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Metabolism of hop-derived bitter acids

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Abstract
In this study, in vitro metabolism of hop-derived bitter adds was investigated. Besides their well-known use as bitter compounds in beer, in several studies, bioactive properties have been related to these types of molecules. However, scientific data on the absorption, distribution, metabolism, and excretion aspects of these compounds are limited. More specific, in this study, alpha-acids, beta-acids, and iso-alpha-acids were incubated with rabbit microsomes, and fractions were subjected to LC-MS/MS analysis for identification of oxidative biotransformation products. Metabolism of beta-acids was mainly characterized by conversion into hulupones and the formation of a series of tricyclic oxygenated products. The most important metabolites of alpha-acids were identified as humulinones and hulupones. Iso-alpha-acids were found to be primarly metabolized into cis- and trans-humulinic adds, next to oxidized alloiso-alpha-acids. Interestingly, the phase I metabolites were highly similar to the oxidative degradation products in beer. These findings show a first insight into the metabolites of hop-derived bitter adds and could have important practical implications in the bioavailability aspects of these compounds, following ingestion of hop-based food products and nutraceuticals.
Keywords
iso-alpha-acids, beta-acids, metabolism, liver microsomes, ISO-ALPHA-ACIDS, HUMULUS-LUPULUS L., TRANSFORMATION PRODUCTS, LIQUID-CHROMATOGRAPHY, OXIDATION-PRODUCTS, LIGHTSTRUCK FLAVOR, MASS-SPECTROMETRY, BEER, ISOHUMULONES, DEGRADATION, alpha-acids, hop bitter acids

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Chicago
Cattoor, Ko, Michael Dresel, Lies De Bock, Koen Boussery, Jan Van Bocxlaer, Jean Paul Remon, Denis De Keukeleire, Dieter Deforce, Thomas Hofmann, and Arne Heyerick. 2013. “Metabolism of Hop-derived Bitter Acids.” Journal of Agricultural and Food Chemistry 61: 7916–7924.
APA
Cattoor, K., Dresel, M., De Bock, L., Boussery, K., Van Bocxlaer, J., Remon, J. P., De Keukeleire, D., et al. (2013). Metabolism of hop-derived bitter acids. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 61, 7916–7924.
Vancouver
1.
Cattoor K, Dresel M, De Bock L, Boussery K, Van Bocxlaer J, Remon JP, et al. Metabolism of hop-derived bitter acids. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. 2013;61:7916–24.
MLA
Cattoor, Ko, Michael Dresel, Lies De Bock, et al. “Metabolism of Hop-derived Bitter Acids.” JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 61 (2013): 7916–7924. Print.
@article{4183933,
  abstract     = {In this study, in vitro metabolism of hop-derived bitter adds was investigated. Besides their well-known use as bitter compounds in beer, in several studies, bioactive properties have been related to these types of molecules. However, scientific data on the absorption, distribution, metabolism, and excretion aspects of these compounds are limited. More specific, in this study, alpha-acids, beta-acids, and iso-alpha-acids were incubated with rabbit microsomes, and fractions were subjected to LC-MS/MS analysis for identification of oxidative biotransformation products. Metabolism of beta-acids was mainly characterized by conversion into hulupones and the formation of a series of tricyclic oxygenated products. The most important metabolites of alpha-acids were identified as humulinones and hulupones. Iso-alpha-acids were found to be primarly metabolized into cis- and trans-humulinic adds, next to oxidized alloiso-alpha-acids. Interestingly, the phase I metabolites were highly similar to the oxidative degradation products in beer. These findings show a first insight into the metabolites of hop-derived bitter adds and could have important practical implications in the bioavailability aspects of these compounds, following ingestion of hop-based food products and nutraceuticals.},
  author       = {Cattoor, Ko and Dresel, Michael and De Bock, Lies and Boussery, Koen and Van Bocxlaer, Jan and Remon, Jean Paul and De Keukeleire, Denis and Deforce, Dieter and Hofmann, Thomas and Heyerick, Arne},
  issn         = {0021-8561},
  journal      = {JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY},
  language     = {eng},
  pages        = {7916--7924},
  title        = {Metabolism of hop-derived bitter acids},
  url          = {http://dx.doi.org/10.1021/jf300018s},
  volume       = {61},
  year         = {2013},
}

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