(3R,4S)-3,4,8-Trihy­droxy-1,2,3,4-tetra­hydro­naphthalen-1-one monohydrate from Embellisia eureka

Ouchbani, T.; Zouihri, H.; Essassi, E.M.; Proksch, P.; Ng, S.W.

doi:10.1107/S1600536812022623

organic compounds

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doi:10.1107/S1600536812022623

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(3R,4S)-3,4,8-Trihydroxy-1,2,3,4-tetrahydronaphthalen-1-one monohydrate from Embellisia eureka

Tarik Ouchbani,^a Hafid Zouihri,^b El Mokhtar Essassi,^a Peter Proksch ^c and Seik Weng Ng ^d,^e ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bCNRST Division UATRS, Angle Allal Fassi/ FAR, BP 8027 Hay Riad, Rabat, Morocco, ^cInstitut für Pharmazeutische Biologie und Biotechnologie, Heinrich Heine University Düsseldorf, Gebäude 26.23, Universitätsstrasse 1, 40225 Düsseldorf, Germany, ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^eChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 17 May 2012; accepted 17 May 2012; online 26 May 2012)

In the title hydrate, C₁₀H₁₀O₄·H₂O, the six-membered aliphatic ring that is fused to the benzene ring has a sofa shape, with the hydroxy group in the 3-position (that represents the sofa back) of the aliphatic ring occupying a quasi-axial position. The hydroxy group of the aromatic ring is hydrogen-bond donor to the carbonyl O atom; other O—H⋯O hydrogen bonds link the organic molecules and the water molecules into a three-dimensional network.

Related literature

For the isolation of the title compound from other fungi, see: Borgschulte et al. (1991 ); Iwasaki et al. (1972 ); Trisuwan et al. (2008 ). The absolute configuration was assumed from published assignments, see: Trisuwan et al. (2008).

Experimental

Crystal data

C₁₀H₁₀O₄·H₂O
M_r = 212.20
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.6430 (4) Å
b = 14.3904 (11) Å
c = 14.4976 (10) Å
V = 968.65 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.31 × 0.28 × 0.24 mm

Data collection

Bruker APEX DUO diffractometer
6331 measured reflections
1320 independent reflections
916 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.096
S = 0.99
1320 reflections
156 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84 (1)	1.87 (3)	2.590 (3)	143 (3)
O1—H1⋯O1wⁱ	0.84 (1)	2.27 (3)	2.829 (3)	124 (3)
O3—H2⋯O1ⁱⁱ	0.84 (1)	2.15 (3)	2.924 (3)	153 (5)
O4—H3⋯O1wⁱⁱⁱ	0.85 (1)	1.82 (1)	2.657 (3)	170 (4)
O1w—H4⋯O2	0.84 (1)	1.98 (1)	2.805 (3)	167 (4)
O1w—H5⋯O4^iv	0.85 (1)	1.88 (1)	2.726 (3)	177 (3)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x-{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, -y+2, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812022623/xu5544sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022623/xu5544Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022623/xu5544Isup3.cml

checkCIF report

Comment top

3,4-Dihydro-3,4,8-trihydroxy-1[2H]-naphthalenone is a secondary metabolite produced by several endophytic fungi,e.g., Hypoxylon mammatum (Borgschulte et al., 1991), Nigrospora sp. (Trisuwan et al., 2008) and Pyrichularia orayzae (Iwasaki et al., 1972). The compound was isolated from Embellisia eureka in this study; the compound was found to crystallize as a monohydrate (Scheme I). In the hydrate, C₁₀H₁₀O₄^.H₂O, the six-membered aliphatic ring that is fused to the benzene ring has a soft shape. The C-3 atom represents the sofa back. The hydroxy group of the aliphatic ring occupies a quasi-axial position (Fig. 1). The hydroxy group of the aromatic ring is hydrogen-bond donor to the carbonyl O atom; other O—H···O hydrogen bonds link the organic molecule and water molecule to form a 3D network (Table 1).

Related literature top

For the isolation of the compound from other fungi, see: Borgschulte et al. (1991); Iwasaki et al. (1972); Trisuwan et al. (2008).

Experimental top

Fungal extraction

The fungal strain, Embellisia eureka, was identified by PCR. About 250 ml of ethyl acetate was added into each culture material of the fungus in an Erlenmeyer flask. The ethyl acetate phase was then concentrated under reduced pressure. The residue was diluted in 90% aqueous methanol and further extracted with n-hexane to remove fatty acids and other non-polar constituents. The remaining 90% methanol phase was evaporated under reduced pressure to yield 3.0 g of crude product.

Isolation protocol of 3,4-dihydro-3,4,8-trihydroxy-1[2H]-naphthalenone

The 90% methanol extract was submitted to vacuum liquid chromatography on a column packed with silica as the stationary phase,. The resulting fraction was submitted two successive fractionations on a Sephadex column packed with Sephadex LH-20 as stationary phase. The mobile phase was the 100% methanol. This gave 113.4 mg of a material that was purified by using the semi-preparative HPLC to give 7.0 mg of the pure compound. Crystals were obtained by slow evaporation of a methanol: water (9:1) solution of the compound.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₀H₁₀O₄^.H₂O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

(3R,4S)-3,4,8-Trihydroxy-1,2,3,4-tetrahydronaphthalen-1-one monohydrate top

Crystal data top

C₁₀H₁₀O₄·H₂O	F(000) = 448
M_r = 212.20	D_x = 1.455 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1057 reflections
a = 4.6430 (4) Å	θ = 2.8–21.8°
b = 14.3904 (11) Å	µ = 0.12 mm⁻¹
c = 14.4976 (10) Å	T = 293 K
V = 968.65 (13) Å³	Prism, brown
Z = 4	0.31 × 0.28 × 0.24 mm

Data collection top

Bruker APEX DUO diffractometer	916 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.063
Graphite monochromator	θ_max = 27.5°, θ_min = 2.8°
ω scans	h = −6→5
6331 measured reflections	k = −18→17
1320 independent reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0507P)²] where P = (F_o² + 2F_c²)/3
1320 reflections	(Δ/σ)_max = 0.001
156 parameters	Δρ_max = 0.21 e Å⁻³
5 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₀H₁₀O₄·H₂O	V = 968.65 (13) Å³
M_r = 212.20	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.6430 (4) Å	µ = 0.12 mm⁻¹
b = 14.3904 (11) Å	T = 293 K
c = 14.4976 (10) Å	0.31 × 0.28 × 0.24 mm

Data collection top

Bruker APEX DUO diffractometer	916 reflections with I > 2σ(I)
6331 measured reflections	R_int = 0.063
1320 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	5 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.21 e Å⁻³
1320 reflections	Δρ_min = −0.21 e Å⁻³
156 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.5051 (5)	0.75199 (14)	0.74392 (14)	0.0280 (6)
O2	0.1740 (5)	0.83227 (14)	0.62424 (12)	0.0281 (5)
O3	0.1933 (5)	1.08380 (14)	0.69719 (15)	0.0262 (5)
O4	−0.0651 (5)	1.10191 (16)	0.87414 (16)	0.0318 (5)
O1w	0.0565 (5)	0.82560 (15)	0.43458 (14)	0.0268 (5)
C1	0.1862 (7)	0.8812 (2)	0.77911 (18)	0.0198 (6)
C2	0.3877 (7)	0.81217 (18)	0.80514 (18)	0.0226 (7)
C3	0.4788 (7)	0.8053 (2)	0.89602 (18)	0.0270 (7)
H3A	0.6084	0.7592	0.9134	0.032*
C4	0.3753 (7)	0.8673 (2)	0.96024 (19)	0.0278 (8)
H4A	0.4351	0.8622	1.0213	0.033*
C5	0.1843 (7)	0.9371 (2)	0.9362 (2)	0.0247 (7)
H5A	0.1202	0.9787	0.9809	0.030*
C6	0.0881 (7)	0.94556 (19)	0.8461 (2)	0.0211 (6)
C7	−0.1173 (7)	1.02214 (19)	0.8181 (2)	0.0244 (7)
H7	−0.3147	1.0008	0.8293	0.029*
C8	−0.0888 (7)	1.0480 (2)	0.7169 (2)	0.0235 (7)
H8	−0.2352	1.0942	0.7004	0.028*
C9	−0.1250 (6)	0.96220 (19)	0.6583 (2)	0.0236 (7)
H9A	−0.3192	0.9385	0.6658	0.028*
H9B	−0.0993	0.9786	0.5940	0.028*
C10	0.0858 (6)	0.88749 (19)	0.68341 (18)	0.0193 (6)
H1	0.439 (8)	0.761 (2)	0.6908 (13)	0.049 (12)*
H2	0.228 (12)	1.1339 (18)	0.725 (3)	0.103 (19)*
H3	−0.228 (4)	1.118 (3)	0.895 (2)	0.061 (13)*
H4	0.071 (10)	0.821 (2)	0.4923 (8)	0.060 (13)*
H5	0.212 (4)	0.848 (2)	0.414 (2)	0.039 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0361 (14)	0.0245 (12)	0.0236 (11)	0.0091 (10)	−0.0056 (11)	−0.0015 (10)
O2	0.0319 (12)	0.0308 (11)	0.0215 (10)	0.0076 (11)	−0.0046 (10)	−0.0056 (9)
O3	0.0207 (11)	0.0228 (12)	0.0351 (12)	−0.0052 (10)	0.0051 (10)	−0.0006 (10)
O4	0.0180 (11)	0.0354 (13)	0.0420 (13)	0.0034 (11)	0.0007 (11)	−0.0182 (11)
O1w	0.0195 (12)	0.0378 (13)	0.0231 (11)	−0.0054 (11)	−0.0032 (10)	0.0044 (10)
C1	0.0176 (15)	0.0199 (14)	0.0220 (14)	−0.0065 (12)	0.0019 (12)	0.0013 (12)
C2	0.0261 (17)	0.0187 (15)	0.0229 (14)	−0.0045 (13)	−0.0005 (13)	−0.0019 (12)
C3	0.034 (2)	0.0230 (16)	0.0243 (15)	−0.0021 (14)	−0.0067 (14)	0.0071 (14)
C4	0.034 (2)	0.0321 (17)	0.0175 (14)	−0.0094 (15)	−0.0003 (14)	0.0024 (13)
C5	0.0224 (16)	0.0282 (17)	0.0235 (15)	−0.0068 (14)	0.0066 (14)	−0.0030 (13)
C6	0.0153 (14)	0.0246 (15)	0.0234 (15)	−0.0070 (13)	0.0052 (13)	−0.0015 (12)
C7	0.0173 (16)	0.0263 (16)	0.0298 (16)	−0.0011 (13)	0.0007 (14)	−0.0069 (14)
C8	0.0157 (14)	0.0209 (15)	0.0340 (16)	0.0029 (13)	0.0003 (13)	0.0015 (13)
C9	0.0158 (16)	0.0299 (16)	0.0252 (16)	0.0005 (13)	−0.0031 (13)	−0.0006 (13)
C10	0.0155 (14)	0.0215 (14)	0.0211 (13)	−0.0048 (13)	−0.0004 (13)	0.0016 (12)

Geometric parameters (Å, º) top

O1—C2	1.355 (3)	C3—H3A	0.9300
O1—H1	0.840 (10)	C4—C5	1.384 (4)
O2—C10	1.239 (3)	C4—H4A	0.9300
O3—C8	1.436 (4)	C5—C6	1.386 (4)
O3—H2	0.841 (10)	C5—H5A	0.9300
O4—C7	1.427 (3)	C6—C7	1.513 (4)
O4—H3	0.846 (10)	C7—C8	1.520 (4)
O1w—H4	0.842 (10)	C7—H7	0.9800
O1w—H5	0.846 (10)	C8—C9	1.508 (4)
C1—C6	1.417 (4)	C8—H8	0.9800
C1—C2	1.416 (4)	C9—C10	1.498 (4)
C1—C10	1.466 (4)	C9—H9A	0.9700
C2—C3	1.387 (4)	C9—H9B	0.9700
C3—C4	1.377 (4)

C2—O1—H1	111 (3)	O4—C7—C6	109.1 (2)
C8—O3—H2	113 (4)	O4—C7—C8	109.7 (2)
C7—O4—H3	106 (3)	C6—C7—C8	112.5 (3)
H4—O1w—H5	109 (4)	O4—C7—H7	108.5
C6—C1—C2	119.2 (2)	C6—C7—H7	108.5
C6—C1—C10	120.4 (3)	C8—C7—H7	108.5
C2—C1—C10	120.3 (2)	O3—C8—C9	106.4 (2)
O1—C2—C3	117.0 (3)	O3—C8—C7	111.0 (2)
O1—C2—C1	122.7 (2)	C9—C8—C7	109.5 (2)
C3—C2—C1	120.3 (3)	O3—C8—H8	109.9
C4—C3—C2	119.3 (3)	C9—C8—H8	109.9
C4—C3—H3A	120.3	C7—C8—H8	109.9
C2—C3—H3A	120.3	C10—C9—C8	112.2 (2)
C3—C4—C5	121.6 (3)	C10—C9—H9A	109.2
C3—C4—H4A	119.2	C8—C9—H9A	109.2
C5—C4—H4A	119.2	C10—C9—H9B	109.2
C4—C5—C6	120.5 (3)	C8—C9—H9B	109.2
C4—C5—H5A	119.8	H9A—C9—H9B	107.9
C6—C5—H5A	119.8	O2—C10—C1	120.7 (3)
C5—C6—C1	119.0 (3)	O2—C10—C9	120.5 (2)
C5—C6—C7	121.3 (3)	C1—C10—C9	118.8 (3)
C1—C6—C7	119.6 (3)

C6—C1—C2—O1	−175.8 (3)	C1—C6—C7—O4	−148.4 (3)
C10—C1—C2—O1	2.8 (4)	C5—C6—C7—C8	153.2 (3)
C6—C1—C2—C3	2.6 (4)	C1—C6—C7—C8	−26.4 (4)
C10—C1—C2—C3	−178.9 (3)	O4—C7—C8—O3	59.1 (3)
O1—C2—C3—C4	177.3 (3)	C6—C7—C8—O3	−62.5 (3)
C1—C2—C3—C4	−1.2 (4)	O4—C7—C8—C9	176.3 (2)
C2—C3—C4—C5	−0.6 (5)	C6—C7—C8—C9	54.7 (3)
C3—C4—C5—C6	1.0 (5)	O3—C8—C9—C10	63.4 (3)
C4—C5—C6—C1	0.5 (4)	C7—C8—C9—C10	−56.7 (3)
C4—C5—C6—C7	−179.1 (3)	C6—C1—C10—O2	178.9 (3)
C2—C1—C6—C5	−2.2 (4)	C2—C1—C10—O2	0.4 (4)
C10—C1—C6—C5	179.2 (3)	C6—C1—C10—C9	−0.8 (4)
C2—C1—C6—C7	177.4 (3)	C2—C1—C10—C9	−179.3 (3)
C10—C1—C6—C7	−1.1 (4)	C8—C9—C10—O2	−149.4 (3)
C5—C6—C7—O4	31.2 (4)	C8—C9—C10—C1	30.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84 (1)	1.87 (3)	2.590 (3)	143 (3)
O1—H1···O1wⁱ	0.84 (1)	2.27 (3)	2.829 (3)	124 (3)
O3—H2···O1ⁱⁱ	0.84 (1)	2.15 (3)	2.924 (3)	153 (5)
O4—H3···O1wⁱⁱⁱ	0.85 (1)	1.82 (1)	2.657 (3)	170 (4)
O1w—H4···O2	0.84 (1)	1.98 (1)	2.805 (3)	167 (4)
O1w—H5···O4^iv	0.85 (1)	1.88 (1)	2.726 (3)	177 (3)

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) −x+1, y+1/2, −z+3/2; (iii) −x−1/2, −y+2, z+1/2; (iv) −x+1/2, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀O₄·H₂O
M_r	212.20
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	4.6430 (4), 14.3904 (11), 14.4976 (10)
V (Å³)	968.65 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.31 × 0.28 × 0.24

Data collection
Diffractometer	Bruker APEX DUO diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6331, 1320, 916
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.096, 0.99
No. of reflections	1320
No. of parameters	156
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84 (1)	1.87 (3)	2.590 (3)	143 (3)
O1—H1···O1wⁱ	0.84 (1)	2.27 (3)	2.829 (3)	124 (3)
O3—H2···O1ⁱⁱ	0.84 (1)	2.15 (3)	2.924 (3)	153 (5)
O4—H3···O1wⁱⁱⁱ	0.85 (1)	1.82 (1)	2.657 (3)	170 (4)
O1w—H4···O2	0.84 (1)	1.98 (1)	2.805 (3)	167 (4)
O1w—H5···O4^iv	0.85 (1)	1.88 (1)	2.726 (3)	177 (3)

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) −x+1, y+1/2, −z+3/2; (iii) −x−1/2, −y+2, z+1/2; (iv) −x+1/2, −y+2, z−1/2.

Acknowledgements

We thank Université Mohammed V-Agdal, and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study

References

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(3R,4S)-3,4,8-Trihy­dr­oxy-1,2,3,4-tetra­hydro­naphthalen-1-one monohydrate from Embellisia eureka

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3R,4S)-3,4,8-Trihydroxy-1,2,3,4-tetrahydronaphthalen-1-one monohydrate from Embellisia eureka