In vitro anticancer studies of α- and β-D-glucopyranose betulin anomers
In vitro anticancer studies of α- and β-D-glucopyranose betulin anomers
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DOI：
10.1016/j.cbi.2010.02.038
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发表时间：
2010-04-29
影响因子：
5.1
通讯作者：
Paschke, Reinhard
中科院分区：
文献类型：
--
作者：
Kommera, Harish;Kaluderovic, Goran N.;Paschke, Reinhard
合成了四种在 C3 位含有 D-吡喃葡萄糖基部分的桦木醇衍生物，并通过 H-1 和 C-13 NMR 光谱以及质谱进行了表征。测定了28-O-乙酰基桦木醇-3-基-β-D-(2',3',4',6'-四-O-乙酰基)吡喃葡萄糖苷的晶体结构。这些化合物针对十五种不同组织起源的肿瘤细胞系进行了测试。 28-O-乙酰桦木醇-3-基-D-吡喃葡萄糖苷的α-和β-端基异构体对肿瘤细胞系发挥剂量依赖性抗增殖作用。 HCT-116细胞处理24小时诱导细胞凋亡，这通过DNA片段化分析和细胞周期分析中典型阶梯图案的出现而得到证实。 28-O-乙酰基桦木醇-3-基-D-吡喃葡萄糖苷的 α-和 β-端基异构体似乎通过激活结肠癌 HCT-116 细胞系上不同的上游半胱天冬酶来诱导细胞凋亡。 (C) 2010 Elsevier Ireland Ltd. 保留所有权利。
Four derivatives of betulin containing a D-glucopyranosyl moiety at C3 position were synthesized and characterized by H-1 and C-13 NMR spectroscopy as well as mass spectrometry. The crystal structure of 28-O-acetylbetulin-3-yl-beta-D-(2',3',4',6'-tetra-O-acetyl)glucopyranoside was determined. The compounds were tested against fifteen tumor cell lines of different histogenic origins. The alpha- and beta-anomers of 28-O-acetylbetulin-3-yl-D-glucopyranoside, exerted a dose dependent antiproliferative action towards the tumor cell lines. Treatment of HCT-116 cells for 24 h induced apoptosis, which was confirmed by the appearance of a typical ladder pattern in the DNA fragmentation assay and cell cycle analysis. The alpha- and beta-anomers of 28-O-acetylbetulin-3-yl-D-glucopyranoside seem to induce apoptosis by activation of different upstream caspases on colon cancer HCT-116 cell line. (C) 2010 Elsevier Ireland Ltd. All rights reserved.