HNS-RE2SD Research Laboratories Documents
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Laboratories of the Higher National School of Renewable Energies, Environment and Sustainable Development
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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 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.