Product name: Purpurogallin carboxylic acid
Synonym name:
Catalogue No.: BP2106
Cas No.: 5146-12-3
Formula: C12H8O7
Mol Weight: 264.189
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.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
135.2900
.8159
-1.4758
1.0956
2.6650
1.7159
Low
85.6396
2.6386
Yes
No
No
No
Yes
Yes
0.6
Yes
No
Yes
No
Purpurogallin carboxylic acid (hereinafter referred to as PPGCA) is a natural phenolic compound originally derived from the papavevery plant Macleaya microcarpa (Maxim.) Separated from Fedde. In recent years, with the rapid development of natural product pharmacology, PPGCA has become a research hotspot due to its unique chemical structure and significant biological activity, especially its anticancer and neuroprotective effects. Additionally, PPGCA is an oxidation product of gallic acid in fermented tea, demonstrating its potential value in food science and functional beverages. This paper will systematically review the chemical structure, plant origin, pharmacological activity, mechanism of action, and druggability evaluation of PPGCA, aiming to provide theoretical basis and research directions for its future drug development and clinical application.
PPGCA has the molecular formula C12H8O7 and a molecular weight of 264.1890, classifying it as a polyhydroxyphenolic compound. Its structural core is a purpurogallin backbone with a carboxyl substitution, giving it strong polarity and water solubility (1.0956, unit unspecified but usually mg/mL or g/L). PPGCA has a LogP value of 0.8159, indicating moderate lipophilicity, which facilitates cell membrane penetration without being overly hydrophobic, balancing bioavailability and solubility. The polar surface area (TPSA) is 135.29 Ų, suggesting that the molecules have strong polar groups, which may affect their ability to pass through biological barriers. The low permeability of the blood-brain barrier indicates limited distribution in the central nervous system. The hERG channel inhibition test was negative, indicating that PPGCA has good cardiac safety. The Ames mutagenic test scored 0.6, indicating a low genotoxicity risk and meeting safety requirements for drug development.
PPGCA mainly originates from Macleaya microcarpa (Maxim.) Fedde, this plant holds an important position in both traditional Chinese medicine and modern herbal medicine research. M. microcarpa belongs to the Papaveraceae family, widely distributed in China and East Asia, and contains various bioactive components. PPGCA, as a secondary metabolite, is usually found in plant roots, stems, and leaves.
Common methods for extracting PPGCA include solvent extraction, liquid-liquid partitioning, and chromatographic purification. Typically, ethanol or methanol aqueous solutions are used for reflux extraction of dried plant materials, followed by liquid-liquid extraction to remove fat-soluble impurities. Separation and purification were performed using silica gel column chromatography or high-performance liquid chromatography (HPLC) technology, ultimately resulting in high-purity PPGCA. In recent years, ultrasound-assisted extraction and microwave-assisted extraction technologies have been applied to improve extraction efficiency and reduce solvent usage, providing technical support for industrial production. Additionally, PPGCA, as an oxidation product of gallic acid in fermented tea, can also be obtained indirectly through fermentation processes, expanding its source pathways.
The anticancer activity of PPGCA is currently a key research focus. Multiple in vitro cell experiments have shown that PPGCA has significant inhibitory effects on various cancer cell lines, including breast, lung, liver, and colorectal cancers. Its anti-cancer mechanisms mainly involve inducing apoptosis, inhibiting cell proliferation, and blocking tumor-related signaling pathways. PPGCA can regulate cell cycle-related protein expression, promote cell cycle arrest, and activate mitochondrial pathways to induce apoptosis. Additionally, PPGCA has demonstrated the ability to inhibit tumor cell migration and invasion, suggesting potential in anti-metastasis efforts.
PPGCA has shown good protective effects in neurodegenerative disease models. Its targets include NFE2L2 (nuclear factor red cell 2-related factor 2), SOD1 (superoxide dismutase 1), CAT (catalase), GPX1 (glutathione peroxidase 1), and HMOX1 (heme oxygenase 1), among other antioxidant-related enzymes. These targets play key roles in cellular antioxidant defense and inflammation regulation. PPGCA activates the NFE2L2 signaling pathway, enhances intracellular antioxidant enzyme expression, reduces oxidative stress damage, and delays the degenerative process of neurons. Additionally, PPGCA can suppress neuroinflammatory responses, regulate the neuronal microenvironment, and protect nerve function.
In addition to anticancer and neuroprotection, PPGCA also exhibits multiple biological activities including anti-inflammatory, antibacterial, and antioxidant properties. Its anti-inflammatory effects mainly occur by inhibiting the release of inflammatory mediators and modulating inflammatory signaling pathways. Its antioxidant activity stems from its multi-hydroxyl structure, which can effectively eliminate free radicals and protect cells from oxidative damage. Some studies have also found that PPGCA has protective effects on the cardiovascular system, can improve vascular endothelial function, and inhibit the occurrence of atherosclerosis.
The biological effects of PPGCA are based on its interactions with multiple molecular targets, especially in anticancer and neuroprotective fields.
PPGCA exerts its anti-cancer effects through multiple signaling pathways. First, PPGCA can activate mitochondria-dependent apoptosis pathways, regulate the expression of Bcl-2 family proteins, promote cytochrome C release, and activate the caspase cascade, ultimately leading to cancer cell apoptosis. Second, PPGCA inhibits the PI3K/Akt and MAPK signaling pathways, blocking tumor cell proliferation and survival signals. Additionally, PPGCA regulates the NF-κB pathway, reduces pro-inflammatory factor expression, suppresses inflammatory responses in the tumor microenvironment, and blocks tumor progression.
The role of PPGCA in neurodegenerative diseases mainly depends on its antioxidant and anti-inflammatory properties. PPGCA activates the NFE2L2 transcription factor, promoting the expression of downstream antioxidant enzymes such as SOD1, CAT, GPX1, and HMOX1, thereby enhancing cellular resistance to oxidative stress. By removing excess reactive oxygen species (ROS), PPGCA reduces neuronal damage. Additionally, PPGCA inhibits inflammatory signaling pathways such as NF-κB and MAPK, lowers pro-inflammatory cytokine levels, and protects nerve cells from inflammation-mediated damage. This mechanism helps slow the progression of neurodegenerative diseases such as Parkinson's and Alzheimer's.
PPGCA may also participate in maintaining cellular homeostasis and disease prevention by regulating intracellular metal ion homeostasis, inhibiting lipid peroxidation, and modulating autophagy pathways. Future research needs to further clarify the specific molecular action networks and upstream and downstream signaling pathways.
PPGCA's druggability parameters indicate its promising drug development potential. The molecular weight of 264.1890 complies with the Lipinski rule, with a moderate LogP value of 0.8159, which is beneficial for oral absorption. Higher TPSA (135.29 Ų) and water solubility (1.0956) indicate strong hydrophilicity, but may also limit its ability to cross the blood-brain barrier, consistent with its low permeability.
In terms of safety, PPGCA did not show hERG channel inhibitory activity, reducing the risk of cardiotoxicity. Ames trial results showed low genotoxicity, supporting its safety evaluation. Pharmacokinetics, existing research is limited, but preliminary data suggest that PPGCA has moderate metabolic stability and bioavailability in vivo. Its polar structure may lead to limited intestinal absorption, requiring optimized oral absorption and internal distribution through drug design.
Future research should focus on PPGCA's in vivo metabolic pathways, half-life, tissue distribution, and excretion mechanisms, combining pharmacokinetic approaches to improve its pharmacokinetic properties, such as nanocarrier encapsulation and structural modification, to enhance its clinical value.
As a natural product with multiple biological activities, PPGCA has broad clinical application prospects. Its remarkable anticancer activity makes it an important candidate for anti-tumor drug development, especially in combination chemotherapy and targeted therapy where synergistic effects may be achieved. Neuroprotective effects offer new approaches for treating neurodegenerative diseases, especially in fields where effective treatments are lacking, such as Parkinson's and Alzheimer's.
Moreover, PPGCA's anti-inflammatory and antioxidant properties give it potential application value in chronic inflammatory diseases and metabolic syndromes. Based on its natural origin and good safety, PPGCA is expected to be developed as a functional food or health supplement ingredient to promote health management and disease prevention.
However, clinical research on PPGCA is still in its early stages and lacks systematic clinical trial data. In the future, it is necessary to strengthen the evaluation of pharmacokinetics, toxicology, and clinical efficacy to improve the drug development chain. At the same time, by integrating modern drug design technologies, molecular structures and formulation forms are optimized to improve bioavailability and targetability, promoting the clinical translation of PPGCA.
Purpurogallin carboxylic acid, a natural phenolic compound derived from Macleaya microcarpa and fermented tea, exhibits abundant pharmacological activity, especially excelling in anticancer and neuroprotective fields. Its unique chemical structure gives it excellent druggability and safety, giving it the potential to become a candidate molecule for novel drugs. Although research on its mechanism of action and pharmacokinetics is still insufficient, existing research has laid a solid foundation for further exploration. In the future, through multidisciplinary collaboration combined with modern drug development technologies, PPGCA is expected to play an important role in the treatment of cancer and neurodegenerative diseases, promoting the development and innovation of natural product pharmacology.
