Estrogenic Activity of the Phytoestrogens Naringenin, 6-(1,1-Dimethylallyl)naringenin and 8-Prenylnaringenin

Zierau, Oliver; Morrissey, Colm; Watson, R. William G.; Schwab, Pia; Kolba, Susanne; Metz, Peter; Vollmer, Günter

doi:10.1055/s-2002-32089

Cited by 108 publications

(92 citation statements)

References 12 publications

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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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Section: Estrogenic Activitymentioning

confidence: 99%

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

2006

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“…On the other hand, high dietary intake from soy PEs has been demonstrated to be connected to positive effects on (peri-)menopausal complaints (Nagata et al, 2001). A group of recently described relatively potent phytoestrogens are of the naringenin type (Milligan et al, 1999;Milligan et al, 2002;Zierau et al, 2002). Especially 8-prenylnaringenin (8-PN) from hops, Humulus lupulus (L.) and beer, initially described as 8-isopentenylnaringenin (Kitaoka et al, 1998) has been characterized as an extremely potent phytoestrogen (Kitaoka et al, 1998;Milligan et al, 1999;Schaefer et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

“…(Seo et al, 1997). We recently have described the estrogenic (Zierau et al, 2002) and Page 4 of 29 A c c e p t e d M a n u s c r i p t antiandrogenic properties of 6-DMAN (Zierau et al, 2003). For both naringenins low toxicity and weak cytostatic properties were reported, making them good candidate molecules for further studies (Tokalov et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

Time dependency of uterine effects of naringenin type phytoestrogens in vivo

Zierau

Kretzschmar

Möller

et al. 2008

Molecular and Cellular Endocrinology

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This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.Page 1 of 29A c c e p t e d M a n u s c r i p t

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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.

164

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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Estrogenic Activity of the Phytoestrogens Naringenin, 6-(1,1-Dimethylallyl)naringenin and 8-Prenylnaringenin

Cited by 108 publications

References 12 publications

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

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

Time dependency of uterine effects of naringenin type phytoestrogens in vivo

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

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