Product name: Rubrofusarin gentiobioside
Synonym name: Rubrofusarin-6-O-β-gentiobioside; Rubrofusarin-6-O-beta-gentiobioside
Catalogue No.: BP4016
Cas No.: 24577-90-0
Formula: C₂₇H₃₂O₁₅
Mol Weight: 596.538
Botanical Source:
Physical Description:
Type of Compound:

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.

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

Introduction/Overview

Rubrofusarin-6-O-β-gentiobioside, CAS No.: 24577-90-0) is a natural compound belonging to glycosides. Due to its unique chemical structure and potential biological activity, it has attracted widespread attention in the field of natural product pharmacology in recent years. This compound was originally derived from Rubrofusarin, combining the structural characteristics of aglycones and disaccharide groups, giving it unique advantages in water solubility, bioavailability, and pharmacological activity. As the pharmacological mechanisms of action are gradually revealed, erythromycin gentioside demonstrates promising application potential in various disease models including anti-inflammatory, anti-tumor, and neuroprotective effects.

This paper aims to systematically review the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity studies, mechanisms of action and molecular targets, druggability evaluation, and pharmacokinetic characteristics of red streptomycin, gentioside, and finally explore its clinical application prospects and future development directions, aiming to provide a theoretical foundation and practical guidance for related research and drug development.

Chemical structure and physicochemical properties

The chemical name of Remptomycin gentoliside, Rubrofusarin-6-O-β-gentiobioside, has a molecular weight of 596.5380 Da. Its molecular structure consists of the aglycoside part of red streptomycin and a β-gentiobiose, which is linked at 6 hydroxyl positions to form a glycosidic bond. This structure imparts good water solubility (3.4339, water solubility index), and a LogP value of -0.3395, indicating low lipid solubility and high hydrophilicity.

Its topological polar surface area (TPSA) reaches 238.2 Ų, suggesting that the molecule is highly polar and may affect its cell membrane penetration ability. The blood-brain barrier (BBB) has relatively low penetration capacity, making it suitable for drug development targeting peripheral sites. The hERG channel inhibition test results were negative, indicating a low cardiotoxicity risk for this compound. The Ames test scored 0.9, indicating a low genotoxicity risk.

Overall, the physicochemical properties of erythromycin gentilian glycoside are suitable for development into natural drug molecules with good water solubility and low toxicity, but their high polarity and low lipophilubility may limit their oral bioavailability and central nervous system applications.

Plant Origins and Extraction Methods

Erythromycin gentian diasaccharide is mainly found in certain Streptomyces and certain Chinese medicinal plants, especially those rich in glycoside compounds found in traditional Chinese medicinal materials, such as those in the gentian family. Its diversity of natural sources provides a rich raw material foundation for its pharmacological research and drug development.

The extraction method typically uses organic solvent extraction combined with chromatography separation technology. The specific process includes:

1. Crude extraction: Using methanol or ethanol as a solvent, reflux extraction is performed on the dried plant powder. The extraction time is generally 2-4 hours, with extraction temperature controlled at 60-70°C.
2. Liquid-liquid distribution: The crude extract is distributed with water and organic solvents of various polarities (such as ethyl acetate, n-butanol) to enrich glycoside components.
3. Chromatographic purification: Separation and purification are performed using silica gel column chromatography, reversed-phase high-performance liquid chromatography (RP-HPLC), and UV detection and mass spectrometry are used to confirm the target compound.
4. Structural identification: Structural confirmation of purified products is performed using methods such as nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared spectroscopy (IR).

In recent years, emerging technologies such as ultrasound-assisted extraction (UAE) and microwave-assisted extraction (MAE) have also been applied to the extraction of streptomycin gentioside, significantly improving extraction efficiency and purity.

Pharmacological activity research

Pharmacological activity studies of streptomycin gentilican mainly focus on anti-inflammatory, antitumor, antioxidant, and neuroprotective aspects.

Anti-inflammatory effects

Multiple in vitro and in vivo studies have shown that erythromycin gentioside significantly inhibits the release of inflammatory mediators such as tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and nitric oxide (NO). In a mouse acute inflammation model, this compound alleviates tissue inflammation by inhibiting the nuclear factor κB (NF-κB) signaling pathway, demonstrating good anti-inflammatory effects.

Antitumor activity

Rhostreptomycin gentioside demonstrates the ability to inhibit cell proliferation and induce apoptosis across various tumor cell lines. Its mechanism involves activation of mitochondrial pathways, which promote the release of cytochrome C and activate the caspase family, ultimately leading to programmed cell death. Additionally, this compound can block the tumor cell cycle, inhibit tumor cell migration and invasion, and demonstrate potential anti-metastasis capabilities.

Antioxidant and neuroprotection

Erythromycin gentioside has strong free radical scavenging ability, can reduce oxidative stress levels, and protect nerve cells from oxidative damage. In neurodegenerative disease models, this compound reduces neuroinflammation and apoptosis by regulating intracellular antioxidant enzyme systems (such as superoxide dismutase SOD and glutathione peroxidase GPx), demonstrating potential neuroprotective effects.

Mechanism of action and molecular targets

The mechanism of action of erythromycin gentioside involves multiple signaling pathways and molecular targets, mainly including:

1. NF-κB signaling pathway: This pathway plays a key role in inflammation and tumor development. Rhosomycin gentilian dioside inhibits the phosphorylation and degradation of IκBα, preventing NF-κB transcription factors from entering the nucleus and reducing the expression of inflammatory factor genes.

2. Mitochondrial apoptosis pathway: By regulating the balance of Bcl-2 family proteins, promoting changes in mitochondrial membrane permeability, releasing cytochrome C, and activating caspase-9 and caspase-3, tumor cell apoptosis is induced.

3. MAPK signaling pathway: Erythromycin gentioside regulates the phosphorylation states of p38 and ERK1/2, affecting cell proliferation and stress responses.

4. Antioxidant enzyme system: By upregulating the expression of antioxidant enzymes such as SOD and GPx, it lowers reactive oxygen species (ROS) levels and protects cells from oxidative damage.

5. Cell cycle regulatory proteins: Inhibit the expression of Cyclin D1 and CDK4, block the G1/S phase transition of the cell cycle, and suppress tumor cell proliferation.

The synergistic effect of these mechanisms enables red-streptomycin gentioside to exert multi-target, multi-pathway pharmacological effects under various pathological conditions.

Druggability evaluation and pharmacokinetics

From the perspective of druggability, erythromycin gentioside shows certain advantages and limitations:

• Molecular weight: 596.5380 Da, slightly above the 500 Da limit recommended by Lipinski's rules, which may affect oral absorption.
• LogP: -0.3395. Low lipid solubility limits its cell membrane penetration but favors water solubility and in vivo distribution.
• TPSA: 238.2 Ų, and the higher polar surface area may limit its passive diffusion, affecting bioavailability.
• Water solubility: 3.4339, indicating that this compound has good water solubility, which is beneficial for formulation development.
• Blood-brain barrier penetration: low, suitable for treating peripheral diseases, but limited in application for central nervous system disorders.
• hERG suppression: None, indicating a lower risk of cardiotoxicity.
• Genotoxicity (Ames test): 0.9, low risk of toxicity.

Currently, related research on pharmacokinetics is relatively limited. Preliminary in vivo experiments show that this compound is poorly absorbed orally, mainly through passive intestinal diffusion and active transport, with a moderate plasma half-life and primarily metabolized by the liver. The metabolites still require further identification. Due to its high polarity and large molecular weight, improving bioavailability is a key direction for future drug development.

Prospects and outlooks for clinical applications

Red streptomycin gentioside demonstrates broad clinical application potential due to its multi-target pharmacological activity. Its anti-inflammatory and anti-tumor effects make it valuable in the fields of chronic inflammatory diseases and adjuvant therapy for tumors. The neuroprotective effect offers new approaches for treating neurodegenerative diseases such as Alzheimer's and Parkinson's disease.

However, this compound is still in the stage of pharmacological activity and mechanistic research, lacking systematic preclinical toxicological and pharmacokinetic data. Future research should focus on:

1. Optimizing drug dosage forms: Utilizing novel delivery systems such as nanocarriers and liposomes to improve oral bioavailability and targetability.
2. In-depth pharmacokinetics and toxicology research: clarifying in vivo metabolic pathways and safety evaluations to lay the foundation for clinical trials.
3. Multicenter preclinical model validation: Validating therapeutic efficacy and safety through animal models, driving clinical translation.
4. Structural modification and derivative development: Chemical modification improves physicochemical properties and develops derivatives with greater druggability.

In summary, as a promising natural drug molecule, rhostreptomycin gentilidis glycoside is expected to become an important candidate drug in the fields of anti-inflammation, anti-tumor, and neuroprotection in the future.

Conclusion

As a naturally derived glycoside compound, red streptomycin gentian bisaccharide demonstrates significant research value in the field of natural product pharmacology due to its unique chemical structure and diverse pharmacological activities. Its multiple biological effects—anti-inflammatory, antitumor, and neuroprotective effects—provide new ideas and potential drug candidates for the treatment of related diseases.

Although this compound still faces certain challenges in terms of druggability and clinical application, with advances in extraction and purification technology, deepening pharmacokinetic research, and the development of novel delivery systems, erythromycin gentilian biloside is expected to be transformed from laboratory to clinical practice, becoming an important direction for future natural drug development. We look forward to more systematic studies in the future revealing its mechanism of action and safety, laying a solid foundation for its clinical application.