3β-Hydroxy­friedelan-17β-carboxylic acid

Hai-Yan Chen; Cui-Wu Lin; Guang-Ying Chen; Guang-Chuan Ou

doi:10.1107/S1600536808010295

. 2008 Apr 23;64(Pt 5):o890. doi: 10.1107/S1600536808010295

3β-Hydroxyfriedelan-17β-carboxylic acid

Hai-Yan Chen ^a, Cui-Wu Lin ^a,^*, Guang-Ying Chen ^b, Guang-Chuan Ou ^c

PMCID: PMC2961169 PMID: 21202373

Abstract

The title compound, C₃₀H₅₀O₃, which was isolated from a marine endophytic fungus, is a new friedelan derivative. The molecule contains five six-membered rings, which exhibit boat (ring A), distorted boat (ring B) and chair (rings C–E) conformations. The crystal structure is stabilized by intermolecular O—H⋯O hydrogen bonds, which link neighbouring molecules into 12-membered rings.

Related literature

For general background, see: Chen et al. (2003 ▶, 2005 ▶, 2006a ▶,b ▶); Lin et al. (2001a ▶,b ▶, 2002 ▶). For related structures, see: Dhaneshwar et al. (1987 ▶); Fun et al. (2007 ▶); Mo (1977 ▶); Mo et al. (1989 ▶); Sun et al. (2004 ▶).

Experimental

Crystal data

C₃₀H₅₀O₃
M _r = 458.70
Orthorhombic,
a = 13.238 (3) Å
b = 24.141 (5) Å
c = 8.7349 (17) Å
V = 2791.5 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 153 (2) K
0.51 × 0.48 × 0.46 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
18448 measured reflections
3466 independent reflections
3010 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.112
S = 1.04
3466 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010295/xu2405sup1.cif

e-64-0o890-sup1.cif^{(28.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010295/xu2405Isup2.hkl

e-64-0o890-Isup2.hkl^{(169.6KB, 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
O35—H35⋯O41ⁱ	0.84	1.83	2.644 (2)	163
O41—H41⋯O34ⁱⁱ	0.84	1.89	2.721 (2)	168

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

Acknowledgments

The project was supported by Guangxi Science Foundation (Guikezi0728257, Guikeji0144002) and the National Natural Science Foundation of China (20562004). The X-ray data were collected at the Instrumentation Analysis and Research Center of Sun Yat-sen (Zhongshan) University; the authors thank the staff for all their help and advice. We acknowledge Dr S. Parkin at the University of Kentucky (Lexington) and Dr Z. Ma at the University of Guangxi (Nanning) for their advice.

supplementary crystallographic information

Comment

In the course of our ongoing research on the bioactive secondary metabolites from marine mangrove fungi (Chen et al., 2003, 2005, 2006a, 2006b; Lin et al., 2001a,b, 2002), the title compound was recently isolated from an unidentified species mangrove endophytic fungus No. H2K. It is a new friedelan analogue (Dhaneshwar et al., 1987; Fun et al., 2007; Mo, 1977; Mo et al., 1989; Sun et al., 2004). We report here the structure of the title compound. Further studies on properties are in progress.

The molecular structure is shown in Fig. 1. The molecule contains five six-membered rins, they exhibit boat (ring A), distorted boat (ring B) and chair conformations (rings C–E ), respectively. The crystal structure is stabilized by intermolecular O—H···O hydrogen bonds, which link neighbouring molecules into 12-membered rings (Table 1 and Fig. 2).

Experimental

Starter cultures were maintained on cornmeal seawater agar. Plugs of agar supporting mycelial growth were cut and transferred aseptically to a 250 ml Erlenmeyer flask containing 100 ml of liquid medium GYP (glucose 5 g/l, yeast extract 0.5 g/l, peptone 1 g/l, beef extract 0.5 g/l, NaCl 3 g/l). The flask was incubated at 30°C on a rotary shaker for 5 d, and the mycelium was aseptically transferred to a 500 ml Erlenmeyer flask containing culture liquid (200 ml). The flask was then incubated at 30°C for 4 weeks. The cultures (80 l) were filtered through cheesecloth. The filtrate was concentrated to 5 l in vacuo below 50°C and extracted three times by shaking with an equal volume of ethyl acetate. The combined organic extracts were applied to a silica gel column, eluting with a gradient of petroleum ether to ethyl acetate to offer title compound (30 mg). The single crystals of the title compound were obtained by recrystallizing from an ethyl acetate/petroleum ether solution (V/V 1:1).