organic compounds
Koetjapic acid chloroform hemisolvate
aDepartment of Pharmacology, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my
The 30H46O4·0.5CHCl3, consists of one koetjapic acid [systematic name: (3R,4aR,4bS,7S,8S,10bS,12aS)-7-(2-carboxyethyl)-3,4b,7,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-1,2,3,4,4a,4b,5,6,7,8,9,10,10b,11,12,12a-hexadecahydrochrysene-3-carboxylic acid] molecule and one half-molecule of chloroform solvent, which is disordered about a twofold rotation axis. The symmetry-independent component is further disordered over two sites, with occupancies of 0.30 and 0.20. The koetjapic acid contains a fused four-ring system, A/B/C/D. The A/B, B/C and C/D junctions adopt E/trans/cis configurations, respectively. The conformation of ring A is intermediate between envelope and half-chair and ring B adopts an whereas rings C and D adopt chair conformations. A weak intramolecular C—H⋯O hydrogen bond is observed. The koetjapic acid molecules are linked into dimers by two pairs of intermolecular O—H⋯O hydrogen bonds. The dimers are stacked along the c axis.
of the title compound, CRelated literature
For the biological properties of Sandoricum koetjape and koetjapic acid, see: Aisha et al. (2009); Kaneda et al. (1992); Sun et al. (1999); Ismail et al. (2003); Rasadah et al. (2004). For ring puckering parameters, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536810016430/ci5066sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016430/ci5066Isup2.hkl
The title compound was isolated from the stem bark of Sandoricum koetjape, which was collected from the main campus of Universiti Sains Malaysia on middle of October 2009. 200 g of the dried powder was extracted with 1000 ml of n-hexane at 313 K for 24 hours with intermittent shaking. The extract was filtered and concentrated to dryness under reduced pressure at 313 K to give 10 g of solid material. 10 g of the extract was dissolved in 50 ml, 1:1, methanol-acetone and was kept at 253 K. After 24 hours, a white precipitate was formed. The solid was filtered and washed thrice with ice-chilled chloroform. The compound was crystallized from chloroform to give colourless prism-shaped crystals (400 mg). Single crystals suitable for X-ray analysis were obtained by slow evaporation of a chloroform solution at room temperature.
All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93–0.98 Å, Uiso(H) = 1.2 or 1.5 Ueq(C) and O–H = 0.82 Å, Uiso(H) = 1.5 Ueq(O). A rotating group model was applied for the methyl groups. The chloroform molecule is disordered across a twofold rotation axis. The symmetry independent component is further disordered over two sites with occupancies of 0.30 and 0.20. All C—Cl distances were restrained to be equal and Uij components of Cl atoms were restrained to an approximate isotropic behaviour. The distance between atoms Cl3 and Cl4 at (1-x, 2-y, z) were restrained to 2.60 (1) Å. The highest residual electron density peak is located at 0.53 Å from Cl3 and the deepest hole is located at 0.68 Å from Cl2. 1876 Friedel pairs were used to determine the α radiation.
using the of the CuKn-Hexane extract of Sandoricum koetjape was reported previously to have cytotoxic and apoptotic properties on HCT-116 colon cancer cell line (Aisha et al., 2009). The koetjapic acid can be isolated from the stem bark of S. koetjape using β inhibition (Sun et al., 1999), ichthyotoxic (Ismail et al., 2003), and anti-inflammatory properties (Rasadah et al., 2004). The structure of koetjapic acid was established previously by several research groups from spectral evidence (Kaneda et al., 1992; Rasadah et al., 2004; Sun et al., 1999). Herein we describe a new simple method to purify koetjapic acid from Sandoricum koetjape. This method utilizes two steps of crystallization process but without the use of column chromatography.
and was studied for cytotoxic activity (Kaneda et al., 1992). This compound was found to possess DNA polymeraseThe θ = 131.6 (3)°, φ = 45.7 (5)°]. The ring B adopts an [Q = 0.509 (3) Å, θ = 52.9 (3)°, φ = 177.6 (5)°] whereas ring C and D adopt chair conformations [Q = 0.561 (3) Å, θ = 155.6 (3)°, φ = 117.8 (8)°; Q = 0.491 (4) Å, θ = 168.1 (5)°, φ = 77 (2)°] (Cremer & Pople, 1975). A weak intramolecular C22—H22B···O1 hydrogen bond is observed in the molecular structure.
of title compound, consists of one koetjapic acid molecule and half a molecule of disordered chloroform solvent (Fig. 1). The koetjapic acid contains fused four-ring system, A/B/C/D (Scheme 1). The A/B, B/C and C/D junctions adopt E/trans/cis configuration, respectively. The conformation of the ring A is intermediate between envelope and half-chair [Q = 0.516 (4) Å,The koetjapic acid molecules are linked into dimers by two pairs of intermolecular O1—H1···O4 and O3—H3···O2 hydrogen bonds (Table 1). The dimers are stacked along the c axis (Fig. 2).
The chloroform molecule is disordered over four sites in a void with twofold symmetry. In one set of symmetry-related sites, atom Cl2 lies on the twofold rotation axis and the three Cl sites [Cl1, Cl2, Cl1A; occupancy 0.60] are shared by two disorder components. In the other set of symmetry-related site, atoms Cl3 and Cl3A [occupancy 0.40] are shared by two disorder components with atoms Cl4 or Cl4A [occupancy 0.20] in each component. The chloroform solvent molecule lies in the cavity produced by the dimer.
For the biological properties of Sandoricum koetjape and koetjapic acid, see: Aisha et al. (2009); Kaneda et al. (1992); Sun et al. (1999); Ismail et al. (2003); Rasadah et al. (2004). For ring puckering parameters, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 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) and PLATON (Spek, 2009).C30H46O4·0.5CHCl3 | F(000) = 1148 |
Mr = 530.35 | Dx = 1.240 Mg m−3 |
Orthorhombic, P21212 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2 2ab | Cell parameters from 9931 reflections |
a = 12.8950 (3) Å | θ = 2.6–65.7° |
b = 33.7309 (8) Å | µ = 1.88 mm−1 |
c = 6.5307 (1) Å | T = 100 K |
V = 2840.59 (10) Å3 | Block, colourless |
Z = 4 | 0.34 × 0.28 × 0.11 mm |
Bruker APEXII DUO CCD area-detector diffractometer | 4654 independent reflections |
Radiation source: fine-focus sealed tube | 4467 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 66.1°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −15→15 |
Tmin = 0.567, Tmax = 0.827 | k = −38→39 |
26063 measured reflections | l = −5→7 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.060 | w = 1/[σ2(Fo2) + (0.0958P)2 + 1.9305P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.169 | (Δ/σ)max = 0.001 |
S = 1.09 | Δρmax = 0.53 e Å−3 |
4654 reflections | Δρmin = −0.68 e Å−3 |
357 parameters | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
40 restraints | Extinction coefficient: 0.0082 (8) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1876 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.08 (5) |
C30H46O4·0.5CHCl3 | V = 2840.59 (10) Å3 |
Mr = 530.35 | Z = 4 |
Orthorhombic, P21212 | Cu Kα radiation |
a = 12.8950 (3) Å | µ = 1.88 mm−1 |
b = 33.7309 (8) Å | T = 100 K |
c = 6.5307 (1) Å | 0.34 × 0.28 × 0.11 mm |
Bruker APEXII DUO CCD area-detector diffractometer | 4654 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 4467 reflections with I > 2σ(I) |
Tmin = 0.567, Tmax = 0.827 | Rint = 0.031 |
26063 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.169 | Δρmax = 0.53 e Å−3 |
S = 1.09 | Δρmin = −0.68 e Å−3 |
4654 reflections | Absolute structure: Flack (1983), 1876 Friedel pairs |
357 parameters | Absolute structure parameter: 0.08 (5) |
40 restraints |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | Occ. (<1) | |
O1 | 0.2093 (2) | 0.96882 (8) | 0.3593 (5) | 0.0439 (8) | |
H1 | 0.2417 | 0.9868 | 0.4147 | 0.066* | |
O2 | 0.1261 (2) | 0.96828 (8) | 0.6601 (5) | 0.0436 (8) | |
O3 | 0.7713 (3) | 0.96911 (9) | 0.8069 (6) | 0.0514 (9) | |
H3 | 0.8000 | 0.9887 | 0.7590 | 0.077* | |
O4 | 0.6996 (5) | 0.96705 (14) | 0.4969 (7) | 0.106 (2) | |
C1 | 0.5175 (3) | 0.84482 (11) | 0.6074 (6) | 0.0304 (8) | |
C2 | 0.4878 (3) | 0.86704 (12) | 0.4167 (6) | 0.0329 (9) | |
H2A | 0.5314 | 0.8577 | 0.3056 | 0.039* | |
H2B | 0.5037 | 0.8949 | 0.4378 | 0.039* | |
C3 | 0.3751 (3) | 0.86394 (12) | 0.3479 (6) | 0.0328 (9) | |
H3A | 0.3678 | 0.8412 | 0.2578 | 0.039* | |
H3B | 0.3572 | 0.8875 | 0.2700 | 0.039* | |
C4 | 0.2988 (3) | 0.85964 (10) | 0.5262 (6) | 0.0262 (8) | |
C5 | 0.1868 (3) | 0.85387 (10) | 0.4384 (6) | 0.0264 (8) | |
H5A | 0.1946 | 0.8317 | 0.3427 | 0.032* | |
C6 | 0.1433 (3) | 0.88781 (10) | 0.3023 (6) | 0.0292 (8) | |
H6A | 0.2020 | 0.9006 | 0.2369 | 0.035* | |
H6B | 0.1027 | 0.8755 | 0.1944 | 0.035* | |
C7 | 0.0758 (3) | 0.92092 (11) | 0.3973 (7) | 0.0339 (9) | |
C8 | 0.0003 (3) | 0.90414 (12) | 0.5567 (7) | 0.0391 (10) | |
H8A | −0.0273 | 0.9259 | 0.6374 | 0.047* | |
H8B | −0.0574 | 0.8918 | 0.4859 | 0.047* | |
C9 | 0.0491 (3) | 0.87389 (12) | 0.7005 (7) | 0.0354 (9) | |
H9A | −0.0044 | 0.8636 | 0.7905 | 0.042* | |
H9B | 0.1000 | 0.8873 | 0.7851 | 0.042* | |
C10 | 0.1020 (3) | 0.83885 (11) | 0.5927 (6) | 0.0300 (9) | |
C11 | 0.1466 (3) | 0.81017 (12) | 0.7559 (6) | 0.0356 (9) | |
H11A | 0.1008 | 0.8107 | 0.8737 | 0.043* | |
H11B | 0.1444 | 0.7835 | 0.7001 | 0.043* | |
C12 | 0.2567 (3) | 0.81809 (12) | 0.8308 (6) | 0.0325 (9) | |
H12A | 0.2788 | 0.7966 | 0.9190 | 0.039* | |
H12B | 0.2578 | 0.8424 | 0.9103 | 0.039* | |
C13 | 0.3322 (3) | 0.82188 (10) | 0.6488 (5) | 0.0252 (8) | |
C14 | 0.4463 (3) | 0.82387 (10) | 0.7164 (5) | 0.0254 (8) | |
C15 | 0.4753 (3) | 0.79887 (11) | 0.8945 (6) | 0.0303 (8) | |
H15A | 0.4413 | 0.7734 | 0.8803 | 0.036* | |
H15B | 0.4484 | 0.8113 | 1.0176 | 0.036* | |
C16 | 0.5911 (3) | 0.79172 (12) | 0.9237 (6) | 0.0346 (9) | |
H16A | 0.6142 | 0.7710 | 0.8312 | 0.042* | |
H16B | 0.6043 | 0.7830 | 1.0628 | 0.042* | |
C17 | 0.6514 (3) | 0.82981 (11) | 0.8812 (6) | 0.0304 (8) | |
H17A | 0.6197 | 0.8505 | 0.9658 | 0.036* | |
C18 | 0.6348 (3) | 0.84244 (11) | 0.6529 (6) | 0.0270 (8) | |
C19 | 0.6891 (3) | 0.88239 (12) | 0.6111 (6) | 0.0335 (9) | |
H19A | 0.7628 | 0.8790 | 0.6352 | 0.040* | |
H19B | 0.6803 | 0.8888 | 0.4673 | 0.040* | |
C20 | 0.6517 (4) | 0.91792 (12) | 0.7379 (7) | 0.0440 (11) | |
H20A | 0.5779 | 0.9218 | 0.7178 | 0.053* | |
H20B | 0.6640 | 0.9130 | 0.8823 | 0.053* | |
C21 | 0.7097 (5) | 0.95397 (14) | 0.6711 (8) | 0.0539 (13) | |
C22 | 0.3104 (3) | 0.89708 (11) | 0.6604 (6) | 0.0325 (9) | |
H22A | 0.2509 | 0.8996 | 0.7478 | 0.049* | |
H22B | 0.3157 | 0.9200 | 0.5742 | 0.049* | |
H22C | 0.3718 | 0.8948 | 0.7427 | 0.049* | |
C23 | 0.1407 (3) | 0.95455 (11) | 0.4877 (7) | 0.0338 (9) | |
C24 | 0.0136 (4) | 0.94111 (12) | 0.2222 (8) | 0.0453 (11) | |
H24A | 0.0608 | 0.9509 | 0.1205 | 0.068* | |
H24B | −0.0260 | 0.9627 | 0.2770 | 0.068* | |
H24C | −0.0324 | 0.9221 | 0.1610 | 0.068* | |
C25 | 0.0193 (3) | 0.81565 (11) | 0.4729 (7) | 0.0378 (9) | |
H25A | −0.0317 | 0.8055 | 0.5663 | 0.057* | |
H25B | 0.0515 | 0.7940 | 0.4017 | 0.057* | |
H25C | −0.0136 | 0.8329 | 0.3758 | 0.057* | |
C26 | 0.3264 (3) | 0.78339 (11) | 0.5175 (6) | 0.0326 (9) | |
H26A | 0.3786 | 0.7842 | 0.4128 | 0.049* | |
H26B | 0.2592 | 0.7815 | 0.4551 | 0.049* | |
H26C | 0.3378 | 0.7607 | 0.6036 | 0.049* | |
C27 | 0.7649 (3) | 0.82688 (13) | 0.9473 (6) | 0.0357 (9) | |
C28 | 0.8203 (3) | 0.79269 (13) | 0.9245 (7) | 0.0440 (11) | |
H28A | 0.8880 | 0.7912 | 0.9730 | 0.066* | |
H28B | 0.7904 | 0.7709 | 0.8604 | 0.066* | |
C29 | 0.8118 (3) | 0.86138 (13) | 1.0484 (6) | 0.0407 (10) | |
H29A | 0.8764 | 0.8538 | 1.1099 | 0.061* | |
H29B | 0.7657 | 0.8711 | 1.1523 | 0.061* | |
H29C | 0.8240 | 0.8818 | 0.9491 | 0.061* | |
C30 | 0.6836 (3) | 0.81256 (12) | 0.5030 (6) | 0.0361 (9) | |
H30A | 0.6690 | 0.8205 | 0.3649 | 0.054* | |
H30B | 0.6549 | 0.7867 | 0.5271 | 0.054* | |
H30C | 0.7573 | 0.8118 | 0.5236 | 0.054* | |
C31 | 0.5335 (9) | 0.9947 (3) | 0.0839 (17) | 0.087 (5) | 0.50 |
H31A | 0.6041 | 0.9856 | 0.0890 | 0.104* | 0.299 (3) |
H31B | 0.5871 | 0.9780 | 0.1384 | 0.104* | 0.201 (3) |
Cl1 | 0.4660 (3) | 0.95921 (9) | 0.1615 (9) | 0.1061 (18) | 0.597 (7) |
Cl2 | 0.5000 | 1.0000 | −0.2013 (6) | 0.127 (3) | 0.597 (7) |
Cl3 | 0.4269 (6) | 0.9672 (3) | −0.0147 (14) | 0.153 (4) | 0.403 (7) |
Cl4 | 0.4584 (9) | 1.0233 (3) | 0.2864 (15) | 0.107 (4) | 0.201 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0454 (17) | 0.0302 (14) | 0.0561 (18) | −0.0102 (13) | 0.0042 (15) | −0.0052 (14) |
O2 | 0.0436 (17) | 0.0284 (14) | 0.059 (2) | −0.0053 (12) | 0.0067 (15) | −0.0103 (14) |
O3 | 0.0545 (19) | 0.0332 (15) | 0.067 (2) | −0.0172 (14) | −0.0117 (17) | 0.0117 (15) |
O4 | 0.166 (5) | 0.075 (3) | 0.076 (3) | −0.080 (3) | −0.044 (3) | 0.034 (2) |
C1 | 0.0276 (19) | 0.033 (2) | 0.0302 (19) | −0.0056 (16) | −0.0014 (16) | 0.0033 (15) |
C2 | 0.030 (2) | 0.044 (2) | 0.0252 (19) | 0.0015 (17) | 0.0039 (16) | 0.0049 (16) |
C3 | 0.033 (2) | 0.036 (2) | 0.030 (2) | −0.0023 (16) | −0.0003 (16) | 0.0074 (16) |
C4 | 0.0269 (18) | 0.0229 (17) | 0.0287 (18) | −0.0009 (14) | 0.0005 (15) | −0.0021 (14) |
C5 | 0.0267 (18) | 0.0226 (17) | 0.0298 (19) | −0.0008 (14) | −0.0016 (15) | −0.0012 (14) |
C6 | 0.0297 (19) | 0.0253 (18) | 0.033 (2) | −0.0020 (15) | −0.0062 (16) | −0.0020 (15) |
C7 | 0.0256 (19) | 0.0235 (18) | 0.053 (2) | 0.0005 (15) | −0.0041 (19) | −0.0037 (17) |
C8 | 0.030 (2) | 0.0284 (19) | 0.059 (3) | −0.0028 (17) | 0.0018 (19) | −0.0086 (18) |
C9 | 0.027 (2) | 0.036 (2) | 0.043 (2) | −0.0044 (16) | 0.0065 (17) | −0.0050 (18) |
C10 | 0.0264 (18) | 0.0276 (19) | 0.036 (2) | −0.0038 (15) | 0.0027 (16) | −0.0006 (16) |
C11 | 0.030 (2) | 0.036 (2) | 0.041 (2) | −0.0039 (17) | 0.0063 (18) | 0.0087 (17) |
C12 | 0.031 (2) | 0.036 (2) | 0.031 (2) | 0.0012 (16) | 0.0034 (16) | 0.0055 (17) |
C13 | 0.0256 (18) | 0.0250 (17) | 0.0250 (17) | −0.0030 (14) | 0.0028 (14) | 0.0002 (14) |
C14 | 0.031 (2) | 0.0205 (17) | 0.0246 (17) | −0.0027 (14) | −0.0020 (14) | −0.0041 (14) |
C15 | 0.034 (2) | 0.0255 (18) | 0.031 (2) | −0.0047 (16) | 0.0044 (17) | 0.0018 (15) |
C16 | 0.038 (2) | 0.033 (2) | 0.033 (2) | −0.0072 (18) | −0.0078 (17) | 0.0074 (16) |
C17 | 0.0301 (19) | 0.0321 (19) | 0.0288 (18) | −0.0076 (16) | −0.0003 (16) | 0.0018 (15) |
C18 | 0.0269 (19) | 0.0263 (18) | 0.0277 (18) | −0.0041 (15) | 0.0005 (15) | 0.0024 (14) |
C19 | 0.030 (2) | 0.036 (2) | 0.035 (2) | −0.0099 (16) | 0.0028 (17) | 0.0069 (16) |
C20 | 0.048 (3) | 0.032 (2) | 0.052 (3) | −0.0112 (19) | 0.004 (2) | −0.0015 (19) |
C21 | 0.075 (4) | 0.033 (2) | 0.054 (3) | −0.014 (2) | −0.013 (3) | 0.005 (2) |
C22 | 0.032 (2) | 0.0271 (19) | 0.038 (2) | −0.0031 (16) | −0.0067 (17) | −0.0032 (16) |
C23 | 0.030 (2) | 0.0221 (18) | 0.050 (2) | 0.0003 (15) | −0.0005 (19) | −0.0031 (18) |
C24 | 0.037 (2) | 0.031 (2) | 0.067 (3) | 0.0004 (18) | −0.012 (2) | 0.003 (2) |
C25 | 0.031 (2) | 0.028 (2) | 0.054 (2) | −0.0047 (17) | −0.0031 (19) | −0.0002 (18) |
C26 | 0.032 (2) | 0.0250 (18) | 0.041 (2) | −0.0009 (15) | −0.0048 (17) | −0.0022 (16) |
C27 | 0.037 (2) | 0.043 (2) | 0.0267 (19) | −0.0099 (18) | −0.0052 (16) | 0.0083 (17) |
C28 | 0.036 (2) | 0.042 (2) | 0.054 (3) | −0.0047 (19) | −0.013 (2) | 0.009 (2) |
C29 | 0.037 (2) | 0.050 (3) | 0.035 (2) | −0.0166 (19) | −0.0029 (18) | 0.0055 (18) |
C30 | 0.036 (2) | 0.040 (2) | 0.032 (2) | 0.0063 (17) | −0.0022 (17) | −0.0023 (17) |
C31 | 0.066 (8) | 0.051 (7) | 0.143 (13) | 0.020 (6) | −0.016 (8) | −0.002 (8) |
Cl1 | 0.103 (3) | 0.0606 (17) | 0.154 (4) | −0.0130 (16) | 0.036 (3) | 0.032 (2) |
Cl2 | 0.245 (7) | 0.078 (3) | 0.059 (2) | 0.095 (4) | 0.000 | 0.000 |
Cl3 | 0.154 (6) | 0.141 (6) | 0.162 (7) | −0.086 (5) | 0.055 (5) | −0.070 (6) |
Cl4 | 0.151 (8) | 0.077 (5) | 0.094 (6) | −0.008 (6) | 0.001 (6) | −0.038 (5) |
O1—C23 | 1.310 (5) | C17—C27 | 1.529 (6) |
O1—H1 | 0.82 | C17—C18 | 1.565 (5) |
O2—C23 | 1.232 (5) | C17—H17A | 0.98 |
O3—C21 | 1.296 (6) | C18—C30 | 1.539 (5) |
O3—H3 | 0.82 | C18—C19 | 1.543 (5) |
O4—C21 | 1.227 (6) | C19—C20 | 1.534 (6) |
C1—C14 | 1.360 (5) | C19—H19A | 0.97 |
C1—C2 | 1.504 (5) | C19—H19B | 0.97 |
C1—C18 | 1.544 (5) | C20—C21 | 1.492 (6) |
C2—C3 | 1.525 (6) | C20—H20A | 0.97 |
C2—H2A | 0.97 | C20—H20B | 0.97 |
C2—H2B | 0.97 | C22—H22A | 0.96 |
C3—C4 | 1.531 (5) | C22—H22B | 0.96 |
C3—H3A | 0.97 | C22—H22C | 0.96 |
C3—H3B | 0.97 | C24—H24A | 0.96 |
C4—C22 | 1.545 (5) | C24—H24B | 0.96 |
C4—C13 | 1.565 (5) | C24—H24C | 0.96 |
C4—C5 | 1.565 (5) | C25—H25A | 0.96 |
C5—C6 | 1.554 (5) | C25—H25B | 0.96 |
C5—C10 | 1.571 (5) | C25—H25C | 0.96 |
C5—H5A | 0.98 | C26—H26A | 0.96 |
C6—C7 | 1.546 (5) | C26—H26B | 0.96 |
C6—H6A | 0.97 | C26—H26C | 0.96 |
C6—H6B | 0.97 | C27—C28 | 1.365 (6) |
C7—C23 | 1.528 (5) | C27—C29 | 1.468 (6) |
C7—C8 | 1.534 (6) | C28—H28A | 0.93 |
C7—C24 | 1.554 (6) | C28—H28B | 0.93 |
C8—C9 | 1.523 (6) | C29—H29A | 0.96 |
C8—H8A | 0.97 | C29—H29B | 0.96 |
C8—H8B | 0.97 | C29—H29C | 0.96 |
C9—C10 | 1.536 (5) | C30—H30A | 0.96 |
C9—H9A | 0.97 | C30—H30B | 0.96 |
C9—H9B | 0.97 | C30—H30C | 0.96 |
C10—C25 | 1.538 (6) | C31—C31i | 0.94 (2) |
C10—C11 | 1.550 (5) | C31—Cl4i | 1.460 (13) |
C11—C12 | 1.525 (6) | C31—Cl3i | 1.526 (10) |
C11—H11A | 0.97 | C31—Cl1 | 1.564 (9) |
C11—H11B | 0.97 | C31—Cl1i | 1.635 (9) |
C12—C13 | 1.543 (5) | C31—Cl3 | 1.779 (11) |
C12—H12A | 0.97 | C31—Cl4 | 1.903 (12) |
C12—H12B | 0.97 | C31—Cl2 | 1.920 (12) |
C13—C14 | 1.538 (5) | C31—H31A | 0.96 |
C13—C26 | 1.558 (5) | C31—H31B | 0.96 |
C14—C15 | 1.484 (5) | Cl1—C31i | 1.635 (9) |
C15—C16 | 1.525 (6) | Cl1—H31B | 1.6921 |
C15—H15A | 0.97 | Cl2—C31i | 1.920 (12) |
C15—H15B | 0.97 | Cl3—C31i | 1.526 (10) |
C16—C17 | 1.527 (5) | Cl4—C31i | 1.460 (13) |
C16—H16A | 0.97 | Cl4—Cl4i | 1.91 (2) |
C16—H16B | 0.97 | ||
C23—O1—H1 | 109.5 | H16A—C16—H16B | 108.2 |
C21—O3—H3 | 109.5 | C16—C17—C27 | 112.4 (3) |
C14—C1—C2 | 121.4 (3) | C16—C17—C18 | 109.4 (3) |
C14—C1—C18 | 122.3 (3) | C27—C17—C18 | 114.7 (3) |
C2—C1—C18 | 115.8 (3) | C16—C17—H17A | 106.6 |
C1—C2—C3 | 116.9 (3) | C27—C17—H17A | 106.6 |
C1—C2—H2A | 108.1 | C18—C17—H17A | 106.6 |
C3—C2—H2A | 108.1 | C30—C18—C19 | 105.9 (3) |
C1—C2—H2B | 108.1 | C30—C18—C1 | 108.2 (3) |
C3—C2—H2B | 108.1 | C19—C18—C1 | 111.4 (3) |
H2A—C2—H2B | 107.3 | C30—C18—C17 | 111.8 (3) |
C2—C3—C4 | 113.3 (3) | C19—C18—C17 | 110.1 (3) |
C2—C3—H3A | 108.9 | C1—C18—C17 | 109.3 (3) |
C4—C3—H3A | 108.9 | C20—C19—C18 | 116.4 (3) |
C2—C3—H3B | 108.9 | C20—C19—H19A | 108.2 |
C4—C3—H3B | 108.9 | C18—C19—H19A | 108.2 |
H3A—C3—H3B | 107.7 | C20—C19—H19B | 108.2 |
C3—C4—C22 | 107.0 (3) | C18—C19—H19B | 108.2 |
C3—C4—C13 | 106.8 (3) | H19A—C19—H19B | 107.3 |
C22—C4—C13 | 110.4 (3) | C21—C20—C19 | 108.8 (4) |
C3—C4—C5 | 109.0 (3) | C21—C20—H20A | 109.9 |
C22—C4—C5 | 113.5 (3) | C19—C20—H20A | 109.9 |
C13—C4—C5 | 109.9 (3) | C21—C20—H20B | 109.9 |
C6—C5—C4 | 116.8 (3) | C19—C20—H20B | 109.9 |
C6—C5—C10 | 110.7 (3) | H20A—C20—H20B | 108.3 |
C4—C5—C10 | 116.6 (3) | O4—C21—O3 | 123.9 (5) |
C6—C5—H5A | 103.5 | O4—C21—C20 | 120.7 (5) |
C4—C5—H5A | 103.5 | O3—C21—C20 | 115.4 (4) |
C10—C5—H5A | 103.5 | C4—C22—H22A | 109.5 |
C7—C6—C5 | 120.4 (3) | C4—C22—H22B | 109.5 |
C7—C6—H6A | 107.2 | H22A—C22—H22B | 109.5 |
C5—C6—H6A | 107.2 | C4—C22—H22C | 109.5 |
C7—C6—H6B | 107.2 | H22A—C22—H22C | 109.5 |
C5—C6—H6B | 107.2 | H22B—C22—H22C | 109.5 |
H6A—C6—H6B | 106.9 | O2—C23—O1 | 123.4 (4) |
C23—C7—C8 | 111.1 (4) | O2—C23—C7 | 123.2 (4) |
C23—C7—C6 | 112.5 (3) | O1—C23—C7 | 113.3 (4) |
C8—C7—C6 | 111.3 (3) | C7—C24—H24A | 109.5 |
C23—C7—C24 | 104.0 (3) | C7—C24—H24B | 109.5 |
C8—C7—C24 | 109.5 (3) | H24A—C24—H24B | 109.5 |
C6—C7—C24 | 108.2 (4) | C7—C24—H24C | 109.5 |
C9—C8—C7 | 113.8 (3) | H24A—C24—H24C | 109.5 |
C9—C8—H8A | 108.8 | H24B—C24—H24C | 109.5 |
C7—C8—H8A | 108.8 | C10—C25—H25A | 109.5 |
C9—C8—H8B | 108.8 | C10—C25—H25B | 109.5 |
C7—C8—H8B | 108.8 | H25A—C25—H25B | 109.5 |
H8A—C8—H8B | 107.7 | C10—C25—H25C | 109.5 |
C8—C9—C10 | 114.6 (4) | H25A—C25—H25C | 109.5 |
C8—C9—H9A | 108.6 | H25B—C25—H25C | 109.5 |
C10—C9—H9A | 108.6 | C13—C26—H26A | 109.5 |
C8—C9—H9B | 108.6 | C13—C26—H26B | 109.5 |
C10—C9—H9B | 108.6 | H26A—C26—H26B | 109.5 |
H9A—C9—H9B | 107.6 | C13—C26—H26C | 109.5 |
C9—C10—C25 | 108.5 (3) | H26A—C26—H26C | 109.5 |
C9—C10—C11 | 109.3 (3) | H26B—C26—H26C | 109.5 |
C25—C10—C11 | 106.8 (3) | C28—C27—C29 | 120.2 (4) |
C9—C10—C5 | 110.8 (3) | C28—C27—C17 | 121.7 (4) |
C25—C10—C5 | 108.7 (3) | C29—C27—C17 | 118.0 (4) |
C11—C10—C5 | 112.6 (3) | C27—C28—H28A | 120.0 |
C12—C11—C10 | 117.1 (3) | C27—C28—H28B | 120.0 |
C12—C11—H11A | 108.0 | H28A—C28—H28B | 120.0 |
C10—C11—H11A | 108.0 | C27—C29—H29A | 109.5 |
C12—C11—H11B | 108.0 | C27—C29—H29B | 109.5 |
C10—C11—H11B | 108.0 | H29A—C29—H29B | 109.5 |
H11A—C11—H11B | 107.3 | C27—C29—H29C | 109.5 |
C11—C12—C13 | 110.8 (3) | H29A—C29—H29C | 109.5 |
C11—C12—H12A | 109.5 | H29B—C29—H29C | 109.5 |
C13—C12—H12A | 109.5 | C18—C30—H30A | 109.5 |
C11—C12—H12B | 109.5 | C18—C30—H30B | 109.5 |
C13—C12—H12B | 109.5 | H30A—C30—H30B | 109.5 |
H12A—C12—H12B | 108.1 | C18—C30—H30C | 109.5 |
C14—C13—C12 | 112.8 (3) | H30A—C30—H30C | 109.5 |
C14—C13—C26 | 103.9 (3) | H30B—C30—H30C | 109.5 |
C12—C13—C26 | 109.0 (3) | Cl4i—C31—Cl3i | 135.2 (9) |
C14—C13—C4 | 112.0 (3) | Cl1—C31—Cl1i | 129.0 (8) |
C12—C13—C4 | 106.7 (3) | Cl4i—C31—Cl3 | 99.6 (7) |
C26—C13—C4 | 112.5 (3) | Cl3i—C31—Cl3 | 123.0 (9) |
C1—C14—C15 | 122.4 (3) | Cl4i—C31—Cl4 | 67.6 (10) |
C1—C14—C13 | 121.2 (3) | Cl3i—C31—Cl4 | 92.0 (6) |
C15—C14—C13 | 116.2 (3) | Cl3—C31—Cl4 | 97.1 (6) |
C14—C15—C16 | 115.7 (3) | Cl1—C31—Cl2 | 105.1 (6) |
C14—C15—H15A | 108.3 | Cl1i—C31—Cl2 | 102.3 (6) |
C16—C15—H15A | 108.3 | Cl1—C31—H31A | 105.8 |
C14—C15—H15B | 108.3 | Cl1i—C31—H31A | 106.8 |
C16—C15—H15B | 108.3 | Cl2—C31—H31A | 106.1 |
H15A—C15—H15B | 107.4 | Cl4i—C31—H31B | 50.8 |
C15—C16—C17 | 110.0 (3) | Cl3i—C31—H31B | 114.2 |
C15—C16—H16A | 109.7 | Cl3—C31—H31B | 112.6 |
C17—C16—H16A | 109.7 | Cl4—C31—H31B | 114.0 |
C15—C16—H16B | 109.7 | Cl2—C31—H31B | 125.2 |
C17—C16—H16B | 109.7 | ||
C14—C1—C2—C3 | −1.8 (6) | C15—C16—C17—C18 | −62.5 (4) |
C18—C1—C2—C3 | 169.8 (3) | C14—C1—C18—C30 | 97.3 (4) |
C1—C2—C3—C4 | 32.3 (5) | C2—C1—C18—C30 | −74.3 (4) |
C2—C3—C4—C22 | 60.6 (4) | C14—C1—C18—C19 | −146.7 (4) |
C2—C3—C4—C13 | −57.6 (4) | C2—C1—C18—C19 | 41.7 (5) |
C2—C3—C4—C5 | −176.3 (3) | C14—C1—C18—C17 | −24.7 (5) |
C3—C4—C5—C6 | −60.2 (4) | C2—C1—C18—C17 | 163.7 (3) |
C22—C4—C5—C6 | 58.9 (4) | C16—C17—C18—C30 | −66.4 (4) |
C13—C4—C5—C6 | −176.9 (3) | C27—C17—C18—C30 | 61.0 (4) |
C3—C4—C5—C10 | 165.8 (3) | C16—C17—C18—C19 | 176.2 (3) |
C22—C4—C5—C10 | −75.1 (4) | C27—C17—C18—C19 | −56.5 (4) |
C13—C4—C5—C10 | 49.1 (4) | C16—C17—C18—C1 | 53.4 (4) |
C4—C5—C6—C7 | −94.0 (4) | C27—C17—C18—C1 | −179.2 (3) |
C10—C5—C6—C7 | 42.5 (4) | C30—C18—C19—C20 | 178.2 (4) |
C5—C6—C7—C23 | 85.3 (4) | C1—C18—C19—C20 | 60.8 (5) |
C5—C6—C7—C8 | −40.2 (5) | C17—C18—C19—C20 | −60.7 (5) |
C5—C6—C7—C24 | −160.5 (3) | C18—C19—C20—C21 | −177.8 (4) |
C23—C7—C8—C9 | −82.4 (4) | C19—C20—C21—O4 | 64.4 (7) |
C6—C7—C8—C9 | 43.8 (5) | C19—C20—C21—O3 | −113.9 (5) |
C24—C7—C8—C9 | 163.3 (3) | C8—C7—C23—O2 | −6.2 (5) |
C7—C8—C9—C10 | −55.0 (5) | C6—C7—C23—O2 | −131.8 (4) |
C8—C9—C10—C25 | −63.0 (4) | C24—C7—C23—O2 | 111.5 (5) |
C8—C9—C10—C11 | −179.1 (3) | C8—C7—C23—O1 | 177.5 (3) |
C8—C9—C10—C5 | 56.3 (4) | C6—C7—C23—O1 | 52.0 (5) |
C6—C5—C10—C9 | −47.5 (4) | C24—C7—C23—O1 | −64.8 (4) |
C4—C5—C10—C9 | 89.1 (4) | C16—C17—C27—C28 | 37.4 (5) |
C6—C5—C10—C25 | 71.6 (4) | C18—C17—C27—C28 | −88.4 (5) |
C4—C5—C10—C25 | −151.8 (3) | C16—C17—C27—C29 | −139.0 (4) |
C6—C5—C10—C11 | −170.3 (3) | C18—C17—C27—C29 | 95.2 (4) |
C4—C5—C10—C11 | −33.6 (4) | Cl4i—C31—Cl1—C31i | 116.2 (8) |
C9—C10—C11—C12 | −88.7 (4) | Cl3i—C31—Cl1—C31i | −23 (4) |
C25—C10—C11—C12 | 154.1 (4) | Cl1i—C31—Cl1—C31i | 48.8 (10) |
C5—C10—C11—C12 | 34.9 (5) | Cl3—C31—Cl1—C31i | −58.6 (5) |
C10—C11—C12—C13 | −52.2 (5) | Cl4—C31—Cl1—C31i | 48.8 (6) |
C11—C12—C13—C14 | −171.7 (3) | Cl2—C31—Cl1—C31i | −71.3 (5) |
C11—C12—C13—C26 | −56.9 (4) | Cl4i—C31—Cl2—C31i | 90 (3) |
C11—C12—C13—C4 | 64.9 (4) | Cl3i—C31—Cl2—C31i | −95.7 (11) |
C3—C4—C13—C14 | 55.0 (4) | Cl1—C31—Cl2—C31i | 72.3 (11) |
C22—C4—C13—C14 | −60.9 (4) | Cl1i—C31—Cl2—C31i | −64.2 (9) |
C5—C4—C13—C14 | 173.1 (3) | Cl3—C31—Cl2—C31i | 62.1 (10) |
C3—C4—C13—C12 | 178.9 (3) | Cl4—C31—Cl2—C31i | −18.6 (7) |
C22—C4—C13—C12 | 63.0 (4) | Cl4i—C31—Cl3—C31i | 99.5 (8) |
C5—C4—C13—C12 | −63.0 (4) | Cl3i—C31—Cl3—C31i | −65.9 (11) |
C3—C4—C13—C26 | −61.7 (4) | Cl1—C31—Cl3—C31i | 103.9 (6) |
C22—C4—C13—C26 | −177.6 (3) | Cl1i—C31—Cl3—C31i | −6.6 (11) |
C5—C4—C13—C26 | 56.4 (4) | Cl4—C31—Cl3—C31i | 31.2 (7) |
C2—C1—C14—C15 | 174.5 (3) | Cl2—C31—Cl3—C31i | −90.1 (6) |
C18—C1—C14—C15 | 3.5 (6) | Cl4i—C31—Cl4—C31i | −134.0 (15) |
C2—C1—C14—C13 | 0.2 (6) | Cl3i—C31—Cl4—C31i | 87.1 (11) |
C18—C1—C14—C13 | −170.9 (3) | Cl1—C31—Cl4—C31i | −79.0 (12) |
C12—C13—C14—C1 | −148.5 (4) | Cl1i—C31—Cl4—C31i | 101.0 (12) |
C26—C13—C14—C1 | 93.6 (4) | Cl3—C31—Cl4—C31i | −36.5 (11) |
C4—C13—C14—C1 | −28.1 (5) | Cl2—C31—Cl4—C31i | 24.5 (8) |
C12—C13—C14—C15 | 36.8 (4) | C31i—C31—Cl4—Cl4i | 134.0 (15) |
C26—C13—C14—C15 | −81.0 (4) | Cl3i—C31—Cl4—Cl4i | −138.9 (10) |
C4—C13—C14—C15 | 157.2 (3) | Cl1—C31—Cl4—Cl4i | 55.0 (7) |
C1—C14—C15—C16 | −11.2 (5) | Cl1i—C31—Cl4—Cl4i | −125.0 (10) |
C13—C14—C15—C16 | 163.4 (3) | Cl3—C31—Cl4—Cl4i | 97.5 (8) |
C14—C15—C16—C17 | 40.8 (5) | Cl2—C31—Cl4—Cl4i | 158.5 (9) |
C15—C16—C17—C27 | 168.9 (3) |
Symmetry code: (i) −x+1, −y+2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O4i | 0.82 | 1.81 | 2.621 (6) | 168 |
O3—H3···O2i | 0.82 | 1.85 | 2.670 (4) | 176 |
C22—H22B···O1 | 0.96 | 2.56 | 3.380 (5) | 144 |
Symmetry code: (i) −x+1, −y+2, z. |
Experimental details
Crystal data | |
Chemical formula | C30H46O4·0.5CHCl3 |
Mr | 530.35 |
Crystal system, space group | Orthorhombic, P21212 |
Temperature (K) | 100 |
a, b, c (Å) | 12.8950 (3), 33.7309 (8), 6.5307 (1) |
V (Å3) | 2840.59 (10) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 1.88 |
Crystal size (mm) | 0.34 × 0.28 × 0.11 |
Data collection | |
Diffractometer | Bruker APEXII DUO CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.567, 0.827 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26063, 4654, 4467 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.593 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.169, 1.09 |
No. of reflections | 4654 |
No. of parameters | 357 |
No. of restraints | 40 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.53, −0.68 |
Absolute structure | Flack (1983), 1876 Friedel pairs |
Absolute structure parameter | 0.08 (5) |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O4i | 0.82 | 1.81 | 2.621 (6) | 168 |
O3—H3···O2i | 0.82 | 1.85 | 2.670 (4) | 176 |
C22—H22B···O1 | 0.96 | 2.56 | 3.380 (5) | 144 |
Symmetry code: (i) −x+1, −y+2, z. |
Acknowledgements
ZDN, AFAA and AMSAM thank Universiti Sains Malaysia (USM) for FRGS grant No. 203/PFARMASI/671154, the research University (RU) grant No. 1001/PFARMASI/81144 and the Malaysian Ministry of Science, Technology and Innovation (MOSTI) grant No. 305/PFARMASI/613219: E Science fund. ZDN, AFAA and CSY would like to acknowledge USM for the USM Fellowship. HKF and CSY thank USM for the Research University Golden Goose grant (1001/PFIZIK/811012).
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n-Hexane extract of Sandoricum koetjape was reported previously to have cytotoxic and apoptotic properties on HCT-116 colon cancer cell line (Aisha et al., 2009). The koetjapic acid can be isolated from the stem bark of S. koetjape using column chromatography and was studied for cytotoxic activity (Kaneda et al., 1992). This compound was found to possess DNA polymerase β inhibition (Sun et al., 1999), ichthyotoxic (Ismail et al., 2003), and anti-inflammatory properties (Rasadah et al., 2004). The structure of koetjapic acid was established previously by several research groups from spectral evidence (Kaneda et al., 1992; Rasadah et al., 2004; Sun et al., 1999). Herein we describe a new simple method to purify koetjapic acid from Sandoricum koetjape. This method utilizes two steps of crystallization process but without the use of column chromatography.
The asymmetric unit of title compound, consists of one koetjapic acid molecule and half a molecule of disordered chloroform solvent (Fig. 1). The koetjapic acid contains fused four-ring system, A/B/C/D (Scheme 1). The A/B, B/C and C/D junctions adopt E/trans/cis configuration, respectively. The conformation of the ring A is intermediate between envelope and half-chair [Q = 0.516 (4) Å, θ = 131.6 (3)°, φ = 45.7 (5)°]. The ring B adopts an envelope conformation [Q = 0.509 (3) Å, θ = 52.9 (3)°, φ = 177.6 (5)°] whereas ring C and D adopt chair conformations [Q = 0.561 (3) Å, θ = 155.6 (3)°, φ = 117.8 (8)°; Q = 0.491 (4) Å, θ = 168.1 (5)°, φ = 77 (2)°] (Cremer & Pople, 1975). A weak intramolecular C22—H22B···O1 hydrogen bond is observed in the molecular structure.
The koetjapic acid molecules are linked into dimers by two pairs of intermolecular O1—H1···O4 and O3—H3···O2 hydrogen bonds (Table 1). The dimers are stacked along the c axis (Fig. 2).
The chloroform molecule is disordered over four sites in a void with twofold symmetry. In one set of symmetry-related sites, atom Cl2 lies on the twofold rotation axis and the three Cl sites [Cl1, Cl2, Cl1A; occupancy 0.60] are shared by two disorder components. In the other set of symmetry-related site, atoms Cl3 and Cl3A [occupancy 0.40] are shared by two disorder components with atoms Cl4 or Cl4A [occupancy 0.20] in each component. The chloroform solvent molecule lies in the cavity produced by the dimer.