3-epi-Dammarenediol II 1.075 hydrate: a dammarane triterpene from the bark of Aglaia eximia

Fun, H.-K.; Chantrapromma, S.; Supriadin, A.; Harneti, D.; Supratman, U.

doi:10.1107/S1600536812040366

Volume 68
Part 11
Pages o3089-o3090
November 2012

Received 29 August 2009
Accepted 24 September 2012
Online 10 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.058
wR = 0.162
Data-to-parameter ratio = 13.7
Details

3-epi-Dammarenediol II 1.075 hydrate: a dammarane triterpene from the bark of Aglaia eximia

Hoong-Kun Fun,^a,^b ^*⁺ Suchada Chantrapromma,^c ⁺⁺ Asep Supriadin,^d Desi Harneti ^d and Unang Supratman ^d

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia,^cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^dDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Padjadjaran University, Jatinangor 45363, West Java, Indonesia
Correspondence e-mail: hkfun@usm.my

The title dammarane tritepene, 3 [alpha] ,20(S)-dihydroxydammar-24-ene, which crystallized out in a hydrated form, C₃₀H₅₂O₂.1.075H₂O, was isolated from the Aglaia eximia bark. The three cyclohexane rings adopt chair conformations. The cyclopentane has an envelope conformation with the quaternary C at position 14 as the flap atom with the maximum deviation of 0.288 (2) Å. The methylheptene side chain is disordered over two positions with 0.505 (1):0.495 (1) site occupancies and is axially attached with an (+)-syn-clinal conformation. The hydroxyl group at position 3 of dammarane is in a different conformation to the corresponding hydroxyl in Dammarenediol II. In the crystal, the dammarane and water molecules are linked by O_Dammarane-HO_water and O_water-HO_Dammarane hydrogen bonds into a three-dimensional network.

Related literature

For ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For background to Aglaia plants, triterpenoids and their biological activity, see: Asakawa et al. (1977); Chairgulprasert et al. (2006); Greger et al. (2001); Grosvenor et al. (1995); Lima et al. (2004); Qiu et al. (2001); Roux et al. (1998); Yodsaoue et al. (2012); Zhang et al. (2010). For related structures, see: Qiu et al. (2001). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).

Experimental

Crystal data

C₃₀H₅₂O₂·1.075H₂O
M_r = 463.99
Tetragonal, P 4₂
a = 19.9481 (13) Å
c = 7.3410 (7) Å
V = 2921.2 (5) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 100 K
0.39 × 0.11 × 0.10 mm

Data collection

Bruker APEX Duo CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.975, T_max = 0.994
24864 measured reflections
4543 independent reflections
3887 reflections with I > 2(I)
R_int = 0.064

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.162
S = 1.07
4543 reflections
332 parameters
1 restraint
H-atom parameters constrained
_max = 0.72 e Å^-3
_min = -0.48 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H1O2O1W	0.84	2.02	2.816 (3)	157
O1W-H1W1O1ⁱ	0.84	1.94	2.783 (3)	175
O2W-H1W2O2ⁱⁱ	0.83	1.89	2.718 (3)	177
Symmetry codes: (i) $[y, -x+1, z+{\script{1\over 2}}]$ ; (ii) x, y, z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2209 ).

Acknowledgements

AS, DH and US thank Padjadjaran University for financial support. HKF and SC thank Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Asakawa, J., Kasai, R., Yamasaki, K. & Tanaka, O. (1977). Tetrahedron, 33, 1935-1939.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chairgulprasert, V., Krisornpornsan, B. & Hamad, A. (2006). Songklanakarin J. Sci. Technol. 28, 321-326.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Greger, H., Pacher, T., Bream, B., Bacher, M. & Hofer, O. (2001). Phytochemistry, 57, 57-64.
Grosvenor, P. W., Supriono, A. & Gray, D. O. (1995). J. Ethnopharm. 45, 97-111.
Lima, M. da P., Braga, P. A. de C., Macedo, M. L., Silva, M. F., da das, G. F., Ferreira, A. G., Fernandes, J. B. & Vierira, P. C. (2004). J. Braz. Chem. Soc. 15, 385-394.
Qiu, S.-X., van Hung, N., Xuan, L. T., Gu, J.-Q., Lobkovsky, E., Khanh, T. C., Soejarto, D. D., Clardy, J., Pezzuto, J. M., Dong, Y., Tri, M. V., Huong, L. M. & Fong, H. H. S. (2001). Phytochem. 56 775-780.
Roux, D., Martin, M.-T., Adeline, M.-T., Sevenet, T., Hadi, A. H. A. & Pais, M. (1998). Phytochemistry, 49, 1745-1748.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yodsaoue, O., Sonprasit, J., Karalai, C., Ponglimanont, C., Tewtrakul, S. & Chantrapromma, S. (2012). Phytochemistry, 76, 83-91.
Zhang, F., Wang, J. S., Gu, J. S. & Kong, L. Y. (2010). J. Nat. Prod. 73, 2042-2046.

organic compounds

3-epi-Dammarenediol II 1.075 hydrate: a dammarane triterpene from the bark of Aglaia eximia

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References