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

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ISSN: 2056-9890

Oosporein from Tremella fuciformis

aMaize Research Institute, Sichuan Agricultural University, Chengdu 611130, People's Republic of China, and bThe Key Laboratory of Medicinal and Edible Plants Resources Development of Sichuan Education Commission, Chengdu University, Chengdu 610106, People's Republic of China
*Correspondence e-mail: lwc0011@yahoo.cn

(Received 16 March 2012; accepted 24 March 2012; online 31 March 2012)

The title compound [systematic name: 3,3′,6,6′-tetra­hydroxy-4,4′-dimethyl-1,1′-bi(cyclo­hexa-3,6-diene)-2,2′,5,5′-tetra­one], C14H10O8, was isolated from Tremella fuciformis. The mol­ecule has 2 symmetry, with the mid-point of the C—C bond linking the cyclo­hexa­dienedione rings located on a twofold rotation axis. In the mol­ecule, the ring is approximately planar, with an r.m.s. deviation of 0.0093 Å, and the two rings make a dihedral angle of 67.89 (5)°. Inter­molecular O—H⋯O hydrogen bonding occurs in the crystal structure.

Related literature

For general background to the title compound, see: Takeshita & Anchel (1965[Takeshita, H. & Anchel, M. (1965). Science, 147, 152-153.]). For the chemical structure of the title compound established from NMR data, see: Richard et al. (1974[Richard, J. C., Jerry, W. K., Horace, G. C. & Elemer, E. D. (1974). J. Agric. Food Chem, 22, 517-520.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10O8

  • Mr = 306.22

  • Monoclinic, C 2/c

  • a = 11.9983 (9) Å

  • b = 8.2981 (6) Å

  • c = 13.7634 (11) Å

  • β = 105.994 (7)°

  • V = 1317.28 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 293 K

  • 0.25 × 0.20 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • 2848 measured reflections

  • 1342 independent reflections

  • 937 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.118

  • S = 1.06

  • 1342 reflections

  • 103 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O4i 0.82 2.03 2.770 (2) 150
O3—H3⋯O1ii 0.82 2.03 2.7658 (19) 150
Symmetry codes: (i) [x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (ii) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The oosporein was previously isolated from Phlebia mellea (Takeshita & Anchel, 1965), and its structure was established from the spectroscopic data (Richard et al., 1974). In our recent investigation, it was isolated from Tremella fuciformis for the first time, and its structure is reported here.

The molecular structure of the title compound is shown in Fig. 1. The molecule of the title compound contains two plane six-membered rings which assumes a screw-plane conformation, and there is a dihedral angle between the two planes.

The crystal structure contains intermolecular O—H···O hydrogen bonding between the hydroxy group and the aldehyde atom (Table 1).

Related literature top

For general background to the title compound, see: Takeshita & Anchel (1965). For the chemical structure of the title compound established from NMR data, see: Richard et al. (1974).

Experimental top

Tremella fuciformis was a culture collection of our laboratory, the stock culture was maintained on potato dextrose agar (PDA) slants and subcultured once a month. It was used in submerged culture. Agar, slants containing potato–dextrose–agar were inoculated with mycelia and incubated at 25 °C for 5 days, and then used as inoculums for seed culture. The seed culture was grown in 250 ml shake flasks containing 50 ml for 2 days at initial pH 6.8–7.0, 25 °C, and 150 rpm with a medium containing 20 g.l-1 glucose, 2 g.l-1 soybean meal leaching solution, 1.0 g.l-1 MgSO4, 1.0 g.l-1 KH2PO4 and 0.46 g.l-1 K2HPO4. Submerged fermentation was the same as the seed culture medium. All media were sterilized at 115 °C for 20 min. Fermentation liquid centrifugal (10000 rpm) and then rotary evaporation at 50 °C. Fermented liquid was concentrated by rotating evaporation at 50°C and add 4 times the volume of the anhydrous alcohol, 4 °C for the night precipitation, 10000 rmp centrifugal remove polysaccharides and protein. Rotated evaporation and concentration, concentrate on D101 macroporous resin adsorption, first washed with distilled water, then elution with 95% ethanol elution, eluent was saved at 4°C, to obtain crud crystals, crud crystals washing was 95% ethanol, and then recrystallized in 95% ethanol solution.

Refinement top

H atoms were located geometrically with O—H = 0.82 Å and C—H = 0.96 Å, and using a riding model with Uiso(H) = 1.5Ueq(C,O).

Structure description top

The oosporein was previously isolated from Phlebia mellea (Takeshita & Anchel, 1965), and its structure was established from the spectroscopic data (Richard et al., 1974). In our recent investigation, it was isolated from Tremella fuciformis for the first time, and its structure is reported here.

The molecular structure of the title compound is shown in Fig. 1. The molecule of the title compound contains two plane six-membered rings which assumes a screw-plane conformation, and there is a dihedral angle between the two planes.

The crystal structure contains intermolecular O—H···O hydrogen bonding between the hydroxy group and the aldehyde atom (Table 1).

For general background to the title compound, see: Takeshita & Anchel (1965). For the chemical structure of the title compound established from NMR data, see: Richard et al. (1974).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids for non-H atoms.
3,3',6,6'-tetrahydroxy-4,4'-dimethyl-1,1'-bi(cyclohexa-3,6-diene)-2,2',5,5'- tetraone top
Crystal data top
C14H10O8F(000) = 632
Mr = 306.22Dx = 1.544 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 11.9983 (9) ÅCell parameters from 884 reflections
b = 8.2981 (6) Åθ = 3.0–28.7°
c = 13.7634 (11) ŵ = 0.13 mm1
β = 105.994 (7)°T = 293 K
V = 1317.28 (17) Å3Block, colorless
Z = 40.25 × 0.20 × 0.20 mm
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
937 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 26.4°, θmin = 3.0°
Detector resolution: 10.0 pixels mm-1h = 1411
ω scansk = 910
2848 measured reflectionsl = 1713
1342 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0491P)2 + 0.4579P]
where P = (Fo2 + 2Fc2)/3
1342 reflections(Δ/σ)max < 0.001
103 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C14H10O8V = 1317.28 (17) Å3
Mr = 306.22Z = 4
Monoclinic, C2/cMo Kα radiation
a = 11.9983 (9) ŵ = 0.13 mm1
b = 8.2981 (6) ÅT = 293 K
c = 13.7634 (11) Å0.25 × 0.20 × 0.20 mm
β = 105.994 (7)°
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
937 reflections with I > 2σ(I)
2848 measured reflectionsRint = 0.022
1342 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.06Δρmax = 0.21 e Å3
1342 reflectionsΔρmin = 0.17 e Å3
103 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.82546 (12)0.06885 (18)0.65807 (11)0.0380 (4)
O20.79548 (13)0.0605 (2)0.45935 (11)0.0434 (5)
H20.76230.01350.49580.065*
O31.16014 (12)0.3820 (2)0.71051 (11)0.0402 (5)
H31.19650.42290.67440.060*
O41.12577 (13)0.3814 (2)0.51152 (12)0.0454 (5)
C10.95888 (17)0.2202 (2)0.47435 (15)0.0275 (5)
C20.88498 (16)0.1437 (2)0.51643 (15)0.0274 (5)
C30.89706 (16)0.1438 (2)0.62776 (15)0.0259 (5)
C40.99324 (15)0.2298 (2)0.69505 (14)0.0232 (5)
C51.06929 (16)0.3034 (2)0.65361 (15)0.0267 (5)
C61.05442 (17)0.3056 (2)0.54165 (16)0.0284 (5)
C70.9473 (2)0.2204 (3)0.36334 (16)0.0399 (6)
H7A0.90640.12540.33320.060*
H7B1.02290.22150.35250.060*
H7C0.90500.31440.33310.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0323 (8)0.0499 (10)0.0336 (9)0.0172 (7)0.0120 (7)0.0003 (7)
O20.0398 (9)0.0616 (12)0.0274 (9)0.0259 (8)0.0069 (7)0.0044 (8)
O30.0339 (9)0.0544 (11)0.0309 (9)0.0219 (7)0.0066 (7)0.0014 (8)
O40.0416 (9)0.0618 (11)0.0351 (10)0.0259 (8)0.0146 (7)0.0008 (8)
C10.0264 (10)0.0320 (12)0.0243 (11)0.0007 (9)0.0074 (8)0.0006 (9)
C20.0236 (10)0.0315 (12)0.0259 (12)0.0045 (9)0.0047 (8)0.0013 (9)
C30.0227 (10)0.0269 (11)0.0286 (12)0.0003 (8)0.0080 (8)0.0034 (8)
C40.0223 (10)0.0247 (11)0.0227 (11)0.0019 (8)0.0064 (8)0.0009 (8)
C50.0220 (10)0.0289 (11)0.0274 (12)0.0033 (8)0.0040 (8)0.0019 (9)
C60.0260 (11)0.0299 (12)0.0313 (12)0.0024 (9)0.0112 (9)0.0018 (9)
C70.0424 (13)0.0499 (15)0.0291 (13)0.0063 (11)0.0125 (10)0.0024 (11)
Geometric parameters (Å, º) top
O1—C31.223 (2)C2—C31.499 (3)
O2—C21.335 (2)C3—C41.452 (3)
O2—H20.8200C4—C51.348 (3)
O3—C51.325 (2)C4—C4i1.476 (4)
O3—H30.8200C5—C61.502 (3)
O4—C61.223 (2)C7—H7A0.9600
C1—C21.344 (3)C7—H7B0.9600
C1—C61.445 (3)C7—H7C0.9600
C1—C71.496 (3)
C2—O2—H2109.5C3—C4—C4i119.81 (18)
C5—O3—H3109.5O3—C5—C4121.01 (18)
C2—C1—C6117.14 (18)O3—C5—C6116.50 (17)
C2—C1—C7123.62 (18)C4—C5—C6122.46 (17)
C6—C1—C7119.24 (18)O4—C6—C1122.71 (19)
O2—C2—C1120.65 (18)O4—C6—C5117.24 (18)
O2—C2—C3115.94 (16)C1—C6—C5120.04 (17)
C1—C2—C3123.41 (17)C1—C7—H7A109.5
O1—C3—C4122.79 (19)C1—C7—H7B109.5
O1—C3—C2117.97 (17)H7A—C7—H7B109.5
C4—C3—C2119.23 (17)C1—C7—H7C109.5
C5—C4—C3117.65 (18)H7A—C7—H7C109.5
C5—C4—C4i122.51 (19)H7B—C7—H7C109.5
Symmetry code: (i) x+2, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O4ii0.822.032.770 (2)150
O3—H3···O1iii0.822.032.7658 (19)150
Symmetry codes: (ii) x1/2, y1/2, z; (iii) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC14H10O8
Mr306.22
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)11.9983 (9), 8.2981 (6), 13.7634 (11)
β (°) 105.994 (7)
V3)1317.28 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.25 × 0.20 × 0.20
Data collection
DiffractometerOxford Diffraction Xcalibur Eos
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2848, 1342, 937
Rint0.022
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.118, 1.06
No. of reflections1342
No. of parameters103
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.17

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O4i0.822.032.770 (2)149.7
O3—H3···O1ii0.822.032.7658 (19)149.9
Symmetry codes: (i) x1/2, y1/2, z; (ii) x+1/2, y+1/2, z.
 

Acknowledgements

This project was supported by the Chengdu University Research Fund (No. 2010XJZ23).

References

First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
First citationRichard, J. C., Jerry, W. K., Horace, G. C. & Elemer, E. D. (1974). J. Agric. Food Chem, 22, 517–520.  PubMed Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTakeshita, H. & Anchel, M. (1965). Science, 147, 152–153.  CrossRef PubMed CAS Web of Science Google Scholar

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ISSN: 2056-9890
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