Biological and Pharmaceutical Bulletin
Online ISSN : 1347-5215
Print ISSN : 0918-6158
ISSN-L : 0918-6158
Anti-herpes Virus Type 1 Activity of Oleanane-Type Triterpenoids
Tsuyoshi IkedaKazumi YokomizoMasafumi OkawaRyota TsuchihashiJunei KinjoToshihiro NoharaMasaru Uyeda
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2005 Volume 28 Issue 9 Pages 1779-1781


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.

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© 2005 The Pharmaceutical Society of Japan
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