Bruceine A

Xue-Huan Feng; Yan-Ning Zhang; Wei-Zhi He; Lan Zhang; Hong-Yun Jiang

doi:10.1107/S1600536810007646

. 2010 Mar 17;66(Pt 4):o854–o855. doi: 10.1107/S1600536810007646

Bruceine A

Xue-Huan Feng ^a, Yan-Ning Zhang ^a, Wei-Zhi He ^a, Lan Zhang ^a, Hong-Yun Jiang ^a,^*

PMCID: PMC2983995 PMID: 21580678

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 ▶); Bawm et al. (2008 ▶); Elkhateeb et al. (2008 ▶); Klocke et al. (1985 ▶); Leskinen et al. (1984 ▶); Nakao et al. (2009 ▶); O’Neill et al. (1987 ▶); Odjo et al. (1981 ▶); Pan et al. (2009 ▶); Pavanand et al. (1986 ▶); Subeki et al. (2007 ▶).

Experimental

Crystal data

C₂₆H₃₄O₁₁
M _r = 522.53
Orthorhombic,
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 ▶) 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
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 1887 Friedel pairs
Flack parameter: −0.3 (2)

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

Supplementary Material

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

e-66-0o854-sup1.cif^{(28KB, cif)}

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

e-66-0o854-Isup2.hkl^{(219.4KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O9ⁱ	0.84	2.11	2.870 (3)	150
O2—H2A⋯O1	0.84	2.28	2.718 (3)	113
O5—H5A⋯O10ⁱⁱ	0.84	2.17	2.874 (2)	142
O5—H5A⋯O11	0.84	2.19	2.797 (2)	129
O6—H6A⋯O4ⁱⁱⁱ	0.84	1.97	2.799 (3)	171

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

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.