Martin-Luther-Universität Halle-Wittenberg, Halle, Germany.
Chem Biol Interact. 2010 Apr 29;185(2):128-36. doi: 10.1016/j.cbi.2010.02.038. Epub 2010 Mar 1.
Four derivatives of betulin containing a D-glucopyranosyl moiety at C3 position were synthesized and characterized by (1)H and (13)C 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 24h 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.
合成了 4 种桦木醇的衍生物，它们在 C3 位含有一个 D-吡喃葡萄糖基。通过 1H 和 13C NMR 光谱以及质谱对其进行了表征。确定了 28-O-乙酰基桦木醇-3-β-D-(2',3',4',6'-四-O-乙酰基)吡喃葡萄糖苷的晶体结构。这些化合物对 15 种不同组织来源的肿瘤细胞系进行了测试。28-O-乙酰基桦木醇-3-β-D-吡喃葡萄糖苷的α-和β-异构体对肿瘤细胞系表现出剂量依赖性的增殖抑制作用。用 HCT-116 细胞处理 24 小时可诱导细胞凋亡，这在 DNA 片段化分析和细胞周期分析中出现典型的梯状模式得到了证实。28-O-乙酰基桦木醇-3-β-D-吡喃葡萄糖苷的α-和β-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诱导细胞凋亡。
