Abstract

Epigallocatechin-3-O-gallate (EGCG) is the major catechin component of green tea (Cameria sinensis), and is known to possess antiviral activities against a wide range of DNA viruses and RNA viruses. However, few studies have examined chemical modifications of EGCG in terms of enhanced antiviral efficacy. This paper discusses which steps of virus infection EGCG interferes with, citing previous reports. EGCG appears most likely to inhibits the early stage of infections, such as attachment, entry, and membrane fusion, by interfering with viral membrane proteins. According to the relationships between structure and antiviral activity of catechin derivatives, the 3-galloyl and 5′-OH group of catechin derivatives appear critical to antiviral activities. Enhancing the binding affinity of EGCG to virus particles would thus be important to increase virucidal activity. We propose a newly developed EGCG-fatty acid derivative in which the fatty acid on the phenolic hydroxyl group would be expected to increase viral and cellular membrane permeability. EGCG-fatty acid monoesters showed improved antiviral activities against different types of viruses, probably due to their increased affinity for virus and cellular membranes. Our study promotes the application of EGCG-fatty acid derivatives for the prevention and treatment of viral infections.

Highlights

  • Catechins in Green Tea Extracts and Their Antiviral ActivitiesA series of catechin derivatives are present in green tea extract, representing 30–42% of the total dry weight of tea leaves [1]

  • We summarize previous research reports regarding the antiviral activity of EGCG and its derivatives in terms of their structures and virus inhibitory mechanisms

  • We introduce in relationships between structure and anti-viral activity for catechin derivatives

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Summary

Introduction

A series of catechin derivatives are present in green tea extract, representing 30–42% of the total dry weight of tea leaves [1]. The assembly and virion incorporation of the eight distinct viral ribonucleoproteins requires segment-specific packaging signals in the viral RNAs. HIV-1 belongs to the Retroviridae family and is an enveloped, roughly spherical virus with a diameter of about 120 nm and two copies of a positive-sense single-stranded RNA genome. In case of HCV and IAV, as the pH in the endosome drops, a conformational change in viral membrane proteins is triggered and induces membrane fusion between virus and cells. This membrane fusion step is described as “Step C” in this study. This step is described as “Step E” in this study

Antiviral Activity of Catechins on Enveloped DNA Viruses
Antiviral Mechanism of Action of EGCG on HIV-1
Antiviral Mechanism of EGCG on Influenza Virus
Structure and Antiviral Activity of Catechin Derivatives
Lipid Bilayer Affinity of EGCG-Alkyl Ether Derivatives
Synthesis of EGCG-Fatty Acid Derivatives
Anti-Influenza Virus Activity of EGCG-C16 in Chicken Embryonated Eggs
Antiviral Activity of EGCG-Fatty Acid Derivatives for Other Viruses
Findings
Conclusions
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