Anti-herpes virus type 1 activity of oleanane-type triterpenoids.
The anti-herpes simplex virus type 1 (HSV-1) activity of 15 oleanan-type triterpenoides including glycyrrhizin and its sapogenol was examined and their structure-activity relationships were discussed. Although glycyrrhizin which exhibited in vivo efficacy against HSV-1 replication showed moderate in vitro anti-HSV-1 activity, its sapogenol, glycyrrhetic acid, showed 10 times greater action than glycyrrhizin. Therefore, the in vivo anti-HSV-1 activity of glycyrrhizin administered orally could be reasonably attributed to glycyrrhetic acid generated by hydrolysis by intestinal bacteria. Since the activity of soyasapogenol A was less than 1/20 of that of soyasapogenol B, the hydroxylation at C-21 seemed to reduce anti-HSV-1 activity. Since kudzusapogenol A, abrisapogenols B and C lacked the activity, the C-29 hydroxy group would eliminate anti-HSV-1 activity. On the other hand, since the methylesters of kudzusapogenol B and glycyrrhetic acid exhibited greater action, a methoxy carboxy group at C-20 might enhance activity.
Ikeda
Tsuyoshi
T
Laboratory of Natural Medicines, Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan.
Yokomizo
Kazumi
K
Okawa
Masafumi
M
Tsuchihashi
Ryota
R
Kinjo
Junei
J
Nohara
Toshihiro
T
Uyeda
Masaru
M
D000818:Animals; D000998:Antiviral Agents / Q000494:pharmacology*; D002240:Carbohydrate Sequence; D002522:Chlorocebus aethiops; D006034:Glycyrrhetinic Acid / Q000494:pharmacology; D019695:Glycyrrhizic Acid / Q000494:pharmacology; D018259:Herpesvirus 1, Human / Q000187:drug effects*; D006801:Humans; D008969:Molecular Sequence Data; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000494:pharmacology*; D014709:Vero Cells; D010948:Viral Plaque Assay
D000998:Antiviral Agents; D014315:Triterpenes; C413246:oleanane; D019695:Glycyrrhizic Acid; D009828:Oleanolic Acid; D006034:Glycyrrhetinic Acid