Facile synthesis of the naturally cytotoxic triterpenoid saponin Patrinia-glycoside B-II and its conformer.
Facile synthesis of the naturally cytotoxic triterpenoid saponin Patrinia-glycoside B-II and its conformer.
复制标题
天然细胞毒性三萜皂苷败酱苷 B-II 及其构象的简便合成
DOI：
10.3390/molecules181215193
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发表时间：
2013-12-10
期刊：
影响因子：
--
通讯作者：
Cheng MS
中科院分区：
文献类型：
--
作者：
Ren L;Liu YX;Lv D;Yan MC;Nie H;Liu Y;Cheng MS
首次化学合成了天然三萜皂苷败酱苷B-II，即油酸3-O-α-L-吡喃鼠李糖基-（1→2）-[β-D-吡喃葡萄糖基-（1→3）]-α-L-吡喃阿拉伯糖苷，总收率9.4%。在制备中间体的过程中，发现阿拉伯糖残基的异常1C 4构象通过构象波动而发生。分子机理和量子化学计算表明，败酱苷B-II与其构象异构体1在正常条件下不能相互转化。初步构效关系研究表明，α-L-吡喃鼠李糖基-（1→2）-α-L-吡喃阿拉伯糖基二糖中阿拉伯糖残基的4C 1椅式构象是其抗肿瘤活性的主要因素之一。
The first chemical synthesis of the natural triterpenoid saponin Patrinia-glycoside B-II, namely oleanolic acid 3-O-α-l-rhamnopyranosyl-(1→2)-[β-d-gluco-pyranosyl-(1→3)]-α-l-arabinopyranoside, has been accomplished in a linear 11-step sequence 11 with 9.4% overall yield. The abnormal 1C4 conformation of the arabinose residue was found to occur via conformational fluctuation during preparation of the intermediates. Molecular mechanism and quantum chemistry calculations showed that Patrinia-glycoside B-II and its conformer 1 cannot interconvert under normal conditions. Preliminary structure-activity relationships studies indicated that the 4C1 chair conformation of the arabinose residue in the unique α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl disaccharide moiety is one of the chief positive factors responsible for its cytotoxic activity against tumors.
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影响因子：
5.1
作者：
Mimaki, Y;Kuroda, M;Sashida, Y
通讯作者：
Sashida, Y
影响因子：
3.5
作者：
Luo, Han-Guang;Ma, Li;Kong, Ling-Yi
通讯作者：
Kong, Ling-Yi
DOI：
10.3390/molecules15117871
发表时间：
2010-11-03
期刊：
Molecules (Basel, Switzerland)
影响因子：
--
作者：
Liu Y;Lu WX;Yan MC;Yu Y;Ikejima T;Cheng MS
通讯作者：
Cheng MS
影响因子：
2
作者：
Jung, HJ;Lee, CO;Park, HJ
通讯作者：
Park, HJ
影响因子：
2.7
作者：
Park, HJ;Kwon, SH;Lee, KT
通讯作者：
Lee, KT