Unit:
Κατεύθυνση Οργανική Σύνθεση και Εφαρμογές της στη Χημική ΒιομηχανίαLibrary of the School of Science
Supervisors info:
Αθανάσιος Γκιμήσης, Καθηγητής Τμήμα Χημείας ΕΚΠΑ,(Επιβλέπων),
Θωμάς Μαυρομούστακος, Καθηγητής Τμήμα Χημείας ΕΚΠΑ,
Δημήτρης Γεωργιάδης, Καθηγητής Τμήμα Χημείας ΕΚΠΑ
Original Title:
Σύνθεση των Σεκοϊριδοειδών Φυσικών Προϊόντων Syringoleosides Α, Β και F από Ελαιοευρωπαΐνη.
Translated title:
Synthesis of secoroidoids natural products Syringoleosides A, B and F from oleuropein.
Summary:
Syringoleosides A-H are secoiridoid natural products that were recently isolated and characterized from the flowers of Syringa Dilatata, a native shrub to Korea. Of these, syringoleosides A, B and F exhibited interesting biological activity. They could be described as esters of the 7-carboxylate of 11-methyloleoside with the 6-hydroxyl of three specific glycosides. These structures are reminiscent of nuezhenide, an abundant and well-studied secoiridoid natural product. The limited availability of these interesting compounds from natural sources has prompted the exploration of alternative synthetic approaches.
In the present study, an efficient semi-synthetic approach for the rapid synthesis of those molecules and derivatives thereof, is presented. It utilizes oleuropein, as a starting material, readily isolated in good yields from olive leaves. The developed synthetic methodology comprises of a series of robust synthetic protocols including carefully chosen protection and deprotection strategies that has already provided access to nuezhenide and in this study were applied to the synthesis of syringoleoside A, B and F, in good overall yields. The spectroscopic data of the final products were compared with the bibliographic data of the natural products and were found in good agreement with some notable differences that were fully explained. Additionally, a conformational analysis of these structures was performed through NOESY experiments and theoretical calculations, providing valuable insights into their 3D structure.
This work contributes to an efficient synthesis of syringoleosides A, B and F, presents a methodological pathway that will be probably useful for the synthesis of structurally related secoiridoid natural products and allows further structural and biological studies of structure-activity relationships.
Main subject category:
Science
Keywords:
natural products, secoiridoids, oleuropein, synthesis, Syringoleoside A, B and F, NOESY, conformational analysis
File:
File access is restricted until 2027-02-28.
ΜΔΕ_ΣΟΥΦΛΑ ΑΛΙΚΗ.pdf
10 MB
File access is restricted until 2027-02-28.
