supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

Acta Cryst. (2007). E63, o4062-o4063    [ doi:10.1107/S1600536807044339 ]

2,19-Dihydroxy-3-oxo-(2[alpha],4[alpha],19[alpha])-24-nor-olean-12-en-28-oic acid monohydrate

W. Waratchareeyakul, K. Seatyoa, S. Chantrapromma and H.-K. Fun

Abstract top

The title triterpenoid compound, C29H44O5·H2O, was isolated from Terminalia triptera. The molecule contains five fused six-membered rings, with three rings in chair, one in an envelope and one in half-chair conformations. The D and E rings are cis-fused, while the other ring junctions are trans-fused. An intramolecular O-H...O hydrogen bond generates an S(5) ring motif. In the crystal structure, the molecules are linked into a three-dimensional network by O-H...O hydrogen bonds and a weak C-H...O intermolecular interaction. The crystal structure is stabilized by intra- and intermolecular O-H...O hydrogen bonds and weak C-H...O interactions.

Comment top

Terminalia triptera is a large tree of the flowering plant family, Combretaceae, comprising around 100 species distributed throughout the tropical regions of the world. This genus takes its name from the Latin word, "terminus", referring to the fact that the leaves appear at the very tips of their shoots. Plants of this genus are known especially as a source of secondary metabolites, e.g. triterpenoids, flavonoids, alkaloids and tannins. Some of these substances have antifungal (Batawila et al., 2005), antibacterial (Malekzadeh et al., 2001), antiviral (Ahn et al., 2002; Saleem et al., 2001; Yukawa et al., 1996), antioxidant (Sabu & Kuttan, 2002), antimutagenic (Kaur et al., 2002), anticancer (Saleem et al., 2002), antidiabetic activities (Sabu & Kuttan, 2002) and some exhibit cardiac protective action (Pawar & Bhutani, 2005; Sumitra et al., 2001). In our ongoing research on finding bioactive compounds from natural products, we have examined the barks of Terminalia triptera, collected from Chantaburi province in the eastern part of Thailand. The title compound was isolated from a dichloromethane extract. It was previously isolated from the Quercus aliena Blume, Fagaceae family (Chen et al., 2006) and has shown several biological activities (Chen et al. (2006). We report here the crystal structure of the title compound.

The title molecule (Fig. 1) has five fused six-membered rings (A/B/C/D/E); the cyclohexane rings A, B and E are in standard chair conformation, cyclohexene ring C is in an envelope conformation with the puckering parameter (Cremer & Pople, 1975) Q = 0.579 (1) Å, θ = 53.5 (1)° and φ = 354.97 (17)°, atom C8 having the maximum deviation of 0.4084 (13) Å, cyclohexane ring D is in a half-chair conformation with Q = 0.502 (1) Å, θ = 150.2 (1)° and φ = 7.1 (3)°. The D and E rings are cis-fused. The other ring junctions are tran-fused. The orientation of the carboxylic acid group with respect to cyclohexane ring D is indicated by the torsion angles C16—C17—C27—O3 = -134.99 (15)° and C16—C17—C27—O4 = 48.93 (14)°. The bond lengths and angles are within normal ranges (Allen et al., 1987).

An intramolecular O1—H1O1···O2 hydrogen bond generates an S(5) ring motif (Bernstein et al., 1995). The water molecule forms an intermolecular O—H···O hydrogen bond with one of the hydroxyl groups (O1W—H1W1···O5, Fig. 1). In the crystal packing (Fig. 2), the triterpenoid molecules are linked with the water molecule by O—H···O hydrogen bonds, forming sheets parallel to the bc plane and these sheets are further connected into a three dimensional network by O—H···O hydrogen bonds and weak C—H···O interactions (Fig. 2 and Table 1). The crystal structure is stabilized by intra- and intermolecular O—H···O hydrogen bonds and weak C—H···O intramolecular interactions (Table 1).

Related literature top

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For related literature on values of bond lengths, see: Allen et al. (1987). For related literature on ring conformations, see: Cremer & Pople (1975). For related structures, see: e.g. Chantrapromma et al. (2003); Chen et al. (2006); Rahman et al. (2002). For related literature on alkaloids, flavanoids, triterpenoids and their biological activities, see: e.g. Ahn et al. (2002); Batawila et al. (2005); Chen et al. (2006); Malekzadeh et al. (2001); Pawar & Bhutani (2005); Kaur et al. (2002); Rahman et al. (2002); Sabu & Kuttan (2002); Saleem et al. (2001, 2002); Sumitra et al. (2001); Yukawa et al. (1996).

Experimental top

Air-dried barks of Terminalia triptera (5.2 kg) were extracted with hexane, CH2Cl2 and MeOH, successively. The CH2Cl2 extract was dried under reduced pressure to yield a crude extract (13.50 g) which was subjected to quick column chromatography (QCC) over silica gel and eluted initially with CH2Cl2 enriched with EtOAc, followed by an increasing amount of MeOH in EtOAc and finally with MeOH. The eluents were separated into 11 fractions (F1—F11) on the basis of TLC analysis. Fraction F7 (1.25 g) was separated by QCC over silica gel and eluted initially with EtOAc:hexane (2:3 v/v), to give 6 fractions (F7A—F7F). Fraction F7B was further purified by crystallization to give the title compound (0.1691 g). Colorless single crystals of the title compound were recrystallized from hexane:CH2Cl2:EtOAC (3:3:4 v/v) after a few days (M.p. 512–514 K).

Refinement top

Water and hydroxyl H atoms were located in a difference map whereas the remaining H atoms were positioned geometrically. All hydrogen atoms were allowed to ride on their parent atoms, with the C—H distances in the range 0.93 - 0.98 Å and O—H in the range 0.75 - 0.91 Å. The Uiso(H) values were set equal to 1.5Ueq of the carrier atom for methyl, hydroxyl and water H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. A total of 4444 Friedel pairs were merged before the final refinement as there are no significant anomalous dispersion effects. The configuration was assigned on the basis of the earlier literature absolute configuration (Chen et al., 2006).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering scheme. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are drawn as dashed lines.
2,19-Dihydroxy-3-oxo-(2α,4α,19α)-24-nor-olean-12-en-28-oic acid monohydrate top
Crystal data top
C29H44O5·H2ODx = 1.255 Mg m−3
Mr = 490.66Melting point: 512-514 K K
Orthorhombic, P212121Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5485 reflections
a = 11.8983 (3) Åθ = 2.0–33.2º
b = 14.3772 (3) ŵ = 0.09 mm−1
c = 15.1835 (3) ÅT = 100.0 (1) K
V = 2597.35 (10) Å3Block, colorless
Z = 40.58 × 0.41 × 0.18 mm
F000 = 1072
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		5485 independent reflections
Radiation source: fine-focus sealed tube5078 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
Detector resolution: 8.33 pixels mm-1θmax = 33.2º
T = 100.0(1) Kθmin = 2.0º
ω scansh = −17→18
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −14→22
Tmin = 0.952, Tmax = 0.985l = −22→23
37602 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.110  w = 1/[σ2(Fo2) + (0.0714P)2 + 0.3157P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
5485 reflectionsΔρmax = 0.33 e Å−3
322 parametersΔρmin = −0.43 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C29H44O5·H2OV = 2597.35 (10) Å3
Mr = 490.66Z = 4
Orthorhombic, P212121Mo Kα
a = 11.8983 (3) ŵ = 0.09 mm−1
b = 14.3772 (3) ÅT = 100.0 (1) K
c = 15.1835 (3) Å0.58 × 0.41 × 0.18 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		5485 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		5078 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 0.985Rint = 0.037
37602 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039Δρmax = 0.33 e Å−3
wR(F2) = 0.110Δρmin = −0.43 e Å−3
S = 1.04Absolute structure: ?
5485 reflectionsFlack parameter: ?
322 parametersRogers parameter: ?
H-atom parameters constrained
Special details top

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
O10.51439 (10)0.09740 (7)0.38914 (7)0.0204 (2)
H1O10.45470.08450.37840.031*
O20.36546 (11)0.22455 (9)0.33128 (8)0.0268 (2)
O30.52258 (9)0.37362 (9)1.00414 (8)0.0238 (2)
O40.37219 (9)0.45694 (8)1.04344 (8)0.0229 (2)
H1O40.41320.49501.06470.034*
O50.24247 (9)0.10261 (8)0.94160 (7)0.0207 (2)
H1O50.18260.11460.96920.031*
O1W0.18414 (14)−0.03114 (10)0.83170 (10)0.0392 (3)
H1W10.21350.01530.85970.059*
H2W10.2348−0.07800.82840.059*
C10.48950 (11)0.17482 (9)0.53030 (8)0.0149 (2)
H1A0.55030.13940.55650.018*
H1B0.42080.13950.53830.018*
C20.51212 (12)0.18495 (10)0.43130 (9)0.0167 (2)
H2A0.58630.21360.42410.020*
C30.42575 (12)0.24988 (10)0.39091 (9)0.0173 (2)
C40.41499 (12)0.34438 (9)0.43416 (9)0.0164 (2)
H4A0.48780.37600.43060.020*
C50.38724 (10)0.32674 (9)0.53292 (9)0.0141 (2)
H5A0.31830.28950.53380.017*
C60.36119 (12)0.41553 (9)0.58430 (9)0.0169 (2)
H6A0.30690.45250.55200.020*
H6B0.42920.45210.59080.020*
C70.31401 (11)0.39177 (9)0.67552 (9)0.0163 (2)
H7A0.24160.36170.66820.020*
H7B0.30170.44910.70770.020*
C80.39051 (10)0.32789 (9)0.73082 (8)0.0133 (2)
C90.43285 (11)0.24511 (9)0.67389 (9)0.0139 (2)
H9A0.36590.20690.66360.017*
C100.47826 (11)0.26784 (9)0.57986 (8)0.0134 (2)
C110.51232 (13)0.18212 (10)0.72738 (9)0.0192 (3)
H11A0.50690.11920.70470.023*
H11B0.58890.20310.71840.023*
C120.48871 (11)0.18022 (10)0.82437 (9)0.0159 (2)
H12A0.53620.14440.85920.019*
C130.40569 (10)0.22535 (9)0.86518 (8)0.0132 (2)
C140.32271 (10)0.28331 (9)0.81068 (8)0.0131 (2)
C150.26629 (11)0.36017 (9)0.86653 (9)0.0152 (2)
H15A0.31710.41270.87070.018*
H15B0.19900.38110.83640.018*
C160.23455 (10)0.32886 (9)0.95957 (9)0.0151 (2)
H16A0.18180.27760.95610.018*
H16B0.19820.37970.99040.018*
C170.33939 (10)0.29809 (9)1.01102 (8)0.0135 (2)
C180.39615 (10)0.21458 (9)0.96506 (8)0.0135 (2)
H18A0.47350.21300.98720.016*
C190.34447 (11)0.11884 (10)0.98870 (9)0.0156 (2)
H19A0.39800.07180.96820.019*
C200.32994 (11)0.10269 (10)1.08802 (9)0.0168 (2)
C210.25994 (11)0.18336 (10)1.12574 (9)0.0166 (2)
H21A0.18580.18221.09930.020*
H21B0.25100.17431.18870.020*
C220.31287 (11)0.27781 (10)1.10947 (9)0.0159 (2)
H22A0.38210.28191.14300.019*
H22B0.26250.32561.13130.019*
C230.32822 (13)0.40318 (10)0.38653 (10)0.0211 (3)
H23A0.34460.40380.32460.032*
H23B0.33040.46560.40890.032*
H23C0.25480.37740.39590.032*
C240.59359 (11)0.31730 (10)0.57976 (9)0.0177 (2)
H24A0.62170.32060.52060.027*
H24B0.64540.28300.61570.027*
H24C0.58530.37900.60300.027*
C250.48953 (11)0.38732 (10)0.76549 (9)0.0170 (2)
H25A0.50990.43270.72200.025*
H25B0.55280.34780.77730.025*
H25C0.46730.41830.81870.025*
C260.22587 (11)0.21961 (10)0.77842 (9)0.0169 (2)
H26A0.17490.20800.82620.025*
H26B0.25640.16170.75790.025*
H26C0.18640.24970.73120.025*
C270.42208 (11)0.37913 (10)1.01693 (9)0.0156 (2)
C280.44652 (12)0.09760 (11)1.13187 (10)0.0212 (3)
H28A0.48920.04811.10580.032*
H28B0.43770.08611.19380.032*
H28C0.48530.15551.12340.032*
C290.26903 (14)0.01038 (11)1.10450 (10)0.0230 (3)
H29A0.19340.01461.08290.034*
H29B0.2679−0.00251.16650.034*
H29C0.3077−0.03881.07430.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0267 (5)0.0164 (4)0.0182 (4)0.0060 (4)−0.0010 (4)−0.0018 (4)
O20.0336 (6)0.0244 (5)0.0225 (5)0.0055 (5)−0.0084 (5)−0.0024 (4)
O30.0131 (4)0.0263 (5)0.0321 (6)−0.0038 (4)0.0029 (4)−0.0081 (5)
O40.0185 (4)0.0162 (4)0.0341 (6)−0.0015 (4)−0.0005 (4)−0.0079 (4)
O50.0165 (4)0.0246 (5)0.0209 (4)−0.0043 (4)−0.0010 (4)−0.0027 (4)
O1W0.0420 (8)0.0329 (7)0.0428 (8)−0.0038 (6)−0.0015 (6)−0.0116 (6)
C10.0170 (5)0.0136 (5)0.0141 (5)0.0030 (4)0.0008 (4)0.0015 (4)
C20.0195 (6)0.0151 (5)0.0157 (5)0.0031 (5)0.0010 (4)0.0007 (4)
C30.0209 (6)0.0153 (5)0.0158 (5)0.0025 (5)0.0008 (4)0.0032 (4)
C40.0177 (5)0.0138 (5)0.0176 (5)0.0020 (4)−0.0016 (4)0.0025 (4)
C50.0133 (5)0.0133 (5)0.0157 (5)0.0027 (4)−0.0013 (4)0.0009 (4)
C60.0191 (5)0.0122 (5)0.0193 (5)0.0040 (4)−0.0009 (5)0.0015 (4)
C70.0164 (5)0.0137 (5)0.0189 (5)0.0049 (4)−0.0015 (4)−0.0006 (4)
C80.0122 (5)0.0117 (5)0.0161 (5)0.0016 (4)−0.0016 (4)−0.0013 (4)
C90.0145 (5)0.0121 (5)0.0152 (5)0.0029 (4)−0.0001 (4)0.0002 (4)
C100.0130 (5)0.0118 (5)0.0154 (5)0.0020 (4)−0.0009 (4)0.0009 (4)
C110.0227 (6)0.0199 (6)0.0149 (5)0.0108 (5)0.0021 (5)0.0024 (5)
C120.0158 (5)0.0165 (5)0.0156 (5)0.0045 (4)−0.0002 (4)0.0006 (4)
C130.0117 (5)0.0134 (5)0.0146 (5)0.0015 (4)−0.0007 (4)−0.0015 (4)
C140.0117 (5)0.0123 (5)0.0153 (5)0.0020 (4)−0.0005 (4)−0.0021 (4)
C150.0130 (5)0.0148 (5)0.0179 (5)0.0031 (4)−0.0008 (4)−0.0027 (4)
C160.0110 (5)0.0161 (5)0.0183 (5)0.0012 (4)0.0006 (4)−0.0028 (5)
C170.0104 (5)0.0146 (5)0.0154 (5)0.0002 (4)0.0003 (4)−0.0024 (4)
C180.0119 (5)0.0139 (5)0.0145 (5)0.0019 (4)0.0003 (4)−0.0016 (4)
C190.0135 (5)0.0154 (5)0.0178 (5)−0.0001 (4)0.0007 (4)−0.0015 (4)
C200.0158 (5)0.0172 (6)0.0174 (5)−0.0011 (5)0.0004 (4)0.0009 (5)
C210.0142 (5)0.0196 (6)0.0161 (5)−0.0004 (5)0.0025 (4)−0.0003 (5)
C220.0139 (5)0.0184 (5)0.0154 (5)−0.0006 (5)0.0011 (4)−0.0025 (4)
C230.0240 (6)0.0185 (6)0.0206 (6)0.0042 (5)−0.0050 (5)0.0043 (5)
C240.0132 (5)0.0186 (6)0.0213 (6)0.0002 (4)−0.0018 (4)0.0015 (5)
C250.0147 (5)0.0170 (5)0.0192 (5)−0.0005 (5)−0.0015 (4)−0.0011 (5)
C260.0149 (5)0.0178 (6)0.0181 (5)−0.0008 (5)−0.0021 (4)−0.0026 (5)
C270.0157 (5)0.0161 (5)0.0149 (5)−0.0007 (5)−0.0001 (4)−0.0024 (4)
C280.0185 (6)0.0242 (6)0.0211 (6)0.0032 (5)−0.0007 (5)0.0023 (5)
C290.0268 (7)0.0178 (6)0.0244 (6)−0.0036 (5)0.0032 (5)0.0017 (5)
Geometric parameters (Å, °) top
O1—C21.4123 (17)C13—C141.5343 (18)
O1—H1O10.7517C14—C151.5463 (18)
O2—C31.2112 (18)C14—C261.5511 (19)
O3—C271.2140 (17)C15—C161.5301 (19)
O4—C271.3288 (17)C15—H15A0.9700
O4—H1O40.8017C15—H15B0.9700
O5—C191.4279 (17)C16—C171.5369 (18)
O5—H1O50.8436C16—H16A0.9700
O1W—H1W10.8654C16—H16B0.9700
O1W—H2W10.9063C17—C271.5275 (19)
C1—C21.5340 (19)C17—C181.5443 (18)
C1—C101.5403 (19)C17—C221.5553 (18)
C1—H1A0.9700C18—C191.5497 (19)
C1—H1B0.9700C18—H18A0.9800
C2—C31.5177 (19)C19—C201.5356 (19)
C2—H2A0.9800C19—H19A0.9800
C3—C41.514 (2)C20—C291.533 (2)
C4—C231.5178 (19)C20—C211.5385 (19)
C4—C51.5561 (18)C20—C281.540 (2)
C4—H4A0.9800C21—C221.517 (2)
C5—C61.5279 (19)C21—H21A0.9700
C5—C101.5487 (17)C21—H21B0.9700
C5—H5A0.9800C22—H22A0.9700
C6—C71.5331 (19)C22—H22B0.9700
C6—H6A0.9700C23—H23A0.9600
C6—H6B0.9700C23—H23B0.9600
C7—C81.5418 (18)C23—H23C0.9600
C7—H7A0.9700C24—H24A0.9600
C7—H7B0.9700C24—H24B0.9600
C8—C251.5477 (19)C24—H24C0.9600
C8—C91.5548 (18)C25—H25A0.9600
C8—C141.5912 (18)C25—H25B0.9600
C9—C111.5408 (19)C25—H25C0.9600
C9—C101.5610 (18)C26—H26A0.9600
C9—H9A0.9800C26—H26B0.9600
C10—C241.5456 (18)C26—H26C0.9600
C11—C121.4995 (19)C28—H28A0.9600
C11—H11A0.9700C28—H28B0.9600
C11—H11B0.9700C28—H28C0.9600
C12—C131.3344 (18)C29—H29A0.9600
C12—H12A0.9300C29—H29B0.9600
C13—C181.5287 (18)C29—H29C0.9600
C2—O1—H1O1107.5C14—C15—H15B108.8
C27—O4—H1O4115.2H15A—C15—H15B107.7
C19—O5—H1O5115.8C15—C16—C17110.71 (10)
H1W1—O1W—H2W1109.4C15—C16—H16A109.5
C2—C1—C10114.31 (11)C17—C16—H16A109.5
C2—C1—H1A108.7C15—C16—H16B109.5
C10—C1—H1A108.7C17—C16—H16B109.5
C2—C1—H1B108.7H16A—C16—H16B108.1
C10—C1—H1B108.7C27—C17—C16109.46 (11)
H1A—C1—H1B107.6C27—C17—C18109.75 (10)
O1—C2—C3112.21 (11)C16—C17—C18110.43 (10)
O1—C2—C1111.28 (11)C27—C17—C22102.55 (10)
C3—C2—C1109.60 (11)C16—C17—C22112.20 (10)
O1—C2—H2A107.9C18—C17—C22112.16 (11)
C3—C2—H2A107.9C13—C18—C17113.70 (11)
C1—C2—H2A107.9C13—C18—C19110.44 (11)
O2—C3—C4122.94 (13)C17—C18—C19114.36 (11)
O2—C3—C2121.21 (13)C13—C18—H18A105.8
C4—C3—C2115.71 (11)C17—C18—H18A105.8
C3—C4—C23110.52 (11)C19—C18—H18A105.8
C3—C4—C5106.83 (10)O5—C19—C20111.80 (11)
C23—C4—C5113.93 (11)O5—C19—C18111.49 (11)
C3—C4—H4A108.5C20—C19—C18113.98 (11)
C23—C4—H4A108.5O5—C19—H19A106.3
C5—C4—H4A108.5C20—C19—H19A106.3
C6—C5—C10111.33 (11)C18—C19—H19A106.3
C6—C5—C4113.51 (11)C29—C20—C19110.15 (11)
C10—C5—C4112.60 (10)C29—C20—C21109.64 (11)
C6—C5—H5A106.3C19—C20—C21108.21 (11)
C10—C5—H5A106.3C29—C20—C28108.31 (12)
C4—C5—H5A106.3C19—C20—C28109.28 (11)
C5—C6—C7110.45 (11)C21—C20—C28111.25 (11)
C5—C6—H6A109.6C22—C21—C20112.92 (11)
C7—C6—H6A109.6C22—C21—H21A109.0
C5—C6—H6B109.6C20—C21—H21A109.0
C7—C6—H6B109.6C22—C21—H21B109.0
H6A—C6—H6B108.1C20—C21—H21B109.0
C6—C7—C8114.11 (11)H21A—C21—H21B107.8
C6—C7—H7A108.7C21—C22—C17114.11 (11)
C8—C7—H7A108.7C21—C22—H22A108.7
C6—C7—H7B108.7C17—C22—H22A108.7
C8—C7—H7B108.7C21—C22—H22B108.7
H7A—C7—H7B107.6C17—C22—H22B108.7
C7—C8—C25107.81 (11)H22A—C22—H22B107.6
C7—C8—C9110.15 (10)C4—C23—H23A109.5
C25—C8—C9111.42 (10)C4—C23—H23B109.5
C7—C8—C14110.83 (10)H23A—C23—H23B109.5
C25—C8—C14110.43 (10)C4—C23—H23C109.5
C9—C8—C14106.24 (10)H23A—C23—H23C109.5
C11—C9—C8110.83 (10)H23B—C23—H23C109.5
C11—C9—C10113.12 (10)C10—C24—H24A109.5
C8—C9—C10117.41 (10)C10—C24—H24B109.5
C11—C9—H9A104.7H24A—C24—H24B109.5
C8—C9—H9A104.7C10—C24—H24C109.5
C10—C9—H9A104.7H24A—C24—H24C109.5
C1—C10—C24108.77 (11)H24B—C24—H24C109.5
C1—C10—C5108.10 (10)C8—C25—H25A109.5
C24—C10—C5111.64 (11)C8—C25—H25B109.5
C1—C10—C9107.17 (10)H25A—C25—H25B109.5
C24—C10—C9113.86 (11)C8—C25—H25C109.5
C5—C10—C9107.06 (10)H25A—C25—H25C109.5
C12—C11—C9114.43 (11)H25B—C25—H25C109.5
C12—C11—H11A108.7C14—C26—H26A109.5
C9—C11—H11A108.7C14—C26—H26B109.5
C12—C11—H11B108.7H26A—C26—H26B109.5
C9—C11—H11B108.7C14—C26—H26C109.5
H11A—C11—H11B107.6H26A—C26—H26C109.5
C13—C12—C11125.86 (12)H26B—C26—H26C109.5
C13—C12—H12A117.1O3—C27—O4122.91 (13)
C11—C12—H12A117.1O3—C27—C17125.12 (13)
C12—C13—C18117.80 (11)O4—C27—C17111.85 (11)
C12—C13—C14119.34 (11)C20—C28—H28A109.5
C18—C13—C14122.84 (11)C20—C28—H28B109.5
C13—C14—C15111.82 (10)H28A—C28—H28B109.5
C13—C14—C26109.13 (11)C20—C28—H28C109.5
C15—C14—C26105.82 (10)H28A—C28—H28C109.5
C13—C14—C8107.67 (10)H28B—C28—H28C109.5
C15—C14—C8110.49 (10)C20—C29—H29A109.5
C26—C14—C8111.95 (10)C20—C29—H29B109.5
C16—C15—C14113.78 (11)H29A—C29—H29B109.5
C16—C15—H15A108.8C20—C29—H29C109.5
C14—C15—H15A108.8H29A—C29—H29C109.5
C16—C15—H15B108.8H29B—C29—H29C109.5
C10—C1—C2—O1−176.29 (11)C18—C13—C14—C8146.80 (12)
C10—C1—C2—C3−51.58 (15)C7—C8—C14—C13−176.92 (10)
O1—C2—C3—O22.22 (19)C25—C8—C14—C13−57.52 (13)
C1—C2—C3—O2−121.94 (15)C9—C8—C14—C1363.43 (12)
O1—C2—C3—C4178.06 (11)C7—C8—C14—C15−54.54 (13)
C1—C2—C3—C453.89 (16)C25—C8—C14—C1564.86 (13)
O2—C3—C4—C23−5.55 (19)C9—C8—C14—C15−174.19 (10)
C2—C3—C4—C23178.69 (12)C7—C8—C14—C2663.13 (13)
O2—C3—C4—C5118.89 (15)C25—C8—C14—C26−177.47 (11)
C2—C3—C4—C5−56.86 (15)C9—C8—C14—C26−56.51 (13)
C3—C4—C5—C6−173.84 (11)C13—C14—C15—C16−40.20 (15)
C23—C4—C5—C6−51.50 (15)C26—C14—C15—C1678.51 (13)
C3—C4—C5—C1058.52 (14)C8—C14—C15—C16−160.11 (10)
C23—C4—C5—C10−179.14 (11)C14—C15—C16—C1760.46 (14)
C10—C5—C6—C7−62.08 (14)C15—C16—C17—C2759.55 (13)
C4—C5—C6—C7169.63 (11)C15—C16—C17—C18−61.38 (14)
C5—C6—C7—C855.68 (15)C15—C16—C17—C22172.70 (10)
C6—C7—C8—C2575.38 (14)C12—C13—C18—C17153.38 (12)
C6—C7—C8—C9−46.38 (15)C14—C13—C18—C17−28.20 (17)
C6—C7—C8—C14−163.66 (11)C12—C13—C18—C19−76.50 (15)
C7—C8—C9—C11178.31 (11)C14—C13—C18—C19101.92 (14)
C25—C8—C9—C1158.72 (14)C27—C17—C18—C13−76.40 (13)
C14—C8—C9—C11−61.60 (13)C16—C17—C18—C1344.36 (14)
C7—C8—C9—C1046.19 (15)C22—C17—C18—C13170.31 (10)
C25—C8—C9—C10−73.40 (14)C27—C17—C18—C19155.47 (11)
C14—C8—C9—C10166.28 (10)C16—C17—C18—C19−83.77 (13)
C2—C1—C10—C24−67.31 (14)C22—C17—C18—C1942.18 (14)
C2—C1—C10—C554.09 (14)C13—C18—C19—O5−51.30 (14)
C2—C1—C10—C9169.17 (11)C17—C18—C19—O578.47 (14)
C6—C5—C10—C1173.37 (11)C13—C18—C19—C20−179.04 (11)
C4—C5—C10—C1−57.84 (14)C17—C18—C19—C20−49.27 (15)
C6—C5—C10—C24−67.03 (14)O5—C19—C20—C2947.44 (16)
C4—C5—C10—C2461.76 (14)C18—C19—C20—C29175.01 (11)
C6—C5—C10—C958.22 (14)O5—C19—C20—C21−72.40 (14)
C4—C5—C10—C9−173.00 (10)C18—C19—C20—C2155.18 (14)
C11—C9—C10—C161.30 (14)O5—C19—C20—C28166.31 (12)
C8—C9—C10—C1−167.62 (10)C18—C19—C20—C28−66.11 (15)
C11—C9—C10—C24−59.03 (15)C29—C20—C21—C22−178.15 (12)
C8—C9—C10—C2472.05 (14)C19—C20—C21—C22−58.00 (14)
C11—C9—C10—C5177.08 (11)C28—C20—C21—C2262.07 (15)
C8—C9—C10—C5−51.85 (14)C20—C21—C22—C1754.74 (15)
C8—C9—C11—C1229.61 (17)C27—C17—C22—C21−162.94 (11)
C10—C9—C11—C12163.88 (12)C16—C17—C22—C2179.71 (14)
C9—C11—C12—C131.8 (2)C18—C17—C22—C21−45.27 (14)
C11—C12—C13—C18−179.78 (13)C16—C17—C27—O3−134.99 (15)
C11—C12—C13—C141.7 (2)C18—C17—C27—O3−13.65 (19)
C12—C13—C14—C15−156.36 (12)C22—C17—C27—O3105.72 (16)
C18—C13—C14—C1525.24 (17)C16—C17—C27—O448.93 (14)
C12—C13—C14—C2686.91 (15)C18—C17—C27—O4170.28 (11)
C18—C13—C14—C26−91.48 (14)C22—C17—C27—O4−70.35 (14)
C12—C13—C14—C8−34.81 (16)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···O20.752.392.6933 (17)106
O1—H1O1···O1Wi0.751.962.692 (2)167
O1W—H1W1···O50.871.802.6389 (19)163
O4—H1O4···O1ii0.801.842.6357 (16)169
O5—H1O5···O3iii0.841.952.7642 (15)161
O1W—H2W1···O2iv0.912.422.8426 (19)109
C6—H6A···O4v0.972.503.3849 (18)152
C18—H18A···O30.982.402.8006 (18)104
C26—H26A···O50.962.453.0012 (18)116
Symmetry codes: (i) −x+1/2, −y, z−1/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x−1/2, −y+1/2, −z+2; (iv) −x+1/2, −y, z+1/2; (v) −x+1/2, −y+1, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···O20.752.392.6933 (17)106
O1—H1O1···O1Wi0.751.962.692 (2)167
O1W—H1W1···O50.871.802.6389 (19)163
O4—H1O4···O1ii0.801.842.6357 (16)169
O5—H1O5···O3iii0.841.952.7642 (15)161
O1W—H2W1···O2iv0.912.422.8426 (19)109
C6—H6A···O4v0.972.503.3849 (18)152
C18—H18A···O30.982.402.8006 (18)104
C26—H26A···O50.962.453.0012 (18)116
Symmetry codes: (i) −x+1/2, −y, z−1/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x−1/2, −y+1/2, −z+2; (iv) −x+1/2, −y, z+1/2; (v) −x+1/2, −y+1, z−1/2.
Acknowledgements top

WW and KS thank Rambhai Barni Rajabhat University for financial support. The authors also thank the Prince of Songkla University, the Malaysian Government and Universiti Sains Malaysia for Scientific Advancement Grant Allocation (SAGA) No. 304/PFIZIK/653003/A118.

references
References top

Ahn, M. J., Kim, C. Y., Lee, J. S., Kim, T. G., Kim, S. H., Lee, C. K., Lee, B. B., Shin, C. G., Huh, H. & Kim, J. (2002). Planta Med. 68, 457–459.

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Batawila, K., Kokou, K., Koumaglo, K., Gbeassor, M., de Foucault, B., Bouchet, Ph. & Akpagana, K. (2005). Fitoterapia, 76, 264–268.

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.

Bruker (2005). APEX2 (Version 1.27), SAINT (Version 7.12a) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.

Chantrapromma, S., Fun, H.-K., Razak, I. A., Laphookhieo, S. & Karalai, C. (2003). Acta Cryst. E59, o1864–o1866.

Chen, H.-D., Yang, S.-P., Liao, S.-G., Zhang, C.-R. & Yue, J.-M. (2006). Helv. Chim. Acta, 89, 1971–1977.

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.

Kaur, K., Arora, S., Kumar, S. & Nagpal, A. (2002). Food Chem. Toxicol. 40, 1475–1482.

Malekzadeh, F., Ehsanifar, H., Shahamat, M., Levin, M. & Colwell, R. R. (2001). Int. J. Antimicrob. Agents, 18, 85–88.

Pawar, R. S. & Bhutani, K. K. (2005). Phytomedicine, 12, 391–393.

Rahman, A., Zareen, S., Choudhary, M. I., Ngounou, F. N., Yasin, A. & Parvez, M. (2002). Tetrahedron Lett. 43, 6233–6236.

Sabu, M. C. & Kuttan, R. (2002). J. Ethnopharmacol. 81, 155–160.

Saleem, A., Ahotupa, M. & Pihlaja, K. (2001). Z. Naturforsch. Teil A, B or C? 56, 973–978.

Saleem, A., Husheem, M., Harkonen, P. & Pihlaja, K. (2002). J. Ethnopharmacol. 81, 327–336.

Sheldrick, G. M. (1998). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Sumitra, M., Manikandan, P., Kumar, D. A., Arutselvan, N., Balakrishna, K., Manohar, B. M. & Puvanakrishnan, R. (2001). Mol. Cell. Biochem. 224, 135–142.

Yukawa, T. A., Kurokawa, M., Sato, H., Yoshida, Y., Kageyama, S., Hasegawa, T., Namba, T., Imakita, M., Hozumi, T. & Shiraki, K. (1996). Antiviral Res. 32, 63–70.