Bioinspired computational design of lankacidin derivatives for improvement in antitumor activity - supplement information
Table S1. 1H- and 13C-NMR data of lankacidin C (1), 7-O-acetyl-lankacidin C (2), 13-Oacetyl-
lankacidin C (3), and 7,13-di-O-acetyl-lankacidin C (4)
Table S2. 1H- and 13C-NMR data of lankacidin C (1), 7-O-cinnamoyl-lankacidin C (5), 13-
O-cinnamoyl-lankacidin C (6), 7,13-di-O-cinnamoyl-lankacidin C (7), 7-Ohydrocinnamoyl-
lankacidin C (8), 13-O-hydrocinnamoyl-lankacidin C (9), and
7,13-di-O-hydrocinnamoyl-lankacidin C (10)
Figure S1. 1H-NMR spectrum of lankacidin C (1)
Figure S2. 13C-NMR spectrum of lankacidin C (1)
Figure S3. DEPT spectrum of lankacidin C (1)
Figure S4. DQF-COSY spectrum of lankacidin C (1)
Figure S5. HMQC spectrum of lankacidin C (1)
Figure S6. HMBC spectrum of lankacidin C (1)
Figure S7. 1H-NMR spectrum of 7-O-Ac-lankacidin C (2)
Figure S8. 13C-NMR spectrum of 7-O-Ac-lankacidin C (2)
Figure S9. DEPT spectrum of 7-O-Ac-lankacidin C (2)
Figure S10. DQF-COSY spectrum of 7-O-Ac-lankacidin C (2)
Figure S11. HMQC spectrum of 7-O-Ac-lankacidin C (2)
Figure S12. HMBC spectrum of 7-O-Ac-lankacidin C (2)
Figure S13. 1H-NMR spectrum of 13-O-Ac-lankacidin C (3)
Figure S14. 13C-NMR spectrum of 13-O-Ac-lankacidin C (3)
Figure S15. DEPT spectrum of 13-O-Ac-lankacidin C (3)
Figure S16. DQF-COSY spectrum of 13-O-Ac-lankacidin C (3)
Figure S17. HMQC spectrum of 13-O-Ac-lankacidin C (3)
Figure S18. HMBC spectrum of 13-O-Ac-lankacidin C (3)
Figure S19. 1H-NMR spectrum of 7,13-di-O-Ac-lankacidin C (4)
Figure S20. 13C-NMR spectrum of 7,13-di-O-Ac-lankacidin C (4)
Figure S21. DEPT spectrum of 7,13-di-O-Ac-lankacidin C (4)
Figure S22. DQF-COSY spectrum of 7,13-di-O-Ac-lankacidin C (4)
Figure S23. HMQC spectrum of 7,13-di-O-Ac-lankacidin C (4)
Figure S24. HMBC spectrum of 7,13-di-O-Ac-lankacidin C (4)
Figure S25. 1H-NMR spectrum of 7-O-cinnamoyl-lankacidin C (5)
Figure S26. 13C-NMR spectrum of 7-O-cinnamoyl-lankacidin C (5)
Figure S27. DEPT spectrum of 7-O-cinnamoyl-lankacidin C (5)
Figure S28. DQF-COSY spectrum of 7-O-cinnamoyl-lankacidin C (5)
Figure S29. HMQC spectrum of 7-O-cinnamoyl-lankacidin C (5)
Figure S30. HMBC spectrum of 7-O-cinnamoyl-lankacidin C (5)
Figure S31. 1H-NMR spectrum of 13-O-cinnamoyl-lankacidin C (6)
Figure S32. 13C-NMR spectrum of 13-O-cinnamoyl-lankacidin C (6)
Figure S33. DEPT spectrum of 13-O-cinnamoyl-lankacidin C (6)
Figure S34. DQF-COSY spectrum of 13-O-cinnamoyl-lankacidin C (6)
Figure S35. HMQC spectrum of 13-O-cinnamoyl-lankacidin C (6)
Figure S36. HMBC spectrum of 13-O-cinnamoyl-lankacidin C (6)
Figure S37. 1H-NMR spectrum of 7,13-di-O-cinnamoyl-lankacidin C (7)
Figure S38. 13C-NMR spectrum of 7,13-di-O-cinnamoyl-lankacidin C (7)
Figure S39. DEPT spectrum of 7,13-di-O-cinnamoyl-lankacidin C (7)
Figure S40. DQF-COSY spectrum of 7,13-di-O-cinnamoyl-lankacidin C (7)
Figure S41. HMQC spectrum of 7,13-di-O-cinnamoyl-lankacidin C (7)
Figure S42. HMBC spectrum of 7,13-di-O-cinnamoyl-lankacidin C (7)
Figure S43. 1H-NMR spectrum of 7-O-hydrocinnamoyl-lankacidin C (8)
Figure S44. 13C-NMR spectrum of 7-O-hydrocinnamoyl-lankacidin C (8)
Figure S45. DEPT spectrum of 7-O-hydrocinnamoyl-lankacidin C (8)
Figure S46. DQF-COSY spectrum of 7-O-hydrocinnamoyl-lankacidin C (8)
Figure S47. HMQC spectrum of 7-O-hydrocinnamoyl-lankacidin C (8)
Figure S48. HMBC spectrum of 7-O-hydrocinnamoyl-lankacidin C (8)
Figure S49. 1H-NMR spectrum of 13-O-hydrocinnamoyl-lankacidin C (9)
Figure S50. 13C-NMR spectrum of 13-O-hydrocinnamoyl-lankacidin C (9)
Figure S51. DEPT spectrum of 13-O-hydrocinnamoyl-lankacidin C (9)
Figure S52. DQF-COSY spectrum of 13-O-hydrocinnamoyl-lankacidin C (9)
Figure S53. HMQC spectrum of 13-O-hydrocinnamoyl-lankacidin C (9)
Figure S54. HMBC spectrum of 13-O-hydrocinnamoyl-lankacidin C (9)
Figure S55. 1H-NMR spectrum of 7,13-di-O-hydrocinnamoyl-lankacidin C (10)
Figure S56. 13C-NMR spectrum of 7,13-di-O-hydrocinnamoyl-lankacidin C (10)
Figure S57. DEPT spectrum of 7,13-di-O-hydrocinnamoyl-lankacidin C (10)
Figure S58. DQF-COSY spectrum of 7,13-di-O-hydrocinnamoyl-lankacidin C (10)
Figure S59. HMQC spectrum of 7,13-di-O-hydrocinnamoyl-lankacidin C (10)
Figure S60. HMBC spectrum of 7,13-di-O-hydrocinnamoyl-lankacidin C (10)
Figure S61. HPLC chromatogram of compounds 1–10
Figure S62. TLC analysis of compounds 1–10
Figure S63. The 2D-interaction between the 10 different ligands to the paclitaxel-binding
site
Figure S64. Dose-response curves and IC50 values for compounds 1-10 and positive controls,
5-fluorouracil and paclitaxel, in three human cancer cells, HeLa, MCF-7, and A549 cells
