Formation and Accumulation of α-Acids, β-Acids, Desmethylxanthohumol, and Xanthohumol during Flowering of Hops (<i>Humulus lupulus</i> L.)

Keukeleire, Jelle De; Ooms, Geert; Heyerick, Arne; Roldán‐Ruiz, Isabel; Bockstaele, Erik Van; Keukeleire, Denis De

doi:10.1021/jf034263z

Cited by 127 publications

(102 citation statements)

References 9 publications

(16 reference statements)

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“…In general, two major α and β-acids are in hop. The two series comprise, in fact, three constituents differing in the nature of the side chain (De Keukeleire et al, 2003). They are α-acids with three major analogous (cohumulone, humulone and adhumulone) and β-acids also with three major analogous (colupulone, lupulone and adlupulone) with a six-membered ring structure (De Keukeleire et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

Bitter acids from hydroethanolic extracts of Humulus lupulus L., Cannabaceae, used as anxiolytic

Negri¹,

Santi²,

Tabach³

2010

Rev. bras. farmacogn.

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RESUMO:Humulus lupulus L., Cannabaceae, é usada como sedativo e ansiolítico na medicina popular. O método de HPLC-DAD-ESI-MS n representa uma ferramenta poderosa para a análise de produtos naturais, desde que ela fornece o espectro de UV e informações estruturais sobre os constituintes da mistura. O objetivo deste trabalho foi o de caracterizar os constituintes encontrados no extrato hidroalcoólico. Os constituintes 1-9 foram tentativamente caracterizados através do UV/DAD e ionização por electrospray (MS/MS) depois da separação usando fase reversa, tempo de retenção e dados da literatura. Os principais compostos fenólicos (baseados na área dos picos) foram caracterizados como ácido hulupínico (9), coulupona (8), dois alfaácidos amargos oxidados (principais constituintes), um deles sendo um derivado da coumulinona oxidada (5) e o outro um derivado da humulinona oxidada (7), junto com uma procianidina B (3) e os flavonoides rutina (4) e o canferol-7-O-rutinosídeo (6). Esta planta conhecida devido às suas propriedades ansiolíticas e por ser um componente da cerveja, mostrou derivados oxidados de alfa-ácidos, como principais constituintes do extrato hidroalcoólico. Unitermos: Humulus lupulus, flavonoides glicosídeos, derivados de alfa-ácidos amargos oxidados, HPLC/DAD/MS/MS.ABSTRACT: Humulus lupulus L., Cannabaceae, is commonly used as light sedative and anxiolytics in folk medicine. HPLC-DAD-ESI-MS n represents a powerful tool for the analysis of natural products, since it can simultaneously provide a UV chromatogram and significant structural information about compounds in complex mixture. The aim of this work was characterize the constituents present in hydroethanolic extract. Compounds 1-9 were tentatively characterized on the basis of UV, MS/MS, after reversed phase separation, retention time and literature data. The main phenolic compounds (based on peak area) were characterized as hulupinic acid (9), cohulupone (8), two oxidized hop alfa-bitter acids (principal constituents), one being a oxidized cohumulinone (5) and the other an oxidized humulinone (7) derivatives, together with a procyanidin dimer B (3), flavonoids rutin (4) and kaempferol-7-O-rutinoside (6). This plant known, due to anxiolytic property and beer flavoring, showed oxidized hop bitter acids, as principal constituents, in its hydroethanolic extract.

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Section: Introductionmentioning

confidence: 99%

Bitter acids from hydroethanolic extracts of Humulus lupulus L., Cannabaceae, used as anxiolytic

Negri¹,

Santi²,

Tabach³

2010

Rev. bras. farmacogn.

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“…However, the concentrations detected in beer (and, therefore, the average intake) significantly depend on the brewing process, as strong ales contain up to 4 mg/L. Although X is present as a predominant prenylchalcone [up to 1% (m/ m)] (14), most of it is transformed into IX by thermal isomerization during wort boiling. As a result, IX is the major prenylflavonoid found in beer in concentrations from 500 µg/L (lager/pilsner) up to 4 mg/L (strong ale) (13,15).…”

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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162

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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“…osvald (1946), Sachl (1961Sachl ( ), rybáček (1980 report that pruning retardation in Saaz hop shifts butonization period, hop maturation and plants thus get into less favourable period for alpha-bitter acids formation. according to De Keukeleire et al (2003), each hop cultivar has its individual accumulation period of alpha-bitter acids. alphabitter acids are the most important components of hop; they ensure typical bitter taste of beer and belong among basic criteria of hop quality for beer production.…”

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confidence: 99%

Response of the Czech hybrid hop cultivar Agnus to the term of pruning, depth of pruning and number of trained bines

Křivánek¹,

Kudrna²

2008

PLANT SOIL ENVIRON

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ABSTRACTagnus is a Czech hybrid hop cultivar and a statistically significant influence of depth and term of pruning on harvested hop cones yield and on alpha-bitter acids content in hop cones were found in this study. Evaluated agrotechnical measures, i.e. depth of pruning, term of pruning and number of trained bines, considerably influenced performance and quality of newly grown hop genotype. Every year, we found a positive influence of shallow pruning on yield (increase of dry hop cones yield in 2003 by 0.37 t/ha, in 2004 by 0.28 t/ha and in 2005 by 0.02 t/ha). The hop yield of plants treated with shallow pruning increased on average by 11.6% in three years. We proved a statistically significant influence of three-bines training system on one hop pole, i.e. 3 + 3 bines from each plant. We found that alpha-bitter acids content corresponds with cones yield and indicates a convenience of shallow pruning. Pruning term influenced alpha-bitter acids yield and dynamics of their formation (in the first pruning term yield it was 155 kg/ha, in the second pruning term it was 169 kg/ha, and in the third pruning term it was 175 kg/ha).

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Formation and Accumulation of α-Acids, β-Acids, Desmethylxanthohumol, and Xanthohumol during Flowering of Hops (Humulus lupulus L.)

Cited by 127 publications

References 9 publications

Bitter acids from hydroethanolic extracts of Humulus lupulus L., Cannabaceae, used as anxiolytic

Bitter acids from hydroethanolic extracts of Humulus lupulus L., Cannabaceae, used as anxiolytic

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

Response of the Czech hybrid hop cultivar Agnus to the term of pruning, depth of pruning and number of trained bines

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