Product name: 6-hydroxyl luteolin-7-O-glucoside
Synonym name: 6-Hydroxyluteolin 7-O-β-D-glucopyranoside； 6-Hydroxyluteolin 7-O-β-glucoside
Catalogue No.: BP4279
Cas No.: 54300-65-1
Formula: C₂₁H₂₀O₁₂
Mol Weight: 464.379
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.

NMR of 6-hydroxyl luteolin-7-O-glucoside

HPLC of 6-hydroxyl luteolin-7-O-glucoside

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

6-hydroxyl luteolin-7-O-glucoside (CAS No.: 54300-65-1) is a natural flavonoid glycoside that is widely found in various traditional Chinese medicinal plants. As a hydroxyl derivative of luteoside, 6-hydroxyoleolaside imparts significant biological activity due to its unique chemical structure, showing excellent pharmacological potential especially in liver protection. In recent years, with the deepening development of natural product pharmacology, 6-hydroxylutein has become one of the hot molecules in liver disease prevention and treatment due to its antioxidant, anti-inflammatory, and ability to regulate cellular signaling pathways. This paper will systematically review the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity and mechanism of action of 6-hydroxylutein (6-hydroxylutein glycoside), druggability evaluation and pharmacokinetic characteristics, and conduct in-depth discussions in conjunction with its clinical application prospects, aiming to provide a theoretical basis and research direction for further drug development of this compound.

Chemical structure and physicochemical properties

6-hydroxyluteolin belongs to the flavonoid class, specifically a glycosidic bond formed between 6-hydroxyluteolin and glucose via the 7-O site. Its molecular formula is C21H20O12, and its molecular weight is 464.3790. Structurally, 6-hydroxylutein introduces a hydroxyl group at position 6 of the flavonoid A ring based on luteoside, enhancing its polarity and hydrogen bond donor capacity, thereby affecting its biological activity and pharmacokinetic properties.

In terms of physicochemical properties, the compound has a LogP value of -0.2363, indicating strong hydrophilicity and matching its high water solubility (0.9622), which is beneficial for dissolution and absorption in aqueous environments. The polar surface area (TPSA) is 210.5100, and a higher TPSA value is usually associated with poor cell membrane permeability, consistent with the low blood-brain barrier permeability. Additionally, 6-hydroxyoleolaside does not exhibit hERG channel inhibitory activity, suggesting a low risk of cardiotoxicity. The Ames test result was 1.2, indicating that this compound has no significant mutagenicity and is relatively safe.

Plant Origins and Extraction Methods

6-hydroxylutein is mainly found in various traditional medicinal plants, especially Luteolin and related plants such as Scutellaria baicalensis and Sonchus oleraceus. Its content is greatly affected by plant species, growing environment, and harvest time.

Extraction methods mostly use water extraction and alcohol precipitation or ultrasound-assisted extraction techniques. The general process includes: crushing dried plants, extracting them with 70%-80% ethanol as the solvent, combined with ultrasonic assistance to improve extraction efficiency. After concentration, the extract was purified and quantitatively analyzed using liquid chromatography (HPLC) or high-performance liquid chromatography-mass spectrometry (HPLC-MS) techniques. In recent years, the application of supercritical fluid extraction (SFE) and membrane separation technologies has gradually increased, aiming to improve extraction purity and yield while reducing the use of organic solvents, in line with green chemistry principles.

Pharmacological activity research

6-Hydroxylutein demon glycoside exhibits significant biological activity across various in vitro and in vivo models, with particularly in-depth research on hepatoprotection.

Antioxidant activity

This compound effectively scavenges free radicals and reduces oxidative stress damage to liver cells by enhancing endogenous antioxidant enzyme activity (such as SOD1, SOD2, CAT, GPX1) and inducing antioxidant gene expression (NQO1, HMOX1). Multiple studies have shown that 6-hydroxyoleoside can activate the nuclear factor red 2-associated factor 2 (NRF2) signaling pathway, promote upregulation of the antioxidant defense system, reduce lipid peroxidation levels, and protect the integrity of hepatocyte membranes.

Anti-inflammatory effects

6-Hydroxyluoin alleviates liver inflammation by inhibiting the pro-inflammatory factor TGFB1 and related signaling pathways. Its inhibitory effect on the hepatic stellate cell activation marker ACTA2 helps prevent the progression of liver fibrosis. Additionally, this compound can regulate the expression of matrix metalloproteinase MMP9, influence extracellular matrix remodeling, and slow down pathological changes in the liver.

Hepatoprotective effects

In various liver injury models (such as alcoholic liver injury, drug-induced liver injury, and fatty liver models), 6-hydroxylutein showed significant hepatoprotective effects. Its mechanisms involve multiple pathways, including antioxidant, anti-inflammatory, anti-fibrotic, and cell apoptosis regulation. In vivo experiments showed that after administration of 6-hydroxylucoside, liver function indicators (such as ALT and AST) improved significantly, and pathological damage to liver tissue was reduced, indicating good clinical application potential.

Mechanism of action and molecular targets

The pharmacological effects of 6-hydroxylutein mainly achieve this by regulating various key molecular targets:

• NRF2 (Nuclear Factor 2-Related Factor 2): As the main regulator of cellular antioxidant stress, NRF2 activation promotes the expression of downstream antioxidant enzymes (NQO1, HMOX1, SOD1, SOD2, CAT, GPX1), enhancing cellular antioxidant capacity and reducing oxidative damage.

• MMP9 (matrix metalloproteinase 9): regulates extracellular matrix degradation and participates in liver fibrosis. 6-hydroxyoleolaside slows fibrosis progression by inhibiting MMP9 expression.

• TGFB1 (transforming growth factor β1): a key pro-fibrotic factor that regulates hepatic stellate cell activation and collagen deposition. This compound inhibits the TGFB1 signaling pathway, helping to prevent liver fibrosis.

• ACTA2 (α-smooth muscle actin): a hallmark of hepatic stellate cell activation and involved in the formation of fibrotic cells. 6-hydroxyoleoloside inhibits ACTA2 expression and blocks the activation of fibrotic cells.

In summary, 6-hydroxylutein demon glycoside exerts its comprehensive hepatoprotective and anti-fibrotic pharmacological effects through multi-target and multi-pathway synergistic effects.

Druggability evaluation and pharmacokinetics

From the perspective of druggability parameters, 6-hydroxylutein has certain advantages and challenges:

• High water solubility (0.9622) is beneficial for the preparation and absorption of oral formulations, but higher polarity (TPSA 210.5100) may limit cell membrane penetration and affect bioavailability.

• The LogP value was -0.2363, indicating strong hydrophilicity, which may lead to slow oral absorption and requires improvement through pharmacological methods.

• The low permeability of the blood-brain barrier suggests it mainly acts on peripheral tissues, reducing the risk of central nervous system side effects.

• hERG channel inhibition negative, reducing cardiotoxicity risk and facilitating safety evaluation.

• The Ames test result was 1.2, with no significant mutagenicity, indicating good safety.

Currently, pharmacokinetic studies on 6-hydroxylusolin are limited. Preliminary data indicate that oral absorption is slow, and metabolism in the body is mainly carried out through hepatic enzyme systems, with metabolites possibly including deglycosyls and hydroxylated derivatives. In the future, further systematic pharmacokinetic and metabolic kinetics studies are needed to clarify their distribution, metabolic pathways, and excretion characteristics in vivo, providing a basis for clinical development.

Prospects and outlooks for clinical applications

Given the multiple pharmacological activities of 6-hydroxylutein in liver protection, its application prospects in liver disease prevention and treatment are broad. Especially in common liver diseases such as alcoholic liver disease, non-alcoholic fatty liver disease (NAFLD), drug-induced liver injury, and liver fibrosis, 6-hydroxylutein is expected to become a new natural liver protectant.

The key to future clinical applications lies in:

1. Dosage form optimization: Given its water solubility and polarity, suitable formulation forms (such as nanoparticles, liposomes, solid dispersions, etc.) need to be developed to improve bioavailability and targeting.

2. Safety Evaluation: Systematically conducts long-term toxicology and drug interaction studies to ensure clinical medication safety.

3. Clinical trial design: Based on existing pharmacological evidence, design a reasonable clinical trial protocol to verify efficacy and safety.

4. In-depth mechanistic research: Further elucidating its mechanism of action, especially new targets related to hepatic immune regulation and metabolic regulation, provides theoretical support for precision treatment.

In addition, the antioxidant and anti-inflammatory properties of 6-hydroxylutein also suggest its potential application value in other chronic diseases (such as cardiovascular diseases and neurodegenerative diseases), warranting further research.

Conclusion

6-hydroxylutein glycoside, a natural flavonoid glycoside with a unique structure, demonstrates broad prospects for drug development due to its significant hepatoprotective effects and good safety. By regulating multiple cellular signaling pathways, it exerts antioxidant, anti-inflammatory, and anti-fibrotic effects, providing new ideas for the prevention and treatment of liver diseases. In the future, combined with advanced drug formulation technologies and systematic pharmacokinetic studies, 6-hydroxylutein is expected to become an important member of the natural product drug field, driving innovative development in liver disease treatment. Researchers should continue to monitor its mechanisms and clinical translation to promote its early clinical application.