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18β-Glycyrrhetinic acid, CAS 471-53-4, Molecular formula C30H46O4, white crystalline powder, insoluble in water, soluble in ethanol, chloroform, pyridine, and acetic acid. It is a common food for both medicine and food. Liquorice extract is widely used in candy and canned food as a natural sweetener. The sweet taste of licorice comes from glycyrrhizic acid and glycyrrhetinic acid. The former is a kind of triterpenoid saponin, accounting for about 4%~5% of the dry weight of glycyrrhizic root, and its sweetness is 50 times of sucrose.
Glycyrrhetinic acid is formed by the hydrolysis of glycyrrhizic acid to remove the sugar acid chain, and its sweetness is 250 times of sucrose. Glycyrrhetinic acid has cytotoxicity. Long-term consumption of glycyrrhizic acid (100g/d) in large quantities can lead to severe hypertension and cardiac hypertrophy. The clinical symptoms are sodium ion retention and potassium ion excretion. In severe cases, it can lead to extreme weakness and ventricular fibrillation.
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Chemical Formula |
C30H45O4 |
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Exact Mass |
469 |
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Molecular Weight |
470 |
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m/z |
469 (100.0%), 470 (32.4%), 471 (2.7%), 471 (2.4%) |
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Elemental Analysis |
C, 76.72; H, 9.66; O, 13.63 |
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18β-Glycyrrhetinic acid, as the core active ingredient in plants of the licorice genus (such as light fruit licorice and swollen fruit licorice), has a molecular structure of oleanane type pentacyclic triterpenoids, which possess both corticosteroid like activity and natural sweetness characteristics. Since its separation and identification in the early 20th century, its application has expanded from traditional Chinese medicine to modern medicine, food, cosmetics, and daily chemical fields, forming an interdisciplinary application system.
Medical field: Breakthrough from basic treatment to precision medicine
Anti inflammatory and immune regulation:
Multi-target inhibition of inflammatory cascade reactions.By inhibiting the synthesis and release of inflammatory mediators such as prostaglandin E2, histamine, and serotonin, blocking the NF - κ B signaling pathway, capillary permeability is significantly reduced. Clinical studies have shown that its anti-inflammatory potency is about 1/10 of that of hydrocortisone, but there is no risk of pituitary adrenal system inhibition.
Organ protection:
In the liver ischemia/reperfusion injury model, pretreatment can reduce liver cell apoptosis rate by 32% and neutrophil infiltration by 45%.
Antiviral and anti-tumor: dual mechanism blocks disease progression
Antiviral effect: By inhibiting the synthesis of viral envelope proteins, it blocks the hepatitis virus HIV, The replication cycle of influenza virus. For example, its EC50 value for HBV is 2.3 μ M, and its combination with lamivudine can enhance antiviral efficacy.
Antitumor mechanism:
Direct effect: Inducing tumor cell apoptosis (such as through ROS mediated mitochondrial pathway) and inhibiting gastric cancer cell proliferation (IC50=8.2 μ M).
Indirect effects: downregulate VEGF expression and inhibit tumor angiogenesis; Enhance NK cell activity and improve immune surveillance function.
Structural optimization: Derivatives with C-11 carbonyl group reduced to hydroxyl group retain anti-tumor activity while reducing cytotoxicity by 60%.
Treatment of special diseases:
filling clinical gaps
Alternative therapy for Addison's disease: As a substitute for deoxycorticosterone, it maintains electrolyte balance, but needs to be combined with hydrocortisone to avoid crisis.
Cholestasis induced liver disease: upregulate FXR expression, promote bile acid excretion, and reduce serum bilirubin levels by 35%.
Neuroprotection: In Parkinson's disease models, inhibition of MPTP induced neuronal apoptosis improves motor dysfunction.
Food Industry: Innovative Application of Natural Functional Ingredients
High potency sweeteners: a healthy alternative to sucrose
18β-Glycyrrhetinic acid has a sweetness 50 times that of sucrose, and its calorific value is only 1/10 of it. In sugar free foods, its combination with erythritol can mask the bitterness and enhance the taste acceptance. For example, a certain brand of sugar free beverage increased the sweetness persistence by 40% by adding 0.02% glycyrrhetinic acid.
Functional food additives: multidimensional health benefits
Antioxidant enhancement: Adding 0.1% glycyrrhetinic acid to plant-based meat products can extend shelf life by 25%, with a DPPH free radical scavenging rate of 89%.
Intestinal health promotion: By regulating the gut microbiota (such as increasing the abundance of bifidobacteria), constipation symptoms can be improved, and clinical trials have shown a 30% increase in bowel frequency.
Sports nutrition supplement: Combined with branched chain amino acids, it can reduce the level of muscle injury markers (CK) after exercise by 22% and accelerate recovery.
Cosmetics field: the benchmark for active ingredients in scientific skincare
Whitening and spot lightening
Multi pathway inhibition of melanin production
Tyrosinase inhibition: The IC50 value of glycyrrhetinic acid derivative glycyrrhetinic acid is 0.8 μ M, which is 16 times that of arbutin.
Melanin transport blockade: Downregulation of RAB27A protein expression reduces the transfer of melanosomes to keratinocytes.
Clinical verification: After 8 weeks of continuous use of essence containing 1.5% licorice extract, the MASI score of patients with chloasma decreased by 39.2%, and there was no hydroquinone irritation.
Chronic barrier injury
promotes ceramide synthesis, reduces transcutaneous water loss (TEWL) by 28%, and increases repair speed by 2.3 times.
Microbial regulation: Inhibits the formation of biofilm in Propionibacterium acnes and reduces the risk of drug resistance when combined with salicylic acid.
3. Anti aging: Dual effect synergy of antioxidant and collagen regeneration
Free radical scavenging: The ORAC value of licorice chalcone A is 5200 μ mol TE/g, which is 1.8 times that of vitamin C.
Daily chemical products: functional extension of natural ingredients
Oral care: dual protection of antibacterial and anti-inflammatory effects
Dental plaque control
Glycyrrhetinic acid has an inhibition zone diameter of 18mm against Streptococcus mutans, and when combined with sodium fluoride, it can reduce the incidence of dental caries by 37%.Gum Health: Adding 0.5% glycyrrhetinic acid to toothpaste can reduce gingival bleeding index by 41%, and its mechanism is related to inhibiting IL-6 release.Personal cleaning: gentle stain removal and skin protection
Shampoo formula: By regulating scalp sebum secretion, the oil production of oily hair is reduced by 31%, and there is no dry and tight feeling.
Application of shower gel
When combined with oat pectin, it can reduce the irritation of surfactants and shorten the duration of skin erythema by 50%.
Glycyrrhetinic acid, with its unique molecular structure and multi-target mechanism of action, has become a bridge connecting traditional wisdom and modern technology. With the advancement of structural biology and delivery technology, its application boundaries will continue to expand, providing safer and more efficient solutions for human health.
A preparation method of 18β-glycyrrhetinic acid
Take 140g of glycyrrhizic acid powder (glycyrrhizic acid content is about 25% HPLC), add 1120ml of 95% edible ethanol, extract at 40 ℃ for 3 hours, filter to remove insoluble impurities, distill the filtrate and recover ethanol to obtain the extract, dry the extract at 100 ℃ on a water bath to obtain 118g of dry extract with a moisture content of not more than 20%.
After crushing the dry extract, take 100g, add 300ml of 70% glacial acetic acid, add 7ml of concentrated sulfuric acid, hydrolyze and acetylate under normal pressure, raise the temperature to 98~103 ℃, and react for 2 hours. After the hydrolysis and acetylation are completed, cool to room temperature, filter the separated solids, wash the filter cake with 250ml of 65% acetic acid, and then wash with 200ml of ethanol, finally wash with 300ml of water, and dry at 100 ℃ to obtain 20.21g of crude acetylglycyrrhetinic acid, with a purity of 88.2% (HPLC).
Take 20g of acetylglycyrrhetinic acid, add 300ml of water, add 5g of sodium hydroxide to adjust the pH to 13, reflux hydrolysis at atmospheric pressure for 4 hours, reduce to room temperature, acidize the pH to 5.2 with hydrochloric acid, filter, wash the filter cake with pure water, remove the inorganic salt, and dry at 100 ℃ to obtain 17.8g of crude glycyrrhetinic acid, purity 92.9% (HPLC).
And then dissolve the crude glycyrrhetinic acid with 214ml of 95% ethanol by volume percentage concentration, 25% (4.45g) of the weight of the crude glycyrrhetinic acid is added with activated carbon for reflux decolorization. After reflux decolorization, the filtrate is filtered. After ethanol is recovered, the solid is separated out, and 16.4g of glycyrrhetinic acid is filtered, with a purity of 98.2% (neutralization method).
To further purify, use 95% ethanol to recrystallize three times to obtain glycyrrhetinic acid product with purity of 98% (HPLC). The total impurity peak is not more than 2%, and the single impurity peak is not more than 0.7%, which fully conforms to the European Pharmacopoeia standard.
adrenocortical hormone-like effect
Mineralocorticoid effect:
For healthy people and many animals, glycyrrhetinic acid can promote the increase of sodium, water retention, and potassium excretion, showing a deoxycorticosterone like effect. When patients with bilateral adrenals are treated with 40mg of hydrocortisone intramuscularly for maintenance therapy every day, if 4g of glycyrrhetinic acid is injected subcutaneously every day, synergy will occur and electrolyte will be kept in balance.
Glucocorticoid effect:
The chemical structure of 18β-glycyrrhetinic acid is similar to that of corticosteroids. Glycyrrhetinic acid can still produce sodium retention, antidiuretic and anti-inflammatory effects in animals with adrenocorticectomy and hypophysiectomy. The effect of 25 mg glycyrrhetinic acid on water and sodium retention in rats was stronger than that of 1 mg deoxycorticosterone. Therefore, the deoxycorticosterone-like effect of glycyrrhetinic acid is not produced by endogenous deoxycorticosterone and aldosterone, but may be a direct effect.
Anti-inflammatory and anti-immune effects
Glycyrrhetinic acid has an anti-inflammatory effect similar to that of cortisone or cortisone. Glycyrrhetinic acid has inhibitory effects on cotton ball granuloma, formalin-induced foot swelling and subcutaneous granulomatous inflammation in rats, and its anti-inflammatory potency is about 1/10 of that of cortisone or hydrocortisone. Glycyrrhetinic acid has inhibitory effect on experimental arthritis induced by carrageenan in rats, and has different degrees of inhibitory effect on allergic reaction induced by horse serum or egg white in guinea pigs. Its anti-inflammatory and anti-allergic reactions may be related to inhibition of capillary permeability.
Anti-histamine or reduction of cell responsiveness to stimulation.Glycyrrhetinic acid has inhibitory effects on various acute inflammation. Its anti-inflammatory effect is not dependent on the pituitary-adrenocortical system, but is related to the inhibition of PgE2 production in inflammatory tissues, the antagonism of inflammatory mediators histamine, 5-hydroxytryptamine, etc. Sodium glycyrrhetinic acid can inhibit the formation of malondialdehyde, the degradation product of Pg endoperoxide in the inflammatory foot of mice induced by protein, which can be antagonized by exogenous arachidonic acid.
Sodium glycyrrhetinic acid can also enhance the non-specific cellular immune function of the body. 18- β Glycyrrhetinic acid has immunomodulatory effect on acute serum disease in rabbits.Fifty rabbits were randomly divided into experimental group and control group. The rabbit model of transient acute serum disease was established with bovine serum protein (BSA) as antigen. Will 18- β Glycyrrhetinic acid was dissolved in olive oil (150mg/ml). The animals in the experimental group took 18- β Glycyrrhetinic acid 200mg/kg was injected intramuscularly into animals. The control group was intramuscularly injected with olive oil.
Results The anti-BSA-1gg antibody in the serum of animals in the control group and the experimental group was detected on the 6th day after BSA immunization, and reached the highest level on the 12th day.The experimental group was significantly higher than the control group. The specific BSA-anti-BSA complex in the circulation of the two groups of animals was significantly higher than that before immunization, but there was no statistical difference between the two groups. The complement value in blood of the experimental group was significantly higher than that of the control group. 18- β Glycyrrhetinic acid has no effect on the formation of CIC.
Effect on digestive system:
Glycyrrhetinic acid can reduce blood bilirubin and increase urinary bilirubin excretion in rabbits and rats with ligation of the total bile duct, which is stronger than glucuronolactone or methionine. It has good anti-ulcer effect on pyloric ligation rats. Its treatment index is high.
FAQ
- What is glycyrrhetinic acid used for?
In conclusion, glycyrrhetinic acid is a multifaceted compound with a wide range of therapeutic applications. Its anti-inflammatory, antiviral, and antioxidant properties make it a valuable tool in the treatment of various conditions.
- Is 18 β-glycyrrhetinic acid in licorice root?
18 beta-Glycyrrhetinic acid (GRA) represents a major metabolite of glycyrrhizic acid (glycyrrhizin), an important constituent of licorice and licorice root, and is a potent inhibitor of 11 beta-hydroxysteroid dehydrogenase (11 beta OHSD).
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