Titre :

A Three-Step Process to Isolate Large Quantities of Bioactive Sesquiterpene Lactones from Cichorium intybus L. Roots and Semisynthesis of Chicory STLs Standards

Auteur(s) :

Ruggieri, Francesca [Auteur]
Médicaments et molécules pour les systèmes vivants - U 1177 [M2SV]
HANCE, PHILIPPE [Auteur]
BioEcoAgro - UMR transfrontalière INRAe - UMRT1158
Gioia, Bruna [Auteur]
Médicaments et Molécules pour agir sur les Systèmes Vivants (M2SV) - U1177
Biela, Alexandre [Auteur]
Médicaments et Molécules pour agir sur les Systèmes Vivants (M2SV) - U1177
Roussel, Pascal [Auteur]
Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181
Hilbert, Jean-Louis [Auteur]
BioEcoAgro - UMR transfrontalière INRAe - UMRT1158
willand, nicolas [Auteur]
Médicaments et Molécules pour agir sur les Systèmes Vivants (M2SV) - U1177

Titre de la revue :

Pharmaceuticals

Numéro :

16

Pagination :

771

Éditeur :

MDPI

Date de publication :

2023-05-22

ISSN :

1424-8247

Mot(s)-clé(s) en anglais :

chicory
sesquiterpene lactones
11
13-dihydrolactucin
lactucin
plant extraction
semisynthesis of analytical standards

Discipline(s) HAL :

Chimie/Chimie inorganique

Résumé en anglais : [en]

Sesquiterpene lactones (STLs) are a large group of terpenoids most commonly found in plants of the Asteraceae family, e.g., in chicory plants, displaying a wide range of interesting biological activities. However, further ...
Lire la suite >Sesquiterpene lactones (STLs) are a large group of terpenoids most commonly found in plants of the Asteraceae family, e.g., in chicory plants, displaying a wide range of interesting biological activities. However, further studies on the biological potential of chicory-derived STLs and analogues are challenging as only four of these molecules are commercially available (as analytical standards), and to date, there are no published or patented simple extraction–purification processes capable of large-scale STLs isolation. In this work, we describe a novel three-step large-scale extraction and purification method for the simultaneous purification of 11,13-dihydrolactucin (DHLc) and lactucin (Lc) starting from a chicory genotype rich in these STLs and the corresponding glucosyl and oxalyl conjugated forms. After a small-scale screening on 100 mg of freeze-dried chicory root powder, the best results were achieved with a 17 h water maceration at 30 °C. With these conditions, we managed to increase the content of DHLc and Lc, at the same time favoring the hydrolysis of their conjugated forms. On a larger scale, the extraction of 750 g of freeze-dried chicory root powder, followed by a liquid–liquid extraction step and a reversed-phase chromatography, allowed the recovery of 642.3 ± 76.3 mg of DHLc and 175.3 ± 32.9 mg of Lc. The two pure STLs were subsequently used in the context of semisynthesis to generate analogues for biological evaluation as antibacterial agents. In addition, other described chicory STLs that are not commercially available were also synthesized or extracted to serve as analytical standards for the study. In particular, lactucin-oxalate and 11,13-dihydrolactucin-oxalate were synthesized in two steps starting from Lc and DHLc, respectively. On the other hand, 11β,13-dihydrolactucin-glucoside was obtained after a MeOH/H2O (70/30) extraction, followed by a liquid–liquid extraction step and a reversed-phase chromatography. Together, this work will help facilitate the evaluation of the biological potential of chicory-derived STLs and their semisynthetic analogues.Lire moins >

Langue :

Anglais

Audience :

Internationale

Vulgarisation :

Non

Projet Européen :

Programme for EArly-stage Researchers in Lille

Projet ANR :

ULNE
Multiparametric Strategies against Antibiotic Resistance in Tuberculosis

Établissement(s) :

Université de Lille
CNRS
Centrale Lille
ENSCL
Univ. Artois

Collections :

• Médicaments et Molécules pour agir sur les Systèmes Vivants (M2SV) - U1177
• Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181

Équipe(s) de recherche :

Matériaux inorganiques, structures, systèmes et propriétés (MISSP)

Date de dépôt :

2023-06-20T12:17:04Z
2023-06-29T16:22:41Z