Enhanced anti-influenza A virus activity of (−)-epigallocatechin-3-O-gallate fatty acid monoester derivatives: Effect of alkyl chain length

Mori, Shuichi; Miyake, S.; Kobe, Takayoshi; Nakaya, Takaaki; Fuller, Stephen D.; Kato, Nobuo; Kaihatsu, Kunihiro

doi:10.1016/j.bmcl.2008.02.020

Cited by 85 publications

(80 citation statements)

References 16 publications

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“…Gargling with tea catechin extracts prevented influenza virus infection in elderly nursing home residents [91]. Long chain monoester derivatives of EGCG enhanced the anti-influenza virus activity 24-fold relative to native EGCG [92]. The influenza A RNA polymerase possesses endonuclease activity to digest the host mRNA.…”

Section: Catechinsmentioning

confidence: 99%

Antioxidant Therapy as a Potential Approach to Severe Influenza-Associated Complications

2011

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Section: Catechinsmentioning

confidence: 99%

Antioxidant Therapy as a Potential Approach to Severe Influenza-Associated Complications

2011

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“…They found that the effectiveness of EGCG-fatty acid monoesters against influenza A/Puerto Rico/8/33 (H1N1) virus was increased in an alkyl chain length-dependent manner in Madin-Darby canine kidney (MDCK) cells [15]. Among EGCG-saturated fatty acid monoesters, EGCG-monopalmitate (EGCG-C 16 ) (Figure 1b) showed the highest anti-influenza virus activity [15]. Although EGCG-C 16 exhibited a slightly (3.2-fold) higher cytotoxic effect to MDCK cells, it showed significantly (23.5-fold) higher anti-influenza virus activity against the A/Puerto Rico/8/34(H1N1) strain [16].…”

mentioning

confidence: 99%

“…They found that EGCG modified with a C 18 alkyl group possesses increased hydrophobicity and lipid membrane affinity relative to natural EGCG. Mori et al developed a method to introduce fatty acids into the B-ring or D-ring of EGCG using lipase-catalyzed transesterification [15]. They found that the effectiveness of EGCG-fatty acid monoesters against influenza A/Puerto Rico/8/33 (H1N1) virus was increased in an alkyl chain length-dependent manner in Madin-Darby canine kidney (MDCK) cells [15].…”

mentioning

confidence: 99%

“…showed the highest anti-influenza virus activity [15]. Although EGCG-C 16 exhibited a slightly (3.2-fold) higher cytotoxic effect to MDCK cells, it showed significantly (23.5-fold) higher anti-influenza virus activity against the A/Puerto Rico/8/34(H1N1) strain [16].…”

mentioning

confidence: 99%

“…Mori et al developed a method to introduce fatty acids into the B-ring or D-ring of EGCG using lipase-catalyzed transesterification [15]. They found that the effectiveness of EGCG-fatty acid monoesters against influenza A/Puerto Rico/8/33 (H1N1) virus was increased in an alkyl chain length-dependent manner in Madin-Darby canine kidney (MDCK) cells [15]. Among EGCG-saturated fatty acid monoesters, EGCG-monopalmitate (EGCG-C 16 ) (Figure 1b) showed the highest anti-influenza virus activity [15].…”

mentioning

confidence: 99%

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Potential Applications of Epigallocatechin Gallate-Fatty Acid Derivatives as Antiviral Agents

Kaihatsu¹

2015

J Antivir Antiretrovir

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(Figure 1b) showed the highest anti-influenza virus activity [15]. Although EGCG-C 16 exhibited a slightly (3.2-fold) higher cytotoxic effect to MDCK cells, it showed significantly (23.5-fold) higher anti-influenza virus activity against the A/Puerto Rico/8/34(H1N1) strain [16]. EGCG-C 16 inhibited human-, swine-and avian-pathogenic influenza A viruses, and the EC 50 was between 10 nM and 61 nM, a 7.1-fold to 44-fold lower concentration than unmodified EGCG [16]. A lethal dose of avian-influenza A/H5N2 virus pretreated with EGCG-C 16 completely prevented the death of embryonated chicken eggs inoculated with the virus by an allantoic cavity route [16].Oliveira et al. reported that EGCG-C 16 inhibited the adsorption step of herpes simplex virus infection in Vero cells [17]. Zhao et al. reported that EGCG-C 16 exhibits significantly higher antiviral activity against porcine reproductive and respiratory syndrome virus than natural EGCG and ribavirin as both pre-treatment and post-treatment [18]. These reports suggest that the pronounced antiviral activities of EGCG-fatty acid derivatives were due to increased permeability through both the viral membrane and the cell membrane.Although EGCG interferes with different types of viral infections, it is easily oxidized or hydrolyzed under physiological conditions because of the reactive hydroxyl groups in the gallyl moiety in the B-ring and the galloyl moiety in the D-ring [19,20]. However, addition of a palmitoyl group to the B-ring or D-ring prolonged its half-life in a cell culture medium approximately seven-fold [21].These improved chemical, biological, and antiviral activities of

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Synthesis of Epigallocatechin Gallate, Nobiletin, and Their Derivatives for Chemical‐Biological Studies

Asakawa

Inai

Kobayashi

2023

Recent Advances in Polyphenol Research

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Enhanced anti-influenza A virus activity of (−)-epigallocatechin-3-O-gallate fatty acid monoester derivatives: Effect of alkyl chain length

Cited by 85 publications

References 16 publications

Antioxidant Therapy as a Potential Approach to Severe Influenza-Associated Complications

Antioxidant Therapy as a Potential Approach to Severe Influenza-Associated Complications

Potential Applications of Epigallocatechin Gallate-Fatty Acid Derivatives as Antiviral Agents

Synthesis of Epigallocatechin Gallate, Nobiletin, and Their Derivatives for Chemical‐Biological Studies

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