맥주에 홉 추출물의 용도는 무엇입니까?

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 cultivati에areas 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 홉 추출 물 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.

⑵ 추출물의 활성성분 1

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. 이 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. 이ratio 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.

Theα-acids 홉에특정 조건 하에서 이성질화를 거쳐 극히 강한 쓴맛을 가진 이소르브산을 형성한다.이 화합물은 맥주의 쓴맛을 일으키는 주된 성분이다;그러나 불안정성, 특히 빛에 노출되면 분해되기 때문에, 그 결과 생긴 파편이 맥주의 유황 함유 화합물과 반응하여 3-메틸-2-부테닐 메르캅탄을 형성하는데, 이것이 흔히"light-induced off-flavor"[13] 라고 불리는 맥주 맛 퇴화의 주된 물질이다.반응 과정을도 1에 나타내었다.

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 ⑵ 추출물에 들어있는 에센셜 오일 성분휴무렌, 카본, 리모넨, 파르네센, 피넨, 투젠, 쥬니페렌 등의 테르펜과 세스키테르펜이 주로 함유되며, 전체 에센셜 오일 함량의 75% 이상을 차지한다.그 외 성분으로는 산소 함유 화합물과 유황 함유 화합물이 일부 포함되어 있는데, 이들은 맥주의 풍미를 내는데 결정적인 역할을 할 뿐만 아니라 홉의 진정 및 진정 효과를 일으키는 주된 성분이기도하다 [17~18].홉 내 일부 에센셜 오일 성분의 구조식은 그림 4에 표시되어 있다.

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.

폴리 페놀 홉맥주 품질에 매우 중요한데, 양조 과정 중 맥주의 생물학적 안정성과 향미 안정성을 향상시키고 향상시키는 역할을 한다 [20-21].맥주 생산 중에, 케르세틴은 추가 반응을 거치게 되는데, 이소케르세틴과 디하이드로사이클로케르세틴을 포함한 반응 생성물이 있다.홉에 들어있는 Humulone과 isohumulone은 동물의 비암성 세포의 성장에 영향을 주지 않으면서 특정 인체 암세포의 성장을 억제할 수 있다.또한 이들은 포유류의 여성 성호르몬인 에스트로겐에도 유사한 영향을 미칠 수 있으며, 이들의 기능적 활동에 대한 연구는 호프의 약리학적 특성에 대한 연구에서 현재 주목받고 있다.홉의 주요 폴리페놀성 화합물은 구조적으로 그림 5에 표시되어 있다.

2 약리학적 효과

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 항균 및 항염증 효과

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 알다.[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 친 (각 15g)을 물에 데쳐 요로염증, 방광염, 신장염, 부종, 배뇨곤란 등을 치료한다.야생홉을 이용한 In vitro 실험에서 황색포도상구균, diphtheria bacillus, Shigella, group B 용혈성연쇄상구균, Escherichia coli, bacillus anthracis, Salmonella typhi [31]에 대한 억제 효과가 나타났다.홉의 통증과 진통제 효과은 주로 항균 α의 특성에 기인-acids와 β-acids, 염증을 완화시 킬 수 있는 증상과 고통을 줄이 거나 없애다.

2.2 항암 효과

일련의 동물실험에 의하면 홉은 암을 예방하고 혈장산화에 대해 상당한 보호작용을 한다.이는 화합물홉 추출물에 isoprenyl group을 함유하고 있으며, 특히 quercetin과 isoquercetin은 in vitro에서 유의한 생리활성을 나타내어 유방암세포 (MCF-7), 대장암세포 (HT-9), 난소암세포 (A-2780)에 대한 증식억제 및 세포독성 효과를 나타내었다.억제 효과는 concentration-dependent 농도에서 0. 1에서 100 μ mol/L에 이르기까지, 억제와 관련 된 행동의 메커니즘의 DNA 합성 [32]다.또한 황푸펀은 발암 유발 효소인 시토크롬 P-450의 활성을 억제하여 발암 물질의 활성을 막고 [33], 발암 물질을 해독하는 효소와 탄저퀴논 환원효소의 활성을 유도한다 [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 항산화 효과

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 혈당을 낮추는 기능

연구에 따르면 홉의 일부 성분은 혈중 당도를 낮추는 효과가 있으며 [44] 당뇨병 발병을 억제할 수 있는 것으로 밝혀졌다.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-α와PPAR-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 소화 촉진

현대의학으로 보면 [48] 그렇게 볼 수 있다⑵ 추출물은 긴장을 풀어주는 효과가 있다근육을 부드럽게하고 소화를 촉진합니다.따라서 호프는 위장기능장애, 분절성 회장염, 위 불편감 등을 치료하기 위해 다른 약물과 함께 사용하는 경우가 많다.임상 보고에 따르면 홉은 위장 강화, 소화, 이뇨 작용이 뛰어나며 식욕 부진, 복부 팽만, 부종, 방광염 등의 치료에 효과가 있다.그들은 또한 소화 기관의 감염을 완화하고 위 및 십이지장 궤양을 치료하는 데 상당한 치료 효과를 입증한다 [49-50].홉의 이뇨 효과는 주로 홉에 있는 아스파라긴의 존재 때문이다.게다가, 수의학으로 홉이 사용되었다는 보고가 있다.Sudley 등의 연구 [51]에 따르면 홉은 반추위 atony, 반추위 impaction, 소의 반추위 bloen, 말과 노새의 위장 질환에 좋은 치료 효과가 있다고 한다.

2.6 항바이러스 효과

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.

진정제, 불안, 수면 촉진 효과 2.7

홉은 진정, 최면, 항경련 효과가 있으며, 고대 로마 시대부터 널리 사용되었다 [55~58].전통적으로 홉은 뛰어난 효능으로 불면증, 신경긴장, 신경통 치료에 사용되어 왔다.실험 연구에 따르면 호프가 펜토바빌로 줄어든 수면 시간을 늘릴 수 있는 것으로 나타났다.다른 연구들은 홉과을 결합하는 것을 보여주었다발레리안의 뿌리 (roots of Valerian)그리고 passionflower는 수면의 질을 향상시키고 수면 장애를 예방할 수 있습니다.진정제로 사용될 때, 홉은 일반적으로 하나 이상의 다른 허브와 결합된다.실험동물에게 고용량의 홉을 투여하였을 때, 홉에 함유된 2-methyl-3-buten-2-ol은 중추신경계 진정활성을 보유하고 있는 것으로 나타났다.홉에 함유된이 화합물의 량은 비교적 적지만 쓴맛 나는 산과 홉에 함유된 후물론의 대사를 통해 체내에서 합성될수 있는데 이는 홉의 진정효과를 설명한다.

2. 8  겐 효과

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  전망

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.

현대의 화학 및 약리학적 연구에 따르면, 잘 연구된 휴물론, 루풀론 등의 활성 화합물 외에도 홉 추출물의 폴리페놀과 플라보노이드 성분이 많은 관심을 모으고 있다.적용의 측면에서 외국에서는 이미 맥주산업을 넘어 식품, 주류 생산, 설탕 제조, 제약 산업 등으로 그 용도가 확대되고 있다.최근 들어 국내 연구자들도 관련 연구에 몰두하기 시작했다.그 활성성분과 유효구성요소에 대한 연구가 지속적으로 강화되면서, a 로서천연 식물 유래 활성 성분강한 항균 및 항염증 특성을 가진이 한약인 홉은 점점 더 중요한 역할을 할 것입니다.

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[51] 수델리.수의임상 실무에서 홉의 응용 [J].지린축산수의학, 1994, 16(6):31-32.

[52]BUCKWOLD V E, WILSON R J, NALCA A 등.⑵ 구성물질의 일련의 ofDNA 및 RNA 바이러스에 대한 항바이러스 활성 [J.항바이러스연구, 2004, 61(1):57-62.

[53] 시무라 M, 하스미 A, 미나토 T 외.Isohumulones는 ppar-α [J]의 활성화를 통해 혈중 지질 상태를 조절한다.Biochimica et Biophysica Acta, 2005, 1736(1):51-60.

[54] FRO. LICH S, SCHUBERT C, BIENZLEU, 외.호프 (Humulus lupulus)의 prenylated chalcone 유도체의 In vitro antiplasmodial activity와 혜민과의 상호작용 (J.J 항균화학요법, 2005, 55(6):883-887.

[55]BARNES J. 허브치료학 (5):불면증 (J.대한약학회지, 2002, 269:219-221.

[56] 뉴올 CA, 앤더슨 LA, 필립슨 JD.한방약재:보건의료전문가를 위한 안내서 [M.런던:제약 신문, 1996:162-163.

[57]WOHLFART R, WURM G, HANSEL R. 홉에서 sedative-hyp-notic 활성 성분 검출.5. 쓴 산을 sedative-hypnotic activity [J]를 갖는 홉 성분인 2-methyl-3-buten-2-ol로 분해.Arch Pharm, 1983, 316(2):132-137.

[58]HANSEL R, WOHLFART R, COPER H. Sedative-hypnotic com-having oestrogenic and antiproliferation ative bioactivity:EP, 1543834[P].2005-06-22다.

[51] 수델리.수의임상 실무에서 홉의 응용 [J].지린축산수의학, 1994, 16(6):31-32.

[52]BUCKWOLD V E, WILSON R J, NALCA A 등.⑵ 구성물질의 일련의 ofDNA 및 RNA 바이러스에 대한 항바이러스 활성 [J.항바이러스연구, 2004, 61(1):57-62.

[53] 시무라 M, 하스미 A, 미나토 T 외.Isohumulones는 ppar-α [J]의 활성화를 통해 혈중 지질 상태를 조절한다.Biochimica et Biophysica Acta, 2005, 1736(1):51-60.

[54] FRO. LICH S, SCHUBERT C, BIENZLEU, 외.호프 (Humulus lupulus)의 prenylated chalcone 유도체의 In vitro antiplasmodial activity와 혜민과의 상호작용 (J.J 항균화학요법, 2005, 55(6):883-887.

[55]BARNES J. 허브치료학 (5):불면증 (J.대한약학회지, 2002, 269:219-221.

[56] 뉴올 CA, 앤더슨 LA, 필립슨 JD.한방약재:보건의료전문가를 위한 안내서 [M.런던:제약 신문, 1996:162-163.

[57]WOHLFART R, WURM G, HANSEL R. 홉에서 sedative-hyp-notic 활성 성분 검출.5. 쓴 산을 sedative-hypnotic activity [J]를 갖는 홉 성분인 2-methyl-3-buten-2-ol로 분해.Arch Pharm, 1983, 316(2):132-137.

[58]HANSEL R, WOHLFART R, COPER H. Sedative-hypnotic com