Biological evaluation of anti-influenza viral activity of semi-synthetic catechin derivatives

Jae Min Song, Ki Duk Park, Kwang Hee Lee, Young Ho Byun, Ju Hee Park, Sung Han Kim, Jae Hong Kim, Baik Lin Seong

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

Catechin derivatives with different alkyl chain length and aromatic ring substitutions at the 3-hydroxyl group were synthesized from epigallocatechin (EGC) and (+)-catechin (C) and their anti-influenza viral activity were evaluated in vitro and in ovo. Pronounced antiviral activity was observed for derivatives carrying moderate chain length (7-9 carbons) as compared to those with aromatic rings, whereas the 5′-hydroxyl group of the trihydroxy benzyl moiety did not significantly contribute to antiviral activity. The derivatives exerted inhibitory effects for all six influenza subtypes tested including three major types of currently circulating human influenza viruses (A/H1N1, A/H3N2 and B type), H2N2 and H9N2 avian influenza virus. The compounds strongly inhibited adsorption of the viruses on red blood cell (RBC). They also restricted the growth of avian influenza virus in ovo with minimum inhibition concentration (MIC) of 5-10 μM far exceeding the neuraminidase (NA) inhibitor oseltamivir or M2 proton channel inhibitor amantadine. The antiviral activity appears to be mediated by interaction with hemagglutinin (HA)/viral membrane rendering HA less fusogenic at the initial stage of infection. The broad spectrum activity against various subtypes of influenza viruses may complement the limitations of current antivirals and contribute for managing potentially emerging influenza pandemic. The structure-activity data of catechin derivatives may usefully guideline future research endeavors for applying green tea catechins as alternative anti-viral agents.

Original languageEnglish
Pages (from-to)178-185
Number of pages8
JournalAntiviral Research
Volume76
Issue number2
DOIs
Publication statusPublished - 2007 Nov 1

Fingerprint

Catechin
Orthomyxoviridae
Human Influenza
Antiviral Agents
Influenza in Birds
Hydroxyl Radical
Viral Hemagglutinins
Oseltamivir
Amantadine
Hemagglutinins
Neuraminidase
Pandemics
Tea
Adsorption
Protons
Carbon
Erythrocytes
Guidelines
Viruses
Membranes

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Virology

Cite this

Song, Jae Min ; Park, Ki Duk ; Lee, Kwang Hee ; Byun, Young Ho ; Park, Ju Hee ; Kim, Sung Han ; Kim, Jae Hong ; Seong, Baik Lin. / Biological evaluation of anti-influenza viral activity of semi-synthetic catechin derivatives. In: Antiviral Research. 2007 ; Vol. 76, No. 2. pp. 178-185.
@article{721ac3aca3c24c5c89946873f954aa2c,
title = "Biological evaluation of anti-influenza viral activity of semi-synthetic catechin derivatives",
abstract = "Catechin derivatives with different alkyl chain length and aromatic ring substitutions at the 3-hydroxyl group were synthesized from epigallocatechin (EGC) and (+)-catechin (C) and their anti-influenza viral activity were evaluated in vitro and in ovo. Pronounced antiviral activity was observed for derivatives carrying moderate chain length (7-9 carbons) as compared to those with aromatic rings, whereas the 5′-hydroxyl group of the trihydroxy benzyl moiety did not significantly contribute to antiviral activity. The derivatives exerted inhibitory effects for all six influenza subtypes tested including three major types of currently circulating human influenza viruses (A/H1N1, A/H3N2 and B type), H2N2 and H9N2 avian influenza virus. The compounds strongly inhibited adsorption of the viruses on red blood cell (RBC). They also restricted the growth of avian influenza virus in ovo with minimum inhibition concentration (MIC) of 5-10 μM far exceeding the neuraminidase (NA) inhibitor oseltamivir or M2 proton channel inhibitor amantadine. The antiviral activity appears to be mediated by interaction with hemagglutinin (HA)/viral membrane rendering HA less fusogenic at the initial stage of infection. The broad spectrum activity against various subtypes of influenza viruses may complement the limitations of current antivirals and contribute for managing potentially emerging influenza pandemic. The structure-activity data of catechin derivatives may usefully guideline future research endeavors for applying green tea catechins as alternative anti-viral agents.",
author = "Song, {Jae Min} and Park, {Ki Duk} and Lee, {Kwang Hee} and Byun, {Young Ho} and Park, {Ju Hee} and Kim, {Sung Han} and Kim, {Jae Hong} and Seong, {Baik Lin}",
year = "2007",
month = "11",
day = "1",
doi = "10.1016/j.antiviral.2007.07.001",
language = "English",
volume = "76",
pages = "178--185",
journal = "Antiviral Research",
issn = "0166-3542",
publisher = "Elsevier",
number = "2",

}

Biological evaluation of anti-influenza viral activity of semi-synthetic catechin derivatives. / Song, Jae Min; Park, Ki Duk; Lee, Kwang Hee; Byun, Young Ho; Park, Ju Hee; Kim, Sung Han; Kim, Jae Hong; Seong, Baik Lin.

In: Antiviral Research, Vol. 76, No. 2, 01.11.2007, p. 178-185.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Biological evaluation of anti-influenza viral activity of semi-synthetic catechin derivatives

AU - Song, Jae Min

AU - Park, Ki Duk

AU - Lee, Kwang Hee

AU - Byun, Young Ho

AU - Park, Ju Hee

AU - Kim, Sung Han

AU - Kim, Jae Hong

AU - Seong, Baik Lin

PY - 2007/11/1

Y1 - 2007/11/1

N2 - Catechin derivatives with different alkyl chain length and aromatic ring substitutions at the 3-hydroxyl group were synthesized from epigallocatechin (EGC) and (+)-catechin (C) and their anti-influenza viral activity were evaluated in vitro and in ovo. Pronounced antiviral activity was observed for derivatives carrying moderate chain length (7-9 carbons) as compared to those with aromatic rings, whereas the 5′-hydroxyl group of the trihydroxy benzyl moiety did not significantly contribute to antiviral activity. The derivatives exerted inhibitory effects for all six influenza subtypes tested including three major types of currently circulating human influenza viruses (A/H1N1, A/H3N2 and B type), H2N2 and H9N2 avian influenza virus. The compounds strongly inhibited adsorption of the viruses on red blood cell (RBC). They also restricted the growth of avian influenza virus in ovo with minimum inhibition concentration (MIC) of 5-10 μM far exceeding the neuraminidase (NA) inhibitor oseltamivir or M2 proton channel inhibitor amantadine. The antiviral activity appears to be mediated by interaction with hemagglutinin (HA)/viral membrane rendering HA less fusogenic at the initial stage of infection. The broad spectrum activity against various subtypes of influenza viruses may complement the limitations of current antivirals and contribute for managing potentially emerging influenza pandemic. The structure-activity data of catechin derivatives may usefully guideline future research endeavors for applying green tea catechins as alternative anti-viral agents.

AB - Catechin derivatives with different alkyl chain length and aromatic ring substitutions at the 3-hydroxyl group were synthesized from epigallocatechin (EGC) and (+)-catechin (C) and their anti-influenza viral activity were evaluated in vitro and in ovo. Pronounced antiviral activity was observed for derivatives carrying moderate chain length (7-9 carbons) as compared to those with aromatic rings, whereas the 5′-hydroxyl group of the trihydroxy benzyl moiety did not significantly contribute to antiviral activity. The derivatives exerted inhibitory effects for all six influenza subtypes tested including three major types of currently circulating human influenza viruses (A/H1N1, A/H3N2 and B type), H2N2 and H9N2 avian influenza virus. The compounds strongly inhibited adsorption of the viruses on red blood cell (RBC). They also restricted the growth of avian influenza virus in ovo with minimum inhibition concentration (MIC) of 5-10 μM far exceeding the neuraminidase (NA) inhibitor oseltamivir or M2 proton channel inhibitor amantadine. The antiviral activity appears to be mediated by interaction with hemagglutinin (HA)/viral membrane rendering HA less fusogenic at the initial stage of infection. The broad spectrum activity against various subtypes of influenza viruses may complement the limitations of current antivirals and contribute for managing potentially emerging influenza pandemic. The structure-activity data of catechin derivatives may usefully guideline future research endeavors for applying green tea catechins as alternative anti-viral agents.

UR - http://www.scopus.com/inward/record.url?scp=34548716936&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34548716936&partnerID=8YFLogxK

U2 - 10.1016/j.antiviral.2007.07.001

DO - 10.1016/j.antiviral.2007.07.001

M3 - Article

C2 - 17709148

AN - SCOPUS:34548716936

VL - 76

SP - 178

EP - 185

JO - Antiviral Research

JF - Antiviral Research

SN - 0166-3542

IS - 2

ER -