¿Para qué sirve el extracto de lúen la cerveza?

Hops, scientifically known as Humulus lupulus L., also called snake grass, toad lily, Tang grass flower, hu bu, and yeast flower, are plants belonging to the Cannabaceae family within the Urticales order. Hops are dioecious perennial climbing herbs with fibrous roots, capable of growing in many regions worldwide. Most cultivatielareas are concentrated between latitudes 35° and 55° north and south. Currently, the primary production regions are the United States, Europe, Australia, South America, and China.

Hops extract imparts a distinctive bitterness and unique flavor to beer and possesses certain preservative properties, earning it the title of “the soul of beer.” Since its introduction into beer brewing in the 12th century, its primary use remains in beer production. As an important medicinal plant, hops also have a long history of application. Starting in the 13th century, hops, like other herbs such as rosemary, valerian, coriander, and marsh marigold, began to be used as herbal medicine. In the “Compendium of Materia Medica” by Li Shizhen of the Ming Dynasty, the term “Tuo De Hua” refers to hops.

Recent studies have shown that Extractos de lúpulo not only have sedative, calming, hypnotic, antibacterial, anti-inflammatory, and diuretic effects, but also possess multiple functions such as antioxidant, antiviral, antitumor, and phytoestrogenic activities.

1 ingrediente activo de extractos de lú.

Hundreds of different organic compounds have been identified in hop extracts, and their flavor characteristics are produced by the independent yet synergistic interactions of these compounds. Humulone accounts for approximately one-fifth of the dry weight of hops, containing the most important bitter components, hop essential oils, and polyphenolic compounds. el bitter components are composed of α-acids and β-acids, which exist in a soft oil or resinous form and are soluble in hydrocarbon solvents, hence they are commonly referred to as hop soft resins. Due to oxidation by air, hop bitter acids are converted into a complex class of compounds. These compounds are no longer soft and are insoluble in hydrocarbon solvents, and are therefore commonly referred to as hop hard resins. Hops also contain other inorganic and organic compounds, the contents of which in hops are shown in Table 1.

α-Acids are an important component of hops, and they are a class of substances composed of five main isomers: humulone, cohumulone, adhumulone, trans-humulone, and trans-cohumulone. elratio of humulone to cohumulone is highly correlated with the variety of hops and brewing quality. Traditionally, hop varieties are broadly classified into three types based on their α-acid content and flavor characteristics: aromatic hops, bitter hops, and bitter-aromatic hops. In recent years, with the continuous development and promotion of new hop varieties with high α-acid content, the beer industry has placed more stringent requirements on hop quality. Currently, internationally, hops are generally classified into four major categories: premium aromatic hops, aromatic hops, bitter hops, and high α-acid hops [11-12]. The classification characteristics and representative varieties of these hops are shown in Table 2.

The− -ácidos en lúpuloSufren isomeribajo ciertas condiciones, formando ácidos isosórbcon una amargura extremadamente fuerte. Este compuesto es el principal componente responsable del amargor de la cerveza; Sin embargo, debido a su inestabilidad, particularmente bajo la exposición a la luz, se descompone, los fragmentos resultantes reaccioncon compuestos que contienen azufre en la cerveza para formar 3-metil-2-butenil mercaptano, que es la sustancia principal responsable del deterioro del sabor de la cerveza, comúnmente conocido como "inducido por la luz fuera de sabor" [13]. El proceso de reacción se ilustra en la figura 1.

The reason for the decomposition of iso-α-acids is due to the presence of three unsaturated bonds in their side chains. To further improve the light stability of beer and enhance its quality, a series of chemically modified α-acid derivatives with better light stability have been applied in beer brewing [14-15]. These compounds include dihydro, tetrahydro, and hexahydro isohydroxy-α-acids, among which dihydro isohydroxy-α-acid has the best solubility, featuring a mild bitterness and stability, but its photostability is slightly poorer, and its bitterness is only 0. 7 times that of is α-acid. Tetrahydro is α-acid has slightly poorer solubility but exhibits extremely strong and persistent bitterness, with a slight astringency, and its bitterness is 1.6 times that of is α-acid. Additionally, it has excellent photostability and aids in forming fine, stable foam in beer, though it occasionally imparts a lingering bitterness. Hexahydroiso-α-acid has the lowest solubility compared to the above two products but the best photostability. Its bitterness is mild and stable, and it also helps foam stability, though it is relatively expensive. During the isomerization process of α-acid, due to the presence of cis-trans isomers, its isomers and hydrogenated derivatives are composed of a larger group of substances. Figure 2 provides a simple schematic diagram of the structural conversion process of α-acid and its derivatives.

β-acid is another important component of hop soft resin. which is almost insoluble in cold water and beer. However, the oxidation product of β-acid, humulone, has a very strong bitterness, which is twice that of iso-α-acid, and it also has a relatively high solubility in water. This compound typically plays a good supplementary and balancing role in compensating for the decrease in bitterness caused by the loss of α-acid and the oxidative degradation of iso-α-acid in beer. Similar to α-acids, β-acids are a class of compounds composed of five main isomers: humulone, cohumulone, adhumulone, trans-humulone, and trans-cohumulone. Typically, the first three compounds account for 95% of the total content [16], but their content and composition ratios are not important indicators of hop quality or variety. β-acids generally do not undergo isomerization, except for their own tendency to oxidize. Under certain conditions, β-acids can undergo hydrogenation reactions to form more stable and active hexahydro-β-acids. The chemical structures and transformation processes of β-acids and their oxidative and hydrogenated derivatives are shown in Figure 3.

The Componentes de aceite esencial en los extractos de lú.Son principalmente terpenos y sesquiterpen, como el humuleno, carvone, limoneno, farneseno, pineno, tujeno y junipereno, que representan más del 75% del contenido total de aceites esenciales. Otros componentes incluyen algunos compuestos que contienen oxígeno y compuestos que contienen azufre, que no sólo son cruciales para el sabor de la cerveza, sino también los componentes principales responsables de los efectos calmantes y sedantes del lúpulo [17-18]. En la figura 4 se muestran las fórmulas estructurales de algunos componentes de aceite esencial en el lúpulo.

The cones of hops also contain polyphenolic active components such as tannins, flavonoids, and flavonoid glycosides. The polyphenolic compounds in hops are classified into four categories: phenolic acid compounds, flavonoids, catechins, and proanthocyanidins. The most abundant are catechins, including small amounts of epicatechin, gallocatechin, and epigallocatechin. The proanthocyanidins in hops polyphenols are primarily proanthocyanidins formed by the condensation of two or more flavan-3-ols, along with some anthocyanins, cyanidins, and delphinidins [19]. These compounds exist either in free form or as glycosides. Among these substances, known active compounds include cyanidin, asparagine, tannins and resins, luteolin glucoside, grandiflorin, oleanolic acid, isohydroxycinnamic acid, and 8-isopentenylnaringenin, among others.

Polifenoles de lúpuloSon de gran importancia para la calidad de la cerveza, jugando un papel en la mejora y mejora de la estabilidad biológica y la estabilidad del sabor de la cerveza durante el proceso de elaboración [20-21]. Durante la producción de cerveza, la quercetina sufre más reacciones, con productos de reacción incluyendo isoquercetina y deshidrocicloquercetina. La humulona y la isohumulona en los lúpulo pueden inhibir el crecimiento de ciertas células cancerosas humanas sin afectar el crecimiento de células no cancerosas en los animales. También pueden tener efectos similares sobre la hormona sexual femenina estrógeno en los mamíferos, y la investigación de sus actividades funcionales es un foco actual en el estudio de las propiedades farmacológicas del lúpulo. Los principales compuestos polifenóen lúpulo están estructuralmente representados en la figura 5.

2 efectos farmacológicos

Like its history in beer brewing, the medicinal use of hops is also very ancient. In 13th-century Europe, hops, along with other herbs such as rosemary, valerian, coriander, and marshmallow, began to be used as medicinal herbs. The Compendium of Materia Medica records [22] that hops are bitter and slightly cool in nature, with functions including stomachic, sedative, expectorant, and anti-tuberculosis properties. The Book of Food Herbs and Remedies records [23] that hops have inhibitory effects on various bacteria and exhibit sedative and estrogen-like activities. In folk medicine, hops are commonly used to make tea, with functions including stomach-strengthening, vision-improving, thirst-quenching, blood pressure-lowering, cough-relieving, diuretic, and sedative effects. The medicinal part is the green inflorescence, which has been processed into hop extract tablets, hop extract emulsion, and hop extract extract tablets for use.

2.1 efectos antimicrobianos y antiinflamatorios

Modern pharmacological analysis shows that the chemical components in hop extracts, such as humulone and lupulone, have inhibitory effects on Mycobacterium tuberculosis, Staphylococcus aureus, and Bacillus subtilis, among others. Among these, humulone is more potent than lupulone [24-26]. This is because humulone has strong lipophilicity, a high distribution coefficient, and easily penetrates the wax membrane of Mycobacterium tuberculosis, exerting a special affinity and inhibiting its growth. A study using agar overlay technology on 11 varieties of hops and one wild hop species showed that both hops essential oil and solvent extracts exhibit strong inhibitory effects against Gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus), acid-fast bacteria, and fungi (dermatophytes), but showed little activity against Gram-negative bacteria (Escherichia coli) and yeast [27]. Polyphenolic compounds in hops can inhibit the growth of streptococci and delay the onset of dental caries. Tagashira et Al.[28] found that the minimum inhibitory concentration of hop polyphenol extracts for inhibiting the growth of dental caries streptococci was significantly lower than that of extracts from oolong tea or green tea.

Other studies have shown that under weakly acidic conditions (pH = 4–7), the antibacterial effect of hops increases with increasing acidity. When considering the degree of ionization, trans-isohumulone exhibits antibacterial activity 20 times higher than humulone, 11 times higher than humulone, and 9 times higher than trans-humulone acid [29]. Additionally, patent reports indicate that α-acid, β-acid, isosorbide, or polyphenolic compounds in hops can be used as new selective cyclooxygenase-2 (COX-2) inhibitors, reducing inflammation and significantly lowering the incidence of adverse cardiovascular events and gastric side effects [30]. Furthermore, traditional Chinese medicine uses hops, plantain, and Chine (15g cada uno) decocted en agua para tratar la inflamación del tracto urin, cistitis, nefritis, edema, y dificultad que orina. Experimentos In vitro con decocción de lúpulo silvestre mostraron efectos inhibitcontra Staphylococcus aureus, difteria Bacillus, Shigella, estreptohemolítico del grupo B, Escherichia coli, Bacillus anthracis y Salmonella typhi [31]. Los efectos analgésicos y analgésicos de los lúpulo se atribuyen principalmente a las propiedades antibacterianas de los − -ácidos y − -ácidos, que pueden aliviar los síntomas inflamatorios y reducir o eliminar el dolor.

2.2 efectos antitumorales

Una serie de experimentos con animales han demostrado que el lúpulo puede prevenir el cáncer y proporcionar una protección significativa contra la oxidplasmática. elCompuestos flavonoidesQue contienen grupos isoprenilo en el extracto de lú, en particular quercetina e isoquercetina, exhiactividad fisiológica significativa in vitro, exhibiefectos antiproliferativos y citotóxicos en células de cáncer de mama (MCF-7), células de cáncer de colon (HT-9) y células de cáncer de ovari(A-2780). El efecto inhibites dependiente de la concentración en concentraciones que van de 0.1 a 100 μmol/L, con el mecanismo de acción que implica la inhibición de la síntesis de ADN [32]. Huangfuquan también inhila la actividad de la enzima procarcinogénica citocromo P-450, evitando su activación de carcinógenos [33], e induce la actividad de enzimas que desintoxica carciny antraquinona reductasa [34].

In vitro experiments have shown that humulone in hop extracts inhibits the proliferation and invasion of breast cancer cells. When B-chronic lymphocytic leukemia cells from patients were cultured in vitro, humulone exhibited antitumor activity in B-chronic lymphocytic leukemia cells in vitro experiments. The mechanism of action is through a cell apoptosis mechanism [35]. Humulone in hops has a significant inhibitory effect on inflammation induced by tumor cells treated with phorbol (12-O-tetradecanoylphorbol-13-acetate, TPA), and can also inhibit inflammation caused by arachidonic acid-induced ear edema in mice [36]. Humulone and caryophyllene have significant inhibitory effects on various tumor cells (e.g., leukemia cells); hydroxyflavonoids can inhibit the synthesis of a protein that promotes the development of human colorectal cancer, and inhibit the spread of gastric cancer cells, and the spread of squamous cells in throat and brain cancer [37-39]. The combination of lonicerin and vitamin D3is more effective than vitamin D3 alone in treating leukemia. This combination holds great promise for the development of natural drugs against leukemia [40].

2.3 efectos antioxidantes

Studies have shown that polyphenolic compounds in hops exhibit significant antioxidant effects [41-43]. Hops polyphenols can inhibit the activity of lipoxygenase (LOX), whose function is associated with its accessory enzymes and plays a central role in reactive oxygen species (ROS) activity. Certain dihydroflavonol derivatives, such as catechin and procyanidin B3, can bind to the polar groups of enzymes, thereby protecting “oxidatively sensitive substances” like lipids from rapid enzymatic oxidation. Additionally, polyphenolic compounds can act as chelating agents, blocking the transfer reactions of heavy metal ions (such as copper and iron), thereby eliminating their catalytic effects and preventing the generation of excessive oxygen free radicals. Furthermore, the “free radical theory” underlying the formation of beer aging flavors suggests that polyphenols in hops can capture free radicals from inorganic and organic compounds, weakening their reactions. The outcomes of these reactions directly influence the formation of aging flavor compounds. Coniferic acid has lipid-oxidizing inhibitory effects in the body and inhibits enzymes involved in the conversion of glycerol diester to glycerol triester.

2.4 Función reductora del azúcar en la sangre

La investigación ha encontrado que algunos componentes en lúpulo tienen efectos que bajan azúcar en la sangre y pueden inhibir el inicio de la diabetes [44]. Keiji's research results confirm that the isohumulone in hops can prevent obesity and the onset of type II diabetes, improve lipid metabolism, and inhibit the occurrence of atherosclerosis [45]. Peroxisome proliferator-activated receptors (PPARs) are a class of ligand-activated transcription factors involved in regulating various physiological responses, such as lipid metabolism, glucose homeostasis, cell differentiation, and apoptosis. There are three types of PPARs: PPAR-α, PPAR-β/δ, PPAR-γ are all expressed in endothelial cells.

The isohumulone in hop extract has the ability to activate PPAR-— yPPAR-γ. In diabetic KK-Ay mice, after administration of isohumulone, the levels of glucose, triglycerides, and free fatty acids in plasma were significantly reduced, but no significant increase in body weight was observed. After feeding C57BL/6N mice a high-fat diet and then administering isopentenylic acid, it was found that their glucose tolerance improved and insulin resistance decreased. The size of fatty livers in these animals decreased, and the number of apoptotic adipocytes increased. The results of a randomized controlled trial investigating the effects of isosorbide on diabetes showed that after administering isosorbide to mice with insulin antibodies and type 2 diabetes for 8 weeks, isosorbide significantly reduced blood glucose levels and hemoglobin A1c levels, and improved insulin sensitivity in mice fed a high-fat diet [46]. Other studies have reported that hop extracts, particularly the isohumulone component, exhibit very strong aldose reductase inhibitory activity, with inhibition rates comparable to those of the potent aldose reductase inhibitor quercetin [47].

2.5 promover la digestión

La medicina moderna sugiere [48] esoLos extractos de lútienen efectos relajantesSobre los músculos lisos y contribuyen a la digestión. Por lo tanto, el lúpulo se usa a menudo en combinación con otros medicamentos para tratar la disfunción gastrointestinal, la ileítis segmenty la incomodidad gástrica. De acuerdo con reportes clínicos, el lúpulo tiene un excelente efecto de fortalecimiento estomacal, digestivo y diur, y puede usarse para tratar la pérdida de apetito, distenabdominal, edema y cistitis. También demuestran una significativa eficacia terapéutica en el alivio de las infecciones de los órganos digestivos y el tratamiento de las úlceras gástriy duoden[49-50]. El efecto diurdel lúse debe principalmente a la presencia de espárragina en el lúlúpulo. Además, hay informes sobre el uso del lúpulo como medicamento veterinario. Estudios realizados por Sudley et al. [51] indican que los lúpulos tienen buenos efectos terapéuticos sobre la atononía ruminal, la impactación ruminal, la hinchazón ruminal en el ganado y las enfermedades gastrointestinales en caballos y mulas.

2.6 efectos antivirales

Studies on the effects of compounds in hops on DNA and RNA viruses have shown [52-53] that the isohumulone in hops has certain antiviral effects against bovine filterable diarrhea virus and cytomegalovirus, while humulone and isohumulone have antiviral effects against cytomegalovirus, herpes simplex virus HSV-1, and HSV-2. with xanthohumol exhibiting significantly stronger activity than isohumulone. Xanthohumol also has antiviral effects against bovine filterable dysentery viruses. Fro..lich et al. [54] found that the isoprenylated flavonoids in hops exhibit antimalarial activity, with xanthohumol demonstrating stronger efficacy.

2.7 efectos sedantes, ansiolíticos y estimulantes del sueño

Los lúpulo tienen efectos sedantes, hipnóticos y antiespasmódicos, y han sido ampliamente utilizados desde la época romana [55-58]. Tradicionalmente, el lúpulo se ha utilizado para tratar el insom, la tensión nerviy la neuralgia con excelente eficacia. Estudios experimentales han demostrado que el lúpulo puede aumentar la duración del sueño reducido por pentobarbital. Otros estudios han demostrado que la combinación de lúpulo con laRaíces de la valerianaY la pasiflora puede mejorar la calidad del sueño y prevenir los trastornos del sueño. Cuando se usa como sedante, el lúpulo se combina típicamente con una o más hierbas. Cuando se administraron altas dosis de lúpulo a animales de experimentación, se encontró que el 2-metil-3-buten-2-ol en lúpulo posee actividad sedante del sistema nervioso central. Aunque la cantidad de este compuesto en los lúpulo es relativamente pequeña, puede ser sintetizen el cuerpo a través del metabolismo de los ácidos amargos y humulona en los lúpulo, lo que explica el efecto sedante de los lúpulo.

2.8  Efectos similares al estrógeno

Research indicates that, in addition to the aforementioned effects, hops possess numerous other benefits [59-64]. Hops contain substances with progesterone-like activity and gonadotropin-inhibiting activity, some of which have emmenagogue effects. 8-Isopentenylflavone, a highly promising progesterone-like substance, can reduce hot flashes during menstruation in women. Additionally, hop preparations have significant efficacy in treating leprosy. Hops are also used to treat coughs, and topically applied to alleviate skin itching and measles, among other conditions. They are also suitable for treating various infections. Furthermore, studies have shown that lupeol in hop extracts has a preventive effect against osteoporosis, and that feeding rodents a diet containing isomerized hop extract with isoharpyranone can prevent diet-induced obesity.

3  Las perspectivas

Due to the unique and irreplaceable role of hops in beer brewing, researchers will continue to focus on its brewing characteristics, including the separation, chemical modification, and modification of its main components to synthesize, separate, identify, and apply derivative products with superior brewing quality. In recent years, with the deepening of research on the bioactive components of plant extracts worldwide, the various biological and pharmacological activities of hop extracts have gradually been elucidated. As one of the traditional Chinese medicinal ingredients, the application of hops in traditional Chinese medicine has a history of over a thousand years, but it has been largely limited to clinical use and reports on its definite therapeutic effects, with the active components, their mechanisms of action, and their relationships not yet fully understood.

Los estudios químicos y farmacológicos modernos han revelado que, además de los compuestos activos bien estudiados como la humulona y la lupulona, los polifenoles y flavonoen los extractos de lúhan llamado cada vez más la atención. En términos de aplicación, los países extranjeros ya han ampliado su uso más allá de la industria de la cerveza en la alimentación, la producción de alcohol, la fabricación de azúcar y la industria farmacéutica. En los últimos años, los investigadores nacionales también han comenzado a participar en estudios relacionados. Se cree que con el continuo fortalecimiento de la investigación sobre sus componentes activos y constituyentes efectivos, como aPrincipio activo natural derivado de plantasCon fuertes propiedades antibacterianas y antiinflamatorias, el lúpulo, esta medicina tradicional China, jugará un papel cada vez más importante.

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