(3R,6R,12R,20S,24S)-3,6,12-Triacetyl-20,24-ep­oxy­dammarane-3,6,12,25-tetra­ol

Guo, H.-M.; Wang, L.; Wang, N.; Zhang, J.-F.; Meng, Q.-G.

doi:10.1107/S1600536810050749

Volume 67
Part 1
Page o59
January 2011

Received 18 November 2010
Accepted 3 December 2010
Online 11 December 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.045
wR = 0.115
Data-to-parameter ratio = 9.1
Details

(3R,6R,12R,20S,24S)-3,6,12-Triacetyl-20,24-epoxydammarane-3,6,12,25-tetraol

Huan-Mei Guo,^a Liang Wang,^b Nan Wang,^b Jiang-Feng Zhang ^b and Qing-Guo Meng ^b ^*

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China, and ^bSchool of Pharmacy, Yantai University, Yantai 264005, People's Republic of China
Correspondence e-mail: mqg@ytu.edu.cn

The title compound, C₃₆H₅₈O₈, was prepared from 20(S)-protopanaxatriol, which was degraded from Panax quinquefolium saponin with sodium in glycerine, extracted and seperated by flash chromatography. Three six-membered rings are in chair conformations, the five-membered ring is in an envelope form and the tetrahydrofuran ring has a conformation intermediate between half-chair and envelope. In the crystal, molecules are linked by O-HO hydrogen bonds, and C-HO contacts also occur. The absolute structure was assigned on the basis of the synthesis.

Related literature

For background to the medicinal uses of Araliaceae-type natural products, see: Shibata et al. (1985); Takano et al. (1999); Yu et al. (2007); Wang et al. (2010). For related structures, see: Iljin et al. (1982); Shi et al. (1992).

Experimental

Crystal data

C₃₆H₅₈O₈
M_r = 618.82
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.6936 (11) Å
b = 16.151 (2) Å
c = 28.439 (4) Å
V = 3533.7 (9) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 298 K
0.41 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
18696 measured reflections
3738 independent reflections
2746 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.115
S = 1.04
3738 reflections
409 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O8ⁱ	0.82	2.36	3.050 (4)	142
C8-H8O8ⁱ	0.98	2.58	3.526 (4)	161
C35-H35CO6ⁱⁱ	0.96	2.45	3.403 (5)	172
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5749 ).

Acknowledgements

The authors thank Mr. Lian-dong Liu (College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University) for his invaluable support with the X-ray data collection. The authors would like to thank Shandong Provincial Natural Science Foundation, China (Y2007C138), and the Scientific Reasearch Foundation of the Higher Education Institutions of Shandong Province and China (J07WE26) for a research grant.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Iljin, S. G., Mallnovskaya, G. V., Uvarova, N. I. & Elyakov, G. B. (1982). Tetrahedron Lett. pp. 5067-5070.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shi, Q., Hen, K., Jioka, T. & Mhiwada, Y. (1992). J. Nat. Prod. pp. 1488-1497.
Shibata, S., Tanaka, L., Shoji, L. & Saito, H. (1985). Econ. Med. Res. 1, 217-284.
Takano, K., Midori, T., Eiichiro, I. & Teruo, M. (1999). Cancer Lett. 147, 11-16.
Wang, T., Meng, Q. G., Zhang, J. F., Bi, Y. & Jiang, N. C. (2010). Fitoterapia, 81, 783-787.
Yu, C., Fu, F. H., Yu, X., Han, B. & Zhu, M. (2007). Arzneimittelforschung, 57, 568-572.

organic compounds