Oleuropein: Difference between revisions

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|ImageFile=Oleuropein.

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|~~IUPACName~~= ~~<nowiki>~~(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)-

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|ImageSize=200px

2-tetrahydropyranyl]oxy]-4H-pyran-3-carboxylic acid, methyl ester</nowiki>

| IUPACName = Methyl (2''S'',3''E'',4''S'')-4-{2-[2-(3,4-Dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-(β-D-glucopyranosyloxy)-2''H''-pyran-5-carboxylate

|OtherNames=

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|= (,,)-4-2-[2-(3,4-)ethoxy]-2-oxoethyl--ethylidene--[(,,,,)-3,4,5-trihydroxy-6-(hydroxymethyl)-

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|Section1= {{Chembox Identifiers

| OtherNames = 2-(3,4-Dihydroxyphenyl)ethyl [(2''S'',3''E'',4''S'')-3-ethylidene-2-(β-D-glucopyranosyloxy)-5-(methoxycarbonyl)-3,4-dihydro-2''H''-pyran-4-yl]acetate

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| 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

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|Section1={{Chembox Identifiers

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| ~~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

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| 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

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| ~~InChIKey~~ = RFWGABANNQMHMZ-~~ZCHJGGQABE~~

| ~~StdInChI~~ = 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

| = /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

| ~~StdInChIKey~~ = RFWGABANNQMHMZ-~~ZCHJGGQASA-N~~

| = RFWGABANNQMHMZ-

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

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| = /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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

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| = RFWGABANNQMHMZ-

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=32619-42-4

| UNII_Ref = {{fdacite|correct|FDA}}

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| PubChem=5281544

| UNII = 2O4553545L

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| PubChem=5281544

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1911053

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID =4444876

}}

|Section2= {{Chembox Properties

|Section2={{Chembox Properties

| ~~Formula=~~C~~~~25~~~~H~~~~32~~~~O~~~~13~~~~

| C25H32O13

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| MolarMass=540.514

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| =

| ~~Density~~=

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|Section3= {{Chembox Hazards

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'''Oleuropein''' is a [[glycosylation|glycosylated]] seco-[[iridoid]], a type of [[polyphenol|phenolic]] bitter compound found in green [[olive]] skin, flesh, seeds, and leaves.<ref>{{cite web|url=https://www.nationalgeographic.com/people-and-culture/food/the-plate/2016/07/olives--the-bitter-truth/|author=Rupp R.|title=The bitter truth about olives|date=1 July 2016|work=National Geographic|access-date=24 June 2019|archive-date=10 July 2019|archive-url=https://web.archive.org/web/20190710080202/https://www.nationalgeographic.com/people-and-culture/food/the-plate/2016/07/olives--the-bitter-truth/|url-status=dead}}</ref> The term oleuropein is derived from the botanical name of the olive tree, ''Olea europaea''.

'''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]] [[ester]]s of [[elenolic acid]] that are further [[hydroxylation|hydroxylated]] and [[glycosylation|glycosylated]]. Oleuropein and its [[metabolite]] [[hydroxytyrosol]] have powerful [[antioxidant]] activity both ''[[in vivo]]'' and ''[[in vitro]]'' and give extra-virgin [[olive oil]] its [[bitter (taste)|bitter]], pungent [[taste]]. Oleuropein preparations have been claimed for several pharmacological effects<ref name="Omar2010">{{cite journal |pages=133–54 |doi=10.3797/scipharm.0912-18 |title=Oleuropein in Olive and its Pharmacological Effects |year=2010 |last1=Haris Omar |first1=Syed |journal=Scientia Pharmaceutica |volume=78 |issue=2}}</ref> among them<ref name="Sudjana2009">{{cite journal |pages=461–3 |doi=10.1016/j.ijantimicag.2008.10.026 |title=Antimicrobial activity of commercial Olea europaea (olive) leaf extract |year=2009 |last1=Sudjana |first1=Aurelia N. |last2=D’Orazio |first2=Carla |last3=Ryan |first3=Vanessa |last4=Rasool |first4=Nooshin |last5=Ng |first5=Justin |last6=Islam |first6=Nabilah |last7=Riley |first7=Thomas V. |last8=Hammer |first8=Katherine A. |journal=International Journal of Antimicrobial Agents |volume=33 |issue=5 |pmid=19135874}}</ref> 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]].<ref>{{cite journal |pages=363–70 |doi=10.3177/jnsv.54.363 |title=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 |year=2008 |last1=Oi-Kano |first1=Yuriko |last2=Kawada |first2=Teruo |last3=Watanabe |first3=Tatsuo |last4=Koyama |first4=Fumihiro |last5=Watanabe |first5=Kenichi |last6=Senbongi |first6=Reijirou |last7=Iwai |first7=Kazuo |journal=Journal of Nutritional Science and Vitaminology |volume=54 |issue=5 |pmid=19001767}}</ref>

Because of its [[Taste#Bitterness|bitter taste]], oleuropein must be completely removed or decomposed to make olives edible. During processing of bitter and inedible green olives for consumption as table olives, oleuropein is removed from olives via a number of methods, including by immersion in [[lye]].<ref>{{cite web|url=http://calolive.org/our-story/how-olives-are-made/|title=How olives are made|publisher=California Olive Committee|date=2017|access-date=5 August 2017|archive-url=https://web.archive.org/web/20170805183626/http://calolive.org/our-story/how-olives-are-made/|archive-date=5 August 2017|url-status=dead}}</ref><ref name="Colmagro">{{cite web |author1=Colmagro S. |author2=Collins G. |author3=Sedgley M. |title=Processing technology of the table olive |url=https://ucanr.edu/datastoreFiles/608-760.pdf |access-date=25 June 2019 |archive-date=9 August 2017 |archive-url=https://web.archive.org/web/20170809155640/http://ucanr.edu/datastoreFiles/608-760.pdf |url-status=live }}</ref>

==Chemical treatment==

Oleuropein is a derivative of [[elenolic acid]] linked to the orthodiphenol [[hydroxytyrosol]] by an [[ester bond]] and to a molecule of [[glucose]] by a [[glycosidic bond]].<ref name="Panizzi1960">{{cite journal|last1=Panizzi|first1=L.|last2=Scarpati|first2=M.L.|last3=Oriente|first3=E.G.|year=1960|title=Structure of the bitter glucoside oleuropein. Note II|journal=Gazzetta Chimica Italiana|volume=90|pages=1449–1485}}</ref> When olives are immersed in a lye solution, the alkaline conditions lead to hydrolysis of the ester bond. The basic conditions also significantly increases the [[solubility]] of these derivatives, facilitating their release into the [[lye]] solution.<ref name="YuanWang2015">{{cite journal|last1=Yuan|first1=Jiao-Jiao|last2=Wang|first2=Cheng-Zhang|last3=Ye|first3=Jian-Zhong|last4=Tao|first4=Ran|last5=Zhang|first5=Yu-Si|

title=Enzymatic hydrolysis of oleuropein from Olea Europea (olive) leaf extract and antioxidant activities|journal=Molecules|volume=20|issue=2|year=2015|pages=2903–2921|issn=1420-3049|doi=10.3390/molecules20022903|pmid=25679050|pmc=6272143|doi-access=free}}</ref><ref name="RamírezBrenes2016">{{cite journal|last1=Ramírez|first1=Eva|last2=Brenes|first2=Manuel|last3=García|first3=Pedro|last4=Medina|first4=Eduardo|last5=Romero|first5=Concepción|title=Oleuropein hydrolysis in natural green olives: Importance of the endogenous enzymes|journal=Food Chemistry|volume=206|year=2016|pages=204–209|issn=0308-8146|doi=10.1016/j.foodchem.2016.03.061|pmid=27041317|hdl=10261/151764|url=https://digital.csic.es/bitstream/10261/151764/1/Postprint_2016_FoodChem_V206_P204.pdf|hdl-access=free|access-date=2019-09-27|archive-date=2018-07-23|archive-url=https://web.archive.org/web/20180723221236/http://digital.csic.es/bitstream/10261/151764/1/Postprint_2016_FoodChem_V206_P204.pdf|url-status=live}}</ref>

The high pH accelerates the oxidation of the phenolics, leading to blackness, as during their normal ripening, if the solution is oxygenated by air injection (alkaline oxidation of olives is also called the ''California process'').<ref name="El-Makhzangy2008">{{cite journal|last1=El-Makhzangy|first1=Attya|last2=Ramadan-Hassanien|first2=Mohamed Fawzy|last3=Sulieman|first3=Abdel-Rahman Mohamed|title=Darkening of brined olives by rapid alkaline oxidation|journal=Journal of Food Processing and Preservation|volume=32|issue=4|year=2008|pages=586–599|issn=0145-8892|doi=10.1111/j.1745-4549.2008.00198.x|doi-access=free}}</ref><ref name="ZienaYoussef1997">{{cite journal|last1=Ziena|first1=H.M.S.|last2=Youssef|first2=M.M.|last3=Aman|first3=M.E.|title=Quality attributes of black olives as affected by different darkening methods|journal=Food Chemistry|volume=60|issue=4|year=1997|pages=501–508|issn=0308-8146|doi=10.1016/S0308-8146(96)00354-8}}</ref>

The lye solution is replaced several times until the bitter taste has dissipated. An alternative process uses [[amberlite]] macroporous [[resin]]s to trap the oleuropein directly from the solution, reducing waste water while capturing the extracted molecules.<ref name="physorg2019">{{cite web|url=https://phys.org/news/2019-01-greener-bitterness-olives.html|title=A 'greener' way to take the bitterness out of olives|work=phys.org|access-date=23 June 2019|archive-date=23 June 2019|archive-url=https://web.archive.org/web/20190623104729/https://phys.org/news/2019-01-greener-bitterness-olives.html|url-status=live}}</ref><ref name="JohnsonMitchell2019">{{cite journal|last1=Johnson|first1=Rebecca|last2=Mitchell|first2=Alyson E.|title=Use of Amberlite macroporous resins to reduce bitterness in whole olives for improved processing sustainability|journal=Journal of Agricultural and Food Chemistry|volume=67|issue=5|year=2019|pages=1546–1553|issn=0021-8561|doi=10.1021/acs.jafc.8b06014|pmid=30636418|s2cid=58570570|url=http://www.escholarship.org/uc/item/2sg8n70x|access-date=2021-05-18|archive-date=2020-06-26|archive-url=https://web.archive.org/web/20200626231400/https://escholarship.org/uc/item/2sg8n70x|url-status=live}}</ref>

Enzymatic hydrolysis during the maturation of olives is also an important process for the decomposition of oleuropein and elimination of its bitter taste.<ref name="RamírezBrenes2016" /><ref name="RestucciaMuccilli2011">{{cite journal|last1=Restuccia|first1=Cristina|last2=Muccilli|first2=Serena|last3=Palmeri|first3=Rosa|last4=Randazzo|first4=Cinzia L.|last5=Caggia|first5=Cinzia|last6=Spagna|first6=Giovanni|title=An alkaline β-glucosidase isolated from an olive brine strain of Wickerhamomyces anomalus|journal=FEMS Yeast Research|volume=11|issue=6|year=2011|pages=487–493|issn=1567-1356|doi=10.1111/j.1567-1364.2011.00738.x|pmid=21575132|doi-access=free}}</ref>

==Green olive blackening==

Green olives may be treated industrially with [[Iron(II) gluconate|ferrous gluconate]] (0.4 wt. %)<ref name="El-Makhzangy2008" /> to change their color to black.<ref name="KumralBasoglu2008">{{cite journal|last1=Kumral|first1=A.|last2=Basoglu|first2=F.|title=Darkening methods used in olive processing|journal=Acta Horticulturae|issue=791|year=2008|pages=665–668|issn=0567-7572|doi=10.17660/ActaHortic.2008.791.101}}</ref> [[Gluconate]], an edible oxidation product of glucose, is used as non-toxic reactant to maintain Fe2+ in solution. When in contact with polyphenols, the [[ferrous ion]]s form a black complex, giving the final color of the treated olives.<ref name="physorg2019" /><ref name="JohnsonMitchell2019" /><ref name="El-Makhzangy2008" /> Black olives treated with [[iron(II) gluconate]] are also depleted in [[hydroxytyrosol]], as iron salts are [[catalysis|catalysts]] for its oxidation.<ref name="Marsilio2001">{{cite journal |doi=10.1016/S0308-8146(00)00338-1 |title=Phenolic compounds change during California-style ripe olive processing |author1=Vincenzo Marsilio |author2=Cristina Campestre |author3=Barbara Lanza |journal=Food Chemistry |volume =74 | issue =1 |date= July 2001 |pages= 55–60}}</ref>

== Research ==

Oleuropein has been proposed as a [[proteasome]] activator.<ref>{{Cite journal|last1=Katsiki|first1=Magda|last2=Chondrogianni|first2=Niki|last3=Chinou|first3=Ioanna|last4=Rivett|first4=A. Jennifer|last5=Gonos|first5=Efstathios S.|date=June 2007|title=The olive constituent oleuropein exhibits proteasome stimulatory properties in vitro and confers life span extension of human embryonic fibroblasts|url=https://pubmed.ncbi.nlm.nih.gov/17518699/|journal=Rejuvenation Research|volume=10|issue=2|pages=157–172|doi=10.1089/rej.2006.0513|issn=1549-1684|pmid=17518699|access-date=2020-10-15|archive-date=2020-11-15|archive-url=https://web.archive.org/web/20201115110544/https://pubmed.ncbi.nlm.nih.gov/17518699/|url-status=live}}</ref><ref>{{Cite journal|last1=Zou|first1=Ke|last2=Rouskin|first2=Silvia|last3=Dervishi|first3=Kevin|last4=McCormick|first4=Mark A.|last5=Sasikumar|first5=Arjun|last6=Deng|first6=Changhui|last7=Chen|first7=Zhibing|last8=Kaeberlein|first8=Matt|last9=Brem|first9=Rachel B.|last10=Polymenis|first10=Michael|last11=Kennedy|first11=Brian K.|date=2020-08-01|title=Life span extension by glucose restriction is abrogated by methionine supplementation: Cross-talk between glucose and methionine and implication of methionine as a key regulator of life span|url= |journal=Science Advances|language=en|volume=6|issue=32|pages=eaba1306|doi=10.1126/sciadv.aba1306|pmid=32821821|pmc=7406366|bibcode=2020SciA....6.1306Z |issn=2375-2548|doi-access=free}}</ref>

== See also ==

* [[Elenolic acid]] (a marker for maturation of olives)

* [[Hydroxytyrosol]]

* [[Ligstroside]], a closely related compound also found in olives

* [[Oleocanthal]]

* [[Olive ~~Leaf~~]]

* [[Olive ]]

* [[Olive#Traditional fermentation and curing|Olive: Traditional fermentation and curing]]

==References==

== Further reading ==

*{{cite journal |pages=98–112 |doi=10.1079/NRR200495 |title=The phenolic compounds of olive oil: Structure, biological activity and beneficial effects on human health |year=2009 |last1=Tripoli |first1=Elisa |last2=Giammanco |first2=Marco |last3=Tabacchi |first3=Garden |last4=Di Majo |first4=Danila |last5=Giammanco |first5=Santo |last6=La Guardia |first6=Maurizio |journal=Nutrition Research Reviews |volume=18 |pmid=19079898 |issue=1}}

*{{cite journal |pmid=4762396 |pmc=379900 |year=1973 |last1=Walter Jr |first1=WM |last2=Fleming |first2=HP |last3=Etchells |first3=JL |title=Preparation of antimicrobial compounds by hydrolysis of oleuropein from green olives |volume=26 |issue=5 |pages=773–6 |journal=Applied microbiology }}

*{{cite journal |first1=Ioanna |last1=Andreadou |first2=Efstathios K. |first3=Emmanuel |last3=Mikros |first4=Maria |last4=Constantinou |first5=Apostolos |last5=Agalias |first6=Prokopios |last6=Magiatis |first7=Alexios Leandros |last7=Skaltsounis |first8=Elli |last8=Kamber |first9=Anna |last9=Tsantili-Kakoulidou |title=The Olive Constituent Oleuropein Exhibits Anti-Ischemic, Antioxidative, and Hypolipidemic Effects in Anesthetized Rabbits |journal=The Journal of Nutrition |pmid=16857843 |url=http://jn.nutrition.org/cgi/pmidlookup?view=long&pmid=16857843 |year=2006 |last2=Iliodromitis |volume=136 |issue=8 |pages=2213–9}}

*{{cite journal |pages=872–8 |doi=10.1016/j.bbrc.2007.01.071 |pmc=2790717 |title=Discovery of small-molecule HIV-1 fusion and integrase inhibitors oleuropein and hydroxytyrosol: Part I. Integrase inhibition |year=2007 |last1=Leehuang |first1=S |last2=Huang |first2=P |last3=Zhang |first3=D |last4=Lee |first4=J |last5=Bao |first5=J |last6=Sun |first6=Y |last7=Chang |first7=Y |last8=Zhang |first8=J |last9=Huang |first9=P |journal=Biochemical and Biophysical Research Communications |volume=354 |issue=4 |pmid=17275783 }}

*{{cite conference |author=Lee-Huang S, Huang P, Huang P |title=Anti-HIV activity of olive leaf extract and synergism with HAART |booktitle=Int Conf AIDS 15th |pages= |publisher=|date=2004 July 11–16 |location=Bangkok |url=http://gateway.nlm.nih.gov/MeetingAbstracts/ma?f=102283585.html }}

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[[Category:]]

[[Category:Phenol antioxidants]]

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[[Category:~~Antioxidants~~]]

[[Category:Anti-inflammatory agents]]

[[Category:~~Catechols~~]]

[[Category:]]

[[Category:~~Carboxylate~~ ~~esters~~]]

[[Category: ]]

[[Category:~~Natural phenol glycosides~~]]

[[Category:]]

[[Category:Olives]]

[[Category:Olive oil]]

[[ca:Oleuropeïna]]

[[Category:Phytochemicals]]

[[es:Oleuropeína]]

[[Category:Methyl esters]]

[[it:Oleuropeina]]

[[ja:オレウロペイン]]