Κατεύθυνση Απομόνωση, Ανάπτυξη, Παραγωγή και Έλεγχος Βιοδραστικών Φυσικών Προϊόντων
Library of the School of Science

2023-05-18

2023

Papazoglou Georgia

Μαρία Χαλαμπαλάκη, Αναπληρώτρια Καθηγήτρια, Τμήμα Φαρμακευτικής, ΕΚΠΑ,
Σοφία Μητάκου Καθηγήτρια, Τμήμα Φαρμακευτικής, ΕΚΠΑ,
Ελευθέριος Καλπουτζάκης ΕΔΙΠ Τμήμα Φαρμακευτικής, ΕΚΠΑ

Φυτοχημική Μελέτη, Απομόνωση & Ταυτοποίηση Δευτερογενών Μεταβολιτών των ριζών του φυτού Alkanna methanaea Hausskn.- (Boraginaceae)

Greek

Phytochemical investigation, isolation and structure elucidation of bioactive compounds of the roots of Alkanna methanaea Hausskn.- (Boraginaceae)

Alkanna methanaea Hausskn. is an endemic Greek species belonging to the Boraginaceae family. Although the genus Alkanna is mostly known for its lipophilic red pigments alkannins/shikonins and related isohexenylnaphthazarins found in the roots, it also contains a non-negligible amount of hepatotoxic pyrrolizidine alkaloids. Thus, the aim of the present study was the extensive phytochemical investigation of A. methanaea root extracts.
At first, the roots were extracted with two different solvents (cyclohexane-cHex and methanol-MeOH). After the extraction, a qualitative investigation of the extracts was performed using analytical techniques such as Thin Layer Chromatography (TLC), High Pressure Liquid Chromatography with a photodiode array detector (HPLC-DAD), Ultra High Pressure Liquid Chromatography coupled to a High Resolution Mass Spectrometer (UPLC-HRMS/MS) and Gas Chromatography coupled to a Mass Spectrometer (GC-MS). The isolation process started with the initial fractionation of both extracts, for which Liquid Countercurrent Chromatography (FCPC) was used, in particular the elution-extrusion method. The isolation of the secondary metabolites, in pure form, was performed by further treatment of selected fractions with Low Pressure Column Chromatography (CC), Preparative Thin Layer Chromatography (Prep-TLC), Size Exclusion Liquid Chromatography, for which dextran gel (Sephadex) was used as a stationary phase, as well as Semi Preparative High Performance Liquid Chromatography (Semi Preparative-HPLC). For the final structure elucidation of the isolated secondary metabolites, 1 & 2D NMR and Ultra High Pressure Liquid Chromatography coupled to a High Resolution Mass Spectrometer (UPLC-HRMS/MS) were employed.
Conclusively, the phytochemical study of the cyclohexane extract led to the identification of 22 non-polar compounds and the isolation of a 4 known alkannins’ mixture, whereas 3 phenolic compounds, 1 nucleoside, 6 lignans the 3 of which were isolated for the first time in Alkanna genus. Moreover, 5 pyrrolizidine alkaloids among which 2 new natural products and 1 derivative which was isolated for the first time in Boraginaceae family, were isolated and identified from the methanol extract. To our knowledge, this is the first time that Alkanna methanaea Hausskn. is being phytochemically investigated.

Science

Health Sciences

Alkanna methanaea Hausskn., Boraginaceae, Phytochemical investigation, alkannins, pyrrolizidine alkaloids, lignans

No

0

Yes

273

172

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https://pergamos.lib.uoa.gr/uoa/dl/object/3328566