8-O-Acetyl-8-epi-9-de­oxygoniopypyrone

Hoong-Kun Fun; Suchada Chantrapromma; Uma Prawat; Nawong Boonnak; Ibrahim Abdul Razak

doi:10.1107/S1600536812010483

. 2012 Mar 17;68(Pt 4):o1072–o1073. doi: 10.1107/S1600536812010483

8-O-Acetyl-8-epi-9-deoxygoniopypyrone

Hoong-Kun Fun ^a,^*,^‡, Suchada Chantrapromma ^b,^§, Uma Prawat ^c, Nawong Boonnak ^b, Ibrahim Abdul Razak ^a

PMCID: PMC3344029 PMID: 22589938

Abstract

The title compound (systematic name: 7-oxo-3-phenyl-2,6-dioxabicyclo[3.3.1]nonan-4-yl acetate), C₁₅H₁₆O₅, is a styryllactone derivative which was isolated from Goniothalamus macrophyllus. The molecule has two fused rings consisting of a tetrahydro-2H-pyran and a lactone ring, with the benzene ring and the acetyl group attached to the tetrahydro-2H-pyran ring. The tetrahydro-2H-pyran ring is in a standard chair conformation, whereas the lactone ring is in an envelope conformation. In the crystal, molecules are linked by weak C—H⋯O interactions into sheets parallel to the ac plane. Weak C—H⋯π interactions are also observed.

Related literature

For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For background to Goniothamus plants and the bioactivity of styryllactone compounds, see: Abdul-Wahab et al. (2011 ▶); Goh et al. (1995 ▶); Jiang et al. (2011 ▶); Smitinand (2001 ▶); Wattanapiromsakul et al. (2005 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₅H₁₆O₅
M _r = 276.28
Monoclinic,
a = 10.1013 (3) Å
b = 5.7749 (2) Å
c = 11.2295 (3) Å
β = 95.207 (1)°
V = 652.36 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.59 × 0.43 × 0.43 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.940, T _max = 0.956
24278 measured reflections
3105 independent reflections
3044 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.027
wR(F ²) = 0.074
S = 1.08
3105 reflections
245 parameters
1 restraint
All H-atom parameters refined
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010483/rz2717sup1.cif

e-68-o1072-sup1.cif^{(24.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010483/rz2717Isup2.hkl

e-68-o1072-Isup2.hkl^{(152.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010483/rz2717Isup3.cml

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

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

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2ⁱ	0.988 (15)	2.398 (15)	3.3563 (10)	163.2 (11)
C11—H11⋯O5ⁱⁱ	0.981 (16)	2.531 (16)	3.4986 (12)	168.9 (14)
C15—H15A⋯O5ⁱⁱⁱ	0.99 (2)	2.43 (2)	3.4048 (12)	167 (2)
C2—H2A⋯Cg1^iv	0.986 (16)	2.714 (15)	3.4619 (9)	133.0 (11)
C12—H12⋯Cg1ⁱⁱ	0.97 (2)	2.947 (18)	3.6566 (10)	130.9 (14)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

SC and NB thank Prince of Songkla University for financial support through the Crystal Materials Research Unit. UP thanks Phuket Rajabhat University for a research grant. The authors also thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

Goniothalamus macrophyllus, a Thai medicinal plant, which is known in Thai as "Ching Dok Diao" belongs to the genus Goniothalamus (Smitinand, 2001). A study of methanolic extracts from the roots and stems of G. macrophyllus shows that the methanolic extracts exhibit good cytotoxicity against breast and lung carcinoma cancer cell lines with IC₅₀ value in range 3.16-5.04 µg/mL (Wattanapiromsakul et al., 2005). In addition, methanolic extract from the leaves of G. umbrosus showed antoxidant, antibacterial and antiviral activities (Abdul-Wahab et al., 2011). The previous reports by Goh et al. (1995) and Jiang et al. (2011) showed that plants in Goniothalamus genus produce styryllactone compounds as major constituents and most of them exhibit potent cytotoxic activity. The above investigations has prompted us to search for cytotoxic components from Goniothalamus plants. Our research on bioactive compounds from G. macrophyllus yields the title compound (I), 8-O-Acetyl-8-epi-9-deoxygoniopypyrone. Herein the crystal structure of (I) was reported.

The molecule of (I) has a bicyclic skeleton (Fig. 1). The tetrahydro-2H-pyran ring (C3–C7/O3) is in a standard chair conformation whereas the lactone ring (C1–C5/O1/O2) adopts an envelope conformation with the puckering C4 atom having a deviation of 0.3806 (9) Å and puckering parameters Q = 0.5424 (9) Å, θ = 49.39 (9)° and φ = 234.03 (12)° (Cremer & Pople, 1975). The benzene ring is attached to the tetrahydro-2H-pyran ring at atom C7. The acetyl group is planar with the r.m.s. deviation of 0.0015 (1) Å for the four non-H atoms (C14/C15/O4/O5). The orientation of the acetyl group is described by the torsion angles C6–O4–C14–C15 = 175.73 (7)° and C6–O4–C14–O5 = -3.72 (12)°. The bond distances in (I) are within normal ranges (Allen et al., 1987).

In the crystal packing (Fig. 2), the molecules are linked into sheets parallel to the ac plane by weak C—H···O interactions (Table 1). Weak C—H···π interactions (Table 1) are also observed.

Experimental

The title compound was isolated from the methanolic extract of the G. macrophyllus by repeated column chromatography. Single crystals suitable for X-ray structure determination were obtained as colorless block-shaped crystals by slow evaporation of the solvent at room temperature after several days. M. p. 467–469 K.