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Olivil 4'-O-glucoside (CAS No.: 76880-93-8) is a class of natural lignosin glycosides widely found in various plants, especially those of the Olive genus. As an important member of the lignol family, olive-4'-O-glucoside has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique chemical structure and diverse bioactivity. This compound exhibits certain antioxidant activity, especially with potential applications in free radical scavenging. In addition, the druggability parameters of oldehydan-4'-O-glucoside demonstrate good safety and biocompatibility, laying a foundation for further pharmacological research and clinical development.
This paper aims to systematically review the chemical structure, physicochemical properties, plant origin, and extraction methods of oldehyde-4'-O-glucoside, explore its pharmacological activity and mechanism of action in depth, evaluate its druggability and pharmacokinetic characteristics, and anticipate its clinical application potential, aiming to provide theoretical support and practical guidance for related research.
The chemical name of oleuropein-4'-O-glucoside is 4-{[(3S,4R,5S)-3-hydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)tetrahydro-3-furanoyl]methyl}-2-methoxyphenyl β-D-glucoside, with a molecular formula of C26H34O12 and a molecular weight of 538.5460. Its structure belongs to lignosin glycoside compounds, with a core backbone consisting of a tetrahydrofuran ring connecting two phenyl units, with one phenyl bonded to β-D-glucoside via a 4' site.
In terms of physicochemical properties, oldehydran-4'-O-glucoside has low hydrophobicity (LogP=0.0812), indicating strong hydrophilicity, and its total polar surface area (TPSA) reaches 187.76 Ų, reflecting a high concentration of polar functional groups such as hydroxyl and methoxy groups, giving it good water solubility (water solubility index about 2.1762). These properties give the compound good solubility in aqueous environments, facilitating absorption and distribution within living organisms.
Additionally, oleuropein-4'-O-glucoside lacks the ability to penetrate the blood-brain barrier, suggesting that its main target may be limited to peripheral tissues. In terms of safety, the hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity; The Ames mutagenicity test result was 0.0, indicating no significant mutagenicity, meeting safety requirements for drug development.
Olimin-4'-O-glucoside is mainly found in olive plants (Olea europaea) and its related species, especially abundant in olive leaves, fruits, and roots. In addition, some plants with higher lignophenol content, such as those in the Ephedraceae and Juglandaceae families, have also been reported to contain this compound or derivatives of similar structures.
Traditional methods for extracting oleuropein-4'-O-glucoside mostly use polar solvents, such as methanol, ethanol, or water-alcohol mixed solvents, obtained by extraction or reflux to obtain crude extracts. Subsequently, separation and purification were performed using liquid-liquid partitioning, column chromatography (such as silica gel columns, reversed-phase C18 columns), and high-performance liquid chromatography (HPLC). In recent years, the application of emerging technologies such as ultrasound-assisted extraction and microwave-assisted extraction has improved extraction efficiency and purity, reducing extraction time and solvent usage.
In terms of identification, methods such as mass spectrometry (MS), nuclear magnetic resonance (NMR), and infrared spectroscopy (IR) were used to confirm the structure of the purified products. In particular, two-dimensional NMR techniques (such as COSY, HSQC, HMBC) provide key evidence for elucidating glycoside bonding locations and stereotypes.
Pharmacological activity studies of olde-4'-O-glucoside mainly focus on its antioxidant, anti-inflammatory, and neuroprotective aspects.
As a lignosin compound, oleuropein-4'-O-glucoside exhibits certain free radical scavenging ability. In vitro DPPH radical scavenging experiments show that its EC50 is about 176 μM, which is considered a weak antioxidant. Although its antioxidant capacity is not as strong as some potent polyphenols, its abundant hydroxyl and methoxy groups in its structure give it certain electron donor capabilities, allowing it to capture free radicals and reduce cellular damage caused by oxidative stress.
Some in vitro cell models and animal experiments have shown that oleuropein-4'-O-glucoside can inhibit the release of inflammatory mediators such as tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and nitric oxide (NO). Its anti-inflammatory mechanism may involve regulation of the NF-κB signaling pathway, weakening the cascading amplification effect of inflammatory responses and thereby protecting tissues from chronic inflammatory damage.
Due to its antioxidant and anti-inflammatory properties, oleuropein-4'-O-glucoside has shown certain protective effects in neurodegenerative disease models. For example, in in vitro neuronal models, this compound can alleviate oxidative stress-induced apoptosis and promote nerve cell survival. Although its blood-brain barrier penetration ability is relatively low, it is suitable for peripheral neuroprotection or as an adjunctive therapy.
Preliminary studies also suggest that olde-4'-O-glucoside may have potential for anti-tumor, antibacterial, and immune function regulation, but relevant data are still insufficient and require further systematic research for validation.
The mechanism of action of oleuropein-4'-O-glucoside mainly revolves around its antioxidant and anti-inflammatory activities.
This compound directly scavenges free radicals by providing hydrogen atoms or electrons, terminating the radical chain reaction and reducing oxidative damage. Additionally, its hydroxyl groups can chelate transition metal ions (such as iron and copper), inhibiting hydroxyl radicals produced in the Fenton reaction, thereby indirectly exerting antioxidant effects.
Oleuropein-4'-O-glucoside regulates multiple signaling pathways, especially the NF-κB and MAPK pathways. By inhibiting the phosphorylation and degradation of IκBα, it prevents NF-κB transcription factors from entering the nucleus, reducing the expression of pro-inflammatory factor genes. At the same time, it inhibits the activation of MAPKs such as p38 and JNK, reducing the synthesis and release of inflammatory mediators.
Currently, no clear high-affinity targets have been reported, but it is speculated that their targets may include oxidative stress-related enzymes (such as superoxide dismutase SOD, glutathione peroxidase GPx), inflammatory signaling molecules (such as the IKK complex, TNF-α receptor), and related transcription factors. In the future, through molecular docking and proteomics research, it is expected that more specific targets and networks of action will be revealed.
The druggability parameters of oleuropein-4'-O-glucoside indicate that it has certain development potential.
The molecular weight of 538.5460 is in the medium range, and a LogP value of 0.0812 indicates strong hydrophilicity, which is favorable for dissolution and absorption; the TPSA value of 187.76 is relatively high, which may limit its cell membrane penetration, especially the weak ability to pass through the blood-brain barrier.
The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. Ames mutagenic test results were 0, indicating no mutagenicity and good safety.
Currently, in vivo pharmacokinetic data on oleuropein-4'-O-glucoside are limited. Based on its structure and physicochemical properties, it is speculated that oral absorption may be limited by high polarity and glycoside structure, and its bioavailability may be low. Its metabolic pathway may involve gut microbiota hydrolyzing glycosidic bonds, releasing active lignophenol cores, followed by hepatic phase I and phase II metabolic transformation. Excretion is mainly through urine and bile.
Future pharmacokinetic studies are needed to clarify its absorption, distribution, metabolism, and excretion (ADME) characteristics, providing a basis for dosage formulation design and administration protocol optimization.
Odolin 4'-O-glucoside, with its antioxidant and anti-inflammatory activities, shows potential value in the prevention and treatment of various chronic diseases.
Chronic inflammation is the common pathological basis for cardiovascular diseases, diabetes, arthritis, and other diseases. Oleuropein-4'-O-glucoside is expected to become a natural anti-inflammatory drug or adjunct therapy by modulating inflammatory signaling pathways, reducing the burden of inflammation and improving tissue function.
Although its ability to penetrate the blood-brain barrier is limited, its inhibitory effects on peripheral neuroinflammation and oxidative stress may help in adjunctive treatment for neurodegenerative diseases such as Parkinson's and Alzheimer's. In the future, structural modification or nanocarrier technology can enhance its brain-targeting capabilities.
As a natural antioxidant, oldehydline-4'-O-glucoside is suitable for development as a functional health supplement to prevent oxidative stress-related sub-health conditions and age-related diseases.
Oleuropein-4'-O-glucoside, as a typical natural lignoside glycoside, demonstrates broad research and application prospects in fields such as antioxidant, anti-inflammatory, and neuroprotective fields due to its unique chemical structure and diverse biological activities. Although current research has revealed some pharmacological effects and safety advantages, further exploration of its molecular mechanisms, pharmacokinetics, and clinical efficacy is still needed. In the future, combining modern medicinal chemistry and biotechnological approaches, oleuropein-4'-O-glucoside is expected to become an important candidate molecule for the development of natural product drugs, providing new strategies and ideas for the prevention and treatment of related diseases.
Shenshuai
Wenjing
Hedandan
