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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(3R,6R,12R,20S,24S)-3,6,12-Tri­acetyl-20,24-ep­­oxy­dammarane-3,6,12,25-tetra­ol

aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China, and bSchool of Pharmacy, Yantai University, Yantai 264005, People's Republic of China
*Correspondence e-mail: mqg@ytu.edu.cn

(Received 18 November 2010; accepted 3 December 2010; online 11 December 2010)

The title compound, C36H58O8, was prepared from 20(S)-protopanaxatriol, which was degraded from Panax quinquefolium saponin with sodium in glycerine, extracted and seperated by flash chromatography. Three six-membered rings are in chair conformations, the five-membered ring is in an envelope form and the tetra­hydro­furan ring has a conformation inter­mediate between half-chair and envelope. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, and C—H⋯O contacts also occur. The absolute structure was assigned on the basis of the synthesis.

Related literature

For background to the medicinal uses of Araliaceae-type natural products, see: Shibata et al. (1985[Shibata, S., Tanaka, L., Shoji, L. & Saito, H. (1985). Econ. Med. Res. 1, 217-284.]); Takano et al. (1999[Takano, K., Midori, T., Eiichiro, I. & Teruo, M. (1999). Cancer Lett. 147, 11-16.]); Yu et al. (2007[Yu, C., Fu, F. H., Yu, X., Han, B. & Zhu, M. (2007). Arzneimittelforschung, 57, 568-572.]); Wang et al. (2010[Wang, T., Meng, Q. G., Zhang, J. F., Bi, Y. & Jiang, N. C. (2010). Fitoterapia, 81, 783-787. ]). For related structures, see: Iljin et al. (1982[Iljin, S. G., Mallnovskaya, G. V., Uvarova, N. I. & Elyakov, G. B. (1982). Tetrahedron Lett. pp. 5067-5070.]); Shi et al. (1992[Shi, Q., Hen, K., Jioka, T. & Mhiwada, Y. (1992). J. Nat. Prod. pp. 1488-1497.]).

[Scheme 1]

Experimental

Crystal data
  • C36H58O8

  • Mr = 618.82

  • Orthorhombic, P 21 21 21

  • a = 7.6936 (11) Å

  • b = 16.151 (2) Å

  • c = 28.439 (4) Å

  • V = 3533.7 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.41 × 0.20 × 0.10 mm

Data collection
  • Bruker SMART CCD diffractometer

  • 18696 measured reflections

  • 3738 independent reflections

  • 2746 reflections with I > 2σ(I)

  • Rint = 0.044

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.115

  • S = 1.04

  • 3738 reflections

  • 409 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O8i 0.82 2.36 3.050 (4) 142
C8—H8⋯O8i 0.98 2.58 3.526 (4) 161
C35—H35C⋯O6ii 0.96 2.45 3.403 (5) 172
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Both Panax ginseng and Panax quinquefolium, belonging to the Araliaceae, are well known traditional medicinal herbs. They are used as tonics and the treatment for diseases, such as tumor and myocardial ischemia. Panax ginseng contains numbers of saponins, called ginsenoside, including an oleanolic acid-type saponin in addition to the major protopanaxadiol and protopanaxatriol-type saponins (Shibata et al.,1985). Panax quinquefolium contains an ocotillol-type (20S, 24R-epoxyside) saponin with high anti-tumor activity (Takano et al.,1999), as well as oleanolic acid-type saponin, protopanaxadiol and protopanaxatriol-type saponins. (3R,6R,12R,20S,24S)-20,24-epoxy-dammarane-3,6,12,25-tetraol and (3R,6R,12R,20S,24R)-20,24-epoxy-dammarane-3,12,25-triol are found to possess cardioprotective effect on myocardial injury induced by isoproterenol in rats (Yu et al.,2007; Wang et al.,2010). As part of our ongoing investigation of ocotillol-type compound and their cardioprotective effect on myocardial injury, we report here the crystal structure of the title compound, (I).

In the molecule, all bond lengths and angles are within normal ranges (Shi et al., 1992; Iljin et al., 1982) Rings A(C11,C13,C16,C17,C18,C19), B(C13,C15,C16,C22,C32,C33), and C(C22,C24,C25,C26,C29,C32)are in chair conformations. Ring D(8,C9,C10,C11,C19) has an envelope form with C11 as the out-of-plane atom. The tetrahydrofuran ring has a conformation intermediate between half-chair and envelope forms. In the crystal, O—H···O hydrogen bonds occur.

Related literature top

For background to the medicinal uses of Araliaceae-type natural products, see: Shibata et al. (1985); Takano et al. (1999); Yu et al. (2007); Wang et al. (2010). For related structures, see: Iljin et al. (1982); Shi et al. (1992).

Experimental top

20(S)-protopanaxatriol was degraded from Panax quinquefolium saponin with sodium in glycerine at about 200°C and seperated by flash chromatography. (3R,6R,12R,20S,24S)-3,6,12-acetyl-20,24-epoxy-dammarane- 3,6,12,25-tetraol was synthesized from 20(S)-protopanaxatriol in the presence of N,N-dimethylaminopyridine, pyridine and acetic anhydride. The esters were oxidized by m-CPBA and seperated by flash chromatography. Finally, the crystals were dried at room temperature. Colourless blocks of (I) were obtained by recrystallization from ethyl acetate and petroleum ether (60–90°C) at room temperature.

Refinement top

Anomalous dispersion was negligible and Friedel pairs were merged before refinement. All H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq of the parent atoms.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
(3R,6R,12R,20S,24S)- 3,6,12-Triacetyl-20,24-epoxydammarane-3,6,12,25-tetraol top
Crystal data top
C36H58O8F(000) = 1352
Mr = 618.82Dx = 1.163 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3209 reflections
a = 7.6936 (11) Åθ = 2.5–20.5°
b = 16.151 (2) ŵ = 0.08 mm1
c = 28.439 (4) ÅT = 298 K
V = 3533.7 (9) Å3Block, colourless
Z = 40.41 × 0.20 × 0.10 mm
Data collection top
Bruker SMART CCD
diffractometer
2746 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
Graphite monochromatorθmax = 25.5°, θmin = 1.9°
ϕ and ω scansh = 99
18696 measured reflectionsk = 1916
3738 independent reflectionsl = 2534
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0618P)2 + 0.1172P]
where P = (Fo2 + 2Fc2)/3
3738 reflections(Δ/σ)max = 0.001
409 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C36H58O8V = 3533.7 (9) Å3
Mr = 618.82Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.6936 (11) ŵ = 0.08 mm1
b = 16.151 (2) ÅT = 298 K
c = 28.439 (4) Å0.41 × 0.20 × 0.10 mm
Data collection top
Bruker SMART CCD
diffractometer
2746 reflections with I > 2σ(I)
18696 measured reflectionsRint = 0.044
3738 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.04Δρmax = 0.20 e Å3
3738 reflectionsΔρmin = 0.15 e Å3
409 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
C11.1476 (7)0.7885 (3)0.68525 (15)0.1027 (16)
H1A1.20800.83850.67710.154*
H1B1.17580.74600.66290.154*
H1C1.18200.77110.71610.154*
C20.8932 (7)0.8297 (2)0.63522 (11)0.0903 (14)
H2A0.77140.84240.63580.136*
H2B0.91380.78490.61370.136*
H2C0.95730.87760.62530.136*
C30.9526 (7)0.8043 (2)0.68452 (12)0.0759 (12)
C40.8559 (5)0.7273 (2)0.69971 (11)0.0632 (9)
H40.88210.68280.67740.076*
C50.6602 (6)0.7335 (3)0.70503 (13)0.0886 (13)
H5A0.60230.69200.68600.106*
H5B0.61930.78780.69560.106*
C60.6258 (5)0.7188 (3)0.75713 (12)0.0728 (11)
H6A0.62160.77060.77430.087*
H6B0.51750.68920.76190.087*
C70.7806 (5)0.6667 (2)0.77218 (11)0.0579 (9)
C80.8360 (4)0.6771 (2)0.82373 (10)0.0491 (8)
H80.84900.73640.83040.059*
C91.0135 (4)0.6336 (2)0.83290 (12)0.0604 (9)
H9A1.06050.61140.80390.072*
H9B1.09660.67230.84610.072*
C100.9758 (4)0.5640 (2)0.86767 (11)0.0535 (8)
H10A1.07810.55070.88610.064*
H10B0.93680.51440.85150.064*
C110.8317 (4)0.59958 (17)0.89865 (10)0.0427 (7)
C120.9179 (4)0.66713 (19)0.92930 (11)0.0560 (8)
H12A1.02060.64510.94380.084*
H12B0.83790.68470.95320.084*
H12C0.94850.71360.90990.084*
C130.7242 (4)0.53600 (17)0.92850 (9)0.0397 (7)
C140.6515 (4)0.46700 (18)0.89651 (10)0.0498 (7)
H14A0.73380.45500.87210.075*
H14B0.54410.48500.88270.075*
H14C0.63150.41800.91480.075*
C150.8380 (4)0.49472 (18)0.96601 (9)0.0439 (7)
H15A0.91870.45740.95070.053*
H15B0.90550.53700.98190.053*
C160.5777 (4)0.58613 (17)0.95394 (9)0.0397 (6)
H160.64010.62900.97160.048*
C170.4668 (4)0.63455 (19)0.91841 (10)0.0483 (7)
H17A0.40070.59560.89950.058*
H17B0.38470.66890.93540.058*
C180.5747 (4)0.68930 (17)0.88586 (10)0.0457 (7)
H180.63040.73330.90420.055*
C190.7118 (4)0.63893 (18)0.86098 (9)0.0409 (7)
H190.65110.59310.84550.049*
C200.3777 (4)0.7956 (2)0.86171 (13)0.0606 (9)
C210.2781 (5)0.8289 (2)0.82093 (13)0.0793 (12)
H21A0.18060.86030.83220.119*
H21B0.23740.78390.80190.119*
H21C0.35210.86410.80250.119*
C220.4723 (4)0.53757 (17)0.99232 (9)0.0427 (7)
C230.3525 (4)0.4714 (2)0.97065 (10)0.0537 (8)
H23A0.25900.45960.99200.081*
H23B0.41780.42180.96500.081*
H23C0.30590.49160.94150.081*
C240.3551 (4)0.5997 (2)1.01821 (11)0.0567 (8)
H24A0.42400.64741.02730.068*
H24B0.26520.61870.99690.068*
C250.2702 (4)0.5633 (2)1.06176 (11)0.0612 (9)
H25A0.19950.60511.07700.073*
H25B0.19510.51771.05280.073*
C260.4069 (4)0.53286 (19)1.09541 (10)0.0526 (8)
H260.47270.58071.10690.063*
C270.3014 (5)0.5363 (3)1.17474 (12)0.0698 (10)
C280.2086 (7)0.4860 (3)1.21129 (12)0.1058 (16)
H28A0.26090.43221.21330.159*
H28B0.08850.48041.20270.159*
H28C0.21710.51331.24120.159*
C290.5362 (4)0.46892 (18)1.07605 (9)0.0454 (7)
C300.4519 (5)0.38367 (19)1.07045 (11)0.0591 (9)
H30A0.41950.36271.10080.089*
H30B0.53300.34641.05600.089*
H30C0.35020.38841.05110.089*
C310.6807 (5)0.4635 (2)1.11355 (10)0.0581 (9)
H31A0.62940.46411.14430.087*
H31B0.75770.50991.11030.087*
H31C0.74490.41301.10940.087*
C320.6090 (4)0.50400 (16)1.02858 (9)0.0398 (6)
H320.67860.55231.03750.048*
C330.7351 (4)0.44676 (16)1.00231 (9)0.0407 (7)
H330.66820.40340.98630.049*
C340.9002 (5)0.3292 (2)1.02639 (14)0.0645 (9)
C351.0098 (5)0.2951 (2)1.06456 (14)0.0847 (13)
H35A0.94490.25431.08180.127*
H35B1.04410.33891.08540.127*
H35C1.11140.26981.05130.127*
C360.7616 (6)0.5761 (2)0.75780 (12)0.0797 (12)
H36A0.74180.57270.72450.120*
H36B0.66500.55190.77420.120*
H36C0.86600.54660.76560.120*
O10.9096 (7)0.87108 (16)0.71447 (9)0.1250 (15)
H10.92420.85720.74190.188*
O20.9193 (3)0.70347 (14)0.74538 (7)0.0628 (6)
O30.4598 (3)0.72584 (12)0.85100 (7)0.0506 (5)
O40.3818 (5)0.82663 (17)0.90006 (10)0.1007 (10)
O50.8577 (3)0.40815 (12)1.03405 (6)0.0487 (5)
O60.8527 (5)0.29176 (17)0.99273 (14)0.1268 (14)
O70.3183 (3)0.49444 (14)1.13542 (7)0.0617 (6)
O80.3532 (6)0.60487 (19)1.18027 (10)0.1177 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.115 (4)0.121 (4)0.072 (3)0.054 (4)0.001 (3)0.025 (3)
C20.153 (4)0.071 (2)0.0471 (19)0.024 (3)0.007 (3)0.0122 (18)
C30.124 (4)0.061 (2)0.043 (2)0.021 (2)0.005 (2)0.0010 (16)
C40.084 (3)0.064 (2)0.0417 (18)0.008 (2)0.0018 (18)0.0070 (16)
C50.079 (3)0.128 (4)0.059 (2)0.002 (3)0.005 (2)0.017 (2)
C60.064 (2)0.108 (3)0.0461 (19)0.002 (2)0.0051 (18)0.0076 (19)
C70.058 (2)0.069 (2)0.0470 (18)0.0120 (18)0.0071 (16)0.0079 (16)
C80.0502 (18)0.0514 (18)0.0458 (17)0.0065 (16)0.0007 (15)0.0055 (14)
C90.0511 (19)0.070 (2)0.060 (2)0.0027 (18)0.0056 (16)0.0103 (17)
C100.0380 (15)0.066 (2)0.0564 (18)0.0029 (15)0.0056 (15)0.0109 (16)
C110.0368 (15)0.0464 (16)0.0449 (16)0.0026 (14)0.0012 (13)0.0029 (13)
C120.0494 (18)0.0583 (19)0.060 (2)0.0145 (16)0.0097 (17)0.0103 (15)
C130.0372 (14)0.0447 (16)0.0373 (15)0.0017 (13)0.0012 (12)0.0013 (12)
C140.0547 (17)0.0498 (17)0.0449 (16)0.0022 (16)0.0055 (15)0.0046 (14)
C150.0401 (15)0.0451 (16)0.0465 (17)0.0040 (13)0.0002 (14)0.0014 (13)
C160.0401 (15)0.0397 (15)0.0394 (15)0.0027 (13)0.0035 (13)0.0013 (12)
C170.0445 (16)0.0540 (18)0.0465 (17)0.0083 (15)0.0012 (14)0.0032 (14)
C180.0453 (16)0.0471 (17)0.0448 (16)0.0043 (14)0.0082 (14)0.0046 (13)
C190.0396 (15)0.0438 (16)0.0393 (15)0.0017 (13)0.0029 (13)0.0011 (13)
C200.060 (2)0.053 (2)0.069 (2)0.0124 (18)0.0128 (18)0.0024 (17)
C210.081 (3)0.069 (2)0.087 (3)0.024 (2)0.011 (2)0.016 (2)
C220.0408 (15)0.0469 (16)0.0403 (15)0.0018 (14)0.0019 (13)0.0021 (13)
C230.0424 (16)0.070 (2)0.0489 (18)0.0064 (17)0.0022 (15)0.0016 (16)
C240.0553 (19)0.064 (2)0.0510 (18)0.0154 (18)0.0026 (16)0.0064 (15)
C250.059 (2)0.068 (2)0.057 (2)0.0167 (18)0.0169 (17)0.0012 (17)
C260.0605 (19)0.0519 (18)0.0455 (17)0.0080 (17)0.0132 (16)0.0030 (14)
C270.080 (3)0.078 (3)0.052 (2)0.010 (2)0.0204 (19)0.0053 (19)
C280.129 (4)0.124 (4)0.065 (2)0.038 (3)0.040 (3)0.008 (2)
C290.0515 (17)0.0460 (17)0.0388 (15)0.0018 (15)0.0041 (14)0.0001 (13)
C300.071 (2)0.0522 (19)0.0540 (19)0.0110 (18)0.0091 (17)0.0003 (15)
C310.070 (2)0.061 (2)0.0425 (17)0.0027 (19)0.0006 (16)0.0040 (15)
C320.0438 (16)0.0365 (14)0.0391 (15)0.0028 (13)0.0030 (13)0.0028 (12)
C330.0394 (15)0.0418 (16)0.0409 (16)0.0024 (13)0.0037 (13)0.0024 (13)
C340.053 (2)0.049 (2)0.092 (3)0.0138 (17)0.001 (2)0.0021 (19)
C350.067 (2)0.071 (2)0.116 (3)0.022 (2)0.011 (2)0.042 (2)
C360.102 (3)0.082 (3)0.055 (2)0.027 (3)0.016 (2)0.0087 (19)
O10.247 (5)0.0678 (17)0.0601 (16)0.010 (3)0.016 (3)0.0145 (13)
O20.0642 (14)0.0761 (15)0.0481 (12)0.0093 (13)0.0046 (12)0.0153 (11)
O30.0531 (12)0.0510 (12)0.0478 (12)0.0099 (11)0.0038 (10)0.0040 (9)
O40.125 (2)0.0804 (18)0.097 (2)0.0432 (18)0.036 (2)0.0276 (17)
O50.0498 (12)0.0464 (12)0.0500 (12)0.0058 (10)0.0068 (10)0.0058 (9)
O60.136 (3)0.076 (2)0.168 (3)0.047 (2)0.066 (3)0.054 (2)
O70.0776 (15)0.0617 (14)0.0458 (12)0.0106 (12)0.0191 (12)0.0055 (10)
O80.186 (3)0.089 (2)0.0789 (19)0.046 (3)0.064 (2)0.0343 (16)
Geometric parameters (Å, º) top
C1—C31.522 (7)C18—C191.509 (4)
C1—H1A0.9600C18—H180.9800
C1—H1B0.9600C19—H190.9800
C1—H1C0.9600C20—O41.201 (4)
C2—C31.531 (5)C20—O31.327 (4)
C2—H2A0.9600C20—C211.491 (5)
C2—H2B0.9600C21—H21A0.9600
C2—H2C0.9600C21—H21B0.9600
C3—O11.414 (5)C21—H21C0.9600
C3—C41.511 (5)C22—C241.537 (4)
C4—O21.440 (4)C22—C231.540 (4)
C4—C51.516 (6)C22—C321.570 (4)
C4—H40.9800C23—H23A0.9600
C5—C61.524 (5)C23—H23B0.9600
C5—H5A0.9700C23—H23C0.9600
C5—H5B0.9700C24—C251.519 (4)
C6—C71.520 (5)C24—H24A0.9700
C6—H6A0.9700C24—H24B0.9700
C6—H6B0.9700C25—C261.504 (4)
C7—O21.439 (4)C25—H25A0.9700
C7—C361.527 (5)C25—H25B0.9700
C7—C81.536 (4)C26—O71.464 (3)
C8—C191.554 (4)C26—C291.536 (4)
C8—C91.558 (5)C26—H260.9800
C8—H80.9800C27—O81.187 (4)
C9—C101.525 (4)C27—O71.313 (4)
C9—H9A0.9700C27—C281.500 (5)
C9—H9B0.9700C28—H28A0.9600
C10—C111.529 (4)C28—H28B0.9600
C10—H10A0.9700C28—H28C0.9600
C10—H10B0.9700C29—C301.531 (4)
C11—C121.546 (4)C29—C311.543 (4)
C11—C191.550 (4)C29—C321.567 (4)
C11—C131.568 (4)C30—H30A0.9600
C12—H12A0.9600C30—H30B0.9600
C12—H12B0.9600C30—H30C0.9600
C12—H12C0.9600C31—H31A0.9600
C13—C151.532 (4)C31—H31B0.9600
C13—C141.543 (4)C31—H31C0.9600
C13—C161.565 (4)C32—C331.534 (4)
C14—H14A0.9600C32—H320.9800
C14—H14B0.9600C33—O51.447 (3)
C14—H14C0.9600C33—H330.9800
C15—C331.514 (4)C34—O61.190 (4)
C15—H15A0.9700C34—O51.334 (4)
C15—H15B0.9700C34—C351.481 (5)
C16—C171.537 (4)C35—H35A0.9600
C16—C221.570 (4)C35—H35B0.9600
C16—H160.9800C35—H35C0.9600
C17—C181.526 (4)C36—H36A0.9600
C17—H17A0.9700C36—H36B0.9600
C17—H17B0.9700C36—H36C0.9600
C18—O31.453 (3)O1—H10.8200
C3—C1—H1A109.5C19—C18—H18109.6
C3—C1—H1B109.5C17—C18—H18109.6
H1A—C1—H1B109.5C18—C19—C11108.2 (2)
C3—C1—H1C109.5C18—C19—C8122.4 (3)
H1A—C1—H1C109.5C11—C19—C8105.5 (2)
H1B—C1—H1C109.5C18—C19—H19106.6
C3—C2—H2A109.5C11—C19—H19106.6
C3—C2—H2B109.5C8—C19—H19106.6
H2A—C2—H2B109.5O4—C20—O3123.4 (3)
C3—C2—H2C109.5O4—C20—C21124.7 (3)
H2A—C2—H2C109.5O3—C20—C21111.9 (3)
H2B—C2—H2C109.5C20—C21—H21A109.5
O1—C3—C4109.9 (3)C20—C21—H21B109.5
O1—C3—C1110.5 (4)H21A—C21—H21B109.5
C4—C3—C1110.1 (4)C20—C21—H21C109.5
O1—C3—C2106.1 (3)H21A—C21—H21C109.5
C4—C3—C2109.6 (3)H21B—C21—H21C109.5
C1—C3—C2110.6 (4)C24—C22—C23107.1 (2)
O2—C4—C3108.1 (3)C24—C22—C32107.7 (2)
O2—C4—C5105.3 (3)C23—C22—C32115.1 (2)
C3—C4—C5117.6 (4)C24—C22—C16108.1 (2)
O2—C4—H4108.5C23—C22—C16112.2 (2)
C3—C4—H4108.5C32—C22—C16106.5 (2)
C5—C4—H4108.5C22—C23—H23A109.5
C4—C5—C6105.0 (3)C22—C23—H23B109.5
C4—C5—H5A110.7H23A—C23—H23B109.5
C6—C5—H5A110.7C22—C23—H23C109.5
C4—C5—H5B110.7H23A—C23—H23C109.5
C6—C5—H5B110.7H23B—C23—H23C109.5
H5A—C5—H5B108.8C25—C24—C22113.0 (3)
C7—C6—C5103.0 (3)C25—C24—H24A109.0
C7—C6—H6A111.2C22—C24—H24A109.0
C5—C6—H6A111.2C25—C24—H24B109.0
C7—C6—H6B111.2C22—C24—H24B109.0
C5—C6—H6B111.2H24A—C24—H24B107.8
H6A—C6—H6B109.1C26—C25—C24110.2 (3)
O2—C7—C6101.8 (2)C26—C25—H25A109.6
O2—C7—C36108.9 (3)C24—C25—H25A109.6
C6—C7—C36112.3 (3)C26—C25—H25B109.6
O2—C7—C8104.7 (3)C24—C25—H25B109.6
C6—C7—C8115.2 (3)H25A—C25—H25B108.1
C36—C7—C8112.8 (3)O7—C26—C25107.9 (3)
C7—C8—C19115.9 (3)O7—C26—C29107.2 (2)
C7—C8—C9110.7 (3)C25—C26—C29116.4 (2)
C19—C8—C9104.2 (2)O7—C26—H26108.4
C7—C8—H8108.6C25—C26—H26108.4
C19—C8—H8108.6C29—C26—H26108.4
C9—C8—H8108.6O8—C27—O7124.0 (3)
C10—C9—C8105.9 (3)O8—C27—C28125.0 (3)
C10—C9—H9A110.5O7—C27—C28111.0 (4)
C8—C9—H9A110.5C27—C28—H28A109.5
C10—C9—H9B110.5C27—C28—H28B109.5
C8—C9—H9B110.5H28A—C28—H28B109.5
H9A—C9—H9B108.7C27—C28—H28C109.5
C9—C10—C11103.5 (3)H28A—C28—H28C109.5
C9—C10—H10A111.1H28B—C28—H28C109.5
C11—C10—H10A111.1C30—C29—C26111.6 (2)
C9—C10—H10B111.1C30—C29—C31109.0 (2)
C11—C10—H10B111.1C26—C29—C31104.9 (2)
H10A—C10—H10B109.0C30—C29—C32112.8 (2)
C10—C11—C12106.2 (2)C26—C29—C32107.3 (2)
C10—C11—C19100.8 (2)C31—C29—C32111.0 (2)
C12—C11—C19110.8 (2)C29—C30—H30A109.5
C10—C11—C13116.6 (2)C29—C30—H30B109.5
C12—C11—C13112.5 (2)H30A—C30—H30B109.5
C19—C11—C13109.2 (2)C29—C30—H30C109.5
C11—C12—H12A109.5H30A—C30—H30C109.5
C11—C12—H12B109.5H30B—C30—H30C109.5
H12A—C12—H12B109.5C29—C31—H31A109.5
C11—C12—H12C109.5C29—C31—H31B109.5
H12A—C12—H12C109.5H31A—C31—H31B109.5
H12B—C12—H12C109.5C29—C31—H31C109.5
C15—C13—C14107.6 (2)H31A—C31—H31C109.5
C15—C13—C16108.3 (2)H31B—C31—H31C109.5
C14—C13—C16112.7 (2)C33—C32—C29115.3 (2)
C15—C13—C11111.1 (2)C33—C32—C22108.2 (2)
C14—C13—C11110.2 (2)C29—C32—C22116.8 (2)
C16—C13—C11106.9 (2)C33—C32—H32105.1
C13—C14—H14A109.5C29—C32—H32105.1
C13—C14—H14B109.5C22—C32—H32105.1
H14A—C14—H14B109.5O5—C33—C15107.8 (2)
C13—C14—H14C109.5O5—C33—C32111.6 (2)
H14A—C14—H14C109.5C15—C33—C32110.8 (2)
H14B—C14—H14C109.5O5—C33—H33108.9
C33—C15—C13113.5 (2)C15—C33—H33108.9
C33—C15—H15A108.9C32—C33—H33108.9
C13—C15—H15A108.9O6—C34—O5122.8 (3)
C33—C15—H15B108.9O6—C34—C35125.1 (4)
C13—C15—H15B108.9O5—C34—C35112.1 (3)
H15A—C15—H15B107.7C34—C35—H35A109.5
C17—C16—C13111.1 (2)C34—C35—H35B109.5
C17—C16—C22115.1 (2)H35A—C35—H35B109.5
C13—C16—C22115.8 (2)C34—C35—H35C109.5
C17—C16—H16104.4H35A—C35—H35C109.5
C13—C16—H16104.4H35B—C35—H35C109.5
C22—C16—H16104.4C7—C36—H36A109.5
C18—C17—C16113.1 (2)C7—C36—H36B109.5
C18—C17—H17A109.0H36A—C36—H36B109.5
C16—C17—H17A109.0C7—C36—H36C109.5
C18—C17—H17B109.0H36A—C36—H36C109.5
C16—C17—H17B109.0H36B—C36—H36C109.5
H17A—C17—H17B107.8C3—O1—H1109.5
O3—C18—C19108.9 (2)C7—O2—C4109.6 (2)
O3—C18—C17108.6 (2)C20—O3—C18118.5 (2)
C19—C18—C17110.6 (2)C34—O5—C33118.0 (2)
O3—C18—H18109.6C27—O7—C26119.3 (3)
O1—C3—C4—O265.8 (4)C9—C8—C19—C18142.2 (3)
C1—C3—C4—O256.1 (4)C7—C8—C19—C11139.9 (3)
C2—C3—C4—O2177.9 (3)C9—C8—C19—C1118.0 (3)
O1—C3—C4—C553.1 (5)C17—C16—C22—C2456.5 (3)
C1—C3—C4—C5175.1 (4)C13—C16—C22—C24171.6 (2)
C2—C3—C4—C563.1 (5)C17—C16—C22—C2361.3 (3)
O2—C4—C5—C64.7 (4)C13—C16—C22—C2370.6 (3)
C3—C4—C5—C6115.7 (4)C17—C16—C22—C32172.0 (2)
C4—C5—C6—C726.2 (4)C13—C16—C22—C3256.2 (3)
C5—C6—C7—O237.8 (4)C23—C22—C24—C2569.1 (3)
C5—C6—C7—C3678.5 (4)C32—C22—C24—C2555.2 (3)
C5—C6—C7—C8150.5 (3)C16—C22—C24—C25169.9 (3)
O2—C7—C8—C19177.4 (3)C22—C24—C25—C2658.4 (4)
C6—C7—C8—C1971.7 (4)C24—C25—C26—O7177.0 (3)
C36—C7—C8—C1959.1 (4)C24—C25—C26—C2956.5 (4)
O2—C7—C8—C959.1 (3)O7—C26—C29—C3047.0 (3)
C6—C7—C8—C9170.0 (3)C25—C26—C29—C3073.8 (3)
C36—C7—C8—C959.3 (4)O7—C26—C29—C3170.9 (3)
C7—C8—C9—C10115.6 (3)C25—C26—C29—C31168.3 (3)
C19—C8—C9—C109.7 (3)O7—C26—C29—C32170.9 (2)
C8—C9—C10—C1134.2 (3)C25—C26—C29—C3250.1 (3)
C9—C10—C11—C1271.1 (3)C30—C29—C32—C3354.0 (3)
C9—C10—C11—C1944.5 (3)C26—C29—C32—C33177.2 (2)
C9—C10—C11—C13162.5 (2)C31—C29—C32—C3368.7 (3)
C10—C11—C13—C1566.1 (3)C30—C29—C32—C2274.7 (3)
C12—C11—C13—C1557.1 (3)C26—C29—C32—C2248.5 (3)
C19—C11—C13—C15179.4 (2)C31—C29—C32—C22162.5 (2)
C10—C11—C13—C1453.1 (3)C24—C22—C32—C33175.9 (2)
C12—C11—C13—C14176.3 (2)C23—C22—C32—C3364.8 (3)
C19—C11—C13—C1460.2 (3)C16—C22—C32—C3360.2 (3)
C10—C11—C13—C16175.9 (2)C24—C22—C32—C2952.0 (3)
C12—C11—C13—C1661.0 (3)C23—C22—C32—C2967.3 (3)
C19—C11—C13—C1662.5 (3)C16—C22—C32—C29167.7 (2)
C14—C13—C15—C3371.5 (3)C13—C15—C33—O5177.4 (2)
C16—C13—C15—C3350.6 (3)C13—C15—C33—C3260.3 (3)
C11—C13—C15—C33167.8 (2)C29—C32—C33—O542.7 (3)
C15—C13—C16—C17175.7 (2)C22—C32—C33—O5175.6 (2)
C14—C13—C16—C1765.3 (3)C29—C32—C33—C15162.8 (2)
C11—C13—C16—C1755.9 (3)C22—C32—C33—C1564.3 (3)
C15—C13—C16—C2250.6 (3)C6—C7—O2—C437.0 (3)
C14—C13—C16—C2268.4 (3)C36—C7—O2—C481.8 (3)
C11—C13—C16—C22170.4 (2)C8—C7—O2—C4157.3 (3)
C13—C16—C17—C1853.3 (3)C3—C4—O2—C7147.0 (3)
C22—C16—C17—C18172.6 (2)C5—C4—O2—C720.5 (4)
C16—C17—C18—O3174.6 (2)O4—C20—O3—C186.4 (5)
C16—C17—C18—C1955.1 (3)C21—C20—O3—C18174.9 (3)
O3—C18—C19—C11179.3 (2)C19—C18—O3—C20153.5 (3)
C17—C18—C19—C1160.1 (3)C17—C18—O3—C2086.0 (3)
O3—C18—C19—C857.8 (3)O6—C34—O5—C336.2 (5)
C17—C18—C19—C8177.0 (3)C35—C34—O5—C33173.2 (3)
C10—C11—C19—C18171.2 (2)C15—C33—O5—C3497.3 (3)
C12—C11—C19—C1859.0 (3)C32—C33—O5—C34140.9 (3)
C13—C11—C19—C1865.5 (3)O8—C27—O7—C260.4 (6)
C10—C11—C19—C838.6 (3)C28—C27—O7—C26179.6 (3)
C12—C11—C19—C873.6 (3)C25—C26—O7—C27100.7 (4)
C13—C11—C19—C8161.9 (2)C29—C26—O7—C27133.3 (3)
C7—C8—C19—C1896.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O8i0.822.363.050 (4)142
C8—H8···O8i0.982.583.526 (4)161
C35—H35C···O6ii0.962.453.403 (5)172
Symmetry codes: (i) x+1/2, y+3/2, z+2; (ii) x+1/2, y+1/2, z+2.

Experimental details

Crystal data
Chemical formulaC36H58O8
Mr618.82
Crystal system, space groupOrthorhombic, P212121
Temperature (K)298
a, b, c (Å)7.6936 (11), 16.151 (2), 28.439 (4)
V3)3533.7 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.41 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
18696, 3738, 2746
Rint0.044
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.115, 1.04
No. of reflections3738
No. of parameters409
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.15

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O8i0.822.363.050 (4)142
C8—H8···O8i0.982.583.526 (4)161
C35—H35C···O6ii0.962.453.403 (5)172
Symmetry codes: (i) x+1/2, y+3/2, z+2; (ii) x+1/2, y+1/2, z+2.
 

Acknowledgements

The authors thank Mr. Lian-dong Liu (College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University) for his invaluable support with the X-ray data collection. The authors would like to thank Shandong Provincial Natural Science Foundation, China (Y2007C138), and the Scientific Reasearch Foundation of the Higher Education Institutions of Shandong Province and China (J07WE26) for a research grant.

References

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationIljin, S. G., Mallnovskaya, G. V., Uvarova, N. I. & Elyakov, G. B. (1982). Tetrahedron Lett. pp. 5067–5070.  CSD CrossRef Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationShi, Q., Hen, K., Jioka, T. & Mhiwada, Y. (1992). J. Nat. Prod. pp. 1488–1497.  CSD CrossRef Web of Science
First citationShibata, S., Tanaka, L., Shoji, L. & Saito, H. (1985). Econ. Med. Res. 1, 217–284.
First citationTakano, K., Midori, T., Eiichiro, I. & Teruo, M. (1999). Cancer Lett. 147, 11–16.  Web of Science PubMed
First citationWang, T., Meng, Q. G., Zhang, J. F., Bi, Y. & Jiang, N. C. (2010). Fitoterapia, 81, 783–787.   Web of Science CrossRef CAS PubMed
First citationYu, C., Fu, F. H., Yu, X., Han, B. & Zhu, M. (2007). Arzneimittelforschung, 57, 568–572.  Web of Science PubMed CAS

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