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OtherCHEMOTHERAPY/GENE THERAPY

Purification and Characterization of Eugeniin as an Anti-herpesvirus Compound from Geum japonicum andSyzygium aromaticum

Masahiko Kurokawa, Toyoharu Hozumi, Purusotam Basnet, Michio Nakano, Shigetoshi Kadota, Tuneo Namba, Takashi Kawana and Kimiyasu Shiraki
Journal of Pharmacology and Experimental Therapeutics February 1998, 284 (2) 728-735;
Masahiko Kurokawa
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Toyoharu Hozumi
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Purusotam Basnet
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Michio Nakano
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Shigetoshi Kadota
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Tuneo Namba
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Takashi Kawana
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Kimiyasu Shiraki
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Abstract

The hot-water extract of Geum japonicum has been shown to exhibit prophylactic and therapeutic anti-herpes simplex virus (HSV) activity in murine infection models. Eugeniin was purified as an anti-HSV compound from the extract and also was isolated from another herbal extract (Syzygium aromaticum) that had exhibited anti-HSV activity in mice. Thus the anti-HSV action of eugeniin was characterized. The effective concentration (5.0 μg/ml) for 50% plaque reduction of eugeniin for wild HSV type 1 (HSV-1) on Vero cells was 13.9-fold lower than its 50% cytotoxic concentration determined by a yield-reduction assay. Eugeniin also inhibited the growth of acyclovir-phosphonoacetic acid-resistant HSV-1, thymidine kinase-deficient HSV-1 and wild HSV type 2. Eugeniin as well as phosphonoacetic acid inhibited viral DNA and late viral protein syntheses in their infected Vero cells, but not cellular protein synthesis at its inhibitory concentrations. Purified HSV-1 DNA polymerase activity was inhibited by eugeniin noncompetitively with respect to dTTP. Its apparent Ki value for euginiin was 8.2- and 5.8-fold lower than theKi values of purified human DNA polymerases α and β, respectively. Thus one of the major target sites of inhibitory action of eugeniin is viral DNA synthesis; the inhibitory action for viral DNA polymerase activity was novel compared with anti-HSV nucleoside analogs.

Footnotes

  • Send reprint requests to: Dr. Kimiyasu Shiraki, Department of Virology, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930–01, Japan.

  • Abbreviations:
    ACV
    acyclovir
    APr
    acyclovir-phosphonoacetic acid-resistant
    Ara-A
    9-β-d-arabinofuranosyladenine
    BSA
    bovine serum albumin
    CC50
    50% cytotoxic concentration
    DMSO
    dimethyl sulfoxide
    DTT
    dithiothreitol
    EC50
    effective concentrations for 50% plaque reduction
    EtOAc
    ethylacetate
    G. japonicum
    Geum japonicum Thunb
    HEL
    human embryonic lung
    HIV-1
    human immunodeficiency virus type 1
    HPLC
    high-performance liquid chromatography
    HSV
    herpes simplex virus
    HSV-1
    herpes simplex virus type 1
    HSV-2
    herpes simplex virus type 2
    MEM
    Eagle’s minimum essential medium
    PAA
    phosphonoacetic acid
    PFU
    plaque-forming units
    S. aromaticum
    Syzygium aromaticum (L.) MERR. et PERRY
    SDS
    sodium dodecyl sulfate
    TK−
    thymidine kinase-deficient
    UV
    ultraviolet
    • Received April 7, 1997.
    • Accepted October 3, 1997.
  • The American Society for Pharmacology and Experimental Therapeutics
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Journal of Pharmacology and Experimental Therapeutics
Vol. 284, Issue 2
1 Feb 1998
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OtherCHEMOTHERAPY/GENE THERAPY

Purification and Characterization of Eugeniin as an Anti-herpesvirus Compound from Geum japonicum andSyzygium aromaticum

Masahiko Kurokawa, Toyoharu Hozumi, Purusotam Basnet, Michio Nakano, Shigetoshi Kadota, Tuneo Namba, Takashi Kawana and Kimiyasu Shiraki
Journal of Pharmacology and Experimental Therapeutics February 1, 1998, 284 (2) 728-735;

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OtherCHEMOTHERAPY/GENE THERAPY

Purification and Characterization of Eugeniin as an Anti-herpesvirus Compound from Geum japonicum andSyzygium aromaticum

Masahiko Kurokawa, Toyoharu Hozumi, Purusotam Basnet, Michio Nakano, Shigetoshi Kadota, Tuneo Namba, Takashi Kawana and Kimiyasu Shiraki
Journal of Pharmacology and Experimental Therapeutics February 1, 1998, 284 (2) 728-735;
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