- Inhibitory effect of gallic acid and its esters on 2,2'-azobis(2- amidinopropane)hydrochloride (AAPH)-induced hemolysis and depletion of intracellular glutathione in erythrocytes
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The protective effect of gallic acid and its esters, methyl, propyl, and lauryl gallate, against 2,2'-azobis(2-amidinopropane)hydrochloride (AAPH)-induced hemolysis and depletion of intracellular glutathione (GSH) in erythrocytes was studied. The inhibition of hemolysis was dose-dependent, and the esters were significantly more effective than gallic acid. Gallic acid and its esters were compared with regard to their reactivity to free radicals, using the DPPH and AAPH/pyranine free-cell assays, and no significant difference was obtained. Gallic acid and its esters not only failed to inhibit the depletion of intracellular GSH in erythrocytes induced by AAPH but exacerbated it. Similarly, the oxidation of GSH by AAPH or horseradish peroxidase/H 2O2 in cell-free systems was exacerbated by gallic acid or gallates. This property could be involved in the recent findings on pro-apoptotic and pro-oxidant activities of gallates in tumor cells. We provide evidence that lipophilicity and not only radical scavenger potency is an important factor regarding the efficiency of antihemolytic substances.
- Ximenes, Valdecir F.,Lopes, Mariana G.,Petronio, Maicon Segalla,Regasini, Luis Octavio,Siqueira Silva, Dulce H.,Da Fonseca, Luiz M.
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- Design, Synthesis, and Antifungal Activity of Alkyl Gallates Against Plant Pathogenic Fungi In Vitro and In Vivo
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A series of alkyl gallates was synthesized by reacting gallic acid with the corresponding alcohols. Their structures were determined on the basis of spectroscopic data, including NMR and MS. The antifungal activities of these compounds against plant pathogenic fungi in vitro and in vivo were assessed.
- Zhao, Xiao-Long,Li, Chun-Qing,Song, Xiao-Mei,Yan, Shuang-Mei,Luo, Du-Qiang
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- Synthetic method of dodecyl gallate
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The invention relates to a synthesis method of dodecanoyl gallate. The synthesis method comprises the following steps: 1) carrying out a primary reaction to obtain a dodecanoyl gallate crude product and an applied mother liquor; 2) applying the mother liquor to obtain a dodecanoyl gallate crude product; and 3) preparing a dodecanoyl gallate refined product by combining the crude product. The preparation method mainly comprises the following steps: carrying out a primary reaction on anhydrous gallic acid and a dodecanol to obtain a crude product and a mother liquor, carrying out an applying reaction on anhydrous gallic acid, dodecanol and the mother liquor to obtain a dodecanoyl gallate crude product, and finally preparing the refined product from the crude products obtained by the two reactions. The reaction synthesis method is simple, the raw material utilization rate is high, the product purity can reach more than 99%, and the product yield can reach more than 75%.
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Paragraph 0022-0025
(2020/06/17)
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- Development of a Gemini Interfacial Antioxidant for Oil in Water Emulsion with Gallic Acid and Dodecyl Gemini Chains
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In this study, development of the gemini gallate (GG) interfacial antioxidant for oil in water (O/W) emulsion was performed employing Steglich esterification with gallic acid and dodecyl gemini chains through a prepacked column and peristaltic pump-based purification system. The structural identity and purity of the prepared GG and monogallate (MG) were confirmed by NMR, Fourier transform infrared spectroscopy, and high-performance liquid chromatography-mass spectrometry. Further evaluation revealed that the GG possessed excellent radical scavenging activity and superior antioxidant activity in an O/W emulsion relative to the MG, especially under the condition of a reduced amount of the emulsifier. Microscopic investigation by a fluorescent probe and transmission electron microscopy (TEM) unveiled that the extraordinary antioxidant performance in the O/W emulsion was presumably attributed to preferable interfacial location because of the unique gemini molecular architecture. The superior antioxidant activity of the gemini antioxidant holds great promise for antioxidation in O/W emulsions.
- Liu, Songbai,Wang, Peifei
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p. 9953 - 9960
(2020/10/26)
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- Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors
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Linear and branched compounds that contain two, three or five units of galloyl (3,4,5-trihydroxybenzoyl) or its isomer 2,3,4-trihydroxybenzoyl, as well as other mono- or dihydroxybenzoyl moieties have been synthesized. These molecules have been evaluated for their in vitro inhibitory effects against a wide panel of viruses showing preferential activity against HIV and HCV. Our structure-activity relationship studies demonstrated that the 2,3,4-trihydroxybenzoyl moiety provides better antiviral activities than the galloyl (3,4,5-trihydroxybenzoyl) moiety that is present in natural green tea catechins. This observation can be of interest for the further rational exploration of compounds with anti-HCV/HIV properties. The most notable finding with respect to HIV is that the tripodal compounds 43 and 45, with three 2,3,4-trihydroxybenzoyl moieties, showed higher activities than linear compounds with only one or two. With respect to HCV, the linear compounds, 52 and 41, containing a 12 polymethylene chain and two 2,3 di- or 2,3,4 tri-hydroxybenzoyl groups respectively at the ends of the molecule showed good antiviral efficiency. Furthermore, the anti-HCV activity of both compounds was observed at concentrations well below the cytotoxicity threshold. A representative member of these compounds, 41, showed that the anti-HCV activity was largely independent of the genetic make-up of the HCV subgenomic replicon and cell lines used.
- Rivero-Buceta, Eva,Carrero, Paula,Doyagüez, Elisa G.,Madrona, Andrés,Quesada, Ernesto,Camarasa, María José,Peréz-Pérez, María Jesús,Leyssen, Pieter,Paeshuyse, Jan,Balzarini, Jan,Neyts, Johan,San-Félix, Ana
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p. 656 - 671
(2015/01/30)
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- Antifungal activity of alkyl gallates against plant pathogenic fungi
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The antifungal activity of alkyl gallates against plant pathogenic fungi was evaluated. All of the fungi tested in this study were susceptible to some alkyl gallates, and the effect of linear alkyl gallates against plant pathogenic fungi was similar to the previously reported effects against Gram-negative and Gram-positive bacteria. We found that branched alkyl gallates showed stronger activity than did linear alkyl gallates with similar log P values. In addition, the antifungal activity of alkyl gallates was correlated with gallate-induced inhibition of the activity of mitochondrial complex II. The antifungal activity of alkyl gallates likely originates, at least in part, from their ability to inhibit the membrane respiratory chain.
- Ito, Shinsaku,Nakagawa, Yasutaka,Yazawa, Satoru,Sasaki, Yasuyuki,Yajima, Shunsuke
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p. 1812 - 1814
(2014/04/17)
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- Alkyl hydroxybenzoic acid derivatives that inhibit HIV-1 protease dimerization
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The therapeutic potential of gallic acid and its derivatives as anti-cancer, antimicrobial and antiviral agents is well known. We have examined the mechanism by which natural gallic acid and newly synthesized gallic acid alkyl esters and related protocatechuic acid alkyl esters inhibit HIV-1 protease to compare the influence of the aromatic ring substitutions on inhibition. We used Zhang-Poorman's kinetic analysis and fluorescent probe binding to demonstrate that several gallic and protecatechuic acid alkyl esters inhibited HIV-1 protease by preventing the dimerization of this obligate homodimeric aspartic protease rather than targeting the active site. The tri-hydroxy substituted benzoic moiety in gallates was more favorable than the di-substituted one in protocatechuates. In both series, the type of inhibition, its mechanism and the inhibitory efficiency dramatically depended on the length of the alkyl chain: no inhibition with alkyl chains less than 8 carbon atoms long. Molecular dynamics simulations corroborated the kinetic data and propose that gallic esters are intercalated between the two N- and C-monomer ends. They complete the β-sheet and disrupt the dimeric enzyme. The best gallic ester (14 carbon atoms, Kid of 320 nM) also inhibited the multi-mutated protease MDR-HM. These results will aid the rational design of future generations of non-peptide inhibitors of HIV-1 protease dimerization that inhibit multi-mutated proteases. Finally, our work suggests the wide use of gallic and protocatechuic alkyl esters to dissociate intermolecular β-sheets involved in protein-protein interactions.
- Flausino Jr., O. A.,Dufau, L.,Reboud-Ravaux, M.,Regasini, L. O.,Petronio, M. S.,Silva, D. H. S.,Bolzani, V. S.,Rose, T.
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p. 4534 - 4540,7
(2012/12/12)
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- Antiproliferative and apoptosis-inducing activities of alkyl gallate and gallamide derivatives related to (-)-epigallocatechin gallate
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Green tea and (-)-epigallocatechin gallate (EGCG: one of the main components of green tea) are reported to have cancer-preventive activity in humans. A previous SAR study of EGCG and derivatives indicated that a galloyl group is essential for the activity. To test this hypothesis, we synthesized various alkyl gallate and gallamide derivatives and evaluated their antiproliferative effects on human leukemia HL-60 cells. Dodecyl 3,4,5-trihydroxybenzoate (6c) showed the most potent activity, being more potent than EGCG. To clarify the molecular mechanism of the antiproliferative action, we investigated the effects of 6c on various factors. Compound 6c was found to induce apoptosis mediated by endoplasmic reticulum (ER)-stress-related caspase-12. Upregulation of gadd-153, an ER-stress marker protein, was also observed. These results indicate that 6c induced apoptosis via the ER-stress-related pathway.
- Dodo, Kosuke,Minato, Taro,Noguchi-Yachide, Tomomi,Suganuma, Masami,Hashimoto, Yuichi
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p. 7975 - 7982
(2008/12/23)
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- Antifeeding method against insects
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Wooden material can be protected by applying a C8-C12 alkyl ester of gallic acid to the wooden material from feeding by insects.
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Page/Page column 3
(2008/06/13)
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- Evaluation of anti-herpetic and antioxidant activities, and cytotoxic and genotoxic effects of synthetic alkyl-esters of gallic acid
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The n-alkyl esters of gallic acid (CAS 138-57-8) have a diverse range of uses as anti-oxidants in food, cosmetics and pharmaceutical industries. Pharmaceutical studies performed with these compounds have found that they have many therapeutic potentialities including anti-cancer, antiviral and antimicrobial properties. However, more interest has been devoted to their antioxidant activity due to the ability to scavenge and reduce reactive oxygen species (ROS) formation. In this study, gallic acid and 14 different alkyl gallates were tested. The cytotoxicity and anti-herpetic (HSV-1, KOS and 29-R strains) activity were studied by using the MTT (3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide) colorimetric assay and the cell viability by using the Trypan blue dye exclusion method. The genotoxicity was studied by the Comet assay and the antioxidant activity by using the DPPH (1,1-diphenyl-2- picrylhydrazyl) radical scavenging and microsomal lipid peroxidation-inhibiting activities. The results showed that all the tested compounds have anti-herpetic activity at non cytotoxic concentrations with selectivity indices (SI = CC 50/EC50) varying from 0.89 to 18.34, depending on the used HSV-1 strain. It was observed that all tested alkyl gallates showed some degree of genotoxicity, at the tested concentrations, except cetyl gallate, at 256.60 μmol/L (p 50 values varying from 17 to 31 μmol/L; and microsomal lipid peroxidation-inhibiting activity with IC50 values varying from 21 to 59 μmol/L. It was observed that the presence of hydroxyl groups in these molecules is important for their pharmacological profile, but the length of the lateral carbonic chain does not have considerable influence.
- Savi, Luciane A.,Leal, Paulo C.,Vieira, Tiago O.,Rosso, Rober,Nunes, Ricardo J.,Yunes, Rosendo A.,Creczynski-Pasa, Tania B.,Barardi, Celia R. M.,Simoes, Claudia Maria Oliveira
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- Thermosensitive recording material and color developer compound therefor
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A thermosensitive recording material has a support and a thermosensitive coloring layer formed thereon containing a leuco dye and a color developer capable of inducing color formation in the leuco dye upon application of heat thereto, with the color developer including at least one compound (A) having in a molecule thereof at least two aromatic ring moieties with specific structures, selected from the group consisting of an aromatic ring moiety having at least one carboxyl group and electron-attracting functional group, an aromatic ring moiety having at least one carboxyl group and electron-donating functional group, and an aromatic ring moiety having at least one carboxyl group, free of the electron-attracting and electron-donating functional groups. An aromatic carboxylic acid compound serving as the above-mentioned compound (A) and the producing method thereof are also disclosed.
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- Molecular design of antifungal agents
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In a rational approach to the design of antifungal agents against Saccharomyces cerevisiae, a series of alkyl gallates (3,4,5-trihydroxybenzoates) were synthesized and assayed. Nonyl gallate (1) was found to be the most effective with a minimum fungicidal concentration (MFC) of 12.5 μg/mL (42 μM), followed by octyl gallate (2) with an MFC of 25 μg/mL (89 μM). These MFCs are little influenced by pH values. A time-kill curve study indicates that nonyl gallate exhibits fungicidal activity against S. cerevisiae at any growing stage. The antifungal activity of nonyl gallate is due primarily to its ability to act as a nonionic surface-active agent (surfactant). The length of the alkyl group is not a major contributor but plays a role in eliciting the activity to a large extent. As far as alkyl gallates are concerned, their antimicrobial spectra and potency depend largely on the hydrophobic portion of the molecules.
- Kubo, Isao,Xiao, Ping,Nihei, Ken-Ichi,Fujita, Ken-Ichi,Yamagiwa, Yoshiro,Kamikawa, Tadao
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p. 3992 - 3998
(2007/10/03)
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- Anti-Salmonella activity of alkyl gallates
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A series of alkyl gallates (3,4,5-trihydroxybenzoates) was synthesized and tested for their antibacterial activity against Salmonella choleraesuis. Nonyl (C9) and octyl (C8) gallates were noted to be the most effective against this food-borne bacterium, each with a minimum bactericidal concentration (MBC) of 12.5 μg/mL, followed by decyl (C10) gallate, with a MBC of 25 μg/mL. Dodecyl (C12) gallate exhibited activity against S. choleraesuis, with a MBC of 50 μg/mL. Propyl (C3) gallate showed no activity against S. choleraesuis up to 3200 μg/mL. The length of the alkyl group is not a major contributor but plays a role in eliciting the activity to a large extent. The same series of alkyl gallates, regardless of alkyl chain length, all showed nearly the same potent scavenging activity on the 1,1-diphenyl-2-picrylhydrazyl radical, indicating that the length of the alkyl group is not associated with the activity.
- Kubo, Isao,Fujita, Ken-Ichi,Nihei, Ken-Ichi
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p. 6692 - 6696
(2007/10/03)
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- Antifungal activity of octyl gallate: Structural criteria and mode of action
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Octyl gallate (3,4,5-trihydroxybenzoate) was found to possess antifungal activity against Saccharomyces cerevisiae and Zygosaccharomyces bailii, in addition to its potent antioxidant activity. Catechol moiety is essential to elicit this activity. The primary fungicidal activity of octyl gallate comes from its ability to act as a nonionic surface-active agent (surfactant). The length of the alkyl chain is not a major contributor but plays an important role in eliciting the activity.
- Kubo, Isao,Xiao, Ping,Fujita, Ken'ichi
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p. 347 - 350
(2007/10/03)
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- Phenolic compounds
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A phenolic compound having formula (I): STR1 wherein X represents a chlorine atom or a methyl group, and a recording material comprising a coloress or light-colored leuco dye and the above phenolic compound serving as a color developer for the leuco dye are disclosed.
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