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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 of OLEUROPEIN

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

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

ConditionModalityTargetsHighest PhaseProduct

PubMed

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
Record UNII
2O4553545L
Record Status Validated (UNII)
Record Version