Synonym name: Cacticin
Catalogue No.: BP0797
Cas No.: 6743-92-6
Formula: C22H22O12
Mol Weight: 478.406
Botanical Source: Found in Cereus grandiflorus and others
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
Isorhamnetin-3-O-galactoside (CAS number: 6743-92-6) is an important flavonoid glycoside derivative widely present in various plants, especially in Oenanthe javanica, which is abundant. As the glycoside form of isorhamnetin, this compound not only maintains the typical biological activity of flavonoids, but also exhibits unique pharmacological properties due to the modification of sugar groups. In recent years, isorhamnetin 3-O-galactoside has become one of the hot natural products in the research of thrombotic diseases and related liver injury due to its significant anti thrombotic and pro fibrinolytic activities. This article will systematically review the chemical structure, physicochemical properties, plant sources, and extraction methods of isorhamnetin 3-O-galactoside, with a focus on its pharmacological activity, mechanism of action, drug evaluation, and clinical application prospects. The aim is to provide a theoretical basis and reference for its subsequent drug development and clinical application.
Isorhamnetin 3-O-galactoside belongs to the flavonoid glycoside class, with a molecular formula of C22H2O12 and a molecular weight of 478.4060. Its structure is composed of isorhamnetin (3 '- methoxyflavone) as a aglycone, which is connected to a galactoside bond through a 3-hydroxy group. This structure endows it with typical flavonoid skeleton features, including two aromatic rings (A, B rings) and one oxygen heterocyclic ring (C ring), as well as substitution of methoxy and hydroxyl groups, enhancing its biological activity and water solubility.
In terms of physicochemical properties, the LogP value of isorhamnetin 3-O-galactoside is approximately -0.0055, indicating its strong hydrophilicity and water solubility of 1.8289, which is consistent with the water solubility characteristics of flavonoid glycosides. Its topological polar surface area (TPSA) is 199.5100, and a higher polar surface area suggests a weaker ability to pass through cell membranes and a lower blood-brain barrier penetration ability. The negative result of hERG channel inhibition experiment indicates a low risk of cardiac toxicity. The Ames mutagenicity test score is 0.6, indicating that the genetic toxicity risk of this compound is relatively low and has a good safety basis.
Isorhamnetin 3-O-galactoside is mainly isolated from Oenanthe javanica. Water celery is a widely distributed aquatic or wetland plant in Asia, commonly used in traditional Chinese medicine for clearing heat, detoxifying, diuresis, and reducing swelling. Plants are rich in various flavonoids and their glycosides, among which isorhamnetin 3-O-galactoside has a higher content.
The extraction method usually uses alcohol extraction combined with chromatographic separation technology. The specific steps include:
In recent years, the introduction of supercritical CO2 extraction and membrane separation technology has provided new ideas for the efficient extraction of isorhamnetin 3-O-galactoside, improving extraction efficiency and purity.
The pharmacological activity research of isorhamnetin 3-O-galactoside mainly focuses on its anti thrombotic, pro fibrinolytic, and liver protective effects. In addition, its antioxidant and anti-inflammatory activities are gradually being studied.
Thrombosis is the pathological basis of various cardiovascular and cerebrovascular diseases, and regulating the activity of thrombin and factor Xa is a key target for antithrombotic therapy. Isorhamnetin 3-O-galactoside can significantly inhibit the activity of thrombin and factor Xa (FXa), reduce the maximum rate of fibrin polymerization catalyzed by thrombin, and thus inhibit thrombus formation. The mechanism also includes inhibiting FXa production and FVa/FXa mediated thrombin production, weakening the coagulation cascade reaction.
In addition, the compound can inhibit the secretion of plasminogen activator inhibitor-1 (PAI-1) induced by tumor necrosis factor - α (TNF - α), reduce the PAI-1/tissue type plasminogen activator (t-PA) ratio, promote fibrinolysis activity, improve hemorheological status, and further exert antithrombotic effects.
Isorhamnetin 3-O-galactoside exhibits significant protective effects in liver injury models. Using carbon tetrachloride (CCl4) - induced liver injury in mice as a model, studies have shown that this compound can alleviate liver cell necrosis, reduce serum transaminase levels, inhibit inflammatory reactions and oxidative stress, and promote liver tissue repair. Its liver protective effect is closely related to its antioxidant capacity, which can regulate the redox balance, reduce the generation of reactive oxygen species (ROS), and alleviate oxidative damage.
Isorhamnetin 3-O-galactoside activates the NFE2L2/NRF2 signaling pathway, upregulates the expression of antioxidant enzymes such as superoxide dismutase (SOD1, SOD2), catalase (CAT), glutathione peroxidase (GPX1), and heme oxygenase-1 (HMOX1), enhances the body's antioxidant defense ability, and reduces oxidative stress-induced cell damage.
Meanwhile, the compound can inhibit the expression of inflammatory factors, reduce the release of pro-inflammatory cytokines such as TNF - α and IL-6, regulate immune responses, and exert anti-inflammatory effects.
The mechanism of action of isorhamnetin 3-O-galactoside involves multiple signaling pathways and key molecular targets, mainly including:
Thrombin and factor Xa inhibition
By directly inhibiting the enzymatic activity of thrombin and factor Xa, blocking the coagulation cascade reaction, reducing fibrin formation, and preventing thrombus formation.
Adjusting the fibrinolytic system
Inhibit TNF - α - induced PAI-1 secretion, reduce PAI-1/t-PA ratio, promote fibrinolytic enzyme activity, and facilitate thrombolysis.
Activation of antioxidant signaling pathway
Activate NFE2L2/NRF2 transcription factors, promote the expression of antioxidant enzyme genes, eliminate excess reactive oxygen species, and protect cells from oxidative damage.
anti-inflammatory effect
Inhibit the expression of pro-inflammatory cytokines TNF - α and IL-6, alleviate inflammatory response, and protect tissue structure.
Liver protection mechanism
By synergistically targeting multiple targets, we can alleviate CCl4 induced liver cell damage and promote liver cell repair and regeneration.
In summary, isorhamnetin 3-O-galactoside exhibits promising therapeutic potential by synergistically regulating blood coagulation, fibrinolysis, oxidative stress, and inflammatory response through multiple targets and pathways.
The pharmacological evaluation of isorhamnetin 3-O-galactoside shows that it has good safety and pharmacological activity basis:
In terms of pharmacokinetics, existing research is relatively limited. Due to its good water solubility, oral absorption may be limited by the hydrolysis and metabolism of glycoside structures. Further in vivo pharmacokinetic studies are needed in the future to clarify its absorption, distribution, metabolism, and excretion characteristics, and optimize the dosing regimen.
Isorhamnetin 3-O-galactoside has shown broad clinical application prospects due to its multiple pharmacological activities such as antithrombotic, pro fibrinolytic, and hepatoprotective effects
Thrombotic vascular disease
It inhibits thrombin and factor Xa activity, regulates the fibrinolytic system, and is suitable for adjuvant therapy or prevention of thrombosis related diseases such as arteriosclerosis, venous thrombosis, and pulmonary embolism.
Liver injury and liver disease
It has a protective effect on CCl4 induced liver injury and can be extended to the treatment of liver diseases such as drug-induced liver injury, alcoholic liver disease, and non-alcoholic fatty liver disease in the future.
Antioxidant and anti-inflammatory diseases
Activating the NRF2 signaling pathway to alleviate oxidative stress and inflammatory response may have adjuvant therapeutic value for cardiovascular disease, metabolic syndrome, and chronic inflammatory diseases.
However, the clinical translation of isorhamnetin 3-O-galactoside still faces many challenges, including in vivo stability, oral bioavailability, formulation development, and systematic safety evaluation. In the future, pharmacokinetic, toxicological, and preclinical trial research should be strengthened to explore the potential for combination therapy and precise administration strategies.
As a natural flavonoid glycoside derived from Oenanthe javanica, isorhamnetin 3-O-galactoside has shown great potential in the fields of antithrombotic, fibrinolytic, and liver protection due to its unique chemical structure and multi-target pharmacological activity. It exerts multidimensional biological effects by inhibiting key coagulation factors, regulating the fibrinolytic system, activating antioxidant signaling pathways, and suppressing inflammatory responses. The drug efficacy evaluation shows that it has good safety, but its pharmacokinetic properties still need further research. In the future, with the help of modern drug development technology, isorhamnetin 3-O-galactoside is expected to become a new natural drug candidate molecule for the treatment of thrombotic diseases and liver injury related diseases. The elucidation of the pharmacological mechanism of the system and preclinical research will lay a solid foundation for its clinical translation and promote its in-depth development in the field of natural product pharmacology.
