A novel benzimidazole and other constituents with antiproliferative and antioxidant properties from Thymelaea microphylla Coss. et Dur

• Published in: Natural product research 2017-09, Vol.31 (17), p.2032-2041
• Main Authors: Noman, Labib, Oke-Altuntas, Feyza, Zellagui, Amar, Sahin Yaglioglu, Ayse, Demirtas, Ibrahim, M Cardoso, Susana, Akkal, Salah, Gherraf, Noureddine, Rhouati, Salah
• Format: Article
• Language: English
• Subjects: 4-Butyrolactone - analogs & derivatives; 4-Butyrolactone - chemistry; 4-Butyrolactone - pharmacology; Animals; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - pharmacology; antioxidant activity; Antioxidants; Antioxidants - chemistry; Antioxidants - pharmacology; antiproliferative activity; Antiproliferatives; Benzimidazoles; Benzimidazoles - chemistry; Benzimidazoles - pharmacology; Brain; Brain tumors; Butylated hydroxytoluene; Butylated Hydroxytoluene - pharmacology; Cell Line, Tumor; Cervical cancer; Cervix; Chromatography, High Pressure Liquid; Coumarins - chemistry; Coumarins - pharmacology; Dose-Response Relationship, Drug; Furans - chemistry; Furans - pharmacology; Glioma cells; HeLa; HeLa Cells; High-performance liquid chromatography; Humans; Lignans - chemistry; Lignans - pharmacology; Liquid chromatography; Matairesinol; microphybenzimidazole; Molecular Structure; NMR; Nuclear magnetic resonance; Rats; Scavenging; Secondary Metabolism; Spectrometry; Spectroscopic analysis; Thymelaea microphylla; Thymelaeaceae - chemistry; Thymelaeaceae - metabolism; Two dimensional analysis; Umbelliferone
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2016.1274888

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) CH 2 Cl 2 :MeOH extract exhibited a selective activity against rat brain glioma cells (C6). Moreover, compound 1 and other fractions obtained from 50% (v:v) CH 2 Cl 2 :MeOH and 70% (v:v) MeOH:H 2 O extracts exhibited dose- and time-dependent effects on human cervical cancer cell (HeLa), as measured by xCELLigence assay. Compound 2 (IC 50  = 14.0 ± 0.2 μg/mL) and fraction F5 (IC 50  = 12.4 ± 0.1 μg/mL) showed higher radical scavenging ability than the synthetic agent butylated hydroxytoluene (BHT, IC 50  = 22.7 ± 0.6 μg/mL)