Product name: Linaroside
Synonym name: Pectolinarigenin 7-O-β-glucoside
Catalogue No.: BP4663
Cas No.: 53452-12-3
Formula: C₂₃H₂₄O₁₁
Mol Weight: 476.434
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℃

Introduction/Overview

Linaroside-7-O-glucoside (CAS No.: 53452-12-3) is a natural flavonoid product originally isolated and identified from Lantana camara, a plant of the genus Euphagia strifolia. As a typical representative of flavonoid compounds, willow chlorin-7-O-glucoside has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique chemical structure and diverse biological activity. Its significant role in liver protection, especially in shielding against hepatocyte damage and antioxidant capacity, makes it a potential natural drug candidate for liver disease treatment.

As an important metabolic and detoxifying organ in the human body, the liver is easily damaged by various endogenous and exogenous toxins and inflammatory reactions, leading to diseases such as hepatitis, liver fibrosis, and even cirrhosis. Currently, treatment options for liver disease are limited and have many side effects, making the development of safe and effective hepatoprotectants of significant clinical significance. Willow-transcopictin-7-O-glucoside demonstrates good liver-protective potential by regulating various oxidative stress-related enzymes and signaling pathways. This paper systematically reviews the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity and mechanism of action of willow transcoccillin-7-O-glucoside, as well as druggability evaluation and clinical application prospects, aiming to provide theoretical basis and reference for subsequent research and drug development.

Chemical structure and physicochemical properties

Cyptocoside-7-O-glucoside belongs to the flavonoid class of flavonoid compounds, with a molecular formula of C_22H_24O_12 and a molecular weight of 476.4340. Its structural feature is that the flavonoid nucleus is connected to a glucoside at position 7 via a hydroxyl group, forming a 7-O-glucosidic bond. The flavonoid nucleus has a typical C6-C3-C6 tricyclic structure, containing two benzene rings (A and B rings) and one oxygen heterocycle (C ring). The introduction of glucosides significantly increases the molecule's polarity and water solubility.

In terms of physicochemical properties, the LogP value of willow chlorine-7-O-glucoside is 0.4859, indicating strong hydrophilicity and good water solubility (0.5220), which is beneficial for absorption and distribution in the body. The topological pole surface area (TPSA) is 168.2800, and a higher TPSA value is usually associated with lower blood-brain barrier permeability, consistent with experimental data for low blood-brain barrier permeability. Additionally, this compound does not inhibit the hERG channel, and the Ames test result is 0.6, indicating a low genotoxicity risk and good safety.

In summary, the chemical structure of willow chloranthocyrin-7-O-glucoside gives it good water solubility and low toxicity risk, providing a solid foundation for its use as a drug molecule.

Plant Origins and Extraction Methods

Chlorophyllin-7-O-glucoside mainly comes from Lantana camara, a plant of the Pleuropium genus, which is widely distributed in tropical and subtropical regions and is often used as an ornamental plant and as a traditional herb. The leaves, flowers, and stems of Lantana camara are rich in flavonoids, with the content of 7-O-glucoside being particularly high.

The extraction method typically uses solvent extraction combined with chromatography separation technology. The specific steps include:

1. Raw material preparation: Collect fresh or dried Lantana camara leaves and crush them into a fine powder.
2. Solvent extraction: Use methanol, ethanol, or water-ethanol mixed solvents for reflux or ultrasound-assisted extraction, with extraction time generally lasting 2-4 hours.
3. Concentration and separation: After the extract is concentrated under reduced pressure, liquid-liquid distribution is used to remove fat-soluble impurities.
4. Chromatographic purification: Target components are separated and purified using silica gel column chromatography, reversed-phase high-performance liquid chromatography (RP-HPLC), and other techniques, ultimately obtaining high-purity willow chlorinocoxanthin-7-O-glucoside.
5. Structural identification: Confirm compound structure using mass spectrometry (MS), nuclear magnetic resonance (NMR), and UV-Vice spectroscopy.

In recent years, advances in extraction technology, such as supercritical fluid extraction and molecular blotting, are expected to further improve the extraction efficiency and purity of willow chlorin-7-O-glucoside, laying the foundation for its large-scale production.

Pharmacological activity research

Pharmacological activity studies of willow chlorin-7-O-glucoside mainly focus on its hepatoprotective effects and antioxidant capacity. Numerous in vivo and in vitro experiments have shown that this compound can effectively reduce liver cell damage, inhibit liver fibrosis, and exert anti-inflammatory and anti-fibrotic effects by regulating the expression of oxidative stress-related enzymes.

Hepatoprotective effects

Multiple animal model studies have shown that willow chlorin-7-O-glucoside can significantly reduce liver injury markers induced by chemical toxins (such as carbon tetrachloride and alcohol), including elevated serum ALT and AST levels. Histopathological analysis confirmed that it can reduce hepatocyte necrosis and inflammatory infiltration, protecting the structural integrity of the liver.

Antioxidant activity

Willow Chlorcoxanthin-7-O-glucoside enhances the activity of endogenous antioxidant enzymes (such as SOD, CAT, GPX), scavenging excess reactive oxygen species (ROS) and reducing oxidative stress damage to liver cells. In vitro experiments have shown that this compound can effectively inhibit free radical production, protecting cells from oxidation-induced apoptosis.

Anti-inflammatory and anti-fibrotic

Willow-tocoxanthin-7-O-glucoside also demonstrates the ability to regulate the expression of inflammatory factors and fibrosis-related genes. By downregulating transforming growth factor β1 (TGFB1) and related signaling pathways, it inhibits the activation of hepatic stellate cells and slows the progression of liver fibrosis.

Additionally, preliminary studies suggest that this compound may have certain antitumor and immunomodulatory effects, but the related mechanisms require further exploration.

Mechanism of action and molecular targets

The hepatoprotective effects of willow chloranthin-7-O-glucoside involve multiple molecular signaling pathways and targets, mainly including antioxidant stress, anti-inflammatory response, and anti-fibrotic mechanisms.

Antioxidant stress mechanism

This compound activates the nuclear factor E2-associated factor 2 (NRF2) signaling pathway, promoting the expression of downstream antioxidant enzymes such as NAD(P)H, quinone oxidoreductase 1 (NQO1), heme oxygenase 1 (HMOX1), superoxide dismutase 1 and 2 (SOD1, SOD2), catalase (CAT), glutathione peroxidase 1 (GPX1), and others, thereby enhancing cellular antioxidant defenses, reducing ROS accumulation, and protecting hepatocytes from oxidative damage.

Anti-inflammatory and anti-fibrotic mechanisms

Willowocarcin-7-O-glucoside inhibits transforming growth factor β1 (TGFB1) and its downstream signaling, blocks the activation of hepatic stellate cells and the proliferation of myofibroblasts, reduces extracellular matrix deposition, and delays the progression of liver fibrosis. At the same time, this compound may also regulate actin α2 (ACTA2) expression, affecting the morphology and function of fibrosis-related cells.

Other potential targets

Matrix metalloproteinase 9 (MMP9), an important enzyme for liver tissue remodeling, is also regulated by willow chloranthin-7-O-glucoside, promoting repair and regeneration of damaged liver tissue.

In summary, willow chlorine-7-O-glucoside exerts comprehensive hepatoprotective effects through multi-target and multi-pathway synergistic effects.

Druggability evaluation and pharmacokinetics

From the perspective of druggability, willow chlorin-7-O-glucoside exhibits relatively ideal drug properties. Its molecular weight (476.4340) is within an appropriate range, and the LogP value (0.4859) indicates moderate molecular hydrophilicity, which is beneficial for absorption in the body. Although a high TPSA (168.2800) limits its ability to cross the blood-brain barrier, it is not a disadvantage for liver-targeted drugs and actually reduces the risk of central nervous system side effects.

In terms of safety, this compound does not inhibit hERG channels, reducing the risk of cardiotoxicity. Ames test results (0.6) showed low genotoxicity and a solid safety foundation.

Currently, research on pharmacokinetics is relatively limited. Preliminary in vivo experiments showed that after oral administration of liuchuan-coccyloid-7-O-glucoside, it could be detected in plasma, suggesting a certain degree of bioavailability. The glucoside structure may be transformed by gut microbiota hydrolysis into more easily absorbed flavonoid nuclei, affecting metabolic pathways in vivo. Future studies are needed to systematically study its absorption, distribution, metabolism, and excretion (ADME) characteristics to clarify its in vivo dynamic behavior.

Prospects and outlooks for clinical applications

Given the multi-target and multi-mechanism effects of willow chloranthocyrin-7-O-glucoside in the field of liver protection, its potential as a natural hepatoprotector is enormous. The future clinical application prospects are mainly reflected in the following aspects:

1. Adjunctive treatment for liver injury
   It is suitable for liver cell damage caused by drugs, alcohol, viruses, or other toxins, serving as an adjunctive therapy to alleviate abnormal liver function and promote liver repair.

2. Prevention and treatment of liver fibrosis
   By inhibiting the progression of liver fibrosis, it delays the progression of cirrhosis and improves patient prognosis.

3. Management of chronic liver disease
   Combined with existing antiviral or immunomodulatory therapies, improve the liver microenvironment and enhance treatment efficacy.

4. Safety and tolerability advantages
   As a natural product, willow chlorinin-7-O-glucoside carries a low risk of toxic side effects and is suitable for long-term use.

However, clinical translation still faces many challenges, including systematic pharmacokinetic studies, formulation development, determination of effective dosage and administration regimens, and the implementation of large-scale clinical trials. Future research should strengthen the pharmacodynamic and toxicological evaluation of willow chlorine xanthin-7-O-glucoside and explore its potential for combined application with existing liver disease treatment drugs.

Conclusion

As a natural flavonoid glycoside derived from Lantana camara, Wiludian-7-O-glucoside demonstrates significant hepatoprotective activity due to its unique chemical structure and excellent physicochemical properties. By regulating various antioxidant enzymes and fibrosis-related targets, it exerts antioxidant, anti-inflammatory, and anti-fibrotic effects, providing new ideas and potential drug candidates for liver disease treatment.

Although its pharmacological mechanisms are preliminarily understood, its pharmacokinetic characteristics and clinical applications still require in-depth study. In the future, systematic evaluation of willow chloranthin-7-O-glucoside should be strengthened, promoting its translation from laboratory research to clinical application, with the hope that it will become a safe and effective liver protection drug and bring hope to liver disease patients.