PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o854–o855.
Published online 2010 March 17. doi:  10.1107/S1600536810007646
PMCID: PMC2983995

Bruceine A

Abstract

The title compound, C26H34O11, known as bruceine A, is a natural quassinoid extracted from the dried fruits of Brucea javanica. Its structure consists of five fused rings including an oxygen-containing heterocyclic ring and a lactone ring. Two intra­molecular O—H(...)O links help to establish the mol­ecular conformation. In the crystal, O—H(...)O hydrogen bonds connect the mol­ecules.

Related literature

For medicinal and pharmacological background to Brucea javanica and its extracts, see: Anderson et al. (1991 [triangle]); Bawm et al. (2008 [triangle]); Elkhateeb et al. (2008 [triangle]); Klocke et al. (1985 [triangle]); Leskinen et al. (1984 [triangle]); Nakao et al. (2009 [triangle]); O’Neill et al. (1987 [triangle]); Odjo et al. (1981 [triangle]); Pan et al. (2009 [triangle]); Pavanand et al. (1986 [triangle]); Subeki et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o854-scheme1.jpg

Experimental

Crystal data

  • C26H34O11
  • M r = 522.53
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o854-efi1.jpg
  • a = 9.0337 (12) Å
  • b = 10.167 (3) Å
  • c = 26.9122 (11) Å
  • V = 2471.8 (8) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 0.92 mm−1
  • T = 173 K
  • 0.44 × 0.30 × 0.14 mm

Data collection

  • Rigaku R-AXIS RAPID IP area-detector diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.687, T max = 0.882
  • 17108 measured reflections
  • 4478 independent reflections
  • 4051 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.098
  • S = 1.13
  • 4478 reflections
  • 340 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.21 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1887 Friedel pairs
  • Flack parameter: −0.3 (2)

Data collection: RAPID-AUTO (Rigaku, 2001 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007646/hb5331sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007646/hb5331Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Projects in the National Science & Technology Pillar Program in the Eleventh Five-year Plan Period (2006BAD08A03).

supplementary crystallographic information

Comment

The bitter fruits of medicinal plant Brucea javanica (L.) Merr. Simaroubaceae is widely used in traditional medicine for various ailments (Bawm et al., 2008). Bruceine A, a natural quassinoid compound extracted from the fruits of B. javanica (L.) Merr., with a wide spectrum of biological effects, such as having potential antibabesial,antitrypanosomal, antimalarial and cytotoxicity against human cancer cell lines (Pan et al., 2009; Nakao et al., 2009; Elkhateeb et al., 2008; Subeki et al., 2007; Anderson et al.,1991; O'Neill et al.,1987; Pavanand et al.,1986). Bruceine A was also shown to have insecticidal, antifeedant, and growth inhibitory effects against the tobacco budworm, Heliothis virescens (F.), and the fall armyworm, Spodoptera frugiperda (Klocke et al., 1985), and strong antifeedant activity on the 3rd larvae of Locusta migratoria migratorioides R and F (Orthoptera, Acrididae) (Odjo et al.,1981) and the 4th instar larvae of Mexican bean beetle (Epilachna varivestis Mulsant) (Leskinen et al.,1984).

As part of our studies in this area, we have isolated the title compound (I), which has potential insecticidal activity against Spodoptera exigua (Lepidoptera: Noctuidae). The crystal structure of the title compound is shown in Fig. 1.

Experimental

The dried fruits of B. javanica were extracted with 80% ethanol for three days. Then the solution was filtered and removed into vacuo, and extracted with CHCl3 to give aqueous and CHCl3 layers. The CHCl3 layer was chromatographed on a silica gel column, and eluted successively with different MeOH–CHCl3 ratios. The MeOH–CHCl3 (20:80) eluate was evaporated to yield a residue, which was subjected to column chromatography on silica gel, eluted with hexane–EtOAc (50:50), to give the title compound (Bruceine A). The title compound was dissolved in acetone (20 ml) at room temperature, Colourless plates of (I) were obtained through slow evaporation after two weeks.

Refinement

All the hydrogen atoms were placed at their geometrical positions (C—H = 0.93–0.98Å; O–H = 0.84Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C,O).

Figures

Fig. 1.
Ellipsoid plot.

Crystal data

C26H34O11F(000) = 1112
Mr = 522.53Dx = 1.404 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54186 Å
Hall symbol: P 2ac 2abCell parameters from 657 reflections
a = 9.0337 (12) Åθ = 3.1–66.2°
b = 10.167 (3) ŵ = 0.92 mm1
c = 26.9122 (11) ÅT = 173 K
V = 2471.8 (8) Å3Plate, colourless
Z = 40.44 × 0.30 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer4478 independent reflections
Radiation source: rotating anode4051 reflections with I > 2σ(I)
graphiteRint = 0.044
ω scans at fixed χ = 45°θmax = 68.2°, θmin = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −10→10
Tmin = 0.687, Tmax = 0.882k = −11→12
17108 measured reflectionsl = −32→32

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044w = 1/[σ2(Fo2) + (0.0199P)2 + 1.6367P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098(Δ/σ)max < 0.001
S = 1.13Δρmax = 0.21 e Å3
4478 reflectionsΔρmin = −0.21 e Å3
340 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.00127 (11)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1887 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.3 (2)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.7087 (2)0.7346 (2)0.58066 (7)0.0362 (5)
O20.4645 (2)0.6705 (2)0.63450 (7)0.0372 (5)
H2A0.54790.69620.64440.056*
O30.1686 (2)0.4600 (2)0.42513 (6)0.0261 (5)
O40.0274 (2)0.5360 (2)0.36490 (7)0.0308 (5)
O50.5773 (2)0.64791 (18)0.32956 (6)0.0241 (4)
H5A0.56100.64360.29890.036*
O60.7799 (2)0.4626 (2)0.42098 (7)0.0292 (5)
H6A0.85950.47790.40600.044*
O70.6075 (2)0.29438 (18)0.35876 (6)0.0248 (5)
O80.2473 (2)0.51955 (19)0.29566 (6)0.0224 (4)
O90.1862 (2)0.73521 (19)0.29790 (7)0.0284 (5)
O100.4926 (2)0.26506 (19)0.26475 (6)0.0308 (5)
O110.5696 (2)0.47209 (19)0.24965 (6)0.0274 (5)
C10.6047 (4)0.6833 (3)0.55833 (10)0.0283 (7)
C20.4716 (3)0.6417 (3)0.58506 (10)0.0268 (6)
C30.3604 (3)0.5767 (3)0.56249 (10)0.0238 (6)
C40.3724 (3)0.5357 (3)0.50844 (9)0.0209 (6)
H4A0.31810.60350.48860.025*
C50.5338 (3)0.5333 (3)0.48864 (9)0.0200 (5)
C60.6068 (3)0.6646 (3)0.50295 (9)0.0237 (6)
H6B0.71040.66580.49090.028*
H6C0.55320.73800.48680.028*
C70.2220 (3)0.5461 (3)0.59057 (10)0.0306 (7)
H7A0.21390.60510.61920.046*
H7B0.22510.45470.60210.046*
H7C0.13620.55850.56880.046*
C80.6234 (3)0.4226 (3)0.51357 (10)0.0245 (7)
H8A0.61820.43240.54980.037*
H8B0.72690.42780.50280.037*
H8C0.58210.33710.50400.037*
C90.2980 (3)0.4027 (3)0.49735 (9)0.0256 (6)
H9A0.35390.33140.51390.031*
H9B0.19610.40290.51080.031*
C100.2930 (3)0.3772 (3)0.44191 (9)0.0202 (6)
H10A0.26400.28320.43690.024*
C110.4358 (3)0.4013 (3)0.41255 (9)0.0180 (6)
C120.5213 (3)0.5248 (3)0.43077 (8)0.0184 (5)
H12A0.45720.60090.42120.022*
C130.1512 (3)0.5072 (3)0.37875 (10)0.0241 (6)
C140.2882 (3)0.5266 (3)0.34730 (9)0.0204 (6)
H14A0.33580.61310.35490.024*
C150.3934 (3)0.4154 (3)0.35733 (9)0.0187 (6)
H15A0.34080.33260.34780.022*
C160.5477 (3)0.4080 (3)0.33405 (9)0.0208 (6)
C170.6442 (3)0.5287 (3)0.34586 (9)0.0221 (6)
H17A0.74280.51850.32940.026*
C180.6665 (3)0.5457 (3)0.40194 (9)0.0215 (6)
H18A0.69840.63870.40770.026*
C190.5370 (3)0.2805 (3)0.40671 (9)0.0224 (6)
H19A0.61210.27820.43350.027*
H19B0.47830.19830.40800.027*
C200.1948 (3)0.6338 (3)0.27507 (10)0.0228 (6)
C210.1545 (3)0.6143 (3)0.22154 (10)0.0286 (7)
H21A0.13140.52030.21580.034*
H21B0.24030.63770.20040.034*
C220.0221 (3)0.6972 (3)0.20635 (10)0.0318 (7)
H22A0.04420.79130.21430.038*
C23−0.1148 (4)0.6563 (5)0.23499 (13)0.0614 (12)
H23A−0.09800.66960.27060.092*
H23B−0.13560.56320.22860.092*
H23C−0.19920.70970.22420.092*
C24−0.0041 (4)0.6853 (3)0.15038 (10)0.0406 (8)
H24A0.08460.71420.13250.061*
H24B−0.08820.74070.14080.061*
H24C−0.02550.59350.14200.061*
C250.5346 (3)0.3717 (3)0.27880 (9)0.0219 (6)
C260.5432 (4)0.4542 (3)0.19654 (9)0.0334 (7)
H26A0.54250.54020.18000.050*
H26B0.44740.41090.19160.050*
H26C0.62200.39960.18230.050*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0367 (13)0.0451 (13)0.0268 (11)−0.0157 (11)−0.0012 (10)−0.0098 (10)
O20.0447 (13)0.0469 (13)0.0201 (10)−0.0177 (12)0.0047 (10)−0.0092 (10)
O30.0206 (10)0.0399 (12)0.0177 (10)0.0006 (9)0.0003 (8)0.0049 (9)
O40.0181 (10)0.0443 (12)0.0299 (11)0.0001 (10)−0.0005 (9)0.0046 (10)
O50.0320 (11)0.0245 (10)0.0160 (9)−0.0028 (9)−0.0003 (8)0.0018 (8)
O60.0193 (10)0.0444 (13)0.0239 (10)0.0039 (10)0.0007 (8)0.0059 (10)
O70.0284 (11)0.0261 (11)0.0198 (10)0.0060 (9)0.0016 (8)0.0028 (8)
O80.0254 (10)0.0268 (10)0.0150 (9)0.0032 (9)−0.0046 (8)−0.0005 (8)
O90.0328 (12)0.0266 (11)0.0258 (10)0.0023 (10)−0.0041 (9)−0.0026 (9)
O100.0412 (13)0.0299 (11)0.0214 (10)−0.0062 (10)0.0040 (9)−0.0042 (8)
O110.0379 (12)0.0291 (10)0.0152 (9)−0.0013 (10)−0.0013 (8)0.0012 (8)
C10.0361 (18)0.0262 (16)0.0224 (15)−0.0050 (14)0.0001 (13)−0.0037 (12)
C20.0341 (16)0.0287 (15)0.0177 (13)−0.0039 (14)0.0043 (13)−0.0059 (12)
C30.0287 (16)0.0230 (14)0.0197 (14)−0.0008 (12)0.0042 (12)−0.0010 (11)
C40.0224 (14)0.0231 (14)0.0171 (13)−0.0025 (13)0.0026 (11)0.0013 (12)
C50.0216 (13)0.0216 (13)0.0168 (12)−0.0007 (13)0.0000 (11)0.0028 (11)
C60.0269 (16)0.0263 (15)0.0179 (13)−0.0046 (13)0.0005 (12)−0.0038 (12)
C70.0326 (16)0.0345 (17)0.0247 (15)−0.0085 (15)0.0045 (13)−0.0031 (13)
C80.0280 (16)0.0300 (16)0.0155 (13)0.0053 (13)−0.0012 (12)−0.0007 (12)
C90.0289 (15)0.0300 (16)0.0178 (14)−0.0055 (14)0.0016 (12)0.0006 (12)
C100.0196 (14)0.0233 (15)0.0176 (13)−0.0001 (12)0.0003 (11)0.0008 (11)
C110.0153 (13)0.0200 (13)0.0187 (13)−0.0029 (11)0.0003 (11)−0.0014 (11)
C120.0178 (13)0.0207 (13)0.0166 (12)−0.0013 (12)−0.0024 (11)0.0011 (11)
C130.0219 (14)0.0268 (15)0.0237 (14)−0.0006 (13)0.0022 (11)−0.0010 (12)
C140.0179 (13)0.0270 (15)0.0163 (13)0.0000 (13)−0.0009 (10)0.0006 (12)
C150.0182 (13)0.0208 (14)0.0169 (13)−0.0026 (12)0.0016 (11)−0.0009 (11)
C160.0219 (14)0.0231 (14)0.0173 (13)0.0035 (12)−0.0002 (11)0.0031 (11)
C170.0225 (14)0.0243 (14)0.0193 (14)−0.0033 (13)0.0000 (11)−0.0005 (12)
C180.0210 (14)0.0285 (15)0.0151 (13)−0.0016 (13)−0.0008 (11)0.0019 (12)
C190.0266 (15)0.0239 (14)0.0167 (13)0.0018 (13)−0.0010 (12)0.0033 (11)
C200.0179 (14)0.0260 (15)0.0243 (14)0.0021 (12)0.0027 (12)0.0045 (12)
C210.0298 (16)0.0356 (17)0.0204 (14)0.0058 (15)−0.0047 (12)−0.0011 (13)
C220.0305 (16)0.0397 (17)0.0252 (15)0.0077 (15)−0.0054 (13)0.0029 (13)
C230.030 (2)0.111 (4)0.043 (2)0.005 (2)−0.0012 (16)0.010 (2)
C240.046 (2)0.046 (2)0.0298 (16)0.0170 (17)−0.0123 (15)0.0003 (15)
C250.0223 (14)0.0244 (14)0.0191 (13)0.0011 (13)0.0032 (12)0.0013 (11)
C260.0490 (19)0.0343 (17)0.0169 (14)0.0012 (17)−0.0033 (14)0.0016 (12)

Geometric parameters (Å, °)

O1—C11.231 (3)C9—H9A0.9900
O2—C21.364 (3)C9—H9B0.9900
O2—H2A0.8401C10—C111.532 (3)
O3—C131.346 (3)C10—H10A1.0000
O3—C101.475 (3)C11—C191.539 (4)
O4—C131.215 (3)C11—C151.541 (3)
O5—C171.424 (3)C11—C121.554 (3)
O5—H5A0.8401C12—C181.539 (3)
O6—C181.423 (3)C12—H12A1.0000
O6—H6A0.8400C13—C141.512 (4)
O7—C161.438 (3)C14—C151.502 (4)
O7—C191.446 (3)C14—H14A1.0000
O8—C201.371 (3)C15—C161.530 (4)
O8—C141.440 (3)C15—H15A1.0000
O9—C201.203 (3)C16—C251.536 (3)
O10—C251.210 (3)C16—C171.539 (4)
O11—C251.325 (3)C17—C181.532 (3)
O11—C261.460 (3)C17—H17A1.0000
C1—C21.463 (4)C18—H18A1.0000
C1—C61.503 (3)C19—H19A0.9900
C2—C31.347 (4)C19—H19B0.9900
C3—C71.494 (4)C20—C211.499 (4)
C3—C41.517 (3)C21—C221.519 (4)
C4—C91.539 (4)C21—H21A0.9900
C4—C51.553 (4)C21—H21B0.9900
C4—H4A1.0000C22—C231.515 (4)
C5—C61.539 (4)C22—C241.529 (4)
C5—C81.540 (4)C22—H22A1.0000
C5—C121.564 (3)C23—H23A0.9800
C6—H6B0.9900C23—H23B0.9800
C6—H6C0.9900C23—H23C0.9800
C7—H7A0.9800C24—H24A0.9800
C7—H7B0.9800C24—H24B0.9800
C7—H7C0.9800C24—H24C0.9800
C8—H8A0.9800C26—H26A0.9800
C8—H8B0.9800C26—H26B0.9800
C8—H8C0.9800C26—H26C0.9800
C9—C101.515 (3)
C2—O2—H2A109.5O8—C14—C15107.4 (2)
C13—O3—C10125.2 (2)O8—C14—C13108.9 (2)
C17—O5—H5A109.5C15—C14—C13108.6 (2)
C18—O6—H6A109.5O8—C14—H14A110.6
C16—O7—C19109.04 (19)C15—C14—H14A110.6
C20—O8—C14115.9 (2)C13—C14—H14A110.6
C25—O11—C26116.4 (2)C14—C15—C16122.7 (2)
O1—C1—C2120.6 (2)C14—C15—C11113.6 (2)
O1—C1—C6121.8 (3)C16—C15—C1199.44 (19)
C2—C1—C6117.5 (2)C14—C15—H15A106.7
C3—C2—O2120.7 (3)C16—C15—H15A106.7
C3—C2—C1122.2 (2)C11—C15—H15A106.7
O2—C2—C1117.1 (2)O7—C16—C15101.1 (2)
C2—C3—C7119.9 (2)O7—C16—C25106.5 (2)
C2—C3—C4120.9 (2)C15—C16—C25109.8 (2)
C7—C3—C4119.2 (2)O7—C16—C17109.4 (2)
C3—C4—C9113.3 (2)C15—C16—C17113.1 (2)
C3—C4—C5113.6 (2)C25—C16—C17115.8 (2)
C9—C4—C5109.2 (2)O5—C17—C18105.3 (2)
C3—C4—H4A106.7O5—C17—C16112.0 (2)
C9—C4—H4A106.7C18—C17—C16111.6 (2)
C5—C4—H4A106.7O5—C17—H17A109.3
C6—C5—C8107.5 (2)C18—C17—H17A109.3
C6—C5—C4107.6 (2)C16—C17—H17A109.3
C8—C5—C4110.8 (2)O6—C18—C17112.5 (2)
C6—C5—C12109.2 (2)O6—C18—C12110.5 (2)
C8—C5—C12115.6 (2)C17—C18—C12111.6 (2)
C4—C5—C12105.9 (2)O6—C18—H18A107.3
C1—C6—C5110.6 (2)C17—C18—H18A107.3
C1—C6—H6B109.5C12—C18—H18A107.3
C5—C6—H6B109.5O7—C19—C11105.9 (2)
C1—C6—H6C109.5O7—C19—H19A110.5
C5—C6—H6C109.5C11—C19—H19A110.5
H6B—C6—H6C108.1O7—C19—H19B110.5
C3—C7—H7A109.5C11—C19—H19B110.5
C3—C7—H7B109.5H19A—C19—H19B108.7
H7A—C7—H7B109.5O9—C20—O8122.8 (2)
C3—C7—H7C109.5O9—C20—C21126.1 (3)
H7A—C7—H7C109.5O8—C20—C21111.1 (2)
H7B—C7—H7C109.5C20—C21—C22112.1 (2)
C5—C8—H8A109.5C20—C21—H21A109.2
C5—C8—H8B109.5C22—C21—H21A109.2
H8A—C8—H8B109.5C20—C21—H21B109.2
C5—C8—H8C109.5C22—C21—H21B109.2
H8A—C8—H8C109.5H21A—C21—H21B107.9
H8B—C8—H8C109.5C23—C22—C21110.7 (3)
C10—C9—C4110.8 (2)C23—C22—C24110.7 (3)
C10—C9—H9A109.5C21—C22—C24110.1 (2)
C4—C9—H9A109.5C23—C22—H22A108.5
C10—C9—H9B109.5C21—C22—H22A108.5
C4—C9—H9B109.5C24—C22—H22A108.5
H9A—C9—H9B108.1C22—C23—H23A109.5
O3—C10—C9103.1 (2)C22—C23—H23B109.5
O3—C10—C11113.1 (2)H23A—C23—H23B109.5
C9—C10—C11117.1 (2)C22—C23—H23C109.5
O3—C10—H10A107.7H23A—C23—H23C109.5
C9—C10—H10A107.7H23B—C23—H23C109.5
C11—C10—H10A107.7C22—C24—H24A109.5
C10—C11—C19115.2 (2)C22—C24—H24B109.5
C10—C11—C15107.7 (2)H24A—C24—H24B109.5
C19—C11—C1597.09 (19)C22—C24—H24C109.5
C10—C11—C12112.6 (2)H24A—C24—H24C109.5
C19—C11—C12112.4 (2)H24B—C24—H24C109.5
C15—C11—C12110.6 (2)O10—C25—O11125.5 (2)
C18—C12—C11112.1 (2)O10—C25—C16122.8 (2)
C18—C12—C5115.6 (2)O11—C25—C16111.7 (2)
C11—C12—C5113.3 (2)O11—C26—H26A109.5
C18—C12—H12A104.8O11—C26—H26B109.5
C11—C12—H12A104.8H26A—C26—H26B109.5
C5—C12—H12A104.8O11—C26—H26C109.5
O4—C13—O3118.6 (2)H26A—C26—H26C109.5
O4—C13—C14123.4 (2)H26B—C26—H26C109.5
O3—C13—C14118.0 (2)
O1—C1—C2—C3−175.1 (3)O4—C13—C14—C15−144.5 (3)
C6—C1—C2—C36.7 (4)O3—C13—C14—C1538.1 (3)
O1—C1—C2—O24.4 (4)O8—C14—C15—C1666.1 (3)
C6—C1—C2—O2−173.8 (2)C13—C14—C15—C16−176.3 (2)
O2—C2—C3—C75.4 (4)O8—C14—C15—C11−174.3 (2)
C1—C2—C3—C7−175.1 (3)C13—C14—C15—C11−56.7 (3)
O2—C2—C3—C4−175.6 (3)C10—C11—C15—C1459.6 (3)
C1—C2—C3—C43.9 (4)C19—C11—C15—C14178.9 (2)
C2—C3—C4—C9144.4 (3)C12—C11—C15—C14−63.8 (3)
C7—C3—C4—C9−36.6 (4)C10—C11—C15—C16−168.3 (2)
C2—C3—C4—C518.9 (4)C19—C11—C15—C16−49.0 (2)
C7—C3—C4—C5−162.1 (2)C12—C11—C15—C1668.3 (3)
C3—C4—C5—C6−49.3 (3)C19—O7—C16—C15−27.3 (2)
C9—C4—C5—C6−176.9 (2)C19—O7—C16—C25−141.9 (2)
C3—C4—C5—C867.9 (3)C19—O7—C16—C1792.2 (2)
C9—C4—C5—C8−59.7 (3)C14—C15—C16—O7174.3 (2)
C3—C4—C5—C12−166.0 (2)C11—C15—C16—O748.2 (2)
C9—C4—C5—C1266.4 (3)C14—C15—C16—C25−73.5 (3)
O1—C1—C6—C5142.6 (3)C11—C15—C16—C25160.4 (2)
C2—C1—C6—C5−39.3 (4)C14—C15—C16—C1757.4 (3)
C8—C5—C6—C1−60.5 (3)C11—C15—C16—C17−68.7 (3)
C4—C5—C6—C158.9 (3)O7—C16—C17—O5−170.0 (2)
C12—C5—C6—C1173.4 (2)C15—C16—C17—O5−58.2 (3)
C3—C4—C9—C10171.4 (2)C25—C16—C17—O569.7 (3)
C5—C4—C9—C10−60.9 (3)O7—C16—C17—C18−52.3 (3)
C13—O3—C10—C9155.6 (2)C15—C16—C17—C1859.5 (3)
C13—O3—C10—C1128.2 (3)C25—C16—C17—C18−172.6 (2)
C4—C9—C10—O3−78.0 (3)O5—C17—C18—O6−157.1 (2)
C4—C9—C10—C1146.9 (3)C16—C17—C18—O681.1 (3)
O3—C10—C11—C19−148.5 (2)O5—C17—C18—C1278.1 (3)
C9—C10—C11—C1991.8 (3)C16—C17—C18—C12−43.7 (3)
O3—C10—C11—C15−41.5 (3)C11—C12—C18—O6−80.7 (3)
C9—C10—C11—C15−161.1 (2)C5—C12—C18—O651.2 (3)
O3—C10—C11—C1280.7 (3)C11—C12—C18—C1745.2 (3)
C9—C10—C11—C12−38.9 (3)C5—C12—C18—C17177.1 (2)
C10—C11—C12—C18178.5 (2)C16—O7—C19—C11−4.5 (3)
C19—C11—C12—C1846.3 (3)C10—C11—C19—O7147.0 (2)
C15—C11—C12—C18−61.0 (3)C15—C11—C19—O733.7 (2)
C10—C11—C12—C545.4 (3)C12—C11—C19—O7−82.2 (2)
C19—C11—C12—C5−86.8 (3)C14—O8—C20—O91.7 (4)
C15—C11—C12—C5165.9 (2)C14—O8—C20—C21−179.4 (2)
C6—C5—C12—C1853.9 (3)O9—C20—C21—C22−35.3 (4)
C8—C5—C12—C18−67.3 (3)O8—C20—C21—C22145.8 (2)
C4—C5—C12—C18169.6 (2)C20—C21—C22—C23−63.5 (4)
C6—C5—C12—C11−174.7 (2)C20—C21—C22—C24173.9 (3)
C8—C5—C12—C1164.1 (3)C26—O11—C25—O105.2 (4)
C4—C5—C12—C11−59.1 (3)C26—O11—C25—C16−172.5 (2)
C10—O3—C13—O4156.4 (3)O7—C16—C25—O1040.6 (4)
C10—O3—C13—C14−26.1 (4)C15—C16—C25—O10−68.0 (3)
C20—O8—C14—C15−158.5 (2)C17—C16—C25—O10162.5 (3)
C20—O8—C14—C1384.2 (3)O7—C16—C25—O11−141.6 (2)
O4—C13—C14—O8−27.9 (4)C15—C16—C25—O11109.8 (3)
O3—C13—C14—O8154.7 (2)C17—C16—C25—O11−19.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2A···O9i0.842.112.870 (3)150
O2—H2A···O10.842.282.718 (3)113
O5—H5A···O10ii0.842.172.874 (2)142
O5—H5A···O110.842.192.797 (2)129
O6—H6A···O4iii0.841.972.799 (3)171

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) −x+1, y+1/2, −z+1/2; (iii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5331).

References

  • Anderson, M. M., O’Neill, M. J., Phillipson, J. D. & Warhurst, D. C. (1991). Planta Med 57, 62–64. [PubMed]
  • Bawm, S., Matsuura, H., Elkhateeb, A., Nabeta, K., Subeki, Nonaka, N., Oku, Y., Katakura, K. (2008). Vet Parasitol 158, 288–294. [PubMed]
  • Elkhateeb, A., Yamasaki, M., Maede, Y., Katakura, K., Nabeta, K. & Matsuura, H. (2008). Nat Prod Commun 3, 145–148.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Klocke, J. A., Arisawa, M., Handa, S. S., Kinghorn, A. D., Cordel, I. G. A. & Farnsworth, N. R. (1985). Chem Org Naturst 47, 222–264.
  • Leskinen, V., Polonsky, J. & Bhatnagar, S. (1984). J Chem Ecol 10, 1497–1507. [PubMed]
  • Nakao, R., Mizukami, C., Kawamura, Y., Subeki, Bawm, S., Yamasaki, M., Maede, Y., Matsuura, H., Nabeta, K., Nonaka, N., Oku, Y., Katakura, K. (2009). J Vet Med Sci 71, 33–41. [PubMed]
  • Odjo, A., Piart, J., Polonsky, J. & Roth, M. (1981). C. R. Acad Sci 293, 241-244.
  • O’Neill, M. J., Bray, D. H., Boardman, P., Chan, K. L., Phillipson, J. D., Warhurst, D. C. & Peters, W. (1987). J Nat Prod 50, 41-48. [PubMed]
  • Pan, L., Chin, Y. W., Chai, H. B., Ninh, T. N., Soejarto, D. D. & Kinghorn, A. D. (2009). Bioorg. Med. Chem 17, 2219–2224. [PMC free article] [PubMed]
  • Pavanand, K., Nutakul, W., Dechatiwongse, T., Yoshihira, K., Yongvanitchit, K., Scovill, J. P., Flippen-Anderson, J. L., Gilardi, R. & George, C. (1986). Planta Med 52, 108-111. [PubMed]
  • Rigaku (2001). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Subeki, Matsuura, H., Takahashi, K., Nabeta, K., Yamasaki, M., Maede, Y., Katakura, K. (2007). J Nat Prod 70, 1654–1657. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography