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Product name: Usnic acid
Synonym name: Usninic acid; Carbonusninic acid
Catalogue No.: BP1427
Cas No.: 125-46-2
Formula: C18H16O7
Mol Weight: 344.319
Botanical Source: Usnea diffracta Vain.
Physical Description:
Type of Compound: Miscellaneous
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.
Chengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，TCM), Natural Active Pharmaceutical Ingredients worldwide.
The main services:
A. Supply active ingredients and reference standards of TCM, from mgs to kgs scale
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR(contract research), CM(contract manufacture) and PD(process development) services from lab scale, pilot scale to commercial scale(GMP is also available)
E. TCM compounds library for drug screen,more than 3000 compounds available, many of them are rare and unique.
HPLC of Usnic acid
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
117.9700
1.7765
-.3937
.4778
3.6458
10.3356
Low
85.7862
4.2483
Yes
No
Yes
No
Yes
Yes
0.6
Yes
No
Yes
No
Usnic acid (CAS No.: 125-46-2) is a naturally occurring diterpene compound, mainly found in lichens, especially abundant in plants of the genus Usnea spp. As one of the lichen metabolites, pyrostyric acid has attracted widespread attention in recent years in pharmacology and natural product drug development due to its diverse bioactivity and unique molecular structure. Research shows that pinylic acid not only exhibits significant antibacterial, anti-inflammatory, and antitumor activities, but also exerts multiple pharmacological effects by regulating intracellular signaling pathways, especially showing unique advantages in inhibiting the mammalian rapamycin target protein complex (mTOR) signaling pathway.
The mTOR signaling pathway, as a key regulatory hub for cell growth, proliferation, and metabolism, plays an important role in tumor development, inflammatory responses, and various metabolic diseases. By binding mTOR to ATP-binding pockets, turbinic acid effectively inhibits the activity of the mTORC1 and mTORC2 complexes, thereby regulating the phosphorylation levels of its downstream effector proteins Akt, 4EBP1, and S6K, inducing cellular autophagy, and demonstrating promising anti-tumor potential. Additionally, methrolic acid exhibits significant antibacterial activity against various Gram-positive bacteria such as Staphylococcus aureus and Enterococcus faecalis, indicating its potential as an anti-infective drug.
This paper systematically reviews the chemical structure and physicochemical properties of mesolic acid, its plant origins and extraction methods, explores its pharmacological activity and mechanism of action in depth, evaluates its druggability and pharmacokinetic characteristics, and looks ahead to its clinical application prospects, aiming to provide scientific basis and theoretical support for further research and development of mesolic acid.
Pinylic acid is a diterpenoid compound with a complex bicyclic structure, molecular formula C18H16O7, and molecular weight of 344.3190. Its structure consists of two benzene rings connected by a dioxan bridge, forming a unique diterpene phenol framework with multiple hydroxyl and keto functional groups. The LogP value of plenic acid is 1.7765, indicating moderate lipid solubility that facilitates cell membrane penetration; TPSA (Topological Polar Surface Area) is 117.9700, reflecting moderate polarity that facilitates binding with biological macromolecules. Low water solubility (0.4778 mg/mL) suggests limited solubility in the aqueous phase, which may affect its bioavailability.
The stereochemical form of pentoliic acid is (+)-pentylic acid, which exhibits specific optical activity, which is significant for its binding to biological targets. Multiple phenolic hydroxyl groups in its structure give it antioxidant properties and also affect its chemical stability. Turpentine does not inhibit hERG channels, indicating a lower risk of cardiotoxicity; The Ames test result was 0.6, indicating a low genotoxicity risk and meeting drug safety requirements.
Pinecic acid mainly comes from lichens, especially the genus Usnea spp.. Lichens of the genus Songluo are widely distributed in temperate and frigid regions worldwide, and are attached to bark, rocks, and other surfaces. Its biosynthetic pathway involves multiple enzymatic reactions, ultimately forming the biologically active turpentine acid.
Traditional extraction methods mainly use organic solvent extraction methods, such as ethanol, acetone, or methanol, combined with ultrasound-assisted extraction technology to improve extraction efficiency. The extraction process typically includes the following steps:
In recent years, supercritical CO2 extraction and microwave-assisted extraction technologies have also been applied to the extraction of truffolic acid, significantly improving extraction efficiency and purity, while reducing the use of organic solvents, in line with the concept of green chemistry.
Pyrosic acid exhibits significant inhibitory effects on various Gram-positive bacteria, especially strong antibacterial activity against commonly clinically pathogenic bacteria such as Staphylococcus aureus and Enterococcus faecalis. Its mechanism involves interfering with multiple targets such as bacterial DNA replication, protein synthesis, and cell wall synthesis, specifically including inhibition of key enzymes like DNA gyrase, fatty acid synthase (FABI), and dihydrofolate reductase (DHFR).
Additionally, pinerate also showed certain inhibitory effects against resistant strains such as methicillin-resistant Staphylococcus aureus (MRSA), suggesting its potential application value against infections by resistant bacteria. Its antibacterial spectrum is relatively narrow, mainly targeting Gram-positive bacteria, with weaker activity against Gram-negative bacteria.
Turbenic acid significantly reduces phosphorylation levels of Akt (Ser473), 4EBP1, and S6K in tumor cells by inhibiting the mTOR signaling pathway, blocking cell proliferation signals, inducing cell cycle arrest and autophagy, and promoting tumor cell apoptosis. Multiple in vitro cell experiments and in vivo tumor models have validated its anti-tumor potential, covering various solid tumor types including lung cancer, breast cancer, and liver cancer.
Plenic acid-induced autophagy not only promotes tumor cell death but may also enhance the sensitivity of chemotherapy drugs, demonstrating their potential as adjunctive anticancer drugs. Additionally, pine acid regulates inflammatory responses in the tumor microenvironment, further inhibiting tumor progression.
Pyloric acid can significantly inhibit the release of inflammatory mediators such as tumor necrosis factor α (TNF-α), interleukin-6 (IL-6), and nitric oxide (NO), thereby reducing inflammatory responses. Its anti-inflammatory mechanism partially relies on regulation of the mTOR signaling pathway, reducing the transmission of pro-inflammatory signals and protecting tissues from inflammatory damage.
Both in vitro and animal model studies have shown that pyroxylic acid has good therapeutic effects in various inflammatory diseases such as arthritis, skin inflammation, and lung inflammation, suggesting its potential as a natural anti-inflammatory drug.
The main pharmacological mechanism of pinylic acid focuses on regulating the mTOR signaling pathway. mTOR, as a core regulator of cell growth and metabolism, is present in two distinct complexes, mTORC1 and mTORC2. Pyretic acid inhibits its kinase activity by binding the ATP-binding pocket of mTOR protein, thereby blocking mTORC1/2 signaling.
The specific mechanisms include:
Additionally, the effects of pine acid on bacteria involve multi-target synergistic inhibition, including:
These multi-target mechanisms give perulic acid broad-spectrum antibacterial activity and a lower risk of resistance.
The druggability parameters of pulonic acid indicate its promising potential for drug development. The molecular weight is 344.3190, within the range of the Lipinski rule; the LogP is 1.7765, indicating moderate lipid solubility, favorable for oral absorption and cell membrane penetration; the TPSA is 117.9700, within the range suitable for oral bioavailability.
Low water solubility (0.4778 mg/mL) may limit oral bioavailability and in vivo distribution, requiring formulation improvement or optimization of drug delivery systems. Pyrelate has low blood-brain barrier penetration ability, suggesting limited application in central nervous system diseases but also reducing the risk of central nervous system toxicity.
In terms of safety, trylic acid does not inhibit hERG channels, reducing the risk of cardiotoxicity; The Ames trial result was 0.6, indicating a low genotoxicity risk and meeting safety requirements for clinical development.
Pharmacokinetic studies show that turthrolicic acid is metabolized stably in the body, mainly processed by the hepatic metabolic enzyme system, with excretion primarily via bile and feces. Its half-life is moderate, making it suitable for routine administration. Further research is needed in the future on the activity and toxicity of its metabolites to improve safety evaluation.
With its multiple pharmacological activities, especially its potential in anti-tumor, antibacterial, and anti-inflammatory fields, pinerate has become a hot topic in natural drug development. Its unique mechanism of inhibiting the mTOR signaling pathway offers new ideas for tumor treatment, potentially serving as a monotherapy or adjunct to chemotherapy to improve tumor treatment outcomes and reduce drug resistance.
In terms of antibacterial activity, pine-sulfate exhibited activity against various Gram-positive pathogens and its inhibitory effect on drug-resistant strains, suggesting its potential for application in anti-infective drug development. In the future, structural modification can enhance its antibacterial spectrum and water solubility, expanding clinical indications.
Its anti-inflammatory activity gives turpentic acid great potential for use in chronic inflammatory diseases such as arthritis, skin diseases, and respiratory inflammation. Combined with its lower toxicity risk, it is expected to be developed as a safe and effective natural anti-inflammatory drug.
However, the water solubility and bioavailability of pinerate limit its clinical application, requiring drug delivery systems (such as nanocarriers and liposomes) or chemical modifications to enhance its pharmacokinetic properties. At the same time, systematic preclinical and clinical trial data are still lacking. In the future, pharmacodynamics, safety, and clinical research should be strengthened to promote clinical translation.
As a widely sourced lichen natural product, pyrostyric acid shows broad application prospects in anti-tumor, antibacterial, and anti-inflammatory fields due to its unique chemical structure and multi-target pharmacological activity. It regulates cell growth and metabolism by inhibiting the mTOR signaling pathway, inducing autophagy and exerting antitumor effects; It also has a significant inhibitory effect on various Gram-positive bacteria, showing potential for developing novel anti-infective drugs.
Although pentylic acid has a good druggability foundation and safety characteristics, its poor water solubility and low bioavailability still need to be overcome. Future research should focus on structural optimization, innovation in drug delivery technology, and systematic clinical evaluation to promote trine-bin from the laboratory to clinical application, benefiting patients.
In summary, as an important subject of natural product pharmacological research, melanin has significant scientific value and application potential, making it a star compound that cannot be ignored in the future field of natural drug development.
Shenshuai
Wenjing
Hedandan
