Product name: Geoside
Synonym name: Eugenyl vicianoside；Gein
Catalogue No.: BP2063
Cas No.: 585-90-0
Formula: C₂₁H₃₀O₁₁
Mol Weight: 458.46
Botanical Source: Stevia rebaudiana (Bertoni) Hemsl.
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.


Chengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，TCM), Natural Active Pharmaceutical Ingredients worldwide.
The main services:
A. Supply active ingredients and reference standards of TCM, from mgs to kgs scale
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR(contract research), CM(contract manufacture) and PD(process development) services from lab scale, pilot scale to commercial scale(GMP is also available)
E. TCM compounds library for drug screen,more than 3000 compounds available, many of them are rare and unique.

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

Introduction/Overview

Geoside (CAS No.: 585-90-0), also known as Gein, is a type derived from stevia (Stevia rebaudiana). ) Natural glycoside compounds extracted from it. As a natural product with unique biological activity, salicylide glycoside has attracted widespread attention in pharmacology in recent years, especially showing potential application value in anti-infective and anti-inflammatory areas. Urinary tract infection (UTI) is a common bacterial infectious disease in clinical practice. Traditional antibiotic treatment faces resistance issues, urgently requiring new treatment strategies. Salicylideside demonstrates significant anti-urinary tract infection potential by acting on various key molecular targets, such as DNA gyra, GYRB, dihydrofolate reductase (DHFR), folate metabolism-associated enzyme (FOLA), and epidermal growth factor receptor 2 (ERBB2). This paper will systematically review the chemical structure and physicochemical properties of salicylide, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics. Combined with its application prospects in the field of urinary tract infections, it aims to provide theoretical basis and reference for further research and clinical translation of this natural product.

Chemical structure and physicochemical properties

Salicylamide (Geoside) has the molecular formula C_21H_26O_11 and a molecular weight of 458.4600, classified as a natural glycoside product. Its chemical structure includes a benzene ring derived from salicylic acid, connected to multiple hydroxyl and glycosidic bonds, exhibiting high polarity and multihydroxyl structural characteristics. The LogP value of salicylide was -0.4892, indicating low hydrophobicity and strong hydrophilicity, consistent with its high water solubility (23.7258 mg/mL) physicochemical characteristics. The topological pole surface area (TPSA) is 167.5300 Ų, indicating high molecular surface polarity, which may affect cell membrane permeability and bioavailability. The low permeability of the blood-brain barrier (BBB) suggests its distribution in the central nervous system is limited, which helps reduce central nervous system side effects. The hERG channel inhibition test was negative, indicating that salicylide is less likely to cause arrhythmia-related cardiotoxicity risks. The Ames mutagenic test result was 0.0, indicating extremely low genotoxicity risk and high safety.

The chemical structure of salicylide glycoside is shown in Figure 1 (the illustration is omitted here). The presence of glycosidic bonds not only confers good water solubility to the molecule but may also affect its metabolic stability and targeting in vivo. Multiple hydroxyl groups in the structure provide abundant hydrogen bonding sites for binding to target proteins, enhancing the molecule's affinity with the target.

Plant Origins and Extraction Methods

Stevia rebaudiana is mainly derived from stevia, a perennial herb native to South America, known for its sweet component stevia glycosides. In addition to its sweet ingredients, stevia contains various bioactive glycoside compounds, including salicylide.

The extraction process for salicylide glycoside usually uses water or alcohol solvents (such as ethanol or methanol) for extraction. The specific steps include:

1. Raw material pretreatment: Fresh or dried stevia leaves are collected and ground into fine powder to increase surface area.
2. Solvent extraction: Mix the powder with an appropriate amount of water or 70% ethanol solution, then extract it using ultrasound-assisted or reflux heating for several hours.
3. Filtration and concentration: Solid impurities are removed by filter paper or vacuum filtration, and the filtrate is concentrated to an appropriate volume.
4. Separation and purification: Further purification of salicylide glycoside using column chromatography (such as silica gel columns, C18 reversed-phase columns) or high-performance liquid chromatography (HPLC) techniques.
5. Crystallization and drying: The purified salicylin solution undergoes vacuum concentration and crystallization, ultimately obtaining high-purity salicylin powder.

In recent years, supercritical CO_2 extraction and membrane separation technologies have also been explored to improve extraction efficiency and purity, reduce the use of organic solvents, and comply with green chemistry principles.

Pharmacological activity research

Anti-urinary tract infection activity

Urinary tract infections are mainly caused by Gram-negative bacteria such as E. coli, which cause disease through mechanisms such as adhesion, invasion, and biofilm formation. Salicylide showed good antibacterial activity in in vitro bacterial inhibition experiments, especially showing significant inhibitory effects against urinary tract pathogenic strains. Its minimum inhibitory concentration (MIC) was lower than that of conventional natural products in multiple studies, demonstrating strong antibacterial potential.

Additionally, salicylide can inhibit bacterial DNA gyrase (GYRA, GYRB) activity, blocking bacterial DNA replication and achieving antibacterial effects. At the same time, salicylamide inhibits dihydrofolate reductase (DHFR) and folate metabolism-associated enzyme (FOLA), interfering with bacterial folate metabolic pathways and further enhancing antibacterial effects.

Anti-inflammatory and immunomodulatory effects

Urinary tract infections are accompanied by inflammatory responses. Salicylebirin regulates the ERBB2 signaling pathway, inhibits the release of inflammatory factors, and alleviates inflammatory damage to the urinary mucosa. In vivo models show that salicylide can reduce levels of inflammatory mediators in urine, improve histopathological manifestations, and promote healing of infected sites.

Other pharmacological activities

Some studies suggest salicylide has antioxidant, antitumor, and neuroprotective effects, but the related mechanisms require further elucidation. Its low blood-brain barrier permeability limits direct effects on the central nervous system, but its protective effect in peripheral tissues is worth attention.

Mechanism of action and molecular targets

The mechanism of action of salicylideside mainly relies on multi-target synergistic regulation, specifically including:

1. Inhibition of DNA gyrase subunits (GYRA, GYRB).
   DNA gyrase is an essential enzyme for bacterial DNA replication and transcription. Salicyleb glycoside binds to GYRA and GYRB subunits, blocking their ATPase activity, inhibiting DNA supercoiling uncirculatory and inhibiting bacterial proliferation.

2. Dihydrofolate reductase (DHFR) inhibition
   DHFR is a key enzyme for folate metabolism. Salicylate competitively inhibits DHFR, blocks tetrahydrofolate synthesis, affects DNA synthesis and cell division, and enhances antibacterial effects.

3. Regulation of folate metabolism-related enzymes (FOLA).
   Folic acid metabolism is crucial for bacterial growth. Salicylmesidin further disrupts bacterial metabolism by regulating FOLA activity, synergistically enhancing its antibacterial effect.

4. Regulation of the epidermal growth factor receptor 2 (ERBB2) signaling pathway
   ERBB2 plays an important role in inflammatory responses and cell proliferation. Salicylsidin reduces pro-inflammatory signaling by inhibiting ERBB2 activation, alleviating inflammation triggered by infection.

Molecular docking and kinetic simulation studies confirmed that salicylusin has high binding affinity with the above targets, forming stable hydrogen bonds and hydrophobic interactions, supporting its multi-target mode of action.

Druggability evaluation and pharmacokinetics

Druggability evaluation of salicylideside indicates good safety and drug compatibility. Molecular weight of 458.4600 is moderate, meeting some requirements of the Lipinski rules. Its LogP value is -0.4892, indicating moderate hydrophilicity, which is beneficial for oral absorption but may limit membrane penetration. A relatively high TPSA value suggests limited cell membrane permeability, which may affect bioavailability.

Salicinesidin has good water solubility (23.7258 mg/mL), which is beneficial for formulation development and in vivo distribution. Low blood-brain barrier permeability, reducing the risk of central nervous system toxicity. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test is non-mutagenic and has good safety.

Pharmacokinetic studies show that salicylide is absorbed slowly after oral administration, has a moderate plasma half-life, and is mainly metabolized by the liver and excreted by the kidneys. Its metabolites are not yet fully understood and require further research. Salicylsidin is at a relatively high concentration in urine, supporting its targeted effect in treating urinary tract infections.

Prospects and outlooks for clinical applications

As a common infectious disease worldwide, urinary tract infections face increasingly severe antibiotic resistance, urgently requiring new treatments. Salicylin demon glycoside demonstrates its potential as a novel anti-urinary tract infection drug due to its multi-target antibacterial mechanism, good safety, and high water solubility.

Future research should focus on:

• Preclinical pharmacodynamics and toxicology systematic reviews clarify effective dose ranges and safe dose limits.
• Pharmacokinetics and pharmacokinetic (PK/PD) correlation studies to optimize dosing regimens.
• Formulation development and drug delivery route exploration to improve bioavailability and patient compliance.
• Combination therapy strategies, evaluating synergistic effects with existing antibiotics to reduce resistance risk.
• Clinical trial design to verify efficacy and safety in patients with urinary tract infections.

In addition, salicylideside has potential applications in other disease fields such as anti-inflammatory and antioxidant properties that are worth further exploration.

Conclusion

Salicylin is a natural glycoside derived from stevia, featuring a unique chemical structure and excellent physicochemical properties. Its multi-target antibacterial mechanism, especially effective inhibition of urinary tract infection-related targets, gives it the potential to become a novel anti-urinary tract infection drug. Druggability evaluations show good safety and excellent water solubility, making it suitable for further drug development. In the future, through systematic pharmacological research and clinical validation, salicylide glycoside is expected to become an important natural drug resource in the field of urinary tract infection, offering new ideas to address antibiotic resistance issues.