Oleuropein is a glycosylated seco-iridoid, a type of phenolic bitter compound found in green olive skin, flesh, seeds, and leaves.[1] The term oleuropein is derived from the botanical name of the olive tree, Olea europaea.
Because of its 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.[2][3]
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.[4] 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.[5][6]
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).[7][8]
The lye solution is replaced several times until the bitter taste has dissipated. An alternative process uses amberlite macroporous resins to trap the oleuropein directly from the solution, reducing waste water while capturing the extracted molecules.[9][10]
Enzymatic hydrolysis during the maturation of olives is also an important process for the decomposition of oleuropein and elimination of its bitter taste.[6][11]
Green olive blackeningedit
Green olives may be treated industrially with ferrous gluconate (0.4 wt. %)[7] to change their color to black.[12]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 ions form a black complex, giving the final color of the treated olives.[9][10][7] Black olives treated with iron(II) gluconate are also depleted in hydroxytyrosol, as iron salts are catalysts for its oxidation.[13]
^Rupp R. (1 July 2016). "The bitter truth about olives". National Geographic. from the original on 10 July 2019. Retrieved 24 June 2019.
^. California Olive Committee. 2017. Archived from the original on 5 August 2017. Retrieved 5 August 2017.
^Colmagro S.; Collins G.; Sedgley M. "Processing technology of the table olive" (PDF). (PDF) from the original on 9 August 2017. Retrieved 25 June 2019.
^Panizzi, L.; Scarpati, M.L.; Oriente, E.G. (1960). "Structure of the bitter glucoside oleuropein. Note II". Gazzetta Chimica Italiana. 90: 1449–1485.
^Yuan, Jiao-Jiao; Wang, Cheng-Zhang; Ye, Jian-Zhong; Tao, Ran; Zhang, Yu-Si (2015). "Enzymatic hydrolysis of oleuropein from Olea Europea (olive) leaf extract and antioxidant activities". Molecules. 20 (2): 2903–2921. doi:10.3390/molecules20022903. ISSN 1420-3049. PMC6272143. PMID 25679050.
^ abRamírez, Eva; Brenes, Manuel; García, Pedro; Medina, Eduardo; Romero, Concepción (2016). "Oleuropein hydrolysis in natural green olives: Importance of the endogenous enzymes" (PDF). Food Chemistry. 206: 204–209. doi:10.1016/j.foodchem.2016.03.061. hdl:10261/151764. ISSN 0308-8146. PMID 27041317. (PDF) from the original on 2018-07-23. Retrieved 2019-09-27.
^ abcEl-Makhzangy, Attya; Ramadan-Hassanien, Mohamed Fawzy; Sulieman, Abdel-Rahman Mohamed (2008). "Darkening of brined olives by rapid alkaline oxidation". Journal of Food Processing and Preservation. 32 (4): 586–599. doi:10.1111/j.1745-4549.2008.00198.x. ISSN 0145-8892.
^Ziena, H.M.S.; Youssef, M.M.; Aman, M.E. (1997). "Quality attributes of black olives as affected by different darkening methods". Food Chemistry. 60 (4): 501–508. doi:10.1016/S0308-8146(96)00354-8. ISSN 0308-8146.
^ ab"A 'greener' way to take the bitterness out of olives". phys.org. from the original on 23 June 2019. Retrieved 23 June 2019.
^ abJohnson, Rebecca; Mitchell, Alyson E. (2019). "Use of Amberlite macroporous resins to reduce bitterness in whole olives for improved processing sustainability". Journal of Agricultural and Food Chemistry. 67 (5): 1546–1553. doi:10.1021/acs.jafc.8b06014. ISSN 0021-8561. PMID 30636418. S2CID 58570570. from the original on 2020-06-26. Retrieved 2021-05-18.
^Restuccia, Cristina; Muccilli, Serena; Palmeri, Rosa; Randazzo, Cinzia L.; Caggia, Cinzia; Spagna, Giovanni (2011). "An alkaline β-glucosidase isolated from an olive brine strain of Wickerhamomyces anomalus". FEMS Yeast Research. 11 (6): 487–493. doi:10.1111/j.1567-1364.2011.00738.x. ISSN 1567-1356. PMID 21575132.
^Kumral, A.; Basoglu, F. (2008). "Darkening methods used in olive processing". Acta Horticulturae (791): 665–668. doi:10.17660/ActaHortic.2008.791.101. ISSN 0567-7572.
^Katsiki, Magda; Chondrogianni, Niki; Chinou, Ioanna; Rivett, A. Jennifer; Gonos, Efstathios S. (June 2007). "The olive constituent oleuropein exhibits proteasome stimulatory properties in vitro and confers life span extension of human embryonic fibroblasts". Rejuvenation Research. 10 (2): 157–172. doi:10.1089/rej.2006.0513. ISSN 1549-1684. PMID 17518699. from the original on 2020-11-15. Retrieved 2020-10-15.
^Zou, Ke; Rouskin, Silvia; Dervishi, Kevin; McCormick, Mark A.; Sasikumar, Arjun; Deng, Changhui; Chen, Zhibing; Kaeberlein, Matt; Brem, Rachel B.; Polymenis, Michael; Kennedy, Brian K. (2020-08-01). "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". Science Advances. 6 (32): eaba1306. Bibcode:2020SciA....6.1306Z. doi:10.1126/sciadv.aba1306. ISSN 2375-2548. PMC7406366. PMID 32821821.
November 16, 2023
oleuropein, glycosylated, seco, iridoid, type, phenolic, bitter, compound, found, green, olive, skin, flesh, seeds, leaves, term, oleuropein, derived, from, botanical, name, olive, tree, olea, europaea, namesiupac, name, methyl, dihydroxyphenyl, ethoxy, oxoeth. Oleuropein is a glycosylated seco iridoid a type of phenolic bitter compound found in green olive skin flesh seeds and leaves 1 The term oleuropein is derived from the botanical name of the olive tree Olea europaea Oleuropein NamesIUPAC name Methyl 2S 3E 4S 4 2 2 3 4 Dihydroxyphenyl ethoxy 2 oxoethyl 3 ethylidene 2 b D glucopyranosyloxy 2H pyran 5 carboxylateSystematic IUPAC name Methyl 2S 3E 4S 4 2 2 3 4 Dihydroxyphenyl ethoxy 2 oxoethyl 3 ethylidene 2 2S 3R 4S 5S 6R 3 4 5 trihydroxy 6 hydroxymethyl oxan 2 yl oxy 2H pyran 5 carboxylateOther names 2 3 4 Dihydroxyphenyl ethyl 2S 3E 4S 3 ethylidene 2 b D glucopyranosyloxy 5 methoxycarbonyl 3 4 dihydro 2H pyran 4 yl acetateIdentifiersCAS Number 32619 42 4 Y3D model JSmol Interactive imageChEMBL ChEMBL1911053 NChemSpider 4444876 YECHA InfoCard 100 046 466PubChem CID 5281544UNII 2O4553545L YCompTox Dashboard EPA DTXSID60905103InChI 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 YKey RFWGABANNQMHMZ ZCHJGGQASA N YInChI 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 s1Key RFWGABANNQMHMZ ZCHJGGQABESMILES 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 COPropertiesChemical formula C 25H 32O 13Molar mass 540 518 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Because of its 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 2 3 Contents 1 Chemical treatment 2 Green olive blackening 3 Research 4 See also 5 ReferencesChemical treatment editOleuropein 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 4 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 5 6 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 7 8 The lye solution is replaced several times until the bitter taste has dissipated An alternative process uses amberlite macroporous resins to trap the oleuropein directly from the solution reducing waste water while capturing the extracted molecules 9 10 Enzymatic hydrolysis during the maturation of olives is also an important process for the decomposition of oleuropein and elimination of its bitter taste 6 11 Green olive blackening editGreen olives may be treated industrially with ferrous gluconate 0 4 wt 7 to change their color to black 12 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 ions form a black complex giving the final color of the treated olives 9 10 7 Black olives treated with iron II gluconate are also depleted in hydroxytyrosol as iron salts are catalysts for its oxidation 13 Research editOleuropein has been proposed as a proteasome activator 14 15 See also editElenolic acid a marker for maturation of olives Hydroxytyrosol Ligstroside a closely related compound also found in olives Oleocanthal Olive leaf Olive Traditional fermentation and curingReferences edit Rupp R 1 July 2016 The bitter truth about olives National Geographic Archived from the original on 10 July 2019 Retrieved 24 June 2019 How olives are made California Olive Committee 2017 Archived from the original on 5 August 2017 Retrieved 5 August 2017 Colmagro S Collins G Sedgley M Processing technology of the table olive PDF Archived PDF from the original on 9 August 2017 Retrieved 25 June 2019 Panizzi L Scarpati M L Oriente E G 1960 Structure of the bitter glucoside oleuropein Note II Gazzetta Chimica Italiana 90 1449 1485 Yuan Jiao Jiao Wang Cheng Zhang Ye Jian Zhong Tao Ran Zhang Yu Si 2015 Enzymatic hydrolysis of oleuropein from Olea Europea olive leaf extract and antioxidant activities Molecules 20 2 2903 2921 doi 10 3390 molecules20022903 ISSN 1420 3049 PMC 6272143 PMID 25679050 a b Ramirez Eva Brenes Manuel Garcia Pedro Medina Eduardo Romero Concepcion 2016 Oleuropein hydrolysis in natural green olives Importance of the endogenous enzymes PDF Food Chemistry 206 204 209 doi 10 1016 j foodchem 2016 03 061 hdl 10261 151764 ISSN 0308 8146 PMID 27041317 Archived PDF from the original on 2018 07 23 Retrieved 2019 09 27 a b c El Makhzangy Attya Ramadan Hassanien Mohamed Fawzy Sulieman Abdel Rahman Mohamed 2008 Darkening of brined olives by rapid alkaline oxidation Journal of Food Processing and Preservation 32 4 586 599 doi 10 1111 j 1745 4549 2008 00198 x ISSN 0145 8892 Ziena H M S Youssef M M Aman M E 1997 Quality attributes of black olives as affected by different darkening methods Food Chemistry 60 4 501 508 doi 10 1016 S0308 8146 96 00354 8 ISSN 0308 8146 a b A greener way to take the bitterness out of olives phys org Archived from the original on 23 June 2019 Retrieved 23 June 2019 a b Johnson Rebecca Mitchell Alyson E 2019 Use of Amberlite macroporous resins to reduce bitterness in whole olives for improved processing sustainability Journal of Agricultural and Food Chemistry 67 5 1546 1553 doi 10 1021 acs jafc 8b06014 ISSN 0021 8561 PMID 30636418 S2CID 58570570 Archived from the original on 2020 06 26 Retrieved 2021 05 18 Restuccia Cristina Muccilli Serena Palmeri Rosa Randazzo Cinzia L Caggia Cinzia Spagna Giovanni 2011 An alkaline b glucosidase isolated from an olive brine strain of Wickerhamomyces anomalus FEMS Yeast Research 11 6 487 493 doi 10 1111 j 1567 1364 2011 00738 x ISSN 1567 1356 PMID 21575132 Kumral A Basoglu F 2008 Darkening methods used in olive processing Acta Horticulturae 791 665 668 doi 10 17660 ActaHortic 2008 791 101 ISSN 0567 7572 Vincenzo Marsilio Cristina Campestre Barbara Lanza July 2001 Phenolic compounds change during California style ripe olive processing Food Chemistry 74 1 55 60 doi 10 1016 S0308 8146 00 00338 1 Katsiki Magda Chondrogianni Niki Chinou Ioanna Rivett A Jennifer Gonos Efstathios S June 2007 The olive constituent oleuropein exhibits proteasome stimulatory properties in vitro and confers life span extension of human embryonic fibroblasts Rejuvenation Research 10 2 157 172 doi 10 1089 rej 2006 0513 ISSN 1549 1684 PMID 17518699 Archived from the original on 2020 11 15 Retrieved 2020 10 15 Zou Ke Rouskin Silvia Dervishi Kevin McCormick Mark A Sasikumar Arjun Deng Changhui Chen Zhibing Kaeberlein Matt Brem Rachel B Polymenis Michael Kennedy Brian K 2020 08 01 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 Science Advances 6 32 eaba1306 Bibcode 2020SciA 6 1306Z doi 10 1126 sciadv aba1306 ISSN 2375 2548 PMC 7406366 PMID 32821821 Retrieved from https en wikipedia org w index php title Oleuropein amp oldid 1183761196, wikipedia, wiki, book, books, library,
