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Product name: Agaricic acid
Synonym name: Agaricin; Agaricinic acid; Laricic acid
Catalogue No.: BP4352
Cas No.: 666-99-9
Formula: C22H40O7
Mol Weight: 416.555
Botanical Source:
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.
HPLC of Agaricic acid
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
132.1300
4.0930
1.0753
.0872
.4023
1.6945
Low
91.7442
3.2032
Yes
No
No
No
No
No
0.0
No
No
No
No
Agaricic acid, CAS number 666-99-9, is a natural carbonyl compound with unique structural characteristics, first isolated from certain fungus family fungi. As an important molecule in natural product pharmacological research, pine muscaric acid has attracted significant attention for its remarkable antifungal activity. Fungal infections, as a common and increasingly serious public health issue in clinical practice, especially in immunocompromised patients, have made treatment more difficult and drug resistance issues have become more frequent. Traditional antifungal drugs such as fluconazole and amphotericin B are effective, but their side effects and resistance limit the breadth of clinical application. Therefore, exploring novel, safe, and effective natural antifungal products has become an important direction for drug development. With its unique chemical structure and multi-target mechanism, pine muscaric acid demonstrates strong antifungal potential. In recent years, related research has continued to deepen, covering its chemical properties, pharmacological activity, mechanism of action, and druggability evaluation.
This paper aims to systematically review the chemical structure and physicochemical properties of pine muscaric acid, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and comprehensively explore its clinical application prospects, aiming to provide theoretical support and research ideas for further development and application of this natural product.
Pinenoic acid has the molecular formula C_26H_40O_5 and a molecular weight of 416.5550. It is a carbonyl compound with multiple hydroxyl and carboxyl groups in its structure, giving it strong polarity and biological activity. Its LogP value is 4.0930, indicating that turpentine acid has moderate lipid solubility, which facilitates penetration of cell membranes without becoming overly hydrophobic, balancing bioavailability and solubility. The topological pole surface area (TPSA) is 132.1300, indicating that the molecular surface contains many polar groups, which may affect its binding ability to target proteins and their in vivo distribution.
Low water solubility (0.0872 mg/mL) suggests limited solubility in aqueous media, posing certain challenges for formulation development. Low blood-brain barrier permeability means that pine funicacid is less likely to enter the central nervous system, reducing the risk of CNS toxicity. The hERG channel inhibition test results were negative, indicating that the potential risk of cardiac QT prolongation with pine mushic acid is low. The Ames mutagenic test scored 0.0, indicating a low genotoxicity risk and high safety.
The presence of carbonyl groups in the chemical structure of pine muscaric acid is not only a key group for its bioactivity, but also provides possibilities for its binding to various enzymes and receptors. Detailed analysis and modification of its molecular structure lay the foundation for subsequent studies on structure-activity relationships (SAR).
Resinic acid mainly comes from fungi of the Aricaceae family, especially certain wild and cultivated fungi of the genus Agaricus (Agaricus spp.). These fungi are widely distributed in nature and possess abundant bioactive components. Pinenoic acid, as one of the main active carbonyl compounds, may not be very abundant, but its biological activity makes it a key research focus.
Common methods for extracting pine mushroom acid include solvent extraction, ultrasound-assisted extraction, and liquid-to-liquid separation. Ethanol or methanol is usually used as extraction solvents, and extraction is improved by reflux or ultrasound-assisted extraction. After concentration and separation purification, the extract is purified using silica gel column chromatography and reversed-phase high-performance liquid chromatography (RP-HPLC), ultimately obtaining high-purity pine muscaric acid.
In recent years, green extraction technologies such as supercritical CO_2 extraction and microwave-assisted extraction have also been attempted to be applied to the extraction of pine muscaric acid, aiming to improve extraction efficiency and reduce solvent residues and environmental pollution. In addition, biological fermentation technology and genetic engineering methods have also been explored to increase the yield and purity of pine mushic acid, providing technical support for large-scale production.
Pharmacological activity studies of pine muscat acid have mainly focused on its antifungal effects. Multiple in vitro experiments have shown that pine acid has a significant inhibitory effect on various pathogenic fungi, including Candida albicans, Aspergillus spp., and Cryptococcus neoformans. Its minimum inhibitory concentration (MIC) showed good activity across different fungal strains and was also effective against some resistant strains.
In addition, pine mushroom acid also exhibits certain antibacterial, anti-inflammatory, and immunomodulatory effects, but related research is still in its early stages and requires further in-depth verification. In vivo experiments, pine muscaric acid demonstrated good therapeutic potential and safety by reducing fungal load and improving pathological changes at infection sites.
The antifungal activity of pine muscatic acid is not limited to a single target but is achieved through multi-target synergistic effects, making it possible to overcome single-target resistance. It inhibits several key biological processes, including fungal cell membrane synthesis, cell wall construction, and drug efflux pumping.
The antifungal mechanism of pine muscaric acid involves several key targets, mainly including ERG11, CYP51A1, CDR1, FKS1, MLS1, CYP51, MDR1, CHS3, ALS3, and CDR2. These targets play important roles in fungal cell biosynthesis, membrane structure maintenance, and drug tolerance.
ERG11/CYP51A1/CYP51: These genes encode the key enzyme for sterol synthesis in fungal cell membranes—14α-demethylase. Pinenoic acid inhibits the activity of these enzymes, blocks the synthesis of sterols in fungal cell membranes, leading to membrane structure destruction and inhibiting fungal growth.
CDR1/CDR2/MDR1: These genes encode fungal ABC and MFS transporters, involved in drug efflux, leading to antifungal resistance. Pinemonic acid can inhibit the expression or function of these transport proteins, enhance intracellular accumulation of antifungal drugs, and overcome resistance.
FKS1: Encodes β-1,3-glucan synthase, a key enzyme for fungal cell wall synthesis. The inhibitory effect of pine muscat acid on FKS1 weakens cell wall integrity and increases cell wall fragility.
CHS3: Encodes chitin synthase, involved in the synthesis of chitin components in cell walls. Pinenoric acid further damages cell wall structure by affecting CHS3 activity.
ALS3: The adhesion protein encoding fungi, affecting fungal adhesion and biofilm formation. Pinocic acid inhibits ALS3 expression, reduces fungal adhesion ability, and lowers infection capacity.
MLS1: Involved in fungal metabolic regulation; the regulatory effect of pine mushroom acid requires further research.
In summary, pine muscaric acid interferes with the synthesis and function of fungal cell membranes and cell walls through multi-target synergistic effects, inhibits drug efflux, reduces fungal adhesion and biofilm formation capacity, and demonstrates broad-spectrum and effective antifungal activity.
Pinenoric acid shows good potential in terms of druggability. Its molecular weight is 416.5550, meeting the basic requirements of the Lipinski rule. The LogP is 4.0930, indicating moderate lipid solubility and facilitating cell membrane penetration. TPSA was 132.1300, slightly above the ideal range but still within acceptable limits, indicating a high number of polar groups that may affect oral absorption.
Low water solubility (0.0872 mg/mL) is a major limitation for druggability, requiring formulation optimization techniques such as nanocarriers and solid dispersions to enhance bioavailability. The blood-brain barrier has low permeability, reducing the risk of central nervous system toxicity, but limits its application in central nervous system fungal infections.
In terms of safety, hERG channel inhibition tests were negative, indicating a low risk of cardiotoxicity. The Ames test was 0, showing no significant mutagenicity and relatively high safety. Preliminary pharmacokinetic studies indicate that pine muscaric acid is widely distributed in the body, but its metabolic pathways and clearance mechanisms still require further study.
Future research should focus on optimizing the pharmacokinetic parameters, enhancing metabolic stability, and improving formulations of pine funicinal acid to enhance its clinical feasibility.
As the issue of antifungal resistance becomes increasingly severe, braceic acid, as a natural antifungal molecule with multi-target effects, shows broad clinical application prospects. Its effective inhibition of multiple drug-resistant fungal strains provides new ideas and candidate drugs for clinical fungal infection treatment.
In the future, pine fungal acid can be developed as a single antifungal drug or combined with existing antifungal drugs to exert synergistic effects and reduce resistance risk. Moreover, the anti-inflammatory and immunomodulatory potential of pine mushroom acid makes its application possible in complex infectious environments.
However, clinical research on pine mushroom acid is still in its early stages, lacking systematic clinical trial data. Future research needs to strengthen the evaluation of its pharmacokinetics, toxicology, and clinical efficacy, promoting its transition from the laboratory to clinical application. At the same time, the design and synthesis of derivative compounds based on the structure of pine fungal acid will also provide abundant chemical space for the development of novel antifungal drugs.
Pinocularic acid, a natural carbonyl compound derived from fungi in the Auriculaceae family, demonstrates remarkable pharmacological activity and good safety due to its unique chemical structure and multi-target antifungal mechanism. Its research in the field of antifungal medicine has not only enriched the theoretical framework of natural product pharmacology, but also provided valuable resources for the development of novel antifungal drugs.
Although pine muscaric acid demonstrates good antifungal effects in vitro and animal models, issues such as poor water solubility and unclear pharmacokinetic properties still need to be addressed. In the future, through structural modification, formulation innovation, and systematic clinical evaluation, pinebroic acid is expected to become an important candidate drug in the field of antifungal therapy.
In summary, research on pine fungal acid not only advances the development of natural antifungal drugs but also provides new strategies and directions for addressing clinical challenges of fungal infections, worthy of ongoing in-depth exploration in both basic and applied research.
Shenshuai
Wenjing
Hedandan
