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Volume 66 
Part 8 
Pages o2111-o2112  
August 2010  

Received 10 July 2010
Accepted 16 July 2010
Online 24 July 2010

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Key indicators
Single-crystal X-ray study
T = 110 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.096
Data-to-parameter ratio = 9.2
Details
Open access

Xyloccensin L

Gang Feng,a* Jing Zhang,a Jun Li,b Tirumani Satyanandamurtyc and Jun Wub*

aEnvironment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Danzhou 571737, People's Republic of China,bKey Laboratory of Marine Bio-resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, People's Republic of China, and cGovernment Degree College at Amadala Valasa, Srikakulam District, Andhra Pradesh, 532185, India
Correspondence e-mail: feng8513@sina.com, wwujun2003@yahoo.com

The title compound, C32H40O10, also known as xyloccensin L [systematic name: (1R,4aR,4bS,5aR,6aR,9R,10S,10aS,10bR,2aR,13R)-1-(furan-3-yl)-6a-hydroxy-10-(2-methoxy-2-oxoethyl)-9,10a,12a-trimethyl-3-oxododecahydro-1H,3H,5aH-6,9-methanoisochromeno[6,5-f]oxireno[g]chromen-13-yl (2E)-2-methylbut-2-enoate], is a limonoid with a C1-C29 oxygen bridge: this is the first report of the X-ray crystal structure of such a limonoid. Two fused pyran rings and two cyclohexane rings adopt boat conformations, while another cyclohexane ring and the d-lactone ring are in half-chair conformations. The molecular structure is stabilized by intramolecular O-H...O hydrogen bonding.

Related literature

The title compound was isolated from seeds of an Indian mangrove, Xylocarpus moluccensis, collected in the mangrove wetlands of the Godavari estuary, Andhra Pradesh. For previous investigations of the seeds of Xylocarpus granatum and X. moluccensis, see: Kubo et al. (1976[Kubo, I., Miura, I. & Nakanishi, K. (1976). J. Am. Chem. Soc. 98, 6704-6705.]); Ng et al. (1979[Ng, A. S. & Fallis, A. G. (1979). Can. J. Chem. 57, 3088-3089.]); Alvi et al. (1991[Alvi, K. A., Crews, P., Aalbersberg, B., Prasad, R., Simpson, J. & Weavers, R. T. (1991). Tetrahedron, 47, 8943-8948.]); Kokpol et al. (1996[Kokpol, U., Chavasiri, W., Tip-pyang, S., Veerachato, G. & Zhao, F. L. (1996). Phytochemistry, 41, 903-905.]); Mulholland et al. (2000[Mulholland, D. A., Parel, B. & Coombes, P. H. (2000). Curr. Org. Chem. 4, 1011-1054.]). For our group's work in this field, see: Wu et al. (2004a[Wu, J., Xiao, Q., Huang, J.-S., Xiao, Z.-H., Qi, S.-H., Li, Q.-X. & Zhang, S. (2004a). Org. Lett. 6, 1841-1844.],b[Wu, J., Zhang, S., Xiao, Q., Li, Q.-X., Huang, J.-S., Long, L.-J. & Huang, L.-M. (2004b). Tetrahedron Lett. 45, 591-593.], 2005[Wu, J., Xiao, Q., Zhang, S., Li, X., Xiao, Z.-H., Ding, H.-X. & Li, Q.-X. (2005). Tetrahedron, 61, 8382-8389.], 2008a[Wu, J., Zhang, S., Bruhn, T., Xiao, Q., Ding, H.-X. & Bringmann, G. (2008a). Chem. Eur. J. 14, 1129-1144.],b[Wu, J., Xiao, Q., Xu, J., Li, M.-Y., Pan, J.-Y. & Yang, M.-H. (2008b). Nat. Prod. Rep. 25, 955-981.]).

[Scheme 1]

Experimental

Crystal data

  • C32H40O10

  • Mr = 584.64

  • Orthorhombic, P 21 21 21

  • a = 8.3859 (4) Å

  • b = 11.0454 (5) Å

  • c = 31.0799 (13) Å

  • V = 2878.8 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 110 K

  • 0.46 × 0.44 × 0.25 mm
Data collection

  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.956, Tmax = 0.976

  • 14701 measured reflections

  • 3569 independent reflections

  • 3202 reflections with I > 2[sigma](I)

  • Rint = 0.026
Refinement

  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.096

  • S = 1.03

  • 3569 reflections

  • 386 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.59 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O6 0.84 2.08 2.774 (2) 139

Data collection: SMART (Bruker, 2004[Bruker (2004). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97 .

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2224 ).

Acknowledgements

Financial support of this work by the Important Project of Chinese Academy of Sciences (KSCX2-YW-R-093, KZCX2-YW-216), the National High Technology Research and Development Program of China (863 Program) (2007AA09Z407), the National Natural Science Foundation of China (20772135) and the Research Foundation for Young Talents from the South China Sea Institute of Oceanology, Chinese Academy of Sciences (M-YL SQ200802) is gratefully acknowledged.

References

Alvi, K. A., Crews, P., Aalbersberg, B., Prasad, R., Simpson, J. & Weavers, R. T. (1991). Tetrahedron, 47, 8943-8948.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Kokpol, U., Chavasiri, W., Tip-pyang, S., Veerachato, G. & Zhao, F. L. (1996). Phytochemistry, 41, 903-905.  [CrossRef] [ChemPort] [ISI]
Kubo, I., Miura, I. & Nakanishi, K. (1976). J. Am. Chem. Soc. 98, 6704-6705.  [CrossRef] [ChemPort] [PubMed] [ISI]
Mulholland, D. A., Parel, B. & Coombes, P. H. (2000). Curr. Org. Chem. 4, 1011-1054.  [ISI] [CrossRef] [ChemPort]
Ng, A. S. & Fallis, A. G. (1979). Can. J. Chem. 57, 3088-3089.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wu, J., Xiao, Q., Huang, J.-S., Xiao, Z.-H., Qi, S.-H., Li, Q.-X. & Zhang, S. (2004a). Org. Lett. 6, 1841-1844.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Wu, J., Xiao, Q., Xu, J., Li, M.-Y., Pan, J.-Y. & Yang, M.-H. (2008b). Nat. Prod. Rep. 25, 955-981.  [CrossRef] [PubMed] [ChemPort]
Wu, J., Xiao, Q., Zhang, S., Li, X., Xiao, Z.-H., Ding, H.-X. & Li, Q.-X. (2005). Tetrahedron, 61, 8382-8389.  [ISI] [CSD] [CrossRef] [ChemPort]
Wu, J., Zhang, S., Bruhn, T., Xiao, Q., Ding, H.-X. & Bringmann, G. (2008a). Chem. Eur. J. 14, 1129-1144.  [CrossRef] [ChemPort]
Wu, J., Zhang, S., Xiao, Q., Li, Q.-X., Huang, J.-S., Long, L.-J. & Huang, L.-M. (2004b). Tetrahedron Lett. 45, 591-593.  [ISI] [CrossRef] [ChemPort]

Acta Cryst (2010). E66, o2111-o2112   [ doi:10.1107/S1600536810028527 ]

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