Skip to main content
×
×
Home

Microbial and dietary factors associated with the 8-prenylnaringenin producer phenotype: a dietary intervention trial with fifty healthy post-menopausal Caucasian women

  • Selin Bolca (a1) (a2), Sam Possemiers (a1), Veerle Maervoet (a1), Inge Huybrechts (a3), Arne Heyerick (a2), Stefaan Vervarcke (a4), Herman Depypere (a5), Denis De Keukeleire (a2), Marc Bracke (a6), Stefaan De Henauw (a3), Willy Verstraete (a1) and Tom Van de Wiele (a1)...
Abstract

Hop-derived food supplements and beers contain the prenylflavonoids xanthohumol (X), isoxanthohumol (IX) and the very potent phyto-oestrogen (plant-derived oestrogen mimic) 8-prenylnaringenin (8-PN). The weakly oestrogenic IX can be bioactivated via O-demethylation to 8-PN. Since IX usually predominates over 8-PN, human subjects may be exposed to increased doses of 8-PN. A dietary intervention trial with fifty healthy post-menopausal Caucasian women was undertaken. After a 4 d washout period, participants delivered faeces, blank urine and breath samples. Next, they started a 5 d treatment with hop-based supplements that were administered three times per d and on the last day, a 24 h urine sample was collected. A semi-quantitative FFQ was used to estimate fat, fibre, alcohol, caffeine and theobromine intakes. The recoveries of IX, 8-PN and X in the urine were low and considerable inter-individual variations were observed. A five-fold increase in the dosage of IX without change in 8-PN concentration resulted in a significant lower IX recovery and a higher 8-PN recovery. Classification of the subjects into poor (60 %), moderate (25 %) and strong (15 %) 8-PN producers based on either urinary excretion or microbial bioactivation capacity gave comparable results. Recent antibiotic therapy seemed to affect the 8-PN production negatively. A positive trend between methane excretion and 8-PN production was observed. Strong 8-PN producers consumed less alcohol and had a higher theobromine intake. From this study we conclude that in vivoO-demethylation of IX increases the oestrogenic potency of hop-derived products.

  • View HTML
    • Send article to Kindle

      To send this article to your Kindle, first ensure no-reply@cambridge.org is added to your Approved Personal Document E-mail List under your Personal Document Settings on the Manage Your Content and Devices page of your Amazon account. Then enter the ‘name’ part of your Kindle email address below. Find out more about sending to your Kindle. Find out more about sending to your Kindle.

      Note you can select to send to either the @free.kindle.com or @kindle.com variations. ‘@free.kindle.com’ emails are free but can only be sent to your device when it is connected to wi-fi. ‘@kindle.com’ emails can be delivered even when you are not connected to wi-fi, but note that service fees apply.

      Find out more about the Kindle Personal Document Service.

      Microbial and dietary factors associated with the 8-prenylnaringenin producer phenotype: a dietary intervention trial with fifty healthy post-menopausal Caucasian women
      Available formats
      ×
      Send article to Dropbox

      To send this article to your Dropbox account, please select one or more formats and confirm that you agree to abide by our usage policies. If this is the first time you use this feature, you will be asked to authorise Cambridge Core to connect with your <service> account. Find out more about sending content to Dropbox.

      Microbial and dietary factors associated with the 8-prenylnaringenin producer phenotype: a dietary intervention trial with fifty healthy post-menopausal Caucasian women
      Available formats
      ×
      Send article to Google Drive

      To send this article to your Google Drive account, please select one or more formats and confirm that you agree to abide by our usage policies. If this is the first time you use this feature, you will be asked to authorise Cambridge Core to connect with your <service> account. Find out more about sending content to Google Drive.

      Microbial and dietary factors associated with the 8-prenylnaringenin producer phenotype: a dietary intervention trial with fifty healthy post-menopausal Caucasian women
      Available formats
      ×
Copyright
Corresponding author
*Corresponding author: Tom Van de Wiele, fax +32 9 264 62 48, email tom.vandewiele@ugent.be
References
Hide All
Adlercreutz, H (2002) Phyto-oestrogens and cancer. Lancet Oncol 3, 364373.
Fletcher, RJ (2003) Food sources of phyto-oestrogens and their precursors in Europe. Br J Nutr 89, S39S43.
Ososki, AL & Kennely, EJ (2003) Phytoestrogens: a review of the present state of research. Phytother Res 17, 845869.
Rowland, IR, Faughnan, M, Hoey, L, Wähälä, K, Williamson, G & Cassidy, A (2003) Bioavailability of phyto-estrogens. Br J Nutr 89, S45S58.
Blakesmith, SJ, Lyons-Wall, PM, Joannou, GE, Petocz, P & Samman, S (2005) Urinary isoflavonoid excretion is inversely associated with the ratio of protein to dietary fibre intake in young women. Eur J Nutr 59, 284290.
Horner, NK, Kristal, AR, Prunty, J, Skor, HE, Potter, JD & Lampe, JW (2002) Dietary determinants of plasma enterolactone. Cancer Epidemiol Biomarkers Prev 11, 121126.
Coldham, NG & Sauer, MJ (2001) Identification, quantitation and biological activity of phytoestrogens in a dietary supplement for breast enhancement. Food Chem Toxicol 39, 12111224.
Heyerick, A, Vervarcke, S, Depypere, HT, Bracke, ME & De Keukeleire, D (2006) A first prospective, randomized, double-blind, placebo-controlled study on the use of a standardized hop extract to alleviate menopausal discomforts. Maturitas 54, 164175.
Milligan, SR, Kalita, JC, Heyerick, A, Rong, H, De Cooman, L & De Keukeleire, D (1999) Identification of a potent phytoestrogen in hops (Humulus lupulus L.) and beer. J Clin Endocrinol Metab 83, 22492252.
Schaefer, O, Hümpel, M, Fritzemeier, K-H, Bohlmann, R & Schleuning, W-D (2003) 8-prenylnaringenin is a potent ERα selective phytoestrogen present in hops and beer. J Steroid Biochem Mol Biol 84, 359360.
Possemiers, S, Heyerick, A, Robbens, V, De Keukeleire, D & Verstraete, W (2005) Activation of pro-estrogens form hops (Humulus lupulus L.) by intestinal microbiota; conversion of isoxanthohumol into 8-prenylnaringenin. J Agric Food Chem 53, 62816288.
Guo, J, Nikolic, D, Chadwick, LR, Pauli, GF & van Breemen, RB (2006) Identification of human hepatic cytochrome P450 enzymes involved in the metabolism of 8-prenylnaringenin and isoxanthohumol form hops (Humulus lupulus L.). Drug Metab Dispos 34, 11521159.
Nikolic, D, Li, Y, Chadwick, LR, Grubjesic, S, Schwab, P, Metz, P & van Breemen, RB (2004) Metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus), by human liver microsomes. Drug Metab Dispos 32, 272279.
Stevens, JF, Taylor, AW & Deinzer, ML (1999) Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography-tandem mass spectrometry. J Chromatogr A 832, 97107.
Possemiers, S, Bolca, S, Grootaert, C, Heyerick, A, Decroos, K, Dhooge, W, De Keukeleire, D, Rabot, S, Verstraete, W & Van de Wiele, T (2006) Isoxanthohumol from hops (Humulus lupulus L.) is activated into the potent phytoestrogen 8-prenylnaringenin in vitro and in the human intestine. J Nutr 136, 18621867.
Schaefer, O, Bohlmann, R, Schleuning, W-D, Schulze-Forster, K & Hümpel, M (2005) Development of a radioimmunoassay for the quantitative determination of 8-prenylnaringenin in biological matrices. J Agric Food Chem 53, 28812889.
Rowland, IR, Wiseman, H, Sanders, TAB, Adlercreutz, H & Bowey, EA (2000) Interindividual variation in metabolism of soy isoflavones and lignans: influence of habitual diet on equol production by the gut microflora. Nutr Cancer 36, 2732.
Cummings, JH & Macfarlane, GT (1991) The control and consequences of bacterial fermentation in the human colon. J Appl Bacteriol 70, 443459.
Frankenfeld, CL, Patterson, RE, Horner, NK, Neuhouser, ML, Skor, HE, Kalhorn, TF, Howald, WN & Lampe, JW (2003) Validation of a soy food frequency questionnaire and evaluation of correlates of plasma isoflavone concentrations in postmenopausal women. Am J Clin Nutr 77, 674680.
Soares, ACF, Lederman, HM, Fagundes-Neto, U & de Morais, MB (2005) Breath methane associated with slow colonic transit time in children with chronic constipation. J Clin Gastroenterol 39, 512515.
Boeckx, P, Van Cleemput, O & Villaralvo, I (1996) Methane emission from a landfill and the methane oxidising capacity of its covering soil. Soil Biol Biochem 28, 13971405.
Hoey, L, Rowland, IR, Lloyd, AS, Clarke, DB & Wiseman, H (2004) Influence of soya-based infant formula consumption on isoflavone and gut microflora metabolite concentrations in urine and on faecal microflora composition and metabolic activity in infants and children. Br J Nutr 91, 607616.
Berg, JO, Nord, CE & Wadstrom, T (1978) Formation of glycosidases in batch and continuous cultures of Bacteroides fragilis. Appl Environ Microbiol 35, 269273.
Superior Health Council (2006) Recommended daily allowances in Belgium: revisions November 2006, 1st ed. Brussels: Federal Public Service Health, Food Chain Safety Environment.
Frankenfeld, CL, McTiernan, A, Tworoger, SS, et al. (2004) Serum steroid hormones, sex hormone-binding globulin concentrations and urinary hydroxylated estrogen metabolites in post-menopausal women in relation to daidzein-metabolizing phenotypes. J Steroid Biochem Mol Biol. 88, 399408.
Pollock, BG, Wylie, M & Stack, JA (1999) Inhibition of caffeine metabolism by estrogen replacement therapy in postmenopausal women. J Clin Pharmacol 39, 936940.
Avula, B, Ganzera, M, Warnick, JE, Feltenstein, MW, Sufka, KJ & Khan, IA (2004) High-performance liquid chromatographic determination of xanthohumol in rat plasma, urine and fecal samples. J Chromatogr Sci 42, 378382.
Gerhaüser, C, Alt, A, Heiss, E, et al. (2002) Cancer chemopreventive activity of xanthohumol, a natural product derived from hop. Mol Cancer Ther. 1, 959969.
Nikolic, D, Li, Y, Chadwick, LR & van Breemen, RB (2006) In vitro studies of intestinal permeability and hepatic and intestinal metabolism of 8-prenylnaringenin, a potent phytoestrogen form hops (Humulus lupulus L.). Pharm Res 23, 864872.
Rad, M, Hümpel, M, Schoemaker, RC, Schleuning, W-D, Cohen, AF & Burggraaf, J (2006) Pharmacokinetics and systemic endocrine effects of the phyto-oestrogen 8-prenylnaringenin after single oral doses to postmenopausal women. Br J Clin Pharmacol 62, 288296.
Setchell, KDR, Brown, NM, Desai, PB, Zimmer-Nechimias, L, Wolfe, B, Jakate, AS, Creutzinger, V & Heubi, JE (2003) Bioavailability, disposition, and dose-response effects of soy isoflavones when consumed by healthy women at physiologically typical dietary intakes. J Nutr 133, 10271035.
Wiseman, H, Casey, K, Bowey, EA, Duffy, R, Davies, M, Rowland, IR, Lloyd, AS, Murray, A, Thompson, A & Clarke, DB (2004) Influence of 10 wk of soy consumption on plasma concentrations and excretion of isoflavonoids and on gut microflora metabolism in healthy adults. Am J Clin Nutr 80, 692699.
Xu, X, Wang, H, Murphy, PA, Cook, L & Hendrich, S (1994) Daidzein is a more bioavailable soymilk isoflavone than is genistein in adult women. J Nutr 124, 825832.
Karr, SC, Lampe, JW, Huchins, AM & Slavin, JL (1997) Urinary isoflavonoid excretion in humans is dose dependent at low to moderate levels of soy-protein consumption. Am J Clin Nutr 66, 4651.
Lampe, JW, Karr, SC, Hutchins, AM & Slavin, JL (1998) Urinary equol excretion with a soy challenge: influence of habitual diet. Proc Soc Exp Biol Med 217, 335339.
Bond, JH, Engel, RR & Levitt, MD (1971) Factors influencing pulmonary methane excretion in man. J Exp Med 133, 572588.
Miller, TL & Wolin, MJ (1986) Methanogens in human and animal intestinal tracts. Syst Appl Microbiol 7(2-3), 223229.
Fernandes, J, Wolever, TMS & Rao, AV (2000) Interrelationships between age, total dietary fiber intake and breath methane in humans. Nutr Res 20, 929940.
Calloway, DH, Colasito, DJ & Mathews, RD (1966) Gases produced by human intestinal microflora. Nature 212, 12381239.
Frankenfeld, CL, Atkinson, C, Thomas, WK, Goode, EL, Gonzalez, A, Jokela, T, Wähälä, K, Schwartz, SM, Li, SS & Lampe, JW (2004) Familial correlations, segregation analysis, and nongenetic correlates of soy isoflavone-metabolizing phenotypes. Exp Biol Med 229, 902913.
LeMarchand, L, Franke, AA, Custer, LJ, Wilkens, LR & Cooney, RV (1997) Lifestyle and nutritional correlates of cytochrome CYP1A2 activity: inverse associations with plasma lutein and alpha-tocopherol. Pharmacogenetics 7, 1119.
Rizzo, N, Hispard, E, Dolbeault, S, Dally, S, Leverge, R & Girre, C (1997) Impact of long-term ethanol consumption on CYP1A2 activity. Clin Pharmacol Ther 62, 505509.
Higdon, JV & Frei, B (2006) Coffee and health: a review of recent human research. Crit Rev Food Sci Nutr 46, 101123.
Gates, S & Miners, O (1999) Cytochrome P450 isoform selectivity in human hepatic theobromine metabolism. J Clin Pharmacol 47, 299305.
Lampe, JW, Skor, HE, Wähälä, K, Howald, WN & Chen, C (2001) Wheat bran and soy protein feeding do not alter urinary excretion of the isoflavan equol in premenopausal women. J Nutr 131, 740744.
Vedrine, N, Mathey, J, Morand, C, Brandolini, M, Davicco, MJ, Guy, L, Remesy, C, Coxam, V & Manach, C (2006) One-month exposure to soy isoflavones did not induce the ability to produce equol in postmenopausal women. Eur J Clin Nutr 60, 10391045.
Batterham, TJ, Shutt, DA, Hart, NK, Braden, AWH & Tweeddale, HJ (1971) Metabolism of intraruminally administered [4-14C]formononetin and [4-14C]biochanin A in sheep. Aust J Agric Res 22, 131138.
Lundh, TJO, Pettersen, H & Kiessling, K (1988) Demethylation and conjugation of formononetin and daidzein in sheep and cow liver microsomes. J Agric Food Chem 36, 2225.
Schmider, J, Greenblatt, DJ, Von Moltke, LL, Karsov, D, Vena, R, Friedman, HL & Shader, RI (1997) Biotransformation of mestranol to ethinyl estradiol in vitro: the role of cytochrome P-450 2C9 and metabolic inhibitors. J Clin Pharmacol 37, 193200.
Milligan, SR, Kalita, JC, Pocock, V, Heyerick, A, De Cooman, L, Rong, H & De Keukeleire, D (2002) Oestrogenic activity of the hop phyto-oestrogen, 8-prenylnaringenin. Reproduction 123, 235242.
Recommend this journal

Email your librarian or administrator to recommend adding this journal to your organisation's collection.

British Journal of Nutrition
  • ISSN: 0007-1145
  • EISSN: 1475-2662
  • URL: /core/journals/british-journal-of-nutrition
Please enter your name
Please enter a valid email address
Who would you like to send this to? *
×

Keywords

Metrics

Altmetric attention score

Full text views

Total number of HTML views: 0
Total number of PDF views: 0 *
Loading metrics...

Abstract views

Total abstract views: 0 *
Loading metrics...

* Views captured on Cambridge Core between <date>. This data will be updated every 24 hours.

Usage data cannot currently be displayed