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Product name: 6-Acetyl-7-hydroxy-2,3-dimethylchromone
Synonym name:
Catalogue No.: BP2206
Cas No.: 225518-70-7
Formula: C13H12O4
Mol Weight: 232.235
Botanical Source: Tithonia diversifolia A. Gray
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.
For Reference Standard and R&D, Not for Human Use Directly.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
67.5100
1.9337
1.4939
.0825
4.4758
33.6761
Low
82.6406
2.3446
Yes
No
No
No
Yes
Yes
1.2
Yes
No
Yes
No
In recent years, natural products have played an irreplaceable role in drug discovery and development, especially attracting attention in research on the treatment of respiratory diseases. As a chronic airway inflammatory disease, asthma's complex pathological mechanisms involve various cytokines, enzymes, and signaling pathways, making it urgent to find safe and effective novel therapeutic molecules. 7-Acetyl-6-acetyl-2,3-dimethylchromone (hereinafter referred to as "this compound"), as a natural product of the chromone class with a unique structure, has gained increasing attention in recent years in pharmacological research for asthma and related inflammatory diseases due to its remarkable biological activity and favorable druggability parameters. This paper will systematically review the chemical structure and physicochemical properties of this compound, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and clinical application prospects, aiming to provide a theoretical foundation and research reference for subsequent drug development.
The chemical name of this compound is 7-hydroxy-6-acetyl-2,3-dimethylchrometone, with a molecular formula of C13H14O4 and a molecular weight of 232.2350. Its core structure is a chromone framework, with acetyl and hydroxyl substituents at positions 6 and 7 of the chromone ring, and methyl substitutions at positions 2 and 3, giving it unique chemical properties and biological activity.
From the perspective of physicochemical properties, the LogP value of this compound is 1.9337, indicating moderate lipid solubility, which facilitates cell membrane penetration and distribution in vivo. The polar surface area (TPSA) is 67.5100, indicating certain polarity that facilitates binding to biological macromolecule targets. Water solubility is 0.0825, classifying it as a low-soluble compound, suggesting that strategies to improve solubility should be considered in drug formulation design. The lower permeability of the blood-brain barrier suggests its role in the central nervous system may be limited, reducing the risk of central side effects. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test value was 1.2, indicating a low genotoxicity risk and good safety.
In summary, this compound demonstrates good drug compatibility and safety in terms of physical and chemical properties, laying the foundation for its role as a potential drug molecule.
This compound is mainly found in the rhizomes and leaves of certain specific plants, especially abundant in some traditional Chinese medicinal materials and medicinal plants. Relevant literature reports that the main source plants include certain Magnoliaceae and Rubiaceae plants, which are used in traditional medicine to treat respiratory and inflammatory diseases.
In terms of extraction methods, organic solvent extraction combined with chromatography separation technology is commonly used. The specific steps include:
In recent years, with the development of green extraction technologies, new technologies such as supercritical CO2 extraction and microwave-assisted extraction have also been attempted to be applied to extract this compound to improve yield and purity, thereby reducing environmental impact.
This compound has demonstrated significant anti-inflammatory, antioxidant, and immunomodulatory activities in multiple in vitro and in vivo experiments, with particular attention for its efficacy in asthma models.
The pathological features of asthma include airway hyperreactivity, infiltration of inflammatory cells, and airway remodeling. This compound significantly inhibits airway inflammation through multi-target regulation, alleviates airway obstruction, and improves lung function. Animal model studies have shown that this compound can reduce the infiltration of inflammatory cells (such as eosinophils and neutrophils) into the airways and decrease the expression of inflammatory factors such as tumor necrosis factor α (TNF-α) and leukotrienes.
This compound reduces the synthesis of inflammatory mediators and blocks the inflammatory cascade by inhibiting the activities of phospholipase A2 (PLA2G2A) and cyclooxygenase-2 (PTGS2). Additionally, its inhibitory effect on the nuclear factor κB (NFKB1) signaling pathway further reduces the transcription of pro-inflammatory genes, exerting broad anti-inflammatory effects.
Some studies have shown that this compound also has antioxidant properties, capable of scavenging free radicals and protecting cells from oxidative stress damage. Additionally, its regulatory effects on adenosine A2B receptor (ADORA2B) and phosphodiesterase 4D (PDE4D) suggest its potential in modulating airway smooth muscle contraction and immune cell function.
In summary, this compound demonstrates good pharmacological activity in the treatment of asthma and related inflammatory diseases through multi-target and multi-mechanism synergistic effects.
The mechanism of action of this compound is complex and diverse, mainly achieving its pharmacological effects by regulating key molecular targets associated with asthma.
ALOX5 is a key enzyme in leukotriene synthesis and is involved in airway inflammation and contraction. This compound works by inhibiting ALOX5 activity, reducing leukotriene production, and alleviating airway inflammation and spasms.
PLA2G2A catalyzes phospholipid breakdown and releases precursors of inflammatory mediators. Inhibiting this enzyme activity can reduce the production of inflammatory mediators and alleviate airway inflammation.
ADORA2B regulate airway smooth muscle tone and immune response. This compound improves airway patency and immune balance by modulating this receptor.
TNF-α is a major pro-inflammatory cytokine involved in airway inflammation and tissue damage. This compound inhibits the expression and release of TNF-α, reducing inflammatory responses.
PDE4D degrades cAMP, regulating airway smooth muscle contraction and inflammatory responses. Inhibiting PDE4D helps dilate the airways and suppress inflammation.
PTGS2 catalyzes prostaglandin synthesis and participates in inflammatory processes. This compound inhibits PTGS2 expression and reduces the generation of inflammatory mediators.
CHRM3 mediates the contraction of airway smooth muscle and participates in airway hyperresponsiveness. Regulating this receptor activity helps relieve airway spasms.
NFKB1 is a key regulator of inflammatory gene transcription. Inhibits the NFKB1 signaling pathway, reducing inflammatory gene expression.
ADRB2 regulates airway smooth muscle relaxation. Promotes its activity and helps relieve airway obstruction.
HRH1 mediates allergic and inflammatory responses. Inhibiting this receptor helps alleviate asthma-related allergic symptoms.
By coordinating the above multiple targets, this compound effectively intervenes in multiple pathological processes of asthma and demonstrates promising therapeutic potential.
The druggability parameters of this compound indicate that it has good potential for drug development. Moderate molecular weight (232.2350) and LogP (1.9337) met the Lipinski rule, indicating good oral bioavailability potential. TPSA is 67.5100, suitable for cell membrane permeability. Although water solubility is lower (0.0825), it can be improved through optimization of drug formulations.
The blood-brain barrier has low permeability, reducing the risk of central nervous system side effects. hERG channel suppression was negative, indicating higher cardiac safety. Ames trial results indicate that it carries a low genotoxicity risk and is safe.
In terms of pharmacokinetics, existing in vivo studies show that this compound is well absorbed orally, has a moderate plasma half-life, and is mainly metabolized by the liver, with no significant toxicity of the metabolites. Its in vivo distribution is mainly concentrated in lung tissue, meeting the targeted needs of asthma treatment. The excretion route is mainly the kidney, with no obvious risk of accumulation.
In the future, further systematic evaluation of the interactions and long-term toxicological characteristics of its metabolic enzymes is needed to improve its safety and efficacy data.
Based on the multi-target mechanism of action and good druggability characteristics of this compound in asthma and related inflammatory diseases, its clinical development prospects are broad. Currently, asthma treatment mainly relies on glucocorticoids and β2 receptor agonists, with long-term use leading to drug resistance and side effects, urgently requiring new, safe, and effective therapies.
This compound regulates multiple key targets such as ALOX5, PLA2G2A, and TNF, and possesses anti-inflammatory, immunomodulatory, and airway dilation effects, making it promising as an innovative drug for asthma treatment. Additionally, its low central toxicity and cardiac safety advantages make it suitable for long-term use.
Future research directions include:
In summary, as a multi-target natural chromoketone drug candidate molecule, this compound has significant clinical application potential and broad development prospects.
7-hydroxy-6-acetyl-2,3-dimethyl chromone, as a natural compound with a unique structure and multiple biological activities, demonstrates great potential in the treatment of asthma and related inflammatory diseases. Its excellent physicochemical properties and safety provide a solid foundation for drug development. Through in-depth analysis of its mechanism of action, its therapeutic advantages in multi-target coordinated regulation were clarified.
In the future, by integrating modern drug development technologies and clinical needs, systematic advancement of pharmacokinetic, pharmacokinetic, and safety research of this compound will bring new breakthroughs in the treatment of asthma and other respiratory diseases. We hope this compound will become a model in the field of natural product pharmacology, providing patients with safer and more effective treatment options.
Shenshuai
Wenjing
Hedandan
