colupulone and lupulon

Hop is widely used in beer brewing and as a medicinal product. The present study comprehensively analyzed the main molecular determinants of the antibacterial activity of hop extracts. Minimum inhibitory concentrations (MIC) against Bacillus subtilis between 31.25 and 250 µg/mL were found in the ethanolic extracts of five hop varieties for beer brewing, but not in the tea hop sample. Activity-guided fractionation revealed the highest antibacterial activity for lupulone and adlupulone (MIC 0.98 µg/mL). Metabolome profiling and subsequent multistep statistical analysis detected 33 metabolites out of 1826 features to be associated with the antibacterial activity including humulone, adhumulone, colupulone, lupulone, and adlupulone. Xanthohumol, the three humulone- and three lupulone congeners were quantified in the hop extracts by a validated ultrahigh-performance liquid chromatography-mass spectrometry method. Considering concentrations and MICs, colupulone and lupulone were identified as major contributors to the antibacterial activity of hop extract with the highest antibacterial activity values (concentration/MIC) of 1.59 and 2.56.

Topics: Anti-Bacterial Agents; Metabolome

Addition of β-acids extracted from hop at different levels (0, 30mgkg

Topics: Animal Feed; Animals; Chickens; Cyclohexanones; Humulus; Meat; Metabolome; Muscle Proteins; Oxidation-Reduction; Terpenes

The efficacy of hops beta acids (HBA) against unstressed and stress-adapted Listeria monocytogenes in ham extract and the consumers' acceptability of HBA on ready-to-eat (RTE) hams were investigated. Unstressed or acid-, cold-, or starvation-stress-adapted L. monocytogenes was inoculated (1.3-1.5 log CFU/mL) into 10% ham extract, without (control) or with HBA (4.44 or 10.0 µg/mL). Survival/growth of the pathogen during storage (7.2 °C, 26 days) was monitored periodically. Sensory evaluation (30 participants, 9-point hedonic scale) was performed with hams dipped into 0.05, 0.11, and 0.23% HBA solution. Ham extracts without HBA supported rapid growth of unstressed and stress-adapted cells with growth rates of 0.39-0.71 log CFU/mL/day and lag phases of 0-3.26 days. HBA inhibited growth of unstressed L. monocytogenes by slowing (P < 0.05) growth rate (0.24-0.29 log CFU/mL/day) and increasing (P < 0.05) length of the lag phase (3.49-12.98 days) compared to control. Acid-, cold-, or starvation-stress-adapted cells showed cross protection against HBA with greater (P < 0.05) growth rates (0.44-0.66 log CFU/mL/day) and similar or shorter lag phases (0-5.44 days) than unstressed cells. HBA did not (P > 0.05) affect sensory attributes of RTE ham. These results are useful for RTE meat processors to develop operational protocols using HBA to control L. monocytogenes.

Topics: Animals; Complex Mixtures; Consumer Behavior; Cyclohexanones; Humans; Humulus; Listeria monocytogenes; Meat; Microbial Viability; Swine; Terpenes

Bitter acids (BAs) from the hop plant Humulus lupulus L. exhibit multiple beneficial biological properties with promising effects in cancer therapy and prevention, but information regarding the effects on hepatocellular carcinoma (HCC) is missing. Here, we used two different hop bitter acid extracts enriched for either α-acids or β-acids to obtain insight into whether biological activity varies between these two groups of BAs. At a concentration of 25 µg/ml, only the β-acid rich started to induce aspartate transaminase (AST) release, and a significant increase was detected with 50 µg/ml of both extracts. Already at lower concentrations both extracts led to a dose-dependent inhibition of proliferation, and migration was suppressed at a concentration as low as 5 µg/ml in HCC cells. The focus on different signaling pathways revealed an inhibition of ERK1/2 phosphorylation, downregulation of AP-1 activity and an alleviation of nuclear factor κB (NFκB) activity in HepG2 cells incubated with 5 µg/ml of both extracts, whereby the β-acid rich extract showed more pronounced effects. In conclusion, we identified ERK1/2, AP-1 and NFκB, which are important factors in tumor development and progression, as targets of hop BAs. Thus, these data suggest the potential use of BAs as functional nutrients for both prevention and treatment of HCC.

Topics: Acids; Antineoplastic Agents, Phytogenic; Aspartate Aminotransferases; Carcinoma, Hepatocellular; Cell Movement; Cell Proliferation; Cyclohexanones; Cyclohexenes; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Humans; Humulus; Liver Neoplasms; Mitogen-Activated Protein Kinase 1; Mitogen-Activated Protein Kinase 3; NF-kappa B; Phosphorylation; Plant Extracts; Terpenes; Transcription Factor AP-1; Tumor Cells, Cultured

Hops beta acids (HBA) are parts of hops flowers used to preserve wort and provide flavor in beer, and are reported as having antimicrobial properties. This study evaluated the antilisterial activity of HBA alone or in combination with other known antimicrobials in a culture broth medium. Listeria monocytogenes (10-strain mixture) was inoculated (2.6 to 2.8 log CFU/mL) into tryptic soy broth supplemented with 0.6% yeast extract (TSBYE) without (control) or with HBA (0.5 to 5.0 microg/mL), potassium lactate (1.0%), sodium diacetate (0.25%), or acetic acid (0.1%), alone or in combination with HBA (0.5 to 3.0 microg/mL). Survival/growth of the pathogen during storage at 4 degrees C (35 d), 10 degrees C (20 d), or 25 degrees C (2 d) was periodically monitored by spiral plating onto tryptic soy agar plus 0.6% yeast extract. As expected, TSBYE without antimicrobials (control) supported rapid pathogen growth with growth rates of 0.40, 2.88, and 9.58 log CFU/mL/d at 4, 10, and 25 degrees C, respectively; corresponding Y(end) values exceeded 9.0 log CFU/mL at 35, 20, and 2 d storage. HBA used alone (1.0 to 5.0 microg/mL) inhibited growth of L. monocytogenes at all 3 temperatures, with inhibition being more pronounced at higher concentrations and at the lower storage temperature (4 degrees C). The antilisterial activity of HBA (0.5 to 3.0 microg/mL) was enhanced when combined with sodium diacetate, acetic acid, or potassium lactate, achieving complete inhibition at 4 degrees C when 3.0 microg/mL HBA were used in combination with each of the above antimicrobials. Overall, HBA exhibited promising antilisterial activity in a broth medium and further studies are needed to investigate its potential antilisterial effects in food products.

Topics: Animals; Anti-Bacterial Agents; Beer; Cyclohexanones; Flowers; Humans; Humulus; Listeria monocytogenes; Listeriosis; Meat; Meat Products; Propylene Glycol; Swine; Taste; Temperature; Terpenes