8-Prenylnaringenin, the phytoestrogen in hops and beer, upregulates the function of the E-cadherin/catenin complex in human mammary carcinoma cells

Rong, Haojing; Boterberg, Tom; Maubach, Julie; Stove, Christophe; Depypere, Herman; Slambrouck, Séverine Van; Serreyn, Rudolphe; Keukeleire, Denis De; Mareel, Marcus; Bracke, Marc

doi:10.1078/0171-9335-00190

Cited by 40 publications

(28 citation statements)

References 19 publications

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“…However, 8-PN did not affect MCF-7/6 cells invasion in chick heart fragments in vitro. All these effects were similar to those observed with b-estradiol [78].…”

Section: Antiangiogenic Activity Of Prenylflavonoidssupporting

confidence: 74%

European Journal of Cancer

2007

European Journal of Cancer

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Beer is a complex alcoholic beverage made from barley (malt), hop, water and yeast. Phenolic constituents of beer are derived from malt (70-80%) and hop (20-30%). Structural classes include simple phenols, benzoic-and cinnamic acid derivatives, coumarins, catechins, di-, tri-and oligomeric proanthocyanidins, (prenylated) chalcones and flavonoids as well as alpha-and iso-alphaacids derived from hop. Compounds belonging to different structural classes have distinct profiles of biological activity in in vitro test systems, and in combination might lead to enhanced effects. Scientific evidence has accumulated over the past 10 years pointing to the cancer preventive potential of selected hop-derived beer constituents, i.e., prenylflavonoids including xanthohumol and isoxanthohumol, and hop bitter acids. Chemopreventive activities observed with these compounds relevant to inhibition of carcinogenesis at the initiation, promotion and progression phases, as well as results from in vivo studies on metabolism, bioavailability and efficacy are summarised in this review.

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“…However, 8-PN did not affect MCF-7/6 cells invasion in chick heart fragments in vitro. All these effects were similar to those observed with b-estradiol [78].…”

Section: Antiangiogenic Activity Of Prenylflavonoidssupporting

confidence: 74%

European Journal of Cancer

2007

European Journal of Cancer

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“…Gray of the Annonaceae (Kitaoka et al, 1998). Subsequent investigations in vitro followed, and to date 8PN has generally been shown to mimic the action of 17β-estradiol, albeit with a lesser (10-to 20,000-fold) potency (Coldham and Sauer, 2001;Milligan et al, 2002;Milligan et al, 2000;Rong et al, 2001;Zierau et al, 2002). It is a potent ligand for the α-estrogen receptor with an IC 50 value in the nanomolar range (Kitaoka et al, 1998), it stimulates the production of alkaline phosphatase in Ishikawa cells (Milligan et al, 1999), and stimulates the growth of estrogen-dependent MCF7 (Kitaoka et al, 1998) breast cancer cells.…”

Section: Estrogenic Activitymentioning

confidence: 99%

The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on estrogenic properties

2006

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SummaryAs the population ages, there is an ever-increasing need for therapeutic agents that can be used safely and efficaciously to manage symptoms related to postmenopausal estrogen deficiency. Endogenous estrogens, e.g., 17β-estradiol, of exogenous mammalian origin, e.g., horses, have long been used to manage such symptoms. There are more than twenty different classes of phytochemicals that have demonstrated affinity for human estrogen receptors in vitro. Some studies on exogenous estrogenic substances of botanical origin ("phytoestrogens"), such as standardized formulations of plant extracts with in vitro and in vivo estrogenic activity from soy (Glycine max Merill.) and red clover (Trifolium pratense L.), suggest clinical efficacy. Few clinical data for phytoestrogens other than isoflavonoids are available. In an exhaustive review of the literature through 2003, only two clinical trials were identified that were designed to evaluate the effect of hops (Humulus lupulus L.) on symptoms related to manopause. Folkloric, chemical, and biological literature relating primarily to the use of hops for their estrogenic activity, and two human clinical trials, are reviewed.

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“…These interesting properties have led to intense research aiming at deciphering various bioactivities. 8-PN showed in vivo estrogenic activity (4,5), prevented bone loss in rats (6), inhibited angiogenesis (7) and metastasis (8), and exhibited antiandrogenic activity (9).…”

Section: Introductionmentioning

confidence: 99%

Activation of Proestrogens from Hops (Humulus lupulus L.) by Intestinal Microbiota; Conversion of Isoxanthohumol into 8-Prenylnaringenin

Possemiers

Heyerick

Robbens

et al. 2005

J. Agric. Food Chem.

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165

161

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Hop, an essential ingredient in most beers, contains a number of prenylflavonoids, among which 8-prenylnaringenin (8-PN) would be the most potent phytoestrogen currently known. Although a number of health effects are attributed to these compounds, only a few reports are available about the bioavailability of prenylflavonoids and the transformation potency of the intestinal microbial community. To test these transformations, four fecal samples were incubated with xanthohumol, isoxanthohumol (IX), and 8-PN. Upon incubation with IX, present in strong ales up to 4 mg/L, 36% was converted into 8-PN in one fecal sample and the estrogenic properties of the sample drastically increased. In an experiment with 12 fecal cultures, this conversion was observed in one-third of the samples, indicating the importance of interindividual variability in the intestinal microbial community. Eubacterium limosum was identified to be capable of this conversion (O-demethylation) of IX into 8-PN, and after strain selection, a conversion efficiency of 90% was achieved. Finally, strain supplementation to a nonconverting fecal sample led to rapid and high 8-PN production at only 1% (v/v) addition. Up to now, the concentration of 8-PN in beer was considered too low to affect human health. However, these results show that the activity of the intestinal microbial community could more than 10-fold increase the exposure concentration. Because prenylflavonoids are present in many beers with IX being the major constituent, the results raise the question whether moderate beer consumption might contribute to increased in vivo levels of 8-PN and even influence human health.

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8-Prenylnaringenin, the phytoestrogen in hops and beer, upregulates the function of the E-cadherin/catenin complex in human mammary carcinoma cells

Cited by 40 publications

References 19 publications

European Journal of Cancer

European Journal of Cancer

The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on estrogenic properties

Activation of Proestrogens from Hops (Humulus lupulus L.) by Intestinal Microbiota; Conversion of Isoxanthohumol into 8-Prenylnaringenin

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