A new iridoid glycoside, methyl (3
R,4
R,4a
S,7
S,7a
R)-3-hydroxy-7-methyl-5-oxooctahydrocyclopenta[
c]pyran-4-carboxylate-3-
O-β-
D-(1′
S,2′
R,3′
S,4′
S,5′
R)-glucopyranoside, named loniceroside A, C
17H
26O
10, (
1), was obtained from the aerial parts of
Lonicera saccata. Its structure was established based on an analysis of spectroscopic data, including 1D NMR, 2D NMR and HRESIMS, and the configurations of the chiral C atoms were determined by X-ray crystallographic analysis. The single-crystal structure reveals that the cyclopenta[
c]pyran scaffold is formed from a five-membered ring and a chair-like six-membered ring connected through two bridgehead chiral C atoms. In the solid state, the glucose group of (
1) plays an important role in constructing an unusual supramolecular motif. The structure analysis revealed adjacent molecules linked together through intermolecular O—H
O hydrogen bonds to generate a banded structure. Furthermore, the banded structures are linked into a three-dimensional network by interesting hydrogen bonds. Biogenetically, compound (
1) carries a glucopyranosyloxy moiety at the C-3 position, representing a rare structural feature for naturally occurring iridoid glycosides. The growth inhibitory effects against human cervical carcinoma cells (Hela), human lung adenocarcinoma cells (A549), human acute mononuclear granulocyte leukaemia (THP-1) and the human liver hepatocellular carcinoma cell line (HepG2) were evaluated by the MTT method.
Supporting information
CCDC reference: 1945812
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT2017 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
(3
R,4
R,4a
S,7
S,7a
R)-3-Hydroxy-7-methyl-5-oxooctahydrocyclopenta[
c]pyran-4-carboxylate-3-
O-
β-
D-(1'
S,2'
R,3'
S,4'
S,5'
R)-glucopyranoside
top
Crystal data top
C17H26O10 | Dx = 1.469 Mg m−3 |
Mr = 390.38 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, P212121 | Cell parameters from 6911 reflections |
a = 8.1545 (1) Å | θ = 2.8–73.4° |
b = 13.8326 (1) Å | µ = 1.04 mm−1 |
c = 15.6478 (2) Å | T = 100 K |
V = 1765.04 (3) Å3 | Block, colourless |
Z = 4 | 0.14 × 0.12 × 0.11 mm |
F(000) = 832 | |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an AtlasS2 detector | 3265 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 3220 reflections with I > 2σ(I) |
Detector resolution: 5.2684 pixels mm-1 | Rint = 0.017 |
CCD plate scans | θmax = 73.5°, θmin = 4.3° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −6→9 |
Tmin = 0.772, Tmax = 1.000 | k = −11→17 |
7835 measured reflections | l = −19→19 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.027 | w = 1/[σ2(Fo2) + (0.0408P)2 + 0.3089P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.070 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.14 e Å−3 |
3265 reflections | Δρmin = −0.23 e Å−3 |
250 parameters | Absolute structure: Flack x determined using 1242 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.03 (6) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.8825 (2) | 0.33241 (13) | 0.09344 (11) | 0.0154 (4) | |
H1A | 0.875944 | 0.268086 | 0.117894 | 0.018* | |
H1B | 0.992469 | 0.341104 | 0.071146 | 0.018* | |
C2 | 0.6965 (2) | 0.39603 (12) | 0.19570 (11) | 0.0128 (3) | |
H2 | 0.686687 | 0.444364 | 0.241207 | 0.015* | |
C3 | 0.5620 (2) | 0.41489 (12) | 0.12919 (10) | 0.0117 (3) | |
H3 | 0.571877 | 0.482042 | 0.109918 | 0.014* | |
C4 | 0.5804 (2) | 0.34860 (12) | 0.05068 (10) | 0.0113 (3) | |
H4 | 0.533310 | 0.284619 | 0.061697 | 0.014* | |
C5 | 0.4938 (2) | 0.39817 (12) | −0.02397 (11) | 0.0130 (3) | |
C6 | 0.6211 (2) | 0.43206 (14) | −0.08765 (11) | 0.0179 (4) | |
H6A | 0.598267 | 0.497701 | −0.105936 | 0.022* | |
H6B | 0.622410 | 0.390352 | −0.137476 | 0.022* | |
C7 | 0.7854 (2) | 0.42707 (13) | −0.04023 (11) | 0.0150 (4) | |
H7 | 0.798579 | 0.485891 | −0.006003 | 0.018* | |
C8 | 0.7604 (2) | 0.34036 (13) | 0.02049 (11) | 0.0126 (3) | |
H8 | 0.769509 | 0.281305 | −0.013770 | 0.015* | |
C9 | 0.9327 (2) | 0.41669 (14) | −0.09931 (11) | 0.0184 (4) | |
H9A | 0.917701 | 0.361397 | −0.135556 | 0.028* | |
H9B | 1.030270 | 0.408411 | −0.065782 | 0.028* | |
H9C | 0.942982 | 0.473728 | −0.133855 | 0.028* | |
C10 | 0.3951 (2) | 0.40290 (13) | 0.17150 (11) | 0.0136 (4) | |
C11 | 0.2243 (3) | 0.46925 (15) | 0.27950 (12) | 0.0218 (4) | |
H11A | 0.132797 | 0.451772 | 0.244151 | 0.033* | |
H11B | 0.203874 | 0.530922 | 0.305547 | 0.033* | |
H11C | 0.239032 | 0.421302 | 0.323186 | 0.033* | |
C1' | 0.7413 (2) | 0.28047 (12) | 0.30756 (10) | 0.0123 (3) | |
H1' | 0.768956 | 0.339580 | 0.338927 | 0.015* | |
C2' | 0.6231 (2) | 0.21843 (13) | 0.35974 (11) | 0.0136 (3) | |
H2' | 0.585600 | 0.163832 | 0.324941 | 0.016* | |
C3' | 0.7077 (2) | 0.18070 (13) | 0.43929 (11) | 0.0143 (4) | |
H3' | 0.733267 | 0.235391 | 0.476799 | 0.017* | |
C4' | 0.8668 (2) | 0.12993 (13) | 0.41514 (11) | 0.0145 (4) | |
H4' | 0.838725 | 0.074679 | 0.378776 | 0.017* | |
C5' | 0.9738 (2) | 0.19821 (13) | 0.36269 (11) | 0.0139 (4) | |
H5' | 1.003701 | 0.254842 | 0.396952 | 0.017* | |
C6' | 1.1266 (2) | 0.14760 (13) | 0.33143 (12) | 0.0171 (4) | |
H6'1 | 1.180256 | 0.116703 | 0.379546 | 0.021* | |
H6'2 | 1.095381 | 0.097388 | 0.291334 | 0.021* | |
O1 | 0.85326 (15) | 0.40307 (9) | 0.15992 (8) | 0.0143 (3) | |
O2 | 0.66240 (15) | 0.30343 (8) | 0.23077 (8) | 0.0132 (3) | |
O3 | 0.37105 (16) | 0.47493 (9) | 0.22765 (8) | 0.0170 (3) | |
O4 | 0.29929 (16) | 0.33827 (9) | 0.15891 (8) | 0.0173 (3) | |
O5 | 0.34744 (16) | 0.41156 (10) | −0.02954 (8) | 0.0186 (3) | |
O6 | 0.88595 (15) | 0.22801 (9) | 0.28735 (8) | 0.0143 (3) | |
O7 | 0.48610 (16) | 0.27566 (10) | 0.38412 (8) | 0.0189 (3) | |
H7A | 0.407097 | 0.261764 | 0.354113 | 0.028* | |
O8 | 0.59971 (17) | 0.11647 (10) | 0.48326 (9) | 0.0205 (3) | |
H8A | 0.653423 | 0.074241 | 0.507118 | 0.031* | |
O9 | 0.94861 (17) | 0.09380 (10) | 0.48831 (8) | 0.0185 (3) | |
H9 | 0.957093 | 0.136930 | 0.523985 | 0.028* | |
O10 | 1.23965 (17) | 0.21100 (10) | 0.29105 (9) | 0.0223 (3) | |
H10 | 1.193244 | 0.240275 | 0.252427 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0124 (8) | 0.0195 (9) | 0.0143 (8) | 0.0031 (7) | 0.0002 (7) | −0.0020 (7) |
C2 | 0.0113 (8) | 0.0135 (8) | 0.0135 (7) | −0.0004 (7) | 0.0001 (7) | 0.0010 (6) |
C3 | 0.0102 (8) | 0.0122 (7) | 0.0128 (7) | 0.0007 (7) | 0.0001 (7) | 0.0001 (6) |
C4 | 0.0101 (8) | 0.0123 (7) | 0.0115 (7) | −0.0009 (7) | −0.0004 (7) | −0.0002 (6) |
C5 | 0.0140 (8) | 0.0116 (8) | 0.0135 (8) | −0.0006 (7) | −0.0021 (7) | −0.0029 (6) |
C6 | 0.0159 (9) | 0.0222 (9) | 0.0156 (8) | −0.0001 (8) | −0.0009 (8) | 0.0040 (7) |
C7 | 0.0130 (9) | 0.0163 (8) | 0.0156 (8) | −0.0009 (7) | 0.0005 (7) | −0.0003 (7) |
C8 | 0.0105 (8) | 0.0146 (8) | 0.0129 (8) | 0.0008 (7) | −0.0003 (7) | −0.0014 (7) |
C9 | 0.0153 (9) | 0.0229 (9) | 0.0172 (8) | −0.0022 (8) | 0.0026 (8) | 0.0015 (7) |
C10 | 0.0127 (8) | 0.0165 (8) | 0.0116 (7) | 0.0034 (8) | −0.0009 (7) | 0.0016 (6) |
C11 | 0.0173 (10) | 0.0293 (10) | 0.0187 (9) | 0.0056 (9) | 0.0062 (8) | −0.0020 (8) |
C1' | 0.0101 (8) | 0.0153 (8) | 0.0116 (7) | 0.0016 (7) | −0.0022 (6) | −0.0001 (6) |
C2' | 0.0096 (8) | 0.0165 (8) | 0.0147 (8) | 0.0012 (7) | −0.0002 (7) | −0.0008 (6) |
C3' | 0.0139 (8) | 0.0157 (8) | 0.0132 (8) | −0.0020 (7) | 0.0017 (7) | 0.0010 (7) |
C4' | 0.0141 (8) | 0.0156 (8) | 0.0137 (7) | 0.0008 (7) | −0.0026 (7) | 0.0009 (6) |
C5' | 0.0119 (8) | 0.0154 (8) | 0.0145 (7) | 0.0005 (7) | −0.0033 (7) | 0.0014 (7) |
C6' | 0.0127 (8) | 0.0183 (8) | 0.0204 (8) | 0.0006 (7) | 0.0007 (7) | 0.0032 (7) |
O1 | 0.0104 (6) | 0.0174 (6) | 0.0149 (5) | 0.0007 (5) | −0.0005 (5) | −0.0019 (5) |
O2 | 0.0135 (6) | 0.0144 (6) | 0.0117 (5) | −0.0002 (5) | −0.0035 (5) | 0.0015 (5) |
O3 | 0.0137 (6) | 0.0211 (6) | 0.0161 (6) | 0.0029 (6) | 0.0023 (5) | −0.0042 (5) |
O4 | 0.0132 (6) | 0.0215 (6) | 0.0174 (6) | −0.0033 (6) | 0.0012 (5) | −0.0008 (5) |
O5 | 0.0119 (6) | 0.0251 (7) | 0.0188 (6) | 0.0012 (6) | −0.0029 (5) | 0.0013 (5) |
O6 | 0.0112 (6) | 0.0190 (6) | 0.0127 (5) | 0.0026 (5) | −0.0006 (5) | 0.0024 (5) |
O7 | 0.0116 (6) | 0.0268 (7) | 0.0184 (6) | 0.0046 (6) | 0.0001 (5) | −0.0016 (5) |
O8 | 0.0176 (7) | 0.0227 (7) | 0.0211 (6) | −0.0021 (6) | 0.0042 (6) | 0.0078 (5) |
O9 | 0.0210 (7) | 0.0192 (6) | 0.0153 (6) | 0.0033 (6) | −0.0037 (6) | 0.0028 (5) |
O10 | 0.0123 (6) | 0.0295 (7) | 0.0251 (7) | −0.0017 (6) | 0.0006 (6) | 0.0076 (6) |
Geometric parameters (Å, º) top
C1—O1 | 1.447 (2) | C11—O3 | 1.448 (2) |
C1—C8 | 1.519 (2) | C11—H11A | 0.9600 |
C1—H1A | 0.9700 | C11—H11B | 0.9600 |
C1—H1B | 0.9700 | C11—H11C | 0.9600 |
C2—O1 | 1.399 (2) | C1'—O2 | 1.399 (2) |
C2—O2 | 1.421 (2) | C1'—O6 | 1.421 (2) |
C2—C3 | 1.535 (2) | C1'—C2' | 1.527 (2) |
C2—H2 | 0.9800 | C1'—H1' | 0.9800 |
C3—C10 | 1.522 (2) | C2'—O7 | 1.421 (2) |
C3—C4 | 1.540 (2) | C2'—C3' | 1.516 (2) |
C3—H3 | 0.9800 | C2'—H2' | 0.9800 |
C4—C5 | 1.527 (2) | C3'—O8 | 1.428 (2) |
C4—C8 | 1.546 (2) | C3'—C4' | 1.523 (3) |
C4—H4 | 0.9800 | C3'—H3' | 0.9800 |
C5—O5 | 1.211 (2) | C4'—O9 | 1.416 (2) |
C5—C6 | 1.513 (3) | C4'—C5' | 1.525 (2) |
C6—C7 | 1.533 (3) | C4'—H4' | 0.9800 |
C6—H6A | 0.9700 | C5'—O6 | 1.440 (2) |
C6—H6B | 0.9700 | C5'—C6' | 1.510 (3) |
C7—C9 | 1.523 (3) | C5'—H5' | 0.9800 |
C7—C8 | 1.544 (2) | C6'—O10 | 1.420 (2) |
C7—H7 | 0.9800 | C6'—H6'1 | 0.9700 |
C8—H8 | 0.9800 | C6'—H6'2 | 0.9700 |
C9—H9A | 0.9600 | O7—H7A | 0.8200 |
C9—H9B | 0.9600 | O8—H8A | 0.8200 |
C9—H9C | 0.9600 | O9—H9 | 0.8200 |
C10—O4 | 1.204 (2) | O10—H10 | 0.8200 |
C10—O3 | 1.343 (2) | | |
| | | |
O1—C1—C8 | 112.55 (14) | O4—C10—C3 | 126.16 (16) |
O1—C1—H1A | 109.1 | O3—C10—C3 | 109.54 (15) |
C8—C1—H1A | 109.1 | O3—C11—H11A | 109.5 |
O1—C1—H1B | 109.1 | O3—C11—H11B | 109.5 |
C8—C1—H1B | 109.1 | H11A—C11—H11B | 109.5 |
H1A—C1—H1B | 107.8 | O3—C11—H11C | 109.5 |
O1—C2—O2 | 113.34 (14) | H11A—C11—H11C | 109.5 |
O1—C2—C3 | 111.72 (14) | H11B—C11—H11C | 109.5 |
O2—C2—C3 | 105.96 (14) | O2—C1'—O6 | 107.85 (13) |
O1—C2—H2 | 108.6 | O2—C1'—C2' | 107.25 (13) |
O2—C2—H2 | 108.6 | O6—C1'—C2' | 110.86 (14) |
C3—C2—H2 | 108.6 | O2—C1'—H1' | 110.3 |
C10—C3—C2 | 109.01 (13) | O6—C1'—H1' | 110.3 |
C10—C3—C4 | 111.67 (14) | C2'—C1'—H1' | 110.3 |
C2—C3—C4 | 111.72 (14) | O7—C2'—C3' | 109.21 (14) |
C10—C3—H3 | 108.1 | O7—C2'—C1' | 109.06 (14) |
C2—C3—H3 | 108.1 | C3'—C2'—C1' | 110.21 (14) |
C4—C3—H3 | 108.1 | O7—C2'—H2' | 109.4 |
C5—C4—C3 | 107.32 (13) | C3'—C2'—H2' | 109.4 |
C5—C4—C8 | 103.77 (13) | C1'—C2'—H2' | 109.4 |
C3—C4—C8 | 112.34 (14) | O8—C3'—C2' | 109.24 (15) |
C5—C4—H4 | 111.0 | O8—C3'—C4' | 110.98 (14) |
C3—C4—H4 | 111.0 | C2'—C3'—C4' | 110.04 (14) |
C8—C4—H4 | 111.0 | O8—C3'—H3' | 108.8 |
O5—C5—C6 | 125.53 (17) | C2'—C3'—H3' | 108.8 |
O5—C5—C4 | 125.39 (16) | C4'—C3'—H3' | 108.8 |
C6—C5—C4 | 109.02 (15) | O9—C4'—C3' | 111.31 (14) |
C5—C6—C7 | 105.45 (14) | O9—C4'—C5' | 112.59 (15) |
C5—C6—H6A | 110.7 | C3'—C4'—C5' | 109.59 (14) |
C7—C6—H6A | 110.7 | O9—C4'—H4' | 107.7 |
C5—C6—H6B | 110.7 | C3'—C4'—H4' | 107.7 |
C7—C6—H6B | 110.7 | C5'—C4'—H4' | 107.7 |
H6A—C6—H6B | 108.8 | O6—C5'—C6' | 106.15 (14) |
C9—C7—C6 | 113.56 (15) | O6—C5'—C4' | 109.45 (14) |
C9—C7—C8 | 113.87 (15) | C6'—C5'—C4' | 111.04 (15) |
C6—C7—C8 | 102.57 (14) | O6—C5'—H5' | 110.0 |
C9—C7—H7 | 108.9 | C6'—C5'—H5' | 110.0 |
C6—C7—H7 | 108.9 | C4'—C5'—H5' | 110.0 |
C8—C7—H7 | 108.9 | O10—C6'—C5' | 113.15 (15) |
C1—C8—C7 | 115.61 (15) | O10—C6'—H6'1 | 108.9 |
C1—C8—C4 | 113.46 (14) | C5'—C6'—H6'1 | 108.9 |
C7—C8—C4 | 104.84 (14) | O10—C6'—H6'2 | 108.9 |
C1—C8—H8 | 107.5 | C5'—C6'—H6'2 | 108.9 |
C7—C8—H8 | 107.5 | H6'1—C6'—H6'2 | 107.8 |
C4—C8—H8 | 107.5 | C2—O1—C1 | 113.02 (13) |
C7—C9—H9A | 109.5 | C1'—O2—C2 | 116.50 (13) |
C7—C9—H9B | 109.5 | C10—O3—C11 | 116.57 (15) |
H9A—C9—H9B | 109.5 | C1'—O6—C5' | 112.17 (13) |
C7—C9—H9C | 109.5 | C2'—O7—H7A | 109.5 |
H9A—C9—H9C | 109.5 | C3'—O8—H8A | 109.5 |
H9B—C9—H9C | 109.5 | C4'—O9—H9 | 109.5 |
O4—C10—O3 | 124.28 (16) | C6'—O10—H10 | 109.5 |
| | | |
O1—C2—C3—C10 | 178.17 (14) | O6—C1'—C2'—O7 | 175.60 (13) |
O2—C2—C3—C10 | 54.28 (17) | O2—C1'—C2'—C3' | 173.23 (13) |
O1—C2—C3—C4 | 54.28 (18) | O6—C1'—C2'—C3' | 55.72 (18) |
O2—C2—C3—C4 | −69.61 (17) | O7—C2'—C3'—O8 | 65.07 (18) |
C10—C3—C4—C5 | 80.83 (17) | C1'—C2'—C3'—O8 | −175.15 (14) |
C2—C3—C4—C5 | −156.80 (14) | O7—C2'—C3'—C4' | −172.86 (14) |
C10—C3—C4—C8 | −165.73 (14) | C1'—C2'—C3'—C4' | −53.08 (19) |
C2—C3—C4—C8 | −43.36 (18) | O8—C3'—C4'—O9 | −58.92 (19) |
C3—C4—C5—O5 | −67.2 (2) | C2'—C3'—C4'—O9 | −179.96 (14) |
C8—C4—C5—O5 | 173.73 (17) | O8—C3'—C4'—C5' | 175.88 (14) |
C3—C4—C5—C6 | 110.14 (16) | C2'—C3'—C4'—C5' | 54.84 (18) |
C8—C4—C5—C6 | −8.97 (18) | O9—C4'—C5'—O6 | 177.08 (13) |
O5—C5—C6—C7 | 162.52 (17) | C3'—C4'—C5'—O6 | −58.46 (18) |
C4—C5—C6—C7 | −14.77 (19) | O9—C4'—C5'—C6' | 60.21 (19) |
C5—C6—C7—C9 | 155.70 (15) | C3'—C4'—C5'—C6' | −175.32 (14) |
C5—C6—C7—C8 | 32.36 (18) | O6—C5'—C6'—O10 | 68.25 (18) |
O1—C1—C8—C7 | 74.23 (19) | C4'—C5'—C6'—O10 | −172.88 (14) |
O1—C1—C8—C4 | −47.0 (2) | O2—C2—O1—C1 | 57.51 (18) |
C9—C7—C8—C1 | 72.9 (2) | C3—C2—O1—C1 | −62.12 (17) |
C6—C7—C8—C1 | −163.99 (14) | C8—C1—O1—C2 | 58.58 (18) |
C9—C7—C8—C4 | −161.40 (14) | O6—C1'—O2—C2 | −95.05 (16) |
C6—C7—C8—C4 | −38.27 (17) | C2'—C1'—O2—C2 | 145.50 (14) |
C5—C4—C8—C1 | 156.25 (15) | O1—C2—O2—C1' | 73.21 (18) |
C3—C4—C8—C1 | 40.65 (19) | C3—C2—O2—C1' | −163.92 (14) |
C5—C4—C8—C7 | 29.20 (17) | O4—C10—O3—C11 | 4.2 (2) |
C3—C4—C8—C7 | −86.40 (16) | C3—C10—O3—C11 | −174.33 (14) |
C2—C3—C10—O4 | −109.65 (19) | O2—C1'—O6—C5' | −178.19 (13) |
C4—C3—C10—O4 | 14.3 (2) | C2'—C1'—O6—C5' | −61.05 (17) |
C2—C3—C10—O3 | 68.81 (17) | C6'—C5'—O6—C1' | −177.66 (14) |
C4—C3—C10—O3 | −167.28 (13) | C4'—C5'—O6—C1' | 62.43 (18) |
O2—C1'—C2'—O7 | −66.90 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O10—H10···O4i | 0.82 | 2.17 | 2.7588 (19) | 128 |
O9—H9···O7ii | 0.82 | 1.89 | 2.7091 (19) | 173 |
O8—H8A···O9 | 0.82 | 2.44 | 2.8635 (19) | 113 |
O8—H8A···O5iii | 0.82 | 2.28 | 2.9571 (19) | 141 |
O7—H7A···O10iv | 0.82 | 1.83 | 2.638 (2) | 171 |
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, −z+1; (iii) −x+1, y−1/2, −z+1/2; (iv) x−1, y, z. |
1H and 13C NMR data for compound (1) in pyridine-d6
[δ in ppm (J in Hz)] topPosition | δ(H) | δ(C) | COSY | HMBC | NOESY |
1 | 3.64 dd (12.6, 1.8); | 56.9 | H-7a | H-1/C-3,4a,7,7a | |
| 4.57 dd (12.6, 4.2) | | | | |
3 | 5.82 d (3.6) | 97.4 | H-4 | H-3/C-1,4,4a,9,1' | H-4, H-1' |
4 | 3.09 dd (11.4, 4.2) | 42.3 | H-4a,3 | H-4/C-3,4a,5,9 | H-3, H-7 |
4a | 3.54 dd (11.4, 7.8) | 42.5 | H-7a,4 | H-4a/C-3,4,5,6,7,7a,9 | H-7a |
5 | | 216.4 | | | |
6 | 1.85 ddd (18.6, 10.8, 1.2); | 46.0 | H-7 | H-6/C-4a,5,7,7a,8 | |
| 2.49 dd (18.6, 7.8) | | | | |
7 | 2.26 m | 30.2 | H-6,7a,8 | H-7/C-1,6,7a,8 | H-4 |
7a | 1.68 m | 41.3 | H-1,4a,7 | H-7a/C-4,4a,7,8 | H-4a, H-8 |
8 | 0.87 d (6.6) | 18.0 | H-7 | H-8/C-6,7,7a | H-7a |
9 | | 169.9 | | | |
OCH3 | 3.76 s | 51.8 | | C-9 | |
1' | 5.07 d (7.8) | 103.8 | H-2' | H-1'/C-3,2',5' | H-3', H-5', H-3 |
2' | 3.94 t (9.0) | 75.1 | H-1',3' | H-2'/C-3',4' | |
3' | 4.13 t (9.0) | 78.6 | H-2',4' | H-3'/C-1',5' | H-1', H-5' |
4' | 4.21 t (9.0) | 70.9 | H-3',5' | H-4'/C-2',6' | |
5' | 3.89 m | 78.7 | H-4',6' | H-5'/C-4',6' | H-1', H-3' |
6' | 4.37 dd (12.0, 4.8); | 62.4 | H-5' | H-6'/C-4',5' | |
| 4.48 dd (12.0, 2.4) | | | | |
Cytotoxic activity of (1) presented as IC50 (µM). topCompound | IC50 | | | |
Hela | A549 | THP-1 | HepG2 | |
(1) | 5.5±0.48 | 10.2±0.97 | >50 | >50 |
Doxorubicin | 1.34±0.06 | 0.88±0.09 | 0.51±0.02 | 1.01±0.14 |