Received 4 July 2013
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: email@example.com
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-HO interactions involving the two carbonyl groups, a methylene and a methyl group give rise to a three-dimensional network.
For general background to the structures and biological activity of stemona alkaloids, see: Pilli et al. (2010). For the antitussive activity of epibisdehydroneotuberostemonine J and other stemona alkaloids, see: Chung et al. (2003); Xu et al. (2010). For other properties of and studies on Stemona alkaloids, see: Chung et al. (2003); Frankowski et al. (2008, 2011); Jiang et al. (2006); Zhang et al. (2011). For an absolute structure reference, see: Jiang et al. (2010). For related isomers, see: Pham et al. (2002).
Data collection: SMART (Bruker, 1998); cell refinement: SMART and SAINT (Bruker, 1998); data reduction: SAINT and XPREP (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in 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: ZL2558 ).
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.
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.
Frankowski, K.-J., Golden, J.-E., Zeng, Y., Lei, Y. & Aubé, J. (2008). J. Am. Chem. Soc. 130, 6018-6024.
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, 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.
Jiang, R.-W., Ye, W.-C., Shaw, P.-C., But, P. P.-H. & Mak, T. C.-W. (2010). J. Mol. Struct. 966, 18-22.
Pham, H.-D., Yu, B.-W., Chau, V.-M., Ye, Y. & Qin, G.-W. (2002). J. Asian Nat. Prod. Res. 4, 81-85.
Pilli, R.-A., Rossoa, G.-B. & Ferreira de Oliveira, M.-C. (2010). Nat. Prod. Rep. 27, 1908-1937.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.
Zhang, R.-R., Ma, Z.-G., Li, G.-Q., But, P. P.-H. & Jiang, R.-W. (2011). Acta Cryst. E67, o3056.