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organic compounds
(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
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 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 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); 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
Crystal data
|
Data collection
|
Refinement
|
|
Data collection: SMART (Bruker, 1997); cell SAINT (Bruker, 1997
); 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: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536810050749/hb5749sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050749/hb5749Isup2.hkl
20(S)-protopanaxatriol was degraded from Panax quinquefolium saponin with sodium in glycerine at about 200°C and seperated by flash
(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 were oxidized by m-CPBA and seperated by flash 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.Anomalous dispersion was negligible and Friedel pairs were merged before
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.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
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.
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).
Data collection: SMART (Bruker, 1997); cell
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). ![]() | Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. |
C36H58O8 | F(000) = 1352 |
Mr = 618.82 | Dx = 1.163 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3209 reflections |
a = 7.6936 (11) Å | θ = 2.5–20.5° |
b = 16.151 (2) Å | µ = 0.08 mm−1 |
c = 28.439 (4) Å | T = 298 K |
V = 3533.7 (9) Å3 | Block, colourless |
Z = 4 | 0.41 × 0.20 × 0.10 mm |
Bruker SMART CCD diffractometer | 2746 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.044 |
Graphite monochromator | θmax = 25.5°, θmin = 1.9° |
φ and ω scans | h = −9→9 |
18696 measured reflections | k = −19→16 |
3738 independent reflections | l = −25→34 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-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 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C36H58O8 | V = 3533.7 (9) Å3 |
Mr = 618.82 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.6936 (11) Å | µ = 0.08 mm−1 |
b = 16.151 (2) Å | T = 298 K |
c = 28.439 (4) Å | 0.41 × 0.20 × 0.10 mm |
Bruker SMART CCD diffractometer | 2746 reflections with I > 2σ(I) |
18696 measured reflections | Rint = 0.044 |
3738 independent reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.20 e Å−3 |
3738 reflections | Δρmin = −0.15 e Å−3 |
409 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.1476 (7) | 0.7885 (3) | 0.68525 (15) | 0.1027 (16) | |
H1A | 1.2080 | 0.8385 | 0.6771 | 0.154* | |
H1B | 1.1758 | 0.7460 | 0.6629 | 0.154* | |
H1C | 1.1820 | 0.7711 | 0.7161 | 0.154* | |
C2 | 0.8932 (7) | 0.8297 (2) | 0.63522 (11) | 0.0903 (14) | |
H2A | 0.7714 | 0.8424 | 0.6358 | 0.136* | |
H2B | 0.9138 | 0.7849 | 0.6137 | 0.136* | |
H2C | 0.9573 | 0.8776 | 0.6253 | 0.136* | |
C3 | 0.9526 (7) | 0.8043 (2) | 0.68452 (12) | 0.0759 (12) | |
C4 | 0.8559 (5) | 0.7273 (2) | 0.69971 (11) | 0.0632 (9) | |
H4 | 0.8821 | 0.6828 | 0.6774 | 0.076* | |
C5 | 0.6602 (6) | 0.7335 (3) | 0.70503 (13) | 0.0886 (13) | |
H5A | 0.6023 | 0.6920 | 0.6860 | 0.106* | |
H5B | 0.6193 | 0.7878 | 0.6956 | 0.106* | |
C6 | 0.6258 (5) | 0.7188 (3) | 0.75713 (12) | 0.0728 (11) | |
H6A | 0.6216 | 0.7706 | 0.7743 | 0.087* | |
H6B | 0.5175 | 0.6892 | 0.7619 | 0.087* | |
C7 | 0.7806 (5) | 0.6667 (2) | 0.77218 (11) | 0.0579 (9) | |
C8 | 0.8360 (4) | 0.6771 (2) | 0.82373 (10) | 0.0491 (8) | |
H8 | 0.8490 | 0.7364 | 0.8304 | 0.059* | |
C9 | 1.0135 (4) | 0.6336 (2) | 0.83290 (12) | 0.0604 (9) | |
H9A | 1.0605 | 0.6114 | 0.8039 | 0.072* | |
H9B | 1.0966 | 0.6723 | 0.8461 | 0.072* | |
C10 | 0.9758 (4) | 0.5640 (2) | 0.86767 (11) | 0.0535 (8) | |
H10A | 1.0781 | 0.5507 | 0.8861 | 0.064* | |
H10B | 0.9368 | 0.5144 | 0.8515 | 0.064* | |
C11 | 0.8317 (4) | 0.59958 (17) | 0.89865 (10) | 0.0427 (7) | |
C12 | 0.9179 (4) | 0.66713 (19) | 0.92930 (11) | 0.0560 (8) | |
H12A | 1.0206 | 0.6451 | 0.9438 | 0.084* | |
H12B | 0.8379 | 0.6847 | 0.9532 | 0.084* | |
H12C | 0.9485 | 0.7136 | 0.9099 | 0.084* | |
C13 | 0.7242 (4) | 0.53600 (17) | 0.92850 (9) | 0.0397 (7) | |
C14 | 0.6515 (4) | 0.46700 (18) | 0.89651 (10) | 0.0498 (7) | |
H14A | 0.7338 | 0.4550 | 0.8721 | 0.075* | |
H14B | 0.5441 | 0.4850 | 0.8827 | 0.075* | |
H14C | 0.6315 | 0.4180 | 0.9148 | 0.075* | |
C15 | 0.8380 (4) | 0.49472 (18) | 0.96601 (9) | 0.0439 (7) | |
H15A | 0.9187 | 0.4574 | 0.9507 | 0.053* | |
H15B | 0.9055 | 0.5370 | 0.9819 | 0.053* | |
C16 | 0.5777 (4) | 0.58613 (17) | 0.95394 (9) | 0.0397 (6) | |
H16 | 0.6401 | 0.6290 | 0.9716 | 0.048* | |
C17 | 0.4668 (4) | 0.63455 (19) | 0.91841 (10) | 0.0483 (7) | |
H17A | 0.4007 | 0.5956 | 0.8995 | 0.058* | |
H17B | 0.3847 | 0.6689 | 0.9354 | 0.058* | |
C18 | 0.5747 (4) | 0.68930 (17) | 0.88586 (10) | 0.0457 (7) | |
H18 | 0.6304 | 0.7333 | 0.9042 | 0.055* | |
C19 | 0.7118 (4) | 0.63893 (18) | 0.86098 (9) | 0.0409 (7) | |
H19 | 0.6511 | 0.5931 | 0.8455 | 0.049* | |
C20 | 0.3777 (4) | 0.7956 (2) | 0.86171 (13) | 0.0606 (9) | |
C21 | 0.2781 (5) | 0.8289 (2) | 0.82093 (13) | 0.0793 (12) | |
H21A | 0.1806 | 0.8603 | 0.8322 | 0.119* | |
H21B | 0.2374 | 0.7839 | 0.8019 | 0.119* | |
H21C | 0.3521 | 0.8641 | 0.8025 | 0.119* | |
C22 | 0.4723 (4) | 0.53757 (17) | 0.99232 (9) | 0.0427 (7) | |
C23 | 0.3525 (4) | 0.4714 (2) | 0.97065 (10) | 0.0537 (8) | |
H23A | 0.2590 | 0.4596 | 0.9920 | 0.081* | |
H23B | 0.4178 | 0.4218 | 0.9650 | 0.081* | |
H23C | 0.3059 | 0.4916 | 0.9415 | 0.081* | |
C24 | 0.3551 (4) | 0.5997 (2) | 1.01821 (11) | 0.0567 (8) | |
H24A | 0.4240 | 0.6474 | 1.0273 | 0.068* | |
H24B | 0.2652 | 0.6187 | 0.9969 | 0.068* | |
C25 | 0.2702 (4) | 0.5633 (2) | 1.06176 (11) | 0.0612 (9) | |
H25A | 0.1995 | 0.6051 | 1.0770 | 0.073* | |
H25B | 0.1951 | 0.5177 | 1.0528 | 0.073* | |
C26 | 0.4069 (4) | 0.53286 (19) | 1.09541 (10) | 0.0526 (8) | |
H26 | 0.4727 | 0.5807 | 1.1069 | 0.063* | |
C27 | 0.3014 (5) | 0.5363 (3) | 1.17474 (12) | 0.0698 (10) | |
C28 | 0.2086 (7) | 0.4860 (3) | 1.21129 (12) | 0.1058 (16) | |
H28A | 0.2609 | 0.4322 | 1.2133 | 0.159* | |
H28B | 0.0885 | 0.4804 | 1.2027 | 0.159* | |
H28C | 0.2171 | 0.5133 | 1.2412 | 0.159* | |
C29 | 0.5362 (4) | 0.46892 (18) | 1.07605 (9) | 0.0454 (7) | |
C30 | 0.4519 (5) | 0.38367 (19) | 1.07045 (11) | 0.0591 (9) | |
H30A | 0.4195 | 0.3627 | 1.1008 | 0.089* | |
H30B | 0.5330 | 0.3464 | 1.0560 | 0.089* | |
H30C | 0.3502 | 0.3884 | 1.0511 | 0.089* | |
C31 | 0.6807 (5) | 0.4635 (2) | 1.11355 (10) | 0.0581 (9) | |
H31A | 0.6294 | 0.4641 | 1.1443 | 0.087* | |
H31B | 0.7577 | 0.5099 | 1.1103 | 0.087* | |
H31C | 0.7449 | 0.4130 | 1.1094 | 0.087* | |
C32 | 0.6090 (4) | 0.50400 (16) | 1.02858 (9) | 0.0398 (6) | |
H32 | 0.6786 | 0.5523 | 1.0375 | 0.048* | |
C33 | 0.7351 (4) | 0.44676 (16) | 1.00231 (9) | 0.0407 (7) | |
H33 | 0.6682 | 0.4034 | 0.9863 | 0.049* | |
C34 | 0.9002 (5) | 0.3292 (2) | 1.02639 (14) | 0.0645 (9) | |
C35 | 1.0098 (5) | 0.2951 (2) | 1.06456 (14) | 0.0847 (13) | |
H35A | 0.9449 | 0.2543 | 1.0818 | 0.127* | |
H35B | 1.0441 | 0.3389 | 1.0854 | 0.127* | |
H35C | 1.1114 | 0.2698 | 1.0513 | 0.127* | |
C36 | 0.7616 (6) | 0.5761 (2) | 0.75780 (12) | 0.0797 (12) | |
H36A | 0.7418 | 0.5727 | 0.7245 | 0.120* | |
H36B | 0.6650 | 0.5519 | 0.7742 | 0.120* | |
H36C | 0.8660 | 0.5466 | 0.7656 | 0.120* | |
O1 | 0.9096 (7) | 0.87108 (16) | 0.71447 (9) | 0.1250 (15) | |
H1 | 0.9242 | 0.8572 | 0.7419 | 0.188* | |
O2 | 0.9193 (3) | 0.70347 (14) | 0.74538 (7) | 0.0628 (6) | |
O3 | 0.4598 (3) | 0.72584 (12) | 0.85100 (7) | 0.0506 (5) | |
O4 | 0.3818 (5) | 0.82663 (17) | 0.90006 (10) | 0.1007 (10) | |
O5 | 0.8577 (3) | 0.40815 (12) | 1.03405 (6) | 0.0487 (5) | |
O6 | 0.8527 (5) | 0.29176 (17) | 0.99273 (14) | 0.1268 (14) | |
O7 | 0.3183 (3) | 0.49444 (14) | 1.13542 (7) | 0.0617 (6) | |
O8 | 0.3532 (6) | 0.60487 (19) | 1.18027 (10) | 0.1177 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.115 (4) | 0.121 (4) | 0.072 (3) | −0.054 (4) | −0.001 (3) | 0.025 (3) |
C2 | 0.153 (4) | 0.071 (2) | 0.0471 (19) | −0.024 (3) | −0.007 (3) | 0.0122 (18) |
C3 | 0.124 (4) | 0.061 (2) | 0.043 (2) | −0.021 (2) | −0.005 (2) | 0.0010 (16) |
C4 | 0.084 (3) | 0.064 (2) | 0.0417 (18) | −0.008 (2) | 0.0018 (18) | 0.0070 (16) |
C5 | 0.079 (3) | 0.128 (4) | 0.059 (2) | 0.002 (3) | −0.005 (2) | 0.017 (2) |
C6 | 0.064 (2) | 0.108 (3) | 0.0461 (19) | −0.002 (2) | −0.0051 (18) | 0.0076 (19) |
C7 | 0.058 (2) | 0.069 (2) | 0.0470 (18) | −0.0120 (18) | 0.0071 (16) | 0.0079 (16) |
C8 | 0.0502 (18) | 0.0514 (18) | 0.0458 (17) | −0.0065 (16) | −0.0007 (15) | 0.0055 (14) |
C9 | 0.0511 (19) | 0.070 (2) | 0.060 (2) | −0.0027 (18) | 0.0056 (16) | 0.0103 (17) |
C10 | 0.0380 (15) | 0.066 (2) | 0.0564 (18) | 0.0029 (15) | 0.0056 (15) | 0.0109 (16) |
C11 | 0.0368 (15) | 0.0464 (16) | 0.0449 (16) | −0.0026 (14) | −0.0012 (13) | 0.0029 (13) |
C12 | 0.0494 (18) | 0.0583 (19) | 0.060 (2) | −0.0145 (16) | −0.0097 (17) | 0.0103 (15) |
C13 | 0.0372 (14) | 0.0447 (16) | 0.0373 (15) | 0.0017 (13) | 0.0012 (12) | −0.0013 (12) |
C14 | 0.0547 (17) | 0.0498 (17) | 0.0449 (16) | −0.0022 (16) | 0.0055 (15) | −0.0046 (14) |
C15 | 0.0401 (15) | 0.0451 (16) | 0.0465 (17) | 0.0040 (13) | 0.0002 (14) | 0.0014 (13) |
C16 | 0.0401 (15) | 0.0397 (15) | 0.0394 (15) | 0.0027 (13) | −0.0035 (13) | −0.0013 (12) |
C17 | 0.0445 (16) | 0.0540 (18) | 0.0465 (17) | 0.0083 (15) | 0.0012 (14) | 0.0032 (14) |
C18 | 0.0453 (16) | 0.0471 (17) | 0.0448 (16) | 0.0043 (14) | −0.0082 (14) | 0.0046 (13) |
C19 | 0.0396 (15) | 0.0438 (16) | 0.0393 (15) | −0.0017 (13) | −0.0029 (13) | −0.0011 (13) |
C20 | 0.060 (2) | 0.053 (2) | 0.069 (2) | 0.0124 (18) | −0.0128 (18) | −0.0024 (17) |
C21 | 0.081 (3) | 0.069 (2) | 0.087 (3) | 0.024 (2) | −0.011 (2) | 0.016 (2) |
C22 | 0.0408 (15) | 0.0469 (16) | 0.0403 (15) | 0.0018 (14) | 0.0019 (13) | −0.0021 (13) |
C23 | 0.0424 (16) | 0.070 (2) | 0.0489 (18) | −0.0064 (17) | −0.0022 (15) | 0.0016 (16) |
C24 | 0.0553 (19) | 0.064 (2) | 0.0510 (18) | 0.0154 (18) | 0.0026 (16) | 0.0064 (15) |
C25 | 0.059 (2) | 0.068 (2) | 0.057 (2) | 0.0167 (18) | 0.0169 (17) | 0.0012 (17) |
C26 | 0.0605 (19) | 0.0519 (18) | 0.0455 (17) | −0.0080 (17) | 0.0132 (16) | −0.0030 (14) |
C27 | 0.080 (3) | 0.078 (3) | 0.052 (2) | −0.010 (2) | 0.0204 (19) | −0.0053 (19) |
C28 | 0.129 (4) | 0.124 (4) | 0.065 (2) | −0.038 (3) | 0.040 (3) | −0.008 (2) |
C29 | 0.0515 (17) | 0.0460 (17) | 0.0388 (15) | −0.0018 (15) | 0.0041 (14) | 0.0001 (13) |
C30 | 0.071 (2) | 0.0522 (19) | 0.0540 (19) | −0.0110 (18) | 0.0091 (17) | 0.0003 (15) |
C31 | 0.070 (2) | 0.061 (2) | 0.0425 (17) | −0.0027 (19) | −0.0006 (16) | 0.0040 (15) |
C32 | 0.0438 (16) | 0.0365 (14) | 0.0391 (15) | −0.0028 (13) | −0.0030 (13) | −0.0028 (12) |
C33 | 0.0394 (15) | 0.0418 (16) | 0.0409 (16) | 0.0024 (13) | −0.0037 (13) | −0.0024 (13) |
C34 | 0.053 (2) | 0.049 (2) | 0.092 (3) | 0.0138 (17) | −0.001 (2) | 0.0021 (19) |
C35 | 0.067 (2) | 0.071 (2) | 0.116 (3) | 0.022 (2) | 0.011 (2) | 0.042 (2) |
C36 | 0.102 (3) | 0.082 (3) | 0.055 (2) | −0.027 (3) | 0.016 (2) | −0.0087 (19) |
O1 | 0.247 (5) | 0.0678 (17) | 0.0601 (16) | −0.010 (3) | −0.016 (3) | −0.0145 (13) |
O2 | 0.0642 (14) | 0.0761 (15) | 0.0481 (12) | −0.0093 (13) | 0.0046 (12) | 0.0153 (11) |
O3 | 0.0531 (12) | 0.0510 (12) | 0.0478 (12) | 0.0099 (11) | −0.0038 (10) | 0.0040 (9) |
O4 | 0.125 (2) | 0.0804 (18) | 0.097 (2) | 0.0432 (18) | −0.036 (2) | −0.0276 (17) |
O5 | 0.0498 (12) | 0.0464 (12) | 0.0500 (12) | 0.0058 (10) | −0.0068 (10) | 0.0058 (9) |
O6 | 0.136 (3) | 0.076 (2) | 0.168 (3) | 0.047 (2) | −0.066 (3) | −0.054 (2) |
O7 | 0.0776 (15) | 0.0617 (14) | 0.0458 (12) | −0.0106 (12) | 0.0191 (12) | −0.0055 (10) |
O8 | 0.186 (3) | 0.089 (2) | 0.0789 (19) | −0.046 (3) | 0.064 (2) | −0.0343 (16) |
C1—C3 | 1.522 (7) | C18—C19 | 1.509 (4) |
C1—H1A | 0.9600 | C18—H18 | 0.9800 |
C1—H1B | 0.9600 | C19—H19 | 0.9800 |
C1—H1C | 0.9600 | C20—O4 | 1.201 (4) |
C2—C3 | 1.531 (5) | C20—O3 | 1.327 (4) |
C2—H2A | 0.9600 | C20—C21 | 1.491 (5) |
C2—H2B | 0.9600 | C21—H21A | 0.9600 |
C2—H2C | 0.9600 | C21—H21B | 0.9600 |
C3—O1 | 1.414 (5) | C21—H21C | 0.9600 |
C3—C4 | 1.511 (5) | C22—C24 | 1.537 (4) |
C4—O2 | 1.440 (4) | C22—C23 | 1.540 (4) |
C4—C5 | 1.516 (6) | C22—C32 | 1.570 (4) |
C4—H4 | 0.9800 | C23—H23A | 0.9600 |
C5—C6 | 1.524 (5) | C23—H23B | 0.9600 |
C5—H5A | 0.9700 | C23—H23C | 0.9600 |
C5—H5B | 0.9700 | C24—C25 | 1.519 (4) |
C6—C7 | 1.520 (5) | C24—H24A | 0.9700 |
C6—H6A | 0.9700 | C24—H24B | 0.9700 |
C6—H6B | 0.9700 | C25—C26 | 1.504 (4) |
C7—O2 | 1.439 (4) | C25—H25A | 0.9700 |
C7—C36 | 1.527 (5) | C25—H25B | 0.9700 |
C7—C8 | 1.536 (4) | C26—O7 | 1.464 (3) |
C8—C19 | 1.554 (4) | C26—C29 | 1.536 (4) |
C8—C9 | 1.558 (5) | C26—H26 | 0.9800 |
C8—H8 | 0.9800 | C27—O8 | 1.187 (4) |
C9—C10 | 1.525 (4) | C27—O7 | 1.313 (4) |
C9—H9A | 0.9700 | C27—C28 | 1.500 (5) |
C9—H9B | 0.9700 | C28—H28A | 0.9600 |
C10—C11 | 1.529 (4) | C28—H28B | 0.9600 |
C10—H10A | 0.9700 | C28—H28C | 0.9600 |
C10—H10B | 0.9700 | C29—C30 | 1.531 (4) |
C11—C12 | 1.546 (4) | C29—C31 | 1.543 (4) |
C11—C19 | 1.550 (4) | C29—C32 | 1.567 (4) |
C11—C13 | 1.568 (4) | C30—H30A | 0.9600 |
C12—H12A | 0.9600 | C30—H30B | 0.9600 |
C12—H12B | 0.9600 | C30—H30C | 0.9600 |
C12—H12C | 0.9600 | C31—H31A | 0.9600 |
C13—C15 | 1.532 (4) | C31—H31B | 0.9600 |
C13—C14 | 1.543 (4) | C31—H31C | 0.9600 |
C13—C16 | 1.565 (4) | C32—C33 | 1.534 (4) |
C14—H14A | 0.9600 | C32—H32 | 0.9800 |
C14—H14B | 0.9600 | C33—O5 | 1.447 (3) |
C14—H14C | 0.9600 | C33—H33 | 0.9800 |
C15—C33 | 1.514 (4) | C34—O6 | 1.190 (4) |
C15—H15A | 0.9700 | C34—O5 | 1.334 (4) |
C15—H15B | 0.9700 | C34—C35 | 1.481 (5) |
C16—C17 | 1.537 (4) | C35—H35A | 0.9600 |
C16—C22 | 1.570 (4) | C35—H35B | 0.9600 |
C16—H16 | 0.9800 | C35—H35C | 0.9600 |
C17—C18 | 1.526 (4) | C36—H36A | 0.9600 |
C17—H17A | 0.9700 | C36—H36B | 0.9600 |
C17—H17B | 0.9700 | C36—H36C | 0.9600 |
C18—O3 | 1.453 (3) | O1—H1 | 0.8200 |
C3—C1—H1A | 109.5 | C19—C18—H18 | 109.6 |
C3—C1—H1B | 109.5 | C17—C18—H18 | 109.6 |
H1A—C1—H1B | 109.5 | C18—C19—C11 | 108.2 (2) |
C3—C1—H1C | 109.5 | C18—C19—C8 | 122.4 (3) |
H1A—C1—H1C | 109.5 | C11—C19—C8 | 105.5 (2) |
H1B—C1—H1C | 109.5 | C18—C19—H19 | 106.6 |
C3—C2—H2A | 109.5 | C11—C19—H19 | 106.6 |
C3—C2—H2B | 109.5 | C8—C19—H19 | 106.6 |
H2A—C2—H2B | 109.5 | O4—C20—O3 | 123.4 (3) |
C3—C2—H2C | 109.5 | O4—C20—C21 | 124.7 (3) |
H2A—C2—H2C | 109.5 | O3—C20—C21 | 111.9 (3) |
H2B—C2—H2C | 109.5 | C20—C21—H21A | 109.5 |
O1—C3—C4 | 109.9 (3) | C20—C21—H21B | 109.5 |
O1—C3—C1 | 110.5 (4) | H21A—C21—H21B | 109.5 |
C4—C3—C1 | 110.1 (4) | C20—C21—H21C | 109.5 |
O1—C3—C2 | 106.1 (3) | H21A—C21—H21C | 109.5 |
C4—C3—C2 | 109.6 (3) | H21B—C21—H21C | 109.5 |
C1—C3—C2 | 110.6 (4) | C24—C22—C23 | 107.1 (2) |
O2—C4—C3 | 108.1 (3) | C24—C22—C32 | 107.7 (2) |
O2—C4—C5 | 105.3 (3) | C23—C22—C32 | 115.1 (2) |
C3—C4—C5 | 117.6 (4) | C24—C22—C16 | 108.1 (2) |
O2—C4—H4 | 108.5 | C23—C22—C16 | 112.2 (2) |
C3—C4—H4 | 108.5 | C32—C22—C16 | 106.5 (2) |
C5—C4—H4 | 108.5 | C22—C23—H23A | 109.5 |
C4—C5—C6 | 105.0 (3) | C22—C23—H23B | 109.5 |
C4—C5—H5A | 110.7 | H23A—C23—H23B | 109.5 |
C6—C5—H5A | 110.7 | C22—C23—H23C | 109.5 |
C4—C5—H5B | 110.7 | H23A—C23—H23C | 109.5 |
C6—C5—H5B | 110.7 | H23B—C23—H23C | 109.5 |
H5A—C5—H5B | 108.8 | C25—C24—C22 | 113.0 (3) |
C7—C6—C5 | 103.0 (3) | C25—C24—H24A | 109.0 |
C7—C6—H6A | 111.2 | C22—C24—H24A | 109.0 |
C5—C6—H6A | 111.2 | C25—C24—H24B | 109.0 |
C7—C6—H6B | 111.2 | C22—C24—H24B | 109.0 |
C5—C6—H6B | 111.2 | H24A—C24—H24B | 107.8 |
H6A—C6—H6B | 109.1 | C26—C25—C24 | 110.2 (3) |
O2—C7—C6 | 101.8 (2) | C26—C25—H25A | 109.6 |
O2—C7—C36 | 108.9 (3) | C24—C25—H25A | 109.6 |
C6—C7—C36 | 112.3 (3) | C26—C25—H25B | 109.6 |
O2—C7—C8 | 104.7 (3) | C24—C25—H25B | 109.6 |
C6—C7—C8 | 115.2 (3) | H25A—C25—H25B | 108.1 |
C36—C7—C8 | 112.8 (3) | O7—C26—C25 | 107.9 (3) |
C7—C8—C19 | 115.9 (3) | O7—C26—C29 | 107.2 (2) |
C7—C8—C9 | 110.7 (3) | C25—C26—C29 | 116.4 (2) |
C19—C8—C9 | 104.2 (2) | O7—C26—H26 | 108.4 |
C7—C8—H8 | 108.6 | C25—C26—H26 | 108.4 |
C19—C8—H8 | 108.6 | C29—C26—H26 | 108.4 |
C9—C8—H8 | 108.6 | O8—C27—O7 | 124.0 (3) |
C10—C9—C8 | 105.9 (3) | O8—C27—C28 | 125.0 (3) |
C10—C9—H9A | 110.5 | O7—C27—C28 | 111.0 (4) |
C8—C9—H9A | 110.5 | C27—C28—H28A | 109.5 |
C10—C9—H9B | 110.5 | C27—C28—H28B | 109.5 |
C8—C9—H9B | 110.5 | H28A—C28—H28B | 109.5 |
H9A—C9—H9B | 108.7 | C27—C28—H28C | 109.5 |
C9—C10—C11 | 103.5 (3) | H28A—C28—H28C | 109.5 |
C9—C10—H10A | 111.1 | H28B—C28—H28C | 109.5 |
C11—C10—H10A | 111.1 | C30—C29—C26 | 111.6 (2) |
C9—C10—H10B | 111.1 | C30—C29—C31 | 109.0 (2) |
C11—C10—H10B | 111.1 | C26—C29—C31 | 104.9 (2) |
H10A—C10—H10B | 109.0 | C30—C29—C32 | 112.8 (2) |
C10—C11—C12 | 106.2 (2) | C26—C29—C32 | 107.3 (2) |
C10—C11—C19 | 100.8 (2) | C31—C29—C32 | 111.0 (2) |
C12—C11—C19 | 110.8 (2) | C29—C30—H30A | 109.5 |
C10—C11—C13 | 116.6 (2) | C29—C30—H30B | 109.5 |
C12—C11—C13 | 112.5 (2) | H30A—C30—H30B | 109.5 |
C19—C11—C13 | 109.2 (2) | C29—C30—H30C | 109.5 |
C11—C12—H12A | 109.5 | H30A—C30—H30C | 109.5 |
C11—C12—H12B | 109.5 | H30B—C30—H30C | 109.5 |
H12A—C12—H12B | 109.5 | C29—C31—H31A | 109.5 |
C11—C12—H12C | 109.5 | C29—C31—H31B | 109.5 |
H12A—C12—H12C | 109.5 | H31A—C31—H31B | 109.5 |
H12B—C12—H12C | 109.5 | C29—C31—H31C | 109.5 |
C15—C13—C14 | 107.6 (2) | H31A—C31—H31C | 109.5 |
C15—C13—C16 | 108.3 (2) | H31B—C31—H31C | 109.5 |
C14—C13—C16 | 112.7 (2) | C33—C32—C29 | 115.3 (2) |
C15—C13—C11 | 111.1 (2) | C33—C32—C22 | 108.2 (2) |
C14—C13—C11 | 110.2 (2) | C29—C32—C22 | 116.8 (2) |
C16—C13—C11 | 106.9 (2) | C33—C32—H32 | 105.1 |
C13—C14—H14A | 109.5 | C29—C32—H32 | 105.1 |
C13—C14—H14B | 109.5 | C22—C32—H32 | 105.1 |
H14A—C14—H14B | 109.5 | O5—C33—C15 | 107.8 (2) |
C13—C14—H14C | 109.5 | O5—C33—C32 | 111.6 (2) |
H14A—C14—H14C | 109.5 | C15—C33—C32 | 110.8 (2) |
H14B—C14—H14C | 109.5 | O5—C33—H33 | 108.9 |
C33—C15—C13 | 113.5 (2) | C15—C33—H33 | 108.9 |
C33—C15—H15A | 108.9 | C32—C33—H33 | 108.9 |
C13—C15—H15A | 108.9 | O6—C34—O5 | 122.8 (3) |
C33—C15—H15B | 108.9 | O6—C34—C35 | 125.1 (4) |
C13—C15—H15B | 108.9 | O5—C34—C35 | 112.1 (3) |
H15A—C15—H15B | 107.7 | C34—C35—H35A | 109.5 |
C17—C16—C13 | 111.1 (2) | C34—C35—H35B | 109.5 |
C17—C16—C22 | 115.1 (2) | H35A—C35—H35B | 109.5 |
C13—C16—C22 | 115.8 (2) | C34—C35—H35C | 109.5 |
C17—C16—H16 | 104.4 | H35A—C35—H35C | 109.5 |
C13—C16—H16 | 104.4 | H35B—C35—H35C | 109.5 |
C22—C16—H16 | 104.4 | C7—C36—H36A | 109.5 |
C18—C17—C16 | 113.1 (2) | C7—C36—H36B | 109.5 |
C18—C17—H17A | 109.0 | H36A—C36—H36B | 109.5 |
C16—C17—H17A | 109.0 | C7—C36—H36C | 109.5 |
C18—C17—H17B | 109.0 | H36A—C36—H36C | 109.5 |
C16—C17—H17B | 109.0 | H36B—C36—H36C | 109.5 |
H17A—C17—H17B | 107.8 | C3—O1—H1 | 109.5 |
O3—C18—C19 | 108.9 (2) | C7—O2—C4 | 109.6 (2) |
O3—C18—C17 | 108.6 (2) | C20—O3—C18 | 118.5 (2) |
C19—C18—C17 | 110.6 (2) | C34—O5—C33 | 118.0 (2) |
O3—C18—H18 | 109.6 | C27—O7—C26 | 119.3 (3) |
O1—C3—C4—O2 | −65.8 (4) | C9—C8—C19—C18 | 142.2 (3) |
C1—C3—C4—O2 | 56.1 (4) | C7—C8—C19—C11 | 139.9 (3) |
C2—C3—C4—O2 | 177.9 (3) | C9—C8—C19—C11 | 18.0 (3) |
O1—C3—C4—C5 | 53.1 (5) | C17—C16—C22—C24 | −56.5 (3) |
C1—C3—C4—C5 | 175.1 (4) | C13—C16—C22—C24 | 171.6 (2) |
C2—C3—C4—C5 | −63.1 (5) | C17—C16—C22—C23 | 61.3 (3) |
O2—C4—C5—C6 | 4.7 (4) | C13—C16—C22—C23 | −70.6 (3) |
C3—C4—C5—C6 | −115.7 (4) | C17—C16—C22—C32 | −172.0 (2) |
C4—C5—C6—C7 | −26.2 (4) | C13—C16—C22—C32 | 56.2 (3) |
C5—C6—C7—O2 | 37.8 (4) | C23—C22—C24—C25 | 69.1 (3) |
C5—C6—C7—C36 | −78.5 (4) | C32—C22—C24—C25 | −55.2 (3) |
C5—C6—C7—C8 | 150.5 (3) | C16—C22—C24—C25 | −169.9 (3) |
O2—C7—C8—C19 | −177.4 (3) | C22—C24—C25—C26 | 58.4 (4) |
C6—C7—C8—C19 | 71.7 (4) | C24—C25—C26—O7 | −177.0 (3) |
C36—C7—C8—C19 | −59.1 (4) | C24—C25—C26—C29 | −56.5 (4) |
O2—C7—C8—C9 | −59.1 (3) | O7—C26—C29—C30 | 47.0 (3) |
C6—C7—C8—C9 | −170.0 (3) | C25—C26—C29—C30 | −73.8 (3) |
C36—C7—C8—C9 | 59.3 (4) | O7—C26—C29—C31 | −70.9 (3) |
C7—C8—C9—C10 | −115.6 (3) | C25—C26—C29—C31 | 168.3 (3) |
C19—C8—C9—C10 | 9.7 (3) | O7—C26—C29—C32 | 170.9 (2) |
C8—C9—C10—C11 | −34.2 (3) | C25—C26—C29—C32 | 50.1 (3) |
C9—C10—C11—C12 | −71.1 (3) | C30—C29—C32—C33 | −54.0 (3) |
C9—C10—C11—C19 | 44.5 (3) | C26—C29—C32—C33 | −177.2 (2) |
C9—C10—C11—C13 | 162.5 (2) | C31—C29—C32—C33 | 68.7 (3) |
C10—C11—C13—C15 | 66.1 (3) | C30—C29—C32—C22 | 74.7 (3) |
C12—C11—C13—C15 | −57.1 (3) | C26—C29—C32—C22 | −48.5 (3) |
C19—C11—C13—C15 | 179.4 (2) | C31—C29—C32—C22 | −162.5 (2) |
C10—C11—C13—C14 | −53.1 (3) | C24—C22—C32—C33 | −175.9 (2) |
C12—C11—C13—C14 | −176.3 (2) | C23—C22—C32—C33 | 64.8 (3) |
C19—C11—C13—C14 | 60.2 (3) | C16—C22—C32—C33 | −60.2 (3) |
C10—C11—C13—C16 | −175.9 (2) | C24—C22—C32—C29 | 52.0 (3) |
C12—C11—C13—C16 | 61.0 (3) | C23—C22—C32—C29 | −67.3 (3) |
C19—C11—C13—C16 | −62.5 (3) | C16—C22—C32—C29 | 167.7 (2) |
C14—C13—C15—C33 | −71.5 (3) | C13—C15—C33—O5 | 177.4 (2) |
C16—C13—C15—C33 | 50.6 (3) | C13—C15—C33—C32 | −60.3 (3) |
C11—C13—C15—C33 | 167.8 (2) | C29—C32—C33—O5 | −42.7 (3) |
C15—C13—C16—C17 | 175.7 (2) | C22—C32—C33—O5 | −175.6 (2) |
C14—C13—C16—C17 | −65.3 (3) | C29—C32—C33—C15 | −162.8 (2) |
C11—C13—C16—C17 | 55.9 (3) | C22—C32—C33—C15 | 64.3 (3) |
C15—C13—C16—C22 | −50.6 (3) | C6—C7—O2—C4 | −37.0 (3) |
C14—C13—C16—C22 | 68.4 (3) | C36—C7—O2—C4 | 81.8 (3) |
C11—C13—C16—C22 | −170.4 (2) | C8—C7—O2—C4 | −157.3 (3) |
C13—C16—C17—C18 | −53.3 (3) | C3—C4—O2—C7 | 147.0 (3) |
C22—C16—C17—C18 | 172.6 (2) | C5—C4—O2—C7 | 20.5 (4) |
C16—C17—C18—O3 | 174.6 (2) | O4—C20—O3—C18 | −6.4 (5) |
C16—C17—C18—C19 | 55.1 (3) | C21—C20—O3—C18 | 174.9 (3) |
O3—C18—C19—C11 | −179.3 (2) | C19—C18—O3—C20 | −153.5 (3) |
C17—C18—C19—C11 | −60.1 (3) | C17—C18—O3—C20 | 86.0 (3) |
O3—C18—C19—C8 | 57.8 (3) | O6—C34—O5—C33 | 6.2 (5) |
C17—C18—C19—C8 | 177.0 (3) | C35—C34—O5—C33 | −173.2 (3) |
C10—C11—C19—C18 | −171.2 (2) | C15—C33—O5—C34 | −97.3 (3) |
C12—C11—C19—C18 | −59.0 (3) | C32—C33—O5—C34 | 140.9 (3) |
C13—C11—C19—C18 | 65.5 (3) | O8—C27—O7—C26 | 0.4 (6) |
C10—C11—C19—C8 | −38.6 (3) | C28—C27—O7—C26 | −179.6 (3) |
C12—C11—C19—C8 | 73.6 (3) | C25—C26—O7—C27 | −100.7 (4) |
C13—C11—C19—C8 | −161.9 (2) | C29—C26—O7—C27 | 133.3 (3) |
C7—C8—C19—C18 | −96.0 (3) |
D—H···A | D—H | H···A | D···A | 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+1/2, −y+3/2, −z+2; (ii) x+1/2, −y+1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C36H58O8 |
Mr | 618.82 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 298 |
a, b, c (Å) | 7.6936 (11), 16.151 (2), 28.439 (4) |
V (Å3) | 3533.7 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.41 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18696, 3738, 2746 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.115, 1.04 |
No. of reflections | 3738 |
No. of parameters | 409 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.15 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | 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+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.
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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.