Product name: Obtucarbamate A
Synonym name: Obtucarbamate A
Catalogue No.: SBP02741
Cas No.: 6935-99-5
Formula: C₁₁H₁₄N₂O₄
Mol Weight: 238.243
Botanical Source:
Physical Description:
Type of Compound: Alkaloids

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
The product could be supplied from milligrams to grams
Inquire for bulk scale.

For Reference Standard and R&D, Not for Human Use Directly.

HPLC of Obtucarbamate A

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

Introduction/Overview

Obtucarbamate A (CAS No.: 6935-99-5) is a natural compound isolated from the traditional Chinese medicinal material Disporum cantoniense, classified as a carbamate compound. In recent years, with the rapid development of natural product pharmacology, Obtucarbamate A has gradually become a research hotspot in the field of respiratory disease treatment due to its remarkable antitussive activity and potential multiple pharmacological effects such as antibacterial and anti-inflammatory effects. The incidence and burden of respiratory diseases such as chronic cough, asthma, chronic obstructive pulmonary disease (COPD), and pulmonary fibrosis are increasing, making it urgent to develop safe and effective therapeutic drugs. Obtucarbamate A, due to its unique chemical structure and good druggability, shows broad clinical application prospects.

This paper systematically reviews the chemical structure and physicochemical properties of Obtucarbamate A, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, focusing on its potential therapeutic value in respiratory diseases and looking ahead to its future clinical application prospects.

Chemical structure and physicochemical properties

Obtucarbamate A is a natural carbamate ester compound with a molecular formula of C_12H_18N_2O_5 and a molecular weight of 254.25. Its structural features include a carbamate group, which gives it unique chemical and pharmacological activity. A LogP value of 2.0 indicates moderate lipid solubility, which is beneficial for cell membrane penetration and distribution in vivo. The polar surface area (TPSA) is 88.36 Ų, and the number of hydrogen bond acceptors is 6, indicating good water solubility and the ability to form hydrogen bonds with biological targets.

Obtucarbamate A has low blood-brain barrier permeability (Low BBB), meaning its risk of side effects in the central nervous system is lower. Both hepatotoxicity and cardiotoxicity are low-risk, and there is no hERG channel inhibitory effect, demonstrating good safety profiles. Although Ames mutagenic assay results are not yet confirmed, its overall toxicology data support its potential as a drug candidate.

Plant Origins and Extraction Methods

Obtucarbamate A is mainly isolated from Disporum cantoniense. Disporum cantoniense belongs to the lily family, widely distributed in southern China. In traditional Chinese medicine, it is often used to treat respiratory diseases such as cough and asthma. The extraction of obtucarbamate A typically follows these steps:

1. Raw material preparation: Collect fresh or dried Disporum cantoniense whole plants or rhizomes and crush them into fine powder.
2. Solvent extraction: Ethanol or methanol is used for reflux extraction, usually taking 2-4 hours, repeating 2-3 times to improve extraction efficiency.
3. Concentration and separation: The extract is concentrated to a certain volume and removed impurities using the liquid-liquid partitioning method.
4. Column chromatography purification: Separation and purification are performed using silica gel column chromatography or high-performance liquid chromatography (HPLC), combined with thin-layer chromatography (TLC) to monitor target components.
5. Structural identification: The structure of Obtucarbamate A is confirmed using nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared spectroscopy (IR).

This extraction process offers high selectivity and recovery rates, ensuring the purity of Obtucarbamate A and the stability of its active ingredients.

Pharmacological activity research

Antitussive activity

Obtucarbamate A was first noticed for its remarkable antitussive effects. In vivo experiments have shown that this compound can effectively suppress cough reactions caused by various irritants, with effects comparable to commonly used clinical antitussive drugs. Its cough-suppressing mechanism involves regulation of various neuroreceptors, which can reduce the sensitivity of the cough reflex.

Antibacterial activity

Obtucarbamate A exhibits certain inhibitory effects on various bacteria and fungi, especially effective against Gram-positive bacteria and certain fungal pathogens. Its targets include key enzyme systems such as bacterial DNA gyrase (GYRA), cell division protein (FTSZ), and dihydrofolate reductase (DHFR), which block bacterial DNA replication and cell wall synthesis. Additionally, it inhibits fungal ERG11 (CYP51A1) enzymes and the multidrug resistance-related protein CDR1, demonstrating broad-spectrum antibacterial potential.

Anti-inflammatory and immunomodulatory effects

Obtucarbamate A demonstrates significant anti-inflammatory effects in models of chronic cough, asthma, and COPD. It can inhibit NF-κB signaling pathway activity, reduce the expression of inflammatory factors TNF-α, IL-5, and IL-13, while regulating matrix metalloproteinases (MMP-2, MMP-9) activity, alleviating tissue damage and airway remodeling. Additionally, by regulating the activities of phospholipase A2 (PLA2G4A) and leukotriene receptor (CYSLTR1), it alleviates airway hyperresponsiveness associated with asthma.

Role in respiratory diseases

Obtucarbamate A modulates P2X3 receptor (P2RX3), TRPV1 receptor, NK1 receptor (TACR1), acetylcholine receptor M3 subtype (CHRM3), and 5-hydroxytryptamine receptor 5-HT3 (HTR3A) related to chronic cough, reducing cough reflex and airway spasms. It also shows certain regulatory activity against common β2-adrenergic receptors (ADRB2) and histamine H1 receptors (HRH1) in asthma patients, suggesting the potential for multi-target synergistic effects.

In the pulmonary fibrosis model, Obtucarbamate A reduces collagen deposition and blocks fibrosis by inhibiting transforming growth factor β1 (TGFB1) and platelet-derived growth factor receptor (PDGFRA). Additionally, regulating CXCL12 chemokines and IL-13 levels helps slow the worsening of inflammation and fibrosis.

Mechanism of action and molecular targets

The multi-target mechanism of Obtucarbamate A forms the basis of its pharmacological activity. Through molecular docking and in vitro experiments, Obtucarbamate A can bind to multiple key proteins and regulate their functions:

• Antibacterial target: binds bacterial DNA gyrase to block DNA replication; Inhibits the cell division protein FTSZ, interfering with bacterial mitosis; Inhibits dihydrofolate reductase DHFR, affecting nucleic acid synthesis; Blocks fungal ERG11 (CYP51A1) enzyme, inhibiting cell membrane synthesis.
• Chronic cough targets: regulate P2X3 receptors and TRPV1 receptors, reduce neural excitability, and suppress cough reflexes; Antagonizes NK1 receptors and reduces neuroinflammation; Regulates the M3 subtype of acetylcholine receptor, relieving airway smooth muscle contraction.
• Asthma targets: activates β2-adrenergic receptors to promote relaxation of airway smooth muscle; Antagonizes leukotriene receptor CysLT1, inhibiting airway inflammation; Inhibits histamine H1 receptors and alleviates allergic reactions.
• COPD target: inhibits the NF-κB signaling pathway, reducing inflammatory factor expression; Regulates MMP-9 activity and reduces tissue damage; Inhibits TNF-α receptors and reduces inflammatory responses.
• Pulmonary fibrosis targets: inhibiting transforming growth factor β1 and platelet-derived growth factor receptors, blocking fibrosis signals; Regulates matrix metalloproteinase-2 to promote extracellular matrix remodeling.

This multi-target mode of action gives Obtucarbamate A a unique advantage in the comprehensive treatment of respiratory diseases.

Druggability evaluation and pharmacokinetics

Druggability evaluation of Obtucarbamate A indicates good drug development potential. The molecular weight is 254.25, which meets the Lipinski rule, with a LogP of 2.0. Its moderate lipid solubility is beneficial for oral absorption. TPSA was 88.36 Ų, indicating moderate polarity, which facilitates biofilm penetration and distribution in vivo.

In terms of safety, Obtucarbamate A demonstrated low hepatotoxicity and low cardiotoxicity, with no hERG channel inhibition, reducing the risk of cardiovascular adverse reactions. The blood-brain barrier has low permeability, which helps reduce central nervous system side effects. The results of the Ames test are still unclear and require further toxicological research.

Regarding pharmacokinetics, although detailed in vivo data are currently lacking, based on its physicochemical properties, it is expected to have good oral bioavailability, wide distribution in vivo, and stable metabolism. Future research needs to further clarify its absorption, distribution, metabolism, and excretion (ADME) characteristics to guide clinical dosage formulation development.

Prospects and outlooks for clinical applications

As a multi-target, multifunctional natural product, Obtucarbamate A shows broad application prospects in the treatment of respiratory diseases. Its antitussive activity makes it a potential novel treatment for chronic cough patients. Its antibacterial and anti-inflammatory properties provide a theoretical basis for its application in both infectious and non-infectious respiratory diseases.

For chronic inflammatory diseases such as asthma and COPD, Obtucarbamate A modulates inflammation and airway responsiveness through multiple targets, potentially improving patient symptoms and slowing disease progression. Research in the field of pulmonary fibrosis offers new therapeutic directions for its anti-fibrotic potential.

In the future, Obtucarbamate A will need to conduct systematic preclinical safety evaluations and pharmacokinetic studies, optimize formulations and administration regimens, and conduct clinical trials to verify its efficacy and safety. Additionally, based on its multi-target mechanism of action, synergistic treatment strategies combining with other drugs are also worth exploring.

Conclusion

As an important active ingredient in Disporum cantoniense, Cypressus cantoniense A shows great potential in the treatment of respiratory diseases due to its unique chemical structure and multi-target pharmacological activity. Its excellent druggability and safety lay a solid foundation for subsequent drug development. In the future, through in-depth mechanistic research, pharmacokinetic analysis, and clinical validation, Obtucarbamate A is expected to become a novel therapeutic drug for chronic cough, asthma, COPD, and pulmonary fibrosis, promoting the application of natural product pharmacology in modern medicine.