[Journal logo]

Volume 69 
Part 9 
Pages o1369-o1370  
September 2013  

Received 4 July 2013
Accepted 29 July 2013
Online 3 August 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.006 Å
R = 0.045
wR = 0.093
Data-to-parameter ratio = 7.8
Details
Open access

Epibisdehydroneotuberostemonine J

aGuangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou 510632, People's Republic of China, and bSchool of Life Sciences, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, People's Republic of China
Correspondence e-mail: trwjiang@jnu.edu.cn

The title compound, C22H29NO4, a stemona alkaloid, is composed of two lactone rings (A and E), a six-membered ring (B), a pyrrole ring (C) and a seven-membered ring (D). The five-membered rings A and E exhibit envelope conformations (C atoms as flaps) while ring C is planar. Ring B exhibits a twist-chair conformation due to fusion with pyrrole ring C while ring D adopts a chair conformation. The junction between rings A and B is cis. In the crystal, weak C-H...O interactions involving the two carbonyl groups, a methylene and a methyl group give rise to a three-dimensional network.

Related literature

For general background to the structures and biological activity of stemona alkaloids, see: Pilli et al. (2010[Pilli, R.-A., Rossoa, G.-B. & Ferreira de Oliveira, M.-C. (2010). Nat. Prod. Rep. 27, 1908-1937.]). For the antitussive activity of epibisdehydroneotuberostemonine J and other stemona alkaloids, see: Chung et al. (2003[Chung, H.-S., Hon, P.-M., Lin, G., But, P. P.-H. & Dong, H. (2003). Planta Med. 69, 914-920.]); Xu et al. (2010[Xu, Y.-T., Shaw, P.-C., Jiang, R.-W., Hon, P.-M., Chan, Y.-M. & But, P. P.-H. (2010). J. Ethnopharmacol. 128, 679-684.]). For other properties of and studies on Stemona alkaloids, see: Chung et al. (2003[Chung, H.-S., Hon, P.-M., Lin, G., But, P. P.-H. & Dong, H. (2003). Planta Med. 69, 914-920.]); Frankowski et al. (2008[Frankowski, K.-J., Golden, J.-E., Zeng, Y., Lei, Y. & Aubé, J. (2008). J. Am. Chem. Soc. 130, 6018-6024.], 2011[Frankowski, K.-J., Setola, V., Evans, J.-M., Neuenswander, B., Roth, B.-L. & Aubé, J. (2011). Proc. Natl. Acad. Sci. USA, 108, 6727-6732.]); Jiang et al. (2006[Jiang, R.-W., Hon, P.-M., Zhou, Y., Xu, Y.-T., Chan, Y.-M., Xu, Y.-T., Xu, H.-X., Shaw, P.-C. & But, P. P.-H. (2006). J. Nat. Prod. 69, 749-754.]); Zhang et al. (2011[Zhang, R.-R., Ma, Z.-G., Li, G.-Q., But, P. P.-H. & Jiang, R.-W. (2011). Acta Cryst. E67, o3056.]). For an absolute structure reference, see: Jiang et al. (2010[Jiang, R.-W., Ye, W.-C., Shaw, P.-C., But, P. P.-H. & Mak, T. C.-W. (2010). J. Mol. Struct. 966, 18-22.]). For related isomers, see: Pham et al. (2002[Pham, H.-D., Yu, B.-W., Chau, V.-M., Ye, Y. & Qin, G.-W. (2002). J. Asian Nat. Prod. Res. 4, 81-85.]).

[Scheme 1]

Experimental

Crystal data
  • C22H29NO4

  • Mr = 371.46

  • Monoclinic, P 21

  • a = 6.3596 (19) Å

  • b = 18.495 (3) Å

  • c = 8.3875 (15) Å

  • [beta] = 92.521 (18)°

  • V = 985.6 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 291 K

  • 0.43 × 0.28 × 0.20 mm

Data collection
  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.831, Tmax = 1.000

  • 2449 measured reflections

  • 1914 independent reflections

  • 1383 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.093

  • S = 1.05

  • 1914 reflections

  • 245 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5A...O2i 0.97 2.60 3.531 (4) 161
C5-H5B...O4ii 0.97 2.66 3.595 (3) 162
C22-H22B...O4iii 0.96 2.63 3.496 (4) 150
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z]; (ii) x, y, z+1; (iii) x-1, y, z.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SMART and SAINT (Bruker, 1998[Bruker (1998). SMART, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 1998[Bruker (1998). SMART, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2558 ).


Acknowledgements

This work was supported by a grant of the Guangdong High Level Talent Scheme (RWJ) from Guangdong province and the Fundamental Research Funds for the Cental Universities (21612603) from the Ministry of Education, P. R. of China.

References

Bruker (1998). SMART, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Chung, H.-S., Hon, P.-M., Lin, G., But, P. P.-H. & Dong, H. (2003). Planta Med. 69, 914-920.  [ISI] [PubMed] [ChemPort]
Frankowski, K.-J., Golden, J.-E., Zeng, Y., Lei, Y. & Aubé, J. (2008). J. Am. Chem. Soc. 130, 6018-6024.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Frankowski, K.-J., Setola, V., Evans, J.-M., Neuenswander, B., Roth, B.-L. & Aubé, J. (2011). Proc. Natl. Acad. Sci. USA, 108, 6727-6732.  [CrossRef] [ChemPort] [PubMed]
Jiang, R.-W., Hon, P.-M., Zhou, Y., Xu, Y.-T., Chan, Y.-M., Xu, Y.-T., Xu, H.-X., Shaw, P.-C. & But, P. P.-H. (2006). J. Nat. Prod. 69, 749-754.  [ISI] [CrossRef] [PubMed] [ChemPort]
Jiang, R.-W., Ye, W.-C., Shaw, P.-C., But, P. P.-H. & Mak, T. C.-W. (2010). J. Mol. Struct. 966, 18-22.  [ISI] [CSD] [CrossRef] [ChemPort]
Pham, H.-D., Yu, B.-W., Chau, V.-M., Ye, Y. & Qin, G.-W. (2002). J. Asian Nat. Prod. Res. 4, 81-85.  [ISI] [CrossRef] [PubMed] [ChemPort]
Pilli, R.-A., Rossoa, G.-B. & Ferreira de Oliveira, M.-C. (2010). Nat. Prod. Rep. 27, 1908-1937.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Xu, Y.-T., Shaw, P.-C., Jiang, R.-W., Hon, P.-M., Chan, Y.-M. & But, P. P.-H. (2010). J. Ethnopharmacol. 128, 679-684.  [ISI] [CrossRef] [PubMed]
Zhang, R.-R., Ma, Z.-G., Li, G.-Q., But, P. P.-H. & Jiang, R.-W. (2011). Acta Cryst. E67, o3056.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o1369-o1370   [ doi:10.1107/S1600536813021077 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.