Search Results (11)

In this paper, we aimed to evaluate whether simple, low molecular mass benzoquinone derivatives, featuring different substituents in para- and meta-position relative to the tert-butyl group, possess biological activities against major targets associated with Alzheimer’s disease. The 1,4-benzoquinone derivatives studied herein inhibited both cholinesterases in the micromolar concentration range, generally showing a preference for butyrylcholinesterase over acetylcholinesterase; formed complexes with biometal ions Fe²⁺, Cu²⁺ and Zn²⁺; and displayed a certain BACE1 inhibition. Moreover, the tested compounds displayed certain antioxidant activity via either electron transfer or hydrogen atom transfer mechanisms. The antioxidant capacity of the unsubstituted tert-butyl-1,4-benzoquinone (compound 1) was three times lower than that of the standard antioxidant BHT, while 2,6-disubstituted derivatives (compounds 15 and 7) exhibited peroxyl radical scavenging activity comparable to that of Trolox. Taken together with in silico-predicted low toxicity, good intestinal absorption and favorable oral bioavailability, the presented 1,4-benzoquinone derivatives are promising scaffolds for the design of more complex molecules with enhanced cholinesterase and BACE1 inhibitory activity. Furthermore, they could serve as functional substituents in other structural scaffolds to combine and enhance their biological activities. Full article

N-acetyl para-aminophenol was suggested as a safer alternative to other drugs on the market for pain and fever in 1948. It was given the generic name “acetaminophen” in 1951 and the trade name “Tylenol” when it was put on the market in the USA in 1955 as a prescription drug to treat pediatric fever. It also received the generic name “paracetamol” in the UK where it was initially marketed in 1956 under the name “Panadol.” Toxicity from overdose of acetaminophen was reported in 1966. Research at the US National Institutes of Health uncovered the mechanisms of toxicity and proposed a treatment in a foundational series of papers in 1973 and 1974. A nomogram was developed in 1973 and published in 1975 to guide estimation of patient risk of hepatic toxicity. Rapid development followed utilizing acetylcysteine given both orally and intravenously. Various protocols and methods of administration have been employed over time with the primary use today of acetylcysteine intravenously as the therapeutic method. The nomogram has been revised over time to the current version, published in 2023, which allows stratification of patients to a high-risk group over 300 mg/L at 4 h and standard risk above 150 mg/L at 4 h, except in the UK where the standard risk is defined very conservatively with a line above 100 mg/L at 4 h. Adjunct therapy with fomepizole in patients with massive ingestions, delay until arrival in a health care facility or renal injury has been proposed. The mortality rate with treatment has been substantially reduced and recovery from hepatic injury is achieved in almost all patients. Full article

The photoreduction of plastoquinone, a para-benzoquinone, by chlorophyll initiates photosynthesis in chloroplasts. The direct photoreduction of biologically relevant quinones by dietary chlorophyll metabolites has been reported and may influence health outcomes. We examined red light-mediated photoreduction of ortho- and para-naphthoquinones including vitamin K₃ using the photosensitizers methylene blue and pheophorbide A, a chlorophyll metabolite. Naphthoquinone reduction was monitored by UV/Visible spectroscopy and required a photosensitizer, red light and a tertiary amine electron donor. Combinations of methylene blue and ethylenediaminetetraacetic acid or pheophorbide A and triethanolamine in 20% dimethylformamide were employed for all photoreduction experiments. Hydrogen peroxide was generated during the photochemical reactions by singlet oxygen-dependent oxidation of the reduced naphthoquinones. Hydrogen peroxide was quantified with horseradish peroxidase following irradiation; the reduced naphthoquinones acted as peroxidase co-substrates. Histidine, a singlet oxygen scavenger, enhanced the rate of photoreduction by limiting the re-oxidation process. Catalase slowed the rate of photoreduction by regenerating molecular oxygen from hydrogen peroxide so that it could be photoexcited to singlet oxygen. The rates and extent of naphthoquinone photoreduction were dependent on molecular oxygen exposure in different reaction formats including in a cuvette and a plate well. Reduction of the tetrazolium salt MTT to the formazan via electron transfer from the photoreduced quinones was also used to quantitate the extent of photoreduction. Full article

Photosynthesis is initiated when the sun’s light induces electron transfer from chlorophyll to plastoquinone, a para-quinone. While photosynthesis occurs in the intact chloroplasts of living plants, similar photochemical reactions between dietary chlorophyll metabolites and quinones are likely and may affect health outcomes. Herein, we continue our studies of the direct photoreduction of para-quinones and ortho-quinones that were generated by the photo-oxidation of catechols. Chlorophyll metabolites, including pheophorbide A, chlorin e6, and pyropheophorbide A, as well as methylene blue were employed as photosensitizers. We detected hydrogen peroxide using horseradish peroxidase following the photo-oxidation of the catechol dopamine, even in the presence of EDTA, a tertiary amine electron donor. Under ambient oxygen, hydrogen peroxide was also detected after the photoreduction of several para-quinones, including 2,3-dimethoxy-5-methyl-p-benzoquinone (CoQ₀), methoxy-benzoquinone, and methyl-benzoquinone. The combinations of methylene blue and EDTA or pheophorbide A and triethanolamine as the electron donor in 20% dimethylformamide were optimized for photoreduction of the para-quinones. Chlorin e6 and pyropheophorbide A were less effective for the photoreduction of CoQ₀ but were equivalent to pheophorbide A for generating hydrogen peroxide in photo-oxidation reactions with photosensitizers, oxygen, and triethanolamine. We employed dinitrophenylhydrazine to generate intensely colored adducts of methoxy-benzoquinone, methyl-benzoquinone, and 1,4-benzoquinone. Full article

Heterogeneous Fenton technology was employed for the advanced treatment of Maotai-flavored Baijiu wastewater. Novel catalysts were prepared by loading different active ingredients (Mn, Fe, and Cu) on γ-Al₂O₃ using an impregnation method. The effects of active ingredient, reaction time, initial pH, H₂O₂ dosage, catalyst dosage, and other factors on the reaction were examined. The properties of the new catalysts were analyzed using BET analysis, XPS, and SEM. Moreover, the mechanisms of Fenton-like oxidation and its reaction kinetics were explored through experiments and analyses including GC–MS and intermediate active species scavenging by tertiary butyl alcohol (TBA) and/or para-benzoquinone. The results revealed that the most effective removal of organic matter was achieved with a Mn-Fe/Al (2:1 wt%) catalyst dosage of 30 g/100 g water, pH of 5.0, H₂O₂ dosage of 0.3 g/L, and reaction time of 60 min; the effluent COD value was 12 ± 1 mg/L, and the degradation rate was 65.7 ± 3%, approximately 14% higher than that of the conventional Fenton catalyst under similar conditions; moreover, the catalytic efficacy remained high after seven cycles. Kinetic analysis indicated that the heterogeneous Fenton oxidation reaction followed a third-order kinetics model, with R² = 0.9923 and K = 0.0006 min⁻¹. Full article

All-organic Li-ion batteries appear to be a sustainable and safer alternative to the currently-used Li-ion batteries but their application is still limited due to the lack of organic compounds with high redox potentials toward Li⁺/Li⁰. Herein, we report a computational design of nickel complexes and coordination polymers that have redox potentials spanning the full voltage range: from the highest, 4.7 V, to the lowest, 0.4 V. The complexes and polymers are modeled by binding low- and high-oxidized Ni ions (i.e., Ni(II) and Ni(IV)) to redox-active para-benzoquinone molecules substituted with carboxyl- and cyano-groups. It is found that both the nickel ions and the quinone-derived ligands are redox-active upon lithiation. The type of Ni coordination also has a bearing on the redox potentials. By combining the complex of Ni(IV) with 2-carboxylato-5-cyano-1,4-benzoquinones as a cathode and Ni(II)-2,5-dicarboxylato-3,6-dicyano-1,4-benzoquinone coordination polymer as an anode, all-organic Li-ion batteries could be assembled, operating at an average voltage exceeding 3.0 V and delivering a capacity of more than 300 mAh/g. Full article

Coenzyme Q (ubiquinone or CoQ) is a conserved polyprenylated lipid essential for mitochondrial respiration. CoQ is composed of a redox-active benzoquinone ring and a long polyisoprenyl tail that serves as a membrane anchor. A classic pathway leading to CoQ biosynthesis employs 4-hydroxybenzoic acid (4HB). Recent studies with stable isotopes in E. coli, yeast, and plant and animal cells have identified CoQ intermediates and new metabolic pathways that produce 4HB. Stable isotope labeling has identified para-aminobenzoic acid as an alternate ring precursor of yeast CoQ biosynthesis, as well as other natural products, such as kaempferol, that provide ring precursors for CoQ biosynthesis in plants and mammals. In this review, we highlight how stable isotopes can be used to delineate the biosynthetic pathways leading to CoQ. Full article

Encouraged by the promising antitumoral, antiangiogenic, and antilymphangiogenic properties of toluquinol, a set of analogues of this natural product of marine origin was synthesized to explore and evaluate the effects of structural modifications on their cytotoxic activity. We decided to investigate the effects of the substitution of the methyl group by other groups, the introduction of a second substituent, the relative position of the substituents, and the oxidation state. A set of analogues of 2-substituted, 2,3-disubstituted, and 2,6-disubstituted derived from hydroquinone were synthesized. The results revealed that the cytotoxic activity of this family of compounds could rely on the hydroquinone/benzoquinone part of the molecule, whereas the substituents might modulate the interaction of the molecule with their targets, changing either its activity or its selectivity. The methyl group is relevant for the cytotoxicity of toluquinol, since its replacement by other groups resulted in a significant loss of activity, and in general the introduction of a second substituent, preferentially in the para position with respect to the methyl group, was well tolerated. These findings provide guidance for the design of new toluquinol analogues with potentially better pharmacological properties. Full article

Four new para-benzoquinone containing abietane-type diterpenoids (1–4) along with thirteen known diterpenoids (5–17) were isolated from the roots of Plectranthus punctatus. The structures of the compounds were established by detailed spectroscopic analyses and comparison with literature data. The compounds were tested for their antibacterial and cytotoxic activity and showed significant inhibitory activity against all bacterial strains used, with compounds 6, 8, 10, and 11 showing an inhibition zone for Staphylococcus warneri even greater than the reference drug, gentamycin. Full article