1-1-diphenyl-2-picrylhydrazyl and 2-tert-butylhydroquinone

Tertiary butylhydroquinone (TBHQ) is a water-insoluble antioxidant. In this study, three cyclodextrin inclusion complexes were prepared to improve the water solubility of TBHQ and expand its range of application. Analysis of phase solubility indicated that TBHQ can form 1:1 inclusion complex with hydroxypropyl-beta-cyclodextrin (HP-β-CD) and dimethyl-beta-cyclodextrin (DM-β-CD) and 1:2 inclusion complex with beta-cyclodextrin (β-CD). The possible inclusion configuration between TBHQ and CDs was determined through FT-IR, PXRD, DSC, NMR, and SEM analyses. Results were validated by theoretical study of AutoDock molecular docking. The scavenging effects of the inclusion complexes were not effective on DPPH radical but higher on hydroxyl, superoxide and ABTS+ radicals than that of TBHQ monomer. Moreover, the water solubility of TBHQ increased after complexation with HP-β-CD and DM-β-CD. The stability of TBHQ is related to the type of storage materials used, and the stability can be improved by complexation with CDs.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; Antioxidants; beta-Cyclodextrins; Biphenyl Compounds; Cell Line; Humans; Hydroquinones; Magnetic Resonance Spectroscopy; Microscopy, Electron, Scanning; Molecular Docking Simulation; Picrates; Solubility; Solutions; Spectroscopy, Fourier Transform Infrared; Water; X-Ray Diffraction

A series of novel l-ascorbyl fatty acid esters were synthesized by catalization of Novozym(®) 435 under ultrasonic irradiation and characterized by infrared spectroscopy, electrospray ionization mass spectra, and nuclear magnetic resonance. Their properties especially antioxidant activity and stability were investigated. The results showed that the reducing power, the scavenging activity of hydroxyl radical and 2,2-diphenyl-1-picrylhydrazyl radical were decreased with the increase of the number of carbon atoms in fatty acid. The hydroxyl radical scavenging activity and reducing power of l-ascorbyl saturated fatty acid esters were better than that of tert-butylhydroquinone. The induction period in lipid oxidation of l-ascorbyl saturated fatty acid esters and tert-butylhydroquinone were longer than that of l-ascorbyl unsaturated fatty acid esters and l-ascorbic acid both in soybean oil and lard. Besides, the l-ascorbyl fatty acid esters showed different stabilities in different conditions by comparing with l-ascorbic acid, and the l-ascorbyl saturated fatty acid esters were more stable than l-ascorbyl unsaturated fatty acid esters in ethanol solution.

Topics: Antioxidants; Ascorbic Acid; Biphenyl Compounds; Dietary Fats; Esters; Fatty Acids; Fatty Acids, Unsaturated; Food Preservatives; Humans; Hydroquinones; Lipase; Lipid Peroxidation; Oxidation-Reduction; Picrates; Soybean Oil; Ultrasonic Waves; Ultrasonics

Antioxidant effectiveness of free radical scavengers (FRSs) of alpha-tocopherol, sesamol, butylated hydroxytoluene (BHT), and tert-butylhydroquinone (TBHQ) were evaluated in thermally-oxidized lard using methods of 2,2-diphenyl-1-picrylhydrazyl (DPPH), conjugated dienoic acid (CDA), and p-anisidine value (p-AV). Absorbance of DPPH with lard containing 2.5 micromol/g FRSs were low before oxidation while those with control lard was high due to the hydrogen atom donating ability of FRSs. During oxidation, DPPH absorbance with lard containing FRSs increased differently up to the certain point depending on the types of FRSs. DPPH absorbance of lard without FRSs started to decrease upon oxidation, which indicates that free radical scavenging compounds were generated from oxidized lipids. Results of CDA and p-AV showed that the highest antioxidant capacity was in the order of TBHQ = sesamol, BHT, and alpha-tocopherol. Antioxidant effectiveness of FRS should consider the hydrogen atom donating rates of FRS, the reactivity and stability of FRS at treatment temperature, and characteristics of radicals from FRSs, which may be predicted by the results of DPPH method.

Topics: alpha-Tocopherol; Aniline Compounds; Antioxidants; Benzodioxoles; Biphenyl Compounds; Butylated Hydroxytoluene; Dietary Fats; Food Analysis; Food Preservation; Food Preservatives; Free Radical Scavengers; Hot Temperature; Hydroquinones; Linoleic Acids, Conjugated; Oxidation-Reduction; Phenols; Picrates; Spectrophotometry; Time Factors

The antioxidant and pro-oxidant effects of thymoquinone (TQ), a natural main constituent of the volatile oil of Nigella saliva seeds, and a synthetic structurally-related tert-butylhydroquinone (TBHQ), were examined in vitro. Both TQ and TBHQ efficiently inhibited iron-dependent microsomal lipid peroxidation in a concentration-dependent manner with median inhibitory concentration (IC50) values of 16.8 and 14.9 microM, respectively. TBHQ was stronger than TQ as a scavenger of 2,2'-diphenyl-p-picrylhydrazyl radical (DPPH) (IC50 = 5 microM, 200 times more active than TQ) and as a scavenger of hydroxyl radical (OH*) with an IC50 of 4.6 microM (approximately 10 times more active than TQ). TQ was more active than TBHQ as a superoxide anion scavenger with IC50 of 3.35 microM compared to 18.1 microM for TBHQ. Only TBHQ significantly promoted DNA damage in the bleomycin-Fe(III) system. The results suggest that both TQ and TBHQ have strong antioxidant potentials through scavenging ability of different free radicals. Moreover, the data indicate that TQ is acting mainly as a potent superoxide anion scavenger.

Topics: Animals; Antioxidants; Benzoquinones; Biphenyl Compounds; Bleomycin; DNA Damage; Free Radical Scavengers; Hydroquinones; In Vitro Techniques; Lipid Peroxidation; Male; Microsomes, Liver; Nigella sativa; Oxidation-Reduction; Picrates; Plant Oils; Rats; Rats, Wistar; Superoxides