SUPPLEMENTARY MATERIAL
Isolation, characterization and antiproliferative activity of
bi- and bisbibenzyls from the roots of Dichapetalum heudelotii
Dorcas Osei-Safo a, *, Godwin Akpeko Dziwornu a, b, Antonio
Salgado Serrano c, Suthananda Naidu
Sunassee b, d, Mary Anti Chama a
a Chemistry Department, School of Physical and Mathematical
Sciences, College of Basic and Applied Sciences, University of
Ghana, P. O. Box LG 56, Legon, Accra, Ghana
[email protected]; [email protected];
[email protected]
b Department of Chemistry, University of Cape Town, Rondebosch,
7701, South Africa
c Centro de Espectroscopía de RMN (CERMN), CAI Químicas,,
University of Alcalá Henares, E-28805 Alcalá de Henares, Madrid,
Spain
[email protected]
dSouth African Medical Research Council Drug Discovery and
Development Research Unit, University of Cape Town, Rondebosch
7701, South Africa
[email protected]
* Correspondence: [email protected]; [email protected];
Tel.: +233-208-169376
Table of Contents:
Figure S1. HR-ESI-MS of heudelotol A (1)
Figure S2. HPLC-UV spectra of heudelotol A (1)
Figure S3. 1H-NMR spectrum (600MHz, CDCl3, 303K) of heudelotol A
(1)
Figure S4. 13C-NMR spectrum (150MHz, CDCl3, 303K) of heudelotol
A (1)
Figure S5. COSY NMR spectrum (600MHz, CDCl3, 303K) of heudelotol
A (1)
Figure S6. HSQC-DEPT NMR spectrum (600MHz, CDCl3, 303K) of
heudelotol A (1)
Figure S7. HMBC NMR spectrum (600MHz, CDCl3, 303K) of heudelotol
A (1)
Figure S8. HR-ESI-MS of heudelotol B (2)
Figure S9. HPLC-UV spectra of heudelotol B (2)
Figure S10. 1H-NMR spectrum (600MHz, CDCl3, 303K) of heudelotol
B (2)
Figure S11. 13C-NMR spectrum (150MHz, CDCl3, 303K) of heudelotol
B (2)
Figure S12. COSY NMR spectrum (600MHz, CDCl3, 303K) of
heudelotol B (2)
Figure S13. HSQC-DEPT NMR spectrum (600MHz, CDCl3, 303K) of
heudelotol B (2)
Figure S14. HMBC NMR spectrum (600MHz, CDCl3, 303K) of
heudelotol B (2)
Figure S15. NOESY NMR spectrum (600MHz, CDCl3, 303K) of
heudelotol B (2)
Figure S16. HR-ESI-MS of (E)-combretastatin A-1 (3)
Figure S17. HPLC-UV spectra of (E)-combretastatin A-1 (3)
Figure S18. HR-ESI-MS of combretastatin B-1 (4)
Figure S19. HPLC-UV spectra of combretastatin B-1 (4)
Table S1. Antiproliferative activities of compounds 1 – 4 and
taxol
C36H46NO12+: Calc. 684.3015; Obs. 684.3023; Err. 1.2ppm
Figure S1. HR-ESI-MS of heudelotol A (1)
Max: 234 nm (sh), 271 nm
Figure S2. HPLC-UV spectra of heudelotol A (1)
Figure S3. 1H-NMR spectrum (600MHz, CDCl3, 303K) of heudelotol A
(1)
Figure S4. 13C-NMR spectrum (150MHz, CDCl3, 303K) of heudelotol
A (1)
Figure S5. COSY NMR spectrum (600MHz, CDCl3, 303K) of heudelotol
A (1)
Figure S6. HSQC-DEPT NMR spectrum (600MHz, CDCl3, 303K) of
heudelotol A (1)
Figure S7. HMBC NMR spectrum (600MHz, CDCl3, 303K) of heudelotol
A (1)
C36H41O12+: Calc. 665.2593; Obs. 665.2597; Err. 0.6ppm
Figure S8. HR-ESI-MS of heudelotol B (2)
Max: 236 nm (sh), 272 nm
Figure S9. HPLC-UV spectra of heudelotol B (2)
Figure S10. 1H-NMR spectrum (600MHz, CDCl3, 303K) of heudelotol
B (2)
Figure S11. 13C-NMR spectrum (150MHz, CDCl3, 303K) of heudelotol
B (2)
Figure S12. COSY NMR spectrum (600MHz, CDCl3, 303K) of
heudelotol B (2)
Figure S13. HSQC-DEPT NMR spectrum (600MHz, CDCl3, 303K) of
heudelotol B (2)
Figure S14. HMBC NMR spectrum (600MHz, CDCl3, 303K) of
heudelotol B (2)
Figure S15. NOESY NMR spectrum (600MHz, CDCl3, 303K) of
heudelotol B (2)
C18H21O6+: Calc. 333.1333; Obs. 333.1341; Err. 2.4ppm
Figure S16. HR-ESI-MS of (E)-combretastatin A-1 (3)
Max. 228 nm (sh), 297 nm
Figure S17. HPLC-UV spectra of (E)-combretastatin A-1 (3)
C18H23O6+: Calc. 335.1489; Obs. 335.1497; Err. 2.4ppm
Figure S18. HR-ESI-MS of combretastatin B-1 (4)
Max. 235 nm (sh), 268 nm
Figure S19. HPLC-UV spectra of combretastatin B-1 (4)
Table S1: Antiproliferative activity (GI50/µM ± SEM) of
compounds 1 – 4 and taxol
Compound
HCT116
MDA-MB-231
A549
Du145
BxPC3
Namalwa
Heudelotol A (1)
12.05 ± 0.45
11.15 ± 0.55
12.8 ± 0.30
27.9 ± 0.30
8.87 ± 1.10
9.04 ± 0.85
Heudelotol B (2)
6.17 ± 0.04
18.95 ± 1.55
38.3 ± 5.80
51.8 ± 7.10
11.5 ± 1.12
4.67 ± 0.11
(E)-combretastatin A-1 (3)
0.06
0.19 ± 0.07
0.19 ± 0.07
0.11 ± 0.01
0.72 ± 0.23
0.03
Combretastatin B-1 (4)
0.25 ± 0.01
1.11 ± 0.06
1.43 ± 0.13
0.72 ± 0.02
3.88 ± 0.81
0.05 ± 0.01
Taxol
0.0041 ± 0.0001
0.0096 ± 0.0002
0.0062 ± 0.0004
0.0056 ± 0.0003
0.0042 ± 0.0005
0.0022 ± 0.0001
OMe
OH
HO
OMe
MeO
OMe
HO
HO
OMe
OMe
OMe
1
8''
3''
1''
4'
8
5
3
4'''
1'''1'7''7
MeO
Heudelotol A
665.2597
682.2868
+MS, 4.29min #254
0.0
0.2
0.4
0.6
0.8
1.0
6
x10
Intens.
630640650660670680690700710720m/z
665.2597
682.2868
+MS, 4.29min #254
0.0
0.2
0.4
0.6
0.8
1.0
6
x10
Intens.
630640650660670680690700710720m/z
UV, 4.29min #1222,
0
200
400
600
800
1000
Intens.
[mAU]
200300400Wavelength [nm]
OMe
MeO
OH
OH
OMe
OMe
OMe
OH
HO
OMe
MeO
MeO
7
1
1''
4'
1'
8
3
7''
4''
4'''
1'''
8''
5
Heudelotol B
335.1497
352.1759
+MS, 3.65min #216
0.00
0.25
0.50
0.75
1.00
1.25
6
x10
Intens.
300310320330340350360370380390400m/z
335.1497
352.1759
+MS, 3.65min #216
0.00
0.25
0.50
0.75
1.00
1.25
6
x10
Intens.
300310320330340350360370380390400m/z
