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Synonym name: 4'-Dihydroxy-2-methoxychalcone
Catalogue No.: BP0521
Cas No.: 34221-41-5
Formula: C16H14O4
Mol Weight: 270.284
Botanical Source: tissue culture of Glycyrrhiza echinata, from Glycyrrhiza inflata and Bauhinia manca
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
Description:
Echinatin has significant antioxidant and anti-inflammary activities, it shows strong scavenging activity toward the ABTS + radical, it also inhibits the production of nitric oxide (NO), interleukin-6 (IL-6) and prostaglandin E2 (PGE2) in LPS-induced macrophage cells. Echinatin disturbs the mitochondrial energy transfer reactions and membrane permeability, at a low concentration cause deterioration of respiratory control and oxidative phosphorylation of isolated rat liver mitochondria, inhibits DNP-ATPase activity while stimulating range latent ATPase activity.
References:
J Toxicol Sci. 1982 Nov;7(4):245-54.
The effects of echinatin and its related compounds on the mitochondrial energy transfer reaction.
METHODS AND RESULTS:
To investigate the mechanism by which various biological action of licorice root are brought about, the effects of Echinatin as a small constituent of Glycyrrhiza echinata and several related compounds on mitochondrial energy transfer reactions were examined. The results obtained were as follows: 1) Echinatin, 4'-hydroxychalcone, chalcone and 3,4'-dihydroxychalcone at a low concentration cause deterioration of respiratory control and oxidative phosphorylation of isolated rat liver mitochondria. 2) Chalcone and 4'-hydroxychalcone stimulate both latent and DNP-ATPase activity of mitochondria. Echinatin inhibits DNP-ATPase activity while stimulating range latent ATPase activity in the low concentration. 3) Chalcone and 4'-hydroxychalcone induce a rapid potassium release from mitochondrial vesicles, while Echinatin and 3,4'-dihydroxychalcone have lesser effect than the former two substances.
CONCLUSIONS:
From these results, it can be concluded that Echinatin and several related compounds disturb the mitochondrial energy transfer reactions and membrane permeability.
Food Chem. 2013 Nov 15;141(2):1063-71.
Antioxidant and anti-inflammatory activities of six flavonoids separated from licorice.
Licorice, the roots and rhizomes of several Glycyrrhiza species (Leguminosae), is an important natural sweetening agent and a widely used herbal medicine.
METHODS AND RESULTS:
In this work, six flavonoids, 5-(1,1-dimethylallyl)-3,4,4'-trihydroxy-2-methoxychalcone (1), licochalcone B (2), licochalcone A (3), Echinatin (4), glycycoumarin (5) and glyurallin B (6), were isolated from the extracts of licorice (Glycyrrhiza inflata and Glycyrrhiza uralensis). Their structures were elucidated using various spectroscopic methods. To our knowledge, compound 1 was isolated from natural plants for the first time. All the isolates were tested by antioxidant and anti-inflammatory assays. Compounds 2, 4 and 5 showed strong scavenging activity toward the ABTS(+) radical, and compounds 1, 2, 3, 5 and 6 exhibited potent inhibition of lipid peroxidation in rat liver microsomes compared with the reference controls. Compounds 1-4 dose-dependently inhibited LPS induced reactive oxygen species (ROS) production in RAW 264.7 cells. Furthermore, compounds 1-5 were demonstrated to inhibit the production of nitric oxide (NO), interleukin-6 (IL-6) and prostaglandin E2 (PGE2) in LPS-induced macrophage cells. Moreover, the contents of the six compounds, in different Glycyrrhiza species, were quantified by HPLC-MS.
Chinese Journal of New Drugs, 2013, 22(21):2547-52.
Determination of antioxidant activity in licorice vitro metabolites by DPPH spiking coupled with HPLC-Q-TOF MS/MS
To investigate the antioxidant activity of liver microsomal metabolites from six flavonoids in licorice by 1, 1-diphenyl-2-picrylhydrazyl (DPPH) spiking coupled with HPLC-Q-TOF MS/MS.
METHODS AND RESULTS:
The six flavonoids were incubated with rat liver microsomes and the resultant metabolites were identified by HPLC-Q-TOF MS/MS. The antioxidant activity of the metabolites was calculated by comparing the peak area changes before and after incubation with DPPH. The peak area of the metabolites significantly decreased or even disappeared after incubation with DPPH. Besides the metabolites Lico A-M1 and Lico A-M2 of licochalcone A, more than 90% of other metabolites of flavonoids were oxidized.
CONCLUSIONS:
Liver microsomal metabolites of Echinatin, licochalcone B, licochalcone A, 5-(1, 1-dimethylally)-3, 4, 4'-trihydroxy-2-methoxychalcone, glycycourmarin and glyurallin B still have significant antioxidant activities.
HPLC of Echinatin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
66.7600
2.8440
2.8075
.0938
4.0863
11.8824
High
91.9442
2.0020
Yes
No
Yes
No
Yes
Yes
0.6
No
Yes
Yes
Yes
Echinatin, CAS number 34221-41-5, is a natural chalcone compound isolated from the traditional Chinese medicine Glycyrrhiza (Glycyrrhiza spp.). Licorice, as a commonly used medicinal material in traditional Chinese medicine, has attracted attention due to its various bioactive components. Among them, chalcone compounds have become a research hotspot due to their unique structure and significant pharmacological activity. Licorice chalcone has multiple pharmacological effects including liver protection, anti-inflammation, and anti-tumor effects, especially showing potential therapeutic value in regulating tumor-related signaling pathways.
In recent years, with the deepening of natural product pharmacology, the pharmacological mechanisms, molecular targets, and pharmacokinetic characteristics of licorice chalcone have gradually been revealed. Its rapid absorption and elimination in vivo, wide tissue distribution, and relatively low bioavailability provide important pharmacokinetic references for its clinical application. This paper aims to systematically review the chemical structure, plant origin, pharmacological activity, mechanism of action, druggability evaluation, and future clinical application prospects of licorice chalcone stingos, aiming to provide theoretical basis and reference for related research and drug development.
Licorice chalcone is a natural product of the chalcone family, with a molecular formula C_16H_14O_4 and a molecular weight of 270.2840. Its structural feature is a typical 1,3-diketone styrene skeleton with two aromatic rings connected by α β-unsaturated ketones, giving it unique chemical activity. In terms of physicochemical properties, the LogP value of licorice chalcone is 2.8440, indicating moderate lipid solubility, which is beneficial for cell membrane penetration and distribution in vivo. The polar surface area (TPSA) is 66.7600, indicating moderate polarity that aids binding to biomacromolecules. Low water solubility (0.0938 mg/mL), which may limit its oral absorption efficiency.
Additionally, licorice chalcone has demonstrated high blood-brain barrier penetration ability, suggesting its potential application value in central nervous system diseases. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test score was 0.6, indicating a low genotoxicity risk and meeting drug safety requirements.
Glycyrrhiza chalcone mainly comes from the roots of licorice species, especially licorice (Glycyrrhiza uralensis Fisch.). As a traditional Chinese medicine, licorice's rhizomes are rich in chalcone compounds. The extraction of licorice chalcone is usually done by solvent extraction, with ethanol or methanol commonly used as extraction solvents to ensure effective dissolution of chalcone-type components.
The extraction process generally includes the following steps: first, the licorice root is dried and crushed, then reflux extraction is performed with 70%-95% ethanol, followed by vacuum concentration to obtain the crude extract. The crude extract was separated by silica gel column chromatography and purified using solvent systems of different polarities (such as petroleum ether-ethyl acetate gradient elution), and finally confirmed by high-performance liquid chromatography (HPLC) to confirm the purity and content of licorice chalcone. In addition, in recent years, ultrasound-assisted extraction and microwave-assisted extraction technologies have been introduced to improve extraction efficiency and purity.
Licorice chalcone has shown significant liver-protective effects in multiple experiments. It alleviates liver damage by inhibiting hepatocyte inflammatory responses and oxidative stress. Animal model studies have shown that licorice chalcone can lower serum transaminase levels, alleviate pathological damage to liver tissue, and significantly inhibit the progression of liver fibrosis. Its mechanism of action may be related to regulating liver inflammatory factors and antioxidant enzyme activity.
Licorice chalcone has significant anti-inflammatory activity and can inhibit the release of various inflammatory mediators, such as tumor necrosis factor α (TNF-α), interleukin-6 (IL-6), and nitric oxide (NO). In vitro cell experiments showed that licorice chalcone exerts anti-inflammatory effects by inhibiting the nuclear factor κB (NF-κB) signaling pathway, reducing the expression of inflammation-related genes.
Research on licorice chalcone is becoming increasingly in-depth in the field of anti-tumor treatment, involving multiple tumor cell lines. It demonstrates broad-spectrum anti-cancer potential by regulating tumor cell apoptosis, inhibiting proliferation and migration. Specifically, it induces tumor cell apoptosis, blocks cell cycle progression, and inhibits the activity of tumor-related enzymes.
The antitumor activity of licorice chalcone is closely related to its multi-target regulation. Research shows that its main targets include:
The multiple regulation of these molecular targets enables licorice chalcone to demonstrate broad anticancer activity across various tumor types.
The druggability parameters of licorice chalcone indicated good drug development potential. The molecular weight was moderate (270.2840), and the LogP value was 2.8440, meeting the Lipinski rule, suggesting good oral absorption potential. TPSA is 66.7600, indicating moderate polarity that aids membrane penetration.
Pharmacokinetic studies show that licorice chalcone can be rapidly absorbed in rats, with rapid plasma concentration peaks, but its absolute bioavailability is only about 6.81%, suggesting some limitations in oral absorption, possibly related to low water solubility (0.0938 mg/mL) and first-pass effect. It is widely distributed in the body, especially capable of crossing the blood-brain barrier, and has potential central nervous system effects.
In terms of safety, the hERG channel inhibition test was negative, reducing the risk of cardiotoxicity. Ames test results showed low genotoxicity and met drug safety requirements.
As a natural chalcone compound with multiple pharmacological activities, licorice stinging chalcone shows broad clinical application prospects. Its remarkable liver-protecting, anti-inflammatory, and anti-tumor effects give it potential value in the treatment of liver diseases, inflammatory diseases, and tumors. Especially in the field of tumor treatment, by regulating tumor cell survival and metastasis through multi-target mechanisms, licorice chalcone is expected to become a candidate molecule for novel anticancer drugs.
However, its current low bioavailability and poor water solubility limit further advancement of clinical applications. Future research should focus on optimizing their drug formulations, such as nanocarriers and solid dispersions, to improve in vivo utilization and therapeutic efficacy. At the same time, in-depth analysis of its mechanism of action and toxicological characteristics, and systematic preclinical and clinical research will lay a solid foundation for its clinical translation.
Moreover, given its excellent blood-brain barrier penetration, the potential applications of licorice chalcone in neurological diseases are also worth further exploration.
As an important chalcone active ingredient in licorice, Chalcone has become a key subject of natural product pharmacological research due to its unique chemical structure and diverse pharmacological activities. It demonstrates significant biological effects in liver protection, anti-inflammation, and anti-tumor properties, and achieves comprehensive disease regulation through multi-target mechanisms. Despite challenges such as bioavailability and water solubility, licorice chalcone still demonstrates good druggability and safety, providing a solid foundation for future drug development and clinical application. With ongoing advances in formulation technology and molecular mechanism research, licorice chalcone is expected to play a greater role in the field of natural product drugs and become an effective candidate for treating various diseases.
Shenshuai
Wenjing
Hedandan
