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X-ray powder diffraction data for schisanhenol

Published online by Cambridge University Press:  10 October 2013

Li Li Zhang ,
Dan Xiao ,
Xia Lin ,
Wei Luo ,
Si Li  and
Hui Li
Li Li Zhang
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Dan Xiao
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Xia Lin
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Wei Luo
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Si Li
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
Hui Li*
Affiliation:
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
*
a)Author to whom correspondence should be addressed. Electronic mail: lihuilab@sina.com
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Abstract

Experimental X-ray powder diffraction data, unit-cell parameters and space group for schisanhenol, C23H30O6, are reported [a = 14.6157 Å, b = 12.8801 Å, c = 11.4907 Å, unit-cell volume V = 2163.14 Å3, Z = 4, and space group P212121]. All of the measured lines were indexed and are consistent with the P212121 space group. No detectable impurities were observed.

Keywords

X-ray powder diffractionschisanhenolSchisandra chinensisRietveld refinement
Type
New Diffraction Data
Information
Powder Diffraction , Volume 29 , Issue 1 , March 2014 , pp. 48 - 50
Copyright
Copyright © International Centre for Diffraction Data 2013 

I. INTRODUCTION

Schisanhenol, systematic name (6S, 7R,)-2,3,10,11,12-pentamethoxy-6,7-dimethyl-5,6,7,8-tetrahydrodibenzo[a,c][8]annulen-1-ol, is an important lignan of Schisandra chinensis (Turcz.) Baill, which was first described by Liu et al. (Reference Liu, Huang and Gao1978). Schisanhenol (Figure 1) has strong biological activities and pharmacological properties, which was shown to be the most active one in inhibiting microsome lipid oxidation (Yu et al., Reference Yu, Liu, Sun and Zhang2004). Schisanhenol absolutely inhibited the preoxidative damages of brain mitochondria and membrane of rats. The swelling and disintegration of brain mitochondria, as well as the reduction of brain fluidity were also restrained by schisanhenol (Xue et al., Reference Xue, Liu, Wei and Pan1992). In addition, schisanhenol exhibits various beneficial activities including antihepatitis, antitumor, and anti-HIV effects (Chen et al., Reference Chen, Kilgore, Lee and Chen2006).

Figure 1. Structural formula of schisanhenol.

The crystal structure of schisanhenol was solved by Xu et al. (Reference Xu, Bao and He1982), which was confirmed by single-crystal measurement.

II. EXPERIMENTAL

A. Sample preparation

The title compound was extracted, isolated, and purified from S. chinensis, and the natural sample was characterized by high-performance liquid chromatography (HPLC), as well as by UV, IR, and MS. Then, the pure schisanhenol (>98% purity) was recrystallized in petroleum ether–ethyl acetate (5:1, v/v).

B. Diffraction data collection and reduction

The diffraction pattern for the target compound was collected at room temperature using an X'Pert PRO diffractometer (PANalytical) with an X'celerator detector and Cu Kα 1 radiation (λ = 1.54056 Å, generator setting: 40 kV, 30 mA). The diffraction data were collected over the angular range from 5 to 50°2θ with a step size of 0.01313°2θ and a counting time of 10.16 ms step−1. Data evaluation was performed using the software package Material Studio 4.2 (Accelrys Co., Ltd. USA).

Indexing was conducted using peak positions obtained from the powder diffraction profiles by X-cell method then the indexing result was refined with the type of Pawley (Pan et al., Reference Pan, Guo, Duan, Cheng and Li2012). MC/SA search algorithm in Powder Solve package (Engel et al., Reference Engel, Wilke, König, Harris and Leusen1999) was used to constantly adjust the conformation, position, and orientation of the trial model in the unit cell of schisanhenol, and then the result of Powder Solve was refined by Rietveld refinement techniques. In the Rietveld refinement (Young, Reference Young1993), variables defining the structural model and the powder diffraction profile were adjusted by least squares methods in order to obtain an optimal fit between the experimental pattern and the calculated pattern. After Rietveld refinement, the final R wp was converged at 7.60%.

III. RESULTS

The experimental powder diffraction pattern is depicted in Figure 2. Indexing results show that schisanhenol is orthorhombic with space group P212121 and unit-cell parameters: a = 14.6157 Å, b = 12.8801 Å, c = 11.4907 Å, unit-cell volume V = 2163.14 Å3, Z = 4, and space group P212121 (Table I). All of the lines were indexed and are consistent with the P212121 space group.

Figure 2. X-ray powder diffraction pattern of schisanhenol, using Cu Kα 1 radiation (λ = 1.54056 Å).

Table I. Indexed X-ray powder diffraction data of schisanhenol, C23H30O6. Only the peaks with I rel of 1 or greater are reported [a = 14.6157 Å, b = 12.8801 Å, c = 11.4907 Å, unit-cell volume V = 2163.14 Å3, Z = 4, and space group P212121]. All of the measured lines were indexed and are consistent with the P212121 space group. The d-values were calculated using CuKα1 radiation (λ = 1.54056 Å).

After Rietveld refinement, the structure of schisanhenol was solved. At the same time, single-crystal data were collected on an Oxford Diffraction Xcalibur Nova system with Mo Kα radiation (λ = 0.71073 Å) at room temperature and θ from 3.05° to 28.77°, in that way to verify whether the powder data are accurate. A comparison of the unit-cell parameters from powder data and from single-crystal data reported by Xu et al. (Reference Xu, Bao and He1982) shows significant consistency, which indicates that X-ray powder diffraction as a means of crystal structure solution is credible.

References

Chen, M., Kilgore, N., Lee, K. H., Chen, D. F. (2006). “Rubrisandrins A and B, lignans and related anti-HIV compounds from Schisandra rubriflora ,” J. Nat. Prod. 69, 1697–1701.CrossRefGoogle Scholar
Engel, G. E., Wilke, S., König, O., Harris, K. D. M. and Leusen, F. J. J. (1999). “Powder Solve – a complete package for crystal structure solution from powder diffraction patterns,” J. Appl. Crystal. 32, 1169–1179.Google Scholar
Liu, J. S., Huang, M. F., Gao, Y. L. (1978). “Studies on the constituents of Yi–Geng–Wu–Zi (Schisandra henr yi clarke)-I The structures of schisanhenol and deoxyschisandrin,” Acta Chim. Sin. 36, 193–197.Google Scholar
Pan, Q. Q., Guo, P., Duan, J., Cheng, Q. and Li, H. (2012). “Comparative crystal structure determination of griseofulvin: Powder X-ray diffraction versus Single-crystal X-ray diffraction,” Chin. Sci. Bull. 57, 3867–3871.Google Scholar
Xu, C. F., Bao, G. H., He, C. H. (1982). “The crystal structure of Schisanhenol,” Kexue Tongbao (in Chinese) 27, 1081–1084.Google Scholar
Xue, J. Y., Liu, G. T., Wei, H. L., Pan, Y. (1992). “Antioxidant activity of two dibenzocyclooctene lignans on the aged and ischemic brain in rats,” Free Radical Biol. Med. 12, 127–135.Google Scholar
Young, R. A. (1993). The Rietveld Method, IUCr Monographies of Crystallography (Wiley, Oxford).Google Scholar
Yu, L. H., Liu, G. T., Sun, Y. M., Zhang, H. Y. (2004). “Antioxidative effect of schisanhenol on human low density lipoprotein and its quantum chemical calculation,” Acta Pharmacol. Sin. 25, 1038–1044.Google Scholar
Figure 0

Figure 1. Structural formula of schisanhenol.

Figure 1

Figure 2. X-ray powder diffraction pattern of schisanhenol, using Cu Kα1 radiation (λ = 1.54056 Å).

Figure 2

Table I. Indexed X-ray powder diffraction data of schisanhenol, C23H30O6. Only the peaks with Irel of 1 or greater are reported [a = 14.6157 Å, b = 12.8801 Å, c = 11.4907 Å, unit-cell volume V = 2163.14 Å3, Z = 4, and space group P212121]. All of the measured lines were indexed and are consistent with the P212121 space group. The d-values were calculated using CuKα1 radiation (λ = 1.54056 Å).

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