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Product name: 2-(3,4-dihydroxyphenyl)-7-(β-D-glucopyranosyloxy)-8-hydroxy-4H-1-benzopyran-4-one
Synonym name:
Catalogue No.: BP5095
Cas No.: 925701-05-9
Formula: C21H20O11
Mol Weight: 448.38
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.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
190.2800
-.0125
-.0580
1.0241
.6052
.2023
Low
78.1321
3.9448
Yes
No
No
No
Yes
No
1.2
Yes
No
Yes
Yes
With the continuous deepening of modern medicine's research into the pharmacological activity of natural products, flavonoids, due to their diverse biological activities and relatively low toxic side effects, have become an important direction in the development of natural medicines. 3',4',8-trihydroxyflavone-7-O-β-D-glucoside (2-(3,4-dihydroxyphenyl)-7-(β-D-glucopyranosyloxy)-8-hydroxy-4H-1-benzopyran-4-one, hereinafter referred to as "trihydroxyflavone glucoside"), as a flavonoid glycoside with a unique structure, is characterized by its significant antioxidant activity and potential pharmacological effects. It has gradually attracted widespread attention in the fields of pharmacology and medicinal chemistry. This paper aims to systematically review the chemical structure and physicochemical properties of this compound, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics. In light of current research progress, it explores its clinical application prospects and future development directions.
The chemical structure of 3',4',8-trihydroxyflavone-7-O-β-D-glucoside consists of aglycone and glucosides, specifically 2-(3,4-dihydroxyphenyl)-7-(β-D-pyranglucooxy)-8-hydroxy-4H-1-benzopyran-4-one. This structure contains three hydroxyl sites (positions 3', 4', and 8) and a 7-O-β-D-glucosidic bond, giving it strong hydrophilicity and bioactivity.
In terms of physicochemical properties, the molecular weight of this compound is 448.38 Da, making it a medium-weight flavonoid glycoside. The LogP value is -0.0125, indicating strong hydrophilicity, and water solubility is 1.0241, indicating good solubility in aqueous media. TPSA (topological polar surface area) is 190.28 Ų. Higher polar surface area is usually associated with poorer cell membrane permeability, and its lower blood-brain barrier permeability suggests difficulty penetrating the central nervous system. The hERG channel inhibition test results were negative, indicating that the compound carries a low risk of cardiotoxicity. The Ames-induced mutagenic test value was 1.2, indicating a low genotoxicity risk and a solid safety foundation.
3',4',8-trihydroxyflavone-7-O-β-D-glucoside is mainly found in several traditional Chinese medicinal plants, especially those rich in flavonoids such as mulberry leaf (Morus alba), ginkgo leaf (Ginkgo biloba), and some plants in the Rhododendron family. Although its content is not as abundant as mainstream flavonoid glycosides, its unique hydroxyl group distribution and glycoside structure make it a key research focus.
The extraction method typically uses organic solvent extraction combined with column chromatography purification technology. Common extraction solvents include ethanol, water, or their mixed solvent systems, which improve extraction efficiency through ultrasound-assisted extraction or reflux extraction. After concentration and liquid-liquid distribution, the extract was separated and purified using silica gel column chromatography and reversed-phase high-performance liquid chromatography (RP-HPLC). Purity testing mostly uses HPLC-UV and mass spectrometry (LC-MS) technology to ensure the acquisition of high-purity target compounds.
The most notable pharmacological activity of 3',4',8-trihydroxyflavone-7-O-β-D-glucoside is its strong antioxidant capacity. In vitro DPPH radical scavenging experiments, ABTS radical scavenging tests, and hydroxyl radical scavenging tests all demonstrate excellent free radical scavenging capabilities. Its polyhydroxyl structure acts as an electron donor, effectively trapping free radicals and slowing down oxidation chain reactions.
This compound demonstrated significant anti-inflammatory effects across various inflammation models. By suppressing the expression of pro-inflammatory factors such as TNF-α and IL-6, and reducing the activity of inflammation-related enzymes (such as COX-2 and iNOS), the inflammatory response is reduced. Its anti-inflammatory mechanism is closely related to its antioxidant activity, which can alleviate the inflammatory cascade induced by oxidative stress.
In cell models, 3',4',8-trihydroxyflavone glucoside can protect cells from apoptosis induced by oxidative damage. By regulating the intracellular antioxidant enzyme system, it enhances cellular antioxidant defenses, reduces ROS levels, maintains mitochondrial function stability, and lowers apoptosis rates.
Although this compound has a low blood-brain barrier permeability, it demonstrates certain neuroprotective effects in in vitro neuronal cell models, possibly by activating intracellular antioxidant pathways to alleviate oxidative stress-related nerve damage. Moreover, its antioxidant and anti-inflammatory properties offer potential value for cardiovascular disease prevention and treatment, such as reducing oxidative damage to myocardial cells and inhibiting the progression of atherosclerosis.
The main mechanism of action of 3',4',8-trihydroxyflavone-7-O-β-D-glucoside focuses on regulating the intracellular antioxidant defense system. Key targets include:
NFE2L2 (NRF2): This compound activates the NRF2 signaling pathway, promoting the transfer of NRF2 from the cytoplasm to the nucleus and enhancing gene expression mediated by antioxidant response elements (ARE). After NRF2 activation, downstream antioxidant enzymes such as SOD1, SOD2, CAT, GPX1, and HMOX1 are upregulated, significantly enhancing cellular antioxidant capacity.
Superoxide dismutase (SOD1, SOD2): By promoting SOD enzyme activity, it catalyzes the disproportionation of superoxide anion radicals into hydrogen peroxide, reducing cell damage caused by free radicals.
Catalase (CAT): accelerates the breakdown of hydrogen peroxide into water and oxygen, further reducing oxidative stress levels.
Glutathione peroxidase (GPX1): catalyzes the reduction of organic peroxides, protecting cell membrane lipids from peroxidative damage.
Hemoglobin oxygenase-1 (HMOX1): Produces antioxidant products by degrading heme and participates in cell protection.
Additionally, 3',4',8-trihydroxyflavone glucoside may also exert dual anti-inflammatory and antioxidant effects by regulating inflammation-related signaling pathways such as NF-κB, reducing cell damage caused by oxidative stress.
From a druggability perspective, the compound has a moderate molecular weight (448.38 Da), which fits the Lipinski rule molecular weight range. However, its relatively high TPSA (190.28 Ų) and polar hydroxyl and glycoside structures limit its cell membrane permeability, especially its low blood-brain barrier penetration ability, which may restrict its central nervous system applications.
Its LogP value is close to zero, indicating strong hydrophilicity, which is beneficial for the development of water-soluble formulations but may also affect oral bioavailability. Good water solubility (1.0241), which is beneficial for formulation design and in vivo distribution.
In terms of safety, the hERG channel inhibition test was negative, reducing the risk of cardiotoxicity. Ames-induced mutagenicity results showed low mutagenicity and good safety.
Currently, pharmacokinetic data on this compound are limited. Preliminary in vitro metabolic studies suggest it may be metabolized via hepatic enzyme systems, with some glycosides possibly hydrolyzed under gut microbiota to release active flavonoid aglycosides. Future research on in vivo pharmacokinetics is needed to clarify its absorption, distribution, metabolism, and excretion (ADME) characteristics.
Based on their significant antioxidant and anti-inflammatory activities, 3',4',8-trihydroxyflavone-7-O-β-D-glucoside has potential clinical value in various oxidative stress-related diseases. Including but not limited to:
Chronic inflammatory diseases: such as rheumatoid arthritis and inflammatory bowel disease, which alleviate pathological progression by inhibiting inflammatory mediators and oxidative damage.
Cardiovascular diseases: Prevents and treats atherosclerosis, myocardial ischemia-reperfusion injury, and protects myocardial cells.
Neurodegenerative diseases: Although the blood-brain barrier penetration is low, structural modification or nanocarrier delivery is expected to enhance the efficacy of central nervous system drugs, applied in Alzheimer's disease, Parkinson's disease, and others.
Skin diseases and anti-aging: Utilizing its antioxidant properties, topical formulations are developed to prevent and treat UV-induced skin damage.
Future research should focus on in vivo pharmacokinetic optimization, structural modification to improve bioavailability, and the development of targeted delivery technologies. At the same time, systematic toxicological evaluations and preclinical pharmacodynamic studies are being carried out to lay the foundation for clinical translation.
3',4',8-trihydroxyflavone-7-O-β-D-glucoside, a structurally unique flavonoid glycoside natural product, demonstrates broad research and application prospects in the field of natural product pharmacology due to its excellent antioxidant and anti-inflammatory activities. By activating the NRF2 signaling pathway and regulating the expression of various antioxidant enzymes, it exerts a cell-protective effect, offering good safety and drug potential. In the future, by integrating modern medicinal chemistry and formulation technologies, in-depth pharmacokinetics and preclinical research are expected to promote clinical application and become a novel candidate drug for treating diseases related to antioxidant damage.
Shenshuai
Wenjing
Hedandan
