Brown seaweeds produce useful bioactive substances with high cosmetic and pharmacological values due to the presence of antioxidant derivatives, mainly phlorotannins (PHT), which are of particular interest. A central composite rotatable design (CCRD) with three variables (extraction time, dry material-to-solvent ratio and ethanol concentration) and two responses was performed to optimize the microwave-assisted extraction (MAE) of phlorotannins from Cystoseira sedoides using response surface methodology (RSM). Results showed that the independent variables significantly affected both phlorotannin content and the scavenging capacity. The optimum operating conditions were extraction time, 101.74 sec; dry material-to-solvent ratio, 1:10 g/mL; and ethanol extraction, 50%. Under these conditions, the predicted values of PHT content and radical scavenging activity-IC50 were close to the observed values and were 383.887 µg PGE/g Dm and 18.353 µg/mL, respectively. Characterization of the phlorotannin-rich fraction was conducted by high-performance liquid chromatography and Fourier transform infrared spectroscopy. The evaluation of the anticancer activity against MCF-7 breast cancer cell line showed a potent activity to trigger apoptotic death in more than a half of the MCF-7 cells, with an estimated IC50 value of 78 μg/mL. In addition, this fraction induced a notable growth regression effect on 3D spheroids model in a concentration-dependent manner, with a growth rate of about 1.17, at 200 µg/mL. Abbreviations: CCRD: Central composite rotatable design; Dm: Dry material; DMBA: 2,4-dimethoxy benzaldehyde; DMSO: Dimethyl sulfoxide; DPPH: 1,1-diphenyl-2-picrylhydrazyl; EDTA: Ethylene diamine tetraacetic acid; FBS: Fetal bovine serum; FT-IR: Fourier transform infrared; HPLC: High-performance liquid chromatography; IC50: Half-maximal inhibitory concentration; MAE: Microwave-assisted extraction; Min: minutes; PBS: Phosphate buffered saline; PGE: Phloroglucinol equivalent; PHT: Phlorotannins; PHT-SED: phlorotannins derived from Cystoseira sedoides; PI: Propidium iodide; RSA: Radical scavenging activity; RSM: Response surface methodology; Sec: seconds
A green and mild synthetic route to N-alkylbenzamides involves eco-friendly one pot synthesis of 2-alkyl-3-aryloxaziridines from N-alkylamines and benzaldehydes followed by iron(III) sulfate catalyzed rearrangement to the corresponding amides in water as the solvent and in the presence of sodium dodecyl sulfate as the surfactant. This green approach affords N-alkylbenzamides in high overall yields under simple and minimum manipulation.
Honey has a history of medical use and is known as bio-alternative therapy. This research assessed the phytochemical and biological activity of the medical grade manuka honey (MH). Gas chromatography–mass spectrometry (GC–MS) was chosen to investigate bioactive compounds of the MH. The DPPH and ABTS free radical scavenging and beta-carotene antioxidant activities as well as the antibacterial and antibiofilm effects against S. aureus, B. subtilis, E. coli and P. aeruginosa were all determined. Furthermore, to gauge anticancer properties of MH, a MTT assay was opted towards three cell lines, including HCT-116 (colon), A549 (lung) and MCF-7 (breast) cancer cells. The GC–MS analysis of the tested MH revealed the identification of various chemical constituents belonging to the fatty acids, phenols, and esters. The MH was found to have higher reducing power activity (DPPH IC50: 7.36; ABTS IC50: 4.49 mg/mL) than the beta-carotene bleaching power (IC50: 37.51 mg/mL). Similarly, the MH was noted to be more active against the planktonic and biofilm of Gram-positive bacteria. Furthermore, a dose-dependent anticancer potential was observed, although a significant anticancer potential was pointed out against the MCF-7 and A549 cell conforming to the IC50 values of 9.05 and 9.37 mg/mL, respectively. This study’s results have highlighted the MH’s chemical composition with significant bioactivities.
N -Alkyloxaziridines 1 , N -sulfonyloxaziridines 2 and N -phosphinoyloxaziridines 3 were prepared in good to high yields by oxidation of the corresponding imines with the trichloroacetonitrile–hydrogen peroxide system under mild reaction conditions. A concerted mechanism is proposed for the oxidation of N -alkylimines and a two-step mechanism is suggested for the oxidation of electron-deficient N -sulfonylimines and N -phosphinoylimines. .
Benzonitrile-hydrogen peroxide oxidation of prochiral and chiral imines 1a–h leads to racemic (E)-oxaziridines (R,R/S,S) and nonracemic (E)-oxaziridines (R,R,R/S,S,R) 2a–h, respectively.