3β-Hydro­xy­olean-12-en-27-oic acid methanol solvate: a cytotoxic and apoptosis-inducing triterpenoid from the rhizome of Astilbe chinensis

Sun, H.-X.; Ye, Y.-P.; Wang, K.-W.; Pan, Y.-J.

doi:10.1107/S1600536803012571

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3β-Hydroxyolean-12-en-27-oic acid methanol solvate: a cytotoxic and apoptosis-inducing triterpenoid from the rhizome of Astilbe chinensis

H.-X. Sun, Y.-P. Ye, K.-W. Wang and Y.-J. Pan

The title compound, C₃₀H₄₈O₃·CH₄O, is a cytotoxic and apoptosis-inducing triterpenoid which was isolated from the rhizome of Astilbe chinensis. The molecule is composed of five six-membered rings. The cyclohexene ring adopts a slightly distorted half-chair conformation and the cyclohexane rings adopt chair conformations. The hydroxy and carboxy groups both serve simultaneously as hydrogen-bond donors and acceptors, forming molecular chains.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803012571/ci6226sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803012571/ci6226Isup2.hkl Contains datablock I

CCDC reference: 217468

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.007 Å
R factor = 0.057
wR factor = 0.158
Data-to-parameter ratio = 10.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.00
         From the CIF: _reflns_number_total               3203
         Count of symmetry unique reflns         3209
         Completeness (_total/calc)             99.81%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

Comment top

Astilbe chinensis (Haxim.) Franch. et Savat. (Saxiffagaceae) is a perennial herbaceous plant growing at an altitude of 390–3600 m in China, Russia, Japan and Korea. Its rhizome, known as 'Luo Xinfu' (Chinese name), has been used for headache, arthralgia, chronic bronchitis and stomachalgia, in traditional Chinese medicine (Pan, 1985, 1995). Pharmacological experiments have indicated that the extracts from A. chinensis had antineoplastic and immunopotent activities (Chen et al., 1996). Previously, we isolated β-sitosterol palmitate, daucosterol, β-sitosterol and bergenin from the rhizome of A. chinensis (Sun et al., 2002). To investigate the bioactive natural products from A. chinensis, chemical studies on the rhizome of A. chinensis were undertaken by screening using antineoplastic tests in vitro and we have obtained cytotoxic and apoptotic-inducing triterpenoid 3β-hydroxyolean-12-en-27-oic acid, (I), from its petroleum ether extract. It exhibits significant cytotoxic activity against human ovarian carcinoma cell line (HO-8910), human cervical squamous carcinoma cell line (HeLa) and human leukemia cell (HL60) in vitro, its 50% inhibitory concentration (IC50) values were 8.0 (9), 3.94 (13) and 3.67 (19) µg ml⁻¹, respectively. Moreover, it induces apoptotic cell death of the HO-8910 in a dose-dependent manner, ranging from 2.5 µg mL⁻¹ to 40.0 µg mL⁻¹. The structure of the title compound, (I), was elucidated by spectroscopic analysis including two-dimensional NMR spectroscopy and confirmed by single-crystal X-diffraction analysis.

The structure of (I) with the atom-numbering scheme is shown in Fig. 1. The molecule is composed of five six-membered rings, viz. A (C1—C5/C10), B (C5—C10), C (C8/C9/C11—C14), D (C13—C18) and E (C17—C22). Rings A, B, D and E adopt chair conformations whereas ring C adopts a slightly distorted half-chair conformation owing to the C12═C13 double bond. All rings are trans fused except for D/E junction, which is cis fused. The orientation of the carboxy group is axial and that for hydroxy group is equatorial.

The hydroxy and carboxy groups both serve as simultaneous hydrogen-bond donors and acceptors (Table 2). In the asymmetric unit, the two molecules are linked by O2—H2···O4 hydrogen bonds. In the solid state, the screw-related molecules are linked by O1—H1···O3ⁱ hydrogen bonds (Table 2), to form molecular chains along the a axis. The chain formation is further stabilized by the methanol solvate through O4—H4O···O1ⁱ hydrogen bonds. The crystal structure is further stabilsed by C—H···O interactions.

Experimental top

The rhizomes of Astilbe Chinensis were collected in Anji county, Zhejiang province, China in August 2001. The plants were identified as A. chinensis (Haxim.) Franch. et Savat. by Professor Xiang-Ji Xue, College of Pharmaceutical Science, Zhejiang University. A voucher specimen (No. 200120) was deposited in Laboratory of Nature and Biochemistry, Zhejiang University. The rhizomes of Astilbe Chinensis were dried at 313 K in the dark, in a ventilated hood, and ground. The material (5.0 kg) was extracted three times with CH₃OH (each 25 l) at room temperature. The CH₃OH extract (366 g) was partitioned between petroleum ether (20 l) and water (2 l). The petroleum ether solution was concentrated in vacuum to give 41.2 g of a gelatinous material. A part of the extract (40.0 g) was absorbed onto silica gel (60 g) and chromatographied on a silica gel (600 g) column eluted with petroleum ether-EtoAc (50:1, 30:1, 15:1, 5:1, 3:1, 2:1) gradients. The eluted fractions were evaluated by TLC and combined to give fractions 1 to 19, respectively. Fraction 12 was recrystallized with EtOAc–CH₃OH (1:1) to afford 2.5 g of the pure title compound, (I). m.p.: 513.5–515.5 K. ¹³C NMR (125 MHz, C₅ND₅, p.p.m): 179.4 (C27), 138.2 (C13), 126.2 (C12), 79.4 (C3), 55.8 (C14), 55.2 (C5), 49.0 (C18), 47.2 (C9), 43.9 (C19), 39.7 (C8), 7 (C4), 38.6 (C1), 37.1 (C10), 36.5 (C21), 36.3 (C7), 34.3 (C22), 33.5 (C29), 38 32.8 (C17), 31.1 (C20), 28.2 (C28), 28.1 (C23), 27.5(C2),26.9 (C16), 23.6 (C30), 22.8 (C11), 22.2 (C15), 18.2 (C6), 18.0 (C26), 16.4 (C25), 16.0 (C24). Crystals suitable for X-ray structure analysis were obtained by slow evaporation from methanol at room temperature.

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Siemens, 1991); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. A view of (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 35% probability level. H atoms have been omitted for clarity.

(4aR,6bR,12aR)-10-Hydroxy-2,2,4a,6 b,9,9,12a-heptamethyl- 2,3,4,4a,5,6,6 b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro- 1H-picene-6a-carboxylic acid methanol solvate top

Crystal data top

C₃₀H₄₈O₃·CH₄O	F(000) = 1080
M_r = 488.73	D_x = 1.137 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 38 reflections
a = 7.538 (2) Å	θ = 2.9–13.8°
b = 13.710 (3) Å	µ = 0.07 mm⁻¹
c = 27.629 (8) Å	T = 296 K
V = 2855.3 (13) Å³	Prism, colorless
Z = 4	0.58 × 0.40 × 0.24 mm

Data collection top

Siemens P4 diffractometer	R_int = 0.021
Radiation source: normal-focus sealed tube	θ_max = 26.0°, θ_min = 1.7°
Graphite monochromator	h = 0→9
ω scans	k = 0→16
3492 measured reflections	l = −1→34
3203 independent reflections	3 standard reflections every 97 reflections
1876 reflections with I > 2σ(I)	intensity decay: 1.5%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.158	w = 1/[σ²(F_o²) + (0.0951P)²] where P = (F_o² + 2F_c²)/3
S = 0.89	(Δ/σ)_max < 0.001
3203 reflections	Δρ_max = 0.21 e Å⁻³
316 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0116 (17)

Crystal data top

C₃₀H₄₈O₃·CH₄O	V = 2855.3 (13) Å³
M_r = 488.73	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.538 (2) Å	µ = 0.07 mm⁻¹
b = 13.710 (3) Å	T = 296 K
c = 27.629 (8) Å	0.58 × 0.40 × 0.24 mm

Data collection top

Siemens P4 diffractometer	R_int = 0.021
3492 measured reflections	3 standard reflections every 97 reflections
3203 independent reflections	intensity decay: 1.5%
1876 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 0.89	Δρ_max = 0.21 e Å⁻³
3203 reflections	Δρ_min = −0.19 e Å⁻³
316 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.4762 (4)	−0.0208 (3)	0.51890 (12)	0.0620 (10)
H1	0.3817	−0.0143	0.5333	0.093*
O2	0.4050 (4)	0.5275 (2)	0.37966 (11)	0.0560 (9)
H2	0.3778	0.5625	0.4026	0.084*
O3	0.6369 (4)	0.4965 (2)	0.42622 (10)	0.0484 (8)
C1	0.7680 (6)	0.1705 (3)	0.46233 (16)	0.0449 (12)
H1A	0.8964	0.1731	0.4603	0.054*
H1B	0.7287	0.2264	0.4810	0.054*
C2	0.7130 (6)	0.0764 (4)	0.48897 (18)	0.0491 (13)
H2A	0.7607	0.0204	0.4719	0.059*
H2B	0.7628	0.0768	0.5213	0.059*
C3	0.5152 (6)	0.0675 (4)	0.49213 (16)	0.0473 (12)
H3	0.4715	0.1227	0.5112	0.057*
C4	0.4211 (6)	0.0704 (3)	0.44268 (17)	0.0430 (11)
C5	0.4858 (5)	0.1643 (3)	0.41638 (15)	0.0356 (10)
H5	0.4515	0.2170	0.4384	0.043*
C6	0.3910 (6)	0.1891 (3)	0.36983 (16)	0.0445 (11)
H6A	0.2652	0.1764	0.3734	0.053*
H6B	0.4357	0.1483	0.3439	0.053*
C7	0.4200 (6)	0.2978 (3)	0.35689 (16)	0.0413 (11)
H7A	0.3531	0.3135	0.3279	0.050*
H7B	0.3757	0.3383	0.3830	0.050*
C8	0.6169 (5)	0.3207 (3)	0.34835 (14)	0.0341 (10)
C9	0.7282 (5)	0.2852 (3)	0.39223 (15)	0.0346 (10)
H9	0.6953	0.3281	0.4191	0.042*
C10	0.6899 (5)	0.1774 (3)	0.41076 (16)	0.0366 (11)
C11	0.9246 (6)	0.3043 (3)	0.38315 (17)	0.0454 (12)
H11A	0.9878	0.3004	0.4137	0.055*
H11B	0.9708	0.2536	0.3621	0.055*
C12	0.9599 (6)	0.4020 (3)	0.36042 (16)	0.0421 (11)
H12	1.0777	0.4221	0.3591	0.050*
C13	0.8396 (6)	0.4630 (3)	0.34187 (15)	0.0378 (10)
C14	0.6421 (5)	0.4355 (3)	0.34280 (15)	0.0371 (10)
C15	0.5490 (6)	0.4746 (4)	0.29624 (16)	0.0466 (12)
H15A	0.5726	0.4296	0.2699	0.056*
H15B	0.4218	0.4749	0.3017	0.056*
C16	0.6056 (7)	0.5765 (4)	0.28055 (18)	0.0549 (13)
H16A	0.5695	0.6232	0.3050	0.066*
H16B	0.5456	0.5932	0.2506	0.066*
C17	0.8069 (6)	0.5839 (4)	0.27293 (17)	0.0511 (13)
C18	0.8975 (6)	0.5597 (3)	0.32132 (15)	0.0422 (11)
H18	1.0243	0.5532	0.3142	0.051*
C19	0.8813 (7)	0.6423 (3)	0.35877 (16)	0.0507 (12)
H19A	0.7580	0.6480	0.3684	0.061*
H19B	0.9490	0.6246	0.3873	0.061*
C20	0.9454 (8)	0.7419 (4)	0.3410 (2)	0.0640 (15)
C21	0.8390 (8)	0.7660 (4)	0.2944 (2)	0.0740 (18)
H21A	0.7146	0.7734	0.3026	0.089*
H21B	0.8803	0.8276	0.2813	0.089*
C22	0.8581 (8)	0.6870 (4)	0.25607 (18)	0.0685 (16)
H22A	0.9804	0.6859	0.2451	0.082*
H22B	0.7848	0.7042	0.2285	0.082*
C23	0.4504 (7)	−0.0255 (4)	0.41420 (18)	0.0592 (14)
H23A	0.3728	−0.0751	0.4266	0.089*
H23B	0.5714	−0.0462	0.4178	0.089*
H23C	0.4250	−0.0148	0.3806	0.089*
C24	0.2222 (6)	0.0786 (4)	0.45259 (19)	0.0564 (14)
H24A	0.1871	0.0289	0.4751	0.085*
H24B	0.1579	0.0706	0.4229	0.085*
H24C	0.1965	0.1416	0.4660	0.085*
C25	0.7728 (6)	0.0986 (3)	0.37885 (18)	0.0518 (13)
H25A	0.8036	0.0432	0.3984	0.078*
H25B	0.8776	0.1240	0.3636	0.078*
H25C	0.6893	0.0791	0.3545	0.078*
C26	0.6791 (7)	0.2719 (4)	0.30065 (16)	0.0508 (12)
H26A	0.6879	0.2027	0.3053	0.076*
H26B	0.7930	0.2975	0.2917	0.076*
H26C	0.5949	0.2854	0.2755	0.076*
C27	0.5642 (6)	0.4899 (3)	0.38719 (16)	0.0394 (11)
C28	0.8725 (8)	0.5138 (4)	0.23351 (15)	0.0672 (16)
H28A	0.8102	0.5266	0.2039	0.101*
H28B	0.8510	0.4478	0.2434	0.101*
H28C	0.9974	0.5232	0.2285	0.101*
C29	1.1465 (7)	0.7437 (4)	0.3318 (2)	0.0716 (17)
H29A	1.2082	0.7308	0.3615	0.107*
H29B	1.1803	0.8067	0.3197	0.107*
H29C	1.1765	0.6947	0.3083	0.107*
C30	0.9068 (11)	0.8182 (4)	0.3801 (2)	0.103 (2)
H30A	0.9762	0.8041	0.4084	0.154*
H30B	0.7830	0.8165	0.3883	0.154*
H30C	0.9370	0.8819	0.3683	0.154*
O4	0.2549 (5)	0.6319 (3)	0.44767 (13)	0.0648 (10)
H4O	0.1650	0.6089	0.4599	0.097*
C31	0.3446 (14)	0.6856 (6)	0.4815 (3)	0.134 (3)
H31A	0.4700	0.6785	0.4765	0.201*
H31B	0.3144	0.6628	0.5133	0.201*
H31C	0.3124	0.7530	0.4785	0.201*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.042 (2)	0.070 (2)	0.074 (2)	−0.0003 (18)	0.0055 (18)	0.029 (2)
O2	0.0364 (18)	0.061 (2)	0.070 (2)	0.0182 (17)	0.0001 (17)	0.0005 (18)
O3	0.0497 (19)	0.052 (2)	0.0433 (17)	0.0130 (16)	0.0019 (16)	0.0015 (16)
C1	0.028 (2)	0.046 (3)	0.061 (3)	0.000 (2)	−0.007 (2)	0.011 (2)
C2	0.036 (3)	0.049 (3)	0.062 (3)	0.001 (2)	−0.008 (2)	0.015 (3)
C3	0.043 (3)	0.053 (3)	0.046 (3)	0.005 (2)	0.002 (2)	0.014 (3)
C4	0.032 (2)	0.038 (2)	0.059 (3)	0.000 (2)	0.003 (2)	0.004 (2)
C5	0.028 (2)	0.037 (2)	0.041 (2)	0.0009 (19)	−0.0053 (19)	0.001 (2)
C6	0.034 (2)	0.048 (3)	0.052 (3)	−0.003 (2)	−0.007 (2)	0.003 (2)
C7	0.032 (2)	0.044 (3)	0.048 (3)	0.003 (2)	−0.008 (2)	0.005 (2)
C8	0.029 (2)	0.034 (2)	0.039 (2)	0.0038 (19)	−0.0023 (19)	−0.0006 (19)
C9	0.029 (2)	0.030 (2)	0.046 (2)	0.0039 (19)	−0.004 (2)	0.0005 (19)
C10	0.028 (2)	0.029 (2)	0.053 (3)	0.0028 (19)	−0.001 (2)	0.000 (2)
C11	0.032 (2)	0.041 (3)	0.063 (3)	0.001 (2)	−0.005 (2)	0.011 (2)
C12	0.028 (2)	0.044 (3)	0.054 (3)	0.007 (2)	0.001 (2)	0.008 (2)
C13	0.031 (2)	0.048 (3)	0.035 (2)	0.003 (2)	0.001 (2)	0.001 (2)
C14	0.028 (2)	0.051 (3)	0.032 (2)	0.005 (2)	0.0012 (19)	0.005 (2)
C15	0.038 (3)	0.052 (3)	0.050 (3)	0.001 (2)	−0.010 (2)	0.009 (2)
C16	0.055 (3)	0.064 (3)	0.045 (3)	0.004 (3)	−0.013 (3)	0.016 (3)
C17	0.046 (3)	0.062 (3)	0.046 (3)	0.000 (3)	0.000 (2)	0.015 (3)
C18	0.034 (2)	0.048 (3)	0.045 (2)	0.007 (2)	0.000 (2)	0.005 (2)
C19	0.054 (3)	0.047 (3)	0.052 (3)	0.003 (3)	0.008 (3)	0.008 (2)
C20	0.077 (4)	0.047 (3)	0.068 (3)	−0.001 (3)	0.003 (3)	0.009 (3)
C21	0.068 (4)	0.052 (3)	0.102 (5)	0.000 (3)	−0.006 (4)	0.035 (3)
C22	0.076 (4)	0.067 (4)	0.062 (3)	0.002 (3)	−0.006 (3)	0.026 (3)
C23	0.053 (3)	0.044 (3)	0.081 (4)	−0.006 (3)	0.003 (3)	0.000 (3)
C24	0.036 (3)	0.065 (3)	0.068 (3)	−0.002 (3)	0.001 (3)	0.013 (3)
C25	0.041 (3)	0.043 (3)	0.072 (3)	0.010 (2)	0.011 (3)	0.000 (3)
C26	0.046 (3)	0.058 (3)	0.048 (3)	−0.001 (3)	0.003 (2)	−0.003 (2)
C27	0.036 (3)	0.038 (3)	0.044 (3)	0.004 (2)	−0.001 (2)	0.009 (2)
C28	0.083 (4)	0.078 (4)	0.040 (3)	−0.006 (4)	0.009 (3)	0.001 (3)
C29	0.066 (4)	0.072 (4)	0.077 (4)	−0.015 (3)	−0.008 (3)	0.019 (3)
C30	0.144 (7)	0.048 (3)	0.115 (5)	−0.002 (4)	0.025 (6)	−0.010 (4)
O4	0.059 (2)	0.061 (2)	0.075 (2)	0.008 (2)	0.017 (2)	0.009 (2)
C31	0.169 (9)	0.127 (7)	0.104 (5)	−0.023 (7)	−0.015 (6)	−0.023 (5)

Geometric parameters (Å, º) top

O1—C3	1.449 (5)	C16—C17	1.536 (7)
O1—H1	0.82	C16—H16A	0.97
O2—C27	1.323 (5)	C16—H16B	0.97
O2—H2	0.82	C17—C28	1.534 (7)
O3—C27	1.213 (5)	C17—C22	1.537 (7)
C1—C2	1.542 (6)	C17—C18	1.538 (6)
C1—C10	1.544 (6)	C18—C19	1.540 (6)
C1—H1A	0.97	C18—H18	0.98
C1—H1B	0.97	C19—C20	1.530 (7)
C2—C3	1.499 (6)	C19—H19A	0.97
C2—H2A	0.97	C19—H19B	0.97
C2—H2B	0.97	C20—C30	1.534 (8)
C3—C4	1.540 (6)	C20—C29	1.537 (8)
C3—H3	0.98	C20—C21	1.552 (7)
C4—C24	1.528 (6)	C21—C22	1.522 (8)
C4—C23	1.549 (6)	C21—H21A	0.97
C4—C5	1.556 (6)	C21—H21B	0.97
C5—C6	1.510 (6)	C22—H22A	0.97
C5—C10	1.556 (6)	C22—H22B	0.97
C5—H5	0.98	C23—H23A	0.96
C6—C7	1.548 (6)	C23—H23B	0.96
C6—H6A	0.97	C23—H23C	0.96
C6—H6B	0.97	C24—H24A	0.96
C7—C8	1.535 (6)	C24—H24B	0.96
C7—H7A	0.97	C24—H24C	0.96
C7—H7B	0.97	C25—H25A	0.96
C8—C26	1.550 (6)	C25—H25B	0.96
C8—C9	1.552 (5)	C25—H25C	0.96
C8—C14	1.593 (6)	C26—H26A	0.96
C9—C11	1.524 (6)	C26—H26B	0.96
C9—C10	1.591 (5)	C26—H26C	0.96
C9—H9	0.98	C28—H28A	0.96
C10—C25	1.528 (6)	C28—H28B	0.96
C11—C12	1.503 (6)	C28—H28C	0.96
C11—H11A	0.97	C29—H29A	0.96
C11—H11B	0.97	C29—H29B	0.96
C12—C13	1.336 (6)	C29—H29C	0.96
C12—H12	0.93	C30—H30A	0.96
C13—C18	1.506 (6)	C30—H30B	0.96
C13—C14	1.536 (6)	C30—H30C	0.96
C14—C27	1.551 (6)	O4—C31	1.369 (8)
C14—C15	1.561 (6)	O4—H4O	0.82
C15—C16	1.524 (7)	C31—H31A	0.96
C15—H15A	0.97	C31—H31B	0.96
C15—H15B	0.97	C31—H31C	0.96

C3—O1—H1	109.5	C17—C16—H16B	109.2
C27—O2—H2	109.5	H16A—C16—H16B	107.9
C2—C1—C10	112.9 (4)	C28—C17—C16	112.0 (5)
C2—C1—H1A	109.0	C28—C17—C22	106.2 (4)
C10—C1—H1A	109.0	C16—C17—C22	110.5 (4)
C2—C1—H1B	109.0	C28—C17—C18	109.8 (4)
C10—C1—H1B	109.0	C16—C17—C18	107.8 (4)
H1A—C1—H1B	107.8	C22—C17—C18	110.5 (4)
C3—C2—C1	111.3 (4)	C13—C18—C17	112.9 (4)
C3—C2—H2A	109.4	C13—C18—C19	111.8 (3)
C1—C2—H2A	109.4	C17—C18—C19	113.0 (4)
C3—C2—H2B	109.4	C13—C18—H18	106.2
C1—C2—H2B	109.4	C17—C18—H18	106.2
H2A—C2—H2B	108.0	C19—C18—H18	106.2
O1—C3—C2	107.5 (4)	C20—C19—C18	114.6 (4)
O1—C3—C4	112.4 (4)	C20—C19—H19A	108.6
C2—C3—C4	113.9 (4)	C18—C19—H19A	108.6
O1—C3—H3	107.6	C20—C19—H19B	108.6
C2—C3—H3	107.6	C18—C19—H19B	108.6
C4—C3—H3	107.6	H19A—C19—H19B	107.6
C24—C4—C3	107.2 (4)	C19—C20—C30	108.8 (4)
C24—C4—C23	107.1 (4)	C19—C20—C29	112.3 (5)
C3—C4—C23	111.3 (4)	C30—C20—C29	107.1 (5)
C24—C4—C5	109.3 (4)	C19—C20—C21	107.0 (5)
C3—C4—C5	106.9 (4)	C30—C20—C21	110.0 (5)
C23—C4—C5	114.9 (4)	C29—C20—C21	111.7 (5)
C6—C5—C4	115.8 (4)	C22—C21—C20	112.1 (4)
C6—C5—C10	110.9 (4)	C22—C21—H21A	109.2
C4—C5—C10	116.9 (3)	C20—C21—H21A	109.2
C6—C5—H5	103.7	C22—C21—H21B	109.2
C4—C5—H5	103.7	C20—C21—H21B	109.2
C10—C5—H5	103.7	H21A—C21—H21B	107.9
C5—C6—C7	110.3 (4)	C21—C22—C17	114.8 (4)
C5—C6—H6A	109.6	C21—C22—H22A	108.6
C7—C6—H6A	109.6	C17—C22—H22A	108.6
C5—C6—H6B	109.6	C21—C22—H22B	108.6
C7—C6—H6B	109.6	C17—C22—H22B	108.6
H6A—C6—H6B	108.1	H22A—C22—H22B	107.5
C8—C7—C6	111.6 (3)	C4—C23—H23A	109.5
C8—C7—H7A	109.3	C4—C23—H23B	109.5
C6—C7—H7A	109.3	H23A—C23—H23B	109.5
C8—C7—H7B	109.3	C4—C23—H23C	109.5
C6—C7—H7B	109.3	H23A—C23—H23C	109.5
H7A—C7—H7B	108.0	H23B—C23—H23C	109.5
C7—C8—C26	109.6 (4)	C4—C24—H24A	109.5
C7—C8—C9	109.8 (3)	C4—C24—H24B	109.5
C26—C8—C9	111.5 (3)	H24A—C24—H24B	109.5
C7—C8—C14	109.4 (3)	C4—C24—H24C	109.5
C26—C8—C14	107.9 (3)	H24A—C24—H24C	109.5
C9—C8—C14	108.7 (3)	H24B—C24—H24C	109.5
C11—C9—C8	110.0 (4)	C10—C25—H25A	109.5
C11—C9—C10	112.9 (3)	C10—C25—H25B	109.5
C8—C9—C10	116.3 (3)	H25A—C25—H25B	109.5
C11—C9—H9	105.5	C10—C25—H25C	109.5
C8—C9—H9	105.5	H25A—C25—H25C	109.5
C10—C9—H9	105.5	H25B—C25—H25C	109.5
C25—C10—C1	109.5 (4)	C8—C26—H26A	109.5
C25—C10—C5	112.3 (4)	C8—C26—H26B	109.5
C1—C10—C5	106.1 (4)	H26A—C26—H26B	109.5
C25—C10—C9	113.4 (3)	C8—C26—H26C	109.5
C1—C10—C9	106.5 (3)	H26A—C26—H26C	109.5
C5—C10—C9	108.6 (3)	H26B—C26—H26C	109.5
C12—C11—C9	113.2 (4)	O3—C27—O2	121.4 (4)
C12—C11—H11A	108.9	O3—C27—C14	124.6 (4)
C9—C11—H11A	108.9	O2—C27—C14	114.0 (4)
C12—C11—H11B	108.9	C17—C28—H28A	109.5
C9—C11—H11B	108.9	C17—C28—H28B	109.5
H11A—C11—H11B	107.8	H28A—C28—H28B	109.5
C13—C12—C11	126.7 (4)	C17—C28—H28C	109.5
C13—C12—H12	116.6	H28A—C28—H28C	109.5
C11—C12—H12	116.6	H28B—C28—H28C	109.5
C12—C13—C18	119.9 (4)	C20—C29—H29A	109.5
C12—C13—C14	119.9 (4)	C20—C29—H29B	109.5
C18—C13—C14	120.2 (4)	H29A—C29—H29B	109.5
C13—C14—C27	105.2 (4)	C20—C29—H29C	109.5
C13—C14—C15	109.7 (4)	H29A—C29—H29C	109.5
C27—C14—C15	108.4 (3)	H29B—C29—H29C	109.5
C13—C14—C8	111.1 (3)	C20—C30—H30A	109.5
C27—C14—C8	110.7 (3)	C20—C30—H30B	109.5
C15—C14—C8	111.4 (4)	H30A—C30—H30B	109.5
C16—C15—C14	115.1 (4)	C20—C30—H30C	109.5
C16—C15—H15A	108.5	H30A—C30—H30C	109.5
C14—C15—H15A	108.5	H30B—C30—H30C	109.5
C16—C15—H15B	108.5	C31—O4—H4O	109.5
C14—C15—H15B	108.5	O4—C31—H31A	109.5
H15A—C15—H15B	107.5	O4—C31—H31B	109.5
C15—C16—C17	112.1 (4)	H31A—C31—H31B	109.5
C15—C16—H16A	109.2	O4—C31—H31C	109.5
C17—C16—H16A	109.2	H31A—C31—H31C	109.5
C15—C16—H16B	109.2	H31B—C31—H31C	109.5

C10—C1—C2—C3	−57.4 (5)	C12—C13—C14—C15	−145.0 (4)
C1—C2—C3—O1	−178.2 (4)	C18—C13—C14—C15	36.6 (6)
C1—C2—C3—C4	56.6 (6)	C12—C13—C14—C8	−21.3 (6)
O1—C3—C4—C24	67.2 (5)	C18—C13—C14—C8	160.3 (3)
C2—C3—C4—C24	−170.2 (5)	C7—C8—C14—C13	171.4 (4)
O1—C3—C4—C23	−49.5 (5)	C26—C8—C14—C13	−69.4 (5)
C2—C3—C4—C23	73.0 (5)	C9—C8—C14—C13	51.6 (4)
O1—C3—C4—C5	−175.7 (3)	C7—C8—C14—C27	54.9 (4)
C2—C3—C4—C5	−53.1 (5)	C26—C8—C14—C27	174.1 (3)
C24—C4—C5—C6	−56.2 (5)	C9—C8—C14—C27	−64.9 (4)
C3—C4—C5—C6	−171.9 (4)	C7—C8—C14—C15	−65.9 (4)
C23—C4—C5—C6	64.1 (5)	C26—C8—C14—C15	53.3 (4)
C24—C4—C5—C10	170.2 (4)	C9—C8—C14—C15	174.3 (3)
C3—C4—C5—C10	54.5 (5)	C13—C14—C15—C16	−40.9 (5)
C23—C4—C5—C10	−69.5 (5)	C27—C14—C15—C16	73.5 (5)
C4—C5—C6—C7	160.7 (4)	C8—C14—C15—C16	−164.4 (4)
C10—C5—C6—C7	−63.0 (5)	C14—C15—C16—C17	56.1 (6)
C5—C6—C7—C8	62.1 (5)	C15—C16—C17—C28	60.5 (5)
C6—C7—C8—C26	70.0 (5)	C15—C16—C17—C22	178.7 (4)
C6—C7—C8—C9	−52.7 (5)	C15—C16—C17—C18	−60.3 (5)
C6—C7—C8—C14	−171.8 (3)	C12—C13—C18—C17	136.2 (4)
C7—C8—C9—C11	177.9 (4)	C14—C13—C18—C17	−45.4 (5)
C26—C8—C9—C11	56.3 (5)	C12—C13—C18—C19	−95.1 (5)
C14—C8—C9—C11	−62.5 (4)	C14—C13—C18—C19	83.3 (5)
C7—C8—C9—C10	47.9 (4)	C28—C17—C18—C13	−68.2 (5)
C26—C8—C9—C10	−73.7 (4)	C16—C17—C18—C13	54.0 (5)
C14—C8—C9—C10	167.5 (3)	C22—C17—C18—C13	174.9 (4)
C2—C1—C10—C25	−67.3 (5)	C28—C17—C18—C19	163.7 (4)
C2—C1—C10—C5	54.2 (5)	C16—C17—C18—C19	−74.1 (5)
C2—C1—C10—C9	169.8 (3)	C22—C17—C18—C19	46.8 (5)
C6—C5—C10—C25	−71.5 (5)	C13—C18—C19—C20	177.5 (4)
C4—C5—C10—C25	64.2 (5)	C17—C18—C19—C20	−53.8 (6)
C6—C5—C10—C1	168.9 (3)	C18—C19—C20—C30	175.2 (5)
C4—C5—C10—C1	−55.4 (5)	C18—C19—C20—C29	−66.5 (6)
C6—C5—C10—C9	54.7 (5)	C18—C19—C20—C21	56.4 (6)
C4—C5—C10—C9	−169.5 (3)	C19—C20—C21—C22	−56.3 (6)
C11—C9—C10—C25	−51.6 (5)	C30—C20—C21—C22	−174.3 (5)
C8—C9—C10—C25	77.0 (4)	C29—C20—C21—C22	67.0 (6)
C11—C9—C10—C1	68.9 (4)	C20—C21—C22—C17	55.6 (7)
C8—C9—C10—C1	−162.5 (3)	C28—C17—C22—C21	−168.2 (5)
C11—C9—C10—C5	−177.2 (4)	C16—C17—C22—C21	70.1 (6)
C8—C9—C10—C5	−48.6 (5)	C18—C17—C22—C21	−49.1 (6)
C8—C9—C11—C12	41.8 (5)	C13—C14—C27—O3	−42.0 (6)
C10—C9—C11—C12	173.6 (4)	C15—C14—C27—O3	−159.3 (4)
C9—C11—C12—C13	−10.6 (7)	C8—C14—C27—O3	78.1 (5)
C11—C12—C13—C18	178.7 (4)	C13—C14—C27—O2	139.9 (4)
C11—C12—C13—C14	0.3 (7)	C15—C14—C27—O2	22.5 (5)
C12—C13—C14—C27	98.5 (5)	C8—C14—C27—O2	−100.0 (4)
C18—C13—C14—C27	−79.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4	0.82	1.82	2.619 (5)	164
O1—H1···O3ⁱ	0.82	2.17	2.991 (5)	178
O4—H4O···O1ⁱ	0.82	1.96	2.755 (5)	164
C9—H9···O3	0.98	2.36	3.122 (5)	134
C15—H15B···O2	0.97	2.27	2.649 (5)	102
C24—H24A···O1	0.96	2.58	2.980 (6)	105

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₀H₄₈O₃·CH₄O
M_r	488.73
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	7.538 (2), 13.710 (3), 27.629 (8)
V (Å³)	2855.3 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.58 × 0.40 × 0.24

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3492, 3203, 1876
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.158, 0.89
No. of reflections	3203
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Siemens, 1991), SHELXL97.

Selected geometric parameters (Å, º) top

O1—C3	1.449 (5)	C12—C13	1.336 (6)
O2—C27	1.323 (5)	O4—C31	1.369 (8)
O3—C27	1.213 (5)

O1—C3—C2	107.5 (4)	C12—C13—C14	119.9 (4)
O1—C3—C4	112.4 (4)	C18—C13—C14	120.2 (4)
C6—C5—C4	115.8 (4)	C13—C14—C27	105.2 (4)
C4—C5—C10	116.9 (3)	C16—C15—C14	115.1 (4)
C8—C9—C10	116.3 (3)	O3—C27—O2	121.4 (4)
C13—C12—C11	126.7 (4)	O3—C27—C14	124.6 (4)
C12—C13—C18	119.9 (4)	O2—C27—C14	114.0 (4)

C1—C2—C3—O1	−178.2 (4)	C15—C14—C27—O3	−159.3 (4)
O1—C3—C4—C24	67.2 (5)	C8—C14—C27—O3	78.1 (5)
O1—C3—C4—C23	−49.5 (5)	C13—C14—C27—O2	139.9 (4)
O1—C3—C4—C5	−175.7 (3)	C15—C14—C27—O2	22.5 (5)
C13—C14—C27—O3	−42.0 (6)	C8—C14—C27—O2	−100.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4	0.82	1.82	2.619 (5)	164
O1—H1···O3ⁱ	0.82	2.17	2.991 (5)	178
O4—H4O···O1ⁱ	0.82	1.96	2.755 (5)	164
C9—H9···O3	0.98	2.36	3.122 (5)	134
C15—H15B···O2	0.97	2.27	2.649 (5)	102
C24—H24A···O1	0.96	2.58	2.980 (6)	105

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

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