332
32. Sánchez-Moreno, C. (2002) Methods used to evaluate the free radical scavenging activity in foods and biological systems. Food Sci. Technol. Int. 8: 121-137
33. Sasaki, S., Ohta, T., Decber, E. A. (1996). Antioxidant activity of water-soluble fractions of salmon spermary tissue. J. Agric. Food Chem. 44: 1682-1686
34. Satomi, Y. (1993) Inhibitory effects of 3-methyl-3hydroxychalcone on proliferation of human malignant tumor cells and on skin carcinogenesis. Int. J. Cancer 55: 506-514
35. Tanaka, M., Kuie, C. W., Nagashima, Y., Taguchi, T. (1988) Application of antioxidative Maillard reaction products from histidine and glucose to saline products. Nippon Suisan Gakkai Shi 54: 1409-1414
36. Torel, J., Cillard, J., Cillard, P. (1986) Antioxidant activity of flavonoids and reactivity with peroxy radical. Phytochemistry 25: 383-385
37. Tyagi, A., Bhatia, N., Condon, M. S., Bosland, M. C., Agarwal, C., Agarwal, R. (2002) Antiproliferative and apoptotic effects of silibinin in rat prostate cancer cells. Prostate 53: 211-217
38. Verma, A. K., Johnson, J. A., Gould, M. N., Tanner, M. A. (1998) Inhibition of 7,12-dimethylbenz(a)anthracene and N-nitro-methylurea induced rat mammary cancer by dietary flavonolquercetin. Cancer Res. 48: 5754-5788
39. Wattenberg, L. W., Coccia, J. B., Galhaith, A. R. (1994) Inhibition of carcinogen-induced pulmonary and mammary carcinogenesis by chalcone administered after carcinogen exposure. Cancer Lett. 83: 165-169
40. Wei, H., Tye, L., Bresnick, E., Birt, D. F. (1990) Inhibitory effect of apigenin, a plant flavonoid, on epidermal ornithine decarboxylase and skin tumor promotion in mice. Cancer Res. 50: 499-502
41. Woo, A. Y. H., Waye, M. M. Y., Kwan, H. S., Chan, M. C. Y., Chau, C. F., Cheng, C. H. K. (2002) Inhibition of ATPases by Cleistocalyx operculatus: a possible mechanism for the cardiotonic actions of the herb. Vasc. Pharmacol. 38: 163-168
42. Wu, J., Wu, Y., Yang, B. B. (2002) Anticancer activity of Hemsleya amabilis extract. Life Sci. 71: 2161-2170
43. Ye, C. L., Lu, Y. H., Wei, D. Z. (2004) Flavonoids from Cleistocalyx operculatus. Phytochemistry 65: 445-447
44. Yildirim, A., Mavi, A., Oktay, M., Kara, A. A., Algur, O. F., Bilaloglu, V. (2000) Comparison of antioxidant and antimicrobial activities of tilia (Tilia argenta Desf Ex DC), sage (Salvia triloba L.) and black tea (Camellia sinensis) extracts. J. Agric. Food Chem. 48: 5030-5034
45. Yit, C. C., Das, N. P. (1994) Cytotoxic effect of butein on human colon adenocarcinoma cell proliferation. Cancer Lett. 82: 65-72