Product name: calycosin-7-O-beta-D-glucoside
Synonym name: Calycosin-7-O-β-D-glucoside; Calycosin 7-glucoside
Catalogue No.: BP0306
Cas No.: 20633-67-4
Formula: C22H22O10
Mol Weight: 446.408
Botanical Source: Baptisia and Thermopsis spp.
Physical Description: Powder
Type of Compound: Flavonoids
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, up to kilograms
Inquire for bulk scale.
Descriptions:
Calycosin-7-O-β-d-glucoside(CG) treatment can significantly reduce infarct volume, histological damage and BBB permeability in the in vivo MCAO ischemia–reperfusion rat model; inhibit the expression and activities of MMPs, and secure the expression of cav-1 and tight junction proteins in the microvessels isolated from ischemic rat cortex; scavenge NO, inhibit the activities of MMP-2 and MMP-9, and attenuate cell death in the in vitro cultured brain microvascular endothelial cells under OGD condition; thus CG could protect BBB integrity in experimental cerebral ischemia–reperfusion injury via regulating NO/cav-1/MMPs pathway.[1]
Calycosin-7-O-β-D-glucoside can promote oxidative stress-induced cytoskeleton reorganization through integrin-linked kinase signaling pathway in vascular endothelial cells.[2]
Calycosin-7-O-β-d-glucoside attenuates ischemia-reperfusion injuryin vivovia activation of the PI3K/Akt pathway.[3]
Calycosin-7-O-β-D-glucoside has effects on cell apoptosis in cervical cancer HeLa cells and expression of Bcl-2/Bax.[4]
References:
[1] Fu S, Gu Y, Jiang J Q, et al. J Ethnopharmacol. 2014,155(1): 692–701.
[2] Jiang Y H, Sun W, Li W, et al. Bmc Compl Altern M, 2015, 15(1):1-11.
[3] Ren M, Wang XD, Du G Q, et al. Mol Med Rep, 2015, 13(1):235–45.
[4] Zhang D M. Chinese Traditional & Herbal Drugs, 2015, 46(10):1498-502.
[5] Song C Y, Feng J F. Chinese J Exp Trad Med Formulae, 2013, 19(11):115-7.
HPLC of calycosin-7-O-beta-D-glucoside
NMR of calycosin-7-O-beta-D-glucoside
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
Calycosin-7-O-beta-D-glucoside (hereinafter referred to as calycosin-7-O-beta-D-glucoside), as an important natural glycooxy-isoflavone, has attracted widespread attention in the field of natural product pharmacology in recent years. This compound is a derivative formed by the hydroxyl group at the 7-position of the triphylloid isoflavone modified by a glycosidic bond of β-D-pyran glucosyl residues, featuring unique chemical structure and biological activity. Isoflavonoid polysides, which are widely found in various traditional Chinese medicinal materials, especially traditional medicinal plants such as Astragalus membranaceus, are one of its main active components. In recent years, with in-depth research into its pharmacological effects and molecular mechanisms, capillary isoflavone glycosides have shown significant potential in antioxidant, anti-inflammatory, immunomodulatory, and neuroprotective aspects, making them important candidate molecules for natural drug development.
This paper aims to systematically review the chemical structure and physicochemical properties of hairy isoflavone glycosides, plant origins and extraction methods, with a focus on evaluating their pharmacological activity and mechanism of action. Combined with druggability evaluation and pharmacokinetic data, it explores their clinical application prospects and development trends, providing theoretical basis and reference for subsequent basic research and drug development.
The molecular formula of capillary isoflavone glycoside is C_22H_22O_10, with a molecular weight of 446.40. Its structural feature is that the 7-hydroxyl group of the hairy isoflavone forms a glycosidic bond through the β-D-pyran glucosyl residue, making it a 4'-methoxyisoflavone compound. This structure imparts high polarity and water solubility, resulting in a low LogP value (-2.1), reflecting strong hydrophilicity that facilitates absorption and distribution in the body.
The topological pole surface area (TPSA) of the hairy isoflavone glycoside is 217.41 Ų, with 10 hydrogen bond acceptors and a relatively large number of hydrogen donors. These physicochemical parameters suggest its strong hydrophilicity and binding ability in intermolecular interactions. Its structure contains multiple phenolic hydroxyl and methoxy groups, which form the important basis for its antioxidant activity.
From a pharmacokinetic perspective, the low permeability of the blood-brain barrier of hairy isoflavone glycosides suggests that its direct effect in the central nervous system may be limited; At the same time, it showed no hepatotoxicity, cardiotoxicity, or hERG channel inhibition, and the Ames test was negative, demonstrating good safety and low risk of mutagenics.
The isoflavone glycoside of the hairy is mainly found in the leguminous plant Astragalus (Astragalus membranaceus) and related species, and is one of the representative isoflavones in astragalus. As a traditional Chinese medicinal herb, Astragalus has effects such as tonifying qi, strengthening the surface, promoting urination, and reducing swelling. Its pharmacological effects are closely related to active ingredients such as hairy isoflavone glycosides.
Common methods for extracting Morrin Isoflavone Glycosides include solvent extraction, ultrasound-assisted extraction, and high-performance liquid chromatography (HPLC) separation and purification. Typically, methanol or ethanol aqueous solutions are used as extractants, combined with ultrasonic or reflux extraction techniques to improve extraction efficiency. After concentration, liquid-liquid separation, and chromatographic separation, high-purity hairy isoflavone glycosides can be obtained.
In recent years, with the development of green extraction technologies, emerging technologies such as supercritical fluid extraction and microwave-assisted extraction have also been applied to extract metriol isoflavone glycosides, significantly improving extraction efficiency and purity, and reducing solvent usage and environmental pollution.
Kerosiflavone glycosides exhibit multiple pharmacological activities, especially in the field of antioxidant damage. Its main pharmacological effects include:
Antioxidant effects
Kerosoflavone glycosides can effectively eliminate free radicals and reduce cell damage caused by oxidative stress. Cell and animal experiments have shown that hairy isoflavone glycosides significantly reduce reactive oxygen species (ROS) levels by enhancing antioxidant enzyme activities such as superoxide dismutase (SOD1, SOD2), catalase (CAT), and glutathione peroxidase (GPX1), thereby protecting cells from oxidative damage.
Anti-inflammatory effects
Hair isoflavone glycosides can inhibit the release of inflammatory mediators and reduce inflammatory responses. It exerts anti-inflammatory effects by regulating the nuclear factor κB (NF-κB) signaling pathway, reducing the expression of pro-inflammatory cytokines such as TNF-α and IL-6.
Immune regulation
Research shows that metrifolin isoflavone glycosides can enhance the body's immune function, promote macrophage phagocytic activity and lymphocyte proliferation, regulate immune balance, and help resist pathogen infections.
Neuroprotective effects
Although the blood-brain barrier permeability of the metrifolin isoflavone glycoside is relatively low, it protects nerve cells through antioxidant and anti-inflammatory mechanisms, reduces nerve damage, and demonstrates potential value in preventing and treating neurodegenerative diseases.
Cardiovascular protection
Corticosides, through antioxidant, anti-inflammatory, and improved vascular endothelial function, reduce the risk of cardiovascular diseases, and provide certain cardiovascular protective effects.
The pharmacological effects of capillary isoflavone glycosides mainly occur by regulating intracellular antioxidant and anti-inflammatory signaling pathways. Its key molecular targets include:
NFE2L2/NRF2 (nuclear factor red blood cell 2-related factor 2)
Kerolide isoflavone glycosides can activate the NRF2 signaling pathway, promoting its cytoplasmic translocation to the nucleus, binding to antioxidant response elements (ARE), and upregulating downstream antioxidant enzyme gene expression such as SOD1, SOD2, CAT, GPX1, and HMOX1 (heme oxygenase 1), enhancing cellular antioxidant capacity and reducing oxidative stress damage.
Antioxidant enzyme system
Methylisoflavone glycosides directly or indirectly regulate the activities of antioxidant enzymes such as SOD, CAT, and GPX, eliminate excess reactive oxygen species, and protect cell structure and function.
Anti-inflammatory signaling pathway
By inhibiting the expression of NF-κB and related pro-inflammatory factors, capillary isoflavone glycosides reduce inflammatory responses and protect tissues from inflammation-mediated damage.
Regulation of apoptosis
Hairy isoflavone glycosides can also regulate the expression of Bcl-2 family proteins, inhibit apoptosis, and promote cell survival, especially evident under oxidative stress environments.
In summary, capillary isoflavone glycosides achieve broad biological effects through multi-target and multi-pathway synergistic effects.
Druggability evaluation of capillary isoflavone glycosides shows good safety and relatively ideal pharmacokinetic characteristics:
Security
In vitro and in vivo toxicological studies have shown that capillary isoflavone glycosides do not have significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition; Ames tests are negative, indicating low mutagenic risk and relatively high safety.
Pharmacokinetics
Kerenosides, which have good water solubility, have high polarity and TPSA that limit their oral bioavailability. Research shows that moretiflavone glycosides can be partially hydrolyzed in the gastrointestinal tract into metrifolone isoflavones, which have good lipid solubility and bioavailability, suggesting that their metabolism in the body has an important impact on drug efficacy.
Blood-brain barrier permeability
Due to the low and high polarity of LogP, metrifolone glycoside itself has limited ability to penetrate the blood-brain barrier, which restricts its direct application in central nervous system diseases, though its metabolites may play a role.
Drug interactions
Currently, there is limited research on interactions between mezzolytic isoflavone glycosides and other drugs, and further evaluation of its safety in multidrug combination therapy is needed in the future.
As a natural glycolytic isoflavone, hairy isoflavone glycosides have broad application prospects in the prevention and treatment of various diseases due to their remarkable antioxidant and anti-inflammatory activities. Especially in chronic inflammation, oxidative stress-related diseases such as cardiovascular diseases, neurodegenerative diseases, diabetes, and their complications, metrifolin isoflavone glycosides show potential therapeutic value.
Future clinical research should focus on the following aspects:
Pharmacokinetics and dosage form optimization
To address the low oral bioavailability of metrixin isoflavone glycosides, novel delivery systems (such as nanocarriers, liposomes, etc.) have been developed to improve in vivo stability and targeting.
Clinical safety and efficacy evaluation
Systematic clinical trials have been conducted to clarify the efficacy and safe dosage range of capillary isoflavone glycosides in different diseases, providing scientific evidence for their clinical application.
Research on multi-target mechanisms
In-depth analysis of the mechanism of the action of capillary isoflavone glycosides in cellular signaling networks, uncovering its potential drug targets, and promoting the formulation of precision treatment strategies.
Combination medication strategies
Exploring the synergistic effects of metrifolin isoflavone glycosides with existing drugs to enhance efficacy, reduce side effects, and expand their clinical applications.
As an important natural glycooxyisoflavone, metrixy isoflavone glycosides have become a hot topic in natural product pharmacology research due to their unique chemical structure and diverse biological activities. Its significant effects in antioxidant, anti-inflammatory, and immune regulation provide new ideas and potential drug candidates for the prevention and treatment of various chronic diseases. Although its clinical application is still in its early stages, with further optimization of pharmacokinetics and deeper mechanistic research, mechanistic glycosides are expected to become an important direction for natural drug development. In the future, by combining modern drug development technology with clinical validation, the medicinal value of Maorin Isoflavone Glycosides will be further explored and applied.
