Title :

Discovery of Anti-Coronavirus Cinnamoyl Triterpenoids Isolated from Hippophae rhamnoides during a Screening of Halophytes from the North Sea and Channel Coasts in Northern France

Author(s) :

Al Ibrahim, Malak [Auteur]
Centre Hospitalier Régional Universitaire [CHU Lille] [CHRU Lille]
BioEcoAgro - Equipe 5 - Specialized Metabolites of Plant Origin
BioEcoAgro - UMR transfrontalière INRAe - UMRT1158
Centre d’Infection et d’Immunité de Lille - INSERM U 1019 - UMR 9017 - UMR 8204 [CIIL]
Akissi, Zachee Louis Evariste [Auteur]
Université de Liège
BioEcoAgro - Equipe 5 - Specialized Metabolites of Plant Origin
Desmarets, Lowiese [Auteur]
Centre Hospitalier Régional Universitaire [CHU Lille] [CHRU Lille]
Centre d’Infection et d’Immunité de Lille - INSERM U 1019 - UMR 9017 - UMR 8204 [CIIL]
Lefèvre, Gabriel [Auteur]
Université de Liège
BioEcoAgro - Equipe 5 - Specialized Metabolites of Plant Origin
BioEcoAgro - UMR transfrontalière INRAe - UMRT1158
Samaillie, Jennifer [Auteur]
Université de Liège
BioEcoAgro - UMR transfrontalière INRAe - UMRT1158
Raczkiewicz, Imelda [Auteur]
Centre Hospitalier Régional Universitaire [CHU Lille] [CHRU Lille]
Centre d’Infection et d’Immunité de Lille - INSERM U 1019 - UMR 9017 - UMR 8204 [CIIL]
Sahpaz, Sevser [Auteur]
Université de Liège
BioEcoAgro - UMR transfrontalière INRAe - UMRT1158
Dubuisson, Jean [Auteur]
Centre Hospitalier Régional Universitaire [CHU Lille] [CHRU Lille]
Centre d’Infection et d’Immunité de Lille - INSERM U 1019 - UMR 9017 - UMR 8204 [CIIL]
Belouzard, Sandrine [Auteur]
Centre Hospitalier Régional Universitaire [CHU Lille] [CHRU Lille]
Centre d’Infection et d’Immunité de Lille - INSERM U 1019 - UMR 9017 - UMR 8204 [CIIL]
Rivière, Céline [Auteur]
Université de Liège
BioEcoAgro - Equipe 5 - Specialized Metabolites of Plant Origin
BioEcoAgro - UMR transfrontalière INRAe - UMRT1158
Seron, Karin [Auteur]
Centre Hospitalier Régional Universitaire [CHU Lille] [CHRU Lille]
Centre d’Infection et d’Immunité de Lille - INSERM U 1019 - UMR 9017 - UMR 8204 [CIIL]

Journal title :

International Journal of Molecular Sciences

Pages :

16617

Publisher :

MDPI

Publication date :

2023

ISSN :

1661-6596

English keyword(s) :

SARS-CoV-2
HCoV-229E
antiviral agents
halophytes
Hippophae rhamnoides
triterpenoids

HAL domain(s) :

Chimie/Chimie thérapeutique
Sciences du Vivant [q-bio]/Biologie végétale/Botanique
Sciences du Vivant [q-bio]/Microbiologie et Parasitologie/Virologie

English abstract : [en]

The limited availability of antiviral therapy for severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has spurred the search for novel antiviral drugs. Here, we investigated the potential antiviral properties of ...
Show more >The limited availability of antiviral therapy for severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has spurred the search for novel antiviral drugs. Here, we investigated the potential antiviral properties of plants adapted to high-salt environments collected in the north of France. Twenty-five crude methanolic extracts obtained from twenty-two plant species were evaluated for their cytotoxicity and antiviral effectiveness against coronaviruses HCoV-229E and SARS-CoV-2. Then, a bioguided fractionation approach was employed. The most active crude methanolic extracts were partitioned into three different sub-extracts. Notably, the dichloromethane sub-extract of the whole plant Hippophae rhamnoides L. demonstrated the highest antiviral activity against both viruses. Its chemical composition was evaluated by ultra-high performance liquid chromatography (UHPLC) coupled with mass spectrometry (MS) and then it was fractionated by centrifugal partition chromatography (CPC). Six cinnamoyl triterpenoid compounds were isolated from the three most active fractions by preparative high-performance liquid chromatography (HPLC) and identified by high resolution MS (HR-MS) and mono- and bi-dimensional nuclear magnetic resonance (NMR). Specifically, these compounds were identified as 2-O-trans-p-coumaroyl-maslinic acid, 3β-hydroxy-2α-trans-p-coumaryloxy-urs-12-en-28-oic acid, 3β-hydroxy-2α-cis-p-coumaryloxy-urs-12-en-28-oic acid, 3-O-trans-caffeoyl oleanolic acid, a mixture of 3-O-trans-caffeoyl oleanolic acid/3-O-cis-caffeoyl oleanolic acid (70/30), and 3-O-trans-p-coumaroyl oleanolic acid. Infection tests demonstrated a dose-dependent inhibition of these triterpenes against HCoV-229E and SARS-CoV-2. Notably, cinnamoyl oleanolic acids displayed activity against both SARS-CoV-2 and HCoV-229E. Our findings suggest that Hippophae rhamnoides could represent a source of potential antiviral agents against coronaviruses.Show less >

Language :

Anglais

Popular science :

Non

Collections :

• Centre d'Infection et d'Immunité de Lille (CIIL) - U1019 - UMR 9017

Source :

Harvested from HAL