Unit:
Κατεύθυνση Οργανική Σύνθεση και Εφαρμογές της στη Χημική ΒιομηχανίαLibrary of the School of Science
Author:
Dalalaki Aikaterini
Supervisors info:
Αθανάσιος Γκιμήσης, Καθηγητής, Τμήμα Χημείας, ΕΚΠΑ
Δημήτριος Γεωργιάδης, Αναπληρωτής Καθηγητής, Τμήμα Χημείας, ΕΚΠΑ
Βικτώρια Μαγκριώτη, Αναπληρώτρια Καθηγήτρια, Τμήμα Χημείας, ΕΚΠΑ
Original Title:
Ημισύνθεση Σεκοϊριδοειδών Φυσικών Προϊόντων από Ελαιοευρωπεΐνη
Translated title:
Semisynthesis of Secoiridoid Natural Products from Oleuropein
Summary:
Oleuropein (OLE), a natural secoiridoid glucoside and main
polyphenolic constituent of the Mediterranean Olive tree (Olea europaea), as
well as the aglyca such as oleacin and oleocanthal belonging in the same
family of secoiridoids, have been shown by numerous studies that possess a
variety of biological activity with particular interest to their anticancer,
cardioprotectant, antiflamatory and antidiabetic properties. OLE is isolated
from olive leaves with particular ease and in high yield for a natural product.
For this reason it constitutes, especially in Greece, a readily available starting
material available for semisynthetic studies.
In this study, the chemical reactivity of OLE was studied with the purpose of
increasing the added value of a less used part of the olive tree, which, due to
its fruit, plays a central role in Greek economy. For this purpose, the reactions
of enzymatic hydrolysis and acid methanolysis of OLE were studied and in
addition, a synthetic scheme was designed and executed successfully for the
chemical conversion of OLE to other related natural and unnatural
secoiridoids. In the enzymatic hydrolysis of OLE, it was determined for the
first time that the 8R,9S-diastereomer of the monoaldehyde is the kinetic
product, whereas the 8S,9S-diastereomer is the most stable thermodynamic
product. In the acid methanolysis of OLE, the stereochemistry of the products
was determined and was compared to recent bibliographic data.
Main subject category:
Science
Keywords:
olea europaea, natural products, secoiridoids, oleuropein, semi-synthesis
Number of references:
110
File:
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LIBRARY.pdf
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File access is restricted until 2027-09-12.
