Product name: cis-Ferulic acid 4-O-β-D-glucopyranoside
Synonym name: 4-O-β-D-Glucopyranosyl-cis-ferulic acid; cis-4-O-β-D-Glucopyranosylferulic acid
Catalogue No.: BP5096
Cas No.: 94942-20-8
Formula: C₁₆H₂₀O₉
Mol Weight: 356.327
Botanical Source:
Type of Compound:

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

Ferulic acid, a natural phenolic compound widely found in plant cell walls, has attracted attention for its remarkable antioxidant, anti-inflammatory, and various pharmacological activities. Its derivative—(Z)-ferulic acid 4-O-β-D-glucopyranoside, hereinafter referred to as "cis-ferulic acid glucoside"—is a natural product with unique structural characteristics that has shown potential pharmacological value in recent years in the field of anti-platelet aggregation. Platelet aggregation, as a key link in thrombosis formation, is an important pathological basis for various cardiovascular and cerebrovascular diseases. Regulating platelet function has become an important strategy for preventing and treating atherosclerosis, myocardial infarction, and stroke. This paper systematically reviews the chemical structure, plant origin, pharmacological activity, mechanism of action, and druggability evaluation of cis-ferulate glucoside, aiming to provide theoretical support and research directions for its clinical application and new drug development.

Chemical structure and physicochemical properties

The chemical structure of cis-ferulic acid glucoside is based on the framework of ferulic acid, characterized by the cis-form (cis) configuration of ferulic acid and the β-D-glucosidic bond at position 4. Its molecular formula is C17H20O9, molecular weight is 356.3270, and its structure includes phenolic hydroxyl, methylene, and glucose units, giving it high polarity and water solubility. In terms of physicochemical properties, its LogP value is -0.1251, indicating low lipid solubility, indicating good solubility in the aqueous phase (about 21.2449 mg/mL). TPSA (topological pole surface area) is 145.9100 Ų, indicating that its molecules possess strong polarity and hydrogen bond donor/acceptor capacity, which positively affects their binding to biological targets. The blood-brain barrier penetration ability is relatively low, suggesting it mainly acts on the peripheral system to reduce the risk of adverse reactions in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test result was 0.0, indicating no significant genotoxicity.

Plant Origins and Extraction Methods

Cis-Ferulate Glucoside is mainly found in various Chinese medicinal materials and edible plants, especially abundant in certain grasses and medicinal herbs. For example, certain ferulic acid derivatives have been reported in Angelica sinensis, Astragalus membranaceus, and other traditional Chinese medicinal herbs. The extraction method typically uses water or alcohol-based solvents (such as ethanol or methanol) for extraction and combines ultrasound-assisted or microwave-assisted extraction to improve extraction efficiency. Subsequently, separation, purification, and qualitative quantitative analysis were performed using liquid chromatography (HPLC) or high-performance liquid chromatography-mass spectrometry (HPLC-MS/MS) techniques. The stability of the glucosidic bonds is relatively good; during extraction, it is important to avoid high temperatures and strong acidic or alkaline conditions to prevent hydrolysis.

Pharmacological activity research

Antiplatelet aggregation activity

Cis-ferulate glucoside demonstrated significant anti-platelet aggregation effects in in vitro platelet function experiments. By inhibiting platelets' responses to various aggregation inducers (such as ADP, collagen, thromboxane A2, etc.), it reduces the activation and aggregation capacity of platelets, thereby lowering the risk of thrombosis. Experimental data showed that this compound significantly inhibited platelet aggregation at concentrations as low as micromoles, with efficacy superior to non-glycosided ferulic acid, suggesting that the glucoside structure enhances its biological activity.

Antioxidant and anti-inflammatory effects

As a derivative of ferulic acid, cis-ferulate glucoside also has excellent antioxidant properties, scavenging free radicals and reducing oxidative stress damage to vascular endothelium and platelets. Moreover, its regulation of inflammatory mediators shows potential by inhibiting the expression of inflammatory factors such as TNF-α and IL-6, reducing vascular inflammatory responses, and indirectly promoting vascular health.

Other potential pharmacological effects

Some studies also suggest that this compound may regulate blood lipids and protect myocardium and nerve cells, but the related mechanisms require further elucidation.

Mechanism of action and molecular targets

The antiplatelet aggregation effect of cis-ferulate glucoside is mainly achieved through multi-target coordinated regulation, involving the following key targets:

• PTGS1 (COX-1) and PTGS2 (COX-2): This compound can inhibit cyclooxygenase activity in platelets, reduce the production of thromboxane A2 (TXA2), and decrease platelet activation signaling.
• ITGA2B and ITGB3: As subunits of integrin αIIbβ3 on platelet membranes, cis-ferulic acid glucoside blocks platelet binding by regulating its conformation and expression.
• P2RY12 (P2Y12 receptor): This receptor is a key target for ADP-mediated platelet aggregation. Cis-ferulate glucoside may antagonize P2Y12 receptors and inhibit ADP-induced platelet activation.
• TBXA2R (thromboxane A2 receptor): Inhibits the thromboxane A2 signaling pathway, reducing platelet aggregation and vasoconstriction.
• PDE3A (phosphodiesterase 3A): By inhibiting PDE3A activity, it increases intracellular cAMP levels and suppresses platelet activation.
• GP1BA: This glycoprotein acts as an important mediator for platelet binding to collagen exposed in vascular endothelium. Cis-ferulate glucoside may regulate its function and weaken initial platelet adhesion.

Overall, cis-ferulate glucoside effectively inhibits platelet activation and aggregation through multi-target and multi-pathway synergistic effects, demonstrating good antithrombotic potential.

Druggability evaluation and pharmacokinetics

From the druggability parameter analysis, CIS-glucoside ferulate has good drug development potential. It has a moderate molecular weight and good water solubility, which is beneficial for oral absorption and internal distribution. Low lipid solubility and a relatively high TPSA value suggest that it may have some bioavailability limitations, but also reduce the risk of nonspecific lipid binding and toxicity. The blood-brain barrier penetration rate is low, reducing the likelihood of central side effects. hERG channel inhibition is negative, and Ames tests show no mutagenicity, indicating relatively high safety.

Pharmacokinetics, current research is limited, but it is speculated that its glucoside structure may be hydrolyzed by β-glucosidase in the intestine, releasing active ferulic acid and affecting its bioavailability and metabolic kinetics. In the future, systematic studies are needed on its absorption, distribution, metabolism, and excretion (ADME) characteristics to clarify its in vivo transformation pathways and metabolite activity.

Prospects and outlooks for clinical applications

Given the significant activity of cis-ferulate glucoside in antiplatelet aggregation and antioxidant and anti-inflammatory properties, this compound has broad clinical application prospects. First, as a natural product derivative, it is relatively safe and suitable as an adjunct drug or health supplement ingredient for cardiovascular and cerebrovascular diseases. Secondly, for the prevention and treatment of diseases such as atherosclerosis, coronary heart disease, and stroke, cis-ferulate glucoside can be a candidate molecule for antiplatelet drugs, especially suitable for patients with poor tolerance to traditional antiplatelet drugs or who are at risk of bleeding.

Future research should focus on:

• In vivo pharmacodynamics and toxicology evaluation to clarify the safe dosage range and long-term risks;
• Systematic research on pharmacokinetics and metabolic mechanisms, optimizing administration routes and dosage forms;
• Clinical trials verify its efficacy and safety, promoting its translation into clinical application;
• Structural optimization and derivative development to enhance bioavailability and targeting.

In addition, by combining modern molecular biology and computer-aided drug design technologies, the study deeply analyzes its mechanisms of action and target interactions, providing a theoretical foundation for the development of novel antiplatelet drugs.

Conclusion

Cis-Ferulic acid glucoside, as a natural product derivative with multi-target anti-platelet aggregation activity, demonstrates good pharmacological activity and drug development potential. Its unique chemical structure gives it excellent water solubility and safety, and by regulating key targets such as PTGS1/2, ITGA2B/ITGB3, and P2RY12, it effectively inhibits platelet function and reduces the risk of thrombosis. Although research on its pharmacokinetics and clinical application in vivo is still in its early stages, its prospects as a new drug candidate for the prevention and treatment of cardiovascular and cerebrovascular diseases are promising. In the future, combining multidisciplinary interdisciplinary research will provide solid support for the drug development and clinical application of cis-glucoside ferulate, promoting the widespread use of natural products in modern medicine.