Effects of the chemically synthesized flavanone 7-(O-prenyl)naringenin-4′-acetate on the estrogen signaling pathway in vivo and in vitro

Journal of Steroid Biochemistry and Molecular Biology

Volumn 107, Issue 1-2, 2007, Pages 114-119

  Kretzschmar, Georg ^a   Vollmer, Günter ^a   Schwab, Pia ^a   Tischer, Sandra ^a   Metz, Peter ^a   Zierau, Oliver ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

7 (O Prenyl)naringenin 4 acetate; Estrogenic activity; Flavanones; Gene expression; MVLN cells; Selective estrogen receptor modulators; Yeast screen estrogen receptor assay

Indexed keywords

7 (O PRENYL)NARINGENIN 4' ACETATE; CLUSTERIN; COMPLEMENT COMPONENT C3; ESTRADIOL; ESTROGEN; ESTROGEN RECEPTOR BETA; FLAVANONE DERIVATIVE; LUCIFERASE; MESSENGER RNA; NARINGENIN; PROGESTERONE; UNCLASSIFIED DRUG; VASCULOTROPIN; VITELLOGENIN;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CELL STRAIN MCF 7; CHEMICAL STRUCTURE; CONTROLLED STUDY; ESTROGEN RESPONSIVE ELEMENT; FEMALE; GENE EXPRESSION REGULATION; NONHUMAN; PROTEIN EXPRESSION; RAT; REAL TIME POLYMERASE CHAIN REACTION; REPORTER GENE; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION; SYNTHESIS; UTERUS WEIGHT; WISTAR RAT;

ANIMALS; CELL LINE; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; ESTROGENS; FEMALE; FLAVANONES; GENE EXPRESSION PROFILING; GENE EXPRESSION REGULATION; GENES, REPORTER; HUMANS; ORGAN SIZE; RATS; RATS, WISTAR; RNA, MESSENGER; SIGNAL TRANSDUCTION; TRANS-ACTIVATION (GENETICS); UTERUS;

RATTUS;

EID: 34548395018     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2007.02.008     Document Type: Article

References (22)

1. Rossouw J.E., Anderson G.L., Prentice R.L., LaCroix A.Z., Kooperberg C., Stefanick M.L., Jackson R.D., Beresford S.A., Howard B.V., Johnson K.C., Kotchen J.M., and Ockene J. Risks and benefits of estrogen plus progestin in healthy postmenopausal women: principal results From the Women's Health Initiative randomized controlled trial. JAMA 288 3 (2002) 321-333
2. Grady D., Herrington D., Bittner V., Blumenthal R., Davidson M., Hlatky M., Hsia J., Hulley S., Herd A., Khan S., Newby L.K., Waters D., Vittinghoff E., and Wenger N. Cardiovascular disease outcomes during 6.8 years of hormone therapy: Heart and Estrogen/progestin Replacement Study follow-up (HERS II). JAMA 288 1 (2002) 49-57
3. Hulley S., Furberg C., Barrett-Connor E., Cauley J., Grady D., Haskell W., Knopp R., Lowery M., Satterfield S., Schrott H., Vittinghoff E., and Hunninghake D. Noncardiovascular disease outcomes during 6.8 years of hormone therapy: Heart and Estrogen/progestin Replacement Study follow-up (HERS II). JAMA 288 1 (2002) 58-66
4. Beral V. Breast cancer and hormone-replacement therapy in the Million Women Study. Lancet 362 9382 (2003) 419-427
5. Seo E.K., Silva G.L., Chai H.B., Chagwedera T.E., Farnsworth N.R., Cordell G.A., Pezzuto J.M., and Kinghorn A.D. Cytotoxic prenylated flavanones from Monotes engleri. Phytochemistry 45 3 (1997) 509-515
6. Gester S., Metz P., Zierau O., and Vollmer G. An efficient synthesis of the potent phytoestrogens 8-prenylnaringenin and 6-(1,1-dimethylallyl)naringenin by europium(III)-catalyzed Claisen rearrangement. Tetrahedron 57 (2001) 1015-1018
7. Zierau O., Morrissey C., Watson R.W., Schwab P., Kolba S., Metz P., and Vollmer G. Antiandrogenic activity of the phytoestrogens naringenin, 6-(1,1-dimethylallyl)naringenin and 8-prenylnaringenin. Planta Med. 69 9 (2003) 856-858
8. Diel P., Thomae R.B., Caldarelli A., Zierau O., Kolba S., Schmidt S., Schwab P., Metz P., and Vollmer G. Regulation of gene expression by 8-prenylnaringenin in uterus and liver of Wistar rats. Planta Med. 70 1 (2004) 39-44
9. Zierau O., Geis R.B., Tischer S., Schwab P., Metz P., and Vollmer G. Uterine effects of the phytoestrogen 6-(1,1-dimethylallyl)naringenin in rats. Planta Med. 70 7 (2004) 590-593
10. Zierau O., Gester S., Schwab P., Metz P., Kolba S., Wulf M., and Vollmer G. Estrogenic activity of the phytoestrogens naringenin, 6-(1,1-dimethylallyl)naringenin and 8-prenylnaringenin. Planta Med. 68 5 (2002) 449-451
11. Milligan S., Kalita J., Pocock V., Heyerick A., De Cooman L., Rong H., and De Keukeleire D. Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin. Reproduction 123 2 (2002) 235-242
12. Milligan S.R., Kalita J.C., Pocock V., Van De Kauter V., Stevens J.F., Deinzer M.L., Rong H., and De Keukeleire D. The endocrine activities of 8-prenylnaringenin and related hop (Humulus lupulus L.) flavonoids. J. Clin. Endocrinol. Metab. 85 12 (2000) 4912-4915
13. Miyamoto M., Matsushita Y., Kiyokawa A., Fukuda C., Iijima Y., Sugano M., and Akiyama T. Prenylflavonoids: a new class of non-steroidal phytoestrogen (Part 2). Estrogenic effects of 8-isopentenylnaringenin on bone metabolism. Planta Med. 64 6 (1998) 516-519
14. Tokalov S.V., Henker Y., Schwab P., Metz P., and Gutzeit H.O. Toxicity and cell cycle effects of synthetic 8-prenylnaringenin and derivatives in human cells. Pharmacology 71 1 (2004) 46-56
15. Pons M., Gagne D., Nicolas J.C., and Mehtali M. A new cellular-model of response to estrogens-a bioluminescent test to characterize (anti) estrogen molecules. Biotechniques 9 4 (1990) 450
16. Demirpence E., Duchesne M.J., Badia E., Gagne D., and Pons M. MVLN cells: a bioluminescent MCE-7-derived cell line to study the modulation of estrogenic activity. J. Steroid Biochem. Mol. Biol. 46 3 (1993) 355-364
17. Routledge E.J., and Sumpter J.P. Estrogenic activity of surfactants and some of their degradation products assessed using a recombinant yeast screen. Environ. Toxicol. Chem. 15 (1996) 241-248
18. Pfaffl M.W. A new mathematical model for relative quantification in real-time RT-PCR. Nucl. Acids Res. 29 9 (2001) e45
19. Kretzschmar G., Nisslein T., Zierau O., and Vollmer G. No estrogen like effects of an isopropanolic extract of Rhizoma cimicifugae racemosae on uterus and vena cava of rats after 17 days of treatment. J. Steroid Biochem. Mol. Biol. 97 3 (2005) 271-277
20. Kraus W.L., and Katzenellenbogen B.S. Regulation of progesterone receptor gene expression and growth in the rat uterus: modulation of estrogen actions by progesterone and sex steroid hormone antagonists. Endocrinology 132 6 (1993) 2371-2379
21. Routledge E.J., and Sumpter J.P. Oestrogenic activity of surfactants and some of their degradation products assessed using a recombinant yeast screen. Environ. Toxicol. Chem. 15 (1996) 241-248
22. Demirpence E., Duchesne M.J., Badia E., Gagne D., and Pons M. MVLN cells: a bioluminescent MCF-7-derived cell line to study the modulation of estrogenic activity. J. Steroid Biochem. Mol. Biol. 46 (1993) 355-364