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Isocostic Acid, a Promising Bioactive Agent from the Essential Oil of Inula viscosa (L.) Insights from Drug Likeness Properties, Molecular Docking and SAR Analysis

Abstract : The chemical composition of the essential oil (LEO) and its volatile fractions (V 1 –V 10 ) collected during the hydrodistillation process every 15 min from the fresh leaves of I. viscosa (L.), growing in Tunisia, were analyzed by GC-FID and GC/MS. Eighty-two compounds, representing 90.9–99.4 % of the total samples, were identified. The crude essential oil (LEO) and its fractions (V 1 –V 10 ) were characterized by the presence of a high amount of oxygenated sesquiterpenes (82.7–95.8 %). Isocostic acid (1) was found to be the most abundant component (37.4–83.9 %) and was isolated from the same essential oil over silica gel column chromatography and identified by spectroscopic methods ( 1 H, 13 C, DEPT 135 NMR and EI-MS) and by comparison with literature data. Furthermore, the fresh leaves essential oil (LEO), its volatile fractions (V 1 –V 10 ) as well as compound 1 were screened for their antibacterial, antityrosinase, anticholinesterase and anti-5-lipoxygenase activities. It was found that the isolated compound 1 exhibited an interesting antibacterial activity against Staphylococcus aureus ATCC 25923 (MIC=32 μg/mL) and Enterococcus faecalis ATCC 29212 (MIC=32 μg/mL) and the highest antityrosinase activity (IC 50 =13.82±0.87 μg/mL). Compound 1 was also found to be able to strongly inhibit 5-lipoxygenase with an IC 50 value of 59.21±0.85 μg/mL. The bioactivity and drug likeness scores of compound 1 were calculated using Molinspiration software and interpreted, and the structure-activity relationship (SAR) was discussed with the help of molecular docking analysis. © 2019 Wiley-VHCA AG, Zurich, Switzerland
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02413279
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Submitted on : Monday, December 16, 2019 - 10:43:19 AM
Last modification on : Tuesday, October 20, 2020 - 6:48:06 PM

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I. Aissa, V.D. Nimbarte, A. Zardi-Bergaoui, M. Znati, G. Flamini, et al.. Isocostic Acid, a Promising Bioactive Agent from the Essential Oil of Inula viscosa (L.) Insights from Drug Likeness Properties, Molecular Docking and SAR Analysis. Chemistry and Biodiversity, Wiley, 2019, 16 (4), pp.e1800648. ⟨10.1002/cbdv.201800648⟩. ⟨hal-02413279⟩

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