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

Possemiers, Sam, Heyerick, Arne, Robbens, Veerle, De Keukeleire, Dennis and Verstraete, Willy (2005) Activation of Proestrogens from Hops (Humulus lupulus L.) by Intestinal Microbiota; Conversion of Isoxanthohumol into 8-Prenylnaringenin. Journal of Agricultural and Food Chemistry, 53 16: 6281-6288.


Author Possemiers, Sam
Heyerick, Arne
Robbens, Veerle
De Keukeleire, Dennis
Verstraete, Willy
Title Activation of Proestrogens from Hops (Humulus lupulus L.) by Intestinal Microbiota; Conversion of Isoxanthohumol into 8-Prenylnaringenin
Formatted title Activation of Proestrogens from Hops (Humulus lupulus L.) by Intestinal Microbiota; Conversion of Isoxanthohumol into 8-Prenylnaringenin
Journal name Journal of Agricultural and Food Chemistry  (ERA 2012 Listed)    (ERA 2010 Rank A)   Check publisher's open access policy
Publication date 2005-08
Sub-type Article
DOI 10.1021/jf0509714
Volume number 53
Issue number 16
ISSN 0021-8561
1520-5118
Start page 6281
End page 6288
Total pages 8
Place of publication Washington, DC, United States
Publisher American Chemical Society
Language eng
Subject 110801 Medical Bacteriology
Formatted abstract 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.
Keyword Hop
Isoxanthohumol
8-prenylnaringenin
Prenylflavonoids
Intestine
Bacteria
Eubacterium limosum
Beer
Phytoestrogens
O-demethylation
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article
Collections: Excellence in Research Australia (ERA) - Collection
Advanced Water Management Centre Publications
 
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