title: A novel benzimidazole and other constituents with antiproliferative and antioxidant properties from Thymelaea microphylla Coss. et Dur.
abstract: A new compound (microphybenzimidazole, 7) along with the six known compounds matairesinol (1), prestegane B (2), umbelliferone (3), daphnoretin (4), microphynolide A (5) and microphynolide B (6) were isolated from Thymelaea microphylla. The structures of the pure compounds were elucidated by spectroscopic and mass-spectrometric analyses, including 1D-, 2D-NMR, and HPLC-TOF/MS. Compounds 2 and 4, as well as three fractions (F6, F6-C5, and F6-W42) obtained from a 50% (v:v) CH2Cl2:MeOH extract exhibited a selective activity against rat brain glioma cells (C6). Moreover, compound 1 and other fractions obtained from 50% (v:v) CH2Cl2:MeOH and 70% (v:v) MeOH:H2O extracts exhibited dose- and time-dependent effects on human cervical cancer cell (HeLa), as measured by xCELLigence assay. Compound 2 (IC50= 14.0 ± 0.2 μg/mL) and fraction F5 (IC50= 12.4 ± 0.1 μg/mL) showed higher radical scavenging ability than the synthetic agent butylated hydroxytoluene (BHT, IC50= 22.7 ± 0.6 μg/mL).
authors.affiliation: a Laboratory of Natural Products and Organic Synthesis, Department of Chemistry, Faculty of Science , University of Mentouri-Constantine , Constantine , Algeria.|d Laboratory of Plant Research, Department of Chemistry, Faculty of Science , Cankiri Karatekin University , Cankiri , Turkey.
authors.forename: Labib
authors.initials: L
authors.lastname: Noman
authors.affiliation: b Department of Biology, Faculty of Science , Gazi University , Ankara , Turkey.
authors.forename: Feyza
authors.initials: F
authors.lastname: Oke-Altuntas
authors.affiliation: a Laboratory of Natural Products and Organic Synthesis, Department of Chemistry, Faculty of Science , University of Mentouri-Constantine , Constantine , Algeria.|c Laboratory of Biomolecules and Plant Breeding, Life Science and Nature Department, Faculty of Exact Science and Life Science and Nature , University of Larbi Ben Mhidi Oum El Bouaghi , Oum El Bouaghi , Algeria.
authors.forename: Amar
authors.initials: A
authors.lastname: Zellagui
authors.affiliation: d Laboratory of Plant Research, Department of Chemistry, Faculty of Science , Cankiri Karatekin University , Cankiri , Turkey.
authors.forename: Ayse
authors.initials: A
authors.lastname: Sahin Yaglioglu
authors.affiliation: d Laboratory of Plant Research, Department of Chemistry, Faculty of Science , Cankiri Karatekin University , Cankiri , Turkey.
authors.forename: Ibrahim
authors.identifier: http://orcid.org/0000-0001-8946-647X
authors.initials: I
authors.lastname: Demirtas
authors.affiliation: e Department of Chemistry & QOPNA , University of Aveiro , Aveiro , Portugal.
authors.forename: Susana
authors.initials: S
authors.lastname: M Cardoso
authors.affiliation: f Departement de Chimie, Facultés des Sciences exactes , Université de Constantine, Unité de Recherche Valorisation des ressources naturelles Molécules bioactives et Analyses Physico-Chimiques et Biologiques , Constantine , Algéria.
authors.forename: Salah
authors.initials: S
authors.lastname: Akkal
authors.affiliation: a Laboratory of Natural Products and Organic Synthesis, Department of Chemistry, Faculty of Science , University of Mentouri-Constantine , Constantine , Algeria.|c Laboratory of Biomolecules and Plant Breeding, Life Science and Nature Department, Faculty of Exact Science and Life Science and Nature , University of Larbi Ben Mhidi Oum El Bouaghi , Oum El Bouaghi , Algeria.
authors.forename: Noureddine
authors.initials: N
authors.lastname: Gherraf
authors.affiliation: a Laboratory of Natural Products and Organic Synthesis, Department of Chemistry, Faculty of Science , University of Mentouri-Constantine , Constantine , Algeria.
authors.forename: Salah
authors.initials: S
authors.lastname: Rhouati
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D001562:Benzimidazoles / Q000737:chemistry* / Q000494:pharmacology; D002084:Butylated Hydroxytoluene / Q000494:pharmacology; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid; D003374:Coumarins / Q000737:chemistry / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D005663:Furans / Q000737:chemistry / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D017705:Lignans / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D051381:Rats; D064210:Secondary Metabolism; D029645:Thymelaeaceae / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D001562:Benzimidazoles; D003374:Coumarins; D005663:Furans; D017705:Lignans; C000623395:microphybenzimidazole; D002084:Butylated Hydroxytoluene; C035316:daphnoretin; C068935:matairesinol; C053360:prestegane B; D015107:4-Butyrolactone
keywords: C6; HeLa; Thymelaea microphylla; antioxidant activity; antiproliferative activity; microphybenzimidazole