Efficient synthesis of α- and β-chacotriosyl glycosides using appropriate donors, and their cytotoxic activity
Efficient synthesis of α- and β-chacotriosyl glycosides using appropriate donors, and their cytotoxic activity
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DOI：
10.1016/j.carres.2008.02.012
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发表时间：
2008-06-09
影响因子：
3.1
通讯作者：
Ikeda, Tsuyoshi
中科院分区：
文献类型：
--
作者：
Miyashita, Hiroyuki;Kai, Yuuki;Ikeda, Tsuyoshi
低聚糖部分含有α-L-鼠李糖基-(1-gt；4)-[α-L-鼠李糖基-(1-gt；2)]-β-D-吡喃葡萄糖苷的天然甾体糖苷具有抗癌和抗疱疹活性。为了研究查考三糖苷类苷元部分的构效关系，我们开发了一种具有不同苷元的查考三糖苷类化合物的合成方法。在此过程中，发现主要通过三氯乙酰亚胺酸酯供体可以得到α-乳糖三糖苷，而β-乳糖三糖苷可以通过亚磷酸盐和磷酸盐供体得到。在A549和HepG2细胞系的细胞毒性测试中，自然产生的β-查考三糖苷元和胆甾醇显示出比相应的α-查考三糖苷更高的活性。(C)2008爱思唯尔有限公司。保留所有权利。
Natural steroidal glycosides containing alpha-L-rhamnopyranosyl-(1 -> 4)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-beta-D-glucopyranose (chacotriose) at the oligosaccharide moiety exhibit anti-cancer and anti-herpes activities. To investigate the structure-Activity relationships of the aglycone parts of chacotriosides, we developed a synthesis method for chacotriosyl glycosides having various aglycones. In the process, it was revealed that alpha-chacotriosyl glycosides could be obtained mainly by using a trichloroacetimidate donor, while beta-chacotriosyl glycosides were afforded by using phosphite and phosphate donors. In cytotoxicity tests using the A549 and HepG2 cell lines, naturally occurring beta-chacotriosyl diosgenin and cholestanol exhibited higher activities than the corresponding alpha-chacotriosyl glycosides. (C) 2008 Elsevier Ltd. All rights reserved.