Oxyresveratrol from Mulberry as a dihydrate

Hui Deng; Xixin He; Yujuan Xu; Xiaopeng Hu

doi:10.1107/S1600536812014018

. 2012 Apr 6;68(Pt 5):o1318–o1319. doi: 10.1107/S1600536812014018

Oxyresveratrol from Mulberry as a dihydrate

Hui Deng ^a, Xixin He ^b, Yujuan Xu ^b, Xiaopeng Hu ^a,^*

PMCID: PMC3344458 PMID: 22590220

Abstract

The title compound {systematic name: 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol dihydrate}, C₁₄H₁₂O₄·2H₂O, a derivative of resveratrol, was isolated from mulberry. The linking C=C double bond has a trans conformation and allows the formation of a conjugated system throughout the molecule. The dihedral angle between the benzene rings is 9.39 (9)°. In the crystal, molecules are connected into a three-dimensional architecture through O—H⋯O hydrogen bonds between hydroxy groups of oxyresveratrol and solvent water molecules.

Related literature

For medicinal properties and the biological activity of oxyresveratrol, see: Mongolsuk et al. (1957 ▶); Charoenlarp et al. (1981 ▶, 1989 ▶); Zheng et al. (2010 ▶, 2011 ▶); Kim et al. (2002 ▶, 2004 ▶); Shin et al. (1998 ▶); Lipipun et al. (2011 ▶); Galindo et al. (2011 ▶); Sasivimolphan et al. (2009 ▶); Chuanasa et al. (2008 ▶); Likhitwitayawuid (2008 ▶); Likhitwitayawuid et al. (2005 ▶, 2006 ▶); Liu et al. (2009 ▶); Breuer et al. (2006 ▶); Chung et al. (2003 ▶); Chao et al. (2008 ▶); Ban et al. (2006 ▶, 2008 ▶); Breuer et al. (2006 ▶); Andrabi et al. (2004 ▶). For related structures, see: Piao et al. (2009 ▶); Qiu et al.(1996 ▶); Hano et al. (1986 ▶).

Experimental

Crystal data

C₁₄H₁₂O₄·2H₂O
M _r = 280.27
Triclinic,
a = 6.6523 (5) Å
b = 9.2005 (9) Å
c = 11.5294 (8) Å
α = 72.533 (7)°
β = 78.686 (6)°
γ = 79.651 (7)°
V = 654.51 (9) Å³
Z = 2
Cu Kα radiation
μ = 0.95 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.20 mm

Data collection

Agilent Xcalibur Onyx Nova diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.704, T _max = 0.834
4145 measured reflections
2297 independent reflections
2002 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.141
S = 1.13
2297 reflections
197 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014018/tk5080sup1.cif

e-68-o1318-sup1.cif^{(22.2KB, cif)}

Supplementary material file. DOI: 10.1107/S1600536812014018/tk5080Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014018/tk5080Isup3.hkl

e-68-o1318-Isup3.hkl^{(112.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812014018/tk5080Isup4.cml

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
O1—H1⋯O4ⁱ	0.84	1.90	2.7329 (18)	173
O2—H2⋯O6ⁱⁱ	0.84	1.89	2.720 (2)	171
O3—H3A⋯O6ⁱⁱⁱ	0.84	1.97	2.8045 (19)	169
O4—H4⋯O5^iv	0.84	1.89	2.7259 (19)	170
O5—H5A⋯O1ⁱ	0.89 (2)	1.90 (2)	2.7879 (19)	172 (2)
O5—H5B⋯O2^v	0.89 (2)	1.88 (2)	2.7449 (19)	161 (2)
O6—H6B⋯O2ⁱⁱ	0.90 (3)	1.95 (3)	2.720 (2)	143 (4)
O6—H6C⋯O6^vi	0.90 (4)	1.87 (4)	2.7583 (19)	172 (5)

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

Acknowledgments

The authors gratefully thank the Scientific Research Foundation for Returned Overseas Chinese Scholars (X. He), the State Education Ministry, the National Natural Science Foundation of China, (30800169, X. Hu) and the Research Fund for the Doctoral Program of Higher Education of China (200805581146, X. Hu).

supplementary crystallographic information

Comment

Oxyresveratrol was firstly isolated from the heartwood of Artocarpus lakoocha Roxb as a abundant trans-tetrahydroxystilbene (Mongolsuk et al., 1957). Oxyresveratrol is responsible for the anthelmintic activity of the traditional Thailand anthelmintic drug "Puag-Haad" prepared from A. lakoocha (Charoenlarp et al., 1989; Charoenlarp et al., 1981). Recent investigations have revealed several interesting bioactivities of oxyresveratrol, such as tyrosinase inhibitory activity (Zheng et al., 2011; Zheng et al., 2010; Kim et al., 2004; Kim et al., 2002; Shin et al., 1998), in vitro anti-viral activity (Lipipun et al., 2011; Galindo et al., 2011; Sasivimolphan et al., 2009; Chuanasa et al., 2008; Likhitwitayawuid et al., 2006; Likhitwitayawuid et al., 2005), strong anti-oxidative and anti-inflammatory (Liu et al., 2009; Breuer et al., 2006; Chung et al., 2003), and neuroprotective properties (Chao et al., 2008; Ban et al., 2008; Ban et al., 2006; Breuer et al., 2006; Andrabi et al., 2004). These medicinal properties indicate several areas of therapeutic potential for oxyresveratrol and the compound has been recommended as a drug candidate for the treatment of neurodegenerative disorders (Breuer et al., 2006; Andrabi et al., 2004) and a skin-whitening agent in cosmetic preparations (Likhitwitayawuid, 2008). Mulberry (Morus alba L.) is a medicinal plant in east Asia. Its branch, leaf, ripe fruit and root bark are well known traditional Chinese drugs and contain a large amounts of trans-hydroxystilbenes such as mulberroside A, phaponticin, phapontigenin, resveratrol, pterostilbene, piceatannol, piceid, astringin, kuwanon Y, kuwanon Z, oxyresveratrol and its derivatives (Qiu et al., 1996; Hano et al., 1986; Piao et al., 2009). In this paper, we isolated oxyresveratrol from mulberry (Morus alba L.) and report the structure of oxyresveratrol dihydrate.

In the title compound (Fig. 1), the benzene rings form a dihedral angle of 9.39 (9)°. The presence of the trans C═C double bond allows the formation of a conjugated system, strongly stabilized through π-electron delocalization. The trans-double bond is the same as found in similar structures (Piao et al., 2009; Qiu et al., 1996; Hano et al., 1986). The molecules of the oxyresveratrol are connected into a three-dimensional architecture through O—H—O hydrogen bonds formed between its hydroxyl group and the solvent water molecules (Fig. 2 and Table 1).

Experimental

The dried root bark of Morus alba L. (1 kg) was powdered and extracted with 95% ethanol at room temperature for 48 h. After removal of the solvent under reduced pressure, a brown extract was suspended with water, and sequentially partitioned with petroleum ether, acetyl acetate and n-butanol. The acetyl acetate extract (9 g) was subjected to column chromatography on silica gel (200–300 mesh) with increasing concentrations of ethyl acetate in petroleum ether. Oxyresveratrol was afforded from the fraction (petroleum ether-ethyl acetate 6/4, v/v). The title compound was colourless to light-yellow crystal with M.pt: 474–476 K,. Crystals suitable for X-ray analysis were obtained by slow evaporation from its chloroform–methanol (4/1, v/v) solution. ¹H NMR (400 MHz, MeOD) δ 7.33 (d, J = 9.2 Hz, 1H), 7.27 (d, J = 16.5 Hz, 1H), 6.82 (d, J = 16.4 Hz,1H), 6.46 (d, J = 2.1 Hz, 2H), 6.34 – 6.32 (m, 1H), 6.31 (s, 1H), 6.15 (t, J = 2.2 Hz, 1H); O—H not observed.