Structural Investigation of Biologically Active Phenolic Compounds Isolated from European Tree Species
Abstract
:Introduction
Results and Discussion
Compound | 1a | 1b | 2 | ||||
---|---|---|---|---|---|---|---|
Molecular formula | C15H12O6*CH3CH2OH | C15H12O6*CH3OH | C20H24O6 | ||||
Formula weight | 334.31 | 320.29 | 360.39 | ||||
CCDC No. | 719360 | 719361 | 719362 | ||||
Crystallographic system | triclinic | triclinic | monoclinic | ||||
Space group | P1 | P1 | P21 | ||||
a [Å] | 7.617(5) | 7.581(2) | 10.718(6) | ||||
b [Å] | 10.349(3) | 10.275(2) | 5.656(3) | ||||
c [Å] | 11.488(3) | 11.120(2) | 14.264(8) | ||||
α [o] | 63.92(2) | 65.28(3) | |||||
β [o] | 85.36(4) | 81.80(3) | 92.75(5) | ||||
γ [o] | 79.18(3) | 76.61(3) | |||||
V [Å3] | 798.9(6) | 764.4(3) | 863.7(8) | ||||
Z | 2 | 2 | 2 | ||||
Dc [g/cm3] | 1.390 | 1.392 | 1.386 | ||||
μ [mm-1] | 0.918 | 0.936 | 0.102 | ||||
Crystal dimensions [mm] | 0.60x0.40x0.02 | 0.56x0.12x0.1 | 1.00x0.06x0.02 | ||||
Radiation, λ (Å) | CuKα, 1.54178 | CuKα, 1.54178 | synchrotron, 0.80420 | ||||
hkl ranges: | h = | -9 | 0 | 0 | 9 | -14 | 14 |
k = | -12 | 12 | -12 | 12 | -6 | 6 | |
l = | -14 | 14 | -13 | 13 | -19 | 19 | |
EAC correction: | min. | 0.8867 | 0.9392 | NA | |||
max. | 0.9933 | 0.9980 | |||||
ave. | 0.9294 | 0.9679 | |||||
No. of reflections: | unique | 3545 | 3396 | 4342 | |||
with I>0σ(I) | 3353 | 3210 | 3372 | ||||
obs. with I>2σ(I) | 2982 | 2982 | 4007 | ||||
No. of parameters refined | 472 | 454 | 332 | ||||
Robs | 0.0691 | 0.0430 | 0.0431 | ||||
wRobs | 0.1871 | 0.1376 | 0.1137 | ||||
Rint | 0.0000 | 0.0000 | 0.0000 | ||||
Sobs | 1.098 | 1.094 | 1.051 |
1b | |||||
molecule | 1 | 1’ | molecule | 1 | 1’ |
ΔCsC6=ΔCsC9 | 12.2(8) | 12.4(8) | ΔC2C1-C6=ΔC2C8-C9 | 13.3(9) | 16.6(9) |
2 | |||||
ΔCsC8 | 11.2(3) | ΔC2C8-C9 | 4.6(3) | ||
ΔCsC9 | 17.8(3) | ΔC2C9-C10 | 40.2(3) |
1b | ||||||||||||
molecule | 1 | 1’ | molecule | 1 | 1’ | |||||||
C1 | C2 | C3 | O2 | -177.3(3) | -179.2(4) | C1 | O1 | C9 | C10 | 172.7(3) | -179.7(3) | |
O2 | C3 | C4 | C5 | 176.5(3) | -179.7(4) | O5 | C8 | C9 | C10 | 60.4(4) | 54.0(4) | |
C3 | C4 | C5 | O3 | -178.7(3) | 179.1(3) | C7 | C8 | C9 | C10 | -176.4(3) | 176.8(3) | |
O3 | C5 | C6 | C1 | 180.0(3) | -178.8(3) | O1 | C9 | C10 | C15 | -65.8(4) | -66.5(4) | |
O3 | C5 | C6 | C7 | 2.9(5) | 4.4(5) | C8 | C9 | C10 | C15 | 52.8(5) | 53.1(5) | |
C6 | C7 | C8 | O5 | 160.4(3) | 161.4(3) | O1 | C9 | C10 | C11 | 118.9(4) | 114.5(4) | |
C5 | C6 | C7 | O4 | -7.3(6) | -7.6(6) | C8 | C9 | C10 | C11 | -122.4(4) | -125.9(4) | |
O4 | C7 | C8 | O5 | -22.5(5) | -20.0(5) | O6 | C13 | C14 | C15 | 179.4(5) | -179.5(4) | |
O4 | C7 | C8 | C9 | -144.9(3) | -142.1(3) | |||||||
2 | ||||||||||||
C18 | O2 | C3 | C2 | 0.4(2) | O1 | C7 | C8 | C19 | -88.0(1) | |||
C18 | O2 | C3 | C4 | 179.8(1) | C1 | C7 | C8 | C19 | 149.7(1) | |||
O2 | C3 | C4 | O3 | -0.1(2) | O1 | C7 | C8 | C9 | 33.6(1) | |||
C2 | C3 | C4 | O3 | 179.3(1) | C19 | C8 | C9 | C11 | -43.2(2) | |||
O2 | C3 | C4 | C5 | 180.0(1) | C9 | C11 | C12 | C17 | 84.7(2) | |||
O3 | C4 | C5 | C6 | -178.6(1) | C9 | C11 | C12 | C13 | -92.5(2) | |||
C10 | O1 | C7 | C1 | 107.9(1) | C20 | O4 | C14 | C13 | -0.2(2) | |||
C10 | O1 | C7 | C8 | -15.4(1) | C20 | O4 | C14 | C15 | 177.7(1) | |||
C6 | C1 | C7 | O1 | -19.2(2) | C12 | C13 | C14 | O4 | -179.6(1) | |||
C2 | C1 | C7 | O1 | 162.0(1) | O4 | C14 | C15 | O5 | -1.1(2) | |||
C6 | C1 | C7 | C8 | 99.3(2) | C7 | C8 | C19 | O6 | -67.7(2) | |||
C2 | C1 | C7 | C8 | -79.4(2) |
1b | 2 | |||
---|---|---|---|---|
Plane 1 C1, C2, C3, C4, C5, C6 | Plane 1 C1, C2, C3, C4, C5, C6 | |||
Plane 2 C10, C11, C12, C13, C14, C15 | Plane 2 C12, C13, C14, C15, C16, C17 | |||
Plane 3 C7, C8, C9 | Plane 3 O1, C7, C9, C10 | |||
Plane 4 O1, C8, C9 | Plane 4 C7, C8, C9 | |||
Plane 5 O1, C1, C6, C7 | Plane 5 O1, C7, C10 | |||
molecule | 1 | 1’ | ||
1 / 2 | 85.76(14) | 87.22(16) | 1 / 2 | 38.61(4) |
1 / 3 | 38.63(38) | 40.55(22) | 1 / 3 | 86.53(5) |
2 / 3 | 56.54(36) | 52.61(25) | 2 / 3 | 55.71(5) |
1 / 4 | 44.27(39) | 50.10(21) | 1 / 4 | 68.13(7) |
2 / 4 | 88.23(19) | 89.68(23) | 2 / 4 | 75.63(8) |
3 / 4 | 58.58(42) | 63.41(28) | 3 / 4 | 36.70(10) |
1 / 5 | 3.06(20) | 3.02(18) | 1 / 5 | 80.48(8) |
2 / 5 | 88.57(20) | 89.78(17) | 2 / 5 | 61.55(8) |
3 / 5 | 35.64(42) | 37.53(28) | 3 / 5 | 6.16(9) |
4 / 5 | 45.21(38) | 50.32(20) | 4 / 5 | 32.72(12) |
D―H···A | D―H | H···A | D···A | D―H···A |
1a | ||||
O3―H3O···O4 | 0.820(27) | 1.926(30) | 2.646(5) | 146.0(36) |
O5―H5O···O4 | 0.820(26) | 2.265(28) | 2.698(5) | 113.4(28) |
O3'―H3'O···O4' | 0.820(14) | 1.955(34) | 2.656(5) | 143.0(35) |
O5'―H5'O···O4' | 0.820(23) | 2.231(20) | 2.701(4) | 116.7(23) |
O5―H5O···O4' i | 0.820(26) | 2.068(33) | 2.767(5) | 142.9(31) |
O6―H6O···O5' ii | 0.820(36) | 1.895(39) | 2.698(6) | 165.7(45) |
O5'―H5'O···O4 iii | 0.820(23) | 2.088(20) | 2.751(4) | 137.7(25) |
O6'―H6'O···O5 iv | 0.820(43) | 1.929(44) | 2.663(7) | 148.7(40) |
O2―H2O···O7 v | 0.820(42) | 1.814(46) | 2.616(6) | 165.6(59) |
O7―H7O···O6vi | 0.820(18) | 2.005(32) | 2.796(7) | 161.8(63) |
O2'―H2'O···O7' vii | 0.820(19) | 1.934(56) | 2.630(6) | 142.1(42) |
O7'―H7'O···O6' viii | 0.820(16) | 2.008(22) | 2.817(7) | 168.7(38) |
C8―H8···O2 vii | 0.980(8) | 2.406(6) | 3.133(7) | 130.5(5) |
1b | ||||
O3―H3O···O4 | 0.820(18) | 1.925(22) | 2.646(4) | 146.3(28) |
O5―H5O···O4 | 0.820(23) | 2.303(27) | 2.689(4) | 109.4(28) |
O3'―H3'O···O4' | 0.820(14) | 1.945(23) | 2.665(4) | 146.0(28) |
O5'―H5'O···O4' | 0.820(21) | 2.257(23) | 2.698(3) | 114.1(23) |
O5―H5O···O4' i | 0.820(23) | 2.104(35) | 2.773(4) | 138.5(32) |
O6―H6O···O5' ii | 0.820(25) | 1.871(26) | 2.676(4) | 166.5(30) |
O5'―H5'O···O4 iii | 0.820(21) | 2.066(13) | 2.762(3) | 142.5(26) |
O6'―H6'O···O5 iv | 0.820(52) | 1.893(52) | 2.651(5) | 153.2(51) |
O2―H2O···O7 v | 0.820(18) | 1.815(19) | 2.627(4) | 169.9(20) |
O7―H7O···O6 vi | 0.820(38) | 1.979(33) | 2.769(5) | 161.4(43) |
O2'―H2'O···O7' vii | 0.820(49) | 1.809(49) | 2.626(5) | 174.3(57) |
O7'―H7'O···O6' viii | 0.820(18) | 1.995(19) | 2.789(6) | 162.6(33) |
C8―H8···O2 vii | 0.980(6) | 2.441(5) | 3.124(5) | 126.5(4) |
2 | ||||
O3―H3O···O2 | 0.889(30) | 2.128(30) | 2.652(2) | 117.0(24) |
O5―H5O···O4 | 0.874(35) | 2.187(27) | 2.660(2) | 113.6(26) |
O6―H6O···O1ix | 0.975(31) | 1.848(30) | 2.787(2) | 160.8(27) |
O5―H5O···O6 i | 0.874(35) | 2.312(28) | 2.880(2) | 122.7(27) |
C2―H2···O5 iii | 1.075(24) | 2.386(24) | 3.454(2) | 172.3(18) |
C13―H13···O6 x | 1.018(23) | 2.546(24) | 3.452(2) | 148.1(19) |
C20―H201···O4 xi | 0.965(30) | 2.544(28) | 3.464(3) | 159.5(22) |
Experimental
General
Conclusions
- Sample Availability: Samples of the compounds are available from the authors.
References
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Redzynia, I.; Ziółkowska, N.E.; Majzner, W.R.; Willför, S.; Sjöholm, R.; Eklund, P.; Bujacz, G.D. Structural Investigation of Biologically Active Phenolic Compounds Isolated from European Tree Species. Molecules 2009, 14, 4147-4158. https://doi.org/10.3390/molecules14104147
Redzynia I, Ziółkowska NE, Majzner WR, Willför S, Sjöholm R, Eklund P, Bujacz GD. Structural Investigation of Biologically Active Phenolic Compounds Isolated from European Tree Species. Molecules. 2009; 14(10):4147-4158. https://doi.org/10.3390/molecules14104147
Chicago/Turabian StyleRedzynia, Izabela, Natasza E. Ziółkowska, Wiesław R. Majzner, Stefan Willför, Rainer Sjöholm, Patrik Eklund, and Grzegorz D. Bujacz. 2009. "Structural Investigation of Biologically Active Phenolic Compounds Isolated from European Tree Species" Molecules 14, no. 10: 4147-4158. https://doi.org/10.3390/molecules14104147