Oleuropein

Oleuropein
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
PubChem	5281544
ChemSpider	4444876 Y
Jmol-3D images	Image 1
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
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 Y Key: RFWGABANNQMHMZ-ZCHJGGQASA-N Y 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
Properties
Molecular formula	C25H32O13
Molar mass	540.514
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Oleuropein is a chemical compound found in olive leaf from the olive tree (and leaves of privet) 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. Oleuropein and its metabolite hydroxytyrosol have powerful antioxidant activity both in vivo and in vitro and give extra-virgin olive oil its bitter, pungent taste. Oleuropein preparations have been claimed for several pharmacological effects^[1] among them^[2] strengthening of the immune system. A study in rats suggests oleuropein enhances thermogenesis by increasing the thermogenin content in brown adipose tissue and the secretion of noradrenaline and adrenaline.^[3]

See also

• Hydroxytyrosol
• Oleocanthal
• Olive Leaf

References

1. ^ Haris Omar, Syed (2010). "Oleuropein in Olive and its Pharmacological Effects". Scientia Pharmaceutica 78 (2): 133–54. doi:10.3797/scipharm.0912-18. 
2. ^ Sudjana, Aurelia N.; D’Orazio, Carla; Ryan, Vanessa; Rasool, Nooshin; Ng, Justin; Islam, Nabilah; Riley, Thomas V.; Hammer, Katherine A. (2009). "Antimicrobial activity of commercial Olea europaea (olive) leaf extract". International Journal of Antimicrobial Agents 33 (5): 461–3. doi:10.1016/j.ijantimicag.2008.10.026. PMID 19135874. 
3. ^ Oi-Kano, Yuriko; Kawada, Teruo; Watanabe, Tatsuo; Koyama, Fumihiro; Watanabe, Kenichi; Senbongi, Reijirou; Iwai, Kazuo (2008). "Oleuropein, a Phenolic Compound in Extra Virgin Olive Oil, Increases Uncoupling Protein 1 Content in Brown Adipose Tissue and Enhances Noradrenaline and Adrenaline Secretions in Rats". Journal of Nutritional Science and Vitaminology 54 (5): 363–70. doi:10.3177/jnsv.54.363. PMID 19001767. 

Further reading

• Tripoli, Elisa; Giammanco, Marco; Tabacchi, Garden; Di Majo, Danila; Giammanco, Santo; La Guardia, Maurizio (2009). "The phenolic compounds of olive oil: Structure, biological activity and beneficial effects on human health". Nutrition Research Reviews 18 (1): 98–112. doi:10.1079/NRR200495. PMID 19079898. 
• Walter Jr, WM; Fleming, HP; Etchells, JL (1973). "Preparation of antimicrobial compounds by hydrolysis of oleuropein from green olives". Applied microbiology 26 (5): 773–6. PMC 379900. PMID 4762396. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=379900. 
• Andreadou, Ioanna; Iliodromitis, Efstathios K.; Mikros, Emmanuel; Constantinou, Maria; Agalias, Apostolos; Magiatis, Prokopios; Skaltsounis, Alexios Leandros; Kamber, Elli et al. (2006). "The Olive Constituent Oleuropein Exhibits Anti-Ischemic, Antioxidative, and Hypolipidemic Effects in Anesthetized Rabbits". The Journal of Nutrition 136 (8): 2213–9. PMID 16857843. http://jn.nutrition.org/cgi/pmidlookup?view=long&pmid=16857843. 
• Leehuang, S; Huang, P; Zhang, D; Lee, J; Bao, J; Sun, Y; Chang, Y; Zhang, J et al. (2007). "Discovery of small-molecule HIV-1 fusion and integrase inhibitors oleuropein and hydroxytyrosol: Part I. Integrase inhibition". Biochemical and Biophysical Research Communications 354 (4): 872–8. doi:10.1016/j.bbrc.2007.01.071. PMC 2790717. PMID 17275783. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2790717. 
• Lee-Huang S, Huang P, Huang P (2004 July 11–16). "Anti-HIV activity of olive leaf extract and synergism with HAART". Int Conf AIDS 15th. Bangkok. http://gateway.nlm.nih.gov/MeetingAbstracts/ma?f=102283585.html.