Absolute configuration of curdione and its three
isomers by NMR, ECD and DFT calculations: an insight
into the scope of unsaturated ketone helicity rule
based on an ECD study

Absolute configuration of curdione and its three isomers by NMR, ECD and DFT calculations: an insight into the scope of unsaturated ketone helicity rule based on an ECD study

Feiting Zhang, Yuxin Li, Tianhui Zhu, Wenhe Zhang, Bin Qin*, Song You*

School of Life Sciences & Biopharmaceutical Sciences, Shenyang Pharmaceutical University, Shenyang 110016, China

Received:2016-06-30 Revised:2017-09-11 Online:2018-02-20 Published:2018-04-03
Contact: School of Life Sciences & Biopharmaceutical Sciences, Shenyang Pharmaceutical University, Shenyang ??00?6, China; E-mail: to- qinbin@?63.com (B. Qin); yousong206@aliyun.com (S. You); Tel.:+86-24-23986436.

Abstract

Abstract: The stereostructures of curdione and its other three isomers with two stereogenic centers, C-4 and C-7, were studied each by electronic circular dichroism (ECD) spectroscopy and nuclear magnetic resonance (NMR) spectroscopy for determination of their absolute configurations. Their expected spectra based upon the density functional theory calculations were reasonably well agreed on experimental spectra. Furthermore, it was reported for the first time that these compounds, which have the unsaturated ketone groups with the distance between the two unsaturated carbon atoms less than about 2.55Å, can be applied to the unsaturated ketone helicity rule.

Key words: Curdione, NMR, ECD, DFT, Helicity rul

Feiting Zhang, Yuxin Li, Tianhui Zhu, Wenhe Zhang, Bin Qin, Song You. Absolute configuration of curdione and its three isomers by NMR, ECD and DFT calculations: an insight into the scope of unsaturated ketone helicity rule based on an ECD study[J]. Asina Journal Of Traditional Medicines.

[1]	Ya Pan;Hongxia Liu;Liqin Ding;Yulei Zhuang;Feng Qiu . Complete assignment of ¹H and ¹³C signals of a triterpene from Agrimonia pilosa* Ledeb. by 2D NMR [J]. , 2009, 4(4): 147-151.
[2]	Zhaohua Wu;Shunwang Huang;Chunyan Liu;Bohang Sun;Jian Huang; Lijun Wu * . A novel compound from Curcuma longa [J]. , 2008, 3(5): 199-202.
[3]	Minglei Cai;Zhaohua Wu;Jian Huang;Bohang Sun;Zhishu Tang; Xiaomei Song;Lijun Wu* . A new compound from Rabdosia rubescens [J]. , 2008, 3(2): 76-79.
[4]	Jia Chen;Shaojiang Song ;Jun He;Suixu Xu. A study of the chemical constituents of the leaves of Crataegus pinnatifida* [J]. , 2008, 3(2): 80-83.
[5]	Yongyi Wang;Jian Huang;Huiming Hua;Bohang Sun;Huiyuan Gao;Lijun Wu * . Structural determination of taxacin from the twigs and leaves of Taxus cuspidata Sieb. et Zucc. using 2D NMR spectral methods [J]. , 2007, 2(4): 162-165.
[6]	Huan Chen;Li Qiao;Yuzhi Zhou;Yao Yao;Jiaqing Cao;Huiming Hua; Yuehu Pei . Structure determination of a C-19 steriod from the roots of Cynanchum amplexicaule* [J]. , 2007, 2(3): 115-117.
[7]	Chunyan Liu;Bohang Sun;Jian Huang;Huiyuan Gao;Shaodun Wen;Lijun Wu * . A Novel Sesquiterpene from Curcuma longa [J]. , 2007, 2(2): 82-84.
[8]	Xiaoqiu Liu;Weiwei Li;Huiming Hua;Wen Li;Fakui Chen;Lijun Wu. An NMR Study of a Phenyl Propanoid-substituted Catechin from Polygonum bistorta* [J]. , 2006, 1(2): 73-75.
[9]	Yanqiang Yuan;Huiyuan Gao;Bin Wu;Zhishu Tang;Dongyan Guo;Xiaomei Song;Lijun Wu. Structure Determination of a Novel Natural Product From the Root of Panax Notoginseng* [J]. , 2006, 1(2): 91-93.
[10]	Yeming Zhou;Huiyuan Gao;Bin WU;Shuhui Li;and Lijun Wu＊. Structure Determination of Syringopicroside from the Leaves of Syringa Oblata Lindl. using 2D NMR Spectral Methods [J]. , 2006, 1(1): 31-33.
[11]	Yue Cong*;Wen Li;Changda Liu;Jinhu Wang;and Xian Li . Application of HSQC-TOCSY to the Analysis of Saponins [J]. , 2006, 1(1): 20-24.

Asian Journal
Of Traditional Medicines