A Convenient Preparation of a Disaccharide Motif and its Role in the Cytotoxicity of the Triterpenoid Saponin, $alpha$-Hederin

Bang, Seong-Cheol; Seo, Hyun-Hee; Shin, Hye-Rim; Lee, Ki-Cheul; Hoang, Le Tuan Anh; Jung, Sang-Hun

추천

검색

자료유형: 학술저널

저자정보: Bang, Seong-Cheol (College of Pharmacy, Chungnam National University) Seo, Hyun-Hee (College of Pharmacy, Chungnam National University) Shin, Hye-Rim (College of Pharmacy, Chungnam National University) Lee, Ki-Cheul (College of Pharmacy, Chungnam National University) Hoang, Le Tuan Anh (College of Pharmacy, Chungnam National University) Jung, Sang-Hun (College of Pharmacy, Chungnam National University)

저널정보: 대한약학회 Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea 제31권 제5호

발행연도: 2008.1

수록면: 555 - 561 (7page)

이용수

📌

연구주제

📖

연구배경

🔬

연구방법

🏆

연구결과

초록· 키워드

오류제보하기

The sugar structures of triterpenoid saponins, such as $\alpha$-hederin, are intimately associated with their antitumor activities and other biological activities. The $\alpha$-L-rhamnopyranosyl-($1{\rightarrow}2$)-$\alpha$-L-arabinopyranoside group of $\alpha$-hederin alters the cytotoxicity of its aglycon, hederagenin. This study explored the role of this saccharide unit in the cytotoxic effect of $\alpha$-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-$\alpha$-L-rhamnopyranosyl-($1{\rightarrow}2$)-3,4-O-dibenzoyl-$\beta$-L-arabinopyranoside (2) from 4-methoxybenzoyl-$\beta$-Larabinopyranoside was accomplished using four steps with an overall yield of 63%. The use of $BF_3-OEt_2$ 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-$\alpha$-L-rhamnopyranosyl-($1{\rightarrow}2$)-$\alpha$-L-arabinopyranoside (7), was selectively transformed to 4-methoxybenzoyl-2,3,4-tri-O-benzoyl-$\alpha$-L-rhamnopyranosyl-($1{\rightarrow}2$)-4-O-acetyl-$\alpha$-L-arabinopyranoside (9) and 4-methoxybenzoyl-2,3,4-tri-Obenzoyl-$\alpha$-L-rhamnopyranosyl-($1{\rightarrow}2$)-3-O-benzoyl-$\beta$-L-arabinopyranoside (10). These derivatives did not show any cytotoxicity against human cancer cell lines. Thus the 3-O-$\alpha$-L-rhamnopyranosyl-($1{\rightarrow}2$)-$\alpha$-L-arabinopyranoside could be used as a nontoxic carrier moiety to enhance the activity of anticancer drugs.

#Triterpenoid saponins #Disaccharide moiety$alpha$-Hederin

참고문헌 (0)

참고문헌 신청

참고문헌이 DBpia에서 서비스 중이라면, [참고문헌 신청]을 통해 등록해보세요

함께 읽어보면 좋을 논문

논문 유사도에 따라 DBpia 가 추천하는 논문입니다. 함께 보면 좋을 연관 논문을 확인해보세요!