Oleuropein

Oleuropein

Names
IUPAC name (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)- 2-tetrahydropyranyl]oxy]-4H-pyran-3-carboxylic acid, methyl ester
Identifiers
CAS Number	32619-42-4
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL1911053
ChemSpider	4444876
ECHA InfoCard	100.046.466
PubChem	5281544
InChI 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 Key: RFWGABANNQMHMZ-ZCHJGGQASA-N InChI=1/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 Key: RFWGABANNQMHMZ-ZCHJGGQABE
SMILES O=C(OCCc1ccc(O)c(O)c1)C[C@H]2C(=C/C)\[C@@H](O\C=C2\C(=O)OC)O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO
Properties
Chemical formula	C25H32O13
Molar mass	540.51 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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. All these compounds are tyrosol esters of elenolic acid that are further hydroxylated and glycosylated. It is one of the main natural phenols found in argan oil.^[1] It is also found in the leaves of privet.

Pharmacological properties

In preliminary laboratory research, oleuropein had activity as an agonist of the G-protein estrogen receptor.^[2]

Oleuropein inhibited the enzymatic activity of mammalian target of rapamycin (mTOR) with an IC₅₀ value of 905 nM, suggesting that mTOR inhibition is at least one of the reasons for the reported anti-cancer properties of oleuropein.^[3]

Other basic research is examining whether oleuropein has pharmacological properties.^[4] More research is needed to determine if these effects exist in humans.

Oleuropein is traditionally removed from olives due to its bitterness.

See also

• Hydroxytyrosol
• Oleocanthal
• Olive Leaf

References

1. Phenols and Polyphenols from Argania spinosa. Z. Charrouf and D. Guillaume, American Journal of Food Technology, 2007, 2, pages 679-683, doi:10.3923/ajft.2007.679.683
2. Prossnitz, Eric R.; Barton, Matthias (2014). "Estrogen biology: New insights into GPER function and clinical opportunities". Molecular and Cellular Endocrinology. 389 (1-2): 71–83. doi:10.1016/j.mce.2014.02.002. ISSN 0303-7207.
3. Taha, Mutasem O.; Khanfar, Mohammad A. (2014-07-20). "Oleuropein potently inhibits mammalian target of rapamycin: possible involvement of tandem anomeric hyperconjugation–Michael reaction". Medicinal Chemistry Research. 24 (2): 616–623. doi:10.1007/s00044-014-1168-9. ISSN 1054-2523.
4. Haris Omar, Syed (2010). "Oleuropein in Olive and its Pharmacological Effects". Scientia Pharmaceutica. 78 (2): 133–54. doi:10.3797/scipharm.0912-18. PMC 3002804. PMID 21179340.