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Iridoid glycosides from the Tunisian Citharexylum spinosum L.: Isolation, structure elucidation, biological evaluation, molecular docking and SAR analysis

dc.rights.licenseopenen_US
dc.contributor.authorSAIDI, Ilyes
dc.contributor.authorBACCARI, Wiem
hal.structure.identifierUnité de Recherche Oenologie [Villenave d'Ornon] [OENO]
dc.contributor.authorMARCHAL, Axel
hal.structure.identifierUnité de Recherche Oenologie [Villenave d'Ornon] [OENO]
dc.contributor.authorWAFFO TEGUO, Pierre
dc.contributor.authorHARRATH, Abdel Halim
dc.contributor.authorMANSOUR, Lamjed
dc.contributor.authorBEN JANNET, Hichem
dc.date.accessioned2021-04-13T13:49:04Z
dc.date.available2021-04-13T13:49:04Z
dc.date.issued2020-05-04
dc.identifier.issn0926-6690en_US
dc.identifier.urioai:crossref.org:10.1016/j.indcrop.2020.112440
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/26934
dc.description.abstractEnFor several years, chemicals with plant sources are of significant interest mainly for its amazing therapeutic properties and particularly at the structural level. For this reason, a phytochemical investigation and a biological evaluation were performed on the Tunisian Citharexylum spinosum L. tree. The n-butanol extract of flowers from this plant was fractionated by silica gel column chromatography and its fractions have been purified using preparative HPLC, which led to the isolation of a new iridoid glycoside named spinomannoside, as well as seven other known identified as 5-deoxypulchelloside I, pulchelloside I, lamiide, durantoside I, lamiidoside, and caudatosides B and E. The structures of the isolates were established by spectroscopic means including 1D and 2D NMR experiments, and spectrometric ESI-HRMS analysis. Furthermore, the isolated compounds were evaluated in vitro for their anti-tyrosinase, anticholinesterase, and cytotoxic activities. Caudatoside E displayed the highest anti-tyrosinase effect, with a percent of inhibition value of 69.3 ± 2.8 %. Also, the highest anticholinesterase effect was given by caudatoside E with an IC50 value of 22.38 ± 1.82 μM. Lamiidoside and caudatoside E were found to be the most cytotoxic compounds against the human cervical cancer cell line (HeLa) with IC50 values of 17.28 ± 1.40 and 19.02 ± 0.90 μM, respectively. The study of the structure-activity relationship (SAR) has been sufficiently discussed. Caudatoside E, the most active compound, was docked with the protein crystal structures of the PDBs: 2Y9X, 4B0P, and 4I5I.
dc.language.isoENen_US
dc.sourcecrossref
dc.subject.enbioactivities
dc.subject.encitharexylum spinosum L.
dc.subject.eniridoid glycosides
dc.subject.enmolecular docking
dc.subject.enSAR analysis
dc.subject.enspinomannoside
dc.title.enIridoid glycosides from the Tunisian Citharexylum spinosum L.: Isolation, structure elucidation, biological evaluation, molecular docking and SAR analysis
dc.typeArticle de revueen_US
dc.identifier.doi10.1016/j.indcrop.2020.112440en_US
dc.subject.halSciences du Vivant [q-bio]/Biologie végétaleen_US
bordeaux.journalIndustrial Crops and Productsen_US
bordeaux.volume151en_US
bordeaux.hal.laboratoriesOenologie - EA 4577en_US
bordeaux.institutionUniversité de Bordeauxen_US
bordeaux.institutionBordeaux INPen_US
bordeaux.institutionINRAEen_US
bordeaux.peerReviewedouien_US
bordeaux.inpressnonen_US
bordeaux.import.sourcedissemin
hal.exportfalse
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