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