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KMID : 0043320080310050551
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Archives of Pharmacal Research
2008 Volume.31 No. 5 p.551 ~ p.561
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A Convenient Preparation of a Disaccharide Motif and its Role in the Cytotoxicity of the Triterpenoid Saponin, α-Hederin
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Bang Seong-Cheol
Seo Hyun-Hee
Shin Hye-Rim
Lee Ki-Cheul
Hoang Le Tuan Anh
Jung Sang-Hun
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Abstract
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The sugar structures of triterpenoid saponins, such as -hederin, are intimately associated with their antitumor activities and other biological activities. The -L-rhamnopyranosyl-()--L-arabinopyranoside group of -hederin alters the cytotoxicity of its aglycon, hederagenin. This study explored the role of this saccharide unit in the cytotoxic effect of -hederin and the possibility of its use as a carrier moiety in prodrugs of anticancer agents. A new convenient and practical procedure for the preparation of 4-methoxybenzoyl-2,3,4-tri-O-benzoyl--L-rhamnopyranosyl-()-3,4-O-dibenzoyl--L-arabinopyranoside (2) from 4-methoxybenzoyl--Larabinopyranoside was accomplished using four steps with an overall yield of 63%. The use of as a catalyst in the glycosylation step in this procedure had a large advantage over the TMSOTf catalyst used in the usual method. Moreover, the key intermediate obtained in this procedure, 4-methoxybenzoyl-2,3,4-tri-O-benzoyl--L-rhamnopyranosyl-()--L-arabinopyranoside (7), was selectively transformed to 4-methoxybenzoyl-2,3,4-tri-O-benzoyl--L-rhamnopyranosyl-()-4-O-acetyl--L-arabinopyranoside (9) and 4-methoxybenzoyl-2,3,4-tri-Obenzoyl--L-rhamnopyranosyl-()-3-O-benzoyl--L-arabinopyranoside (10). These derivatives did not show any cytotoxicity against human cancer cell lines. Thus the 3-O--L-rhamnopyranosyl-()--L-arabinopyranoside could be used as a nontoxic carrier moiety to enhance the activity of anticancer drugs.
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KEYWORD
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Triterpenoid saponins, Disaccharide moiety-Hederin
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