Synonym name: Kaempferol 3,7-dirhamnoside; Lespedin
Catalogue No.: BP0819
Cas No.: 482-38-2
Formula: C₂₇H₃₀O₁₄
Mol Weight: 578.523
Botanical Source: Cinnamomum sieboldii, Indigofera arrecta, Lespedeza cyrtobotrya and many other plant spp.

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.

HPLC of Kaempferitrin

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

Introduction/Overview

Kaempferitrin (CAS No.: 482-38-2) is a natural flavonoid glycoside compound widely found in various plants, especially the above-ground parts of broad beans (Vicia faba) and lotus flowers (Nelumbo nucifera). As a disaccharide derivative of kaempferol, kaempferol has attracted significant attention in traditional medicine due to its diverse biological activities. In recent years, with the development of natural product pharmacology, kanaside has become a research hotspot due to its significant pain-relieving, anti-inflammatory, antidiabetic, anti-tumor, and chemotherapy adjunctive effects. By activating insulin signaling pathways and modulating various cellular signaling molecules, it demonstrates broad pharmacological potential. In addition, the roles of sinacilate in antidepressant, bone density maintenance, immune regulation, and antioxidant damage have gradually been revealed, providing a theoretical basis for its clinical application. This paper will systematically review the chemical structure, plant origin, pharmacological activity, and mechanism of action of kasanamide, evaluate its druggability, and future clinical application prospects.

Chemical structure and physicochemical properties

The chemical structure of kaempferin is kaempferol 3,7-di-O-α-L-rhamnoside, meaning the kempferol molecule connects two α-L-rhamnosin residues at the hydroxyl group of the 3 and 7 hydroxyl groups via glycosidic bonds. Its molecular formula is C27H30O15, and its molecular weight is 578.5230, making it a typical glycooxyflavonoid compound. Structurally, kaempferin retains the flavonoid backbone of kaempferol, and the introduction of glycosyls significantly increases its water solubility (about 1.4906), making it more dispersible in the aqueous phase than non-glycosylated flavonoids.

In terms of physicochemical properties, the LogP value of kanaside is 0.2896, indicating strong hydrophilicity and low lipid solubility, which significantly affects its bioavailability and distribution in the body. Its topological pole surface area (TPSA) is 228.97 Ų, and a higher TPSA is usually associated with lower cell membrane permeability, especially the low blood-brain barrier permeability, suggesting limited direct action in the central nervous system. In terms of safety, kanaside did not show hERG channel inhibition, and the Ames-induced mutagenic test was negative, demonstrating a favorable safety profile.

Plant Origins and Extraction Methods

Skamarin is mainly isolated from the above-ground parts of plants such as fava bean (Vicia faba) and lotus flower (Nelumbo nucifera). As a traditional edible and medicinal plant, broad beans are rich in flavonoid glycosides in their leaves and stems; Lotus flowers are widely used in traditional Chinese medicine due to their medicinal value and rich flavonoid content.

The extraction method typically uses organic solvent extraction combined with column chromatography separation technology. Common extraction solvents include methanol, ethanol, and their aqueous solutions. Due to the hydrophilicity of kalanaside, 50%-70% ethanol aqueous solution is the ideal choice. The general withdrawal process includes:

1. Drying and crushing of plant materials;
2. Ethanol aqueous solution extraction at room temperature or reflux for several hours;
3. Concentrate the extract and remove the solvent;
4. Separation and purification are performed by silica gel column chromatography or reversed-phase C18 column chromatography;
5. Purity and structure are confirmed using high-performance liquid chromatography (HPLC) or mass spectrometry (MS).

In recent years, ultrasound-assisted extraction and microwave-assisted extraction technologies have also been applied to the efficient extraction of kamarin, improving extraction efficiency and purity.

Pharmacological activity research

The pharmacological activities of kaempaside cover a variety of biological effects, mainly including anti-inflammatory, antidiabetic, anti-tumor, antidepressant, antioxidant, and immunomodulatory effects. The specific studies are as follows:

1. Anti-inflammatory effects

Multiple in vitro and in vivo studies have confirmed that kanaside significantly alleviates inflammatory responses by inhibiting the release of inflammatory mediators (such as TNF-α, IL-6, IL-1β) and downregulating the NF-κB signaling pathway. It demonstrates good anti-inflammatory effects in models of arthritis and inflammatory bowel disease, with minimal side effects.

2. Antidiabetic effects

Kamarinin can activate insulin signaling pathways, promote glucose uptake and metabolism, and improve insulin resistance. Related studies show that kaempaside enhances phosphorylation of insulin receptor substrates (IRS) and protein kinase B (Akt), improving cellular sensitivity to insulin and lowering blood sugar levels. In addition, it also protects against diabetic complications such as diabetic nephropathy and retinopathy.

3. Antitumor effects

Sinaginine exhibits effects in various tumor cell lines by inhibiting proliferation, inducing apoptosis, and blocking the cell cycle. Its mechanism involves activating mitochondrial pathways to induce apoptosis, inhibiting the PI3K/Akt/mTOR signaling pathway, and regulating immune cell activity in the tumor microenvironment. In animal models, adjuvant kanatiside chemotherapy can enhance drug sensitivity and reduce resistance.

4. Antidepressant and neuroprotective effects

Although kaempaside has relatively low blood-brain barrier permeability, it indirectly exerts antidepressant effects by regulating peripheral immune inflammatory responses and antioxidant effects. Some studies indicate that kamaginin can regulate neurotransmitter metabolism and neuroinflammation, improving symptoms of depression.

5. Antioxidant effects

Sannal glycoside significantly enhances the body's antioxidant defense system, increases the activity of antioxidant enzymes such as superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPX), lowers reactive oxygen species (ROS) levels, and alleviates oxidative stress damage. By activating the NFE2L2/NRF2 signaling pathway, it induces downstream antioxidant enzyme expression and protects cells from oxidative damage.

6. Immune regulation

Kanaside can regulate immune cell function, balance the Th1/Th2 cell ratio, suppress excessive immune responses, and prevent the occurrence of autoimmune diseases. In animal models, it has shown potential to enhance the body's immunity and fight infections.

7. Maintaining bone density

Research shows that kaempaside regulates the activity of osteoblasts and osteoclasts, promotes bone formation, inhibits bone resorption, and helps in the prevention and treatment of osteoporosis.

Mechanism of action and molecular targets

The multiple pharmacological effects of kanaside are attributed to its regulation of multiple cellular signaling pathways and key molecules, mainly including:

1. NFE2L2/NRF2 antioxidant pathway

Kanaside activates the NFE2L2 (nuclear factor 2-related factor 2, NRF2) signaling pathway, promoting the expression of antioxidant enzymes such as SOD1, SOD2, CAT, GPX1, and HMOX1, enhancing cellular antioxidant capacity and reducing cellular damage caused by oxidative stress.

2. Insulin signaling

Kasanaside promotes phosphorylation of insulin receptors and IRS, activates the PI3K/Akt pathway, enhances the expression and transport of glucose transporter protein (GLUT4), improves insulin sensitivity, and lowers blood glucose levels.

3. Inflammatory signaling pathways

By inhibiting the NF-κB and MAPK signaling pathways, kanaside reduces the production of pro-inflammatory factors and alleviates inflammatory responses.

4. Apoptosis regulation

Kasanaside regulates the expression of Bcl-2 family proteins, promotes mitochondria-dependent apoptosis, and inhibits tumor cell proliferation.

5. Immune regulation

Regulates the proportion of T cell subsets and cytokine secretion to maintain immune homeostasis.

Druggability evaluation and pharmacokinetics

The druggability evaluation of kasanaside shows certain advantages and challenges:

• Molecular weight and polarity: The molecular weight is 578.5230, which is relatively large and has a high TPSA value, suggesting that oral absorption may be limited and the cell membrane permeability is poor.
• Water solubility: Good water solubility, which is beneficial for formulation development and in vivo distribution.
• Lipid solubility (LogP): 0.2896, indicating strong hydrophilicity and possibly affecting lipid membrane penetration.
• Blood-brain barrier permeability: low, limiting its direct effect in the central nervous system.
• Safety: No hERG channel suppression, Ames test negative, indicating good safety.
• Pharmacokinetics: Currently, there is limited research on in vivo metabolism and bioavailability of sinalycoside. Preliminary data suggest that it may be partially hydrolyzed by gut microbiota in the intestine, releasing kaempferol, which has good biological activity and absorption. Further research is needed in the future on its metabolic pathways, half-life, and tissue distribution.

Prospects and outlooks for clinical applications

Given the significant pharmacological activity of kaempnaside in various disease models, its clinical development potential is enormous. Especially in fields such as diabetes and its complications, chronic inflammatory diseases, adjuvant therapy for tumors, and osteoporosis, sinaside is expected to become a new natural medicine or functional health supplement ingredient.

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

• Optimizing formulations to improve oral bioavailability;
• Clarify pharmacokinetic characteristics and activity of metabolites;
• Conduct clinical safety and efficacy evaluations;
• Explore combined applications with existing drugs to achieve synergistic effects.

Additionally, due to its low blood-brain barrier permeability, the application of kaempaside in central nervous system diseases may need to be improved through structural modification or nanocarrier technology.

Conclusion

As a multifunctional natural flavonoid compound, kanaside demonstrates the potential as a candidate drug for treating various diseases due to its broad pharmacological activity and good safety profile. Its mechanisms of action in anti-inflammation, antidiabetic, antitumor, and antioxidant properties are becoming clearer, providing abundant examples for pharmacological research of natural products. In the future, through in-depth pharmacokinetic research, formulation optimization, and clinical validation, kamarinin is expected to translate from laboratory research to clinical application, promoting the application and development of natural products in modern medicine.