organic compounds
(E)-3-(4-Hydroxy-3-methoxybenzylidene)-4-(4-hydroxyphenyl)pyrrolidin-2-one
aDepartment of Complex Prescription of TCM, China Pharmaceutical University, Nanjing 210038, People's Republic of China, and bDepartment of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, 210009, People's Republic of China
*Correspondence e-mail: boyangyu59@163.com
The title compound, C18H17NO4, was isolated from an ethanol extract of Ophiopogon japonicus. The dihedral angle between the 4-hydroxy-3-methoxyphenyl ring and the pyrrolidine ring is 17.4 (1)°. The 4-hydroxyphenyl ring makes a dihedral angle of 69.74 (6)° with the least-squares plane through the 4-hydroxy-3-methoxyphenyl ring and the pyrrolidine ring. The conformation of the pyrrolidine fragment is similar to a T-form. The is stabilized by intermolecular N—H⋯O and O—H⋯O hydrogen bonds.
Related literature
For the chemical components and pharmacological properties of the plant Ophiopogon japonicus, see: Anh et al. (2003); Kou et al. (2005) & Yu (2007). For related literature, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2001); cell SAINT; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808008581/lx2053sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008581/lx2053Isup2.hkl
Material from the dried subterranean parts of Ophiopogon japonicus (L. f.) Ker-Gawl.(Liliaceae) (40 kg),collected from Sichuan Province in China, was extracted with hot 60% EtOH (3×3 h) under refluxing. The concentrated extract was subjected to D-101 macroporous resin
eluted successively with EtOH-H2O(0:100, 30:70, 90:100) to give three fractions (I-III). The concentratedresidue of fraction III (EtOH-H2O, 90:10) (330 g) was further dissolved in water, and extractedwith EtOAc and n-BuOH successively. The EtOAc extract (107 g) was loaded onto a silica-gel column (200–300 mesh, 600 g) eluted with a gradientof 100% CHCl3 to CHCl3—MeOH (50:50) to give 18 fractions,which was pooled by common characteristics. Fraction9 was subjected to repeated over silica-gel and Sephadex LH-20columns, gave compound (I) (yield 6 mg, m.p. 518 K). Prismatic crystalssuitable for X-ray studies were grown from MeOH by slow evaporation at roomtemperature.Data collection: SMART (Bruker, 2001); cell
SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C18H17NO4 | F(000) = 656 |
Mr = 311.33 | Dx = 1.329 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1858 reflections |
a = 6.388 (1) Å | θ = 2.4–23.1° |
b = 14.520 (2) Å | µ = 0.09 mm−1 |
c = 16.880 (2) Å | T = 298 K |
β = 96.514 (2)° | Block, colourless |
V = 1555.6 (4) Å3 | 0.47 × 0.42 × 0.35 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3387 independent reflections |
Radiation source: fine-focus sealed tube | 1756 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.0°, θmin = 1.9° |
ϕ and ω scans | h = −8→7 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | k = −13→18 |
Tmin = 0.954, Tmax = 0.969 | l = −20→21 |
9225 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0524P)2 + 0.295P] where P = (Fo2 + 2Fc2)/3 |
3387 reflections | (Δ/σ)max < 0.000 |
209 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C18H17NO4 | V = 1555.6 (4) Å3 |
Mr = 311.33 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.388 (1) Å | µ = 0.09 mm−1 |
b = 14.520 (2) Å | T = 298 K |
c = 16.880 (2) Å | 0.47 × 0.42 × 0.35 mm |
β = 96.514 (2)° |
Bruker SMART CCD area-detector diffractometer | 3387 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | 1756 reflections with I > 2σ(I) |
Tmin = 0.954, Tmax = 0.969 | Rint = 0.041 |
9225 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.22 e Å−3 |
3387 reflections | Δρmin = −0.20 e Å−3 |
209 parameters |
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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
N | 0.1955 (3) | 0.50621 (13) | 0.43227 (10) | 0.0407 (5) | |
H1 | 0.1694 | 0.5304 | 0.4766 | 0.049* | |
O1 | −0.1146 (2) | 0.42888 (11) | 0.40852 (9) | 0.0482 (4) | |
O2 | 0.3756 (3) | 0.78432 (11) | 0.09921 (11) | 0.0678 (6) | |
H2 | 0.2621 | 0.8112 | 0.0921 | 0.102* | |
O3 | 0.5094 (3) | 0.35253 (12) | 0.04340 (10) | 0.0600 (5) | |
O4 | 0.2796 (3) | 0.20997 (13) | −0.01836 (11) | 0.0762 (6) | |
H4 | 0.3957 | 0.2277 | −0.0283 | 0.114* | |
C1 | 0.0580 (4) | 0.45390 (14) | 0.38830 (13) | 0.0372 (5) | |
C2 | 0.1463 (3) | 0.43166 (15) | 0.31329 (12) | 0.0358 (5) | |
C3 | 0.3493 (3) | 0.48408 (15) | 0.31322 (12) | 0.0382 (5) | |
H3 | 0.4610 | 0.4408 | 0.3031 | 0.046* | |
C4 | 0.3928 (4) | 0.5193 (2) | 0.39970 (13) | 0.0536 (7) | |
H4A | 0.5045 | 0.4840 | 0.4294 | 0.064* | |
H4B | 0.4325 | 0.5838 | 0.4008 | 0.064* | |
C5 | 0.3457 (3) | 0.56253 (15) | 0.25340 (12) | 0.0365 (5) | |
C6 | 0.1668 (4) | 0.59272 (15) | 0.20783 (14) | 0.0433 (6) | |
H6 | 0.0395 | 0.5631 | 0.2121 | 0.052* | |
C7 | 0.1720 (4) | 0.66655 (16) | 0.15552 (14) | 0.0472 (6) | |
H7 | 0.0495 | 0.6858 | 0.1250 | 0.057* | |
C8 | 0.3594 (4) | 0.71071 (16) | 0.14939 (14) | 0.0476 (6) | |
C9 | 0.5397 (4) | 0.68061 (18) | 0.19335 (17) | 0.0562 (7) | |
H9 | 0.6671 | 0.7098 | 0.1884 | 0.067* | |
C10 | 0.5334 (4) | 0.60767 (17) | 0.24462 (15) | 0.0523 (7) | |
H10 | 0.6572 | 0.5880 | 0.2741 | 0.063* | |
C11 | 0.0515 (4) | 0.37125 (15) | 0.26114 (13) | 0.0401 (6) | |
H11 | −0.0771 | 0.3493 | 0.2741 | 0.048* | |
C12 | 0.1159 (4) | 0.33400 (15) | 0.18741 (13) | 0.0396 (6) | |
C13 | 0.2897 (4) | 0.36572 (15) | 0.15170 (13) | 0.0419 (6) | |
H13 | 0.3690 | 0.4145 | 0.1747 | 0.050* | |
C14 | 0.3449 (4) | 0.32596 (16) | 0.08338 (13) | 0.0431 (6) | |
C15 | 0.2293 (4) | 0.25225 (17) | 0.04909 (14) | 0.0507 (7) | |
C16 | 0.0567 (4) | 0.22166 (18) | 0.08261 (15) | 0.0619 (8) | |
H16 | −0.0229 | 0.1732 | 0.0591 | 0.074* | |
C17 | −0.0002 (4) | 0.26206 (17) | 0.15097 (14) | 0.0536 (7) | |
H17 | −0.1182 | 0.2407 | 0.1729 | 0.064* | |
C18 | 0.6343 (4) | 0.4276 (2) | 0.07462 (17) | 0.0672 (8) | |
H18A | 0.5482 | 0.4818 | 0.0749 | 0.101* | |
H18B | 0.7457 | 0.4382 | 0.0420 | 0.101* | |
H18C | 0.6937 | 0.4137 | 0.1281 | 0.101* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N | 0.0424 (11) | 0.0505 (12) | 0.0299 (10) | 0.0051 (9) | 0.0069 (8) | −0.0053 (9) |
O1 | 0.0476 (10) | 0.0547 (11) | 0.0451 (10) | −0.0041 (8) | 0.0177 (8) | −0.0079 (8) |
O2 | 0.0807 (14) | 0.0491 (11) | 0.0812 (14) | 0.0105 (10) | 0.0418 (11) | 0.0189 (10) |
O3 | 0.0623 (11) | 0.0676 (12) | 0.0549 (11) | −0.0166 (10) | 0.0276 (9) | −0.0155 (9) |
O4 | 0.0992 (15) | 0.0755 (13) | 0.0612 (12) | −0.0284 (11) | 0.0411 (11) | −0.0326 (10) |
C1 | 0.0417 (13) | 0.0371 (13) | 0.0333 (12) | 0.0044 (11) | 0.0064 (10) | −0.0001 (10) |
C2 | 0.0380 (12) | 0.0397 (13) | 0.0300 (12) | 0.0038 (10) | 0.0053 (10) | 0.0047 (10) |
C3 | 0.0396 (13) | 0.0456 (14) | 0.0298 (12) | 0.0048 (11) | 0.0053 (10) | −0.0016 (10) |
C4 | 0.0417 (14) | 0.085 (2) | 0.0340 (14) | −0.0061 (13) | 0.0032 (11) | −0.0047 (13) |
C5 | 0.0387 (13) | 0.0396 (13) | 0.0319 (12) | −0.0006 (10) | 0.0071 (10) | −0.0053 (10) |
C6 | 0.0380 (13) | 0.0444 (14) | 0.0483 (15) | −0.0005 (11) | 0.0087 (11) | 0.0033 (11) |
C7 | 0.0463 (15) | 0.0490 (15) | 0.0466 (15) | 0.0082 (12) | 0.0070 (12) | 0.0062 (12) |
C8 | 0.0598 (17) | 0.0367 (14) | 0.0506 (15) | 0.0017 (12) | 0.0251 (13) | 0.0006 (11) |
C9 | 0.0492 (16) | 0.0550 (17) | 0.0660 (18) | −0.0134 (13) | 0.0137 (14) | 0.0001 (14) |
C10 | 0.0410 (15) | 0.0613 (17) | 0.0540 (16) | −0.0058 (13) | 0.0026 (12) | 0.0039 (13) |
C11 | 0.0427 (14) | 0.0413 (13) | 0.0373 (13) | −0.0026 (11) | 0.0090 (11) | 0.0029 (10) |
C12 | 0.0480 (14) | 0.0402 (13) | 0.0314 (12) | −0.0016 (11) | 0.0077 (10) | −0.0009 (10) |
C13 | 0.0490 (14) | 0.0412 (13) | 0.0361 (13) | −0.0059 (11) | 0.0073 (11) | −0.0052 (10) |
C14 | 0.0497 (14) | 0.0435 (14) | 0.0376 (13) | −0.0030 (11) | 0.0117 (11) | −0.0006 (11) |
C15 | 0.0682 (18) | 0.0477 (15) | 0.0384 (14) | −0.0065 (13) | 0.0164 (13) | −0.0084 (11) |
C16 | 0.079 (2) | 0.0590 (18) | 0.0512 (16) | −0.0282 (15) | 0.0212 (14) | −0.0149 (13) |
C17 | 0.0654 (18) | 0.0560 (16) | 0.0424 (15) | −0.0190 (13) | 0.0198 (13) | −0.0089 (12) |
C18 | 0.0575 (18) | 0.079 (2) | 0.0671 (19) | −0.0173 (16) | 0.0167 (15) | −0.0032 (16) |
N—C1 | 1.323 (3) | C6—H6 | 0.9300 |
N—C4 | 1.444 (3) | C7—C8 | 1.372 (3) |
N—H1 | 0.8600 | C7—H7 | 0.9300 |
O1—C1 | 1.245 (2) | C8—C9 | 1.369 (3) |
O2—C8 | 1.375 (3) | C9—C10 | 1.371 (3) |
O2—H2 | 0.8200 | C9—H9 | 0.9300 |
O3—C14 | 1.367 (3) | C10—H10 | 0.9300 |
O3—C18 | 1.417 (3) | C11—C12 | 1.458 (3) |
O4—C15 | 1.364 (3) | C11—H11 | 0.9300 |
O4—H4 | 0.8200 | C12—C17 | 1.384 (3) |
C1—C2 | 1.479 (3) | C12—C13 | 1.400 (3) |
C2—C11 | 1.338 (3) | C13—C14 | 1.371 (3) |
C2—C3 | 1.504 (3) | C13—H13 | 0.9300 |
C3—C5 | 1.521 (3) | C14—C15 | 1.389 (3) |
C3—C4 | 1.542 (3) | C15—C16 | 1.369 (3) |
C3—H3 | 0.9800 | C16—C17 | 1.379 (3) |
C4—H4A | 0.9700 | C16—H16 | 0.9300 |
C4—H4B | 0.9700 | C17—H17 | 0.9300 |
C5—C6 | 1.375 (3) | C18—H18A | 0.9600 |
C5—C10 | 1.389 (3) | C18—H18B | 0.9600 |
C6—C7 | 1.392 (3) | C18—H18C | 0.9600 |
C1—N—C4 | 114.5 (2) | C7—C8—O2 | 122.5 (2) |
C1—N—H1 | 122.8 | C8—C9—C10 | 120.4 (2) |
C4—N—H1 | 122.8 | C8—C9—H9 | 119.8 |
C8—O2—H2 | 109.5 | C10—C9—H9 | 119.8 |
C14—O3—C18 | 117.7 (2) | C9—C10—C5 | 121.3 (2) |
C15—O4—H4 | 109.5 | C9—C10—H10 | 119.4 |
O1—C1—N | 124.4 (2) | C5—C10—H10 | 119.4 |
O1—C1—C2 | 127.4 (2) | C2—C11—C12 | 130.9 (2) |
N—C1—C2 | 108.20 (19) | C2—C11—H11 | 114.6 |
C11—C2—C1 | 121.2 (2) | C12—C11—H11 | 114.6 |
C11—C2—C3 | 131.1 (2) | C17—C12—C13 | 117.9 (2) |
C1—C2—C3 | 107.6 (2) | C17—C12—C11 | 118.1 (2) |
C2—C3—C5 | 115.6 (2) | C13—C12—C11 | 124.0 (2) |
C2—C3—C4 | 103.3 (2) | C14—C13—C12 | 121.0 (2) |
C5—C3—C4 | 111.6 (2) | C14—C13—H13 | 119.5 |
C2—C3—H3 | 108.7 | C12—C13—H13 | 119.5 |
C5—C3—H3 | 108.7 | O3—C14—C13 | 125.6 (2) |
C4—C3—H3 | 108.7 | O3—C14—C15 | 114.4 (2) |
N—C4—C3 | 104.2 (2) | C13—C14—C15 | 120.0 (2) |
N—C4—H4A | 110.9 | O4—C15—C16 | 118.4 (2) |
C3—C4—H4A | 110.9 | O4—C15—C14 | 122.0 (2) |
N—C4—H4B | 110.9 | C16—C15—C14 | 119.5 (2) |
C3—C4—H4B | 110.9 | C15—C16—C17 | 120.6 (2) |
H4A—C4—H4B | 108.9 | C15—C16—H16 | 119.7 |
C6—C5—C10 | 117.5 (2) | C17—C16—H16 | 119.7 |
C6—C5—C3 | 124.0 (2) | C16—C17—C12 | 120.9 (2) |
C10—C5—C3 | 118.4 (2) | C16—C17—H17 | 119.5 |
C5—C6—C7 | 121.5 (2) | C12—C17—H17 | 119.5 |
C5—C6—H6 | 119.2 | O3—C18—H18A | 109.5 |
C7—C6—H6 | 119.2 | O3—C18—H18B | 109.5 |
C8—C7—C6 | 119.4 (2) | H18A—C18—H18B | 109.5 |
C8—C7—H7 | 120.3 | O3—C18—H18C | 109.5 |
C6—C7—H7 | 120.3 | H18A—C18—H18C | 109.5 |
C9—C8—C7 | 119.8 (2) | H18B—C18—H18C | 109.5 |
C9—C8—O2 | 117.7 (2) | ||
C4—N—C1—O1 | 174.6 (2) | O2—C8—C9—C10 | 179.8 (2) |
C4—N—C1—C2 | −5.3 (3) | C8—C9—C10—C5 | 0.0 (4) |
O1—C1—C2—C11 | −7.4 (4) | C6—C5—C10—C9 | 1.0 (3) |
N—C1—C2—C11 | 172.5 (2) | C3—C5—C10—C9 | −178.1 (2) |
O1—C1—C2—C3 | 175.2 (2) | C1—C2—C11—C12 | −175.0 (2) |
N—C1—C2—C3 | −4.9 (2) | C3—C2—C11—C12 | 1.8 (4) |
C11—C2—C3—C5 | 72.8 (3) | C2—C11—C12—C17 | 170.9 (2) |
C1—C2—C3—C5 | −110.1 (2) | C2—C11—C12—C13 | −8.2 (4) |
C11—C2—C3—C4 | −165.1 (2) | C17—C12—C13—C14 | −0.9 (4) |
C1—C2—C3—C4 | 12.0 (2) | C11—C12—C13—C14 | 178.3 (2) |
C1—N—C4—C3 | 12.9 (3) | C18—O3—C14—C13 | −0.1 (4) |
C2—C3—C4—N | −14.5 (2) | C18—O3—C14—C15 | 179.8 (2) |
C5—C3—C4—N | 110.3 (2) | C12—C13—C14—O3 | 179.0 (2) |
C2—C3—C5—C6 | 7.3 (3) | C12—C13—C14—C15 | −0.8 (4) |
C4—C3—C5—C6 | −110.3 (2) | O3—C14—C15—O4 | 0.8 (4) |
C2—C3—C5—C10 | −173.59 (19) | C13—C14—C15—O4 | −179.3 (2) |
C4—C3—C5—C10 | 68.8 (2) | O3—C14—C15—C16 | −177.9 (2) |
C10—C5—C6—C7 | −0.9 (3) | C13—C14—C15—C16 | 2.0 (4) |
C3—C5—C6—C7 | 178.2 (2) | O4—C15—C16—C17 | 179.8 (2) |
C5—C6—C7—C8 | −0.3 (3) | C14—C15—C16—C17 | −1.5 (4) |
C6—C7—C8—C9 | 1.4 (4) | C15—C16—C17—C12 | −0.3 (4) |
C6—C7—C8—O2 | −179.7 (2) | C13—C12—C17—C16 | 1.4 (4) |
C7—C8—C9—C10 | −1.2 (4) | C11—C12—C17—C16 | −177.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1···O1i | 0.86 | 2.09 | 2.948 (2) | 172 |
O2—H2···O1ii | 0.82 | 1.95 | 2.675 (2) | 147 |
O4—H4···O2iii | 0.82 | 2.00 | 2.721 (2) | 147 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C18H17NO4 |
Mr | 311.33 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 6.388 (1), 14.520 (2), 16.880 (2) |
β (°) | 96.514 (2) |
V (Å3) | 1555.6 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.47 × 0.42 × 0.35 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1999) |
Tmin, Tmax | 0.954, 0.969 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9225, 3387, 1756 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.137, 1.02 |
No. of reflections | 3387 |
No. of parameters | 209 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.20 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1···O1i | 0.86 | 2.09 | 2.948 (2) | 172.0 |
O2—H2···O1ii | 0.82 | 1.95 | 2.675 (2) | 146.7 |
O4—H4···O2iii | 0.82 | 2.00 | 2.721 (2) | 146.5 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z. |
Acknowledgements
This research was financially supported by the National Natural Science Foundation of China (grant No. 30672603 to Dr Bo-Yang Yu).
References
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The plant of Ophiopogon japonicus (L. f.) Ker-Gawl.(Liliaceae) is widely distributed in South-east Asia, especially in most areaof China, and its tuber root as a famous traditional medicine are widely usedin China to cure acute and chronic inflammation and cardiovascular diseasesincluding thrombotic diseases for thousands of years (Yu, 2007; Kou, et al., 2005). Chemical studies have shown that this plant includes steroidal saponins, homoisoflavonoids andmonoterpene glycosides etc (Anh, et al., 2003). Herein we report the molecular and crystal structure of the title compound (Fig.1), which was isolated from an ethanol extract of the plant of Ophiopogon japonicus.
The main components of the title compound were two aromatic rings, A(C5—C10) and B(C12—C17) and a pyrrolidine ring C(N1/C1—C4) as shown in Fig. 1. Fig. 2 presents the packing diagram of the title compound. Paired molecules at the inversional position assembled via supromolecular sython R22(8) (Bernstein, et al., 1995) which consist of hydrogen bonds N1—H1···O1i, O2—H2···O1ii and O4—H4···O2iii (Symmetry code as in Fig. 2.).