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Product name: Rhamnetin-3-O-β-D-Glucoside
Synonym name: Rhamnetin 3-O-glucoside；Rhamnetin 3-glucoside
Catalogue No.: BP2270
Cas No.: 27875-34-9
Formula: C22H22O12
Mol Weight: 478.406
Botanical Source:
Type of Compound: Flavonoids
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.
HPLC of Rhamnetin-3-O-β-D-Glucoside
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
199.5100
.2106
.1748
1.3512
.5575
.2871
Low
77.7023
3.9582
Yes
No
No
No
Yes
No
0.6
Yes
No
Yes
No
Rhamnetin-3-O-glucoside (Rhamnetin-3-O-β-D-Glucoside, hereinafter referred to as Rhamnetin-3-G) is a natural flavonoid compound belonging to the flavonoid glycoside. As an important member of the flavonoid family, Rhamnetin-3-G has attracted widespread attention in recent years due to its remarkable bioactivity, especially its potential in antioxidant fields. Antioxidant capacity is a hot topic in pharmacological research of natural products, as it is closely related to various chronic diseases such as cardiovascular diseases, neurodegenerative diseases, inflammation, and tumors. This paper aims to systematically review the chemical structure and physicochemical properties of Rhamnetin-3-G, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and finally explore its clinical application prospects and future research directions.
Rhamnetin-3-G has the molecular formula C22H22O12, molecular weight 478.4060, and CAS number 27875-34-9. Its structural core is rhamnetin, which is 7-hydroxy-3',4',5-trimethoxyflavonol, with three hydroxyl positions modified by β-D-glucosylation. This glycosylation modification significantly affects its water solubility, bioavailability, and pharmacological activity.
In terms of physicochemical properties, Rhamnetin-3-G has a LogP value of 0.2106, indicating low lipid solubility and a tendency toward aqueous phase distribution. The polar surface area (TPSA) reaches as high as 199.51 Ų, indicating strong polarity, which is favorable for water solubility and the formation of intermolecular hydrogen bonds. The water solubility index is 1.3512, indicating good solubility in water. The blood-brain barrier has low permeability, suggesting that its direct effect in the central nervous system may be limited. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames mutagenicity test scored 0.6, indicating a low genotoxicity risk and a certain level of safety.
Rhamnetin-3-G is widely found in various plants, especially Rhamnus species and some legumes and rhododendrons. Common plants rich in this compound include Rhamnus cathartica, purple rhamnus (Rhamnus purshiana), and certain Chinese medicinal materials such as Scutellaria species.
The extraction method mostly uses solvent extraction combined with chromatography separation technology. Generally, ethanol or methanol aqueous solutions are used as extractors, and crude extracts are obtained by ultrasound-assisted extraction or reflux extraction. Subsequently, liquid-liquid partitioning, silica gel column chromatography, and reversed-phase high-performance liquid chromatography (RP-HPLC) were used for purification and separation. In recent years, green extraction technologies such as supercritical fluid extraction (SFE) and microwave-assisted extraction (MAE) have gradually been applied to efficiently extract these flavonoid glycosides, significantly improving extraction efficiency and purity.
The main pharmacological activity of Rhamnetin-3-G is concentrated in the antioxidant field. Numerous in vitro experiments have shown that this compound can effectively eliminate free radicals, inhibit lipid peroxidation, and protect cells from oxidative stress damage. Its antioxidant activity is achieved by enhancing the expression and activity of endogenous antioxidant enzyme systems (such as superoxide dismutase SOD, catalase CAT, glutathione peroxidase GPX1, etc.).
Oxidative stress is closely related to inflammatory responses. Rhamnetin-3-G demonstrates significant anti-inflammatory effects by regulating the expression of nuclear factor NF-κB and related inflammatory factors. Animal model studies show that this compound can reduce damage to inflamed tissues and lower levels of pro-inflammatory cytokines such as TNF-α and IL-6.
Some studies have revealed that Rhamnetin-3-G inhibits proliferation and induces apoptosis in various tumor cells. Its mechanism may involve regulating cyclins, activating apoptosis-related signaling pathways, and inhibiting the activity of tumor-related matrix metalloproteinases (MMP1, MMP3), thereby blocking tumor cell invasion and metastasis.
Although the blood-brain barrier permeability is relatively low, Rhamnetin-3-G demonstrates certain neuroprotective potential by regulating peripheral antioxidant enzyme expression in the central nervous system and reducing neuroinflammation, making it promising for adjunctive treatment of neurodegenerative diseases.
The antioxidant mechanism of Rhamnetin-3-G mainly relies on its regulation of multiple key targets:
NFE2L2/NRF2 signaling pathway: Rhamnetin-3-G can activate nuclear factor E2-related factor 2 (NFE2L2, also known as NRF2), promoting gene expression mediated by antioxidant response elements (ARE), enhancing the expression of intracellular antioxidant enzymes such as SOD1, SOD2, CAT, GPX1, and HMOX1, thereby improving cellular antioxidant capacity.
Metaloproteinase inhibition: By inhibiting the activity of matrix metalloproteinases MMP1 and MMP3, Rhamnetin-3-G slows extracellular matrix degradation, preventing inflammation and tumor cell invasion and spread.
Tyrosinase (TYR) regulation: This target involves melanin synthesis and oxidative stress responses. Rhamnetin-3-G's regulation of TYR helps exert antioxidant and anti-inflammatory effects.
Anti-inflammatory signaling pathways: By inhibiting NF-κB and MAPK signaling pathways, it reduces the release of pro-inflammatory factors and alleviates inflammatory responses.
In summary, Rhamnetin-3-G exerts broad biological effects through multi-target and multi-pathway synergistic effects.
The druggability parameters of Rhamnetin-3-G indicate that it has certain potential for drug development. Although the molecular weight of 478.4 is slightly above the ideal range, it is still within an acceptable range. Low LogP values and high TPSA suggest good water solubility, which is beneficial for dissolution and absorption of oral formulations, but may also limit cell membrane penetration, especially through the blood-brain barrier.
The low permeability of the blood-brain barrier suggests limited direct efficacy on the central nervous system, but may exert indirect neuroprotective effects by modulating peripheral systems. The negative and low mutagenicity of hERG channel inhibition (Ames test 0.6) indicates good safety and low risks of cardiotoxicity and genotoxicity.
Currently, pharmacokinetic research on Rhamnetin-3-G is relatively limited. Preliminary data indicate that its oral absorption rate is moderate, metabolism in the body mainly occurs via the hepatic phase II metabolism pathway (such as glucuronylation and sulfation), and excretion is primarily via the kidneys and bile. Future studies require further systematic evaluation of its bioavailability, metabolic stability, and in vivo distribution characteristics.
Given Rhamnetin-3-G's excellent antioxidant and anti-inflammatory activities, it has broad application prospects in chronic disease prevention and treatment. Especially in cardiovascular diseases, diabetes complications, neurodegenerative diseases, and tumor adjuvant therapy, Rhamnetin-3-G is expected to play a positive role as a natural drug or functional health supplement ingredient.
Future clinical translation should focus on addressing the following issues:
Dosage form development and delivery route optimization: Improving bioavailability, improving oral absorption, and exploring novel delivery systems such as nanocarriers and liposomes.
Systematic pharmacokinetics and safety evaluation: Conduct systematic toxicology studies and long-term safety assessments to clarify metabolites and potential drug interactions.
Clinical trial design: Based on its multi-target mechanism of action, design clinical trials targeting specific diseases to verify efficacy and safety.
Structural modification and derivative development: Chemical modification enhances the penetration and targeting of the blood-brain barrier, expanding its application in neurological diseases.
Rhamnoside-3-O-glucoside, as a natural flavonoid glycoside with significant antioxidant and anti-inflammatory activities, demonstrates excellent pharmacological properties and safety. Its multi-target and multi-mechanism mode of action provides both theoretical and practical basis for the development of novel natural drugs. Although research on its pharmacokinetics and clinical applications is still in its early stages, with advances in extraction techniques and drug delivery systems, Rhamnetin-3-G is expected to become an important candidate for antioxidant and related disease therapies. Future research should focus on further elucidating its mechanism of action, optimizing drug properties, and promoting clinical translation, aiming to achieve its widespread application in modern medicine.
Shenshuai
Wenjing
Hedandan
