Product name: Oleuropein Aglycone
Synonym name: 3,4-DHPEA-EA; Oleoeuropein Aglycone; Oleoeuropeine Aglycone; Oleuropein Aglycon; Oleuropeine Aglycone
Catalogue No.: BP2079
Cas No.: 31773-95-2
Formula: C19H22O8
Mol Weight: 378.377
Botanical Source: Olive
Type of Compound: Iridoids
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.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
146.5400
1.4500
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Oleuropein Aglycone (3,4-DHPEA-EA, CAS number: 31773-95-2), as one of the important polyphenolic natural products in olive trees (Olea europaea L.), has attracted much attention in recent years due to its extensive biological activity and potential medicinal value. Oleuropein (HY-N0292) is a glycoside form of oleuropein, typically obtained from oleuropein through enzymatic hydrolysis, acidic hydrolysis, or acetyl hydrolysis. As one of the main active forms of polyphenols in olive oil, oleuropein has shown significant pharmacological effects in antioxidant, anti-inflammatory, neuroprotective, and metabolic regulation fields, especially in the prevention and treatment of neurodegenerative diseases, metabolic syndrome, and inflammatory diseases.
This article aims to systematically review the chemical structure and physicochemical properties, plant sources and extraction methods, pharmacological activity and mechanism of action of oleuropein, and explore its clinical application prospects and future research directions based on drug evaluation and pharmacokinetic data. The goal is to provide theoretical support and reference for research and drug development in natural product pharmacology and related fields.
The chemical name of oleuropein is 3,4-dihydroxyphenylethanol-acetate (3,4-DHPEA-EA), with a molecular formula of C20H22O9 and a molecular weight of 378.37. Its structure consists of an aromatic ring system rich in phenolic hydroxyl groups connected to acetate groups, exhibiting typical polyphenolic compound characteristics. Its LogP value is about 1.45, indicating that it has moderate lipid solubility, which is beneficial for membrane penetration and bioavailability. The polar surface area (TPSA) is 146.54 Å ² and the number of hydrogen bond acceptors is 8, indicating its strong hydrophilicity and potential for binding with biomolecules.
The structural characteristics of oleuropein determine its excellent antioxidant capacity and multi-target regulatory ability. Its phenolic hydroxyl group can effectively eliminate free radicals and reduce oxidative stress damage; Meanwhile, the spatial configuration of aromatic rings and ester groups facilitates binding with various enzymes and receptors, exerting multi-level biological effects.
Oleuropein is mainly present in olive leaves, olive fruits, and olive oil, especially in olive leaves and immature fruits where its content is relatively high. The precursor compound oleuropein is the main component of olive polyphenols, and oleuropein is obtained through enzymatic or chemical hydrolysis of oleuropein.
Common extraction methods include:
Enzymatic hydrolysis method Using enzymes such as β - glucosidase to catalyze the hydrolysis of oleuropein, obtaining oleuropein under mild conditions and maintaining its biological activity.
Acid hydrolysis method Using dilute acid to hydrolyze oleuropein under heating conditions, the reaction time and temperature need to be strictly controlled to avoid product degradation.
Acetyl hydrolysis method Treat oleuropein with acetylation reagent, break glycosidic bonds, and release oleuropein.
After extraction, purity identification and structural confirmation are usually carried out using techniques such as high performance liquid chromatography (HPLC), mass spectrometry (MS), and nuclear magnetic resonance (NMR). In recent years, green technologies such as ultrasound assisted extraction and microwave-assisted extraction have also been applied to the preparation of oleuropein, improving extraction efficiency and product quality.
The pharmacological activities of oleuropein include multiple aspects such as neuroprotection, metabolic regulation, anti-inflammatory and antioxidant effects. Relevant studies are mostly based on cell and animal models, demonstrating its significant biological effects.
Alzheimer's disease (AD) is a common neurodegenerative disease characterized by β - amyloid deposition, neuronal loss, and cognitive impairment. Research has shown that dietary intake of oleuropein (50 mg/kg diet) can significantly increase the number of autophagic vesicles in neurons of TgCRND8 transgenic mice with Alzheimer's disease, promote the clearance of abnormal proteins, and reverse cognitive deficits. In addition, oleuropein can reduce the levels of histone deacetylase 2 (HDAC2) in the cortex and hippocampus, regulate epigenetic mechanisms, and promote the recovery of neural plasticity and memory function.
In a high-fat diet induced obesity rat model, oleuropein showed potential to regulate energy metabolism and adipose tissue function. It can increase the excretion of norepinephrine in urine, enhance the levels of adrenaline and uncoupling protein 1 (UCP1) expression in brown adipose tissue between the scapula, and promote the calorie expenditure and fat breakdown of adipose tissue. At the same time, oleuropein reduces plasma leptin levels and total abdominal adipose tissue weight, demonstrating its application value in anti obesity and improving metabolic syndrome.
In a mouse model of pleurisy induced by carrageenan, oleuropein significantly inhibited neutrophil infiltration in the lungs and reduced inflammatory response. It can also reduce the level of lipid peroxidation and the expression of pro-inflammatory cytokine IL-1 β in lung tissue, demonstrating good anti-inflammatory and antioxidant activity. In addition, oleuropein has regulatory effects on various inflammatory mediators and oxidative stress-related signaling pathways, and has potential value in the development of broad-spectrum anti-inflammatory drugs.
The multi-target mechanism of action of oleuropein is the basis of its pharmacological activity, mainly involving the following aspects:
Regulating autophagy pathway By promoting the formation and function of autophagic vesicles in neurons, oleuropein promotes the degradation of abnormal proteins, reduces neurotoxicity, and improves cognitive function.
Epigenetic regulation Reduce histone deacetylase 2 (HDAC2) levels, regulate gene expression, promote neural plasticity and cell survival.
Activate the sympathetic nervous system Enhance levels of norepinephrine and adrenaline, activate UCP1 in brown adipose tissue, promote energy expenditure and fat metabolism.
Antioxidant and anti-inflammatory signaling pathways Inhibiting inflammation related signaling pathways such as NF - κ B and MAPK, reducing the release of pro-inflammatory cytokines, and reducing oxidative stress damage.
Regulating lipid metabolism By affecting leptin levels and adipose tissue function, improving lipid metabolism disorders, and preventing obesity and related metabolic diseases.
Although the specific molecular targets of oleuropein are not yet fully understood, its multi-target and multi pathway mode of action provides a theoretical basis for its broad biological effects.
The molecular weight of oleuropein is 378.37, with a LogP value of 1.45, indicating its moderate lipid solubility, which facilitates transmembrane absorption and bioavailability. Its high TPSA (146.54 Å ²) and abundant number of hydrogen bond acceptors (8) suggest that it may have some hydrophilicity and the ability to bind to targets in vivo.
At present, there is no clear data on the blood-brain barrier penetration ability of oleuropein, and safety indicators such as hepatotoxicity, cardiotoxicity, hERG channel inhibition, and genotoxicity (Ames test) have not been systematically evaluated. Further toxicological and pharmacokinetic studies are urgently needed.
Preliminary animal experiments have shown that oleuropein can exert biological activity in vivo after oral administration, but its absorption, distribution, metabolism, and excretion (ADME) characteristics are not yet clear. In the future, it is necessary to combine in vitro and in vivo experiments and computational simulations to systematically evaluate its pharmacokinetic parameters and safety, providing a basis for clinical translation.
Olive bitter glycoside, as a natural polyphenolic compound, has shown broad application prospects in the prevention and treatment of neurodegenerative diseases, metabolic syndrome, and inflammatory diseases due to its multi-target and multifunctional pharmacological properties. Especially in the adjuvant therapy of Alzheimer's disease, regulation of obesity and metabolic diseases, and intervention in chronic inflammatory states, oleuropein has unique advantages.
Future research should focus on the following directions:
In depth analysis of the mechanism Using modern molecular biology and omics techniques, identify the key molecular targets and signaling pathways of oleuropein, and reveal its multi-level regulatory mechanisms.
Pharmacokinetic and safety evaluation Conduct ADME research and toxicological evaluation of oleuropein in the system to ensure its clinical safety and effectiveness.
Formulation development and optimization of administration routes Develop suitable dosage forms and administration methods based on their physical and chemical properties to improve bioavailability and targeting.
Clinical trial validation Conduct evidence-based clinical trials to validate its efficacy and safety in related diseases, and promote its transition from laboratory to clinical use.
Combination therapy research Explore the synergistic effects of oleuropein with existing drugs or other natural products, and expand its clinical application scope.
As an important glycoside form of olive polyphenols, oleuropein has become a research hotspot in the field of natural product pharmacology due to its excellent antioxidant, anti-inflammatory, neuroprotective, and metabolic regulatory activities. Although the understanding of its mechanism of action and drug properties is still incomplete, existing research has laid a solid foundation for its application in neurodegenerative diseases, metabolic syndrome, and inflammatory diseases. In the future, through systematic mechanism research, pharmacokinetic and safety evaluation, as well as clinical validation, oleuropein is expected to become an important candidate molecule for natural drug development, contributing new natural drug resources to human health.
