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52. Phenolic Glycosides from the Stem Bark of Caryocar villosumand C. glabrum

Author

Alabdul Magid, Abdulmagid, Voutquenne-Nazabadioko, Laurence, Harakat, Dominique, Moretti, Christian, and Lavaud, Catherine

Abstract

Mushroom tyrosinase inhibitory activity of methanol extracts and polar fractions of the stem bark of Caryocar villosumand C. glabrumhas been assessed. Seven new phenolic glycosides ( 1– 7) were isolated from the most active fractions, along with 15 known compounds ( 8– 22). The structures of these compounds were established on the basis of spectroscopic methods including 1D and 2D NMR analysis, HRESIMS, and comparison with literature experimental data for known compounds.

Published
2008
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53. Chemical constituents of Genista numidica Spach aerial parts and their antimicrobial, antioxidant and antityrosinase activities

Author

Naima Boutaghane, Abdulmagid Alabdul Magid, Anaïs Cafolla, Zahia Kabouche, Hanène Djeghim, Laurence Voutquenne-Nazabadioko, Amin Abedini, Sophie Gangloff, Université Mentouri Constantine [Algérie] (UMC), Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Biomatériaux et inflammation en site osseux - EA 4691 (BIOS), Université de Reims Champagne-Ardenne (URCA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV), Université frères Mentouri Constantine I (UMC), Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS), and Alabdul Magid, Abdulmagid

Subjects
Antioxidant, medicine.medical_treatment, Genista numidica, antioxidant activity, Plant Science, 01 natural sciences, Biochemistry, Analytical Chemistry, Triterpenoid saponins, antibacterial activity, [CHIM] Chemical Sciences, medicine, [CHIM]Chemical Sciences, Triterpenoid saponin, chemistry.chemical_classification, Traditional medicine, 010405 organic chemistry, Chemistry, Organic Chemistry, Fabaceae, Antimicrobial, 0104 chemical sciences, antityrosinase activity, 010404 medicinal & biomolecular chemistry, Chemical constituents, flavonoids, Antibacterial activity
Abstract

A previously undescribed triterpenoid saponin, 3-O-[α-l-rhamnopyranosyl-(1→2)-{β-d-glucopyranosyl-(1→6)-}β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl]-sophoradiol (1), in addition to twenty-nine known constituents (2–30) were isolated from the aerial parts of Genista numidica Spach. Structures elucidation was performed by comprehensive 1D- and 2D-NMR analyses and HRESIMS. The extracts, fractions and isolated compounds were evaluated for their antibacterial, antioxidant and tyrosinase inhibitory activities. The experimental findings indicated that genistin (16), isosalipurpol (27), and koaburaside (29) have moderate to low antibacterial activity against E. faecalis, S. aureus, S. epidermidis and P. aeruginosa bacteria with MICs ranging from 31.2 to 125 μg/mL. Compounds 19 and 27 exhibited a good antiradical activity potential (IC50 11.8 and 11.1 μg/mL, respectively). Only compounds 23, 27 and 28 exhibited low inhibitory effect against mushroom tyrosinase (IC50 from 90.2 to 225.6 μg/mL).

Published
2018
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54. Triterpene glycosides from the aerial parts of Gouania longipetala

Author

Laurence Voutquenne-Nazabadioko, Jérôme Josse, Hamid Morjani, Sophie Gangloff, Antoine Ahibo Coffy, Philomène Akoua Yao-Kouassi, Abdulmagid Alabdul Magid, Diane Patricia Apie Gossan, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Félix Houphouët-Boigny (UFHB), Biomatériaux et inflammation en site osseux - EA 4691 (BIOS), Université de Reims Champagne-Ardenne (URCA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV), Matrice extracellulaire et dynamique cellulaire - UMR 7369 (MEDyC), Université de Reims Champagne-Ardenne (URCA)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS), Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS), and Alabdul Magid, Abdulmagid

Subjects
Staphylococcus aureus, HL60, Stereochemistry, HL-60 Cells, Microbial Sensitivity Tests, Plant Science, Horticulture, 01 natural sciences, Biochemistry, Enterococcus faecalis, Terpene, chemistry.chemical_compound, Gouania, Triterpene, [CHIM] Chemical Sciences, Escherichia coli, Humans, [CHIM]Chemical Sciences, Glycosides, Nuclear Magnetic Resonance, Biomolecular, Molecular Biology, chemistry.chemical_classification, Molecular Structure, biology, Cytotoxic activity, 010405 organic chemistry, Gouania longipetala, Rhamnaceae, Glycoside, General Medicine, Plant Components, Aerial, Saponins, Triterpenoids, biology.organism_classification, Antineoplastic Agents, Phytogenic, Triterpenes, Anti-Bacterial Agents, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, chemistry, Antibacterial activity, Drug Screening Assays, Antitumor, K562 Cells
Abstract

International audience; Six previously undescribed triterpenoid saponins, gouaniaside I-VI, were isolated from the aerial parts of Gouania longipetala Hemsl. (Rhamnaceae), in addition to four known triterpenes. The structure elucidation of these compounds was based on analyses of spectroscopic data including 1D- and 2D-NMR and HR-ESI-MS techniques. The inhibitory activity of isolated compounds against promyelocytic leukemia HL60 and human erythromyeloblastoid leukemia K562 cell lines was evaluated and jujuboside I exhibited moderate cytotoxicity, with IC50 values of 13.5 and 21.0 μM, respectively. Among the isolated triterpenes, alphitolic acid exhibited moderate antibacterial activity against Staphylococcus aureus, Enterococcus faecalis and Escherichia coli (MICs 32, 64 and 128 μg/mL, respectively).

Published
2017
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55. Chemical composition, antioxidant and antibacterial activities of Tamarix balansae J. Gay aerial parts

Author

Zahia Kabouche, Mounira Benteldjoune, Djemaa Berrehal, Ahmed Kabouche, Abdulmagid Alabdul Magid, Abbes Benmerache, Laurence Voutquenne-Nazabadioko, Amin Abedini, Sophie Gangloff, Université Mentouri Constantine [Algérie] (UMC), Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Biomatériaux et inflammation en site osseux - EA 4691 (BIOS), Université de Reims Champagne-Ardenne (URCA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV), Université frères Mentouri Constantine I (UMC), Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS), and Alabdul Magid, Abdulmagid

Subjects
DPPH, antioxidant activity, Ether, Microbial Sensitivity Tests, Plant Science, 01 natural sciences, Biochemistry, Antioxidants, Enterococcus faecalis, Analytical Chemistry, chemistry.chemical_compound, Phenols, antibacterial activity, Staphylococcus epidermidis, [CHIM] Chemical Sciences, [CHIM]Chemical Sciences, Organic chemistry, Food science, Afzelin, Bacteria, Molecular Structure, biology, Plant Extracts, Tamaricaceae, 010405 organic chemistry, Organic Chemistry, Free Radical Scavengers, Plant Components, Aerial, biology.organism_classification, Anti-Bacterial Agents, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, Tamarix balansae, chemistry, flavonoids, Kaempferol, Antibacterial activity, Quercetin
Abstract

A previously undescribed phenolic sulphate ester, potassium 34-dihydroxy-3-methoxybenzoic acid methyl ester-5-sulphate (1), along with nine known flavonoids, kaempferol-3-O-potassium sulphate-4′,7-dimethyl ether (2), kaempferol-4′,7-dimethyl ether (3), rhamnocitrin-3-O-potassium sulphate (4), rhamnocitrin (5), kaempferol (6), quercetin (7), afzelin (8), quercetin-3-O-α-l-rhamnopyranoside (9) and luteolin-3′-O-potassium sulphate (10) were isolated from the aerial parts of Tamarix balansae. Structures elucidation was performed by comprehensive 1D and 2D NMR analyses, mass spectrometry and by comparison with literature data. The antibacterial assay against Enterococcus faecalis, Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli and Pseudomonas aeruginosa bacteria showed a good activity for 2, 3, 7 and 9, with MICs ranging from 62.5 to 250 μg/mL. The abilities of these compounds to scavenge the DPPH were evaluated. Compounds 1, 7, 9 and 10 exhibited a good antiradical activity potential with IC50 values ranging from 3.0 to 115.5 μg/mL, compared with ascorbic acid (IC50 7.4 μg/mL) which was used as positive control.

Published
2017
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56. Pyrroloquinolone A, a new alkaloid and other phytochemicals from A tractylis cancellata L. with antioxidant and anticholinesterase activities.

Author

Badaoui MI, Alabdul Magid A, Benkhaled M, Bensouici C, Harakat D, Voutquenne-Nazabadioko L, and Haba H

Subjects
Antioxidants isolation & purification, Cholinesterase Inhibitors isolation & purification, Molecular Structure, Phytochemicals isolation & purification, Phytochemicals pharmacology, Plant Extracts pharmacology, Quinolones isolation & purification, Alkaloids isolation & purification, Alkaloids pharmacology, Antioxidants pharmacology, Atractylis chemistry, Cholinesterase Inhibitors pharmacology, Quinolones pharmacology
Abstract

A new alkaloid pyrroloquinolone A ( 1 ), along with fifteen known compounds 2-16 were isolated from the petroleum ether, EtOAc and n -BuOH extracts of the whole plant Atractylis cancellata L. Their structures were elucidated on the basis of extensive spectroscopic analysis including 1D- and 2D-NMR and HR-ESI-MS techniques. This is the first report of alkaloids in the genus Atractylis . Some of the isolated compounds and extracts were evaluated for their antioxidant potential (scavenging activity of DPPH and ABTS radicals, and reducing Fe +3 and Cu +2 power assays) and acetylcholinesterase and butyrylcholinesterase inhibitory activities. Compounds 8 and 11 showed good antioxidant capacity compared to ascorbic acid, BHA, and BHT used as standards, whereas compounds 1 and 2 exhibited good anticholinesterase activities compared to galantamine used as standard.

Published
2021
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57. A new 2-alkylhydroquinone glucoside from Phagnalon saxatile (L.) Cass.

Author

Cherchar H, Lehbili M, Berrehal D, Morjani H, Alabdul Magid A, Voutquenne-Nazabadioko L, Kabouche A, and Kabouche Z

Subjects
A549 Cells, Drug Screening Assays, Antitumor, Humans, Inhibitory Concentration 50, MCF-7 Cells, Magnetic Resonance Spectroscopy, Molecular Structure, Plant Components, Aerial chemistry, Plant Extracts chemistry, Spectrometry, Mass, Electrospray Ionization, Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic pharmacology, Asteraceae chemistry, Glucosides chemistry
Abstract

A new 2-alkylhydroquinone glucoside, 1-O-β-d-glucopyranosyl-1,4-dihydroxy-2-((E) 2-oxo-3-butenyl)benzene (1), in addition to nine known compounds were isolated from the aerial parts of Phagnalon saxatile (L.) Cass. (Asteraceae). Their structures were identified based on spectroscopic methods including 1D and 2D NMR, mass spectrometry (HR-ESI-MS), UV spectral analyses and by comparison with literature data. The cytotoxic activity of three isolated compounds (1-3) was evaluated against fibrosarcoma (HT1080), human lung cancer (A549) and breast cancer (MCF7) cell lines.

Published
2018
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58. Triterpenoid saponins from the fruits of Caryocar villosum.

Author

Alabdul Magid A, Voutquenne L, Harakat D, Pouny I, Caron C, Moretti C, and Lavaud C

Subjects
Animals, Anti-Bacterial Agents chemistry, Anti-Bacterial Agents pharmacology, Artemia drug effects, Enterococcus faecalis drug effects, Escherichia coli drug effects, Fruit chemistry, Guyana, Molecular Structure, Mycobacterium smegmatis drug effects, Nuclear Magnetic Resonance, Biomolecular, Pseudomonas aeruginosa drug effects, Saponins chemistry, Saponins pharmacology, Staphylococcus aureus drug effects, Triterpenes chemistry, Triterpenes pharmacology, Anti-Bacterial Agents isolation & purification, Plants, Medicinal chemistry, Saponins isolation & purification, Triterpenes isolation & purification
Abstract

Fourteen new triterpenoid saponins (1-14) were isolated from the methanol extract of the fruits of Caryocar villosum along with 10 known saponins. Their structures were established on the basis of extensive NMR (1H, 13C, COSY, TOCSY, ROESY, HSQC, and HMBC) and ESIMS studies. The toxicity of the methanolic extracts of the peel and the pulp of fruits and the crude saponin fraction of the peel was assessed using the Artemia salina test. The antimicrobial activities of caryocarosides IV-21 (14), II-1 (16), III-1 (17), and IV-9 (20) and of saponin 23 were also studied in vitro on Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Mycobacterium smegmatis, and Enterococcus faecalis bacteria.

Published
2006
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