Oleuropein

Oleuropein
IUPAC ime
 
(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 registarski broj 32619-42-4 DaY
PubChem[1][2] 5281544
ChemSpider[3] 4444876 DaY
ChEMBL[4] CHEMBL1911053
Jmol-3D slike Slika 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 DaY
Kod: RFWGABANNQMHMZ-ZCHJGGQASA-N DaY

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
Kod: RFWGABANNQMHMZ-ZCHJGGQABE

Svojstva
Molekulska formula C25H32O13
Molarna masa 540,51 g/mol

 DaY (šta je ovo?)   (verifikuj)

Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala

Infobox references

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.[5] 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,[6][7] 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.[8]

Reference

  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. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519.  edit
  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. ↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846.  edit
  4. ↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594.  edit
  5. ↑ 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
  6. ↑ Haris Omar, Syed (2010). „Oleuropein in Olive and its Pharmacological Effects”. Scientia Pharmaceutica 78 (2): 133–54. DOI:10.3797/scipharm.0912-18. 
  7. ↑ 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. 
  8. ↑ 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. 

Vidi još

Literatura

  • 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. 
  • Andreadou, Ioanna; Iliodromitis, Efstathios K.; Mikros, Emmanuel; Constantinou, Maria; Agalias, Apostolos; Magiatis, Prokopios; Skaltsounis, Alexios Leandros; Kamber, Elli i dr.. (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. 
  • Leehuang, S; Huang, P; Zhang, D; Lee, J; Bao, J; Sun, Y; Chang, Y; Zhang, J i dr.. (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. 
  • 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. 

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