Oleuropein

Oleuropein
Nazivi
	IUPAC naziv (4S,5E,6S)-4-[2-[2-(3,4-dihidroksifenil)etoksi]-2-oksoetil]-5-etiliden-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihidroksi-6-(hidroksimetil)-2-tetrahidropiranil]oksi]-4H-piran-3-karboksilna kiselina, metil estar
Identifikacija
CAS broj	32619-42-4 ;
3D model (Jmol)	interaktivna slika;
ChemSpider	4444876 ;
ECHA InfoCard	100.046.466
PubChem C ID	5281544;
	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; ; ; ; ; ;
Svojstva
Hemijska formula	C25H32O13
Molarna masa	540,51 g/mol
	Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa).
	verifikuj (šta je ?)
	Reference infokutije

Oleuropein je hemijsko jedinjenje pristno u maslinovom lišću. Ono se javlja zajedno sa blisko srodnim jedinjenjima kao što su 10-hidroksioleuropein, ligstrozid, i 10-hidroksiligstrozid. Sva ta jedinjenja su tirozolni estri elenolinske kiseline koja su dalje hidroksilovana i glikozilovana. On je jedan od glavnih prirodnih fenola prisutnih u arganskom ulju.^[3] On je takođe prisutan u lišću kaline.

Oleuropein i njegov metabolit hidroksitirozol imaju moćno antioksidansno dejstvo in vivo i in vitro. Oleuropein je jedno od jedinjenja koja daju ekstra devičanskom maslinovom ulju njegov gorak, opor ukus. Preparati oleuropeina imaju više farmakoloških dejstava,^[4]^[5] jedno od kojih je ojačavanje imunskog sistema. Ispitivanja na pacovima sugerišu da oleuropein pojačava termogenezu putem povišenaj sadržaja termogenina u smeđem adipoznom tkivu i sekreciju noradrenalina i adrenalina.^[6]

Reference уреди

^ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди
^ Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.
^ Charrouf, Z.; Guillaume, D. (2007). „Phenols and Polyphenols from Argania spinosa”. American Journal of Food Technology. 2 (7): 679—683. doi:10.3923/ajft.2007.679.683.
^ Haris Omar, Syed (2010). „Oleuropein in Olive and its Pharmacological Effects”. Scientia Pharmaceutica. 78 (2): 133—54. PMC 3002804  . PMID 21179340. doi:10.3797/scipharm.0912-18.
^ 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. PMID 19135874. doi:10.1016/j.ijantimicag.2008.10.026.
^ 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. PMID 19001767. doi:10.3177/jnsv.54.363.

Vidi još уреди

Literatura уреди

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. PMID 19079898. S2CID 221216561. doi:10.1079/NRR200495.
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. doi:10.1128/am.26.5.773-776.1973.
Andreadou, Ioanna; Iliodromitis, Efstathios K.; Mikros, Emmanuel; Constantinou, Maria; Agalias, Apostolos; Magiatis, Prokopios; Skaltsounis, Alexios Leandros; Kamber, Elli; Tsantili-Kakoulidou, Anna (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. doi:10.1093/jn/136.8.2213.
Leehuang, S; Huang, P; Zhang, D; Lee, J; Bao, J; Sun, Y; Chang, Y; Zhang, J; Huang, P (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. PMC 2790717  . PMID 17275783. doi:10.1016/j.bbrc.2007.01.071.
Lee-Huang S, Huang P, Huang P (11 July 2004—16). „Anti-HIV activity of olive leaf extract and synergism with HAART”. Int Conf AIDS 15th. Bangkok. Проверите вредност парамет(а)ра за датум: |date= (помоћ)

Spoljašnje veze уреди

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди

[2] Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.

[3] Charrouf, Z.; Guillaume, D. (2007). „Phenols and Polyphenols from Argania spinosa”. American Journal of Food Technology. 2 (7): 679—683. doi:10.3923/ajft.2007.679.683.

[Omar2010-4] Haris Omar, Syed (2010). „Oleuropein in Olive and its Pharmacological Effects”. Scientia Pharmaceutica. 78 (2): 133—54. PMC 3002804  . PMID 21179340. doi:10.3797/scipharm.0912-18.

[Sudjana2009-5] 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. PMID 19135874. doi:10.1016/j.ijantimicag.2008.10.026.

[6] 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. PMID 19001767. doi:10.3177/jnsv.54.363.

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