- Analysis of responses of allicin, a compound from garlic, in the pulmonary vascular bed of the cat and in the rat
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Allicin, diallyl disulfide-oxide, an active ingredient released from garlic is a systemic vasodilator that acts by an unknown mechanism. In the present experiments, pulmonary vascular responses to allicin (0.1-1.0 mg) were studied in the intact-chest anesthetized cat and in the isolated lung of the rat under constant flow conditions. When baseline tone in the pulmonary vascular bed of the cat was raised with U46619 (11α,9α-epoxymethano-9α,11β-dideoxyprostaglandin F2α), intralobar injections of allicin produced dose-related decreases in pulmonary arterial pressure without changing left atrial pressure indicating that allicin had significant vasodilator activity in the pulmonary vascular bed when tone was increased experimentally. Allicin also decreased systemic arterial pressure in a dose-related manner. In terms of relative vasodilator activity in the cat, allicin was 100-fold less potent than sodium nitroprusside and many orders of magnitude less potent than isoproterenol. In the cat, vasodilator responses to allicin were unchanged by methylene blue or Nω-nitro-L-arginine methyl ester. Allicin also significantly diminished the pulmonary pressor response to ventilatory hypoxia in the isolated perfused rat lung. These data show that allicin has significant vasodilator activity in the pulmonary vascular bed of the cat and the rat. The present data suggest that pulmonary vasodilator responses to allicin are independent of the synthesis of endothelial-derived relaxing factor or the activation of soluble guanylate cyclase.
- Kaye, Alan D.,Nossaman, Bobby D.,Ibrahim, Ikhlass N.,Feng, Chang J.,McNamara, Dennis B.,et al.
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- An optimized facile procedure to synthesize and purify allicin
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Allicin is a reactive sulfur species (RSS) and defence substance from garlic (Allium sativum L.). The compound is a broad-spectrum antibiotic that is also effective against multiple drug resistant (MDR) strains. A detailed protocol for allicin synthesis based on diallyl-disulfide (DADS) oxidation by H2O2 using acetic acid as a catalyst was published in 2001 by Lawson and Wang. Here we report on improvements to this basic method, clarify the mechanism of the reaction and show that it is zero-order with respect to DADS and first-order with respect to the concentration of H2O2. The progress of allicin synthesis and the reaction mechanism were analyzsd by high-performance liquid chromatography (HPLC) and the identity and purity of the products was verified with LC-MS and 1H-NMR. We were able to obtain allicin of high purity (>98%) and >91% yield, with standard equipment available in any reasonable biological laboratory. This protocol will enable researchers to prepare and work with easily and cheaply prepared allicin of high quality.
- Albrecht, Frank,Leontiev, Roman,Jacob, Claus,Slusarenko, Alan J.
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- Therapeutic effect and mechanism study of L-cysteine derivative 5P39 on LPS-induced acute lung injury in mice
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Organosulfur compounds, such as L-cysteine, allicin and other sulfur-containing organic compounds in Allium species, have been proposed to possess many important physiological and pharmacological functions. A novel L-cysteine derivative, t-Butyl S-allylthio-L-cysteinate (5P39), was designed and synthesized by combining L-cysteine derivative and allicin pharmacophore through a disulfide bond. This study aimed to explore the effects and mechanisms of 5P39 on lipopolysaccharide (LPS)-induced acute lung injury (ALI) in mice. At the experimental concentration (5, 10 and 20 μM), 5P39 suppressed the excessive secretion of nitric oxide (NO) and interleukin-6 (IL-6) in mice peritoneal macrophages stimulated by LPS. A mouse model of ALI was established by tracheal instillation of LPS for 2 h before 5P39 (30 and 60 mg/kg) administration. The results showed that 5P39 treatment down-regulated the wet/dry weight ratio (W/D ratio) of lungs and reduced the protein concentration, the number of total cells as well as the myeloperoxidase (MPO) activity in bronchoalveolar lavage fluid (BALF). 5P39 administration improved the histopathological changes of lungs in ALI mice with the decreased levels of pro-inflammatory cytokines in BALF. The inhibitory effects of 5P39 on the toll-like receptor 4 (TLR4) expression and macrophages accumulation in lung tissues were observed by immunohistochemistry. Additionally, 5P39 significantly attenuated the LPS-activated high expression of key proteins in TLR4/MyD88 signaling pathway. Taken together, the present study showed that 5P39 effectively alleviate the severity of ALI, and its mechanism might relate to the inhibition of LPS-activated TLR4/MyD88 signaling pathway, demonstrating a promising potential for further development into an anti-inflammatory drug candidate.
- He, Yanting,Zhao, Yalei,Feng, Yuchen,Ren, Anqi,Zhang, Yunyi,Wang, Yang,Li, Hong
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- The beneficial effects of Allicin in chronic kidney disease are comparable to Losartan
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Recent studies suggest that allicin may play a role in chronic kidney disease (CKD), reducing hypertension and oxidative stress and improving renal dysfunction. In the present study, CKD was induced by 5/6 nephrectomy and the animals were divided into four treatment groups as follows: control (C), CKD, CKD+allicin (40 mg/kg pathway oral) (CKDA), and CKD+Losartan (20 mg/kg) (CKDL). After CKD induction, the rats developed hypertension from week 3 to the end of the study. This was associated with increased creatinine and blood urea nitrogen (BUN) levels in serum, increased albuminuria, increased urinary excretion of N-acetyl-β-D-glucosaminidase (NAG), increased nephrin expression, and incrased histological alterations in the cortex. The levels of angiotensin receptors and endothelial nitric oxide synthase (eNOS) were decreased in the renal cortex from the CKD group. Otherwise, lipid and protein oxidation were higher in the CKD group than in the control group. A disturbance was observed in the expression levels of the nuclear factor erythroid 2-related factor 2/Kelch ECH associating protein 1 system (Nrf2/keap1) and the antioxidant enzymes catalase, superoxide dismutase, and heme oxygenase-1. Allicin or losartan treatments relieved renal dysfunction, hypertension, and oxidative stress. In addition, both treatments showed the same efficacy on the expression of angiotensin receptors, the nephrin, Nrf2/keap1 pathway, and eNOS. Further in silico analyses suggest that allicin and losartan could have a common mechanism involving interaction with AT1 receptors. Allicin showed antihypertensive, antioxidant, and nephroprotective effects. The beneficial effects showed by allicin are similar, or even better, than those of losartan. In fact, the effect of allicin on blood pressure and renal function is comparable to reductions seen with losartan, a prescription drug commonly used as a first-line therapy.
- García Trejo, Ehécatl Miguel ángel,Buendía, Abraham Said Arellano,Reyes, Omegar Sánchez,Arroyo, Fernando Enrique García,García, Raúl Arguello,Mendoza, María Lilia Loredo,Tapia, Edilia,Lozada, Laura Gabriela Sánchez,Alonso, Horacio Osorio
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- Hypochlorous acid scavenging activities of thioallyl compounds from garlic
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The hypochlorous acid (HOCl) scavenging capacities of 10 garlic compounds containing modifications in the thioallyl group (-S-CH2CH=CH 2) were determined by a catalase protection assay, and the corresponding structure-activity relationships using molecular descriptors were calculated. This scavenging activity was enhanced by increasing the number of S atoms or by the alanyl group (-CH2CH-NH2-COOH) and decreased in the absence of the C=C bond or in the presence of a sulfoxide group in the thioallyl group. Interestingly, S-allylcysteine and its corresponding sulfoxide (alliin) showed the highest and lowest HOCl-scavenging capacities, respectively. Quantitative modeling by multiple regression analysis and partial least-squares projections showed that the topological descriptor polar surface area and two electronic properties, namely, highest occupied molecular orbital and total energy, contributed mainly to variations in the HOCl scavenging activity of thioallyl compounds. These observations provide new insights on the antioxidant mechanism of garlic derivatives in processes involving HOCl production.
- Argueello-Garcia, Raul,Medina-Campos, Omar N.,Perez-Hernandez, Nury,Pedraza-Chaverri, Jose,Ortega-Pierres, Guadalupe
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- Garlic Chemistry: Stability of S-(2-Propenyl) 2-Propene-1-sulfinothioate (Allicin) in Blood, Solvents, and Simulated Physiological Fluids
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S-(2-Propenyl) 2-propene-1-sulfinothioate (allicin), which is one of the constituents of freshly crushed garlic (garlic homogenate), was synthesized, and its stability in blood, ethyl acetate, methanol, simulated gastric fluid (SGF, pH 1.2), simulated intestinal fluid (SIF, pH 7.5), and water (pH 1.2 and 7.5) and under simulated digestive conditions (sequential combination of SGF and SIF) was investigated by HPLC.Although neat allicin decomposes rapidly at 37 deg C, it is more stable in protic polar methanol than in aprotic polar ethyl acetate.Approximately 90percent of the allicin remained after incubation at 37 deg C for 5 h in water at pH 1.2 and 7.5.Only traces of allicin could be detected after it was incubated in blood for 5 min.The allicin content and allicin-producing potential of commercial garlic preparations were also analyzed.The allicin contents in these garlic preparations were less than 1 ppm, and the allicin-producing potential was severely suppressed under simulated digestive conditions (sequential combination of SGF and SIF).The transformation products of allicin were identified.Keywords: (E)-Ajoene; allicin; allicin content; allicin-producing potential; allicin stability; garlic preparations; 2-ethenyl-4H-1,3-dithiin, diallyl disulfide; garlic products
- Freeman, Fillmore,Kodera, Yukihiro
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- Allium sativum extract chemical composition, antioxidant activity and antifungal effect against meyerozyma guilliermondii and rhodotorula mucilaginosa causing onychomycosis
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Onychomycosis is a major health problem due to its chronicity and resistance to therapy. Because some cases associate paronychia, any therapy must target the fungus and the inflammation. Medicinal plants represent an alternative for onychomycosis control. In the present work the antifungal and antioxidant activities of Alium sativum extract against Meyerozyma guilliermondii (Wick.) Kurtzman & M. Suzuki and Rhodotorula mucilaginosa (A. J?rg.) F.C. Harrison, isolated for the first time from a toenail onychomycosis case, were investigated. The fungal species were confirmed by DNA molecular analysis. A. sativum minimum inhibitory concentration (MIC) and ultrastructural effects were examined. At the MIC concentration (120 mg/mL) the micrographs indicated severe structural alterations with cell death. The antioxidant properties of the A. sativum extract were evaluated is a rat turpentine oil induced inflammation, and compared to an anti-inflammatory drug, diclofenac, and the main compound from the extract, allicin. A. sativum reduced serum total oxidative status, malondialdehyde and nitric oxide production, and increased total thiols. The effects were comparable to those of allicin and diclofenac. In conclusion, the garlic extract had antifungal effects against M. guilliermondii and R. mucilaginosa, and antioxidant effect in turpentine-induced inflammation. Together, the antifungal and antioxidant activities support that A. sativum is a potential alternative treatment in onychomycosis.
- Parvu, Marcel,Mo?, C?t?lin A.,Parvu, Alina E.,Mircea, Cristina,Stoeber, Leander,Ro?ca-Casian, Oana,?igu, Adrian B.
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- Antimalarial activity of allicin, a biologically active compound from garlic cloves
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The incidence of malaria is increasing, and there is an urgent need to identify new drug targets for both prophylaxis and chemotherapy. Potential new drug targets include Plasmodium proteases that play critical roles in the parasite life cycle. We have previously shown that the major surface protein of Plasmodium sporozoites, the circumsporozoite protein (CSP), is proteolytically processed by a parasite-derived cysteine protease, and this processing event is temporally associated with sporozoite invasion of host cells. E-64, a cysteine protease inhibitor, inhibits CSP processing and prevents invasion of host cells in vitro and in vivo. Here we tested allicin, a cysteine protease inhibitor found in garlic extracts, for its ability to inhibit malaria infection. At low concentrations, allicin was not toxic to either sporozoites or mammalian cells. At these concentrations, allicin inhibited CSP processing and prevented sporozoite invasion of host cells in vitro. In vivo, mice injected with allicin had decreased Plasmodium infections compared to controls. When sporozoites were treated with allicin before injection into mice, malaria infection was completely prevented. We also tested allicin on erythrocytic stages and found that a 4-day regimen of allicin administered either orally or intravenously significantly decreased parasitemias and increased the survival of infected mice by 10 days. Together, these experiments demonstrate that the same cysteine protease inhibitor can target two different life cycle stages in the vertebrate host. Copyright
- Coppi, Alida,Cabinian, Melissa,Mirelman, David,Sinnis, Photini
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- Allicin induces thiol stress in bacteria through S-allylmercapto modification of protein cysteines
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Allicin (diallyl thiosulfinate) from garlic is a highly potent natural antimicrobial substance. It inhibits growth of a variety of microorganisms, among them antibiotic-resistant strains. However, the precise mode of action of allicin is unknown. Here, we show that growth inhibition of Escherichia coli during allicin exposure coincides with a depletion of the glutathione pool and S-allylmercapto modification of proteins, resulting in overall decreased total sulfhydryl levels. This is accompanied by the induction of the oxidative and heat stress response. We identified and quantified the allicin-induced modification S-allylmercaptocysteine for a set of cytoplasmic proteins by using a combination of label-free mass spectrometry and differential isotope-coded affinity tag labeling of reduced and oxidized thiol residues. Activity of isocitrate lyase AceA, an S-allylmercapto-modified candidate protein, is largely inhibited by allicin treatment in vivo. Allicin-induced protein modifications trigger protein aggregation, which largely stabilizes RpoH and thereby induces the heat stress response. At sublethal concentrations, the heat stress response is crucial to overcome allicin stress. Our results indicate that the mode of action of allicin is a combination of a decrease of glutathione levels, unfolding stress, and inactivation of crucial metabolic enzymes through S-allylmercapto modification of cysteines.
- Müller, Alexandra,Eller, Jakob,Albrecht, Frank,Prochnow, Pascal,Kuhlmann, Katja,Bandow, Julia Elisabeth,Slusarenko, Alan John,Leichert, Lars Ingo Ole
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- Garlic: Source of the ultimate antioxidants - Sulfenic acids
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(Chemical Equation Presented) The medicinal properties of garlic, thought to derive at least in part from the antioxidant activity of its sulfur-containing secondary metabolites, have been recognized for hundreds of years. The ability of garlic to scavenge peroxyl radicals can be accounted for in terms of the action of transient sulfenic acids, which are predicted to react by diffusion-controlled five-center proton-coupled electron transfer (see scheme and transition state).
- Vaidya, Vipraja,Ingold, Keith U.,Pratt, Derek A.
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- Subinhibitory concentrations of allicin decrease uropathogenic escherichia coli (UPEC) biofilm formation, adhesion ability, and swimming motility
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Uropathogenic Escherichia coli (UPEC) biofilm formation enables the organism to avoid the host immune system, resist antibiotics, and provide a reservoir for persistent infection. Once the biofilm is established, eradication of the infection becomes difficult. Therefore, strategies against UPEC biofilm are urgently required. In this study, we investigated the effect of allicin, isolated from garlic essential oil, on UPEC CFT073 and J96 biofilm formation and dispersal, along with its effect on UPEC adhesion ability and swimming motility. Sub-inhibitory concentrations (sub-MICs) of allicin decreased UPEC biofilm formation and affected its architecture. Allicin was also capable of dispersing biofilm. Furthermore, allicin decreased the bacterial adhesion ability and swimming motility, which are important for biofilm formation. Real-time quantitative polymerase chain reaction (RT-qPCR) revealed that allicin decreased the expression of UPEC type 1 fimbriae adhesin gene fimH. Docking studies suggested that allicin was located within the binding pocket of heptyl —-D-mannopyrannoside in FimH and formed hydrogen bonds with Phe1 and Asn135. In addition, allicin decreased the expression of the two-component regulatory systems (TCSs) cognate response regulator gene uvrY and increased the expression of the RNA binding global regulatory protein gene csrA of UPEC CFT073, which is associated with UPEC biofilm. The findings suggest that sub-MICs of allicin are capable of affecting UPEC biofilm formation and dispersal, and decreasing UPEC adhesion ability and swimming motility.
- Yang, Xiaolong,Sha, Kaihui,Xu, Guangya,Tian, Hanwen,Wang, Xiaoying,Chen, Shanze,Wang, Yi,Li, Jingyu,Chen, Junli,Huang, Ning
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- Characterization of phenolic constituents inhibiting the formation of sulfur-containing volatiles produced during garlic processing
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Garlic (Allium sativum L.), which is a widely distributed plant, is globally used as both spice and food. This study identified five novel phenolic compounds, namely, 8-(3-methyl-(E)-1-butenyl)diosmetin, 8-(3-methyl-(E)-1-butenyl)chrysin, 6-(3-methyl-(E)-1-butenyl)chrysin, and Alliumones A and B, along with nine known compounds 6-14 from the ethanol extract of garlic. The structures of these five novel phenolic compounds were established via extensive 1D- and 2D-nuclear magnetic resonance spectroscopy experiments. The effects of the phenolic compounds isolated from garlic on the enzymatical or nonenzymatical formation of sulfur-containing compounds produced during garlic processing were examined. Compound 12 significantly reduced the thermal decomposition of alliin, whereas compound 4 exhibited the highest percentage of alliinase inhibition activity (36.6%).
- Li, Wen-Qing,Zhou, Hua,Zhou, Mei-Yun,Hu, Xing-Peng,Ou, Shi-Yi,Yan, Ri-An,Liao, Xiao-Jian,Huang, Xue-Song,Fu, Liang
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- Application of allicin in preparation of anti-saccharomycetes drugs
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The invention provides application of allicin in preparation of anti-saccharomycetes drugs, and relates to the technical field of medicines. Experiments show that the allicin has a good antibacterial effect on cryptococcus and candida, and the allicin combined with the antifungal drug also has good antibacterial activity on cryptococcus and candida. Experiments also show that allicin achieves a bacteriostatic or bactericidal effect by destroying capsules or cell walls or cell membranes of cryptococcus. The allicin has better activity against cryptococcus in vivo and in vitro. The allicin preparation can be used as a medicine which is safe, effective, small in toxic and side effects and low in price and is used for clinically treating fungal infectious diseases.
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Paragraph 0035-0037
(2021/07/14)
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- Oxygen-to-Oxygen Silyl Migration of α-Siloxy Sulfoxides and Oxidation-Triggered Allicin Formation
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Oxidation of α-siloxy thioethers leads to the formation of the corresponding sulfoxides as unstable intermediates, which undergo an intramolecular oxygen-to-oxygen silyl migration to break the C-S linkage. This process produces silyl protected sulfenic acids and subsequently thiosulfinates. It was used to develop oxidation-triggered allicin donors.
- Kelly, Shane S.,Shen, Tun-Li,Xian, Ming
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supporting information
p. 3741 - 3745
(2021/05/10)
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- Effect of physicochemical parameters on the stability and activity of garlic alliinase and its use for in-situ allicin synthesis
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Garlic is a well-known example of natural self-defence system consisting of an inactive substrate (alliin) and enzyme (alliinase) which, when combined, produce highly antimicrobial allicin. Increase of alliinase stability and its activity are of paramount importance in various applications relying on its use for in-situ synthesis of allicin or its analogues, e.g., pulmonary drug delivery, treatment of superficial injuries, or urease inhibitors in fertilizers. Here, we discuss the effect of temperature, pH, buffers, salts, and additives, i.e. antioxidants, chelating agents, reducing agents and cosolvents, on the stability and the activity of alliinase extracted from garlic. The effects of the storage temperature and relative humidity on the stability of lyophilized alliinase was demonstrated. A combination of the short half-life, high reactivity and non-specificity to particular proteins are reasons most bacteria cannot deal with allicin's mode of action and develop effective defence mechanism, which could be the key to sustainable drug design addressing serious problems with escalating emergence of multidrug-resistant (MDR) bacterial strains.
- Janska, Petra,Knejzlík, Zdenek,Perumal, Ayyappasamy Sudalaiyadum,Jurok, Radek,Tokarova, Viola,Nicolau, Dan V.,Tepanek, FrantisekS,Kaspar, Ondrej
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- Tanshinol and H2 S/NO Donor binding, preparation method thereof and application in pharmacy (by machine translation)
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The invention belongs to the field of chemical pharmacy, and relates to active ingredient tanshinol and H in Chinese herbal medicine Salvia miltiorrhiza. 2 S/NO Donors and its preparation method and use in pharmacy, especially in the preparation of medicines for preventing and treating cardiovascular and cerebrovascular diseases and inflammation related diseases. To the invention, through in-vitro oxidative stress injury and inflammation model experiments, the results show that H is obviously inhibited. 2 O2 In vivo activity experiment results show that the conjugate is capable of remarkably inhibiting the release of inflammatory cytokines induced by LPS (LPS), reducing inflammation-induced mouse peritoneal macrophages, obviously inhibiting the release of inflammatory cytokines induced by LPS, and showing the result that the compound can be used for preparing drugs for preventing and treating cardiovascular and cerebrovascular diseases and inflammatory diseases. (by machine translation)
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Paragraph 0116-0118
(2020/08/18)
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- Selective Oxidation of Sulfides in Flow Chemistry
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A packed-bed reactor with oxone has been employed for selective oxidations of sulfur compounds. Various sulfides containing different functional groups are efficiently oxidized to the corresponding sulfoxides without formation of sulfones or other side products.
- Silva, Filipa,Baker, Alastair,Stansall, James,Michalska, Weronika,Yusubov, Mehkman S.,Graz, Michael,Saunders, Robert,Evans, Gareth J. S.,Wirth, Thomas
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supporting information
p. 2134 - 2137
(2018/05/31)
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- Synthesis and in vitro biological evaluation of thiosulfinate derivatives for the treatment of human multidrug-resistant breast cancer
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Organosulfur compounds derived from Allium vegetables have long been recognized for various therapeutic effects, including anticancer activity. Allicin, one of the main biologically active components of garlic, shows promise as an anticancer agent; however, instability makes it unsuitable for clinical application. The aim of this study was to investigate the effect of stabilized allicin derivatives on human breast cancer cells in vitro. In this study, a total of 22 stabilized thiosulfinate derivatives were synthesized and screened for their in vitro antiproliferative activities against drug-sensitive (MCF-7) and multidrug-resistant (MCF-7/Dx) human adenocarcinoma breast cancer cells. Assays for cell death, apoptosis, cell cycle progression and mitochondrial bioenergetic function were performed. Seven compounds (4b, 7b, 8b, 13b, 14b, 15b and 18b) showed greater antiproliferative activity against MCF-7/Dx cells than allicin. These compounds were also selective towards multidrug-resistant (MDR) cells, a consequence attributed to collateral sensitivity. Among them, 13b exhibited the greatest anticancer activity in both MCF-7/Dx and MCF-7 cells, with IC50 values of 18.54±0.24 and 46.50±1.98 μmol/L, respectively. 13b altered cellular morphology and arrested the cell cycle at the G2/M phase. Additionally, 13b dose-dependently induced apoptosis, and inhibited cellular mitochondrial respiration in cells at rest and under stress. MDR presents a significant obstacle to the successful treatment of cancer clinically. These results demonstrate that thiosulfinate derivatives have potential as novel anticancer agents and may offer new therapeutic strategies for the treatment of chemoresistant cancers.
- Roseblade, Ariane,Ung, Alison,Bebawy, Mary
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p. 1353 - 1368
(2017/10/10)
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- Disulfide Bond-Containing Ajoene Analogues As Novel Quorum Sensing Inhibitors of Pseudomonas aeruginosa
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Since its discovery 22 years ago, the bacterial cell-to-cell communication system, termed quorum sensing (QS), has shown potential as antipathogenic target. Previous studies reported that ajoene from garlic inhibits QS in opportunistic human pathogen Pseudomonas aeruginosa. In this study, screening of an in-house compound library revealed two sulfur-containing compounds which possess structural resemblance with ajoene and inhibit QS in bioreporter assay. Following a quantitative structure-activity relationship (SAR) study, 25 disulfide bond-containing analogues were synthesized and tested for QS inhibition activities. SAR study indicated that the allyl group could be replaced with other substituents, with the most active being benzothiazole derivative (IC50 = 0.56 μM). The compounds were able to reduce QS-regulated virulence factors (elastase, rhamnolipid, and pyocyanin) and successfully inhibit P. aeruginosa infection in murine model of implant-associated infection. Altogether, the QS inhibition activity of the synthesized compounds is encouraging for further exploration of novel analogues in antimicrobial drug development.
- Fong, July,Yuan, Mingjun,Jakobsen, Tim Holm,Mortensen, Kim T.,Delos Santos, May Margarette Salido,Chua, Song Lin,Yang, Liang,Tan, Choon Hong,Nielsen, Thomas E.,Givskov, Michael
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p. 215 - 227
(2017/04/26)
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- Oxidation of disulfides to thiolsulfinates with hydrogen peroxide and a cyclic seleninate ester catalyst peroxide and a cyclic seleninate ester catalyst
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Cyclic seleninate esters function as mimetics of the antioxidant selenoenzyme glutathione peroxidase. They catalyze the reduction of harmful peroxides with thiols, which are converted to disulfides in the process. The possibility that the seleninate esters could also catalyze the further oxidation of disulfides to thiolsulfinates and other overoxidation products under these conditions was investigated. This has ramifications in potential medicinal applications of seleninate esters because of the possibility of catalyzing the unwanted oxidation of disulfide-containing spectator peptides and proteins. A variety of aryl and alkyl disulfides underwent facile oxidation with hydrogen peroxide in the presence of catalytic benzo-1,2-oxaselenolane Se-oxide affording the corresponding thiolsulfinates as the principal products. Unsymmetrical disulfides typically afforded mixtures of regioisomers. Lipoic acid and N,N′-dibenzoylcystine dimethyl ester were oxidized readily under similar conditions. Although isolated yields of the product thiolsulfinates were generally modest, these experiments demonstrate that the method nevertheless has preparative value because of its mild conditions. The results also confirm the possibility that cyclic seleninate esters could catalyze the further undesired oxidation of disulfides in vivo.
- McNeil, Nicole M. R.,McDonnell, Ciara,Hambrook, Miranda,Back, Thomas G.
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p. 10748 - 10762
(2015/08/11)
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- PREPARING METHOD OF ALLICIN INJECTION AND LOW TEMPERATURE CONTINUOUS STIRRING ULTRAFILTRATION DEVICE THEREOF
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The present invention provides a preparing method of an allicin injection and the low temperature continuous stirring ultrafiltration device thereof. Said preparing method consists of the following steps: extracting allicin; diluting the allicin with solvent precooled tol-4°C in a clean environment, adding nitrogen gas or argon gas, and then encapsulating the solution to obtain allicin injection with different specifications.
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Paragraph 0062; 0063; 0064; 0065; 0066; 0067
(2015/12/08)
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- A tissue homogenate method to prepare gram-scale allium thiosulfinates and their disulfide conjugates with cysteine and glutathione
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The health benefits of Allium vegetables are widely attributed to the enzyme-derived organosulfur compounds called thiosulfinates (TS). However, the lack of a suitable method to prepare TS in good yields has hampered the evaluation of their biological activities. This paper describe a simple enzymatic method using Allium tissue homogenates as a reaction system to prepare gram-scale TS, including those enriched in 1-propenyl groups, which are particularly difficult to obtain. This method is simple, easy to scale up, and requires no column purification step, making it suitable for practical large-scale production of Allium TS. The prepared TS were further utilized to prepare the disulfide conjugates with cysteine and glutathione (CySSR and GSSR, R = methyl, ethyl, propyl, 1-propenyl, and allyl), which are the presumptive metabolites of TS. Among all of the Allium CySSR and GSSR conjugates, the newly prepared glutathione conjugate with 1-propenyl TS, GSSPe, showed the most potent effect to induce quinone reductase (QR, a representative phase II enzyme) in murine hepatoma cells (Hepa 1c1c7) and inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated macrophage cells (RAW 264.7).
- Zhang, Guodong,Parkin, Kirk L.
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p. 3030 - 3038
(2013/08/25)
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- PROCESS FOR THE MANUFACTURE OF AJOENE DERIVATIVES
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The present invention relates to the compound (E,Z)-ajoene of formula (1) for use in treatment of bacterial infections. Another aspect of the present invention is a composition comprising (E,Z)-ajoene of formula (1) and at least one antibiotic. Yet another aspect of the invention relates to a method for manufacturing (E,Z) ajoene of formula (1) wherein the conformation of the internal C=C- bond can be either E or Z or a mixture thereof, said method comprising reacting allicin of formula (3) with an acid in the presence of a solvent to provide (E,Z ajoene) of formula (1) as defined above. Yet another aspect of the invention is (E,Z)-ajoene of formula 1 obtainable by the method described above.
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Page/Page column 18
(2012/06/30)
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- First insights into the mode of action of a "lachrymatory factor synthase" - Implications for the mechanism of lachrymator formation in Petiveria alliacea, Allium cepa and Nectaroscordum species
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A study of an enzyme that reacts with the sulfenic acid produced by the alliinase in Petiveria alliacea L. (Phytolaccaceae) to yield the P. alliacea lachrymator (phenylmethanethial S-oxide) showed the protein to be a dehydrogenase. It functions by abstracting hydride from sulfenic acids of appropriate structure to form their corresponding sulfines. Successful hydride abstraction is dependent upon the presence of a benzyl group on the sulfur to stabilize the intermediate formed on abstraction of hydride. This dehydrogenase activity contrasts with that of the lachrymatory factor synthase (LFS) found in onion, which catalyzes the rearrangement of 1-propenesulfenic acid to (Z)-propanethial S-oxide, the onion lachrymator. Based on the type of reaction it catalyzes, the onion LFS should be classified as an isomerase and would be called a "sulfenic acid isomerase", whereas the P. alliacea LFS would be termed a "sulfenic acid dehydrogenase".
- He, Quan,Kubec, Roman,Jadhav, Abhijit P.,Musah, Rabi A.
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experimental part
p. 1939 - 1946
(2012/01/13)
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- PROCESS FOR THE PREPARATION OF AJOENE
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The present invention is directed to a process for the preparation of ajoene, and to ajoene having a relatively high purity which may be obtained by the process. The invention also relates to processes for the preparation of allicin, to a process for freeze concentrating allicin.
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Page/Page column 22-23
(2010/09/18)
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- Allicin and derivates are cysteine protease inhibitors with antiparasitic activity
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Allicin and derivatives thereof inhibit the CAC1 cysteine proteases falcipain 2, rhodesain, cathepsin B and L in the low micromolar range. The structure-activity relationship revealed that only derivatives with primary carbon atom in vicinity to the thiosulfinate sulfur atom attacked by the active-site Cys residue are active against the target enzymes. Some compounds also show potent antiparasitic activity against Plasmodium falciparum and Trypanosoma brucei brucei.
- Waag, Thilo,Gelhaus, Christoph,Rath, Jennifer,Stich, August,Leippe, Matthias,Schirmeister, Tanja
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supporting information; experimental part
p. 5541 - 5543
(2010/12/25)
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- Methods and compositions for malaria prophylaxis
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A composition for preventing malaria infection including a protease inhibitor. A pharmaceutical composition for preventing malaria infection including a protease inhibitor and a pharmaceutical carrier. A method of malaria infection prophylaxis including the step of administering an effective amount of the composition of the present invention. A method of malaria prophylaxis by inhibiting circumsporozoite protein processing or by inhibiting a protease of a sporozoite. Methods of preventing sporozoite cell invasion or preventing circumsporozoite processing.
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Page/Page column 5
(2008/06/13)
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- Medicinal products incorporating bound organosulfur groups
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Nutraceutical and dietary supplement formulations for delivering bioavailable thiols to a host, comprising certain organosulfur radicals, such as the allyl mercapto radical, bound to larger molecules such as proteins, resulting in the formation in the host's body of various allium-related compounds such as allicin. The formulations are produced by treating an ingestible material comprising a cysteine-containing protein with a thiol, disulfide, mixed disulfide, thiosufinate or mixed thiosulfinate so as to cause thiol residues to become disulfide bonded to cysteines contained in the protein.
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Page/Page column 25; Sheet 7
(2008/06/13)
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- Mechanism and kinetics of synthesis of allicin
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Allicin, allyl-thiosulfinate, a pharmacologically active compound with considerable fungicidal, bactericidal, antioxidant and anticarcinogenic effects, was obtained by oxidizing allyl disulfide with acid hydrogen peroxide. The synthesis mechanism was studied by the ESR spin trap method. The kinetics of allicin synthesis was ascertained by determination of the concentration of the limiting reactant during the synthesis using HPLC and it was found that the allicin synthesis reaction was of zero order. The allicin obtained was determined using UV, FT-IR, MS, 1H and 13C NMR analysis.
- Nikolic, Vesna,Stankovic,Nikolic,Cvetkovic
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- RELATION BETWEEN THE STRUCTURE OF ALLIIN ANALOGUES AND THEIR INHIBITORY EFFECT ON PLATELET AGGREGATION
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Key Word Index - Alliin; S-allyl-L-cysteine sulphoxide; allicin; dihydroalliin; platelet aggregation inhibitors. - Alliin analogues have been synthesized and tested for their inhibitory activity on platelet aggregation.It is found that only allicin, the S-oxodiallyl disulphide, has a strong inhibitory effect, comparable to that of alliin, while all the other tested compounds do not show any inhibitory effect even at concentrations of 10-3 M.
- Liakopoulou-Kyriakides, M.
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p. 1593 - 1594
(2007/10/02)
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- (E,Z)-Ajoene: A potent antithrombotic agent from garlic
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A report is presented of the structural characterization and simple synthesis of (E,Z)-ajoene.
- Block,Ahmad,Jain,et al.
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p. 8295 - 8296
(2007/10/02)
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