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Activation of proestrogens from hops (Humulus lupulus L.) by intestinal microbiota; Conversion of isoxanthohumol into 8-prenylnaringenin

Sam Possemiers UGent, Arne Heyerick UGent, Veerle Robbens, Denis De Keukeleire UGent and Willy Verstraete UGent (2005) JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. 53(16). p.6281-6288
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
journal title
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
J. Agric. Food Chem.
volume
53
issue
16
pages
6281-6288 pages
publisher
AMER CHEMICAL SOC
Web of Science type
Article
Web of Science id
000231047100018
JCR category
FOOD SCIENCE & TECHNOLOGY
JCR impact factor
2.507 (2005)
JCR rank
2/93 (2005)
JCR quartile
1 (2005)
ISSN
0021-8561
DOI
10.1021/jf0509714
language
English
UGent publication?
yes
classification
A1
id
350431
handle
http://hdl.handle.net/1854/LU-350431
date created
2006-01-26 09:52:00
date last changed
2010-03-12 14:39:24
@article{350431,
  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.},
  author       = {Possemiers, Sam and Heyerick, Arne and Robbens, Veerle and De Keukeleire, Denis and Verstraete, Willy},
  issn         = {0021-8561},
  journal      = {JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY},
  language     = {eng},
  number       = {16},
  pages        = {6281--6288},
  publisher    = {AMER CHEMICAL SOC},
  title        = {Activation of proestrogens from hops (Humulus lupulus L.) by intestinal microbiota; Conversion of isoxanthohumol into 8-prenylnaringenin},
  url          = {http://dx.doi.org/10.1021/jf0509714},
  volume       = {53},
  year         = {2005},
}

Chicago
Possemiers, Sam, Arne Heyerick, Veerle Robbens, Denis De Keukeleire, and Willy Verstraete. 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.
APA
Possemiers, S., Heyerick, A., Robbens, V., De Keukeleire, D., & Verstraete, W. (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.
Vancouver
1.
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. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. AMER CHEMICAL SOC; 2005;53(16):6281–8.
MLA
Possemiers, Sam, Arne Heyerick, Veerle Robbens, et al. “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 (2005): 6281–6288. Print.