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

Isochamaejasmin and other flavonoids isolated from an endemic Algerian desert species

“…Recently, we have reported the new benzimidazole and six known compounds with their antiproliferative and antioxidant activities from T. microphylla (11). We herein report the isolation and structural elucidation of three flavonoids from the chloromethanolic extract of T. microphylla.…”

“…It has been used in folk medicine for the treatment of wounds, erysipelas, skin cancer, pimples, and abscess (8). Several studies have shown that this species had remarkable antibacterial, antioxidant (9, 10), antiinflammatory (6), and antiproliferative (11) activities.…”

“…Phytochemical studies on this species were indicated the presence of bicoumarin and their glycoside derivatives, linear-type furanocoumarin glucosides and simple coumarin glucosides (12). Daphnoretine (bicoumarin), umbelliferone (simple coumarin) and prestegane B (lignans) have been isolated from the aerial parts of Thymelaea microphylla (11). The report related to the chemical analysis of Thymelaea microphylla essential oil in the literature showed the major components were D-menthone (41.86 %), 2-undecanone (23.74 %), pulegone (11.94 %) and perillal (9.34 %) (13).…”

Prospect of natural products in glioma: A novel avenue in glioma management

“…Prestegane B is a natural compound isolated from Thymelaea microphylla , which exhibits a selective antiproliferative effect in C6 cells. It also has free radical scavenging property (Noman et al, ). Selenocysteine, a natural selenoamino acid, arrests S‐phase of the cell cycle by DNA damage via ROS and superoxide generation in U251 and U87 cells.…”

Daphnoretin Arrests the Cell Cycle and Induces Apoptosis in Human Breast Cancer Cells

“…Recently, phytochemicals have grabbed attention in the study of breast cancer therapy because of the strong antitumor activity and few adverse effects on patients. , Icariin, a flavanol glycoside, effectively causes apoptosis and suppresses migration through the SIRT6/NF-κB signal molecules in breast cancer cells . Daphnoretin, one of the main active ingredients of Daphne giraldii Nitsche, displays several pharmacological effects, e.g., antitumor effect, antioxidation effect, and anti-inflammation. − One study reported that daphnoretin induced apoptosis and inhibited cell invasion and migration via the PI3K/AKT signal molecules in colon cancer HCT116 cells . Daphnoretin also displayed an obvious concentration-dependent suppression of HeLa cell proliferation.…”