Alsheikh, W (2025) Assessment of chemopreventive potential of selected medicinal plants from Syria. Doctoral thesis, Liverpool John Moores University.

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Abstract

The study includes a systematic bioassay-guided phytochemical and chemopreventive investigation on three non-dietary wild plants chosen from the Syrian flora. The selection of plants was based on the information in the literature about ethnomedicinal use and their phytochemical content diversity of phytochemical classes that possess antioxidant properties. The aerial parts of Daucus carota subsp. maximus Ball., Foeniculum vulgare L. and Ruta chalepensis L. were dried, ground and extracted using Soxhlet apparatus successively, with n-hexane, dichloromethane (DCM) and methanol (MeOH). The bioassay-guided investigation led to further fractionation to produce four methanolic fractions and one washed-DCM extract using a solid-phase extraction procedure. The non-toxic concentration preserved more than 90% of the human mammary MCF-7 derived reporter AREc32 cell line viability was determined using the MTT assay of all crude extracts and corresponding fractions. The selected non-toxic concentrations were then assessed for Nrf2 induction potential using an AREc32 cell-based luciferase gene reporter assay. The methanolic fractions 2 and 3 from D. carota ssp. maximus, fractions 1, 2 and washed DCM extract from F. vulgare and fraction 3 of R. chalepensis showed the highest induction in luciferase assay with 4.3, 7.3, 7.8, 13.6, 5.9 and 9.1 fold-induction, respectively. A total of 25 compounds from various phytochemical classes (phenolic, flavonoids, furanocoumarins, furanoquinoline alkaloids and acetophenone derivatives) were isolated using chromatographic techniques. Structure elucidation was carried out by employing 1D and 2D nuclear magnetic resonance (NMR) and mass spectrometric techniques. Isolated compounds included 7 compounds from D. carota ssp maximus methanolic fractions 2 and 3, 4 compounds from F. vulgare methanolic fractions 1 and 2 (2 compounds are novel) as well as 3 compounds from the cleaned-up DCM extract (1 novel compound), and 11 compounds from fraction 3 from R. chalepensis. The isolated compounds’ non-toxic concentrations defined by the MTT assay were investigated for their Nrf2 induction potential by performing the luciferase assay. Out of 25 isolated compounds, 19 compounds were considered as potential chemopreventive compounds with greater than 2-fold induction. Eugenin (122) from D. carota ssp maximus methanolic fraction 3, the new compound quercetin-3-O-glucuronide methyl ester (126) from F. vulgare methanolic fractions 2 and moskachan D (133) from R. chalepensis fraction 3 recorded the highest activities with 8.1, 9.3 and 7.5-fold induction, respectively. This study introduced a collective phytochemical and chemoprevention investigation of three non-edible wild plants from the Syrian flora, providing 19 natural compounds as potent chemopreventive agents.

Item Type:	Thesis (Doctoral)
Uncontrolled Keywords:	Cancer chemoprevention; MTT assay; Luciferase assay; HPLC; NMR; Syrian flora
Subjects:	R Medicine > RM Therapeutics. Pharmacology R Medicine > RS Pharmacy and materia medica R Medicine > RV Botanic, Thomsonian, and eclectic medicine
Divisions:	Pharmacy and Biomolecular Sciences
SWORD Depositor:	A Symplectic
Date Deposited:	04 Feb 2025 10:55
Last Modified:	04 Feb 2025 10:55
DOI or ID number:	10.24377/LJMU.t.00025432
Supervisors:	Sarker, S, Ritchie, K and Nahar, L
URI:	https://researchonline.ljmu.ac.uk/id/eprint/25432

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