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Oleuropein

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-O2002

  • Specification : 98%

  • CAS number : 32619-42-4

  • Formula : C25H32O13

  • Molecular Weight : 540.51

  • PUBCHEM ID : 5281544

  • Volume : 20mg

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Catalogue Number

BF-O2002

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

540.51

Appearance

Colorless crystal

Botanical Source

Cynomorium songaricum,Ligustrum lucidum,Ilex pubescens,Olea europaea,Syringa oblata

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC(=C(C=C3)O)O

Synonyms

Olive Leaf Extract/Oleuropein/oleuropein glucoside/Methyl (2S,3E,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylate/2H-Pyran-4-acetic acid, 3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, 2-(3,4-dihydroxyphenyl)ethyl ester, (2S,3E,4S)-

IUPAC Name

methyl (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

Density

1.5±0.1 g/cm3

Solubility

Methanol; Water

Flash Point

257.0±26.4 °C

Boiling Point

772.9±60.0 °C at 760 mmHg

Melting Point

89-90ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:32619-42-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31746508

Abstract

Olive (Olea europaea Linn., Fam. Oleaceae) is commonly known as Zaytoon in Mediterranean region. Its fruits and oil are essential components of Mediterranean diets. Olive tree is a prevalent plant species and one of the important cultivated crops of Mediterranean region. Oleuropein is a phenolic constituents of olive, which, along with its related compounds, has been indicated to be majorly responsible for its beneficial effects. Oleuropein is a secoiridoid type of phenolic compound and consists of three structural subunits: hydroxytyrosol, elenolic acid, and a glucose molecule. It is also reported to be the chemotaxonomic marker of olive. The oleuropein is reported to possess a number of biological activities including action against dyslipidemia, antiobesity, antidiabetic, antioxidant, antiatherogenic, antihypertensive, antiinflammatory, and hepatoprotective actions. The scientific evidence supports the role of oleuropein as a potential agent against metabolic syndrome. The present review discusses chemistry of oleuropein along with potential role of oleuropein with reference to pathophysiology of metabolic syndrome.

© 2019 John Wiley & Sons, Ltd.

KEYWORDS

Olea europaea L; cardiovascular disease; chemistry; diabetes; metabolic syndrome; obesity; oleuropein

Title

Oleuropein: A natural antioxidant molecule in the treatment of metabolic syndrome.

Author

Ahamad J1, Toufeeq I1, Khan MA2, Ameen MSM1, Anwer ET1, Uthirapathy S1, Mir SR3, Ahmad J4.

Publish date

2019 Dec

PMID

31450415

Abstract

A comprehensive structural characterization of the complex family of isomeric forms related to Oleuropein aglycone (OA) detected in virgin olive oil (VOO) was performed by reverse phase liquid chromatography with electrospray ionization and Fourier-transform mass spectrometry (RPLC-ESI-FTMS), integrated by enzymatic/chemical reactions performed on Oleuropein, the natural precursor of OA. First, some of the OA-related isomers typically observed in VOO extracts were generated upon enzymatic hydrolysis of the glycosidic linkage of Oleuropein. This step mimicked the process occurring during olive drupes crushing in the first stage of oil production. The incubation of the enzymatic reaction mixture at a more acidic pH was subsequently performed, to simulate the conditions of olive paste malaxation during oil production. As a result, further isomeric forms were generated and the complex chromatographic profile typically observed for OA in olive oil extracts, including at least 13 different peaks/bands/groups of peaks, was carefully reproduced. Each of those chromatographic features could be subsequently assigned to specific types of OA-related isomers, belonging to one of four structurally different classes. Specifically, diastereoisomers/geometrical isomers corresponding to two different types of open-structure forms and to as many types of closed-structure, di-hydropyranic forms of OA, characterized by the presence of one or two carbonyl groups, according to the case, were evidenced. In addition, the presence of stable enolic/dienolic tautomers, providing an indirect structural confirmation for some OA isomers, was ascertained through RPLC-ESI-FTMS analyses performed under H/D exchange conditions, i.e. in the presence of deuterated water as one of the mobile phase solvents.

Copyright © 2019 Elsevier B.V. All rights reserved.

KEYWORDS

H/D exchange; High resolution mass spectrometry; Oleuropein aglycone; Olive oil; Secoiridoids

Title

A comprehensive study of oleuropein aglycone isomers in olive oil by enzymatic/chemical processes and liquid chromatography-Fourier transform mass spectrometry integrated by H/D exchange.

Author

Abbattista R1, Losito I2, De Ceglie C1, Castellaneta A1, Calvano CD3, Palmisano F4, Cataldi TRI4.

Publish date

2019 Dec 1

PMID

31428230

Abstract

Oleuropein (OP) is a bioactive compound derived from plants of the genus Oleaceae exhibiting antitumor properties in several human cancers, including non-small-cell lung cancer (NSCLC). Recent evidence suggests that OP has proapoptotic effects on NSCLC cells via the mitochondrial apoptotic pathway. However, the exact molecular mechanisms behind the apoptogenic action of OP in NSCLC are still largely unknown. Glyoxalase 2 (Glo2) is an ancient enzyme belonging to the glyoxalase system involved in the detoxification of glycolysis-derived methylglyoxal. However, emerging evidence suggests that Glo2 may have also nonenzymatic roles in some malignant cells. In the present study, we evaluated whether and how Glo2 participated in the proapoptotic effects of OP in NSCLC A549 cells. Our results indicate that OP is able to induce apoptosis in A549 cells through the upregulation of mitochondrial Glo2 (mGlo2), mediated by the superoxide anion and Akt signaling pathway. Moreover, our data shows that the proapoptotic role of mGlo2, observed following OP exposure, occurs via the interaction of mGlo2 with the proapoptotic Bax protein. Conversely, OP does not alter the behavior of nonmalignant human BEAS-2B cells or mGlo2 expression, thus suggesting a specific anticancer role for this bioactive compound in NSCLC. Our data identify a novel pathway through which OP exerts a proapoptotic effect in NSCLC and suggest, for the first time, a novel, nonenzymatic antiapoptotic role for this ancient enzyme in NSCLC

Title

Oleuropein-Induced Apoptosis Is Mediated by Mitochondrial Glyoxalase 2 in NSCLC A549 Cells: A Mechanistic Inside and a Possible Novel Nonenzymatic Role for an Ancient Enzyme.

Author

Antognelli C1, Frosini R1, Santolla MF2, Peirce MJ1, Talesa VN1.

Publish date

2019 Jul 22


Description :

Oleuropein prevents oxidative myocardial injury induced by ischemia and reperfusion. PUMID/DOI:15302080 J Nutr Biochem. 2004 Aug;15(8):461-6. The protective effect of Oleuropein against the post-ischemic oxidative burst was investigated by measuring the release, in the coronary effluent, of oxidized glutathione, a sensitive marker of heart's exposure to oxidative stress. Reflow in ischemic hearts was accompanied by a prompt release of oxidized glutathione; in ischemic hearts pretreated with Oleuropein, this release was significantly reduced. Membrane lipid peroxidation was also prevented by Oleuropein. The reported data provide the first experimental evidence of a direct cardioprotective effect of Oleuropein in the acute events that follow coronary occlusion, likely because of its antioxidant properties. This finding strengthens the hypothesis that the nutritional benefit of olive oil in the prevention of coronary heart disease can be also related to the high content of Oleuropein and its derivatives. Moreover, our data, together with the well documented antithrombotic and antiatherogenic activity of olive oil polyphenols, indicate these antioxidants as possible therapeutic tools for the pharmacological treatment of coronary heart disease as well as in the case of cardiac surgery, including transplantation. Oleuropein induces apoptosis via activation of caspases and suppression of phosphatidylinositol 3-kinase/protein kinase B pathway in HepG2 human hepatoma cell line. PUMID/DOI:25634350 Mol Med Rep. 2015 Jun;11(6):4617-24. Oleuropein is a polyphenol, that is found in extra‑virgin olive oil. Previous studies have shown that Oleuropein inhibits cell proliferation and induces apoptosis in breast cancer, colorectal cancer and thyroid cancer. The aim of the present study was to investigate the effects of Oleuropein in hepatocellular carcinoma (HCC) cells. The results of Cell Counting Kit 8 and flow cytometric analysis indicated that Oleuropein effectively inhibited cell viability and induced apoptosis in HepG2 human hepatoma cells in a dose‑dependent manner, through activation of the caspase pathway. Proapoptotic Bcl‑2 family members, BAX and Bcl‑2, were involved in Oleuropein‑induced apoptosis. The phosphatidylinositol 3‑kinase/protein kinase B (PI3K/AKT) signaling pathway was also shown to be involved in this process. Oleuropein was demonstrated to suppress the expression of activated AKT. In addition, AKT overexpression promoted cell survival following treatment with Oleuropein, while inhibition of AKT promoted cell death. Furthermore, the data demonstrated that Oleuropein induces the production of reactive oxygen species (ROS) and that the function of Oleuropein is, at least partially, ROS‑dependent. These results suggest that Oleuropein may be a promising novel chemotherapeutic agent in hepatocellular carcinoma. Oleuropein suppresses LPS-induced inflammatory responses in RAW 264.7 cell and zebrafish. PUMID/DOI:25613688 J Agric Food Chem. 2015 Feb 25;63(7):2098-105. Oleuropein is one of the primary phenolic compounds present in olive leaf. In this study, the anti-inflammatory effect of Oleuropein was investigated using lipopolysaccharide (LPS)-stimulated RAW 264.7 and a zebrafish model. The inhibitory effect of Oleuropein on LPS-induced NO production in macrophages was supported by the suppression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). In addition, our enzyme immunoassay showed that Oleuropein suppressed the release of pro-inflammatory cytokines such as interleukin-1β (IL-1β) and interleukin-6 (IL-6). Oleuropein inhibited the translocation of p65 by suppressing phosphorylation of inhibitory kappa B-α (IκB-α). Oleuropein also decreased activation of ERK1/2 and JNK, which are associated with LPS-induced inflammation, and its downstream gene of AP-1. Furthermore, Oleuropein inhibited LPS-stimulated NO generation in a zebrafish model. Taken together, our results demonstrated that Oleuropein could reduce inflammatory responses by inhibiting TLR and MAPK signaling, and may be used as an anti-inflammatory agent. Antiviral efficacy against hepatitis B virus replication of oleuropein isolated from Jasminum officinale L. var. grandiflorum. PUMID/DOI:19580857 J Ethnopharmacol. 2009 Sep 7;125(2):265-8. RESULTS:Oleuropein (Ole) blocks effectively HBsAg secretion in HepG2 2.2.15 cells in a dose-dependent manner (IC(50)=23.2 microg/ml). Ole (80 mg/kg, intraperitoneally, twice daily) also reduced viremia in DHBV-infected ducks.CONCLUSION:Ole therefore warrants further investigation as a potential therapeutic agent for HBV infection. Hypoglycemic and antioxidant effect of oleuropein in alloxan-diabetic rabbits. PUMID/DOI:16236331 Life Sci. 2006 Feb 16;78(12):1371-7. Oleuropein, the active constituent of olive leaf (Olea europaea), has been endowed with many beneficial and health promoting properties mostly linked to its antioxidant activity. This study aimed to evaluate the significance of supplementation of Oleuropein in reducing oxidative stress and hyperglycemia in alloxan-induced diabetic rabbits. After induction of diabetes, a significant rise in plasma and erythrocyte malondialdehyde (MDA) and blood glucose as well as alteration in enzymatic and non-enzymatic antioxidants was observed in all diabetic animals. During 16 weeks of treatment of diabetic rabbits with 20 mg/kg body weight of Oleuropein the levels of MDA along with blood glucose and most of the enzymatic and non-enzymatic antioxidants were significantly restored to establish values that were not different from normal control rabbits. Untreated diabetic rabbits on the other hand demonstrated persistent alterations in the oxidative stress marker MDA, blood glucose and the antioxidant parameters. These results demonstrate that Oleuropein may be of advantage in inhibiting hyperglycemia and oxidative stress induced by diabetes and suggest that administration of Oleuropein may be helpful in the prevention of diabetic complications associated with oxidative stress.