Glabridin

Vimon Tantishaiyakul; Krit Suknuntha; Saowanit Saithong; Chaveng Pakawatchai

doi:10.1107/S1600536812048647

. 2012 Nov 30;68(Pt 12):o3501. doi: 10.1107/S1600536812048647

Glabridin

Vimon Tantishaiyakul ^a,^*, Krit Suknuntha ^a, Saowanit Saithong ^b, Chaveng Pakawatchai ^b

PMCID: PMC3589072 PMID: 23476308

Abstract

In the title compound, C₂₀H₂₀O₄ {systematic name: 4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol}, the hydropyran ring linked to the pendant benzene ring adopts an envelope conformation, with the methyne C atom forming the flap. In the crystal, the –OH group at the 3-position of the benzene ring forms an O—H⋯O hydrogen bond to a chromene O-atom acceptor, whereas the –OH group at the 1-position forms an O—H⋯π interaction with a neighboring benzene ring. The O—H⋯O hydrogen bonds form [001] chains and the O—H⋯π bonds cross-link the chains into (101) sheets. The absolute structure was assumed to be the same as that deduced from previous studies for the natural product.

Related literature

For background to the pharmacological activity of the title compound, see: Fukai et al. (2000 ▶); Messier & Grenier; (2011 ▶); Thiyagarajan et al. (2011 ▶); Ahn et al. (2012 ▶); Choi (2005 ▶). For the assignment of the absolute structure, see: Kim et al. (2009 ▶). graphic file with name e-68-o3501-scheme1.jpg

Experimental

Crystal data

C₂₀H₂₀O₄
M _r = 324.36
Orthorhombic,
a = 6.4301 (4) Å
b = 12.0307 (7) Å
c = 21.0690 (13) Å
V = 1629.87 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.22 × 0.14 × 0.07 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T _min = 0.984, T _max = 0.994
15459 measured reflections
2866 independent reflections
2551 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.095
S = 1.16
2866 reflections
225 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and publCIF (Westrip, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(25.8KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048647/hb6989sup1.cif

e-68-o3501-sup1.cif^{(25.8KB, cif)}

Click here for additional data file.^{(140.7KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048647/hb6989Isup2.hkl

e-68-o3501-Isup2.hkl^{(140.7KB, hkl)}

Click here for additional data file.^{(6.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812048647/hb6989Isup3.cml

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

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

Cg4 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O1ⁱ	0.82 (2)	2.02 (2)	2.841 (3)	177 (3)
O3—H3A⋯Cg4ⁱⁱ	0.80 (2)	2.51 (2)	3.213 (2)	148 (3)

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

Acknowledgments

Financial support by the Nanotechnology Center (NANOTEC), NSTDA, Ministry of Science and Technology, Thailand, through Center of Excellence Network program is gratefully acknowledged.

supplementary crystallographic information

Comment

4-[(3R)-8,8-Dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol (Glabridin) is a pyranoisoflavan isolated from licorice. It has various pharmacological activities such as cytotoxic activity (Fukai et al., 2000), antimicrobial activity (Messier & Grenier, 2011), anti-inflammation (Thiyagarajan et al., 2011), anti-obesity effect (Ahn et al., 2012) and prevention for osteoporosis and inflammatory bone diseases (Choi, 2005). For the assignment of its absolute structure, see: Kim et al. (2009).

The molecular structure of the title compound is shown in Fig. 1. The packing features O—H···O intermolecular hydrogen bonding between hydroxyl group at 3 position of benzene ring with the donor-acceptor distance of 2.841 (3) Å. (O4—H4A···O1ⁱ; i: -x + 3/2, -y + 2, z - 1/2) forming a zigzag chains running parallel to the [001] direction. Besides, the O—H···π interactions with O···centroid distances of 3.213 (2) Å are observed between hydroxyl group at the 1 position of benzene ring and the nearby benzene ring of adjacent molecule, O3—H3A···Cg4ⁱⁱ (Cg4 is the centroid of C13—C14—C15—C16—C17—C18 and the symmetry code ii is -x, y + 5/2, -z + 1/2), linking among the zigzag chains generating two-dimensional layer parallel to (101) plane. The crystal packing of interaction is depicted in Fig. 2.

Experimental

The title compound was obtained from Nanjing Zelang Medical Technology Co. Ltd. Colourless blocks were obtained by dissolving the compound in methanol followed by a slow evaporation of the solvent.