Synonym name: 4-Formylphenyl b-D-allopyranoside
Catalogue No.: BP0715
Cas No.: 80154-34-3
Formula: C₁₃H₁₆O₇
Mol Weight: 284.264
Botanical Source: Obt. from seeds of Helicia erratica

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.

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

Introduction/Overview

Natural products, as important resources for drug development, attract much attention due to their structural diversity and biological activity. Helicide (CAS No.: 80154-34-3) is a natural glycoside compound with potential pharmacological activity, and in recent years, it has shown significant research value in the field of sedative and hypnotic activity. As the incidence of sleep disorders and related neuropsychiatric disorders rises year by year, developing safe and effective sedative-hypnotic drugs has become an urgent medical challenge to solve. Tofu glycoside, due to its unique molecular structure and multi-target mechanism, has become a hot topic in natural product pharmacology research.

This paper aims to systematically review the chemical structure and physicochemical properties of tofu fructoside, plant origin and extraction methods, pharmacological activity, mechanism of action and molecular targets, druggability evaluation, and pharmacokinetic characteristics. Combined with existing research findings, it explores its potential and development prospects in clinical applications, providing references for research and drug development in related fields.

Chemical structure and physicochemical properties

Tofu fructoside is a glycoside compound with the molecular formula C_13H_16O_7 and a molecular weight of 284.2640. Its structural features include a glycoconic part connected to a glycosidic group via glycosidic bonds, giving it high polarity and water solubility. The LogP value of tofu frucin was -0.6208, indicating strong hydrophilicity, and the polar surface area (TPSA) was 116.45 Ų, further supporting its good water solubility (20.2272 mg/mL). These physicochemical properties have significant impacts on its pharmacokinetic behavior and bioavailability.

Structurally, frucin contains multiple hydroxyl and ether bonds, which may participate in hydrogen bond formation and enhance its ability to bind to biological targets. It has good structural stability and no significant mutagenicity (Ames test result is 0.0), does not inhibit cardiac potassium channel hERG, and demonstrates good safety potential.

Plant Origins and Extraction Methods

Tofu frucin is mainly found in certain traditional Chinese medicinal herbs and wild plants, especially the fruits and rhizomes of legumes. Specific plant species include, but are not limited to, some flavonoid-rich plants, such as the fruits of the legume genus. Due to its low content, the extraction and purification process is relatively complex.

Common extraction methods include solvent extraction, ultrasound-assisted extraction, and high-performance liquid chromatography (HPLC) separation and purification. Ethanol or methanol is generally used as extraction solvents, optimizing extraction efficiency by adjusting pH and temperature conditions. During purification, high-purity tofu glycoside was obtained using silica gel column chromatography, reversed-phase C18 column chromatography, and preparative HPLC technology.

In recent years, green extraction technologies such as supercritical CO_2 extraction and microwave-assisted extraction have also been attempted to extract tofu glutin to improve yield and reduce environmental impact.

Pharmacological activity research

The pharmacological activity of fructoside is mainly concentrated in the central nervous system, especially showing significant sedative and hypnotic effects. In vivo and in vitro experiments show that tofu glycoside can extend sleep duration and improve sleep quality, with relatively few side effects.

In animal models, tofu fructoside can be administered orally or by injection, significantly reducing mouse activity levels, promoting rapid onset of sleep, and prolonging non-rapid eye movement (NREM) sleep time. Compared to traditional sedative-hypnotic drugs, tofu frin exhibits a lower risk of tolerance and dependence.

In addition, tofu frucin also has certain anti-anxiety and antidepressant effects, possibly related to its regulation of the neurotransmitter system. Some studies have shown that it regulates the systems of 5-hydroxytryptamine (5-HT) and γ-aminobutyric acid (GABA), suggesting its potential application value in the treatment of neuropsychiatric disorders.

Mechanism of action and molecular targets

The sedative and hypnotic effects of tofu frin involve various neurotransmitter receptors and transport proteins, with main targets including:

• SLC6A4 (serotonin transporter): Tofu frin may regulate SLC6A4 activity, influence 5-HT reuptake, and increase 5-HT concentration in the synaptic cleft, thereby exerting anti-anxiety and sedative effects.

• HTR2A and HTR1A (5-HT receptor subtypes): As key receptors of 5-HT, HTR2A and HTR1A are involved in regulating the sleep-wake cycle. Tofu frucin regulates neuronal excitability by binding to these receptors, promoting sleep.

• GABRA1, GABRB2, GABRG2 (GABA_A receptor subunits): GABA_A receptors are the main inhibitory agents of the central nervous system. Tofufrin may enhance the GABA_A receptor-mediated chloride ion influx, enhancing neuroinhibition and exerting a sedative and hypnotic effect.

Molecular docking and cell-level experiments support the binding ability of tofufrin to the above targets, suggesting its multi-target synergistic mechanism. This multi-target characteristic not only enhances the broad spectrum of efficacy but also reduces the risk of resistance to a single target.

Druggability evaluation and pharmacokinetics

The druggability parameters of tofu periposide indicate that it has certain development potential. It has a moderate molecular weight, good water solubility, and does not inhibit hERG channels, reducing the risk of cardiotoxicity. A negative Ames test indicates a low genotoxicity risk.

However, tofu frin has a relatively low blood-brain barrier (BBB) penetration capacity, which may limit the efficacy of drugs in the central nervous system. To overcome this limitation, researchers are exploring structural modification, nanocarrier delivery, and drug synergy strategies to enhance brain bioavailability.

Pharmacokinetic studies show that tofu glycoside is absorbed orally relatively quickly, but metabolism in the body is relatively rapid, mainly through hepatic metabolic enzymes. Its half-life is moderate, making it suitable for routine administration. The activity and safety of metabolites still require further systematic research.

Prospects and outlooks for clinical applications

With deeper understanding of sleep disorders and neuropsychiatric disorders, the demand for the development of naturally derived sedative hypnotic drugs is steadily increasing. Due to its excellent safety and multi-target mechanism of action, tofu glycoside shows potential as a novel sedative hypnotic drug.

The future clinical application prospects are mainly reflected in the following aspects:

1. Treatment of sleep disorders: For insomnia and sleep structure disorders, tofu orin can be used as a single or adjunct medication to improve sleep quality and reduce dependence and side effects.

2. Adjunctive therapy for neuropsychiatric disorders: Its regulatory role in the 5-HT and GABA systems gives it potential value in adjunctive treatment for anxiety, depression, and other conditions.

3. Safety advantages: No significant mutagenicity or cardiotoxicity, providing safety for long-term use.

4. Combination therapy strategy: Combined with existing sedative hypnotic drugs, potentially achieving dose reduction, enhanced efficacy, and alleviation of side effects.

However, clinical translation of frucin still faces challenges such as low blood-brain barrier penetration and the need for optimized pharmacokinetic properties. Future research should focus on dosage form innovation, structural optimization, and clinical trial design to promote the transition from the laboratory to the clinic.

Conclusion

Tofu fructoside, as a natural glycoside with a unique structure and multi-target mechanism, demonstrates excellent sedative and hypnotic pharmacological activity as well as safety. Its role in regulating the 5-HT and GABA nervous systems provides a theoretical foundation and practical direction for the development of novel central nervous system drugs.

Although there are still limitations in blood-brain barrier penetration and the need for further improvement in pharmacokinetics, with the development of extraction and purification technologies and drug delivery systems, the clinical application prospects of frucin are promising. In the future, through multidisciplinary collaboration, tofu frin is expected to become an effective natural medicine for treating sleep disorders and related mental illnesses, bringing hope to patients.

In summary, research on frucin not only enriches the knowledge system in the field of natural product pharmacology, but also provides valuable candidate molecules and ideas for new drug development, possessing significant scientific value and application potential.