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

Abstract : For 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 mu M. 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 mu M, 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.
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https://hal.inrae.fr/hal-03174723
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Submitted on : Friday, March 19, 2021 - 2:31:24 PM
Last modification on : Saturday, March 20, 2021 - 3:07:30 AM

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Ilyes Saidi, Wiem Baccari, Axel Marchal, Pierre Waffo-Téguo, Abdel Halim Harrath, et al.. Iridoid glycosides from the Tunisian Citharexylum spinosum L.: Isolation, structure elucidation, biological evaluation, molecular docking and SAR analysis. Industrial Crops and Products, Elsevier, 2020, 151, pp.1-10. ⟨10.1016/j.indcrop.2020.112440⟩. ⟨hal-03174723⟩

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