5,6,7,5′-Tetra­meth­oxy-3′,4′-methyl­ene­dioxy­flavone monohydrate

Hou-Jin Li; Da-Lang Zhou; Ting-Juan Xu; Chi-Keung Lam; Wen-Jian Lan

doi:10.1107/S1600536812015139

. 2012 Apr 13;68(Pt 5):o1390. doi: 10.1107/S1600536812015139

5,6,7,5′-Tetramethoxy-3′,4′-methylenedioxyflavone monohydrate

Hou-Jin Li ^a, Da-Lang Zhou ^a, Ting-Juan Xu ^a, Chi-Keung Lam ^a, Wen-Jian Lan ^b,^*

PMCID: PMC3344517 PMID: 22590279

Abstract

The title compound [systematic name: 5,6,7-trimethoxy-2-(7-methoxy-1,3-dihydro-2-benzofuran-5-yl)-4H-chromen-4-one monohydrate], C₂₀H₁₈O₈·H₂O, was isolated from the popular Chinese medicinal plant Entada phaseoloides. In the crystal, inversion-related molecules are joined by pairs of weak C—H⋯O hydrogen bonds. The dimers are further interconnected by a bridging water molecule via weak C—H⋯O_water and pairs of (O—H)_water⋯O hydrogen bonds into a linear tape running parallel to the b axis.

Related literature

For the isolation of 5,6,7,5′-tetramethoxy-3′,4′-methylenedioxyflavone, see: Chen et al. (1984 ▶); Vyas et al. (1986a ▶); Souza et al. (1995 ▶); Tomazela et al. (2000 ▶). For the NMR spectroscopic studies, see Vyas et al. (1986b ▶). For the biological activity of flavonoids, see: Genoux et al. (2011 ▶); Bodewes et al. (2011 ▶); Jacob et al. (2011 ▶); Veitch & Grayer (2011 ▶).

Experimental

Crystal data

C₂₀H₁₈O₈·H₂O
M _r = 404.36
Triclinic,
a = 9.3014 (17) Å
b = 9.3146 (17) Å
c = 11.009 (2) Å
α = 105.413 (3)°
β = 91.798 (3)°
γ = 100.985 (3)°
V = 899.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 173 K
0.41 × 0.35 × 0.32 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.772, T _max = 1.000
6560 measured reflections
3181 independent reflections
2608 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.117
S = 1.07
3181 reflections
270 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015139/bg2446sup1.cif

e-68-o1390-sup1.cif^{(28.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015139/bg2446Isup2.hkl

e-68-o1390-Isup2.hkl^{(156KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812015139/bg2446Isup3.cml

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

Enhanced figure: interactive version of Fig. 1

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11⋯O5	0.83 (2)	2.03 (2)	2.823 (2)	160 (3)
O1W—H12⋯O4	0.83 (2)	2.33 (3)	2.987 (2)	137 (3)
C3—H3A⋯O5ⁱ	0.95	2.41	3.255 (2)	147
C8—H8A⋯O1Wⁱⁱ	0.95	2.42	3.372 (2)	175

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 30973633), the Guangdong Provincial Science and Technology Research Program (Nos. 2009B030801199, 2010B030800002 and 2010B030600011), the Research Program from the Administration of Traditional Chinese Medicine of Guangdong Province (No. 20111164) and the Fund for Undergraduate Innovative Experiment and Research of Guangdong Province (No.1055811012).

supplementary crystallographic information

Comment

Flavonoids are an important secondary metabolites produced in some medicinal or dietary plants. They are reported to show diverse biological activities, including antioxidant, anti-inflammatory, anti-cancer activities, as well as slowing down the progression of cardiovascular and neurodegenerative diseases (Genoux et al., 2011; Bodewes et al., 2011; Jacob et al., 2011; Veitch et al., 2011).

Entada phaseoloides (L.) Merr., a popular Chinese medicinal plant, is distributed widely in the South China and the trunk has been used clinically for a long time to treat rheumatism. The title compound, 5,6,7,5'-tetramethoxy-3',4'-methylenedioxyflavone was isolated from the ethanol extract of Entada phaseoloides. In the crystals, the methoxy oxygen atom and the adjacent carbonyl oxygen atom are bridged by a water molecule via O1w—H11···O5 and O1w—H12···O4 hydrogen bonds. Neighboring molecules related by an inversion centre are joined together via a pair of weak C3—H···O5═C4 hydrogen bonds. The molecules are further cross linked by a weak C8'-H···O5═C and C8—H8A···O1w intermolecular interactions.

Experimental

The trunk of Entada phaseoloides (L.) Merr. was successively extracted three times with ethanol. The extract was concentrated by low-temperature rotary evaporation and chromatographed on a silica gel column with a petroleum ether–EtOAc–MeOH gradient as the eluent to afford 20 fractions (Fr. 1–Fr. 20). Fr. 8–10 were further purified by RP-HPLC eluted with H₂O–MeCN (60:40, v/v) to yield 5,6,7,5'-tetramethoxy-3',4'-methylenedioxyflavone. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the compound in EtOAc.