Product name: Afzelin

Synonym name: Kaempferol-3-rhamnoside; Kaempferin; Afzeloside

Catalogue No.: BP0818
Cas No.: 482-39-3
Formula: C₂₁H₂₀O₁₀
Mol Weight: 432.381
Botanical Source: Afzelia sp. heartwood and many other plant spp. incl. ferns
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:
Afzelin, isolated from Cornus macrophylla, has antibacterial effects on Pseudomonas aeruginosa, its minimum inhibitory concentration (MIC) is 31 μg/mL.[1]
Afzelin has several cellular activities such as DNA-protective, antioxidant, and anti-inflammatory as well as UV-absorbing activity and may protect human skin from UVB-induced damage by a combination of UV-absorbing and cellular activities.[2]
Afzelin has potenial anti-cancer activity against prostate cancer, the activity is due to inhibition of LIM domain kinase 021 expression, it can inhibit the proliferation of LNCaP and PC302cells, and block the cell cycle in the G002phase.[3]
Afzelin can attenuate asthma phenotypes is based on reduction of Th2 cytokine via inhibition of GATA-binding protein 3 transcription factor, which is the master regulator of Th2 cytokine differentiation and production.[4]
Afzelin promotes melanogenesis by occurs through increased MITF gene expression, which is mediated by activation of p38 MAPK, and suggest that afzelin may be useful as a protective agent against ultraviolet irradiation. [5]

References:
[1] Lee S Y, So Y J, Shin M S, et al. Molecules, 2014, 19(3):3173-80.
[2] Shin S W, Jung E, Kim S, et al. Plos One, 2013, 8(4):e61971-e61971.
[3] Zhu K C, Sun J M, Shen J G, et al. Oncol Lett, 2015, 10(4):2359-65.
[4] Zhou W, Nie X. Mol Med Rep, 2015, 12(1):71-6.
[5] Jung E, Jin H K, Mi O K, et al. Chem-Biol Interact, 2016, 254:167-72.
[6] Huo L, Chen X H, Cao Y, et al. Chinese J Pharm Anal, 2010(05):831-3.

HPLC of Afzelin

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

Afzelin (CAS number: 482-39-3) is a natural flavonol glycoside, chemically named Kaempferol-3-O-rhamnoside. As an important member of flavonoid compounds, alfoudridin has attracted widespread attention in pharmacology and natural product chemistry due to its diverse biological activities. In recent years, with in-depth research into the pharmacological mechanisms of natural products, alfowedroside has shown significant potential in anti-inflammation, antioxidant stress control, anti-apoptosis, and cardiac protection, making it an important candidate for exploring novel therapeutic strategies.

This review aims to systematically summarize the chemical structure and physicochemical properties of alfowedrin, its plant origins and extraction methods, with a focus on evaluating its pharmacological activity and mechanism of action. Combined with the latest molecular target studies, it explores its druggability and pharmacokinetic characteristics, and finally looks ahead to its clinical application potential and future research directions, providing comprehensive theoretical basis and practical guidance for researchers in related fields.

Chemical structure and physicochemical properties

Alfosudin belongs to the flavonol glycoside class, with its basic backbone being a flavonol—quercetin (Kaempferol), which attaches a rhamnose sugar group at the 3-position hydroxyl group, hence the name Kaempferol-3-O-rhamnoside. Its molecular formula is C21H20O10, and its molecular weight is 432.3810. Its molecular structure contains multiple hydroxyl groups, giving it excellent hydrophilicity and antioxidant activity.

In terms of physicochemical properties, the LogP value of alfoudroside is about 0.8906, indicating moderate lipid solubility, which is beneficial for distribution in the body but not easily accumulated in lipid environments. The polar surface area (TPSA) is 170.05 Ų; a higher polar surface area suggests better water solubility (about 0.7505), but may limit its ability to penetrate cell membranes. The blood-brain barrier has low permeability, suggesting limited distribution in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test result was 0.6, indicating a low genotoxicity risk and meeting preliminary safety requirements.

Plant Origins and Extraction Methods

Alfodin is widely found in various plants, especially in traditional Chinese medicine and edible plants. Typical sources include plants rich in quercetin, such as Afzelia spp., ginkgo leaves, maple leaves, and various herbaceous plants. Its content is greatly influenced by plant species, growing environment, harvest time, and location.

Common methods for extracting alfowroside: solvent extraction, ultrasound-assisted extraction, and high-performance liquid chromatography (HPLC) separation and purification. Typically, methanol or ethanol aqueous solutions are used as extraction solvents, combined with ultrasound-assisted technology to improve extraction efficiency. The extract undergoes steps such as concentration, liquid-liquid extraction, and silica gel column chromatography, followed by purity testing and separation by HPLC. In recent years, green extraction technologies such as supercritical CO2 extraction and microwave-assisted extraction have gradually been applied to the efficient extraction of alfoudridin, improving yield and purity and reducing environmental impact.

Pharmacological activity research

The pharmacological activities of alfowuside cover multiple aspects, including anti-inflammation, antioxidant, anti-apoptotic, cardiotoxicity, and immunomodulatory effects, demonstrating its potential as a multi-target natural product.

Anti-inflammatory effects

Multiple in vivo and in vitro experiments have shown that alfoudroside can significantly inhibit the release of inflammatory mediators, such as tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and nitric oxide (NO). It regulates the nuclear factor κB (NF-κB) signaling pathway, reduces the expression of pro-inflammatory cytokines, and alleviates tissue inflammatory responses. For example, in ovalbumin-induced asthma models, alfoudridine significantly reduced airway inflammatory cell infiltration and mucus secretion, demonstrating good anti-allergic and anti-asthmatic activity.

Antioxidant stress

Alfoudaside has a powerful free radical scavenging ability, inhibiting reactive oxygen species (ROS) and lipid peroxidation, protecting cells from oxidative damage. By activating the NFE2L2/NRF2 signaling pathway, it induces the expression of downstream antioxidant enzymes such as superoxide dismutase (SOD1, SOD2), catalase peroxidase (CAT), glutathione peroxidase (GPX1), and heme oxygenase-1 (HMOX1), thereby enhancing cellular antioxidant defense capabilities.

Anti-apoptosis and cardiac protection

Alfoudaside can reduce mitochondrial damage, enhance mitochondrial biosynthesis, regulate mitochondria-related protein expression, and lower the levels of putative kinase 1 induced by Parkin and PTEN, thereby inhibiting apoptosis signaling. This mechanism is particularly prominent in heart cell protection, helping to prevent doxorubicin (HY-15142A)-induced cardiotoxicity. Animal experiments have shown that alfoudridin significantly improves the survival rate of D-galactosamine (GalN)/lipopolysaccharide (LPS) treatment of mice, reducing liver and heart damage.

Neuroprotective effects

Alfoudaside has a protective effect against scopolamine (HY-N0296)-induced nerve damage, possibly slowing nerve cell damage and apoptosis through antioxidant and anti-inflammatory mechanisms, suggesting its potential application value in neurodegenerative diseases.

Immune regulation

In the allergic disease model, alfoudridin demonstrates good immunomodulatory function by regulating Th1/Th2 cell balance, inhibiting IgE production, and alleviating allergic reactions.

Mechanism of action and molecular targets

The multiple pharmacological effects of alfowroside are attributed to its regulation of multiple signaling pathways and molecular targets, mainly including:

• NFE2L2/NRF2 pathway: Alfoudaside activates NRF2 nuclear translocation, promotes the expression of antioxidant enzyme genes, enhances cellular antioxidant capacity, and alleviates oxidative stress damage.
• Antioxidant enzyme system: Upregulates key enzyme activities such as SOD1, SOD2, CAT, GPX1, and HMOX1, clears ROS, and protects cell function.
• Mitochondrial function regulation: By lowering the levels of pseudative kinase 1 induced by Parkin and PTEN, mitochondrial biosynthesis is promoted, reducing mitochondrial membrane potential loss and apoptosis.
• Inhibition of NF-κB signaling pathway: suppresses the expression of pro-inflammatory factors and alleviates inflammatory responses.
• Immunomodulatory targets: Regulate the Th1/Th2 cell ratio and inhibit IgE-mediated allergic reactions.

The synergistic effect of these mechanisms enables alfowdine to exert protective effects in various pathological states, highlighting its advantages as a multi-target drug.

Druggability evaluation and pharmacokinetics

The druggability parameters of alfowroside indicate that it has certain development potential. A molecular weight of 432.3810 falls within the range of Lipinski's rule, and a LogP value of 0.8906 indicates moderate lipid solubility, which is beneficial for drug absorption and distribution. The high TPSA value and water solubility suggest that its oral bioavailability may be limited, and its low blood-brain barrier permeability restricts its application in the central nervous system.

In vitro safety evaluations showed that alfoudroside does not inhibit hERG channels, reducing the risk of cardiotoxicity. A negative Ames test indicates a low genotoxicity risk and meets drug safety requirements.

Currently, pharmacokinetic data on alfowroside are relatively limited. Previous studies have shown that its oral absorption is slow and its bioavailability is limited, possibly due to its high polarity and glycoside structure. The metabolic pathway mainly involves the liver enzyme system. After glycosidic bond hydrolysis, quercetin is released, which is further metabolized into various flavonoid metabolites. In the future, further systematic pharmacokinetic and toxicological studies are needed to clarify its in vivo behavior and safety.

Prospects and outlooks for clinical applications

With its multi-target and multifunctional pharmacological properties, alfowroside shows broad clinical application prospects in anti-inflammation, antioxidant, cardioprotective, and immunomodulatory fields. Especially in cardiovascular diseases, neurodegenerative diseases, allergic diseases, and liver damage, alfoudridin is expected to become a natural medicine or a new option for adjunctive therapy.

However, clinical research on alfowdin is still in its early stages and lacks systematic clinical trial data. Future research should focus on:

1. Pharmacokinetic optimization: Enhancing bioavailability and targeting through structural modification, nanocarriers, and other means.
2. In-depth analysis of the mechanism of action: Combining multi-omics techniques, revealing its systematic regulatory network.
3. Safety Evaluation: Conduct long-term toxicology and drug interaction studies to ensure clinical safety.
4. Clinical trial design: Advance clinical validation of alfoudridine in related diseases, clarify efficacy and dosage ranges.

Additionally, as a representative of natural products, alfoudridin's structural foundation provides an important template for developing novel flavonoid drugs, and in the future, through drug design and synthesis optimization, derivatives with greater clinical value are expected to be developed.

Conclusion

Alfodrid glycosides, as natural flavonol glycosides with multiple pharmacological activities, demonstrate a wide range of biological functions and good safety. Its mechanisms of action in anti-inflammation, antioxidant, cardioprotective, and immunomodulatory are gradually becoming clearer, providing an important example for pharmacological research of natural products. Although clinical applications still face challenges such as insufficient bioavailability and systematic research, with advances in modern drug development technology, alfoudridine is expected to become an important candidate for natural drug development, driving innovation in treatment strategies for related diseases.

In the future, multidisciplinary collaboration combining molecular pharmacology, pharmacokinetics, and clinical research will further promote the translational application of alfoudroside and realize its unique value in the field of natural product pharmacology.