Cimitriteromone A–G, Macromolecular Triterpenoid–Chromone Hybrids from the Rhizomes of Cimicifuga foetida,The Journal of Organic Chemistry

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Cimitriteromone A–G, Macromolecular Triterpenoid–Chromone Hybrids from the Rhizomes of Cimicifuga foetida
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-07-25 00:00:00 , DOI: 10.1021/acs.joc.8b01466
Qiang-Qiang Shi _{1,

2,

3} , Jing Lu _{1,

2,

3} , Xing-Rong Peng _{1,

3} , Da-Shan Li _{1,

3} , Lin Zhou _{1,

3} , Ming-Hua Qiu _{1,

2,

3}

Affiliation

Seven unprecedented high molecular weight hybrids of cycloartane triterpenoid saponins and chromone glycosides, namely, Cimitriteromone A–G (1–7), and three known biogenetic precursors (8–10) were isolated from the rhizomes of Cimicifuga foetida by using the HPLC-UV/MS method. The structures of the new compounds were determined by NMR analysis and HRESIMS data. The absolute configurations of sugar moieties were established by a chemical method. The new compounds 2 and 4 showed antiproliferative activities against Taxol-resistant human lung cancer A-549/Taxol with IC₅₀ values of 15.73 ± 0.59 and 24.21 ± 0.61 μM, respectively, while the positive control groups cisplatin and Taxol gave IC₅₀ values of 25.80 ± 1.15 and 0.60 ± 0.09 μM. Notably, compound 4 showed comparable cytotoxicity to the positive control, cisplatin, whereas the corresponding biogenetic precursors compounds 8 and 10 were inactive (IC₅₀ > 40 μM).

中文翻译：

Cimitriteromone A–G，来自Cimicifuga foetida的根茎的大分子三萜类-苯并酮杂种

使用HPLC-UV从Cimicifuga foetida的根茎中分离出七个前所未有的高分子量的环烷三萜类皂苷和色酮糖苷杂合体，即Cimitriteromone A–G（1 – 7）和三个已知的生物遗传前体（8 – 10）。/ MS方法。通过NMR分析和HRESIMS数据确定新化合物的结构。糖部分的绝对构型通过化学方法确定。新化合物2和4对IC _50的抗紫杉醇耐药的人肺癌A-549 / Taxol具有抗增殖活性分别为15.73±0.59和24.21±0.61μM，而阳性对照组顺铂和紫杉醇的IC ₅₀值为25.80±1.15和0.60±0.09μM。值得注意的是，化合物4显示出与阳性对照顺铂相当的细胞毒性，而相应的生物遗传前体化合物8和10没有活性（IC ₅₀ > 40μM）。

更新日期：2018-07-25

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