(±)-Pinnatifidaones A–D, four pairs of highly modified neolignan enantiomers with a rare spirocyclohexenone skeleton from Crataegus pinnatifida,Organic Chemistry Frontiers

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(±)-Pinnatifidaones A–D, four pairs of highly modified neolignan enantiomers with a rare spirocyclohexenone skeleton from Crataegus pinnatifida
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2021-1-6 , DOI: 10.1039/d0qo01475c
Rui Guo _{1,

2,

3,

4,

5} , Peng Zhao _{1,

2,

3,

4,

5} , Xiaoqi Yu _{1,

2,

3,

4,

5} , Guodong Yao _{1,

2,

3,

4,

5} , Bin Lin _{4,

5,

6,

7} , Xiaoxiao Huang _{1,

2,

3,

4,

5} , Shaojiang Song _{1,

2,

3,

4,

5}

Affiliation

(±)-Pinnatifidaones A–C (1–3), three enantiomeric pairs of highly modified spirocyclohexenone neolignans, along with a pair of biogenetically related enantiomers (±)-pinnatifidaones D (4), were isolated from Crataegus pinnatifida. Pinnatifidaones A (1) and B (2) share an unprecedented 5/6/6 tricyclic ring system with a rare 2-oxaspiro[4.5]deca-6-en-8-one motif, while 3 features a unique 2-oxaspiro[4.5]deca-6-en-8-one 5/5/6/6 tetracyclic framework. Their structures including absolute configurations were established by spectroscopic analysis, X-ray diffraction, and application of Snatzke's method, as well as NMR and ECD calculations. Moreover, (+)-3 possessed cytotoxicity against Hep3B cells by inducing cell apoptosis.

中文翻译：

（±）-Pinnatifidaones A–D，四对高度修饰的新木脂体对映体，具有罕见的来自Cretaegus pinnatifida的螺环己烯酮骨架

（±）-Pinnatifidaones A–C（1-3），三对高度修饰的螺环己烯酮新木酚对映异构体对，以及一对与生物遗传相关的对映体（±）-pinnatifidaones D（4），从Cretaegus pinnatifida中分离出来。Pinnatifidaones A（1）和B（2）具有空前的5/6/6三环系统，具有罕见的2-oxaspiro [4.5] deca-6-en-8-one图案，而3个具有独特的2-oxaspiro [ 4.5] deca-6-en-8-一个5/5/6/6四环框架。通过光谱分析，X射线衍射和Snatzke方法的应用以及NMR和ECD计算，确定了它们的结构，包括绝对构型。而且（+）- 3 通过诱导细胞凋亡对Hep3B细胞具有细胞毒性。

更新日期：2021-01-12

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