LEREESI research documents
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Laboratory of Renewable Energy, Energy Efficiency and Smart Systems
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Item Flavonoid glycosides and triterpenoids from Atractylis flava(ELSEVIER, 2012-10-24) Chabani, Sonia; Haba, Hamada; Lavaud, Catherine; Benkhaled, Mohammed; Harakat, DominiqueTwo new flavonoid glycosides, together with twelve known compounds including seven flavonoids and five triterpenoids were isolated from the whole plant Atractylis flava Desf. The structures of new compounds have been elucidated as 6-hydroxykaempferol 6-methyl ether 7-O-β-glucopyranuronoside (1) and isorhamnetin 3-O-[(6″′-O-E-feruloyl)-β-d-glucopyranosyl-(1 → 2)]-β-d-galactopyranoside (2) named Atraflavoside A and B successively, on the basis of physical and spectroscopic analysis, including 1D and 2D NMR (1H, 13C, COSY, TOCSY, HSQC, HMBC and NOESY) and mass spectrometry (HRESIMS) whereas those of the known compounds (3–14) were established by spectral comparison with those published in the literature.Item Three new oleanane-type triterpene saponins from Atractylis flava(ELSEVIER, 2015-12-11) Chabani, Sonia; Lavaud, Catherine; Benkhaled, Mohammed; Harakat, Dominique; Long, Christophe; Haba, HamadaThree new bidesmosidic saponins (1–3), along with thirteen known metabolites consisting of two flavonoids and eleven triterpenoids were identified in dichloromethane and n-butanol extracts of the whole plant Atractylis flava Desf. The saponins were characterized as 3-O-[β-d-glucuronopyranosyl]-28-O-[β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyl]-16α-hydroxygypsogenic acid (1), 3-O-[β-d-glucuronopyranosyl]-28-O-[β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl]-16α-hydroxygypsogenic acid (2), and 3-O-[β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranosyl]-28-O-[((3-O-acetyl)-β-d-xylopyranosyl)-(1 → 4)-((2-O-acetyl)-α-l-rhamnopyranosyl)-(1 → 2)-β-d-xylopyranosyl]-quillaic acid (3). Structures of all isolated compounds were elucidated by spectroscopic analysis, including 1D and 2D NMR (1H, 13C, COSY, HSQC, TOCSY, HSQC-TOCSY, HMBC, ROESY and NOESY), high-resolution electrospray ionization mass spectrometry (HRESIMS), acid hydrolysis, measurement of optical rotation and comparison with literature data.Item Chemical composition of medicinal plant Atractylis serratuloides(ELSEVIER, 2016-03-05) Chabani, Sonia; Haba, Hamada; Long, Christophe; Benkhaled, MohammedPhytochemical investigation of the roots of Atractylis serratuloides Sieber ex Cass. (Asteraceae) led to the isolation of nine compounds 1–9 including eight triterpenoids and one phenolic compound. Their structures were established on the basis of physical and spectroscopic analysis, including 1D and 2D NMR (1H, 13C, COSY, HSQC, and HMBC), mass spectrometry ESI, and by comparison with those published in the literature. Triterpenoids are typical compounds of Atractylis genus and could be useful as characteristic markers in chemotaxonomic research. In addition, isolated triterpenoids have previously showed many biological activities and might explain the use of A. serratuloides in traditional medicine.Item Phytochemicals, Antihemolytic, Anti-inflammatory, Antioxidant, and Antibacterial Activities from Thymus Algeriensis(TAYLOR & FRANCIS LTD, 2021-03-12) Mokhtari, Mouna; Chabani, Sonia; Mouffouk, Soumia; Aberkane, Mohamed-Cherif; Dibi, Ammar; Benkhaled, Mohammed; Haba, HamadaThe chemical composition and anti-inflammatory, antihemolytic, antioxidant, and antibacterial activities of solvent extracts of Thymus algeriensis in petroleum ether, chloroform, and n-butanol were evaluated. Ten compounds including four flavonoids, four phenolics, and two triterpenoids were isolated and identified by chromatography and spectroscopy. The n-butanol extract had the greatest antioxidant activity and inhibited hemolysis with a value of IC50 at 322.85 ± 0.87 µg mL−1. The chloroform extract exhibited the highest anti-inflammatory effect with 45.27% inhibition. The extracts demonstrated antibacterial activity against the tested strains.Item A new flavonoid glycoside from the aerial parts of Diplotaxis erucoides (L.) DC. growing in Algeria(TAYLOR & FRANCIS LTD, 2022-05-24) Mokhtari, Mouna; Chabani, Sonia; Alabdul Magid, Alabdulmagid; Benkhaled, Mohammed; Voutquenne-Nazabadioko, Laurence; Haba, HamadaThe phytochemical study of the 70% ethanol extract of the aerial parts of Diplotaxis erucoides afforded one new flavonoid glycoside, namely kaempferol-3-O-[α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside]-7-O-α-L-rhamnopyranoside (1), named diploerucoside A and seven known compounds including one flavonoid (2), one phenolic glycoside (3), one monoterpene (4), one triterpene (5), one sitosterol (6) and two monoglycerolipids (7, 8). Their structures were established by extensive spectroscopic analysis including 1 D- and 2 D-NMR (1H, 13C, 1H-1H COSY, HSQC and HMBC), mass spectrometry (HR-ESI-MS) and by comparison with the data reported in the literature.Item Chemical constituents of Centaurea dissecta Ten. and sesquiterpenes chemotaxonomic significance(PERGAMON-ELSEVIER SCIENCE LTD, 2024-03-06) Badaoui, Mohamed Ibrahim; Chabani, Sonia; Alabdul Magid, Abdulmagid; Voutquenne-Nazabadioko, Laurence; Sayagh, Charlotte; Harakat, Dominique; Haba, HamadaThe phytochemical investigation of Centaurea dissecta Ten. led to the isolation of thirty-two compounds of diverse chemical classes including two sesquiterpene lactones (1, 2), two sesquiterpenes (3, 4), twelve flavonoids (5–16), one lignan (17), twelve phenols (18–29), one triterpene (30) and two phytosterols (31, 32) from the EtOAc and n-BuOH soluble fractions of the 70% aqueous ethanol extract. Furthermore, the phenolic and flavonoid contents were measured for the petroleum ether, EtOAc and n-BuOH soluble fractions. The chemical structures of these compounds were determined by using a combination of NMR spectroscopic and mass spectrometry (ESI-MS) analyses, as well as by comparison with literature values. Only apigenin (15) was isolated previously from Centaurea affinis, and all other compounds were isolated for the first time from this species. Noticeably, ethyl ferulate (20), ethyl caffeate (21), synapyl aldehyde (22), coniferyl aldehyde (23), 2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone (24), and C-veratroylglycol (25), have not been reported from the genus Centaurea. All compounds have been previously isolated in various plants belonging to the Asteraceae family. Meanwhile, the chemotaxonomic significance of the isolated compounds was summarized.Item A new 7,9′-monoepoxylignan glucoside and other phytochemicals from Centaurea granatensis and their chemotaxonomic significance(PERGAMON-ELSEVIER SCIENCE LTD, 2024-07-30) Belaid, Meriem; Mouffouk, Soumia; Chabani, Sonia; Mouffouk, Chaima; Benkhaled, Mohammed; Haba, HamadaThe chemical study of Centaurea granatensis Boiss. ex DC. allowed the isolation and structural elucidation of eighteen secondary metabolites (1-18) from ethyl acetate (EtOAc) and n-butanol (n-BuOH) extracts. These compounds are divided into one new epoxylignan glucoside (1) and seventeen known phytochemicals including seven flavonoids (2-8), four triterpenes (9-12), and six phytosterols (13-18). Structures of the isolates were identified using various spectroscopic methods, namely 1D NMR (1H and 13C), 2D NMR (HSQC, 1H-1H COSY, HMBC, and NOESY), and mass spectrometry (HR-ESIMS), as well as by comparison with literature data. The obtained results showed the abundance of triterpenoids and flavonoids particularly flavones in C. granatensis. Apigenin (3) could be used as a chemotaxonomic marker of this genus due to its presence in approximately forty plant species. Furthermore, tiliroside (2) and stigmasteryl-3-O-β-D-glucoside-6′-palmitate (18) were first detected in Centaurea genus, but had previously been found in species of the Asteraceae family. Additionally, the chemotaxonomic significance of all isolated molecules was fully discussed.Item Chemical constituents from the Algerian ash Fraxinus dimorpha Coss. & Dur. and their chemotaxonomic significance(PERGAMON-ELSEVIER SCIENCE LTD, 2025-03-21) Bouhentala, Sabrine; Chabani, Sonia; Benkhaled, Mohammed; Haba, HamadaThe investigation of the chemical composition of n-hexane and ethyl acetate extracts from the aerial parts of Fraxinus dimorpha resulted in the isolation of a new compound (1), identified as a fatty acid ester, along with fifteen previously reported secondary metabolites (2–16). These included one fatty acid (2), four triterpenoids (3–6), two phytosterols (7 and 8), three coumarins (9–11), one phenylpropanoid glucoside (12), three secoiridoids (13–15), and one free sugar (16). Among them, undecanoic acid (2), oleanolic acid acetate (4), lupeol (5) and lupenone (6) were identified for the first time within the Fraxinus genus. The structures of isolated compounds (1–16) were elucidated through extensive spectroscopic analyses such as 1D- and 2D-NMR and HR-ESI-MS as well as by comparing experimental data with those reported in the literature. Additionally, the chemotaxonomic significance of the isolated bioactive compounds was discussed.