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Product name: (18β,20α)-Glycyrrhizic acid
Synonym name: Licoricesaponin H2; Glycyrrhizic Acid Impurity 2
Catalogue No.: BP2052
Cas No.: 118441-85-3
Formula: C42H62O16
Mol Weight: 822.942
Botanical Source: Glycyrrhiza uralensis fisc
Physical Description: 甘草
Type of Compound: Triterpenoids
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
267.0400
2.3502
-.6105
.1276
.5203
.4612
Low
84.8265
5.9290
No
No
Yes
No
Yes
No
0.0
Yes
No
No
No
18β,20α-Glycyrrhizic acid ((18β,20α)-Glycyrrhizic acid, CAS No.: 118441-85-3) is an important natural triterpene saponin compound, mainly found in licorice (Glycyrrhiza spp.). As one of the most representative active components in licorice, 18β,20α-glycyrrhizic acid has attracted attention for its unique chemical structure and diverse biological activities. In recent years, with the development of natural product pharmacology and molecular biology technologies, the mechanisms of 18β,20α-glycyrrhizic acid in anti-inflammation, antiviral, liver protection, and immune regulation have gradually been revealed, demonstrating broad clinical application potential.
This paper aims to systematically review the chemical structure and physicochemical properties of 18β,20α-glycyrrhizic acid, plant origin and extraction methods, pharmacological activity and mechanism, druggability evaluation, and pharmacokinetic characteristics, and to look ahead to its future application prospects in disease treatment, providing comprehensive and in-depth reference for researchers in related fields.
18β,20α-glycyrrhizic acid has a molecular formula of C42H62O16 and a molecular weight of 822.9420. Its structure belongs to the triterpene saponin class, with the triterpene nucleus of glycyrrhizizi acid forming a disaccharide structure by connecting two glucose residues. The compound's stereotypes are 18β and 20α, giving it a specific spatial conformation that affects its binding affinity with biological targets.
In terms of physicochemical properties, the LogP value of 18β,20α-glycyrrhizic acid is 2.3502, indicating moderate lipophilusity, which facilitates cell membrane penetration without excessive hydrophobicity. The polar surface area (TPSA) is 267.0400, indicating that its molecules possess strong polarity and hydrogen bond donor/acceptor capabilities, which are crucial for their water solubility and interaction with target proteins. Water solubility is 0.1276, indicating low solubility in water and potentially limiting oral bioavailability. The blood-brain barrier has relatively low penetration ability, suggesting it mainly acts on peripheral tissues. The hERG channel inhibition test was negative, indicating a low cardiotoxicity risk, while the Ames mutagenic test result was 0.0, indicating a low genotoxicity risk and meeting safety requirements.
18β,20α-Glycyrrhizic acid is mainly found in plants of the genus Licorice, especially in the roots and rhizomes of licorice (Glycyrrhiza glabra, Glycyrrhiza uralensis, etc.). Licorice, as a traditional Chinese medicinal herb, has a long history and is widely used in traditional Chinese medicine formulations. Its roots contain abundant glycyrrhizic acid saponins, with 18β,20α-glycyrrhizic acid being one of the important components.
There are various extraction methods, commonly including water extraction and alcohol precipitation, ultrasound-assisted extraction, microwave-assisted extraction, and supercritical CO2 extraction. The traditional water extraction and alcohol precipitation method is widely adopted due to its ease of operation and low cost. The specific steps are: crush dried licorice roots, extract them by reflux with water or 70% ethanol, concentrate the filtrate, add ethanol to precipitate impurities, and then undergo multiple recrystallizations and purification to obtain high-purity 18β,20α-glycyrrhizic acid. Ultrasound and microwave-assisted extraction technologies can improve extraction efficiency and purity, shorten extraction time, and are suitable for industrial production. Supercritical CO2 extraction has gradually attracted attention in recent years due to its green and environmentally friendly advantages and strong selectivity.
During purification, column chromatography (such as silica gel columns and reversed-phase C18 columns) and high-performance liquid chromatography (HPLC) techniques are often used for separation and identification to ensure product quality and stability.
18β,20α-glycyrrhizic acid exhibits a variety of significant pharmacological activities, covering anti-inflammatory, antiviral, hepatprotective, immunomodulatory, antioxidant, and antitumor fields.
Multiple in vivo and in vitro experiments have shown that 18β,20α-glycyrrhizic acid can significantly inhibit the production of inflammatory mediators, such as tumor necrosis factor α (TNF-α), interleukin-1β (IL-1β), and interleukin-6 (IL-6). It inhibits the transcriptional expression of inflammatory genes by downregulating the nuclear factor κB (NF-κB) signaling pathway, thereby reducing tissue inflammatory responses. In animal models, 18β,20α-glycyrrhizic acid showed good alleviating effects on inflammatory diseases such as arthritis, pneumonia, and enteritis.
18β,20α-glycyrrhizic acid exhibits inhibitory effects on various viruses, including hepatitis B virus (HBV), hepatitis C virus (HCV), influenza virus, and novel coronavirus (SARS-CoV-2). Its mechanism involves blocking the viral replication cycle, inhibiting viral protein synthesis, and regulating the host's immune response. Especially in hepatitis B treatment, 18β,20α-glycyrrhizic acid enhances the body's antiviral ability by enhancing the interferon signaling pathway.
As an isomer of glycyrrhizic acid, 18β,20α-glycyrrhizic acid has shown significant effects in liver protection. It alleviates liver cell damage through antioxidant, anti-inflammatory, and regulating apoptosis. Preclinical studies have shown that this compound can improve liver fibrosis, fatty liver, and drug-induced liver injury, promote hepatocyte regeneration, and has potential value as an adjunct therapy for liver diseases.
18β,20α-glycyrrhizic acid can regulate immune cell function, enhance the activity of macrophages and lymphocytes, and promote cytokine balance. Its bidirectional regulatory effect on the immune system helps maintain immune homeostasis and reduces autoimmune diseases triggered by excessive immune responses.
This compound has the ability to scavenge free radicals, reduce oxidative stress, and protect cells from oxidative damage. In tumor models, 18β,20α-glycyrrhizic acid exerts certain antitumor activity by inducing apoptosis, inhibiting proliferation and migration of cancer cells, especially in digestive system tumors such as liver and stomach cancers.
The multi-target mechanism of 18β,20α-glycyrrhizic acid forms the basis of its broad pharmacological activity. The main issues involved are the following signaling pathways and molecular targets:
As a core regulator of inflammatory responses, NF-κB plays a key role in various diseases. 18β,20α-glycyrrhizic acid inhibits the phosphorylation and degradation of IκBα, blocks NF-κB nuclear translocation, reduces the expression of inflammatory factor genes, and achieves anti-inflammatory effects.
This compound can regulate ERK, JNK, and p38 kinases in the mitogen-activated protein kinase (MAPK) signaling pathway, affecting cell proliferation, differentiation, and apoptosis, and participating in anti-inflammatory and antitumor effects.
18β,20α-glycyrrhizic acid activates the PI3K/Akt signaling pathway, promoting cell survival and anti-apoptosis, and protecting hepatocytes from damage. At the same time, regulation of this pathway helps regulate immune responses and metabolic balance.
This compound affects macrophage surface receptors such as TLR4 (Toll-like receptor 4), regulates downstream MyD88-dependent signaling, and controls inflammation and immune responses. Additionally, 18β,20α-glycyrrhizic acid can regulate the ratio of regulatory T cells (Treg) to effector T cells, maintaining immune homeostasis.
18β,20α-glycyrrhizic acid blocks viral replication by inhibiting viral RNA-dependent RNA polymerase (RdRp) and viral protease activity. It can also enhance the interferon signaling pathway, promoting the expression of antiviral proteins.
The molecular weight of 18β,20α-glycyrrhizic acid is 822.9420, slightly above the ideal range for traditional small molecule drugs, which may affect oral absorption. LogP is 2.3502, indicating moderate lipid solubility and favorable cell membrane penetration. TPSA as high as 267.0400 suggests strong polarity, which may limit its passive diffusion. Low water solubility (0.1276) may limit the dissolution rate of oral formulations.
The low penetration capacity of the blood-brain barrier indicates that it mainly acts on peripheral tissues, reducing the risk of central nervous system side effects. hERG channel inhibition was negative and Ames test was zero, indicating low cardiotoxicity and genotoxicity risks and good safety.
Current studies show that 18β,20α-glycyrrhizic acid is slowly absorbed orally and has limited bioavailability, mainly entering the bloodstream through intestinal absorption. It is widely distributed in the body, with higher concentrations in the liver and kidneys. The metabolic pathway mainly involves hepatic enzyme-mediated hydrolysis and glucosidic bond breaking, producing glycyrrhizic acid monosaccharides and triterpene nuclei derivatives. Excretion is mainly through bile and urine.
Its moderate half-life supports its potential as an adjunct treatment for chronic diseases. To improve its pharmacokinetic properties, researchers have tried strategies such as nanocarriers, liposome encapsulation, and structural modification to enhance bioavailability and targeting.
18β,20α-glycyrrhizic acid, with its multi-target and multi-mechanism pharmacological properties, demonstrates broad application potential in the treatment of various diseases.
As a liver protectant, 18β,20α-glycyrrhizic acid holds significant value in adjunctive therapy for hepatitis, liver fibrosis, fatty liver, and drug-induced liver injury. Combining its anti-inflammatory and antioxidant effects, it is expected to be developed as a safe and effective new drug for liver disease treatment.
For chronic inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease, 18β,20α-glycyrrhizic acid can serve as a natural anti-inflammatory drug to reduce the side effects of long-term immunosuppressant use.
In the prevention and treatment of hepatitis B, hepatitis C, and emerging viral infections (such as COVID-19), the antiviral and immunomodulatory effects of 18β,20α-glycyrrhizic acid provide a theoretical basis for clinical application. In the future, it can be used in combination with existing antiviral drugs to improve efficacy and reduce the risk of resistance.
Although its antitumor activity is still in the early research stage, its synergistic effect with chemotherapy drugs offers new ideas for comprehensive tumor treatment.
18β,20α-Glycyrrhizic acid, as an important triterpene saponin active ingredient in licorice, has become a hot topic in natural product pharmacology research due to its unique chemical structure and diverse pharmacological activities. Its potential in anti-inflammation, antiviral, liver protection, and immune regulation provides rich theoretical foundations and application prospects for natural drug development and disease treatment. In the future, by integrating modern drug design and formulation technology, 18β,20α-glycyrrhizic acid is expected to become a new type of safe and effective therapeutic drug, contributing greater value to human health.
Shenshuai
Wenjing
Hedandan
