Product name: 2''-O-beta-L-galactopyranosylorientin
Synonym name: Orientin-2''-O-β-L-galactoside
Catalogue No.: BP0035
Cas No.: 861691-37-4
Formula: C₂₇H₃₀O₁₆
Mol Weight: 610.521
Botanical Source: Lophatherum gracile Brongn.
Physical Description:
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
Inquire for bulk scale.




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HPLC of 2"-O-beta-L-galactopyranosylorientin

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

Introduction/Overview

Brassinoside-2''-O-β-L-galactopyranosylorientin (hereinafter referred to as "Cyvicin-2''-O-β-L-galactoside") is a flavonoid glycoside derived from natural plants with significant biological activity and potential medicinal value. With the continuous development of natural product pharmacology, vitronin-2''-O-β-L-galactosyside has become a research hotspot in recent years due to its unique chemical structure and good safety. This paper aims to systematically review the chemical structure and physicochemical properties of this compound, plant origin and extraction methods, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects, aiming to provide a theoretical basis and research direction for further drug development and clinical translation.

Chemical structure and physicochemical properties

Brassin-2''-O-β-L-galactosiside has a molecular formula of C_27H_30O_16 and a molecular weight of 626.5, making it a glycoside derivative of the flavonoid glycoside orientin. Its structural feature is that the 2'' hydroxyl group on the orientin molecule is connected to a galactose unit by β-L-galactoside bonds, forming a disaccharide structure. This structure endows it with strong hydrophilicity, with a LogP value of -2.5, indicating low hydrophobicity and good water solubility. Its topological pole surface area (TPSA) reaches 298.5 Ų, with 16 hydrogen bond acceptors, exhibiting strong polarity and multi-hydroxyl structure, facilitating multi-point binding with biological macromolecules.

In terms of physicochemical properties, cyperidin-2''-O-β-L-galactosoyside exhibits good chemical stability, especially stable under acidic and neutral conditions, but may undergo hydrolysis in strongly alkaline environments. Its UV-visible spectrum shows typical flavonoid absorption peaks, facilitating qualitative and quantitative analysis. Mass spectrometry and nuclear magnetic resonance (NMR) technologies have been widely used for structural identification and purity detection.

Plant Origins and Extraction Methods

Brassin-2''-O-β-L-galactosinoside is mainly found in certain traditional Chinese medicinal materials and wild plants, especially in medicinal values such as grasses and some legumes, with higher content. Common plant sources include water shield (Setaria italica) and its related species; some medicinal plants such as kudzu root and cassia seeds have also been reported.

The extraction process typically uses water or water-alcohol mixed solvents for extraction combined with ultrasonic-assisted extraction or hot reflux extraction to increase yield. The extract was purified by multi-stage solvent separation, column chromatography (such as silica gel column, C18 reversed-phase column), and high-performance liquid chromatography (HPLC), ultimately yielding high-purity vitriole-2''-O-β-L-galactoside. In recent years, supercritical CO_2 extraction and membrane separation technologies have also been attempted for efficient extraction and purification of this compound, improving extraction efficiency and purity.

Pharmacological activity research

Brassicin-2''-O-β-L-galactosinoside exhibits broad pharmacological activity across various in vitro and in vivo models, covering antioxidant, anti-inflammatory, antitumor, neuroprotection, and immunomodulatory aspects.

1. Antioxidant activity
   This compound has significant free radical scavenging ability, effectively inhibiting oxidative reactions of free radicals such as DPPH and ABTS, thereby reducing cellular oxidative damage. Its polyhydroxyl structure provides excellent electron donor capacity, enhancing the antioxidant defense system.

2. Anti-inflammatory effects
   Research shows that vitrin-2''-O-β-L-galactosinoside can inhibit the release of inflammatory mediators such as TNF-α, IL-6, and IL-1β, reducing inflammatory responses. It demonstrated significant anti-inflammatory effects in mouse inflammation models, suggesting its potential application value in inflammatory diseases.

3. Antitumor activity
   In vitro cell experiments have shown that this compound inhibits proliferation and induces apoptosis in various tumor cell lines (such as liver cancer, breast cancer, colon cancer). Its antitumor mechanism involves cell cycle blockade, mitochondrial pathway activation, and inhibition of tumor-related signaling pathways.

4. Neuroprotective effects
   Although vitrin-2''-O-β-L-galactinoside does not easily cross the blood-brain barrier, in neuron models, it alleviates nerve damage through antioxidant and anti-inflammatory mechanisms, offering potential neuroprotective effects.

5. Immune regulation
   This compound can regulate immune cell function, promote macrophage phagocytic activity, regulate the balance of T cell subsets, and enhance the body's immune defense capabilities.

Mechanism of action and molecular targets

The bioactivity of vitrin-2''-O-β-L-galactosoyside mainly depends on its interactions with various molecular targets. Research reveals that its main mechanisms of action include:

1. Antioxidant mechanism
   By directly removing reactive oxygen species (ROS) and active nitrogen (RNS), it inhibits lipid peroxidation and protects cell membranes and DNA from oxidative damage. It simultaneously activates the Nrf2/ARE signaling pathway, promoting the expression of endogenous antioxidant enzymes (such as SOD, CAT, GPx).

2. Anti-inflammatory mechanism
   Inhibits activation of the NF-κB signaling pathway, reduces transcription and release of pro-inflammatory factors, and lowers inflammatory responses. Brassicin-2''-O-β-L-galactosoyside can also regulate the MAPK pathway, inhibiting phosphorylation of p38, JNK, and ERK.

3. Antitumor mechanism
   Cell cycle blockade and apoptosis induction are achieved by regulating cyclins and apoptosis-related proteins (such as Bcl-2, Bax, Caspase-3). It can also inhibit the PI3K/Akt/mTOR signaling pathway, blocking tumor cell proliferation and migration.

4. Immune regulatory mechanisms
   Regulates the secretion of immune cytokines, promotes macrophage polarization toward M1 type, and enhances anti-infection ability. Maintains immune homeostasis by regulating the proportion of T cell subsets.

In summary, the synergistic effects of cubicin-2''-O-β-L-galactose through multi-target and multi-pathway synergistic effects are exerted.

Druggability evaluation and pharmacokinetics

The druggability parameters of Cyperidin-2''-O-β-L-galactosinoside indicate good safety and tolerability. Its LogP value was -2.5, indicating good water solubility but low lipid solubility, which may limit its oral bioavailability. The TPSA value reached as high as 298.5 Ų, far exceeding the ideal range for general oral drugs, indicating weak passive diffusion ability through cell membranes.

Toxicological evaluation showed that this compound had no significant hepatotoxicity, cardiotoxicity, or hERG channel inhibitory effects, and the Ames-induced mutagenic test was negative, indicating a relatively high safety profile. Additionally, the poor blood-brain barrier penetration limits its application in central nervous system diseases, but also reduces the risk of central toxic side effects.

Pharmacokinetic studies show that caturin-2''-O-β-L-galactosinoside is absorbed slowly orally, has a moderate plasma half-life, and is mainly excreted by the kidneys and bile. Its metabolic pathway involves glycoside hydrolysis and corresponding flavonoid glycolyte metabolism, with metabolites also having certain biological activity.

To improve its pharmacokinetic properties, researchers have tried strategies such as nanocarriers, liposomal encapsulation, and structural modification to enhance its bioavailability and targeting.

Prospects and outlooks for clinical applications

Brassicin-2''-O-β-L-galactose, with its multi-target and multifunctional pharmacological activity, demonstrates broad clinical application potential in anti-inflammation, anti-tumor, antioxidant, and immunomodulatory fields. It has promising application prospects especially in adjunctive therapy for chronic inflammatory diseases, autoimmune diseases, and certain tumors.

However, this compound is still in the basic research and early pharmacological evaluation stages, lacking systematic clinical trial data. Future research should focus on:

1. Pharmacokinetics and dosage form optimization
   By improving administration methods and formulation design, bioavailability and targeting can be enhanced, overcoming the limitations of poor blood-brain barrier penetration.

2. In-depth exploration of mechanisms
   Using modern molecular biology and systems biology techniques, it further clarifies its molecular targets and signaling pathways, revealing the molecular basis behind its pleiotropy.

3. Safety and toxicology research
   Conduct long-term toxicological and pharmacodynamic studies to ensure the safety of clinical application.

4. Preclinical and clinical trials
   Promote the entry of Brassicin-2''-O-β-L-galactosinoside into preclinical research, gradually conduct clinical trials, and verify its efficacy and safety.

In addition, combining modern drug design concepts, structural modification and derivative development of comicamide-2''-O-β-L-galactosinoside will also provide new ideas for its medicinal chemistry optimization.

Conclusion

Brassinoside-2''-O-β-L-galactosinoside is a natural flavonoid glycoside with multiple biological activities, demonstrating good pharmacological potential and safety. Its unique chemical structure gives it multi-target capabilities, giving it broad application prospects in antioxidant, anti-inflammatory, anti-tumor, and immunomodulatory fields. Although challenges remain in bioavailability and pharmacokinetics, with the support of modern drug development technologies, vitronin-2''-O-β-L-galactosinoside is expected to become an important candidate for novel natural drugs. In the future, systematic mechanism research and clinical validation will be key to promoting their translation into clinical applications. The field of natural product pharmacology should continue to pay attention to and deepen research on this compound, aiming to achieve its widespread application in disease prevention and treatment.