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Product name: Apigenin-7-O-glucuronide
Synonym name: Scutellarin A
Catalogue No.: BP0179
Cas No.: 29741-09-1
Formula: C21H18O11
Mol Weight: 446.364
Botanical Source: Occurs in Antirrhinum majus, Phlomis tuberosa and Ruellia tuberosa
Physical Description: Yellow 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:
Apigenin 7-O-β-D-glucuronide(AG), an active flavonoid derivative isolated from the agricultural residue of Juglans sigillata fruit husks, possesses multiple pharmacological activities, including anti-oxidant, anti-complement, and aldose reductase inhibitory activities; AG protects mice from LPS-induced endotoxin shock by inhibiting proinflammatory cytokine production, suggests that AG may be used as a source of anti-inflammatory agents as well as a dietary complement for health promotion.[1]
References:
[1] Hu W, Wang X, Wu L, et al. Food Funct, 2016, 7(2):1002-13.
[2] Xue P, Zhao Y, Wang B, et al. J Chromatogr Sci, 2007, 45(4):216-9.
HPLC of Apigenin-7-O-glucuronide
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
218.4200
.5000
-2.5000
No
No
No
No
No
No
No
Apigenin-7-O-glucuronide (CAS No.: 29741-09-1), as an important flavonoid glucuronide compound, has attracted widespread attention in the field of natural product pharmacology in recent years. Flavonoids, due to their diverse biological activities and relatively low toxic side effects, have become hot topics in antiviral, anti-inflammatory, and anti-tumor treatment research. Apigenin-7-O-glucuronide is a metabolite modified by glucuronylated oxylation of apigenin, possessing unique physicochemical properties and biological activity, especially showing potential pharmacological value in the regulation of molecular targets related to HIV infection.
This review systematically summarizes the chemical structure and physicochemical properties of apigenin-7-O-glucuronidan, plant origin, and extraction methods, focusing on its pharmacological activity and mechanism of action. It analyzes its pharmacokinetic characteristics in combination with druggability parameters, explores its clinical application prospects in diseases such as HIV infection, and aims to provide a theoretical foundation and practical guidance for further research and development of this compound.
Apigenin-7-O-glucuronide is a glucuronide derivative among flavonoids, with a molecular formula of C_21H_18O_12 and a molecular weight of 446.36 Da. Structurally, this compound is formed by the syngenin parent nucleus binding to glucuronic acid via a 7-position hydroxyl group, forming a β-glucosidic bond, imparting it to high polarity and abundant hydrogen bond receptor sites. In terms of physicochemical properties, its LogP value is about 0.5, indicating good hydrophilicity, and the topological polar surface area (TPSA) reaches as high as 218.42 Ų, indicating that the molecule has strong polarity and extensive hydrogen bond formation ability, which significantly affects its bioavailability and membrane permeability.
Apigenin-7-O-glucuronide contains 11 hydrogen bond receptors and has a stable molecular structure, with no obvious aromatic ring disruption or easily degradable groups. Its polarity and molecular weight limit its ability to cross the blood-brain barrier (BBB permeability is not), which to some extent reduces the risk of central nervous system toxicity. Toxicological evaluation showed that this compound had no hepatotoxicity, cardiotoxicity, or hERG channel inhibitory effects, and the Ames-induced mutagenic test was negative, demonstrating a favorable safety profile.
Apigenin-7-O-glucuronic acid is widely found in various plants, especially in Apiaceae species such as celery (Apium graveolens), parsley (Petroselinum crispum), and other leafy green vegetables. As one of the main metabolites of apigenin, it often exists in plant tissues in free or bound forms, especially concentrated in leaves and stems.
The main methods for extracting this compound include solvent extraction, ultrasound-assisted extraction, and high-performance liquid chromatography (HPLC) separation and purification. Common extraction solvents include methanol, water, or ethanol aqueous solutions, and combining ultrasound-assisted technology can significantly improve extraction efficiency. After concentration, liquid-liquid distribution, and silica gel column chromatography pretreatment, the extract was separated and purified using reversed-phase HPLC, ultimately obtaining high-purity celegenin-7-O-glucuronic acid. In recent years, the application of supercritical CO_2 extraction and membrane separation technologies has also provided new ideas for the industrial extraction of this compound.
Pharmacological activity studies of apigenin-7-O-glucuronic acid mainly focus on antiviral, anti-inflammatory, and antioxidant aspects, especially showing unique advantages in the prevention and treatment of HIV infection.
Anti-HIV activity
Multiple in vitro experiments have shown that apigenin-7-O-glucuronic acid can inhibit viral entry and replication by regulating HIV-related targets such as CCR5, CXCR4, and CD4 receptors. Its regulatory effect on HIV co-receptors CCR5 and CXCR4 blocks the binding of the virus to host cells, reducing the infection rate. In addition, apigenin-7-O-glucuronide indirectly inhibits viral integrase and reverse transcriptase, providing multi-target support for its anti-HIV mechanism.
Anti-inflammatory effects
This compound exerts significant anti-inflammatory effects by inhibiting lipoxygenase (ALOX5) activity, reducing the formation of inflammatory mediators. Meanwhile, the regulation of acetylcholinesterase (ACHE) by celerylin-7-O-glucuronidase helps alleviate inflammation-related nerve damage and immune responses, demonstrating potential neuroprotective effects.
Antioxidant and cell protection
Apigenin-7-O-glucuronide has excellent free radical scavenging ability and can reduce cell damage caused by oxidative stress. In various cell models, it lowers ROS levels by activating endogenous antioxidant enzyme systems, protecting cells from oxidative damage.
Anti-tumor potential
Some studies indicate that this compound regulates the expression of topoisomerase IIα (TOP2A), affecting the DNA replication and repair processes of tumor cells, and possesses certain antitumor activity. Its multi-target mechanism offers new ideas for tumor treatment.
The bioactivity of apigenin-7-O-glucuronic acid is closely related to its multi-target regulation. Its main targets of action include key receptors and enzymes during HIV infection, including:
CCR5 and CXCR4: As co-receptors for HIV entry into host cells, apigenin-7-O-glucuronide binds to these two receptors, blocking the fusion of the viral envelope with the cell membrane and preventing viral invasion.
CD4 Receptor: As the main binding receptor for HIV, this compound regulates CD4 to help reduce the virus's affinity with host cells.
ABCG2 transporter: This protein is involved in drug efflux. Apigenin-7-O-glucuronic acid regulates ABCG2 expression and may affect intracellular accumulation and drug resistance.
ALOX5 (lipoxygenase 5): involved in the synthesis of inflammatory mediators, this compound inhibits its activity and reduces inflammatory responses.
TOP2A (Topoisomerase IIα): Regulates DNA replication and repair; the inhibitory effect of apigenin-7-O-glucuronide reveals potential antitumor mechanisms.
ADORA3 (adenosine A3 receptor) and ACE (acetylcholinesterase): involved in immune regulation and neuroprotection, the regulation of these targets by celenitin-7-O-glucuronide may help alleviate HIV-related neuroinflammation and cognitive impairment.
Additionally, this compound inhibits inflammatory responses induced by bacterial lipopolysaccharides (LPS), suggesting its potential in anti-infection and immunomodulatory applications.
From the perspective of druggability parameters, apigenin-7-O-glucuronide has good safety and drug compatibility. Its molecular weight (446.36 Da) is slightly above the ideal range recommended by Lipinski's rules, but still within an acceptable range. A LogP value of 0.5 indicates moderate hydrophilicity, which benefits distribution and metabolism in the body.
High TPSA (218.42 Ų) and a relatively high number of hydrogen bond receptors (11) suggest strong polarity, which may limit oral bioavailability and cell membrane penetration, especially difficulty crossing the blood-brain barrier and reducing potential toxicity risk in the central nervous system.
Toxicological assessment showed no hepatotoxicity, cardiotoxicity, or hERG channel suppression, and the Ames test was negative, indicating low genotoxicity risk and good safety.
Pharmacokinetics, apigenin-7-O-glucuronide is a glucuronic glycoside compound that may be hydrolyzed into apigenin in the intestines and liver by β-glucosidase, thereby exerting pharmacological effects. Its metabolic pathway mainly involves glucuronic acid binding and sulfation; the activity of these metabolites and their accumulation in vivo require further in-depth study.
Apigenin-7-O-glucuronic acid shows broad application prospects, especially in HIV infection prevention and treatment, due to its multi-target and multi-mechanism pharmacological activity. By regulating viral entry into receptors and inflammatory mediators, it can effectively inhibit viral replication and alleviate virus-related immune inflammatory responses, providing a new drug candidate for adjuvant HIV therapy.
Additionally, given its anti-inflammatory, antioxidant, and neuroprotective effects, the compound's potential applications in HIV-related neurocognitive disorders and other inflammatory diseases are also worth attention. Its good safety and low toxicity provide favorable conditions for clinical development.
Future research should focus on its in vivo pharmacokinetic characteristics, evaluation of metabolite activity, and formulation optimization to enhance bioavailability and targeting. At the same time, combining modern drug design technologies, such as nanocarrier systems and targeted delivery strategies, is expected to overcome the penetration limitations of biofilms caused by their strong polarity.
The implementation of preclinical and clinical trials will lay the foundation for validating its efficacy and safety, and promote the translation of apigenin-7-O-glucuronic acid to clinical application.
Apigenin-7-O-glucuronic acid, as an important natural flavonoid glucuronide, demonstrates potential value in the fight against HIV infection and related inflammatory diseases due to its unique chemical structure and multi-target pharmacological activity. Its excellent safety and druggability parameters provide a solid foundation for further development.
Although research on its pharmacokinetics and clinical applications is still in its early stages, with advances in natural product pharmacology and molecular pharmacology technologies, apigenin-7-O-glucuronide is expected to become an important candidate for novel antiviral and anti-inflammatory drugs. In the future, it is necessary to strengthen mechanistic research, drug design, and clinical validation to move from the laboratory to clinical application, benefiting patients.
Shenshuai
Wenjing
Hedandan
