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Hop cones preparations possess a wide range of biological activities including antimicrobial properties. In this work, we evaluated the effect of various organic extracts obtained from spent hops, as well as six hops flavonoids and their twenty natural and synthetic derivatives on human and plant microbial pathogens. Methylene chloride, acetone, ethyl acetate, and methanol were used as extractants. Seven flavonoids, among them two natural (α,β-dihydroxanthohumol and 8-prenylnaringenin) showed significant activity against methicillin sensitive and resistant Staphylococcus aureus and Staphylococcus epidermidis strains with the lowest MIC80 value of 0.5 µg/mL. The crude ethyl acetate, acetone, and methanol extracts from the spent hops exhibited antifungal activity against Fusarium oxysporum, F. culmorum, and F. semitectum with the lowest MIC50 of 0.5 mg/mL, while the methylene chloride extract exerted antifungal activity against Botrytis cinerea with the MIC50 of 1 mg/mL. The preparation obtained after the removal of xanthohumol from the spent hops crude extracts retained up to 95% of activity. These findings suggest that various spent hops extracts may be effective agents for the control of plant pathogens of economic importance, like Botrytis cinerea and Fusarium oxysporum, while some compounds from spent hops or their derivatives may become useful for staphylococcal infections.

There is a wide range of information available on by-product disposal methods used by large national breweries. However, little information is available on the methods of by-product disposal used by craft breweries. An investigation was carried out in which 200+ British craft brewers were contacted, of which 90 craft brewers provided basic information about their brewery operations and by-product disposal. Representatives of eleven breweries were interviewed to provide an in-depth case study of their by-product disposal methods. The research found that urban craft brewers use a wider range of disposal methods compared to rural craft brewers; urban brewers dispose of more waste through sewage and landfill, as well as using external companies, such as bio-recycling and anaerobic digester plants, whereas rural brewers have relationships with farmers who dispose of the by-products in various ways. Craft brewers tend to have a direct relationship with the by-product users. Even though they do not have all disposal options available to them which the large industrial breweries have, due to their small scale of by-product production, craft brewers appear to find alternative means of sustainability.

Spent hops from the supercritical extraction process represent a valuable source of xanthohumol (XN), a prenylated flavonoid with demonstrated anticancer, antidiabetic, antibacterial, and anti-inflammatory properties. However, XN is thermally sensitive and readily isomerizes into the less bioactive iso-XN at elevated temperatures, necessitating mild extraction conditions. Previous studies have shown that the pretreatment of plant biomass can enhance the extraction efficiency of bioactive compounds. In this study, various pretreatment methods—including physical (freeze–thaw, ultrasound, and microwave), chemical (acid and base hydrolysis), and enzymatic approaches—were applied to spent hops prior to extraction, and XN yields were compared to those obtained from untreated samples. The experiments, performed in triplicate, yielded meaningful results which helped understand the raw material’s behavior in applied conditions. Due to the compound’s high thermal sensitivity, ultrasound and microwave pretreatments require precise control to prevent excessive temperature increases, making low-temperature methods more suitable. Additionally, exposure to elevated pH adversely affected XN extraction efficiency, limiting the applicability of strong alkaline pretreatments. Among the evaluated methods, freeze–thaw pretreatment proved to be a simple and effective strategy, enhancing XN extraction yields by up to 10.7 ± 0.7% through the optimization of soaking time, the solid-to-liquid ratio, and the thawing temperature. Identifying an inexpensive and efficient pretreatment method could reduce extraction time while improving yield, contributing to the sustainable utilization of spent hops as an XN source.

Synthesis of minor prenylflavonoids found in hops and their non-natural derivatives were performed. The antiproliferative activity of the obtained compounds against some human cancer cell lines was investigated. Using xanthohumol isolated from spent hops as a lead compound, a series of minor hop prenylflavonoids and synthetic derivatives were obtained by isomerization, cyclisation, oxidative-cyclisation, oxidation, reduction and demethylation reactions. Three human cancer cell lines—breast (MCF-7), prostate (PC-3) and colon (HT-29)—were used in antiproliferative assays, with cisplatin as a control compound. Five minor hop prenyl flavonoids and nine non-natural derivatives of xanthohumol have been synthetized. Syntheses of xanthohumol K, its dihydro- and tetrahydro-derivatives and 1″,2″,α,β-tetrahydroxanthohumol C were described for the first time. All of the minor hops prenyl flavonoids exhibited strong to moderate antiproliferative activity in vitro. The minor hops flavonoids xanthohumol C and 1″,2″-dihydroxanthohumol K and non-natural 2,3-dehydroisoxanthohumol exhibited the activity comparable to cisplatin. Results described in the article suggest that flavonoids containing chromane- and chromene-like moieties, especially chalcones, are potent antiproliferative agents. The developed new efficient, regioselective cyclisation reaction of the xanthohumol prenyl group to 1″,2″-dihydroxantohumol K may be used in the synthesis of other compounds with the chromane moiety.

Iron oxide nanoparticles (IONPs) have many practical applications, ranging from environmental protection to biomedicine. IONPs are being investigated due to their high potential for antimicrobial activity and lack of toxicity to humans. However, the biological activity of IONPs is not uniform and depends on the synthesis conditions, which affect the shape, size and surface modification. The aim of this work is to synthesise IONPs using a mixed method, i.e., chemical co-precipitation combined with biogenic surface modification, using extracts from spent hops (Humulus lupulus L.) obtained as waste product from supercritical carbon dioxide hop extraction. Different extracts (water, dimethyl sulfoxide (DMSO), 80% ethanol, acetone, water) were further evaluated for antioxidant activity based on the silver nanoparticle antioxidant capacity (SNPAC), total phenolic content (TPC) and total flavonoid content (TFC). The IONPs were characterised via UV-vis spectroscopy, scanning electron microscopy (SEM), energy-dispersive spectrometry (EDS) and Fourier-transform infrared (FT-IR) spectroscopy. Spent hop extracts showed a high number of flavonoid compounds. The efficiency of the solvents used for the extraction can be classified as follows: DMSO > 80% ethanol > acetone > water. FT-IR/ATR spectra revealed the involvement of flavonoids such as xanthohumol and/or isoxanthohumol, bitter acids (i.e., humulones, lupulones) and proteins in the surface modification of the IONPs. SEM images showed a granular, spherical structure of the IONPs with diameters ranging from 81.16 to 142.5 nm. Surface modification with extracts generally weakened the activity of the IONPs against the tested Gram-positive and Gram-negative bacteria and yeasts by half. Only the modification of IONPs with DMSO extract improved their antibacterial properties against Gram-positive bacteria (Staphylococcus epidermidis, Staphylococcus aureus, Micrococcus luteus, Enterococcus faecalis, Bacillus cereus) from a MIC value of 2.5–10 mg/mL to 0.313–1.25 mg/mL.

Spent hops is a waste produced in large amount by the brewing industry. Rhyzopertha dominica and Sitophilus granarius are insects that cause important economic losses of stored foods. In this study, for the first time, spent hops has been evaluated as a source of essential oil (EO) and chemicals with repellent activity against R. dominica and S. granarius. Spent hops EO yield was 0.11 %. The terpenes myrcene, α-humulene, and β-caryophyllene were its main components (47 %). Spent hops EO RD₅₀ values were 0.01 and 0.19 μL cm⁻² for R. dominica and S. granarius, respectively. Among the chemicals, myrcene was able to exert the highest repellency against R. dominica (RD₅₀ = 0.27 µM cm⁻²), while limonene was the most effective compound against S. granarius (RD₅₀ = 0.89 µM cm⁻²). These results indicate spent hops as an excellent source of EO and chemicals to be utilized as low-cost, eco-friendly insect pests repellents in the protection of stored food.

The main aim of this review was to check for the applicability of the concept of circular economy to brewing chain. By analyzing the beer brewing process, it was possible to identify the main brewery wastes formed and packaging materials used as well as their range of composition and yields. In order to reduce the contribution of packaging material to the carbon footprint of beer, it would be necessary to replace one-way containers used nowadays with lighter, reusable, or recycled ones. Even if the contribution of beer consumption phase was taken into account, there was no definitive solution about the less environmentally impacting beer packaging format. The direct management of polyethylene terephthalate (PET) packaging for liquid foodstuffs could make available 100% recycled PET flakes to be reconverted into food-grade bottles with minimum downcycling to other non-food usage. The countless potential uses of brewery wastes in nutritional and biotechnological fields were tested in laboratory by disregarding any cost–benefit or market analysis. This was mainly because the estimated market price of dried brewer’s spent grain (BSG) resulted to be about 450% higher than that of conventional lignocellulose residues. All the alternative uses hailed in the literature appeared to be more useful for publishing articles than for defining any economically feasible reusing procedure for all brewery wastes. Owing to their high moisture content, such wastes are so perishable as to prevent their safe usage in the human food chain. Currently, their use as-is in animal feeding is the disposal method not only economically feasible but also able to reduce the greenhouse gas load of beer packed in glass bottles (GB) by about one-third of that associated with packaging materials. Not by chance, it is practiced by most industrial and craft breweries.

(1) Background: Over 90% of hop crops are currently used in beer production, with a small part used in the cosmetics and pharmaceutical industries. Spent hops as a waste product contain one of the strongest antioxidants, xanthohumol. The aim of the study was to purify spent hop extracts by magnetic dispersive extraction using iron oxide nanoparticles (IONP) to obtain pure xanthohumol; (2) Methods: The extract from the waste product obtained after supercritical carbon dioxide extraction of hops was prepared by ultrasound-assisted extraction utilizing different solvents, i.e., ethyl acetate, propanol, acetone, 80% methanol, ethyl acetate-methanol (1:1, v/v), and propanol-methanol (1:1, v/v). The hydrodynamic diameters and zeta potential of IONPs before and after incubation were measured by dynamic light scattering (DLS). The extracts were analyzed by reversed-phase high-performance liquid chromatography (HPLC). Isolated xanthohumol was identified based on the DAD spectrum in the range of 200–600 nm and by Fourier transform infrared spectroscopy/attenuated total reflectance (FT-IR/ATR); The antioxidant activity of extracts before and after incubation with IONPs was assessed using SNPAC (Silver Nanoparticle Antioxidant Capacity), DPPH (2,2-diphenyl-1-picrylhydrazyl radical), and FRAP (Ferric Reducing Antioxidant Power) assays, as well as total phenolic content (TPC) and total flavonoid content (TFC). (3) Results: The amount of added IONPs, the kind of solvent, and the contact time of the extract with nanoparticles were optimized. We found that 80% MeOH extract after incubation with IONPs (865 µg IONPs/g of spent hops) at room temperature for 48 h contains 74.61% of initial xanthohumol content, providing a final xanthohumol concentration of 43 µg mL−1. (4) Conclusions: The proposed method of magnetic dispersive extraction using IONPs allows for the purification of spent hops extract and obtaining a pure product, namely xanthohumol, with a wide potential for practical applications in medicine, pharmacy, cosmetics, and agriculture. This is clear evidence of the usefulness of IONP as an effective sorbent. The method allows the use of residues from the brewing industry, i.e., the biomass of used hop cones to obtain a valuable substance.

Brewer’s spent grain (BSG) and brewer’s spent hops (BSH) are the major solid by-products of the brewing industry. The present work evaluated their potential as an alternative source of natural antioxidants. The efficacy of different solvents (MilliQ water, 0.75% NaOH, 50% MeOH, 50% MeOH + 0.3% HCl and 50% Acetone) for extracting polyphenols of these by-products was firstly evaluated, with NaOH showing the best results. The extraction conditions were optimized using the response surface methodology, and were determined to be 1.45% NaOH and 80 °C. BSG extracts showed the highest total polyphenol content (24.84–38.83 µmol GAE/g), whereas the BSH showed the lowest value (24.84 ± 1.55 µmol GAE/g). In general, BSG extracts presented significantly higher antioxidant capacity (ABTS, ORAC). Ferulic acid was the main polyphenol in all BSG extracts (156.55–290.88 mg/100 g), whereas in BSH, this compound was not detected. The addition of 10% BSG extract in o/w emulsions (stored 14 days) showed a reduction in the formation of primary oxidation products of 97%. In the emulsions covered with polylactic acid active films (1% BSG), this reduction corresponded to 35%. Hence, this study demonstrates the potential of these by-products as natural antioxidant sources for protecting food systems against oxidation.

Xanthohumol, a prenylated flavonoid from hops, and a supercritical carbon dioxide extract of spent hops were studied for their antifeedant activity against stored product insect pests: Sitophilus granarius L., Tribolium confusum Duv. and Trogoderma granarium Everts. Xanthohumol exhibited medium deterrent activity against the adults of S. granarius L. and larvae of T. confusum Duv. The spent hops extract was more active than xanthohumol towards the adults of T. confusum Duv. The potential application of the crude spent hops extract as a feeding deterrent against the stored product pests is proposed.