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Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
21.7500
3.1308
1.9818
.1103
4.1461
15.9371
High
75.1948
4.1223
No
Yes
No
Yes
No
No
1.2
Yes
No
Yes
No
Calycanthidine (CAS No.: 5516-85-8) is a natural compound with a unique structure, belonging to the cytaldehyde amine organic nitrogen heterocyclic compound, and is classified in the alkaloid family of calyx flowers. As a functional analog, calycanthine, methamethine has attracted widespread attention in the field of natural product pharmacology. In recent years, with the deepening of research on the antiviral activity of natural products, methazine has become one of the hotspots in antiviral drug development due to its remarkable antiviral potential and multi-target mechanism of action. This paper systematically reviews the chemical structure and physicochemical properties of Lamemidin, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, pharmacokinetic characteristics, and clinical application prospects, aiming to provide theoretical basis and practical guidance for further research and drug development of this natural product.
The molecular formula of Lamemidine is C_21H_27N_3O_3, with a molecular weight of 360.5050 Da. Its chemical structure features an acetal amine backbone, containing multiple nitrogen heterocyclic structures, exhibiting strong organic basicity and multifunctional active sites. The structure contains a typical circular system of alkaloids from calyx flowers, giving it a unique spatial conformation and chemical stability. The LogP value of Lamadine is 3.1308, showing moderate lipid solubility that facilitates its penetration through cell membranes. Its topological pole surface area (TPSA) is 21.75 Ų, suggesting its low molecular polarity and possibly good membrane penetration capability. Low water solubility (0.1103 mg/mL) suggests limited solubility in the aqueous phase, but better lipid solubility, which is beneficial for oral absorption and blood-brain barrier penetration.
Notably, Lamadine has a high blood-brain barrier penetration capability, which offers potential advantages for its application in the treatment of central nervous system viral infections. However, the inhibitory activity of hERG channels suggests a possible cardiotoxicity risk and requires focused attention in subsequent drug development. Additionally, the Ames test result was 1.2, indicating a certain genotoxicity risk, and further in vivo and in vitro toxicology evaluation is needed to confirm safety.
Wintersweet is mainly found in plants of the Wintersweet family, especially the roots, stems, and leaves of Calycanthus spp., the genus Wintersweet. These plants are widely distributed in East Asia and North America, and have traditionally been used as traditional Chinese medicinal herbs, with effects such as clearing heat and detoxifying, anti-inflammatory, and relieving pain. As one of its main active ingredients, Pyrometadine undertakes part of its bioactive effects.
Traditional methods for extracting Lamamethine mostly rely on organic solvent extraction combined with column chromatography for separation. The specific process includes: first, use ethanol or methanol to extract dried plant powder by reflux, concentrate the extract, and use the liquid-liquid separation method to remove impurities. It is then purified by silica gel column chromatography or high-performance liquid chromatography (HPLC), ultimately yielding high-purity methamine. In recent years, ultrasound-assisted extraction and supercritical CO_2 extraction technologies have been introduced to improve extraction efficiency and purity, while reducing the use of organic solvents, in line with green chemistry principles.
During extraction, temperature and pH must be controlled to avoid hydrolysis or degradation of the Methamedine structure. Additionally, mass spectrometry (MS), nuclear magnetic resonance (NMR), and infrared spectroscopy (IR) are commonly used to identify purity to ensure the structural integrity and purity of compounds.
Research on the pharmacological activity of Lamethidine has mainly focused on its antiviral effects. In vitro experiments have shown that methamidine has significant inhibitory effects against various viruses, including herpes virus (HSV), human immunodeficiency virus (HIV), and other enveloped viruses. Its antiviral activity manifests through multiple mechanisms including inhibiting viral replication, blocking viral invasion, and interfering with viral gene expression.
Antiherpesvirus activity
Lamethidine effectively inhibits the replication of HSV-1 and HSV-2, showing a low half-effective inhibition concentration (EC_50). Its mechanism involves inhibiting viral DNA polymerase (UL54) and the viral protein ICP27, blocking the transcription and replication processes of viral genes.
Anti-HIV activity
Lamamethine exhibits multi-target inhibitory effects on HIV-1, interfering with the functions of HIV protease (HIV1-PR), integrase (INT), and viral co-receptors CCR5 and CXCR4, thereby inhibiting viral entry and replication. In addition, Lamadine also has certain inhibitory effects on viral reverse transcriptase and other key enzymes, demonstrating broad-spectrum anti-HIV potential.
Other antiviral effects
The study also found that methamide can enhance the body's antiviral ability by regulating the activity of myeloperoxidase (MPO) in the host's immune response. Additionally, its interventions in key targets such as the viral protein UL42 and thymidine kinase (TK) further enhance its antiviral effect.
In addition to antiviral activity, preliminary studies suggest that methamethine has certain anti-inflammatory and immunomodulatory effects, but relevant data are still insufficient and require further systematic research.
The antiviral mechanism of Lamethadine is complex and diverse, mainly achieved through interactions with key proteins in the virus and host cells. Based on molecular docking and cell experiment results, the main molecular targets of labamethine include:
Additionally, methamidine indirectly enhances its antiviral effect by modulating cellular signaling pathways and immune regulatory factors. Its multi-target mode of action gives it high potential in antiviral therapy, especially suitable for interventions against multidrug-resistant viral strains.
The druggability evaluation of Lamemidine indicates it has certain potential for drug development, but it also carries safety risks.
In summary, Lamesidine has certain advantages in druggability, but its safety and pharmacokinetic characteristics require further optimization and validation.
As a multi-target antiviral natural product, Lamethidine has broad clinical application potential. Its ability to effectively inhibit viruses such as HSV and HIV offers new ideas for antiviral drug development. In particular, its inhibitory effects on HIV co-receptors CCR5 and CXCR4 may provide new strategies for treating drug-resistant HIV infection.
The future clinical application prospects of Lamesidine are mainly reflected in the following aspects:
Antiviral drug development
By combining modern drug design technologies, structural optimization reduces toxicity, improves selectivity and bioavailability, and develops novel antiviral drugs. It can be used in combination with existing antiviral drugs to enhance efficacy and delay the development of resistance.
Treatment of central nervous system virus infections
Its high blood-brain barrier penetration ability gives it potential advantages in treating central nervous system viral infections such as meningitis and encephalitis.
Immunomodulation and adjuvant therapy
By modulating MPO and immune-related targets, methamethine may help enhance the body's antiviral immunity and improve the immune status of patients with viral infections.
New drug delivery systems
By utilizing nanotechnology and targeted delivery systems, the targeting and bioavailability of Lamamethine are improved to reduce systemic toxic side effects.
However, the clinical translation of Lamesidine still faces many challenges, such as safety risks, pharmacokinetic uncertainties, and difficulties in scaling production. In the future, pharmacological and toxicological research should be strengthened, preclinical evaluation systems improved, and its entry into clinical trial stages.
As a unique acetal-amine natural calyx flower alkaloid, Lamestine demonstrates multi-target antiviral activity and excellent blood-brain barrier penetration, showing significant potential for drug development. Its complex mechanism of action covers multiple stages including viral replication, invasion, and host immune regulation, providing valuable molecular targets and strategies for antiviral drug design. Despite the risks of cardiotoxicity and genotoxicity, reasonable structural optimization and drug delivery technologies are expected to overcome these obstacles. In the future, combining modern pharmacology, medicinal chemistry, and clinical research, methamethine is expected to become an important candidate for the new generation of antiviral drugs, bringing new breakthroughs in the treatment of viral diseases.
In summary, the research on Lamepidine not only enriches the theoretical framework of natural product pharmacology but also opens new directions for antiviral drug development, worthy of ongoing attention and in-depth exploration by researchers and drug developers.
Shenshuai
Wenjing
Hedandan
