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Human & Experimental Toxicology Mar 2016Garlic contains diallylsulfide (DAS) and other structurally related compounds that are widely believed to be active agents in preventing cancer. This study shows the...
Garlic contains diallylsulfide (DAS) and other structurally related compounds that are widely believed to be active agents in preventing cancer. This study shows the effect of DAS (a phenolic antioxidant used in foods, cosmetics, and pharmaceutical products) on ferric nitrilotriacetate (Fe-NTA)-induced hepatotoxicity in rats. Male albino rats of Wistar strain weighing 125-150 g were given a single dose of Fe-NTA (9 mg kg(-1) body weight, intraperitoneally) after 1 week of treatment with 100 and 200 mg kg(-1) DAS in corn oil respectively administered through the gavage. Fe-NTA administration led to 2.5-fold increase in the values of both alanine transaminase and aspartate aminotransferase, respectively, and 3.2-fold increase in the activity of lactate dehydrogenase, microsomal lipid peroxidation to approximately 2.0-fold compared to saline-treated control. The activities of glutathione (GSH) and other antioxidant enzymes decreased to a range of 2.2-2.5-fold. These changes were reversed significantly (p < 0.001) in animals receiving a pretreatment of DAS. DAS protected against hepatic lipid peroxidation, hydrogen peroxide generation, preserved GSH levels, and GSH metabolizing enzymes to 60-80% as compared to Fe-NTA alone-treated group. Present data suggest that DAS can ameliorate the toxic effects of Fe-NTA and suppress oxidant-induced tissue injury and hepatotoxicity in rats.
Topics: Alanine Transaminase; Allyl Compounds; Animals; Antioxidants; Aspartate Aminotransferases; Chemical and Drug Induced Liver Injury; Ferric Compounds; Glutathione; Glutathione Reductase; Glutathione Transferase; Hydrogen Peroxide; L-Lactate Dehydrogenase; Liver; Male; Nitrilotriacetic Acid; Oxidants; Rats, Wistar; Sulfides
PubMed: 25904316
DOI: 10.1177/0960327115583362 -
Food & Function Feb 2022Tissue factor (TF) is a critical initiator of extrinsic coagulation that sometimes causes thromboembolism. Diallyl trisulphide (DATS) is a secondary metabolite of...
Tissue factor (TF) is a critical initiator of extrinsic coagulation that sometimes causes thromboembolism. Diallyl trisulphide (DATS) is a secondary metabolite of allicin generated in crushed garlic, with various pharmacological effects. This study aimed to clarify the effect of DATS on the extrinsic coagulation elicited by TF and arteriosclerosis. TF activity was measured using a clotting assay in TF-expressing HL60 cells. DATS inhibited TF activity in a dose-dependent manner. TF expression in TNF-α-stimulated human umbilical vein endothelial cells was examined using real-time PCR and western blotting. DATS inhibited TF mRNA and protein expression induced by TNF-α inhibition of JNK signalling. The effect of DATS on arteriosclerosis was also examined in apolipoprotein E-deficient mice. DATS administration in these mice tended to decrease atherosclerotic lesion size. These results strongly suggest that DATS prevents thromboembolism triggered by atherosclerosis the inhibition of plaque formation and TF function.
Topics: Allyl Compounds; Animals; Antioxidants; Apoptosis; Disease Models, Animal; Garlic; Male; Mice; Sulfides; Thromboplastin
PubMed: 35022635
DOI: 10.1039/d1fo02206g -
Pest Management Science Aug 20191,3-Dichloropropene (1,3-D) is a soil fumigant used for the control of nematodes in high-value fruit, nut and vegetable crops globally. Extensive water monitoring... (Review)
Review
BACKGROUND
1,3-Dichloropropene (1,3-D) is a soil fumigant used for the control of nematodes in high-value fruit, nut and vegetable crops globally. Extensive water monitoring efforts have been undertaken over the past four decades by public and private institutions, given the widespread agricultural use of 1,3-D, and environmental fate and metabolism data suggesting the potential for 1,3-D to leach into groundwater. The aim of this study is to review the results of groundwater monitoring studies for 1,3-D conducted in North America and the European Union (EU) since 1980.
RESULTS
Analysis of > 50 000 water samples by state and federal agencies in the USA resulted in 151 detections of 1,3-D. An additional 4000 samples analyzed in groundwater studies specifically targeting high 1,3-D use areas in Europe and the USA resulted in 74 detections of 1,3-D or its primary metabolites. The combined detection rate of 1,3-D and its primary metabolites in high-use areas of the EU and North America was 0.7%.
CONCLUSIONS
The availability of extensive groundwater monitoring information developed through decades of study supports the conclusion that soil fumigation with 1,3-D poses an inconsequential risk for drinking water exposure. The lack of significant detections of 1,3-D from targeted monitoring studies is due to the high volatility of 1,3-D, the rapid degradation of 1,3-D in most agricultural soils, the rapid degradation of 1,3-D and its metabolites in aerobic aquatic systems, and the rapid hydrolysis of 1,3-D in water. © 2019 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
Topics: Allyl Compounds; Environmental Monitoring; European Union; Groundwater; Hydrocarbons, Chlorinated; Insecticides; United States; Water Pollutants, Chemical
PubMed: 30843340
DOI: 10.1002/ps.5398 -
Natural Product Research Dec 2017The present study investigates the antimicrobial activity of alliin degradation products by enzymatic and alkali-heat treatment. The results suggested that the...
The present study investigates the antimicrobial activity of alliin degradation products by enzymatic and alkali-heat treatment. The results suggested that the suppressive effect of enzymatic degradation products (AE) on Escherichia coli was much higher than alkali-heat treatment products (AA). Both AE and AA seriously destroyed the integrity of E. coli cell membrane, decreased the utilisation of intracellular proteins and the absorption of extracellular phosphorus. Furthermore, GC-MS analysis preliminarily confirmed that alliin degradation products contained a variety of sulphur compounds, such as allyl disulphide and dithiene. The antibacterial activities exhibited by AE demonstrate their potential for use as E. coli inhibitor in food.
Topics: Allyl Compounds; Anti-Bacterial Agents; Cysteine; Disulfides; Escherichia coli; Gas Chromatography-Mass Spectrometry; Hydrolysis
PubMed: 28278629
DOI: 10.1080/14786419.2017.1297440 -
Chemistry (Weinheim An Der Bergstrasse,... Apr 2015This Minireview discusses catalytic asymmetric conjugate addition and allylic alkylation reactions where the nucleophiles were generated in situ by hydrometallation or... (Review)
Review
This Minireview discusses catalytic asymmetric conjugate addition and allylic alkylation reactions where the nucleophiles were generated in situ by hydrometallation or carbometallation. This exciting recent trend in asymmetric catalysis promises to expand the range of transformations available for the rapid and selective assembly of complex, functional molecules for both academic and industrial research. This Minireview aims to serve as a reference for studies reported to date and discusses the current state-of-the-art, scope and limitations of these processes.
Topics: Alkylation; Allyl Compounds; Catalysis; Chemistry Techniques, Synthetic; Metals; Stereoisomerism
PubMed: 25603764
DOI: 10.1002/chem.201405855 -
Angewandte Chemie (International Ed. in... Nov 2022We describe cooperative bimetallic catalysis that enables regio-/stereodivergent asymmetric α-allylations of aldimine esters. By employing Et B as the key activator,...
Cooperative Catalyst-Enabled Regio- and Stereodivergent Synthesis of α-Quaternary α-Amino Acids via Asymmetric Allylic Alkylation of Aldimine Esters with Racemic Allylic Alcohols.
We describe cooperative bimetallic catalysis that enables regio-/stereodivergent asymmetric α-allylations of aldimine esters. By employing Et B as the key activator, racemic allylic alcohols can be directly ionized to form Pd or Ir-π-allyl species in the presence of achiral Pd or chiral Ir complexes, respectively. The less or more substituted allylic termini of the metal-π-allyl species are amenable to nucleophilic attack by the chiral Cu-azomethine ylide, the formation of which is simultaneously facilitated by Et B, affording α-quaternary α-amino acids with high regioselectivity and excellent stereoselectivity. The use of readily available allylic alcohols as electrophilic precursors represents an improvement from an environmental and atom/step economy perspective. Computational mechanistic studies reveal the crucial role of the Et B additive and the origins of stereo- and regioselectivities by analyzing steric effects, dispersion interactions, and frontier orbital population.
Topics: Esters; Stereoisomerism; Allyl Compounds; Molecular Structure; Alkylation; Catalysis; Amino Acids
PubMed: 36161447
DOI: 10.1002/anie.202212948 -
Frontiers in Cellular and Infection... 2018Fresh aqueous extracts (AGEs) and several thioallyl compounds (TACs) from garlic have an important antimicrobial activity that likely involves their interaction with...
Fresh aqueous extracts (AGEs) and several thioallyl compounds (TACs) from garlic have an important antimicrobial activity that likely involves their interaction with exposed thiol groups at single aminoacids or target proteins. Since these groups are present in trophozoites, in this work we evaluated the anti-giardial activity of AGE and several garlic's TACs. susceptibility assays showed that AGE affected trophozoite viability initially by a mechanism impairing cell integrity and oxidoreductase activities while diesterase activities were abrogated at higher AGE concentrations. The giardicidal activities of seven TACs were related to the molecular descriptor HOMO (Highest Occupied Molecular Orbital) energy and with their capacity to modify the -SH groups exposed in giardial proteins. Interestingly, the activity of several cysteine proteases in trophozoite lysates was inhibited by representative TACs as well as the cytopathic effect of the virulence factor giardipain-1. Of these, allicin showed the highest anti-giardial activity, the lower HOMO value, the highest thiol-modifying activity and the greatest inhibition of cysteine proteases. Allicin had a cytolytic mechanism in trophozoites with subsequent impairment of diesterase and oxidoreductase activities in a similar way to AGE. In addition, by electron microscopy a marked destruction of plasma membrane and endomembranes was observed in allicin-treated trophozoites while cytoskeletal elements were not affected. In further flow cytometry analyses pro-apoptotic effects of allicin concomitant to partial cell cycle arrest at G2 phase with the absence of oxidative stress were observed. In experimental infections of gerbils, the intragastric administration of AGE or allicin decreased parasite numbers and eliminated trophozoites in experimentally infected animals, respectively. These data suggest a potential use of TACs from garlic against and in the treatment of giardiasis along with their additional benefits in the host's health.
Topics: Allyl Compounds; Animals; Antiprotozoal Agents; Cell Survival; Disease Models, Animal; Enzyme Inhibitors; Garlic; Gerbillinae; Giardia lamblia; Giardiasis; Parasite Load; Parasitic Sensitivity Tests; Plant Extracts; Sulfides; Treatment Outcome; Trophozoites
PubMed: 30374433
DOI: 10.3389/fcimb.2018.00353 -
Journal of the American Chemical Society Jan 2019A Rh-catalyzed enantioselective hydroamination of allylamines using a chiral BIPHEP-type ligand is reported. Enantioenriched 1,2-diamines are formed in good yields and...
A Rh-catalyzed enantioselective hydroamination of allylamines using a chiral BIPHEP-type ligand is reported. Enantioenriched 1,2-diamines are formed in good yields and with excellent enantioselectivities. A diverse array of nucleophiles and amine directing groups are demonstrated, including deprotectable motifs. Finally, the methodology was demonstrated toward the rapid synthesis of 2-methyl-moclobemide.
Topics: Allyl Compounds; Amination; Amines; Catalysis; Coordination Complexes; Ligands; Moclobemide; Rhodium; Stereoisomerism
PubMed: 30614700
DOI: 10.1021/jacs.8b09811 -
Toxicology Mechanisms and Methods Nov 2019Leukopenia is the early clinical manifestation of benzene poisoning. The aim of our research was to evaluate the preventive effects of three kinds of garlic preparations...
Leukopenia is the early clinical manifestation of benzene poisoning. The aim of our research was to evaluate the preventive effects of three kinds of garlic preparations on benzene induced leukopenia. The mouse model of Leukopenia was established with benzene orally. At the same time, mice were administrated with garlic homogenate (GH), garlic oil (GO) or diallyl trisulfide (DATS) as preventional measures. The counts of white blood cells (WBC), the organ indexes, pathological examinations, blood biochemical parameters, weight gains, and food intakes were evaluated to observe the protective effect and potential adverse events. The results demonstrated that the counts of WBC increased by 144.04%, 140.07%, and 148.34%, respectively, after intervention by GH (400 mg/kg), GO (60 mg/kg) and DATS (30 mg/kg), compared with that in the model group. The spleen and thymus indexes in the benzene model group were 44.99% and 54.04% lower than those in the blank control group, the number of spleen nodules reduced and the thymus atrophy, which were restored by three garlic preparations at different degree. The results suggested that the three preparations all could prevent the leukopenia and protect the organ injuries induced by benzene. However, the spleen index and weight gains revealed that GH and GO brought more adverse events than DATS.
Topics: Allyl Compounds; Animals; Benzene; Disease Models, Animal; Garlic; Leukocyte Count; Leukopenia; Male; Mice, Inbred Strains; Plant Preparations; Spleen; Sulfides; Thymus Gland
PubMed: 31364917
DOI: 10.1080/15376516.2019.1650148 -
The Journal of Organic Chemistry Apr 2019Alkoxyallylsiletanes are capable of highly chemo- and diastereoselective carbonyl allylsilylations. Reactive substrates include salicylaldehydes and glyoxylic acids....
Alkoxyallylsiletanes are capable of highly chemo- and diastereoselective carbonyl allylsilylations. Reactive substrates include salicylaldehydes and glyoxylic acids. Chemoselectivity in these reactions is thought to arise from a mechanism involving first exchange of the alkyoxy group on silicon with a substrate hydroxyl followed by activation of a nearby carbonyl by the Lewis acidic siletane and intramolecular allylation. In this way, substrates containing multiple reactive carbonyl groups (e.g., dialdehyde or triketone) can be selectively monoallylated, even overcoming inherent electrophilicity bias.
Topics: Aldehydes; Allyl Compounds; Glyoxylates; Silanes; Stereoisomerism
PubMed: 30811929
DOI: 10.1021/acs.joc.8b03028