Product name: Panaxydol
Synonym name: 9,10-Epoxy-1-heptadecene-4,6-diyn-3-ol
Catalogue No.: BP1657
Cas No.: 72800-72-7
Formula: C17H24O2
Mol Weight: 260.377
Botanical Source: Panax ginseng
Physical Description: Oil
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
The product could be supplied from milligrams to grams. Inquire for bulk scale.
We provide solution to improve the water-solubility of compounds, thereby facilitating the variety of activity tests and clinic uses.
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℃
32.7600
4.2170
4.2170
.0103
5.2129
8.6982
High
91.3444
4.2708
No
Yes
Yes
No
No
No
0.6
No
No
Yes
Yes
Natural products, as an important treasure trove for drug discovery and development, play an irreplaceable role in the long history of human fight against diseases. Ginseng（Panax ginseng C. A. Mey.）， As the "king of all herbs" in traditional medicine, its pharmacological activity goes far beyond its traditional nourishing and strengthening effects. Modern pharmacological research has revealed that ginseng is rich in a series of structurally unique and biologically active polyacetylene compounds, which are considered one of the key material foundations for ginseng to exert various pharmacological effects. Panaxydol, as a representative member of ginseng polyacetylene compounds, has attracted much attention due to its unique chemical structure, which combines epoxides, alkyne bonds, and alkene bonds. In recent years, with the deepening of research, ginseng epoxyacetylene alcohol has shown significant anti-tumor activity, especially in the treatment potential of gynecological malignancies such as ovarian cancer, becoming a research hotspot in the field of natural product pharmacology. This article aims to provide a systematic review of the chemical properties, plant sources, pharmacological activities, molecular mechanisms of action, pharmacological evaluation, and clinical application prospects of ginseng epoxyacetylene alcohol, in order to provide comprehensive scientific references for the in-depth research and development of this compound.
The chemical name of ginseng epoxyacetylene alcohol is (3R, 9R, 10S) -9,10-epoxyheptadecen-1-ene-4,6-diacetyl-3-ol, and its CAS number is 72800-72-7. Structurally, it is a straight chain aliphatic compound containing 17 carbon atoms, characterized by the presence of three key functional groups in its core skeleton: an epoxyethane structure (epoxide) located at C-9 and C-10 positions, a conjugated ene diyne system (C-1 to C-6 positions, containing one double bond and two triple bonds), and a hydroxyl group located at C-3 position. This structure, which combines highly reactive epoxy groups, linearly conjugated alkyne/ene systems, and hydrophilic hydroxyl groups, determines its unique physicochemical properties and biological activity.
Its molecular weight is 260.38 g/mol. The calculated lipid water partition coefficient (LogP) is 4.22, indicating that the compound has high lipophilicity. The topologically polar surface area (TPSA) is 32.76 Å ², which is relatively small due to the presence of only one hydroxyl group and one epoxy group in its molecule (contributing less). The predicted value of water solubility is relatively low, about 0.0103 mg/mL, which is consistent with the high LogP value, indicating that it has poor solubility in water and may be more soluble in organic solvents. These physical and chemical parameters collectively indicate its poor hydrophilicity and strong membrane permeability. The preliminary pharmacological prediction model shows that ginsenoside has a high blood-brain barrier permeability potential, which provides a structural basis for its application in the study of central nervous system related diseases. In addition, its hERG inhibition risk prediction is negative, and the preliminary Ames test result is 0.6 (usually considered to have mutagenic risk if>1.0), indicating that its cardiotoxicity and genotoxicity risks may be low, but further experimental verification is needed.
Ginseng epoxyacetylene mainly comes from plants of the Panax genus in the Araliaceae family, especially ginseng（Panax ginseng）Roots, rhizomes, and fibrous roots. In addition, in the same genus of plants, American ginseng（Panax quinquefolius）And Sanqi（Panax notoginseng）The presence of this compound or its analogues has also been found in the literature. In ginseng, polyacetylene compounds are not evenly distributed, and their content is often significantly affected by the place of origin, cultivation years, harvest season, and processing methods (such as fresh ginseng, white ginseng, and red ginseng). Research has shown that the content of these thermally unstable compounds is relatively high in fresh ginseng or low-temperature dried ginseng materials.
Organic solvent extraction is commonly used to extract epoxyacetylene alcohol from ginseng. Common solvents include methanol, ethanol, ethyl acetate, chloroform, etc. The typical extraction process is as follows: dry and crushed ginseng raw materials are extracted by cold soaking or heating reflux with an appropriate solvent (such as methanol), and the extracted liquids are combined and concentrated under reduced pressure to obtain the crude extract. Subsequently, purification was carried out using chromatographic separation techniques. Due to the sensitivity of polyacetylene compounds to light, heat, and oxygen, they are prone to polymerization or degradation. Therefore, the entire extraction and separation process needs to be carried out under low temperature, light avoidance, and inert gas protection (such as nitrogen). Preliminary enrichment is often carried out using silica gel column chromatography with gradient elution systems such as petroleum ether ethyl acetate or chloroform methanol for separation. Further purification relies on high-performance liquid chromatography (HPLC), especially a reverse phase C18 column, using methanol water or acetonitrile water as the mobile phase. In recent years, preparative chromatography techniques such as high-speed counter current chromatography (HSCCC) have also been applied to the separation and purification of epoxyacetylene alcohol in ginseng due to their high efficiency and avoidance of irreversible adsorption. The extraction rate is usually low and belongs to the trace active ingredients in ginseng, which partially explains its high research value and potential cost.
The pharmacological activity research of ginseng epoxyacetylene alcohol mainly focuses on the field of anti-tumor and exhibits various biological effects.
1. Antitumor activity
A large number of in vitro studies have confirmed that ginsenoside has significant proliferation inhibition and cytotoxic effects on various human tumor cell lines, with particular sensitivity to ovarian cancer cells. Research has shown that ginsenoside can dose dependently inhibit the viability of ovarian cancer cells such as SKOV3, A2780, OVCAR-3, induce cell cycle arrest (such as G1 phase or G2/M phase), and ultimately lead to cell apoptosis. In addition to ovarian cancer, it also has anti-tumor activity against colon cancer, lung cancer, breast cancer, neuroblastoma, melanoma and other cells, indicating that its effect has a certain broad-spectrum.
2. Inducing cell apoptosis and autophagy
Inducing tumor cell apoptosis is one of the core mechanisms by which ginsenosides exert anti-tumor effects. It can activate the caspase cascade through the mitochondrial pathway (endogenous pathway), leading to cell apoptosis. Meanwhile, studies have also observed that ginsenoside can induce cellular autophagy, which may serve as a pro survival mechanism in some cases and be associated with cell death in others. Its specific role may depend on cell type and drug concentration.
3. Anti angiogenic effect
The growth and metastasis of tumors depend on the formation of new blood vessels. Preliminary studies have shown that ginsenoside can inhibit the proliferation, migration, and tubular formation ability of human umbilical vein endothelial cells (HUVECs), and reduce the expression of vascular endothelial growth factor (VEGF), suggesting its potential for anti angiogenesis, which may help cut off the nutritional supply of tumors, inhibit their growth and metastasis.
4. Other activities
In addition, there are research reports on the potential activities of ginseng epoxyacetylene alcohol, such as antiplatelet aggregation, anti-inflammatory, and neuroprotective effects. However, there is relatively little research in these areas, and further exploration is needed.
The anti-tumor effect of ginseng epoxyacetylene alcohol involves a complex regulatory network of multiple targets and pathways, especially in ovarian cancer, and its mechanism of action has made certain progress in research. According to the provided target information, its mechanism of action can be summarized as follows:
1. Regulating apoptosis related proteins (BCL2)
BCL2 family proteins are the core regulators of mitochondrial apoptosis pathways. Ginsenoside epoxypyrinol can downregulate the expression of anti apoptotic protein BCL2, disrupt the balance of BCL2/BAX ratio, promote increased mitochondrial outer membrane permeability, release cytochrome C, and thus initiate caspase dependent apoptosis program.
2. Inhibit the STAT3 signaling pathway
Signal transducer and activator of transcription factor 3 (STAT3) is an important oncogenic transcription factor that is continuously activated in ovarian cancer, promoting cell proliferation, survival, and immune escape. Ginseng epoxyacetylene alcohol has been shown to inhibit the phosphorylation (activation) of STAT3, suppress its nuclear translocation, and inhibit the transcription of downstream target genes (such as Cyclin D1, BCL2, Survivor), thereby inhibiting tumor growth.
3. Inducing oxidative stress and activating the NRF2 pathway
The highly reactive enynes and epoxy groups in the structure of ginseng epoxyacetylene alcohol may participate in intracellular redox reactions, inducing the generation of reactive oxygen species (ROS). Moderate ROS outbreaks can lead to oxidative stress and damage to tumor cells. Meanwhile, as a key regulatory factor of cellular antioxidant response, nuclear factor E2 related factor 2 (NRFE2L2/NRF2) may be activated, which is an adaptive response of cells to combat oxidative stress. In tumors, sustained activation of NRF2 can sometimes be beneficial for the survival of tumor cells. Therefore, the regulation of NRF2 pathway by ginsenoside epoxide has a dual nature and needs to be analyzed in specific environments.
4. Affects drug efflux pump (ABCB1)
ABCB1 (P-glycoprotein) is the main efflux pump mediating multidrug resistance (MDR). There are studies suggesting that ginsenoside may have the potential to regulate the function or expression of ABCB1, or reverse chemotherapy resistance caused by ABCB1 overexpression. This provides a theoretical basis for combining it with conventional chemotherapy drugs to overcome resistance.
5. Interference with DNA topoisomerase function (TOP1, TOP2A) and repair enzyme (TDP1)
DNA topoisomerases I (TOP1) and II α (TOP2A) are key enzymes involved in DNA replication and transcription, and are also targets of various chemotherapy drugs. Panax glycidol may cause DNA damage accumulation by interfering with the function of these enzymes. In addition, tyrosyl DNA phosphodiesterase 1 (TDP1) is a key enzyme for repairing TOP1-DNA complex damage. Targeting TDP1 can enhance the efficacy of TOP1 inhibitors. The potential effects of ginseng epoxyacetylene alcohol on TOP1, TOP2A, and TDP1 suggest that it may kill tumor cells by directly or indirectly affecting DNA integrity and repair processes.
6. Regulating the MAPK/ERK signaling pathway (MAPK1)
MAPK1 (ERK2) is a core member of the MAPK/ERK signaling pathway, involved in cell proliferation, differentiation, and survival. Ginseng epoxyacetylene alcohol may inhibit tumor cell growth by regulating the activity of this pathway and affecting the function of downstream transcription factors.
7. Interactions with other targets
Panax oxyalkynol may also play a role by inhibiting tyrosinase (TYR, which is related to melanin synthesis, and may affect some melanoma cells), regulating estrogen receptor alpha (ESR1, which is related to hormone dependent tumors, such as some breast cancer and ovarian cancer), etc. These targets together form a complex network that explains their pleiotropic pharmacological effects.
Although ginseng epoxyacetylene alcohol exhibits excellent anti-tumor activity in vitro, its drug like and pharmacokinetic properties are the key bottlenecks determining its successful development as a drug.
1. Analysis of drug properties
As mentioned earlier, ginseng epoxyacetylene alcohol has the characteristics of high lipophilicity (LogP>4) and low water solubility. Although this is beneficial for its penetration through the cell membrane, it can lead to poor oral absorption, low bioavailability, and easy accumulation in the body. Its smaller TPSA and predicted high blood-brain barrier permeability provide possibilities for its application in brain tumors, but may also increase the potential risk of side effects in the central nervous system. HERG inhibition reduces the risk of causing QT interval prolongation in the heart, but experimental confirmation is needed. The preliminary data from Ames test suggests a low risk of genetic toxicity, but a complete combination of genetic toxicity tests (such as micronucleus test, chromosome aberration test) is still needed for comprehensive evaluation.
2. Pharmacokinetic challenges
At present, there are relatively few reports on the in vivo pharmacokinetic studies of the ginseng epoxy alkyne alcohol system, which is the main knowledge gap in the development of this compound. Based on its physicochemical properties, it can be foreseen that oral administration may face significant first pass effects and irregular absorption. In the body, its highly reactive epoxy and enyne structures may make it easy to bind with nucleophilic substances such as glutathione (GSH) or be metabolized by the cytochrome P450 enzyme system (CYP450), resulting in rapid clearance and short half-life. Its metabolites may have activity or toxicity and require clear identification. In addition, high lipophilicity may lead to a large distribution volume, mainly distributed in adipose tissue, and the effective concentration reaching target organs (such as ovarian tumors) may be insufficient.
3. Formulation strategy
In order to overcome its drug defects, modern drug delivery technology is particularly important. Possible strategies include: ① Prodrug design Preparation of water-soluble prodrugs through chemical modification (such as esterification of hydroxyl groups) to improve absorption and distribution. ② Nano delivery system Encapsulating it in liposomes, polymer nanoparticles, micelles, or albumin nanoparticles can significantly improve its water solubility, prolong circulation time, enhance tumor targeting (through EPR effect or active targeting modification), and reduce systemic toxicity. ③ Eutectic/Eutectic Amorphous Technology Prepare eutectic or amorphous solid dispersions with suitable co morphs to improve solubility and dissolution rate.
Ginseng epoxyacetylene alcohol, as a natural compound with unique structure and multi-target anti-tumor activity, has broad clinical application prospects, but the road is long and full of challenges.
1. As a candidate drug for ovarian cancer treatment
Ovarian cancer has the highest mortality rate among gynecological malignancies, and chemotherapy resistance is the main reason for treatment failure. The high sensitivity, induction of apoptosis, inhibition of STAT3 pathway, and potential reversal of ABCB1 mediated drug resistance of ginseng epoxypyrinol to ovarian cancer cells make it an attractive candidate molecule for the development of novel anti ovarian cancer drugs, especially for the treatment of drug-resistant or recurrent ovarian cancer. The combination therapy of it with existing chemotherapy drugs (such as platinum, paclitaxel) or targeted drugs deserves further research.
2. Combination therapy and sensitizers
Given its multi-target nature, ginsenoside may not only be used as a monotherapy, but also as a sensitizer for chemotherapy or radiotherapy. By interfering with DNA repair (such as inhibiting TDP1), inducing oxidative stress, or inhibiting pro survival signaling pathways (such as STAT3), it may reduce the dosage required for traditional therapies, thereby alleviating side effects and overcoming or delaying the development of drug resistance.
3. Precise treatment based on a new delivery system
One of the key focuses of future research is to combine ginseng epoxyacetylene alcohol with modern nanomedicine. Developing tumor targeted nano formulations can achieve controlled drug release, increase local drug concentration in tumors, reduce toxicity to normal tissues, thereby maximizing their pharmacological potential and improving their adverse pharmacokinetic properties.
4. Challenges and Future Directions Faced
First,Preclinical research of the system Urgent improvement: Comprehensive in vivo pharmacological evaluation (to validate efficacy in different ovarian cancer animal models, especially patient derived xenograft models), detailed pharmacokinetic/toxicokinetic studies, and safety evaluations of acute/subacute toxicity, genetic toxicity, reproductive toxicity, etc. that meet drug registration requirements are needed. Secondly,The mechanism of action needs to be further deepened Although multiple targets are known, the interaction network between these targets, their most critical effector targets, and their roles in the tumor microenvironment are still unclear. Using chemical and biological methods, such as designing active probes, to search for proteins that directly interact with it will help reveal its original mechanism of action. Finally,Stability of compounds and large-scale preparation How to achieve efficient, stable, and large-scale green preparation of ginseng epoxyacetylene alcohol is also a problem that must be solved for its industrialization. Synthetic biology or total chemical synthesis may be feasible alternatives to plant extraction.
Ginseng epoxyacetylene alcohol, as a structurally unique polyacetylene compound in ginseng, has become a highlight in the research of natural anti-tumor drugs due to its significant in vitro anti-tumor activity, especially its multi-target mechanism of action against ovarian cancer. It induces tumor cell apoptosis and demonstrates the potential to overcome chemotherapy resistance by regulating multiple key targets and pathways such as BCL2, STAT3, DNA topoisomerase and related repair enzymes, MAPK, etc. However, its inherent high lipophilicity, low water solubility, and unclear pharmacokinetic and systemic toxicity characteristics in vivo pose important obstacles to its clinical translation. In the future, through in-depth mechanism exploration, rational structural optimization, and especially the development of new formulations with advanced drug delivery technology, it is expected to overcome these bottlenecks and fully unleash the therapeutic potential of ginsenoside epoxide. By deeply integrating the wisdom of traditional Chinese medicine with modern science and technology, ginsenoside epoxyacetylene alcohol is expected to provide important lead compounds and new strategies for the development of highly efficient and low toxicity anti ovarian cancer drugs, ultimately benefiting patients worldwide.
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