Hop extracts and hop substances in treatment of menopausal complaints

Planta Medica

Volumn 79, Issue 7, 2013, Pages 576-579

  Keiler, Annekathrin M ^a   Zierau, Oliver ^a   Kretzschmar, Georg ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

8 prenylnaringenin; Cannabaceae; Humulus lupulus L.; isoxanthohumol; menopause; safety; xanthohumol

Indexed keywords

6 PRENYLNARINGENIN; 8 PRENYLNARINGENIN; DESMETHYLXANTHOHUMOL; ESTROGEN RECEPTOR ALPHA; FLAVONOID; HUMULUS LUPULUS EXTRACT; ISOXANTHOHUMOL; UNCLASSIFIED DRUG; XANTHOHUMOL;

BONE DENSITY; CLINICAL TRIAL (TOPIC); DRUG BLOOD LEVEL; DRUG EFFICACY; DRUG MECHANISM; DRUG SAFETY; DRUG STRUCTURE; DRUG TOLERABILITY; HUMAN; HUMULUS LUPULUS; MENOPAUSAL SYNDROME; NONHUMAN; OSTEOPOROSIS; PH; POSTMENOPAUSE; REVIEW; SEXUAL FUNCTION;

ESTROGEN RECEPTOR ALPHA; FEMALE; FLAVANONES; HOT FLASHES; HUMANS; HUMULUS; MAMMARY GLANDS, HUMAN; MENOPAUSE; OSTEOPOROSIS, POSTMENOPAUSAL; PHYTOESTROGENS; PHYTOTHERAPY; PLANT EXTRACTS; SEXUAL DYSFUNCTIONS, PSYCHOLOGICAL; UTERUS;

CANNABACEAE; HUMULUS LUPULUS;

EID: 84877837248     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0032-1328330     Document Type: Review

References (45)

1. Milligan S. R., Kalita J. C., Heyerick A., Rong H., Cooman L. D., Keukeleire D. D. Identification of a potent phytoestrogen in hops (Humulus lupulus L.) and beer. J Clin Endocrinol Metab: 1999; 84 2249 2249
2. Vlietinck A. J. Assessment report for herbal substance(s), herbal preparation(s) or combinations thereof with traditional use - Humulus lupulus L., flos. London EMEA: 2008
3. Milligan S. R., Kalita J. C., Pocock V., Kauter V. VD, Stevens J. F., Deinzer M. L., Rong H., Keukeleire D. D. The endocrine activities of 8-prenylnaringenin and related hop (Humulus lupulus L.) flavonoids. J Clin Endocrinol Metab: 2000; 85 4912 4915 (Pubitemid 32157686)
4. Milligan S., Kalita J., Pocock V., Heyerick A., Cooman L. D., Rong H., Keukeleire D. D. Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin. Reproduction: 2002; 123 235 242 (Pubitemid 34144673)
5. Zierau O., Gester S., Schwab P., Metz P., Kolba S., Wulf M., Vollmer G. Estrogenic activity of the phytoestrogens naringenin, 6-(1,1-dimethylallyl) naringenin and 8-prenylnaringenin. Planta Med: 2002; 68 449 451 (Pubitemid 34606690)
6. Schaefer O., Hümpel M., Fritzemeier K. H., Bohlmann R., Schleuning W. D. 8-Prenyl naringenin is a potent ER α selective phytoestrogen present in hops and beer. J Steroid Biochem Mol Biol: 2003; 84 359 360 (Pubitemid 36514851)
7. Diel P., Thomae R. B., Caldarelli A., Zierau O., Kolba S., Schmidt S., Schwab P., Metz P., Vollmer G. Regulation of gene expression by 8-prenylnaringenin in uterus and liver of Wistar rats. Planta Med: 2004; 70 39 44 (Pubitemid 38233911)
8. Zierau O., Kretzschmar G., Möller F., Weigt C., Vollmer G. Time dependency of uterine effects of naringenin type phytoestrogens in vivo. Mol Cell Endocrinol: 2008; 294 92 99
9. Kitaoka M., Kadokawa H., Sugano M., Ichikawa K., Taki M., Takaishi S., Iijima Y., Tsutsumi S., Boriboon M., Akiyama T. Prenylflavonoids: a new class of non-steroidal phytoestrogen (Part 1). Isolation of 8-isopentenylnaringenin and an initial study on its structure-activity relationship. Planta Med: 2007; 64 511 515
10. Komatsu M., Yokoe I., Shirataki Y. Studies on the constituents of Sophora species. XIII. Constituents of the aerial parts of Sophora tomentosa L. Chem Pharm Bull (Tokyo): 1978; 26 3863 3870 (Pubitemid 9109358)
11. Bohlmann F., Zdero C., King R. M., Robinson H. New prenylflavanoids from Marshallia grandiflora. Phytochemistry: 1979; 18 1246 1247
12. Chadwick L. R., Nikolic D., Burdette J. E., Overk C. R., Bolton J. L., van Breemen R. B., Fröhlich R., Fong H. HS, Farnsworth N. R., Pauli G. F. Estrogens and congeners from spent hops (Humulus lupulus). J Nat Prod: 2004; 67 2024 2032 (Pubitemid 40092549)
13. Chadwick L. R., Pauli G. F., Farnsworth N. R. The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on estrogenic properties. Phytomedicine: 2006; 13 119 131 (Pubitemid 41799601)
14. Stevens J. F., Miranda C. L., Buhler D. R., Deinzer M. L. Chemistry and biology of hop flavonoids. JASBC: 1998; 56 136 145 (Pubitemid 29033045)
15. Stevens J. F., Taylor A. W., Deinzer M. L. Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography-tandem mass spectrometry. J Chromatogr A: 1999; 832 97 107 (Pubitemid 29073728)
16. Possemiers S., Heyerick A., Robbens V., De Keukeleire D., Verstraete W. Activation of proestrogens from hops (Humulus lupulus L.) by intestinal microbiota; conversion of isoxanthohumol into 8-prenylnaringenin. J Agric Food Chem: 2005; 53 6281 6288 (Pubitemid 41169374)
17. Possemiers S., Bolca S., Grootaert C., Heyerick A., Decroos K., Dhooge W., Keukeleire D. D., Rabot S., Verstraete W., Wiele de T. V. The prenylflavonoid isoxanthohumol from hops (Humulus lupulus L.) is activated into the potent phytoestrogen 8-prenylnaringenin in vitro and in the human intestine. J Nutr: 2006; 136 1862 1867 (Pubitemid 43973589)
18. Guo J., Nikolic D., Chadwick L. R., Pauli G. F., van Breemen R. B. Identification of human hepatic cytochrome P450 enzymes involved in the metabolism of 8-prenylnaringenin and isoxanthohumol from hops (Humulus lupulus L.). Drug Metab Dispos: 2006; 34 1152 1159
19. Bolca S., Possemiers S., Maervoet V., Huybrechts I., Heyerick A., Vervarcke S., Depypere H., De Keukeleire D., Bracke M., De Henauw S., Verstraete W., Van de Wiele T. Microbial and dietary factors associated with the 8-prenylnaringenin producer phenotype: a dietary intervention trial with fifty healthy post-menopausal Caucasian women. Br J Nutr: 2007; 98 950 959 (Pubitemid 47543453)
20. Holick M. F., Lamb J. J., Lerman R. H., Konda V. R., Darland G., Minich D. M., Desai A., Chen T. C., Austin M., Kornberg J., Chang J. L., Hsi A., Bland J. S., Tripp M. L. Hop rho iso-alpha acids, berberine, vitamin D3 and vitamin K1 favorably impact biomarkers of bone turnover in postmenopausal women in a 14-week trial. J Bone Miner Metab: 2010; 28 342 350
21. 1 produces a favorable bone biomarker profile supporting healthy bone metabolism in postmenopausal women with metabolic syndrome. Nutr Res: 2011; 31 347 355
22. Ming L. G., Ge B. F., Wang M. G., Chen K. M. Comparison between 8-prenylnarigenin and narigenin concerning their activities on promotion of rat bone marrow stromal cells osteogenic differentiation in vitro. Cell Prolif: 2012; 45 508 515
23. Hümpel M., Isaksson P., Schaefer O., Kaufmann U., Ciana P., Maggi A., Schleuning W-D. Tissue specificity of 8-prenylnaringenin: protection from ovariectomy induced bone loss with minimal trophic effects on the uterus. J Steroid Biochem Mol Biol: 2005; 97 299 305 (Pubitemid 41607581)
24. Sehmisch S., Hammer F., Christoffel J., Seidlova-Wuttke D., Tezval M., Wuttke W., Stuermer K., Stuermer E. Comparison of the phytohormones genistein, resveratrol and 8-prenylnaringenin as agents for preventing osteoporosis. Planta Med: 2008; 74 794 801 (Pubitemid 351991112)
25. Freedman R. R. Hot flashes: behavioral treatments, mechanisms, and relation to sleep. Am J Med: 2005; 118 124 130
26. Berendsen H. H., Weekers A. H., Kloosterboer H. J. Effect of tibolone and raloxifene on the tail temperature of oestrogen-deficient rats. Eur J Pharmacol: 2001; 419 47 54 (Pubitemid 32441649)
27. Bowe J., Li X. F., Kinsey-Jones J., Heyerick A., Brain S., Milligan S., OByrne K. The hop phytoestrogen, 8-prenylnaringenin, reverses the ovariectomy-induced rise in skin temperature in an animal model of menopausal hot flushes. J Endocrinol: 2006; 191 399 405 (Pubitemid 44830615)
28. Dennerstein L., Alexander J. L. The menopause and sexual functioning. Annu Rev Sex Res: 2003; 14 64 82
29. Ågmo A., Turi A. L., Ellingsen E., Kaspersen H. Preclinical models of sexual desire: conceptual and behavioral analyses. Pharmacol Biochem Behav: 2004; 78 379 404 (Pubitemid 38901007)
30. Di Viesti V., Carnevale G., Zavatti M., Benelli A., Zanoli P. Increased sexual motivation in female rats treated with Humulus lupulus L. extract. J Ethnopharmacol: 2011; 134 514 517
31. Rad M., Hümpel M., Schaefer O., Schoemaker R. C., Schleuning W. D., Cohen A. F., Burggraaf J. Pharmacokinetics and systemic endocrine effects of the phyto-oestrogen 8-prenylnaringenin after single oral doses to postmenopausal women. Br J Clin Pharmacol: 2006; 62 288 296 (Pubitemid 44215528)
32. Heyerick A., Vervarcke S., Depypere H., Bracke M., Keukeleire D. D. A first prospective, randomized, double-blind, placebo-controlled study on the use of a standardized hop extract to alleviate menopausal discomforts. Maturitas: 2006; 54 164 175
33. Erkkola R., Vervarcke S., Vansteelandt S., Rompotti P., De Keukeleire D., Heyerick A. A randomized, double-blind, placebo-controlled, cross-over pilot study on the use of a standardized hop extract to alleviate menopausal discomforts. Phytomedicine: 2010; 17 389 396
34. Morali G., Polatti F., Metelitsa E., Mascarucci P., Magnani P., Brunenghi Marrè G. Open, non-controlled clinical studies to assess the efficacy and safety of a medical device in form of gel topically and intravaginally used in postmenopausal women with genital atrophy. Arzneimittelforschung: 2011; 56 230 238
35. Alder E. The Blatt-Kupperman menopausal index: a critique. Maturitas: 1998; 29 19 24 (Pubitemid 28247564)
36. Rossouw J. E., Anderson G. L., Prentice R. L., LaCroix A. Z., Kooperberg C., Stefanick M. L., Jackson R. D., Beresford S. AA, Howard B. V., Johnson K. C., Kotchen J. M., Ockene J. Risks and benefits of estrogen plus progestin in healthy postmenopausal women: principal results From the Womens Health Initiative randomized controlled trial. JAMA: 2002; 288 321 333 (Pubitemid 34761611)
37. Beral V., Banks E., Reeves G. Evidence from randomised trials on the long-term effects of hormone replacement therapy. The Lancet: 2002; 360 942 944 (Pubitemid 35283842)
38. Beral V. Breast cancer and hormone-replacement therapy in the Million Women Study. The Lancet: 2003; 362 419 427 (Pubitemid 36999703)
39. Beral V. Ovarian cancer and hormone replacement therapy in the Million Women Study. The Lancet: 2007; 369 1703 1710 (Pubitemid 46755369)
40. Chlebowski R. T., Hendrix S. L., Langer R. D., Stefanick M. L., Gass M., Lane D., Rodabough R. J., Gilligan M. A., Cyr M. G., Thomson C. A., Khandekar J., Petrovitch H., McTiernan A. Influence of estrogen plus progestin on breast cancer and mammography in healthy postmenopausal women: The Womens Health Initiative Randomized Trial. JAMA: 2003; 289 3243 3253 (Pubitemid 37430077)
41. Chlebowski R. T., Kuller L. H., Prentice R. L., Stefanick M. L., Manson J. E., Gass M., Aragaki A. K., Ockene J. K., Lane D. S., Sarto G. E., Rajkovic A., Schenken R., Hendrix S. L., Ravdin P. M., Rohan T. E., Yasmeen S., Anderson G. Breast cancer after use of estrogen plus progestin in postmenopausal women. N Engl J Med: 2009; 360 573 587
42. Overk C. R., Yao P., Chadwick L. R., Nikolic D., Sun Y., Cuendet M. A., Deng Y., Hedayat A. S., Pauli G. F., Farnsworth N. R., van Breemen R. B., Bolton J. L. Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense). J Agric Food Chem: 2005; 53 6246 6253 (Pubitemid 41169368)
43. Rimoldi G., Christoffel J., Wuttke W. Morphologic changes induced by oral long-term treatment with 8-prenylnaringenin in the uterus, vagina, and mammary gland of castrated rats. Menopause: 2006; 13 669 677 (Pubitemid 44079537)
44. Wang Y. J., Dou J., Cross K. P., Valerio L. G. Jr. Computational analysis for hepatic safety signals of constituents present in botanical extracts widely used by women in the United States for treatment of menopausal symptoms. Regul Toxicol Pharmacol: 2011; 59 111 124
45. Kretzschmar G., Zierau O., Wober J., Tischer S., Metz P., Vollmer G. Prenylation has a compound specific effect on the estrogenicity of naringenin and genistein. J Steroid Biochem Mol Biol: 2010; 118 1 6