Oleocanthal
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Oleocanthal is an orally active phenolic seciridoid compound. Oleocanthal can be extracted from olive oil. Oleocanthal inhibits COX-1 and COX-2, reduces ROS and NO, and upregulates Nrf-2 and HO-1. Oleocanthal reduces Aβ deposition. Oleocanthal exhibits anti-Leishmania activity against promastigotes and amastigotes of L. major, with IC50 values of 18.7 and 87 μg/mL, respectively. Oleocanthal exhibits anticancer activity against colon, breast, liver, and melanoma cancers. Oleocanthal also exhibits anti-inflammatory and neuroprotective properties. Oleocanthal can be used in Alzheimer's disease research.
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- Pureza: 95.04%
- No. CAS: 289030-99-5
- Fòrmula: C17H20O5
- Peso molecular:304.34
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Almacenamiento:
-20°C, protect from light, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)
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Actividad biológica
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Chemical Information
- Pureza y Documentación
- Referencias
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Help & FAQs
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Actividad biológica
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COX-1 |
COX-2 |
Leishmania |
HO-1 |
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| A549 | IC50 |
10 μM
Compound: 50
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Antiproliferative activity against human A549 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay
Antiproliferative activity against human A549 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay
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[PMID: 38733884] |
| MDA-MB-231 | IC50 |
15 μM
Compound: 1
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Cytotoxicity against human MDA-MB-231 cells after 24 hrs by MTT assay
Cytotoxicity against human MDA-MB-231 cells after 24 hrs by MTT assay
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[PMID: 23403296] |
| MDA-MB-231 | IC50 |
7.5 μM
Compound: 1
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Antimigratory activity against human MDA-MB-231 cells after 24 hrs by wound healing assay
Antimigratory activity against human MDA-MB-231 cells after 24 hrs by wound healing assay
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[PMID: 23403296] |
| NCI-H322M | IC50 |
26.3 μM
Compound: 50
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Antiproliferative activity against human NCI-H322M cells assessed as cell growth inhibition incubated for 72 hrs by MTT assay
Antiproliferative activity against human NCI-H322M cells assessed as cell growth inhibition incubated for 72 hrs by MTT assay
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[PMID: 38733884] |
Oleocanthal (25-100 μM) reduces ROS, nitrites, and pro-inflammatory cytokines levels in LPS-stimulated murine peritoneal macrophages[1].
Oleocanthal (1-25 μM; 12 h) decreases LPS-induced NOS2 synthesis and NO production in ATDC-5 chondrocytes[2].
Oleocanthal (0-200 μg/mL; 48-60 h) inhibits the growth of L. major promastigotes and amastigotes, presenting IC50 values of 18.7 and 87 μg/mL, respectively[5].
Oleocanthal shows inhibitory activity against COX-1 and COX-2 enzymes[6].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:murine peritoneal macrophages
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Concentration:25 μM, 50 μM, 100 μM
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Incubation Time:30 min
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Result:Upregulated protein expression of Nrf-2 (25 μM: 1.57; 50 μM: 1.54; 100 μM: 1.63) and HO-1 (25 μM: 2.12; 50 μM: 2.24; 100 μM: 1.92).
Oleocanthal (5 mg/kg b.w.; i.p.; 3 times/week; 16 total doses) suppresses footpad thickness, decreases parasite load, and induces Th1-type immunity in L. major-infected BALB/c mice[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Male wild-type C57BL/6J and 5xFAD mice (4 and 9 months of age)[3]
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Dosage:10 mg/kg
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Administration:Oral gavage, daily, for 3 months
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Result:Improved metabolic parameters (body weight, food and water intake, energy expenditure, etc.) and behavioral parameters (sleep patterns, anxiety-like behavior).
Reduced brain Aβ levels and IgG extravasation (improved BBB function).
Increased sleep hours and decreased movement related to anxiety-like behavior.
| NCT Number | Sponsor | Condition | Start Date |
Phase
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|---|---|---|---|---|
| NCT01329991 | Plexxikon| | 2011-05 | PHASE1 |
Chemical Information
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No. CAS 289030-99-5
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Appearance Solid
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Peso molecular 304.34
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Fòrmula C17H20O5
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Color White to off-white
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SMILES
C/C=C([C@H](CC(OCCC1=CC=C(C=C1)O)=O)CC=O)/C=O
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Structure Classification
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Initial Source
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
-20°C, protect from light, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)
Pureza y Documentación
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Ficha de datos (273 KB)
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SDS (394 KB)
- English - EN (394 KB)
- Français - FR (394 KB)
- Deutsch - DE (394 KB)
- Norwegian - NO (394 KB)
- Español - ES (394 KB)
- Swedish - SV (394 KB)
- Italian - IT (394 KB)
- Korean - KR (394 KB)
- Portuguese - PT (394 KB)
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Instrucciones de manejo (2659 KB)
Referencias
[1]. Montoya T, et al. Oleocanthal Modulates LPS-Induced Murine Peritoneal Macrophages Activation via Regulation of Inflammasome, Nrf-2/HO-1, and MAPKs Signaling Pathways. J Agric Food Chem. 2019 May 15;67(19):5552-5559. [Content Brief]
[2]. Iacono A, et al. Effect of oleocanthal and its derivatives on inflammatory response induced by lipopolysaccharide in a murine chondrocyte cell line. Arthritis Rheum. 2010 Jun;62(6):1675-82. [Content Brief]
[3]. Yang E, et al. Oleocanthal Ameliorates Metabolic and Behavioral Phenotypes in a Mouse Model of Alzheimer's Disease. Molecules. 2023 Jul 23;28(14):5592. [Content Brief]
[5]. Karampetsou K, et al. Exploring the Immunotherapeutic Potential of Oleocanthal against Murine Cutaneous Leishmaniasis. Planta Med. 2022 Aug;88(9-10):783-793. [Content Brief]
[6]. Costa V, et al. Anti-Inflammatory Activity of Olive Oil Polyphenols-The Role of Oleacein and Its Metabolites. Biomedicines. 2022 Nov 21;10(11):2990. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
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