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1. (Article ID: 12054)
Capozzi F, Piperno A, Uccella N
Oleuropein site selective hydrolysis by technomimetic nuclear magnetic resonance experiments
Journal of Agricultural and Food Chemistry 48(5) (2000)
1623-1629
Technomimetic NMR experiments were performed in accordance with the lye treatment adopted during table olive industrial procedures for the debittering process causing oleuropein degradation. The site selective hydrolysis of the two ester groups, characterizing the biophenolic secoiridoid molecule, was shown to be dependent on the different reactivities of these functionalities. The process is controlled by the experimental conditions exerted on the olive pulp and determined by the buffering capacity of the olive mesocarp and by the epicarp molecular components influencing the reactant penetration into the fruit pulp. The overall hydrolytic process of oleuropein, the bitter principle of olives, using the technomimetic experimental mode, gave rise to its catabolic derivatives, hydroxytyrosol, 11-methyloleoside, and the monoterpene glucoside, technomimetically produced, isolated, and structurally characterized by (1)H, (13)C, and COSY spectroscopy as the oleoside.
Basic oleuropein hydrolysis, technomimetic NMR experiments, biophenols and secoiridoids, table olive processing
NCBI PubMed ID: 10820069Publication DOI: 10.1021/jf991178bJournal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: n.uccella

unical.it
Institutions: CIRASAIA, Agrifood Research Centre, Università della Calabria, Arcavacata di Rende, Italy, Dipartimento Farmaco-chimico, Università, Messina, Italy
Methods: 13C NMR, 1H NMR, NMR-2D, alkaline hydrolysis, evaporation, flash chromatography
The publication contains the following compound(s):
- Compound ID: 30473
|
b-D-Glcp-(1-1)-+
|
3,4,8HOPhet-(8-7)-Subst
Subst = oleuropein aglycon core = SMILES C/C=C1[C@H](C{7}C(O)=O)C(C(OC)=O)=CO{1}[C@H]\1O |
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Structure type: monomer
Trivial name: oleuropein
Compound class: glycoside, phenolic glycoside, phenylethanoid glycoside, secoiridoid glycoside
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