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Title:Izolacija in protolitsko ravnotežje punikalagina
Authors:ID Mladkovič, Maša (Author)
ID Hostnik, Gregor (Mentor) More about this mentor... New window
ID Frešer, Franjo (Comentor)
Files:.pdf UN_Mladkovic_Masa_2026.pdf (2,61 MB)
MD5: 26559F3FA286E6D17F734AA5A143A70A
 
Language:Slovenian
Work type:Bachelor thesis/paper
Typology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Engineering
Abstract:V diplomskem delu smo iz granatnega jabolka izolirali punikalagin in proučili njegovo protolitsko ravnotežje. Razvili analitsko metodo za spremljanje punikalagina v ekstraktu granatnega jabolka s tekočinsko kromatografijo visoke ločljivost. Iz olupkov granatnega jabolka smo z različnimi topili ekstrahirali različne polifenolne spojine. Največ punikalagina smo ekstrahirali z mešanico etanola in vode, nakisane z mravljično kislino. S preparativno kromatografijo smo nato v več korakih izolirali punikalagin in ocenili njegovo kromatografsko čistost, ki je bila 95,66 %. Njegovo istovetnost smo potrdili s primerjavo retencijskega časa z retencijskim časom standarda in analizo NMR. Punikalagin je bil prisoten v anomerih oblikah α in β, pri čemer je bil relativni delež α-PN 61,52 % in β-PN 38,48 %. Razmerje med α in β pa je 1,6:1,0. Nato smo raziskali stabilnost punikalagina s spektroskopijo UV-Vis in pokazali, da je stabilen vsaj eno uro do pH 7,14, medtem ko pri višjih pH pride do ireverzibilne oksidacije spojine. Spremljali smo njegovo ravnotežje s spektroskopijo UV-Vis ter izmerili spektre UV-Vis v območju pH 2–10. Pri največjih spremembah spektrov smo izrisali odvisnost absorbance oziroma valovne dolžine absorpcijskega vrha od pH. Pridobljene krivulje niso imele značilne sigmoidne oblike, značilne za deprotonacijo fenolnih skupin. S prileganjem sigmoidne funkcije določenim odsekom eksperimentalnih podatkov smo kljub temu poskušali ocenili vrednosti pKa skupine punikalagina. Z dokaj visoko zanesljivostjo nam je uspelo določiti le eno vrednost pKa.
Keywords:granatno jabolko, punikalagin, izolacija, protolitsko ravnotežje, spektroskopija UV Vis
Place of publishing:Maribor
Year of publishing:2026
PID:20.500.12556/DKUM-99982 New window
Publication date in DKUM:15.09.2026
Views:152
Downloads:6
Metadata:XML DC-XML DC-RDF
Categories:KTFMB - FKKT
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Licences

License:CC BY-NC-ND 4.0, Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International
Link:http://creativecommons.org/licenses/by-nc-nd/4.0/
Description:The most restrictive Creative Commons license. This only allows people to download and share the work for no commercial gain and for no other purposes.
Licensing start date:01.09.2026

Secondary language

Language:English
Title:Isolation and protolytic equilibrium of punicalagin
Abstract:In this thesis, punicalagin was isolated from pomegranate, and its protolytic equilibrium was investigated. An analytical high-performance liquid chromatography method was developed to monitor punicalagin in the pomegranate extract. Compounds were extracted from pomegranate peels using different solvents. The highest amount of punicalagin was extracted using a mixture of ethanol and water acidified with formic acid. Punicalagin was subsequently isolated in several steps using preparative chromatography, and its chromatographic purity was estimated to be 95.66 %. Its presence was confirmed by comparison with a standard and by NMR analysis. Punicalagin was present as the α- and β-anomers, with relative proportions of 61.52 % α-PN and 38.48 % β-PN, corresponding to an α-PN:β-PN ratio of 1.6:1.0. The stability of punicalagin was then investigated using UV-Vis spectroscopy. It was demonstrated that the compounds were stable for at least one hour at pH 7.14, whereas irreversible oxidation occurred at higher pH values. Its protolytic equilibrium was also monitored by UV-Vis spectroscopy, with spectra recorded over the pH range 2–10. In the spectral regions where the greatest changes were observed, absorbance or the wavelength of the absorption maximum was plotted against pH. The resulting curves did not exhibit a sigmoidal shape characteristic for the deprotonation of phenolic groups. By fitting a sigmoidal function to the segments of experimental data, several pKa values were estimated, while only one pKa value could be determined with sufficient precision.
Keywords:pomegranate, punicalagin, isolation, protolytic equilibrium, UV-Vis spectroscopy


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