Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines

Food and Chemical Toxicology

Volumn 37, Issue 4, 1999, Pages 271-285

  Miranda, C L ^a   Stevens, J F ^a   Helmrich, A ^a   Henderson, M C ^a   Rodriguez, R J ^a   Yang, Y H ^a   Deinzer, M L ^a   Barnes, D W ^a   Buhler, D R ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

Antiproliferative agents; Breast cancer; Chalcones; Hops; MCF 7; Prenylated flavonoids; Xanthohumol

Indexed keywords

2',4',6',4 TETRAHYDROXY 3' GERANYLCHALCONE; 2',4',6',4 TETRAHYDROXY 3' PRENYLCHALCONE; CHALCONE DERIVATIVE; DEHYDROCYCLOXANTHOHUMOL; DEHYDROCYCLOXANTHOHUMOL HYDRATE; FLAVONOID; HUMULUS LUPULUS EXTRACT; ISOXANTHOHUMOL; UNCLASSIFIED DRUG; XANTHOHUMOL;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CELL COUNT; CELL PROLIFERATION; CHEMOPROPHYLAXIS; COLON CANCER; CONTROLLED STUDY; CYTOTOXICITY; DNA SYNTHESIS; DOSE RESPONSE; HUMAN; HUMAN CELL; OVARY CANCER;

ANIMALS; BEER; BIOLOGICAL ASSAY; CELL DIVISION; CELL SURVIVAL; DNA FRAGMENTATION; FLAVONOIDS; GELS; HUMANS; PROTEIN ISOPRENYLATION; RATS; RHODAMINES; ROSALES; SEPHAROSE; TRYPAN BLUE; TUMOR CELLS, CULTURED; TUMOR STEM CELL ASSAY;

EID: 0032791775     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0278-6915(99)00019-8     Document Type: Article

References (32)

1. Acosta D., Anuforo D., Smith R. Preparation of primary monolayer cultures of postnatal rat liver slices. Journal of Tissue Culture Methods. 6:1980;25-30.
2. Anto R.J., Sukumaran K., Kuttan G., Rao M.N.A., Subbaraju V., Kuttan R. Anticancer and antioxidant activity of synthetic chalcones and related compounds. Cancer Letters. 97:1995;33-37.
3. Arends M.J., Wyllie A.H. Apoptosis: mechanisms and roles in pathology. International Review of Experimental Pathology. 32:1991;223-254.
4. Barnes S., Peterson T.G., Coward L. Rationale for the use of genistein-containing soy matrices in chemoprevention trials for breast and prostate cancer. Journal of Cell Biochemistry. Suppl. 22:1995;181-187.
5. Bohm B. A. (1994) The minor flavonoids. In The Flavonoids: Advances in Research Since 1986, ed. J. B. Harborne, pp. 387-440. Chapman & Hall, New York.
6. Chu T.M., Lin T.H., Kawinski E. Detection of soluble P-glycoprotein in culture media and extracellular fluids. Biochemical and Biophysical Research Communications. 203:1994;506-512.
7. Conseil G., Baudichon H., Dayan G., Jault J. M., Barron D. and DiPietro A. 1998. Flavonoids: a new class of modulators with bifunctional interactions at vicinal ATP and steroid-binding sites on mouse P-glycoprotein. Proceedings of the National Academy of Sciences of the U.S.A. In press.
8. De Mello J.F., De Lima O.G., De Albuquerque M.M., Marini-Bettolo G.B., Lyra F.D., Da Silva E.C. O and C prenylated chalcones with antineoplastic and antibiotic activities isolated from Lonchocarpus neuroscapha Benth. Revista Instituto de Antibioticos (Recife). 14:1974;39-50.
9. De Vincenzo R., Scambia G., Benedetti Panici P., Ranelletti F.O., Bonanino G., Ercoli Monache A.Delle F., Ferrari F., Piantelli M., Mancuso S. Effect of synthetic and naturally occurring chalcones on ovarian cancer cell growth: structure-activity relationships. Anticancer Drug Research. 10:1995;481-490.
10. Hoffman R. Potent inhibition of breast cancer cell lines by the isoflavonoid kievetone: comparison with genistein. Biochemical and Biophysical Research Communications. 211:1995;600-606.
11. Jain P., Rajah T.T., Pento J.T. Antitumour activity of a novel antiestrogen (Analog II) on human breast cancer cells. Anti-Cancer Drugs. 8:1997;964-973.
12. Konig A., Schwartz G.K., Mohammad R.M., Al-Katib A., Gabrilove J.L. The novel cyclin-dependent kinase inhibitor flavopiridol downregulates Bcl-2 and induces growth arrest and apoptosis in chronic B-cell leukemia lines. Blood. 90:1997;4307-4312.
13. Lee H., Wang H.W., Su H.Y., Hao N.J. The structure-activity relationships of flavonoids as inhibitors of cytochrome P-450 enzymes in rat liver microsomes and the mutagenicity of 2-amino-3-methyl-imidazo[4,5-f]quinoline. Mutagenesis. 9:1994;101-106.
14. Middleton E., Jr and Kandaswami C. (1994) The impact of plant flavonoids on mammalian biology: implications for immunity, inflammation and cancer. In The Flavonoids, ed. J. B. Harborne, pp. 619-652. Chapman & Hall, New York.
15. Nielsen S.E., Breinholt V., Justesen U., Cornett C., Dragsted L.O. In vitro transformation of flavonoids by rat liver microsomes. Xenobiotica. 28:1998;389-401.
16. Nishino H., Tokuda H., Satomi Y., Iwashima A., Iwata S., Nagata N., Shibata S. Inhibitory effects of chalcone derivatives on tumour-promoter-induced phenomena and on growth of malignant cells. Journal of the Kyoto Prefectural University of Medicine. 102:1993;1-6.
17. Pezutto J.M. Plant-derived anticancer agents. Biochemical Pharmacology. 53:1997;121-133.
18. Pharmar 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., Van Marck V., Singh S.K., Kumar N., Malhotra S., Kumar R., Rajwanshi V.K., Jain R., Mareel M.M. Anti-invasive activity of alkaloids and polyphenolics in vitro. Bioorganic Medicine and Chemistry. 5:1997;1609-1619.
19. Ramanathan R., Tan C.H., Das N.P. Inhibitory effects of 2-hydroxychalcone and other flavonoids on human cancer cell proliferation. International Journal of Oncology. 3:1993;115-119.
20. Rubinstein L.V., Shoemaker R.H., Paull K.D., Simon R.M., Tosini S., Skehan P., Scudiero D.A., Monks A., Boyd M.R. Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumour cell lines. Journal of the National Cancer Institute. 82:1990;1113-1118.
21. Satomi Y. Inhibitory effects of 3′-methyl-3-hydroxy-chalcone on proliferation of human malignant tumour cells and on skin carcinogenesis. International Journal of Cancer. 55:1993;506-514.
22. Seo E-K., Silva G.L., Chai H-B., Chagwedera T.E., Farnsworth N.R., Cordell G.A., Pezzuto J.M., Kinghorn A.D. Cytotoxic prenylated flavanones from Monotes engleri. Phytochemistry. 45:1997;509-515.
23. Shibata S. Anti-tumourigenic chalcones. Stem Cells (Dayt). 12:1994;44-52.
24. 2/M arrest, and apoptosis. Journal of Cell Biochemistry. 68:1998;44-54.
25. Skehan P., Storeng R., Sundiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesh H., Kenney S., Boyd M.R. New colorimetric cytotoxicity assay for anticancer-drug screening. Journal of the National Cancer Institute. 82:1990;1107-1112.
26. So F.V., Guthrie N., Chambers A.F., Carroll K.K. Inhibition of proliferation of estrogen receptor-positive MCF-7 human breast cancer cells by flavonoids in the presence and absence of excess estrogen. Cancer Letters. 112:1997;127-133.
27. So F.V., Guthrie N., Chambers A.F., Moussa M., Carroll K.K. Inhibition of human breast cancer cell proliferation and delay of mammary tumourigenesis by flavonoids and citrus juices. Nutrition and Cancer. 26:1996;167-181.
28. Stevens J.F., Ivancic M., Hsu V.L., Deinzer M.L. Prenylflavonoids from Humulus lupulus. Phytochemistry. 44:1997;1575-1585.
29. Stevens J. F., Miranda C. L., Buhler D. R. and Deinzer M. L. (1998) Chemistry and biology of hop flavonoids. Journal of the American Society for the Brewing Chemistry 56, 136-145.
30. Stevens J.F., Taylor A.W., Deinzer M.L. Quantitative analysis of xanthohumol and related flavonoids in hops and beer by liquid chromatography-tandem mass spectrometry. Journal of Chromatography. A832:1999;97-107.
31. Wattenberg L.W., Coccia J.B., Galbrath A.R. Inhibition of carcinogen-induced pulmonary and mammary carcinogenesis by chalcone administered subsequent to carcinogen exposure. Cancer Letters. 83:1994;165-169.
32. Yit C.C., Das N.P. Cytotoxic effect of butein on human colon adenocarcinoma cell proliferation. Cancer Letters. 82:1994;65-72.