Product name: Glucoraphenin
Synonym name:
Catalogue No.: BP4103
Cas No.: 28463-24-3
Formula: C₁₂H₂₁NO₁₀S₃
Mol Weight: 435.477
Botanical Source:
Physical Description:
Type of Compound: Aliphatics

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.

For Reference Standard and R&D, Not for Human Use Directly.

HPLC of Glucoraphenin

HNMR of Glucoraphenin

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

Introduction/Overview

Glucoraphenin, CAS number 28463-24-3, is a glucoside compound naturally occurring in cruciferous plants. As a secondary metabolite unique to radish (Raphanus sativus) and its related species, racoside has attracted widespread attention in recent years due to its potential bioactivity, especially its significant role in anti-inflammatory fields. Inflammatory responses are the pathological basis of various chronic diseases, including autoimmune diseases, metabolic syndromes, neurodegenerative diseases, and tumors. Finding natural anti-inflammatory active ingredients with low toxicity and side effects has become an important direction for drug development. With its unique chemical structure and good safety, racoside demonstrates the ability to regulate various inflammation-related signaling pathways, making it a hot topic in natural product pharmacology research.

This paper will systematically review the chemical structure and physicochemical properties of rafadoside, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics. It will also explore its clinical application prospects in conjunction with existing research, aiming to provide theoretical basis and research directions for subsequent drug development and clinical translation.

Chemical structure and physicochemical properties

Rafasinoside belongs to the glucosinolate family, with its basic structure consisting of a glucosinoside core and a side chain. The molecular formula of racraside is C15H26NO10S3, with a molecular weight of 435.4980. Its structural features include a glucose residue connected to a sulfur-containing side chain via a sulfur bond, giving it specific biological activity.

In terms of physicochemical properties, the LogP value of racoside is -1.3134, indicating strong hydrophilicity. Its water solubility is 40.7128 (usually mg/mL or relevant standards; specific units must be confirmed in reference literature). The polar surface area (TPSA) is 189.1700 Ų, indicating high polarity that may affect cell membrane permeability and bioavailability. The blood-brain barrier has low permeability, suggesting that racoside has limited distribution in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test value was 0.9, nearly non-mutagenic, indicating a low genotoxicity risk.

These physicochemical parameters indicate that lafuroside has good safety and certain drug compatibility, but its high polarity and low blood-brain barrier permeability may limit some of its pharmacological effects, requiring optimization through formulation techniques or structural modifications.

Plant Origins and Extraction Methods

Radish glycosides are mainly found in cruciferous plants, especially abundant in radish (Raphanus sativus) and its wild relatives. Its content is significantly influenced by plant variety, growing environment, harvest time, and storage conditions. Besides radish, Chinese broccoli (Brassica oleracea var. Alboglabra), mustard greens (Brassica juncea), and related plants.

Traditional extraction methods mainly combine water extraction with alcohol extraction, supplemented by solid-phase extraction or column chromatography purification. The specific steps usually include:

1. Raw material pretreatment: Crush fresh or dried plant tissue to increase surface area.
2. Water extraction: Olafasin is extracted using warm or hot water; due to its strong hydrophilicity, water extraction efficiency is relatively high.
3. Ethanol precipitation or alcohol extraction: removing polysaccharides and other impurities.
4. Solid-phase extraction or ion exchange column purification: Separation utilizes the polarity and ionic properties of racoside.
5. High-performance liquid chromatography (HPLC) or mass spectrometry (MS) for quantitative detection.

In recent years, modern technologies such as ultrasound-assisted extraction and microwave-assisted extraction have been applied to the extraction of racoside, significantly improving extraction efficiency and purity, while reducing solvent usage, in line with the concept of green chemistry.

Pharmacological activity research

Research on the pharmacological activity of racoside mainly focuses on its anti-inflammatory effects, but also involves antioxidant, anti-tumor, and immune regulation. Its anti-inflammatory activity has been validated in various in vitro cell and animal models.

Anti-inflammatory activity

Numerous studies have shown that racoside can significantly inhibit the release of inflammatory mediators and the activation of inflammatory signaling pathways. For example, in macrophage and epithelial cell models, after lafuroside treatment, the expression of pro-inflammatory cytokines such as IL-6 and TNF-α was significantly reduced, while the activity of inflammation-related enzymes like PTGS2 (COX-2) and NOS2 (iNOS) was suppressed. In addition, rafaside can reduce tissue damage caused by inflammation, demonstrating good tissue protective effects.

Other pharmacological effects

Besides anti-inflammatory, racoside has certain antioxidant properties that can eliminate free radicals and reduce cellular damage caused by oxidative stress. Some studies report its proliferation-inhibiting effect on tumor cells, possibly related to its regulation of apoptosis and signaling pathways. Additionally, racolaside has shown potential to modulate immune responses, possibly by affecting the activation status of immune cells and cytokine networks.

Mechanism of action and molecular targets

The anti-inflammatory mechanism of racoside involves multiple signaling pathways and key molecular targets, mainly including:

• IL-6 (interleukin-6): Racolaside can downregulate IL-6 expression, inhibit its mediated pro-inflammatory signaling, and reduce inflammatory responses.
• STAT3 (Signal Transduction and Transcription Activator 3): As a key transcription factor in the IL-6 signaling pathway, inhibition of STAT3 helps block the transcription of inflammatory genes.
• CASP1 (caspase 1): Involved in the activation of inflammasomes, racoside reduces the release of inflammatory mediators such as IL-1β by inhibiting CASP1 activity.
• TRPV1 (transient receptor potential vanillate receptor 1) and TRPA1 (transient receptor potential vanillate receptor-associated 1): These ion channels play important roles in inflammation and pain transmission, and racoside modulates them to potentially alleviate inflammation-related pain symptoms.
• PTGS1 (COX-1) and PTGS2 (COX-2): Laceraside selectively inhibits PTGS2, reduces prostaglandin synthesis, and lowers inflammatory responses.
• TNF (tumor necrosis factor): As a key pro-inflammatory factor, racoside inhibits TNF expression and reduces inflammatory cascades.
• NOS2 (induced nitric oxide synthase): Racoside inhibits NOS2 expression and reduces inflammation-related nitric oxide production.
• NFKB1 (nuclear factor κB): As a core transcription factor for inflammatory signals, racoside inhibits inflammatory gene expression by blocking NF-κB activation.

In summary, laifoside regulates multiple stages of inflammatory response through synergistic action across multiple targets and pathways, demonstrating its potential as a natural anti-inflammatory agent.

Druggability evaluation and pharmacokinetics

The druggability of lafasin is evaluated based on its physicochemical properties, toxicological data, and in vivo pharmacokinetic characteristics.

Physicochemical and safety evaluations

The LogP value of laparaside was -1.3134, indicating strong hydrophilicity, which may affect oral absorption and cell membrane penetration. A high TPSA value (189.17 Ų) further supports its high polarity, which may limit its oral bioavailability. The low permeability of the blood-brain barrier suggests it is difficult to enter the central nervous system, making it suitable for treating peripheral inflammatory diseases. hERG channel inhibition was negative, and Ames tests were nearly negative, indicating low cardiotoxicity and genotoxicity risks and good safety.

Pharmacokinetic characteristics

Currently, pharmacokinetic research on racoside is relatively limited. Previous studies have shown that raplavin is mainly absorbed through the intestines and then enters the bloodstream, with metabolic pathways possibly involving the hydrolysis and conversion of glucosinolates. Its high hydrophilicity and polarity may lead to faster kidney clearance and limited tissue distribution. Low blood-brain barrier permeability limits central function. In the future, systematic in vivo metabolic kinetics studies are needed, including detailed analyses of absorption, distribution, metabolism, and excretion (ADME) processes to guide dosage form development and clinical application.

Prospects and outlooks for clinical applications

As a natural glucosinolate compound, racoside has significant anti-inflammatory activity and good safety, demonstrating broad clinical application potential. Its multi-target regulation of inflammatory signaling pathways gives it potential advantages in treating chronic inflammatory diseases, autoimmune diseases, and related pain management.

The key to future clinical applications lies in:

1. Dosage Form Optimization: To address the high polarity and low bioavailability of lafaroside, develop nanoformulations, liposome-loaded formulations, or other sustained-release formulations to improve oral absorption and in vivo stability.
2. Combination therapy strategy: combine other anti-inflammatory drugs or natural products to achieve synergistic effects, reduce single drug dosage, and minimize side effects.
3. Clinical trial validation: Conduct systematic preclinical safety evaluations and phase I/II clinical trials to clarify effective dose ranges and therapeutic indications.
4. Structural modification and derivative development: Chemical modification improves pharmacokinetic properties and develops racoside derivatives to enhance their efficacy and targeting.

In addition, the potential of laperiside in anti-tumor, antioxidant, and immunomodulatory areas is worth further exploration, providing new ideas for multi-field drug development.

Conclusion

Radish glycosides, a natural glucoside derived from cruciferous plants, have become an important subject of natural product pharmacological research due to their unique chemical structure and significant anti-inflammatory activity. Its multi-target regulation of inflammatory signaling pathways provides a theoretical basis for the development of novel anti-inflammatory drugs. Although research on its pharmacokinetics and clinical applications is still in its early stages, its good safety profile and diverse bioactivity suggest broad application prospects. In the future, through dosage form optimization, structural modification, and clinical validation, racoside is expected to become an important natural drug candidate for treating inflammation-related diseases.