Absolute Configuration of Periplosides C and F and Isolation of Minor Spiro-orthoester Group-Containing Pregnane-type Steroidal Glycosides from Periploca sepium and Their T-Lymphocyte Proliferation Inhibitory Activities.
Absolute Configuration of Periplosides C and F and Isolation of Minor Spiro-orthoester Group-Containing Pregnane-type Steroidal Glycosides from Periploca sepium and Their T-Lymphocyte Proliferation Inhibitory Activities.
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DOI：
10.1021/acs.jnatprod.7b00017
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发表时间：
2017-03
影响因子：
5.1
通讯作者：
Luoyi Wang;Jun-jun Qin;Zhen-hua Chen;Yu Zhou;Wei Tang;Jian-Ping Zuo;Weimin Zhao
中科院分区：
文献类型：
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作者：
Luoyi Wang;Jun-jun Qin;Zhen-hua Chen;Yu Zhou;Wei Tang;Jian-Ping Zuo;Weimin Zhao
对杠柳根皮的进一步植物化学研究得到9个新的含螺原酸酯基团的孕烷型糖苷，命名为杠柳苷O-V和3-O-甲酰基杠柳苷A。根据光谱数据解释和化学转化，阐明了这些糖苷的结构沿着独特的七元甲酰基缩醛桥连螺原酸酯官能团和4，6-双脱氧-3-O-甲基-Δ3-2-己糖磺酰基部分的绝对构型。通过单晶X-射线衍射分析确定了主要化合物杠柳苷C和F的绝对构型。评价了分离的化合物对T淋巴细胞增殖的抑制活性。结果表明，香芹苷C是该植物中最丰富的含有螺原酸酯部分的糖苷，表现出最受欢迎的选择性指数值（SI = 82.5）。杠柳苷中糖链的长度和结构影响抑制活性和SI值。
Further phytochemical investigation of the root bark of Periploca sepium afforded nine new spiro-orthoester group-containing pregnane-type glycosides termed periplosides O-V and 3-O-formyl-periploside A. The structures of these glycosides along with the absolute configuration of the unique seven-membered formyl acetal-bridged spiro-orthoester function and the 4,6-dideoxy-3-O-methyl-Δ3-2-hexosulosyl moiety were elucidated on the basis of spectroscopic data interpretation and chemical transformation. The absolute configurations of the major compounds periplosides C and F were established by single-crystal X-ray diffraction analysis. The isolated compounds were evaluated for their inhibitory activities against the proliferation of T-lymphocytes. As a result, periploside C, the most abundant glycoside containing a spiro-orthoester moiety found in the plant, exhibited the most favorite selective index value (SI = 82.5). The length and constitution of the saccharide chain in the periplosides were found to influence the inhibitory activity and the SI value.