Kokosanolide from the seed of Lansium domesticum Corr

Tri Mayanti; Unang Supratman; Mat Ropi Mukhtar; Khalijah Awang; Seik Weng Ng

doi:10.1107/S1600536809008009

. 2009 Mar 14;65(Pt 4):o750. doi: 10.1107/S1600536809008009

Kokosanolide from the seed of Lansium domesticum Corr.

Tri Mayanti ^a, Unang Supratman ^a, Mat Ropi Mukhtar ^b, Khalijah Awang ^b, Seik Weng Ng ^b,^*

PMCID: PMC2968903 PMID: 21582481

Abstract

In the title compound, [systematic name: 8,14-secogammacera-7,14(27)-diene-3,21-dione], C₂₇H₃₂O₉, each of the six-membered rings adopts the common chair conformation. In the crystal, molecules are linked by an O–H⋯O_ester hydrogen bond into a helical chain.

Related literature

For compounds from this plant species, see: Habaguchi et al. (1968 ▶); Kiang et al. (1967 ▶); Nishizawa et al. (1982 ▶, 1983 ▶, 1984 ▶, 1985 ▶, 1988 ▶); Saewan et al. (2006 ▶).

Experimental

Crystal data

C₂₇H₃₂O₉
M _r = 500.53
Monoclinic,
a = 8.8326 (1) Å
b = 12.8977 (2) Å
c = 11.1555 (1) Å
β = 110.777 (1)°
V = 1188.19 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 123 K
0.40 × 0.30 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
11333 measured reflections
2856 independent reflections
2760 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.083
S = 1.03
2856 reflections
331 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008009/bt2893sup1.cif

e-65-0o750-sup1.cif^{(25.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008009/bt2893Isup2.hkl

e-65-0o750-Isup2.hkl^{(140.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯O2ⁱ	0.84	2.01	2.854 (2)	178

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Directorate of Higher Education, Indonesia, University of Padjadjaran (I-MHERE Project) and the Sciencefund (12–02-03–2063).

supplementary crystallographic information

Experimental

Lansium domesticum Corr. (Meliaceae) was collected in Cililin, Bandung, Indonesia, in 2006. The plant was identified by the staff at Department of Biology, Padjadjaran University. The dried and milled seeds of L.domesticum (2 kg) was extracted exhaustively by methanol at room temperature. The methanol extract (84 g) was partitioned between n-hexane and 10% aqueous methanol to give an n-hexane soluble fraction (4 g). The n-hexane extract were subjected to column chromatography on silica gel 60 by using step gradient of n-hexane and dichloromethane (8:2). The fraction eluted by n-hexane/dichloromethane (6:4) was further separated by column chromatography on silica gel (n-hexane:ethyl acetate 7:3) to give kokosanolide (48 mg).