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Product name: Oleuropeinic acid
Synonym name:
Catalogue No.: BP2108
Cas No.: 96382-90-0
Formula: C25H30O15
Mol Weight: 570.5
Botanical Source: Ligustrum lucidum Ait.
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.
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℃
238.9700
-.6077
-2.4381
12.6883
.4573
.1452
Low
73.7836
4.7329
Yes
No
No
No
No
No
0.0
Yes
Yes
Yes
Yes
Oleuropeinic acid, CAS number 96382-90-0, is a natural compound found in the tissue of olive (Olea europaea) and can also be formed through heat treatment and oxidation of Oleuropein. As an important derivative of polyphenolic compounds in olives, oleuropein picric acid has attracted widespread attention in recent years in the field of natural product pharmacology due to its remarkable antioxidant activity and multi-target regulatory effects. Its unique biological function makes it an emerging candidate for research into cardiovascular diseases, especially the prevention and treatment of atherosclerosis.
Atherosclerosis is a complex disease characterized by lipid deposits in the walls of arterial vessels and chronic inflammatory responses, posing a serious threat to global public health. Oleuropein demonstrates potential therapeutic value by regulating multiple key molecular targets (such as LOX-1, AMPK, ABCA1, etc.) to participate in pathological processes such as lipid metabolism, oxidative stress, and apoptosis. This paper aims to systematically review the chemical structure and physicochemical properties of oleuropein picric acid, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and to explore its clinical application prospects and development directions, providing a theoretical foundation and reference for subsequent research and drug development.
The molecular formula of oleuropein picric acid is C_25H_34O_15, with a molecular weight of 570.50 Da. Its structural basis comes from the phenolic acid portion of oleuropein, which contains multiple hydroxyl groups and ester bonds, giving it strong polarity and water solubility. Physicochemical properties showed that the LogP value of oleuropein picric acid was about -0.61, indicating strong hydrophilicity, with a water solubility of 12.69 mg/mL, suitable for biological activity in aqueous media. Its extremely high polarity is also reflected in its topological pole surface area (TPSA) of 238.97 Ų, suggesting that its molecules have abundant hydrogen bond donors and acceptors, facilitating stable binding with biological macromolecules such as protein targets.
Additionally, oleuropein has low blood-brain barrier permeability, suggesting limited direct effects on the central nervous system, but this may also reduce the risk of CNS toxicity. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. Ames mutagenicity test results were zero, indicating low genotoxicity risk and a solid safety foundation.
Oleuropein is mainly found in olive fruits and leaves, especially in tissues rich in oleuropein content. In its natural state, oleuropein has a lower content and is more commonly used as an oxidation product of oleuropein or as a secondary metabolite formed during heat treatment. Oleuropein is one of the most abundant phenolic compounds in olives. After heating, acid-base, or enzymatic reactions, it can be converted into oleuropein.
The main extraction methods for oleuropein picric include solvent extraction, enzymatic hydrolysis and transformation, and heat treatment. Traditional organic solvent extraction mostly uses methanol, ethanol, or water-ethanol mixed solvents to improve the solubility of polar compounds. After purification processes such as concentration, liquid-liquid distribution, and column chromatography, the extract can obtain high-purity olivine picric acid. In recent years, emerging technologies such as ultrasound-assisted extraction, microwave-assisted extraction, and supercritical fluid extraction have also been applied to improve extraction efficiency and purity.
Additionally, by utilizing biotransformation technology, specific enzymes (such as β-glucosidase) catalyze the hydrolysis and oxidation of oleuropein to produce oleuropein, making it a green and efficient production pathway. This method not only improves product purity but also lays the foundation for large-scale production.
Pharmacological studies on the pharmacological activity of oleopicside mainly focus on its antioxidant, anti-inflammatory, anti-atherosclerosis, and cardiovascular protective effects. Numerous in vitro and in vivo experiments have shown that oleuropein can effectively eliminate free radicals and reduce oxidative stress, thereby protecting vascular endothelial cell function and inhibiting lipid peroxidation and inflammatory responses.
Oleuropein contains a rich phenolic hydroxyl structure, giving it powerful free radical scavenging ability. Experiments on free radical scavenging such as DPPH and ABTS have shown significant antioxidant activity. Its antioxidant mechanisms include direct electron transfer, action of hydrogen donors, and inducing the expression of endogenous antioxidant enzymes (such as superoxide dismutase SOD and glutathione peroxidase GPx).
Oleuropein regulates lipid metabolism and inflammatory responses through multiple targets, exerting anti-atherosclerosis effects. Its main targets include LOX-1 (oxidized low-density lipoprotein receptor 1), AMPK (5' AMP-activated protein kinase), and ABCA1 (ATP-binding box transporter A1). By inhibiting LOX-1-mediated oxidized low-density lipoprotein (ox-LDL) endocytosis, vascular endothelial cell damage is reduced; Activates the AMPK signaling pathway, promoting lipid metabolism and energy homeostasis; Enhances ABCA1 expression, enhances cholesterol efflux, and reduces arterial wall lipid deposition.
Oleuropein can inhibit the expression of pro-inflammatory factors such as TNF-α and IL-6, reducing vascular inflammatory responses. At the same time, it regulates the expression of apoptosis-related proteins MCL1 and BCL2, protecting vascular endothelial cells from apoptotic damage induced by oxidative stress and maintaining vascular stability.
Some studies suggest that oleuropein regulates the DNA repair enzyme RECQ1 and may be involved in maintaining genome stability. Additionally, its effect on the epigenetic regulator enzyme EHMT2 (histone methyltransferase) suggests its potential role in gene expression regulation and inflammatory responses.
The multi-target mechanism of oleoside is key to its pharmacological activity. The following is an analysis of the main targets and their mechanisms of action:
LOX-1 is the main receptor on the surface of vascular endothelial cells that recognizes and uptakes oxidized low-density lipoprotein, mediating the early pathological changes of atherosclerosis. Oleuropein inhibits LOX-1 expression and activity, reduces ox-LDL endocytosis and accumulation, alleviates endothelial cell damage and inflammatory responses, and blocks the process of atherosclerosis.
AMPK is a key regulatory enzyme for cellular energy metabolism, involved in lipid metabolism, glucose metabolism, and inflammation regulation. Oleuropein activates the AMPK signaling pathway, promotes fatty acid oxidation and cholesterol metabolism, inhibits lipid accumulation and inflammatory responses, thereby exerting anti-atherosclerosis effects.
ABCA1 is a key protein regulating intracellular cholesterol transport to high-density lipoprotein (HDL), aiding in cholesterol excretion and reverse cholesterol transport. Olivia picric acid upregulates ABCA1 expression, enhances cholesterol clearance, reduces lipid deposition on vascular walls, and alleviates atherosclerotic lesions.
Both MCL1 and BCL2 are apoptosis regulatory proteins that maintain cell survival and function. Oleuropein regulates its expression, inhibits oxidative stress-induced endothelial cell apoptosis, and protects vascular functional integrity.
EHMT2 is involved in the methylation modification of histone H3K9, regulating gene expression and inflammatory responses. The inhibitory effect of oleoside picrioside on EHMT2 may affect the expression of inflammation-related genes, reducing vascular inflammation.
RECQ1 is involved in DNA repair and genome stability maintenance. Olide oleotide's regulation of RECQ1 may help cells resist DNA damage induced by oxidative stress and protect vascular cell function.
Druggability evaluation of oliposide picric acid indicates it has certain potential for drug development. The molecular weight is 570.5 Da, slightly above the upper limit recommended by Lipinski's rule of 500 Da, but its good water solubility (12.69 mg/mL) and negative LogP value (-0.61) help with absorption and distribution in the body. A larger TPSA (238.97 Ų) suggests higher polarity, which may limit cell membrane permeability and oral bioavailability.
The low permeability of the blood-brain barrier reduces the risk of central nervous system side effects, but also limits its application in neurological diseases. Negative hERG channel inhibition and Ames test results indicate low cardiotoxicity and genotoxicity risks and good safety.
Regarding pharmacokinetics, there are few existing literature reports. It is speculated that its high polarity and water solubility may lead to limited intestinal absorption, with its distribution mainly concentrated in tissues rich in phenolic metabolic enzymes such as blood and liver. Oleuropein may undergo metabolic transformation through hepatic metabolic enzymes, but the metabolites and excretion pathways require further research.
With its multi-target antioxidant and anti-atherosclerotic activity, oleuropein has broad clinical application prospects. Its potential in preventing and treating cardiovascular diseases, especially atherosclerosis and related complications, is worth further exploration.
Future research should focus on the following directions:
Pharmacokinetics and dosage form optimization: Given its high polarity, suitable delivery routes and formulations, such as nanocarriers, liposomes, or sustained-release formulations, need to be developed to improve bioavailability and targeting.
In-depth mechanism analysis: Through multi-omics techniques and molecular simulation, the interaction mechanisms between oleuropein and target proteins are further revealed, clarifying its regulatory network for signaling pathways.
Safety and toxicology assessment: Systematically conduct long-term toxicological studies to evaluate safe dose ranges and potential side effects, providing a basis for clinical trials.
Clinical trial design: Based on existing pharmacological evidence, design a reasonable clinical study protocol to verify efficacy and safety in patients with cardiovascular diseases.
Combination drug research: Exploring the synergistic effects of oleuropein with existing lipid-lowering and anti-inflammatory drugs to optimize treatment regimens and improve clinical efficacy.
As an important derivative of natural olive polyphenols, oleuropein has become a research hotspot in the field of cardiovascular disease prevention and treatment due to its significant antioxidant, anti-inflammatory, and anti-atherosclerotic activities. Its multi-target regulatory mechanism provides a theoretical basis for the development of novel natural drugs. Although there are still certain challenges in pharmacokinetics and clinical applications, advances in extraction techniques and drug delivery systems suggest that oleuropein is expected to become a safe and effective cardiovascular protectant. In the future, it is necessary to strengthen basic research and clinical translation, promote its advancement toward clinical application, and bring new treatment options for cardiovascular disease patients.
Shenshuai
Wenjing
Hedandan
