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![A brief classification of hops cone compounds based on the reviewed literature [16,29,31-36].](publication/343171124/figure/fig1/AS:916630863355905@1595553236744/A-brief-classification-of-hops-cone-compounds-based-on-the-reviewed-literature.jpg)
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Hops (Humulus lupulus L.) are used traditionally in the brewing industry to confer bitterness, aroma, and flavor to beer. However, in recent years, it has been reported that female inflorescences contain a huge variety of bioactive compounds. Due to the growing interest of the consumers by natural ingredients, intense research has been carried out...
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Citations
... Antioxidant and antimicrobial properties of bitter acids offer different applications as food preservatives [80]. For instance, lupulone's addition to the chicken diet enhanced meat quality by protecting myofibrillar proteins from oxidation [81]. ...
Annually, 221 million tons of agro-food by-products are generated worldwide, causing diverse environmental issues due to incorrect discharge. Hot trub, spent hops, brewer's spent grains, and brewer's spent yeast are the by-products produced in the beer manufacturing chain. These by-products contain fibers, proteins, polyphenols, essential oils, and taste compounds, presenting high possibilities of use as alternative raw materials. In this review, we compiled the knowledge gaps of brewing by-product reuse, from phytochemical compound extractions to concentration approaches, mainly concerning bitter acids and polyphenols. Moreover, we assessed and discussed the emerging technologies and alternative solvents that have allowed for higher extraction yields. We illustrated the importance of purification and concentration steps of non-destructive methods for added value in products from reuse approaches. Finally, we showed the relevance of scale-up and economic feasibility studies in order to encourage the implementation of facilities that produce bitter acids and polyphenols from alternative sources such as hot trub and spent hops.
... The use of different hops parts (inflorescences, young branches and shoots) in folk medicine, in traditional cooking and in other fields is well-known [7], and its phytochemistry is extensively documented [4]. Hops contain hundreds of chemical compounds, including some secondary metabolites (polyphenols, resins, terpenes), with potential pharmacological and medicinal value that deserve to be explored [8,9]. ...
In this work, the fresh leaves and inflorescences of Humulus lupulus L. cv. Chinook hops were investigated in order to describe their chemical composition and evaluate their biological activities. The analyses were carried out first on fresh untreated samples and then on pulverized ones using the SPME-GC-MS technique. In total, forty-two molecules belonging to different chemical classes were identified, and among these, twenty-three were terpene compounds. In order to carry out the activity assays, the powders were subjected to extraction with two different solvents (methanol and distilled water) by stirring and subsequent sonication at room temperature. To chemically characterize the extracts, the methanolic ones were analyzed by direct injection into the GC-MS apparatus, while the aqueous ones were analyzed by DI-SPME-GC-MS. In addition, with the aim to obtain information on the non-volatile content of the methanolic extracts, they were also subjected to derivatization, and the silylated derivatives were analyzed by GC-MS. The antioxidant activity was then evaluated by means of DPPH and ABTS assays after the determination of the total content of polyphenols and flavonoids. The greatest effects were observed on the methanolic extracts rather than on the aqueous ones. Furthermore, a preliminary study on the cytotoxic power of the methanolic extracts was also conducted on three different human cancer cell lines, such as non-small cell lung cancer (H1299), melanoma (A375) and breast cancer (MCF7). The obtained results showed that the two extracts induced a marginal effect on reducing breast tumor, melanoma and non-small cell lung cancer cell proliferation.
... humulone (α-acid) and lupulone (β-acid), and terpenes (essential oils), e.g. myrcene and linalool, βcaryophyllene, humulene, linalool, and α-pinene, etc. (Astray et al., 2020). ...
... The strobiles of the female plants are able to develop the lupulin glands that secrete a fine yellow resinous powder. These glands secrete predominantly bitter acids and essential oils, the constituents of which include prenylflavonoids [1,2]. ...
... In Europe, there is evidence of the use of H. lupulus since prehistoric times. The ancient Romans employed its leaves and inflorescences in some food preparations as well as in textiles and cosmetic products [2]. Afterwards, the use of hop rapidly increased in the Middle Ages, presumably because of their developed utilization in the brewing process. ...
... Still, new eco-friendly extraction methods should be developed to increase the yield and the selectivity of the compounds [14]. Natural, deep eutectic solvents and emerging extraction technologies such as ultrasound-assisted, microwave-assisted, pressurized liquid, and supercritical fluid extraction are emerging solutions to the sustainable extraction and isolation of natural compounds [2,18]. ...
Hops (Humulus lupulus L.) are known worldwide as a raw material in beer production due their flavor and preservative values. The beneficial properties of the plant have been mostly associated with the female hop inflorescences (cones), which is also the part used in the brewing industry. However, some studies indicate the presence of compounds associated with health benefits in the vegetative parts of hops or small-caliber cones, which discarded in hop collection. Moreover, large quantities of by-products remain in the forms of spent grains and spent hops/hot trub and are produced by breweries raising environmental and economic sustainability concerns. This review focuses on the phytochemicals and biological and pharmacological activities of hop and their potential use in skin care products and also intends to explore the potential of the hop’ discarded parts and brewery industry by-products for production in the cosmetics industry.
... Hops has also been used traditionally to treat pain, inflammation, anxiety and sleeping disorders and has been shown to have antibacterial, anti-cancer, anti-inflammatory, sedative and hypnotic properties. The active components in hops include numerous polyphenols and bitter acids, with the exact composition depending on the hop variety and climatic conditions during plant growth [234][235][236]. ...
The metabolic and mechanical stresses associated with muscle-fatiguing exercise result in perturbations to bodily tissues that lead to exercise-induced muscle damage (EIMD), a state of fatigue involving oxidative stress and inflammation that is accompanied by muscle weakness, pain and a reduced ability to perform subsequent training sessions or competitions. This review collates evidence from previous research on a wide range of nutritional compounds that have the potential to speed up post-exercise recovery. We show that of the numerous compounds investigated thus far, only two—tart cherry and omega-3 fatty acids—are supported by substantial research evidence. Further studies are required to clarify the potential effects of other compounds presented here, many of which have been used since ancient times to treat conditions associated with inflammation and disease.
... These polyphenolic extracts are attractive ingredients for the cosmetic and pharmaceutical industries due to their beneficial biological properties (Zillich et al., 2015). In cosmetics, hops are used in bath lotions, among others (Cieśliński and Idowski, 2003;Astray et al., 2020). Supercritical CO 2 extracts of hop cones were used to formulate shower gels resulting in enhanced skin-conditioning properties due to their content in bioactive ingredients (Vogt et al., 2014). ...
El aumento de la producción de lúpulo se debe principalmente al auge de las cervecerías artesanales. En la Región de Los Ríos, se han recolectado varios ecotipos locales de lúpulo en los últimos diez años, el ecotipo Ranco es hasta ahora el más distribuido y cultivado en la región. Por ello, es urgente brindar información a productores y consumidores para evaluar el potencial aporte diferenciando la producción local de cerveza artesanal y subproductos de lúpulo. El ecotipo Ranco es una planta en forma de garrote, hojas de tamaño mediano de color verde oscuro, brotes laterales largos en la parte superior de la planta y un tallo con pigmentación antociánica. Los conos son de tamaño mediano, concentrados en el tercio superior de la planta, revelando una madurez media a tardía. Desde el punto de vista agronómico, la planta muestra un crecimiento vigoroso y robusto, pero es susceptible al mildiú (Pseudopernospora humuli) y con baja tolerancia a los ácaros (Tetranychus urticae). El ecotipo Ranco exhibe una prospección de rendimiento en promedio entre 1.000 y 1.350 kg/ha en la Región de Los Ríos, con conos con aroma predominantemente herbáceo y leñoso. Los conos de lúpulo analizados en este estudio presentaron un bajo porcentaje de ácidos amargos, pero en diferentes partes de la planta se detectaron cantidades importantes de polifenoles, lo que sugiere un uso potencial en la industria alimentaria y cosmética, así como en el desarrollo de nuevas variedades regionales de cerveza. Las características morfológicas y químicas presentadas por primera vez de este novedoso ecotipo de lúpulo, aportan conocimientos útiles para fortalecer el desarrollo sustentable de las industrias cerveceras y de productos en base a lúpulo con valor agregado en la Región de Los Ríos.
... 21 The latter is a hop ⊎-acid member of bitter acids, which render the bitter taste in beer, and it is found in Humulus lupulus, a plant widely used in the pharmaceutical and food industry. 22 Extracts from Humulus lupulus have been shown to be toxic against insects and handled as environmentally friendly. [23][24][25][26][27] Among the metabolites found in this plant, hop ⊎-acids, exhibit miticidal activity against the parasite mite Varroa destructor (Acari: Varroidae) of the honey bee (Appis mellifera L.). ...
Background:
As climate change proceeds, the management of the population of mosquitoes becomes more and more challenging. Insect adulticides and larvicides constitute significant control techniques, with the latter being considered the leading mosquito control method. However, the development of mosquito resistance development and the adverse side effects caused by the extensive use of synthetic insecticides have turned research towards the discovery of environmentally-friendly solutions. Plants and bacteria have historically proven to be a good source of insecticidally active compounds, which may possess novel modes of action to overcome current resistance mechanisms and could also possess favorable human and environmental safety profiles. A previous study demonstrated that the naturally occurring prenylated acyl phloroglucinol deoxycohumulone is a potent larvicidal agent against Culex pipiens. Herein the structural characteristics that improve it are explored by evaluating colupulone and novel geranylated analogues.
Results:
Colupulone, a prenylated acyl phloroglucinol isolated from Humulus lupulus, colupone, and novel geranylated acyl phloroglucinol congeners, were synthesized and evaluated against Cx. pipiens larva. Results indicated that selected derivatives exhibited superior potency than deoxycohumulone (LC50 43.7 mg L-1 ). Thus, strong activity was observed for colupulone (LC50 19.7 mg L-1 ), and some novel geranyl analogues of deoxycohumulone reaching at LC50 17.1 mg L-1 , while colupone and similar compounds were almost inactive.
Conclusion:
The results determined the relationship between the target activity and the chemical structure of the tested compounds, and they revealed significantly improved larvicidal candidates. These results highlight the potential of the acyl phloroglucinol chemistry for further development of mosquito larvicides. © 2022 Society of Chemical Industry.
... Together with resins, essential oils, flavonoids and other phenolics, they are involved in numerous biological activities. Since ancient times, hop has been known as a good natural remedy for blood purification, treatment of anxiety and insomnia and appetite stimulation (Astray, Gullón, Gullón, Munekata, & Lorenzo, 2020). ...
... In our study, hop inflorescence components were extracted with 95% hydroalcoholic solution, and according to literature data (Česlová, Holčapek, Fidler, Drštičková, & Lísa, 2009;Cortese, Gigliobianco, Peregrina, Sagratini, Censi, & Di Martino, 2020;Nikolic et al., 2013;Sommella, et al., 2018;Stevens, Taylor, & Deinzer, 1999), LC-MS analysis identified several phenolic compounds with known antioxidant activities ( Table 1). Most of them are able to interact with ROS, to prevent and delay cell damage (Astray, Gullón, Gullón, Munekata, & Lorenzo, 2020). However, the next step to guarantee the safety of natural products is the determination of their toxicity in cell systems. ...
The present study investigated the potential antioxidant applications of Humulus lupulus L. as raw extract and nanoformulated in liposomes. H. lupulus is commonly used as a food ingredient, but it is also a promising source of specialized metabolites with health-promoting effects. In the extract obtained by hydroalcoholic maceration, 24 compounds were characterized using liquid chromatography-mass spectrometry analyses. The extract exhibited an interesting antioxidant activity in in vitro spectrophotometric and cell assays. The extract was nanoformulated into liposomes to exploit and improve its beneficial proprierties. The in vitro assays revealed that, after incorporation into liposomes, the extract’s antioxidant activity was preserved and even improved. Moreover, a lower dose of the extract was required to prevent reactive oxygen species overproduction when included in the nanoformulation. These results confirm the advantages of nanoformulating herbal extract to maximize its health-promoting effects for a potential pharmaceutical application.
... Oxidative stress i portant factor contributing to the development of chronic diseases, and polyphe tracted from enriched plants are widely used as a source of natural antioxidants [1 the years it has been reported about a wide range of further effects, both in viv vitro, including the treatment of diabetes mellitus, anti-carcinogenesis, and cardio diseases [11]. Hop extracts are a valuable source of bioactive (antibacterial, ant cardioprotective, antioxidant, anti-inflammatory and antiviral effects, etc.) com [12,13]. The most abundant prenylated flavonoid existing in hops, xanthohum ( Figure 2), is secreted within the hop resin (lupulin) by glandular trichomes on the surfaces of cone bracts and displays numerous beneficial bioactivities, in partic cluding antioxidant activities [14,15]. ...
... Over the years it has been reported about a wide range of further effects, both in vivo and in vitro, including the treatment of diabetes mellitus, anti-carcinogenesis, and cardiovascular diseases [11]. Hop extracts are a valuable source of bioactive (antibacterial, antifungal, cardioprotective, antioxidant, anti-inflammatory and antiviral effects, etc.) compounds [12,13]. The most abundant prenylated flavonoid existing in hops, xanthohumol (XN) (Figure 2), is secreted within the hop resin (lupulin) by glandular trichomes on the adaxial surfaces of cone bracts and displays numerous beneficial bioactivities, in particular, including antioxidant activities [14,15]. ...
This study evaluates the content of essential oils (EOs) and prenylated flavonoid Xanthohumol (XN) in extracts of Slovenian hops, cultivar Aurora, obtained by using fluids of different polarity. It is a continuation of our previous work, investigating the extraction of bitter acids from hops. Extraction was conducted semi-continuously, using sub- and supercritical fluids of different polarity, i.e., carbon dioxide (CO2) and propane as non-polar and dimethyl ether (DME) as the polar solvent. The experiments explored a temperature range between 20 °C and 80 °C and pressures ranging from 50 bar to 150 bar. The content of XN in extracts was analysed using high-performance liquid chromatography and experiments demonstrated the largest concentration of XN was obtained using DME. In order to analyse the EO components in extracts, connected with a distinct odour, the steam distillation of extracts was performed and GC analysis was employed. Hop oil derived from CO2 extracts at specific conditions, had the highest relative concentration of linalool, β-caryophyllene and α-humulene, and oil derived from propane extracts had the highest content of all other five selected components (myrcene, geraniol, farnesene, α-selinene and δ-cadinene). The relative content of the investigated EO components in DME extracts was similar to that in propane extracts.
... As β-myrcene is a small hydrocarbon molecule, its structure resembles the acyl chain (terminal part) of the membrane steroids. Therefore, when β-myrcene migrates from the beer solution it can pack in the voids between the palmitoyl chains and change their orientation at the yeast/beer interface [48,[51][52][53]. The non-polar β-myrcene may attach to the non-polar surface of the yeast cells [54][55][56]. ...
The production of heavily hopped beers, such as Indian Pale Ale (IPA) styles, has been gaining momentum in recent years in the Central European markets. To this end, the dry hopping process is becoming increasingly popular, mostly in microbreweries, but also with larger manufacturers. In our research, we investigated the dissolution rate of the main volatile component of hops, β-myrcene with a modified dry hopping method. Following the primary fermentation, we applied the dry hopping process, where the weighed hops were chopped and blended into a container with 0.5 L of beer and later added to the young beer. During the dry hopping process, we determined various important parameters of the beer, and we repeated the same measurements for the bottled beer. In the first 96 h of the dry hopping process, we monitored the concentration of β-myrcene so that we managed to determine the dissolution rate constant (k = 0.1946 h-1). The β-myrcene concentration stabilizes after 44 h in the fermenter. At the same time, measurements were conducted for bitterness, pH, CO2 and alcohol content, extract and density during the process. Our experiment demonstrates that a new method of dry hopping provides a much higher concentration of β-myrcene (215 μg/L) than other methods indicated in former studies in the field. A health and safety assessment of β-myrcene was also made and we determined what the safe amount of β-myrcene ingested with IPA beer is. Our modified process was successful, we were able to determine the dissolution rate of β-myrcene, and the recommended daily intake of IPA beer with particular reference to β-myrcene.
