Functional Properties of Hop Polyphenols

Keukeleire, Denis De; Cooman, Luc De; Rong, Haojing; Heyerick, Arne; Kalita, Jatin; Milligan, S. R.

doi:10.1007/978-1-4615-4139-4_41

Cited by 35 publications

(34 citation statements)

References 34 publications

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“…Dietary factors affording protection against hormone-dependent cancers in vegetarians may well be related to the consumption of high levels of phytoestrogens, which may, therefore, constitute an alternative therapy for such diseases. Hops (Humulus lupulus L.) are mainly applied as an essential raw material for the brewing of beer, but it has since long been known that the plant possesses varying medicinal properties [7]. Recently, we have been successful in isolating and identifying a flavanone, (S)-8-prenylnaringenin Table I; 5,7,4'-trihydroxy-8-(3-methylbut-2-enyl)flavanone], as the main estrogenic principle in hops [8].…”

Section: Introductionmentioning

confidence: 99%

Quantitation of 8-prenylnaringenin, a novel phytoestrogen in hops (Humulus lupulus L.), hop products, and beers, by benchtop HPLC-MS using electrospray ionization

et al. 2000

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Summary8-Prenylnaringenin (8-PN), a potent phytoestrogen, present in hops (Humulus lupulus L.), hop products, and most beers, exhibits an estrogenic activity greater than that of any of the known phytoestrogens. A sensitive, selective, and robust analytical method, based on HPLC-MS (High Performance Liquid Chromatography -Mass Spectrometry) using atmospheric pressure electrospray ionization, has been developed for systematic investigation of the development and the localization of this estrogenic trait in the hop plant, as well as for quantitative determination of 8-PN in hop varieties, hop products, and beers. Excellent linearity was obtained in the range of 3.7-2,200 #g L -1 (7 = 0.9999, n = 7) and the limit of detection was ca. 1 pg L -1. Recoveries were between 93.8% (ll0#g L q) and 96.5% (370#g L 1) for hop products, and between 63.4 % (18.5 #g L -1) and 72.8 % (37 #g L 1) for beers. Good precision was achieved with relative standard deviations of less than 5 % within-day (n = 6) and less than 10 % from-day-to-day (n = 18).

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Section: Introductionmentioning

confidence: 99%

Quantitation of 8-prenylnaringenin, a novel phytoestrogen in hops (Humulus lupulus L.), hop products, and beers, by benchtop HPLC-MS using electrospray ionization

et al. 2000

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“…± 8-Prenylnaringenin and 6-prenylnaringenin, two phytoestrogens from hops [16] [17], are side products formed through the spontaneous cyclization of demethylxanthohumol (4) [18], which is the precursor of potent phytoestrogens and a key intermediate in the synthesis of possible new derivatives of 8-prenylnaringenin. 8-Prenylnaringenin and other prenylated flavonoids showed strong estrogenic activity, whereas no estrogenicity was found in xanthohumol and demethylxanthohumol (4) [19] [20].…”

mentioning

confidence: 97%

Synthesis of Demethylxanthohumol, a New Potent Apoptosis-Inducing Agent from Hops

Diller

Riepl

Rose

et al. 2005

C&B

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Starting from commercially available phloracetophenone (= 1-(2,4,6-trihydroxyphenyl)ethanone), we synthesized demethylxanthohumol (4), a derivative of xanthohumol, devoid of 6'-O-methyl group. Both are prenylchalcones derived from hops (Humulus lupulus). The synthesis was accomplished by an aldol condensation between MOM-protected acetophenone 2 and MOM-protected benzaldehyde 3. The resulting demethylxanthohumol (4) displayed antiproliferative properties. Demethylxanthohumol (4) induced also apoptosis via the mitochondrial pathway in BJAB cells (Burkitt lymphoma cell line) and in primary lymphoblasts of childhood acute lymphoblastic leukemia (ALL).

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“…Polyphenol compounds of malt (Kaneda et al1995;Boivin 2008) and hops (Lermusieau et al 2001;Mikyška et al 2011) affect the antioxidative activity and sensorial stability of beer. According to the literature, some 70-80% polyphenols in beer come from malt, 20-30% being hops polyphenols (De Keukeleire 1999). Polyphenol antioxidants exert significant effects on the sensorial aging of beer and contribute to the beneficial effects of beer drinking.…”

Section: Advanced Studies Of Chemical Profile Of the Czech Beermentioning

confidence: 99%

The phenomenon of Czech beer: a review

Olšovská¹,

Čejka²,

Sigler³

et al. 2014

Czech J. Food Sci.

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Olšovská J., Čejka P., Sigler K., Hönigová V. (2014): The phenomenon of Czech beer: a review. Czech J. Food Sci., 32: 309-319.The character and authenticity of the Czech beer, which has been accorded the protected geographical indication (PGI) České pivo by the EU, are based on specific technology and use of unique raw materials. A number of chemical and sensorial markers of the Czech beer differ from those of other lager or Pils-type beers. The majority of Czech beers contain residual (unfermented) extract. One of the most typical characteristics of Czech beers is the difference in attenuation; its long-term recorded limit value is 4.5%. Another important characteristic typical of the Czech beer is bitterness, which is mostly higher in comparison with other lagers, with the limit value at 29 EBC units. Also the colour, pH, and total polyphenol content are higher in the Czech-type beer. The limit parameters obtained by long-term monitoring were 11.8 EBC, 4.52 and 153 mg/l, respectively. Differences in amino acid and protein profiles and contents were also observed.

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Functional Properties of Hop Polyphenols

Cited by 35 publications

References 34 publications

Quantitation of 8-prenylnaringenin, a novel phytoestrogen in hops (Humulus lupulus L.), hop products, and beers, by benchtop HPLC-MS using electrospray ionization

Quantitation of 8-prenylnaringenin, a novel phytoestrogen in hops (Humulus lupulus L.), hop products, and beers, by benchtop HPLC-MS using electrospray ionization

Synthesis of Demethylxanthohumol, a New Potent Apoptosis-Inducing Agent from Hops

The phenomenon of Czech beer: a review

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