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Product name: Eugenin
Synonym name: Tellimagrandin II
Catalogue No.: BP4713
Cas No.: 81571-72-4
Formula: C41H30O26
Mol Weight: 938.665
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℃
444.1800
1.8158
1.8162
.0028
.9155
.4720
Low
85.5730
5.5893
Yes
Yes
Yes
No
Yes
No
0.6
Yes
No
Yes
No
Natural products, as important resources for drug discovery, attract much attention for their structural diversity and biological activity. Eugenin is a chromone natural compound isolated from Formosan Peucedanum japonicum, a plant endemic to Taiwan. In recent years, it has attracted widespread research interest due to its remarkable antiplatelet aggregation activity and cytotoxicity to tumor cells. As the issue of antimicrobial resistance becomes increasingly severe, the potential application value of t-bud tannin in the field of antimicrobial therapy is gradually being revealed, especially its effects on various bacterial and fungal targets, providing a theoretical foundation for the development of novel anti-infective drugs.
This review aims to systematically summarize the chemical structure and physicochemical properties of Dingzi bud tannin, plant origin, and extraction methods, thoroughly explore its pharmacological activity and molecular mechanisms, conduct pharmacokinetic analysis combined with druggability parameters, evaluate its clinical application prospects, and look ahead to future research directions. By comprehensively reviewing relevant literature, it is hoped that scientific evidence and reference will be provided for the drug development and clinical application of dingziya tannin.
Eugenin has a relatively complex molecular formula, with a molecular weight of 938.6650, belonging to the chromotone compounds. Its structural core is a typical chromone backbone, containing multiple phenolic hydroxyl and ester groups, which impart strong biological activity. In terms of physicochemical properties, the LogP value of t-tina tannin is 1.8158, indicating moderate lipid solubility that facilitates cell membrane penetration; its high polar surface area (TPSA) reaches 444.18 Ų, indicating strong polarity and hydrogen bond donor/acceptor capacity, which may affect its bioavailability and intracellular distribution.
Low water solubility (0.0028 mg/mL) limits its solubility in aqueous media, suggesting that methods to improve solubility should be considered in drug formulation design. Low blood-brain barrier permeability indicates that butin tannin has difficulty entering the central nervous system, reducing the risk of CNS toxicity. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test value was 0.6, indicating a low genotoxicity risk and good safety potential.
Dingziya tannin is mainly isolated from Formosan Peucedanum japonicum, a plant endemic to Taiwan. This plant belongs to the Apipulaceae family and has traditionally been used in folk medicine, possessing anti-inflammatory and antibacterial pharmacological activities. The extraction of t-bud tannin usually uses organic solvent extraction combined with column chromatography separation technology.
The specific steps include: first, cold soak or reflux extraction of dried plant herbs or rhizomes using ethanol or methanol, followed by vacuum concentration to obtain the crude extract. The crude extract was separated by silica gel column chromatography, and components of different polarities were separated using gradient elution. Further purification uses high-performance liquid chromatography (HPLC) technology, combined with mass spectrometry and nuclear magnetic resonance (NMR) to confirm the structure. In recent years, ultrasound-assisted extraction and supercritical fluid extraction technologies have also been applied to improve the extraction efficiency and purity of tinybud tannin.
Dingziya tannin was first reported to exhibit significant antiplatelet aggregation activity. Platelets play a key role in hemostasis and thrombosis, and their abnormal activation is the pathological basis for various cardiovascular and cerebrovascular diseases. Tin-bud tannin can effectively inhibit platelet factor-induced aggregation reactions, demonstrating potential antithrombotic risk prevention effects. Relevant in vitro experiments show that butinin blocks platelet aggregation signaling pathways by regulating intraplatelet calcium ion concentration and inhibiting platelet membrane receptor activity.
Binary tannin exhibits certain cytotoxicity against various tumor cell lines, especially its inhibitory effect on lung, breast, and liver cancer cells. Its mechanism involves inducing tumor cell apoptosis, blocking the cell cycle, and inhibiting cell migration and invasion. In vitro cell experiments and some animal model studies have confirmed that tin-bud tannin can promote tumor cell apoptosis by activating mitochondrial pathways and regulating apoptosis-related protein expression.
T-bud tannin also demonstrates broad-spectrum activity in the antibacterial field, inhibiting Gram-positive bacteria, Gram-negative bacteria, and fungi. Its targets include key enzymes such as bacterial DNA gyrase (GYRA), cell wall synthase (FABI), and dihydrofolate reductase (DHFR), as well as fungal enzymes like ERG11 and CYP51A1, demonstrating its multi-target inhibitory properties. This multi-target mechanism helps reduce the risk of resistance development.
The multiple pharmacological activities of tin-bud tannin are closely related to its action on various molecular targets.
Anti-platelet aggregation mechanism
Binary tannin blocks the binding between platelets and fibrinogen by inhibiting glycoprotein receptor activity (such as GPIIb/IIIa) on platelet membranes, thereby suppressing platelet aggregation. Additionally, it can regulate signaling pathways within platelets, such as inhibiting the activities of phosphatidylinositol 3-kinase (PI3K) and protein kinase C (PKC), reducing intracellular calcium ion concentration, and blocking platelet activation.
Antitumor mechanism
Cytin-induced tumor cell apoptosis mainly activates the caspase enzyme system via mitochondrial-dependent pathways, regulates the expression of Bcl-2 family proteins, and promotes apoptosis. Additionally, it can block the tumor cell cycle, especially during the G1 and G2/M phases, inhibiting cell proliferation. T-tinin also affects tumor cell migration and invasion capabilities, possibly by regulating matrix metalloproteinase (MMPs) expression.
Antibacterial mechanism
Tintinin targets key enzymes such as bacterial DNA gyrase (GYRA) and cell wall synthase (FABI), interfering with bacterial DNA replication and cell wall synthesis, which leads to inhibited bacterial growth. For fungi, butina tannin inhibits ERG11 and CYP51A1 enzyme activity, blocks ergosterol biosynthesis, and damages the integrity of fungal cell membranes. Additionally, t-bud tannin can inhibit fungal drug efflux pumps (such as CDR1), enhancing the efficacy of antifungal drugs.
The druggability parameters of t-tin tannin indicate that it has certain potential for drug development. A larger molecular weight (938.6650) may affect oral absorption, but a moderate LogP value (1.8158) favors cell membrane penetration. A higher TPSA (444.18 Ų) suggests strong polarity, which may limit passive diffusion absorption. Low water solubility (0.0028 mg/mL) is a major challenge in its development, requiring optimization of the drug formulation to improve bioavailability.
The blood-brain barrier has low permeability, reducing the risk of central nervous system side effects. A negative hERG channel inhibition indicates good cardiac safety. Ames test results showed a low genotoxicity risk and met safety requirements.
Pharmacokinetics, current research on the absorption, distribution, metabolism, and excretion (ADME) of tintin in vivo is relatively limited. Preliminary animal experiments show that its oral bioavailability is limited, its in vivo half-life is moderate, and it is mainly metabolized through the hepatic enzyme system. In the future, systematic pharmacokinetic and toxicological studies are needed to further improve clinical development data.
Due to its unique antiplatelet aggregation and antitumor activity, Dingziya tannin has the potential to become an adjunctive therapy for cardiovascular and cerebrovascular diseases and as an anticancer drug. Its multi-target antibacterial action offers new ideas for addressing resistance issues, especially in the treatment of multidrug-resistant bacterial and fungal infections, which may lead to breakthroughs.
However, the clinical application of dingziya tannin still faces many challenges. First, low water solubility and bioavailability limit the development of oral formulations, which require improvements through technologies such as nanocarriers, liposomes, or solid dispersions. Second, there is a lack of systematic preclinical safety and pharmacokinetic data, and there is an urgent need for relevant studies to assess the safety and effective dosage range of long-term medication. Third, large molecular weight and strong polarity may affect its distribution in vivo, limiting drug concentrations at certain disease sites to therapeutic levels.
Future research should focus on:
1. Optimize extraction and synthesis processes to increase yield and purity;
2. Structural modification and drug carrier design to improve drug solubility and bioavailability;
3. In-depth analysis of mechanisms of action, clarification of key molecular targets and signaling pathways;
4. Expand in vivo and in vitro pharmacodynamics and safety evaluations to advance preclinical research;
5. Explore combination drug strategies to enhance antitumor and antibacterial efficacy.
As a natural chromoketone compound with multiple biological activities, t-tiny tannin demonstrates pharmacological potential in areas such as anti-platelet aggregation, anti-tumor, and broad-spectrum antibacterial properties. Its unique mechanism of action and relatively good safety provide valuable candidate molecules for the development of natural product drugs. However, limitations in druggability and shortcomings in preclinical research still require further overhaul. With advances in modern medicinal chemistry, pharmaceutics, and molecular biology technologies, tin-bud tannin is expected to achieve clinical translation through structural optimization and formulation innovation, becoming a novel drug for treating cardiovascular diseases, tumors, and infectious diseases.
Future research should strengthen multidisciplinary collaboration, systematically evaluate the pharmacodynamics, safety, and pharmacokinetic characteristics of tin-a-bud tannin, promote its transition from the laboratory to clinical application, and contribute new therapeutic options to public health.
Shenshuai
Wenjing
Hedandan
