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Review
. 2018 Sep 27;23(10):2475.
doi: 10.3390/molecules23102475.

Antiviral Mechanism of Action of Epigallocatechin-3- O-gallate and Its Fatty Acid Esters

Kunihiro Kaihatsu  1 , Miyuki Yamabe  2 , Yasuhito Ebara  3
Affiliations
Review

Antiviral Mechanism of Action of Epigallocatechin-3- O-gallate and Its Fatty Acid Esters

Kunihiro Kaihatsu et al. Molecules. .

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.

Keywords: attachment; budding; catechin; entry; epigallocatechin-3-O-gallate; fatty acid derivative; fusion; replication; virus inhibition.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of natural catechins. (−)-epigallocatechin-3-O-gallate (EGCG; 1), (+)-gallocatechin-3-O-gallate ((+)-GCG; 2), (-)-gallocatechin-3-O-gallate ((−)-GCG; 3), 5,7-dideoxy-EGCG (DO-EGCG; 4), epigallocatechin 3,5-digallate (EGCDG; 5), EGCG-thioether derivatives (6), EGCG-n-octadecylisocyanate derivative (7), EGCG-fatty acid monoester derivatives (8), EGCG-fatty acid tetra, octaester derivatives (9), (−)-epicatechin-3-O-gallate (ECG; 10), (−)-catechin-3-O-gallate (CG; 11), (−)-epigallocatechin (EGC; 12), (−)-gallocatechin (GC; 13), delphinidin (14), (−)-epicatechin (EC; 15), (−)-catechin (C; 16), 2′,2′-bisepigallocatechin digallate (bEGCdG; 17), rhodisin (18), theasinensin A (19), P2 (20), epicatechin-3-O-gallate-(4β→8)-epicatechin-3-O-gallate (21), procyanidin B2 (22), theaflavin (TF; 23) theaflavin-3-gallate (TF-3-G; 24), theaflavin-3′-gallate (TF-3′-G; 25), and theaflavin-3,3′-O-digallate (TFDG; 26).
Figure 1
Figure 1
Chemical structures of natural catechins. (−)-epigallocatechin-3-O-gallate (EGCG; 1), (+)-gallocatechin-3-O-gallate ((+)-GCG; 2), (-)-gallocatechin-3-O-gallate ((−)-GCG; 3), 5,7-dideoxy-EGCG (DO-EGCG; 4), epigallocatechin 3,5-digallate (EGCDG; 5), EGCG-thioether derivatives (6), EGCG-n-octadecylisocyanate derivative (7), EGCG-fatty acid monoester derivatives (8), EGCG-fatty acid tetra, octaester derivatives (9), (−)-epicatechin-3-O-gallate (ECG; 10), (−)-catechin-3-O-gallate (CG; 11), (−)-epigallocatechin (EGC; 12), (−)-gallocatechin (GC; 13), delphinidin (14), (−)-epicatechin (EC; 15), (−)-catechin (C; 16), 2′,2′-bisepigallocatechin digallate (bEGCdG; 17), rhodisin (18), theasinensin A (19), P2 (20), epicatechin-3-O-gallate-(4β→8)-epicatechin-3-O-gallate (21), procyanidin B2 (22), theaflavin (TF; 23) theaflavin-3-gallate (TF-3-G; 24), theaflavin-3′-gallate (TF-3′-G; 25), and theaflavin-3,3′-O-digallate (TFDG; 26).
Figure 2
Figure 2
The DNA and RNA viruses described in this study were classified by Baltimore group. A representative of each virus family and their structures are summarized in the figures. (A) Herpes simplex virus-1 is a member of Herpesviridae, classified to Baltimore group I possessing dsDNA as the genome in a nucleocapsid core enveloped by lipid membrane. (B) Hepatitis C virus and (C) Dengue virus are member of Flaviviridae, classified to Baltimore group IV possessing a (+) single-stranded RNA genome in the viral particle. (D) Influenza A virus is a member of Orthomyxoviridae, classified to Baltimore group V possessing eight (−)-strand viral RNA genomes in the viral particle. (E) Human immunodeficiency virus-1 is a member of Retroviridae, classified to Baltimore VI possessing two (+)-strand RNA genomes in a protein core in the viral particle.
Figure 3
Figure 3
Schematic overviews of the virus life cycles of (1) HSV, (2) HCV, (3) IAV, and (4) HIV-1 in infected cells. Their infection processes were divided by five steps. Step A: virus attaches to cell surface receptor. Step B: virus entry into cells by endocytosis. Step C: virus-cell membrane fusion. Step D: viral genome replication and synthesis of progeny viral components. Step E: budding of newly developed progeny virions.
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