Antiviral effect of octyl gallate against DNA and RNA viruses

Uozaki, Misao; Yamasaki, Hisashi; Katsuyama, Yukiko; Higuchi, Masanori; Higuti, Tomihiko; Koyama, A. Hajime

doi:10.1016/j.antiviral.2006.07.010

Cited by 77 publications

(71 citation statements)

References 20 publications

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“…In our study, the cytotoxicity presented a similar profile, although the antiviral activity was found only for the gallates with as much as seven carbons in the alkyl moiety. The discrepancies between the results of these studies may come from the different employed cell lines and used methodologies, as already supposed by the authors, 20) fact that corroborates the need for a standardization in this research area.…”

Section: Discussionsupporting

confidence: 59%

“…During the course of our studies, another study 20) described the anti-HSV-1 activity of octyl gallate with a moderate cytotoxicity. In our study, the cytotoxicity presented a similar profile, although the antiviral activity was found only for the gallates with as much as seven carbons in the alkyl moiety.…”

Section: Discussionmentioning

confidence: 99%

“…The direct virucidal activity was also found in other gallate derivatives, such as epigallocatechin-3-gallate, prodelphinidin B-2 3Ј-O-gallate and octyl gallate. 20,21,[30][31][32] Given that virucidal activity of some compounds was decreased in the presence of human cervical secretions or protein-rich solutions, 33,34) the virucidal activity of GA and PG in the presence of BSA and FCS solutions was investigated. The BSA solution (5%) but not FCS neutralized to some extent the anti-HSV-2 activity of GA.…”

Section: Discussionmentioning

confidence: 99%

“…20,21) In the present study, the anti-HSV-2 activity of gallic acid and pentyl gallate was evaluated followed by the determination of the site of antiviral activity of these compounds.…”

Section: )mentioning

confidence: 99%

“…19) Furthermore, the pronounced anti-HSV-1 activity of octyl gallate, and its inhibitory effect against RNA viruses were also recently described. 20,21) In the present study, the anti-HSV-2 activity of gallic acid and pentyl gallate was evaluated followed by the determination of the site of antiviral activity of these compounds.…”

mentioning

confidence: 99%

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Evaluation of Anti-HSV-2 Activity of Gallic Acid and Pentyl Gallate

Kratz

Andrighetti-Fröhner

Leal

et al. 2008

Biological & Pharmaceutical Bulletin

128

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Herpes simplex virus (HSV) is a DNA-containing enveloped virus that causes common viral infections in humans worldwide leading to a variety of diseases. HSV-1 and HSV-2 can be distinguished on the basis of clinical manifestations (the former is more frequently associated with oral cold sores, while the later causes genital ulcers) and biochemical and serological examinations. In most cases, HSV infection is usually benign or asymptomatic in immunocompetent individuals; however, in patients with an immature or compromised immune system, the infection can be serious and sometimes life-threatening. 1,2) Several nucleoside analogues have been approved for clinical use. Among those, acyclovir is widely used for the systemic treatment of HSV infections. It is a highly selective antiviral agent because it is specifically phosphorylated by viral thymidine kinase in infected cells. However, acyclovir-resistant HSV infection in immunocompromised patients such as transplanted patients and patients with AIDS has recently been observed. Therefore, it is desirable to develop new anti-HSV agents in order to substitute or complement the antiviral drugs available. 3,4)The synthetic n-alkyl esters of gallic acid (GA), also known as gallates, especially propyl, octyl and dodecyl gallates, are widely employed as antioxidants by food and pharmaceutical industries. 5,6) Besides the antioxidant activity, other biological activities have been described for this group of molecules, mainly anticancer, 7-10) antibacterial and antifungal properties. [11][12][13][14][15][16] There are few reports about the antiviral activity of these compounds. In 1988, the potent inhibition of HSV-1 and HSV-2 by methyl gallate was described. 17) In 2000, as part of the screening of phenolic compounds against HIV-1 integrase, gallic acid was found to be active. 18)More recently, the anti-HSV activity of several gallates was described by our research group, which proposed various structure-activity relationships regarding the antiviral, antioxidant and genotoxic effects.19) Furthermore, the pronounced anti-HSV-1 activity of octyl gallate, and its inhibitory effect against RNA viruses were also recently described. 20,21) In the present study, the anti-HSV-2 activity of gallic acid and pentyl gallate was evaluated followed by the determination of the site of antiviral activity of these compounds. MATERIALS AND METHODSCompounds GA and pentyl gallate (PG) (Fig. 1) were synthesized as previously described.19) The compounds (50 mM) were dissolved in dimethyl sulfoxide, stored at Ϫ20°C protected from light, and further diluted in culture medium prior to use.Cells and Virus African green monkey kidney cells (GMK AH1) were grown in Eagle's minimum essential medium (EMEM, Gibco BRL, Grand Island, NY, U.S.A.) supplemented with 2% fetal calf serum (FSC), 0.05% primaton substance (Kraft Inc., Norwich, CT, U.S.A.), 100 U/ml Göteborg, Sweden. Received November 23, 2007; accepted February 5, 2008; published online February 20, 2008 The synthetic n-alkyl esters of galli...

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Section: Discussionsupporting

confidence: 59%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

“…20,21) In the present study, the anti-HSV-2 activity of gallic acid and pentyl gallate was evaluated followed by the determination of the site of antiviral activity of these compounds.…”

Section: )mentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

Evaluation of Anti-HSV-2 Activity of Gallic Acid and Pentyl Gallate

Kratz

Andrighetti-Fröhner

Leal

et al. 2008

Biological & Pharmaceutical Bulletin

128

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Gallic acid‐based alkyl esters synthesis in a water‐free system by celite‐bound lipase of Bacillus licheniformisSCD11501

Sharma

Kanwar

Dogra

et al. 2015

Biotechnology Progress

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Gallic acid (3, 4, 5- trihydroxybenzoic acid) is an important antioxidant, anti-inflammatory, and radical scavenging agent. In the present study, a purified thermo-tolerant extra-cellular lipase of Bacillus licheniformis SCD11501 was successfully immobilized by adsorption on Celite 545 gel matrix followed by treatment with a cross-linking agent, glutaraldehyde. The celite-bound lipase treated with glutaraldehyde showed 94.8% binding/retention of enzyme activity (36 U/g; specific activity 16.8 U/g matrix; relative increase in enzyme activity 64.7%) while untreated matrix resulted in 88.1% binding/retention (28.0 U/g matrix; specific activity 8.5 U/g matrix) of lipase. The celite-bound lipase was successfully used to synthesis methyl gallate (58.2%), ethyl gallate (66.9%), n-propyl gallate (72.1%), and n-butyl gallate (63.8%) at 55(o) C in 10 h under shaking (150 g) in a water-free system by sequentially optimizing various reaction parameters. The low conversion of more polar alcohols such as methanol and ethanol into their respective gallate esters might be due to the ability of these alcohols to severely remove water from the protein hydration shell, leading to enzyme inactivation. Molecular sieves added to the reaction mixture resulted in enhanced yield of the alkyl ester(s). The characterization of synthesised esters was done through fourier transform infrared (FTIR) spectroscopy and (1) H NMR spectrum analysis.

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Anti‐inflammatory effect of octyl gallate in alveolar macrophages cells and mice with acute lung injury

Haute

Luft

Antunes

et al. 2020

Journal Cellular Physiology

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Acute lung injury (ALI) is an inflammatory process, and has high incidence and mortality. ALI and the acute respiratory distress syndrome are two common complications worldwide that result in acute lung failure, sepsis, and death. Pro-inflammatory substances, such as cytokines and chemokines, are responsible for activating the body's defense mechanisms and usually mediate inflammatory processes. Therefore, the research of substances that decrease the uncontrolled response of organism is seen as potential for patients with ALI. Octyl gallate (OG) is a phenolic compound with therapeutic actions namely antimicrobial, antiviral, and antifungal. In this study, we evaluated its action on lipopolysaccharide (LPS)-activated alveolar macrophages RAW 264.7 cells and ALI in male mice. Our results demonstrated protective effects of OG in alveolar macrophages activated with LPS and mice with ALI. The OG treatment significantly decreased the inflammatory markers in both studies in vitro and in vivo. The data suggested that OG can act as an anti-inflammatory agent for ALI.

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Antiviral effect of octyl gallate against DNA and RNA viruses

Cited by 77 publications

References 20 publications

Evaluation of Anti-HSV-2 Activity of Gallic Acid and Pentyl Gallate

Evaluation of Anti-HSV-2 Activity of Gallic Acid and Pentyl Gallate

Gallic acid‐based alkyl esters synthesis in a water‐free system by celite‐bound lipase of Bacillus licheniformisSCD11501

Anti‐inflammatory effect of octyl gallate in alveolar macrophages cells and mice with acute lung injury

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