Comprehensive Sensomics Analysis of Hop-Derived Bitter Compounds during Storage of Beer

Intelmann, Daniel; Haseleu, Gesa; Dunkel, Andreas; Lagemann, Annika; Stephan, Andreas; Hofmann, Thomas

doi:10.1021/jf104392y

Cited by 67 publications

(92 citation statements)

References 35 publications

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“…Other compounds originating from hops, such as reduced derivatives of IAAs and prenylated phenols have been suggested previously as urinary and blood biomarkers of beer intake 13,31,46 . Isoxanthohumol was shown to be stable even after 10 years of storage, making it a suitable biomarker candidate.…”

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confidence: 87%

Detecting Beer Intake by Unique Metabolite Patterns

et al. 2016

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Evaluation of the health related effects of beer intake is hampered by the lack of accurate tools for assessing intakes (biomarkers). Therefore, we identified plasma and urine metabolites associated with recent beer intake by untargeted metabolomics and established a characteristic metabolite pattern representing raw materials and beer production as a qualitative biomarker of beer intake. In a randomized, crossover, single-blinded meal study (MSt1), 18 participants were given, one at a time, four different test beverages: strong, regular, and nonalcoholic beers and a soft drink. Four participants were assigned to have two additional beers (MSt2). In addition to plasma and urine samples, test beverages, wort, and hops extract were analyzed by UPLC-QTOF. A unique metabolite pattern reflecting beer metabolome, including metabolites derived from beer raw material (i.e., N-methyl tyramine sulfate and the sum of iso-α-acids and tricyclohumols) and the production process (i.e., pyro-glutamyl proline and 2-ethyl malate), was selected to establish a compliance biomarker model for detection of beer intake based on MSt1. The model predicted the MSt2 samples collected before and up to 12 h after beer intake correctly (AUC = 1). A biomarker model including four metabolites representing both beer raw materials and production steps provided a specific and accurate tool for measurement of beer consumption.

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confidence: 87%

Detecting Beer Intake by Unique Metabolite Patterns

et al. 2016

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“…Similarly, M2 was identified as 1- (Okada et al, 2004;Bohr et al, 2005) by comparison of its LC-MS and high-resolution MS data with those of authentic reference material (Intelmann et al, 2011). Metabolites of strawberry 'Senga Sengana' were also analyzed to identify additional phloroglucinol derivatives in Fragaria spp.…”

Section: Apgs Are Unique Fragaria Spp Metabolites That Differentiallmentioning

confidence: 99%

“…3). M4 was identified by comparing its retention time and mass spectra (Ms and Ms2) and high-resolution mass spectra with those of the authentic compound (Intelmann et al, 2011).…”

Section: Apgs Are Unique Fragaria Spp Metabolites That Differentiallmentioning

confidence: 99%

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Acylphloroglucinol biosynthesis in strawberry fruit

et al. 2015

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ORCID IDs: 0000-0001-6609-7034 (J.S.); 0000-0002-9753-3967 (W.S.).Phenolics have health-promoting properties and are a major group of metabolites in fruit crops. Through reverse genetic analysis of the functions of four ripening-related genes in the octoploid strawberry (Fragaria 3 ananassa), we discovered four acylphloroglucinol (APG)-glucosides as native Fragaria spp. fruit metabolites whose levels were differently regulated in the transgenic fruits. The biosynthesis of the APG aglycones was investigated by examination of the enzymatic properties of three recombinant Fragaria vesca chalcone synthase (FvCHS) proteins. CHS is involved in anthocyanin biosynthesis during ripening. The F. vesca enzymes readily catalyzed the condensation of two intermediates in branched-chain amino acid metabolism, isovaleryl-Coenzyme A (CoA) and isobutyryl-CoA, with three molecules of malonyl-CoA to form phlorisovalerophenone and phlorisobutyrophenone, respectively, and formed naringenin chalcone when 4-coumaroyl-CoA was used as starter molecule. Isovaleryl-CoA was the preferred starter substrate of FvCHS2-1. Suppression of CHS activity in both transient and stable CHSsilenced fruit resulted in a substantial decrease of APG glucosides and anthocyanins and enhanced levels of volatiles derived from branched-chain amino acids. The proposed APG pathway was confirmed by feeding isotopically labeled amino acids. Thus, Fragaria spp. plants have the capacity to synthesize pharmaceutically important APGs using dual functional CHS/ (phloriso)valerophenone synthases that are expressed during fruit ripening. Duplication and adaptive evolution of CHS is the most probable scenario and might be generally applicable to other plants. The results highlight that important promiscuous gene function may be missed when annotation relies solely on in silico analysis.

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“…Alpha-acids are the quantitatively predominating class of polyketides accounting for up to 10% of hops dry matter and comprising of at least six congeners differing in the alkanoyl side chain. Whereas cohumulone, n-humulone, and adhumulone account for more than 98% of the total amount of alpha-acids, the minor congeners, namely, posthumulone, prehumulone, and adprehumulone, reach a relative quantity of less than 2% [1]. Iso-alpha-acids are isomerized forms of the alpha-acids (humulones) from the hops.…”

Section: Introductionmentioning

confidence: 99%

Kinetic Modeling of Hop Acids during Wort Boiling

Huang¹,

Tippmann²,

Becker³

2013

IJBBB

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Abstract-The thermal degradation of iso-alpha-acids was investigated at four pH levels between 4.5 and 6.5 at different boiling temperatures (90-130 °C) during the wort boiling time (0-360 min). The free energy of activation and the reaction rate constant (k) of the degradation of iso-alpha-acids were calculated. Raising pH value from 4.5 to 5.5 and from 5.5 to 6.5 decreased the reaction energy about 20 kJ/mol. The relative proportion of isocohumulone stays almost constant. We developed a kinetic model for the irreversible consecutive reation; iso-alpha-acids are isomerized form of alpha-acids by the application of heat in solution and at the same time iso-alpha-acids are degraded to humulinic acids and other compounds. This kinetic model is useful to calculate time to added hops into boiling kettle.

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Comprehensive Sensomics Analysis of Hop-Derived Bitter Compounds during Storage of Beer

Cited by 67 publications

References 35 publications

Detecting Beer Intake by Unique Metabolite Patterns

Detecting Beer Intake by Unique Metabolite Patterns

Acylphloroglucinol biosynthesis in strawberry fruit

Kinetic Modeling of Hop Acids during Wort Boiling

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