Мы используем файлы cookie.
Продолжая использовать сайт, вы даете свое согласие на работу с этими файлами.
Phytochemical
Oleuropein
Другие языки:

    Oleuropein

    Подписчиков: 0, рейтинг: 0
    Oleuropein
    Oleuropein structure.svg
    Names
    IUPAC name
    Methyl (2S,3E,4S)-4-{2-[2-(3,4-Dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-(β-D-glucopyranosyloxy)-2H-pyran-5-carboxylate
    Systematic 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-carboxylate
    Other names
    2-(3,4-Dihydroxyphenyl)ethyl [(2S,3E,4S)-3-ethylidene-2-(β-D-glucopyranosyloxy)-5-(methoxycarbonyl)-3,4-dihydro-2H-pyran-4-yl]acetate
    Identifiers
    3D model (JSmol)
    ChEMBL
    ChemSpider
    ECHA InfoCard 100.046.466
    PubChem CID
    UNII
    • 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 checkY
      Key: RFWGABANNQMHMZ-ZCHJGGQASA-N checkY
    • 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
    • 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
    Properties
    C25H32O13
    Molar mass 540.518 g·mol−1
    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
    ☒N verify (what is checkY☒N ?)

    Oleuropein is a glycosylated seco-iridoid, a type of phenolic bitter compound found in green olive skin, flesh, seeds, and leaves. 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.

    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. 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.

    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).

    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.

    Enzymatic hydrolysis during the maturation of olives is also an important process for the decomposition of oleuropein and elimination of its bitter taste.

    Green olive blackening

    Green olives may be treated industrially with ferrous gluconate (0.4 wt. %) to change their color to black.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. Black olives treated with iron(II) gluconate are also depleted in hydroxytyrosol, as iron salts are catalysts for its oxidation.

    Research

    Oleuropein has been proposed as a proteasome activator.

    See also


    Новое сообщение