OLEUROPEIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H32O13
Molecular Weight	540.5138
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]2(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC=C([C@@H](CC(=O)OCCC3=CC(O)=C(O)C=C3)\C2=C/C)C(=O)OC

InChI

InChIKey=RFWGABANNQMHMZ-ZCHJGGQASA-N

InChI=1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/b13-3+/t14-,18+,20+,21-,22+,24-,25-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C25H32O13
Molecular Weight	540.5138
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3002804/
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27928616 | https://www.ncbi.nlm.nih.gov/pubmed/21333710 | https://www.ncbi.nlm.nih.gov/pubmed/27916806 | https://www.ncbi.nlm.nih.gov/pubmed/26474288

Oleuropein is a phenylethanoid, a type of phenolic compound found in olive leaf together with other closely related compounds such as 10-hydroxyoleuropein, ligstroside, and 10-hydroxyligstroside. Oleuropein is traditionally removed from olives due to its bitterness. In preliminary laboratory research, oleuropein had activity as an agonist of the G-protein estrogen receptor. Oleuropein inhibited the enzymatic activity of mammalian target of rapamycin (mTOR), suggesting that mTOR inhibition is at least one of the reasons for the reported anti-cancer properties of oleuropein.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
In vitro evaluation of secoiridoid glucosides from the fruits of Ligustrum lucidum as antiviral agents.	2001 Nov	11724241
Olive oil and red wine antioxidant polyphenols inhibit endothelial activation: antiatherogenic properties of Mediterranean diet phytochemicals.	2003 Apr 1	12615669
Combining computational and biochemical studies for a rationale on the anti-aromatase activity of natural polyphenols.	2007 Dec	17910019
Acute doxorubicin cardiotoxicity is successfully treated with the phytochemical oleuropein through suppression of oxidative and nitrosative stress.	2007 Mar	17223128
Hypolipidimic and antioxidant activities of oleuropein and its hydrolysis derivative-rich extracts from Chemlali olive leaves.	2008 Nov 25	18823963
Mediterranean diet polyphenols reduce inflammatory angiogenesis through MMP-9 and COX-2 inhibition in human vascular endothelial cells: a potentially protective mechanism in atherosclerotic vascular disease and cancer.	2012 Nov 15	22595400

Patents

Sample Use Guides

In Vivo Use Guide

he effects of oleuropein was examined in rats with heart failure induced by permanent ligation of left coronary arteries. Twenty-four hours after the operation, the rats were assigned to five groups including a sham assigned to receive vehicle (1 ml/day) and four coronary ligated groups assigned to receive vehicle or oleuropein at 5, 10, or 20 mg/kg/day. Five weeks later, echocardiographic and hemodynamic parameters, serum concentrations of oxidative stress, and inflammatory markers were determined.

Route of Administration: Oral

In Vitro Use Guide

The minimum inhibitory concentration (expressed as MIC 90%) of oleuropein against C. Albicans ATCC 10231 was assessed using serial broth microdilution of oleuropein in RPMI 1640% + 2% glucose (w/v) from 25 mg/mL to 12.21 mkg/mL. Minimal inhibitory concentration (MIC) of oleuropein against C. albicans was 12.5 mg/ml

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:37:40 UTC 2023` Edited by `admin` on `Fri Dec 15 15:37:40 UTC 2023`
Record UNII	2O4553545L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OLEUROPEIN

Official Name

English

OLEUROPEIN [USP-RS]

Common Name

English

OLEOEUROPEIN

Common Name

English

2H-PYRAN-4-ACETIC ACID, 3-ETHYLIDENE-2-(.BETA.-D-GLUCOPYRANOSYLOXY)-3,4-DIHYDRO-5-(METHOXYCARBONYL)-, 2-(3,4-DIHYDROXYPHENYL)ETHYL ESTER, (2S-(2.ALPHA.,3E,4.BETA.))-

Common Name

English

2H-PYRAN-4-ACETIC ACID, 3-ETHYLIDENE-2-(.BETA.-D-GLUCOPYRANOSYLOXY)-3,4-DIHYDRO-5-(METHOXYCARBONYL)-, 2-(3,4-DIHYDROXYPHENYL)ETHYL ESTER, (2S,3E,4S)-

Common Name

English

2H-PYRAN-4-ACETIC ACID, 5-CARBOXY-3-ETHYLIDENE-2-(.BETA.-D-GLUCOSYLOXY)-3,4-DIHYDRO-, 3,4-DIHYDROXYPHENETHYL 5-METHYL ESTER

Common Name

English

OLEUROPEIN [INCI]

Common Name

English

Oleuropein [WHO-DD]

Common Name

English

OLEOEUROPEINE

Common Name

English

OLEUROPEIN [VANDF]

Common Name

English

OLEUROPEIN [MI]

Common Name

English

Classification Tree Code System Code

DSLD

2487 (Number of products:27)