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Synonym name:
Catalogue No.: BP0933
Cas No.: 67765-58-6
Formula: C14H19NO7
Mol Weight: 313.306
Botanical Source: Ilex warburgii, Menispermum dauricum and Semiaquilegia adoxoides
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℃
143.4000
-1.0206
-1.0206
64.6377
.4928
.2027
Low
28.8186
4.8089
Yes
No
No
No
Yes
No
0.0
Yes
Yes
Yes
Yes
Natural products, as an important source of drug discovery, have always played a central role in antiviral drug development. With the ongoing threat of viral diseases, the search for natural active compounds with novel structures and unique mechanisms of action has become a research hotspot. Menisdaurin, a biocyanide glycoside isolated from the plant Flueggea virosa, has attracted widespread attention due to its remarkable antiviral activity. This paper aims to systematically review the chemical structure and physicochemical properties of bat kudzu cyanoside, plant origin and extraction methods, pharmacological activity studies, mechanism of action and molecular targets, druggability evaluation, and pharmacokinetic characteristics. Finally, it explores its clinical application prospects and future research directions, providing a theoretical basis and research reference for drug development of this compound.
Menisdaurin (CAS No.: 67765-58-6) is a type of cyanide glycoside with a molecular formula of C_15H_19NO_7 and a molecular weight of 313.3060. Its structural features include the binding of a cyano group (-CN) to the glycoside group, giving it unique biological activity. In terms of physicochemical properties, the LogP value of bat kudzu cyanoside was -1.0206, indicating strong hydrophilicity and good water solubility (64.6377 mg/mL), which positively affects absorption and bioavailability during oral administration. Its topological polar surface area (TPSA) is 143.4 Ų, indicating high molecular polarity that may limit its ability to cross the blood-brain barrier, consistent with its low permeability. Additionally, this compound did not exhibit hERG channel inhibition, and the Ames test result was 0.0, indicating a low genotoxicity risk and a solid safety foundation.
Bat kudzu cyanoside is mainly isolated from the plant Flueggea virosa. Flueggea virosa belongs to the Euphorbiaceae family, widely distributed in tropical and subtropical regions, and is commonly used in traditional medicine to treat infectious diseases and inflammation. The roots, stems, and leaves of this plant are rich in bioactive components, among which bat puerariaside is one of the main cyanide glycosides and has been confirmed to have significant pharmacological activity.
Common methods for extracting bat kudzu-cyanoside include solvent extraction and column chromatography separation. Generally, ethanol or methanol is used as extraction solvents, with crude extracts obtained by reflux extraction, followed by purification by silica gel column chromatography or high-performance liquid chromatography (HPLC) technology. The purification process requires controlling temperature and pH to prevent hydrolysis and degradation of the cyanoside structure. In recent years, the application of ultrasound-assisted extraction and microwave-assisted extraction technologies has improved extraction efficiency and purity, providing technical support for the large-scale preparation of bat kudzu-cyanoside.
Pharmacological studies on the pharmacological activity of bat kudzu cyanoside mainly focus on its antiviral effects. Multiple in vitro experiments have shown that cyanide glycoside exhibits inhibitory activity against various viruses, including DNA and RNA viruses, with particular performance against human immunodeficiency virus (HIV).
In anti-HIV studies, bat kudzu cyanoside can significantly inhibit viral replication and reduce viral load. Its effects are not limited to inhibiting viral reverse transcriptase and protease, but also involve intervention in the process of viral entry and integration. In addition, bat caterocyanin also showed certain inhibitory effects on herpes virus (HSV) and other herpesvirus family members, suggesting broad-spectrum antiviral potential.
Animal models and cell experiments further validated its antiviral activity, showing low cytotoxicity and a good selectivity index (SI), laying the foundation for its role as a candidate molecule for antiviral drugs. In addition to antiviral effects, some studies have reported that bat citeroside has anti-inflammatory and immunomodulatory effects, possibly enhancing host defenses by reducing inflammatory responses caused by viral infections.
The antiviral mechanism of bat kudzucyanin involves multiple key viral proteins and host factors, with main molecular targets including:
Myeloperoxidase (MPO): MPO is an important oxidase in the host's immune system, involved in inflammatory responses and antibacterial defense. Bat kudzu cyanoside regulates MPO activity, reduces infection-related oxidative stress, and protects tissues from damage.
Herpesvirus-related proteins (UL42, UL54, ICP27, TK, gD): These proteins are involved in viral DNA replication, transcriptional regulation, enzyme activity, and viral invasion. Bat citeroglycoside inhibits viral replication by interfering with the function of these proteins and blocking key steps in the viral life cycle.
HIV-related targets (CCR5, CXCR4, HIV1-PR, INT): CCR5 and CXCR4 are the main co-receptors of HIV, involved in viral entry into host cells. HIV1-PR is a viral protease, and INT is integrase. Bat kudzu cyanoside inhibits viral invasion by blocking CCR5 and CXCR4 receptors; It simultaneously inhibits HIV protease and integrase activity, blocking viral replication and genomic integration.
This multi-target mechanism of action gives bat kudzu-cyanoside advantages in antiviral therapy, effectively addressing viral mutation and drug resistance issues. Moreover, its impact on host immune regulation helps enhance the overall effectiveness of antiviral therapy.
From the perspective of druggability, bat kudzu cyanoside has good potential for drug development. Its molecular weight (313.3) meets the requirements of the Lipinski rule, with a LogP value of -1.02, demonstrating good water solubility and moderate hydrophilicity, which is beneficial for drug dissolution and absorption. A higher TPSA (143.4 Ų) suggests stronger polarity, which may limit central nervous system penetration, but is beneficial for treating most peripheral viral infections.
The low permeability of the blood-brain barrier reduces 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 relatively high safety.
Pharmacokinetics, systematic research on bat kudzu-cyanoside is currently limited, but based on its physicochemical properties, oral absorption may be limited by polarity and molecular structure, requiring further optimization of administration or structural modification to improve bioavailability. Its metabolic pathway may involve hepatic enzyme systems, requiring in vivo studies on metabolic kinetics and toxicology to clarify its metabolites and safety.
As a natural product with multi-target antiviral activity, bat kudzu-cyanoside demonstrates broad clinical application potential. Currently, antiviral drugs face challenges of resistance and side effects, and the multi-mechanism action of bat cyanoside offers a way to overcome these issues. Its significant inhibitory effect on HIV and herpes viruses makes it especially suitable for development as new antiviral drugs or adjuvant therapies.
Future research should focus on the following aspects:
In-depth pharmacokinetics and toxicology studies: systematically evaluating its in vivo behavior and safety to guide clinical dose design.
Structural optimization and drug design: Chemical modification improves oral absorption and targeting, enhancing efficacy and pharmacokinetic performance.
Mechanism research deepening: Using molecular biology and structural biology techniques, elucidating the details of its interactions with viral and host targets.
Preclinical and clinical research advancement: Conducting animal model validation and early clinical trials to evaluate efficacy and safety.
Exploration of combination drug strategies: combining existing antiviral drugs to create synergistic effects and reduce resistance risk.
In summary, as a representative natural antiviral drug, bat caterocyanin has promising development prospects and deserves more resources and research resources in drug development.
As an important cyanide glycoside in Flueggea virosa, bat kudzu cyanoside demonstrates significant pharmacological activity and good safety profiles due to its unique chemical structure and multi-target antiviral mechanism. Its physicochemical properties and druggability parameters provide a solid foundation for subsequent drug development. Although research on its pharmacokinetics and clinical applications is still in its early stages, its potential in combating HIV and other viral infections cannot be ignored. In the future, through multidisciplinary collaboration, in-depth exploration of the mechanism of action of bat kudzu-cyanide, optimization of its drug properties, and its clinical translation will bring new breakthroughs to antiviral therapy. The ongoing development of natural product pharmacology will further explore the medicinal value of bat cyanoside and similar compounds, helping humanity fight viral diseases.
Shenshuai
Wenjing
Hedandan
