(E)-3-(4-Hydr­oxy-3-methoxy­benzyl­idene)-4-(4-hydroxy­phen­yl)pyrrolidin-2-one

Yi-Feng Zhou; Xiao-Bing Wang; Jin Qi; Bo-Yang Yu

doi:10.1107/S1600536808008581

. 2008 Apr 10;64(Pt 5):o814. doi: 10.1107/S1600536808008581

(E)-3-(4-Hydroxy-3-methoxybenzylidene)-4-(4-hydroxyphenyl)pyrrolidin-2-one

Yi-Feng Zhou ^a, Xiao-Bing Wang ^b, Jin Qi ^a, Bo-Yang Yu ^a,^*

PMCID: PMC2961252 PMID: 21202304

Abstract

The title compound, C₁₈H₁₇NO₄, was isolated from an ethanol extract of Ophiopogon japonicus. The dihedral angle between the 4-hydroxy-3-methoxyphenyl ring and the pyrrolidine ring is 17.4 (1)°. The 4-hydroxyphenyl ring makes a dihedral angle of 69.74 (6)° with the least-squares plane through the 4-hydroxy-3-methoxyphenyl ring and the pyrrolidine ring. The conformation of the pyrrolidine fragment is similar to a T-form. The crystal structure is stabilized by intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the chemical components and pharmacological properties of the plant Ophiopogon japonicus, see: Anh et al. (2003 ▶); Kou et al. (2005 ▶) & Yu (2007 ▶). For related literature, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₈H₁₇NO₄
M _r = 311.33
Monoclinic,
a = 6.388 (1) Å
b = 14.520 (2) Å
c = 16.880 (2) Å
β = 96.514 (2)°
V = 1555.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.47 × 0.42 × 0.35 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T _min = 0.954, T _max = 0.969
9225 measured reflections
3387 independent reflections
1756 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.137
S = 1.02
3387 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT; data reduction: SAINT (Bruker, 2001 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008581/lx2053sup1.cif

e-64-0o814-sup1.cif^{(20KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008581/lx2053Isup2.hkl

e-64-0o814-Isup2.hkl^{(134.8KB, 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
N—H1⋯O1ⁱ	0.86	2.09	2.948 (2)	172
O2—H2⋯O1ⁱⁱ	0.82	1.95	2.675 (2)	147
O4—H4⋯O2ⁱⁱⁱ	0.82	2.00	2.721 (2)	147

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

Acknowledgments

This research was financially supported by the National Natural Science Foundation of China (grant No. 30672603 to Dr Bo-Yang Yu).

supplementary crystallographic information

Comment

The plant of Ophiopogon japonicus (L. f.) Ker-Gawl.(Liliaceae) is widely distributed in South-east Asia, especially in most areaof China, and its tuber root as a famous traditional medicine are widely usedin China to cure acute and chronic inflammation and cardiovascular diseasesincluding thrombotic diseases for thousands of years (Yu, 2007; Kou, et al., 2005). Chemical studies have shown that this plant includes steroidal saponins, homoisoflavonoids andmonoterpene glycosides etc (Anh, et al., 2003). Herein we report the molecular and crystal structure of the title compound (Fig.1), which was isolated from an ethanol extract of the plant of Ophiopogon japonicus.

The main components of the title compound were two aromatic rings, A(C5—C10) and B(C12—C17) and a pyrrolidine ring C(N1/C1—C4) as shown in Fig. 1. Fig. 2 presents the packing diagram of the title compound. Paired molecules at the inversional position assembled via supromolecular sython R₂²(8) (Bernstein, et al., 1995) which consist of hydrogen bonds N1—H1···O1ⁱ, O2—H2···O1ⁱⁱ and O4—H4···O2ⁱⁱⁱ (Symmetry code as in Fig. 2.).

Experimental

Material from the dried subterranean parts of Ophiopogon japonicus (L. f.) Ker-Gawl.(Liliaceae) (40 kg),collected from Sichuan Province in China, was extracted with hot 60% EtOH (3×3 h) under refluxing. The concentrated extract was subjected to D-101 macroporous resin column chromatography eluted successively with EtOH-H₂O(0:100, 30:70, 90:100) to give three fractions (I-III). The concentratedresidue of fraction III (EtOH-H₂O, 90:10) (330 g) was further dissolved in water, and extractedwith EtOAc and n-BuOH successively. The EtOAc extract (107 g) was loaded onto a silica-gel column (200–300 mesh, 600 g) eluted with a gradientof 100% CHCl₃ to CHCl₃—MeOH (50:50) to give 18 fractions,which was pooled by common thin-layer chromatography characteristics. Fraction9 was subjected to repeated chromatography over silica-gel and Sephadex LH-20columns, gave compound (I) (yield 6 mg, m.p. 518 K). Prismatic crystalssuitable for X-ray studies were grown from MeOH by slow evaporation at roomtemperature.