- 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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Read Online
- Molecular design of antibrowning agents
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Tyrosinase inhibitory and antioxidant activity of gallic acid and its series of alkyl chain esters were investigated. All inhibited the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by mushroom tyrosinase. However, gallic acid and its short alkyl chain esters were oxidized as substrates yielding the colored oxidation products. In contrast, the long alkyl chain esters inhibited the enzyme activity without being oxidized. This indicates that the carbon chain length is associated with their tyrosinase inhibitory activity, presumably by interacting with the hydrophobic protein pocket in the enzyme. On the other hand, the esters, regardless their carbon chain length, showed potent scavenging activity on the autoxidation of linoleic acid and 1,1-diphenyl-2-p-picryhydrazyl (DPPH) radical, suggesting that the alkyl chain length is not related to the activity. The effects of side-chain length of gallates in relation to their antibrowning activity are studied.
- Kubo, Isao,Kinst-Hori, Ikuyo,Kubo, Yumi,Yamagiwa, Yoshiro,Kamikawa, Tadao,Haraguchi, Hiroyuki
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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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- A preparation method of electronic grade gallic octyl ester
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The present invention provides a kind of electronic grade gallic octyl ester of preparation method, which belongs to the technical field of organic synthesis. The gallic acid dissolved in alcohol, then drop adds the chlorination [...], then adding aromatic hydrocarbon solvent, a catalytic amount of B (C6F5) 3 and octanol, moiety will be distillation after the exchange, getting the gallic octyl ester. This method avoids the use of heavy metal catalyst, high yield, low cost, and is suitable for industrial scale production, the ester exchange after the end of the added metal ion adsorbent after the metal ion adsorption, distillation electronic level of gallic octyl ester.
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- Synthesis and in vitro antimalarial activity of alkyl esters of gallate as a growth inhibitor of plasmodium falciparum
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This study is aimed to synthesize alkyl esters gallate and determine its in vitro antimalarial activity against parasite Plasmodium falciparum. Fourteen compounds of alkyl esters gallate were synthesized by esterification of the carboxyl group of gallic acid with a series of alkyl alcohols, as well as methoxylation of the hydroxy groups on the aromatic ring of gallic acid. Antimalarial activity of the synthesized alkyl esters gallate were expressed by IC50 value, with gallic acid as an original compound and artemisin as a positive control. Compared to gallic acid, eleven synthesized compounds of alkyl esters gallate, have a greater antimalarial activity against Plasmodium falciparum. On the other hand, three compounds, that are propyl gallate, butyl gallate and trimethoxy methyl gallate, showed a lower antimalarial activity. Moreover, compared to gallic acid (IC50: 194.86 mM) and artemisin (IC50: 0.5 mM), two synthesized compounds of alkyl gallates, namely methyl gallate and hexyl gallate exhibited the stronger antimalarial activity against Plasmodium falciparum, with IC50 value of 0.03 mM and 0.11 mM, respectively. Our result clearly demonstrated that methyl gallate and hexyl gallate as a promising candidate for the new antimalarial agents.
- Arsianti, Ade,Astuty, Hendri,Fadilah,Simadibrata, Daniel Martin,Adyasa, Zoya Marie,Amartya, Daniel,Bahtiar, Anton,Tanimoto, Hiroki,Kakiuchi, Kiyomi
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p. 655 - 662
(2018/05/28)
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- Disconnecting the Estrogen Receptor Binding Properties and Antimicrobial Properties of Parabens through 3,5-Substitution
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Commercially utilized parabens are employed for their antimicrobial properties, but a weak binding to the estrogen receptor alpha (ERα) may lead to breast cancer in some applications. Modification of the paraben scaffold should allow for a disconnection of these observed properties. Toward this goal, various 3,5-substituted parabens were synthesized and assessed for antimicrobial properties against S. aureus as well as competitive binding to the ERα. The minimum inhibitory concentration assay confirmed retention of antimicrobial activity in many of these derivatives, while all compounds exhibited decreased xenoestrogen activity as determined by a combination of competitive enzyme linked immunosorbent assay (ELISA), proliferation, and estrogen receptor binding assay. Thus, these changes to the paraben scaffold have led to a multitude of paraben derivatives with antimicrobial properties up to 16 times more active than the parent paraben and that are devoid or significantly diminished of potential breast cancer causing properties.
- Bergquist, Bridget L.,Jefferson, Kaelyn G.,Kintz, Hailey N.,Barber, Amorette E.,Yeagley, Andrew A.
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supporting information
p. 51 - 55
(2018/05/04)
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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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- Synthetic compounds from an in house library as inhibitors of falcipain-2 from Plasmodium falciparum
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Falcipain-2 (FP-2) is a key cysteine protease from the malaria parasite Plasmodium falciparum. Many previous studies have identified FP-2 inhibitors; however, none has yet met the criteria for an antimalarial drug candidate. In this work, we assayed an in-house library of non-peptidic organic compounds, including (E)-chalcones, (E)-N'-benzylidene-benzohydrazides and alkyl-esters of gallic acid, and assessed the activity toward FP-2 and their mechanisms of inhibition. The (E)-chalcones 48, 54 and 66 showed the lowest IC50 values (8.5±0.8μM, 9.5±0.2μM and 4.9±1.3μM, respectively). The best inhibitor (compound 66) demonstrated non-competitive inhibition, and using mass spectrometry and fluorescence spectroscopy assays, we suggest a potential allosteric site for the interaction of this compound, located between the catalytic site and the hemoglobin binding arm in FP-2. We combined structural biology tools and mass spectrometry to characterize the inhibition mechanisms of novel compounds targeting FP-2.
- Bertoldo, Jean Borges,Chiaradia-Delatorre, Louise Domeneghini,Mascarello, Alessandra,Leal, Paulo César,Cordeiro, Marlon Norberto Sechini,Nunes, Ricardo José,Sarduy, Emir Salas,Rosenthal, Philip Jon,Terenzi, Hernán
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p. 299 - 307
(2015/04/14)
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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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- ANTAGONISTS OF THE TOLL-LIKE RECEPTOR 1/2 COMPLEX
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Provided are compounds, compositions and methods for treating Toll-like receptor 1/2 complex (TLRI/2) related inflammatory disorders. Small molecules, based on the benzotropolone scaffold, capable of influencing downstream signaling are dislcosed as well as methods of making and modifying these molecules. Also provided are methods for treating a subject for a clinical condition associated with Toll? like receptor complex 1/2 activation, comprising administering to the subject an effective amount of a benzotropolone compound.
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Page/Page column 27
(2014/02/16)
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- Discovery of small-molecule inhibitors of the TLR1/TLR2 complex
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An important regulator of innate immunity, the protein complex of Toll-like receptors 1 and 2 (TLR1/TLR2) provides an attractive target for the treatment of various immune disorders. The novel compound CU-CPT22 can compete with the binding of the specific lipoprotein ligand to TLR1/TLR2 (see picture) with high inhibitory activity and specificity. Repression of downstream signaling from TNF-α and IL-1β was also observed. Copyright
- Cheng, Kui,Wang, Xiaohui,Zhang, Shuting,Yin, Hang
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supporting information
p. 12246 - 12249
(2013/02/23)
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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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- 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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- 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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- Preparation of alkyl gallates
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C1 -C20 -alkyl gallates are prepared by reacting tannin-containing material with the corresponding alcohol R--OH and a strong acid.
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