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Merck
CN

SMB00810

Sigma-Aldrich

Oleocanthal

from Olea europaea

别名:

(-)-Oleocanthal

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关于此项目

经验公式(希尔记法):
C17H20O5
化学文摘社编号:
分子量:
304.34
UNSPSC代码:
12352205
NACRES:
NA.28
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生物来源

Olea europaea

方案

≥95%

表单

film

分子量

304.34

溶解性

DMSO: 1 mg/mL, clear, colorless

应用

metabolomics
vitamins, nutraceuticals, and natural products

运输

dry ice

储存温度

−20°C

SMILES字符串

O(CCc1ccc(cc1)O)C(=O)C[C@H](CC=O)\C(=C/C)\C=O

InChI

1S/C17H20O5/c1-2-14(12-19)15(7-9-18)11-17(21)22-10-8-13-3-5-16(20)6-4-13/h2-6,9,12,15,20H,7-8,10-11H2,1H3/b14-2-/t15-/m0/s1

InChI key

VPOVFCBNUOUZGG-VAKDEWRISA-N

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一般描述

Oleocanthal, a secoiridoid, a cyclopentane monoterpene, and a member of phenols, is a bioactive natural compound commonly derived from Olive oil (Olea europaea). Current research suggests that this metabolite acts as an inhibitor and may exhibit diverse biological activities, including anti-inflammatory, neuroprotective, apoptosis-inducing, antioxidant, antimalarial, and antineoplastic properties.

应用

Oleocanthal is a natural product derived from plant source that finds application in compound screening libraries, metabolomics, phytochemical, and drug discovery research.

生化/生理作用

Oleocanthal is one of the important polyphenols of olive oil well-known for its biological properties and health benefits. It exerts anti-inflammatory activity due to its dose-dependent inhibition of cyclooxygenase (COX-1, COX-2) enzymes in the prostaglandin biosynthesis in the same pathway as Ibuprofen. Oleocanthal is a potent anti-cancer agent, its treatment demonstrates inhibition of proliferation, migration, and invasion of various human breast cancer, prostate cancer, and multiple myeloma cells. In non-melanoma skin cancer, it reduces cell viability and migration, through inhibition of Erk and Akt phosphorylation and suppression of B-Raf expression. Oleocanthal was found to modulate estrogen receptor expression in luminal breast cancer and acts synergistically with tamoxifen treatment. It also elicits neuroprotective properties by inhibiting the formation of neurofibrillary tangles, a key hallmark in the pathogenesis of Alzheimer′s disease. Oleocanthal has also been reported to increase Amyloid-β transport across the blood-brain barrier via P-glycoprotein induction. It was found that it acts synergistically with Donepezil, an acetylcholine esterase inhibitor approved for use for all Alzheimer′s disease stages. Oleuropein displays anti-leishmanial activity when added in vitro and in vivo, in experimental models of Leishmania infection.

特点和优势

  • High quality compound suitable for multiple research applications
  • Compatible with HPLC and mass spectrometry techniques

其他说明

For additional information on our range of Biochemicals, please complete this form.

储存分类代码

10 - Combustible liquids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


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Olga S Koutsoni et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 47, 143-150 (2018-09-01)
Leishmaniasis is a neglected and emerging disease with varying clinical manifestations. The current treatment options rely on limited chemotherapy with serious drawbacks. Thus, there is an increasing interest in the identification of new candidates for designing potent, less toxic and
Kok-Lun Pang et al.
Nutrients, 10(5) (2018-05-08)
Oleocanthal is a minor constituent of olive oil with strong anti-inflammatory activities. Since the pathogenesis of many chronic diseases involves inflammatory and oxidative components, oleocanthal is a promising agent to prevent these conditions. This review aimed to summarise the current
Gary K Beauchamp et al.
Nature, 437(7055), 45-46 (2005-09-02)
Newly pressed extra-virgin olive oil contains oleocanthal--a compound whose pungency induces a strong stinging sensation in the throat, not unlike that caused by solutions of the non-steroidal anti-inflammatory drug ibuprofen. We show here that this similar perception seems to be
Limor Goren et al.
PloS one, 14(8), e0216024-e0216024 (2019-08-15)
(-)-Oleocanthal (oleocanthal) is a phenolic compound found in varying concentrations in extra virgin olive oil oleocanthal has been shown to be active physiologically, benefiting several diseased states by conferring anti-inflammatory and neuroprotective benefits. Recently, we and other groups have demonstrated
Elena E Tzekaki et al.
Breast cancer research and treatment, 186(2), 305-316 (2021-01-04)
Elevated expression of PAI-1 has been widely linked with adverse outcomes in a variety of human cancers, such as breast, gastric and ovarian cancers, rendering PAI-1 a prognostic biomarker. As a result, several chemical inhibitors are currently being developed against

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