Bioactive Pentacyclic Triterpenoids from the Leaves of Cleistocalyx operculatus
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1 Bioactive Pentacyclic Triterpenoids from the Leaves of Cleistocalyx operculatus Chen Wang,, Ping Wu, Shuai Tian, Jinghua Xue, Liangxiong Xu, anxiang Li, and Xiaoyi Wei *, Key Laboratory of Plant Resources Conservation and Sustainable Utilization and Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou , People's Republic of China University of Chinese Academy of Sciences, Yuquanlu 19A, Beijing , People's Republic of China *Corresponding author: Tel: Fax:
2 Supporting Information Table of Contents 1. Key 2D NMR Correlations of 2, 5, 8, 9, 11 13, and Figure S1. Key 1-1 COSY and MBC correlations of 2, 5, 8, 9, 11 13, and Figure S2. Key NOE correlations of Method for ECD/TDDFT Computations. 7 Figure S3. Truncated structures used in theoretical calculations Figure S4. Low energy conformers of truncated structures NMR Spectra and RESIMS Figure S5. 1 NMR spectrum of 1 in pyridine-d Figure S6. 13 C NMR spectrum of 1 in pyridine-d Figure S7. SQC spectrum of 1 in pyridine-d Figure S COSY spectrum of 1 in pyridine-d Figure S9. MBC spectrum of 1 in pyridine-d Figure S10. NOESY spectrum of 1 in pyridine-d Figure S11. R-ESIMS of Figure S12. 1 NMR spectrum of 2 in pyridine-d Figure S C NMR spectrum of 2 in pyridine-d Figure S14. SQC spectrum of 2 in pyridine-d Figure S COSY spectrum of 2 in pyridine-d Figure S16. MBC spectrum of 2 in pyridine-d Figure S17. NOESY spectrum of 2 in pyridine-d Figure S18. R-ESIMS of Figure S19. 1 NMR spectrum of 3 in pyridine-d Figure S C NMR spectrum of 3 in pyridine-d Figure S21. SQC spectrum of 3 in pyridine-d Figure S COSY spectrum of 3 in pyridine-d Figure S23. MBC spectrum of 3 in pyridine-d
3 Figure S24. NOESY spectrum of 3 in pyridine-d Figure S25. R-ESIMS of Figure S26. 1 NMR spectrum of 4 in pyridine-d Figure S C NMR spectrum of 4 in pyridine-d Figure S28. SQC spectrum of 4 in pyridine-d Figure S COSY spectrum of 4 in pyridine-d Figure S30. MBC spectrum of 4 in pyridine-d Figure S31. NOESY spectrum of 4 in pyridine-d Figure S32. R-ESIMS of Figure S33. 1 NMR spectrum of 5 in pyridine-d Figure S C NMR spectrum of 5 in pyridine-d Figure S35. SQC spectrum of 5 in pyridine-d Figure S COSY spectrum of 5 in pyridine-d Figure S37. MBC spectrum of 5 in pyridine-d Figure S38. NOESY spectrum of 5 in pyridine-d Figure S39. R-ESIMS of Figure S40. 1 NMR spectrum of 6 in methanol-d Figure S C NMR spectrum of 6 in methanol-d Figure S42. SQC spectrum of 6 in methanol-d Figure S COSY spectrum of 6 in methanol-d Figure S44. MBC spectrum of 6 in methanol-d Figure S45. NOESY spectrum of 6 in methanol-d Figure S46. R-ESIMS of Figure S47. 1 NMR spectrum of 7 in methanol-d Figure S C NMR spectrum of 7 in methanol-d Figure S49. SQC spectrum of 7 in methanol-d Figure S COSY spectrum of 7 in methanol-d Figure S51. MBC spectrum of 7 in methanol-d Figure S52. NOESY spectrum of 7 in methanol-d Figure S53. R-ESIMS of
4 Figure S54. 1 NMR spectrum of 8 in methanol-d Figure S C NMR spectrum of 8 in methanol-d Figure S56. SQC spectrum of 8 in methanol-d Figure S COSY spectrum of 8 in methanol-d Figure S58. MBC spectrum of 8 in methanol-d Figure S59. R-ESIMS of Figure S60. 1 NMR spectrum of 9 in methanol-d Figure S C NMR spectrum of 9 in methanol-d Figure S62. SQC spectrum of 9 in methanol-d Figure S COSY spectrum of 9 in methanol-d Figure S64. MBC spectrum of 9 in methanol-d Figure S65. R-ESIMS of Figure S66. 1 NMR spectrum of 10 in pyridine-d Figure S C NMR spectrum of 10 in pyridine-d Figure S68. SQC spectrum of 10 in pyridine-d Figure S COSY spectrum of 10 in pyridine-d Figure S70. MBC spectrum of 10 in pyridine-d Figure S71. NOESY spectrum of 10 in pyridine-d Figure S72. R-ESIMS of Figure S73. 1 NMR spectrum of 11 in methanol-d Figure S C NMR spectrum of 11 in methanol-d Figure S75. SQC spectrum of 11 in methanol-d Figure S COSY spectrum of 11 in methanol-d Figure S77. MBC spectrum of 11 in methanol-d Figure S78. R-ESIMS of Figure S79. 1 NMR spectrum of 12 in methanol-d Figure S C NMR spectrum of 12 in methanol-d Figure S81. SQC spectrum of 12 in methanol-d Figure S COSY spectrum of 12 in methanol-d Figure S83. MBC spectrum of 12 in methanol-d
5 Figure S84. R-ESIMS of Figure S85. 1 NMR spectrum of 13 in methanol-d Figure S C NMR spectrum of 13 in methanol-d Figure S87. SQC spectrum of 13 in methanol-d Figure S COSY spectrum of 13 in methanol-d Figure S89. MBC spectrum of 13 in methanol-d Figure S90. R-ESIMS of Figure S91. 1 NMR spectrum of 15 in pyridine-d Figure S C NMR spectrum of 15 in pyridine-d Figure S93. SQC spectrum of 15 in pyridine-d Figure S COSY spectrum of 15 in pyridine-d Figure S95. MBC spectrum of 15 in pyridine-d Figure S96. NOESY spectrum of 15 in pyridine-d Figure S97. R-ESIMS of
6 1. Key 2D NMR Correlations of 2, 5, 8, 9, 11 13, and 15 Figure S1. Key 1-1 COSY (bold lines) and MBC (plain arrows) correlations of 2, 5, 8, 9, 11 13, and 15. Figure S2. Key NOE (dashed arrows) correlations of 15. 6
7 2. Method for ECD/TDDFT Computations Molecular Merck force field (MMFF) and DFT/TDDFT calculations were performed with Spartan'14 software package (Wavefunction Inc., Irvine, CA, USA) and Gaussian09 program package, 1 respectively, using default grids and convergence criteria. In order to save the computational costs, the truncated structures (Figure S3) were used in the theoretical computations. MMFF conformational search generated low-energy conformers within a 10 kcal/mol energy window were subjected to geometry optimization using the B3LYP/6-31G(d) method. Frequency calculations were run with the same method to verify that each optimized conformer was a true minimum and to estimate their relative thermal free energies (ΔG) at K. Energies of the low-energy conformers (Figure S4) in MeO were calculated at the B3LYP/def2-TZVP level. Solvent effects were taken into account by using polarizable continuum model (PCM). The TDDFT calculations were performed using the hybrid B3LYP, 2 M06, 3 and/or M06-2X 3 functionals, and Ahlrichs basis set TZVP (triple zeta valence plus polarization). 4 The number of excited states per each molecule was 20 (for 9 and 13) or 12 (for others). The ECD spectra were generated by the program SpecDis 5 using a Gaussian band shape from dipole-length dipolar and rotational strengths. Equilibrium population of each conformer at K was calculated from its relative free energies using Boltzmann statistics. The calculated spectra were generated from the low-energy conformers according to the Boltzmann weighting of each conformer in MeO solution. Figure S3. Truncated structures used in theoretical calculations 7
8 (18S,19S)-3a ΔE = 0.07, ΔG = 0.0, P = 39.7 (18S,19S)-3b ΔE = 0.0, ΔG = 0.02, P = 38.1 (18S,19S)-3c ΔE = 0.81, ΔG = 0.56, P = 15.5 (18S,19S)-3d ΔE = 0.95, ΔG = 1.05, P = 6.7 (18R,19R)-3a ΔE = 0.0, ΔG = 0.0, P = 88.1 (18R,19R)-3b ΔE = 1.63, ΔG = 1.38, P = 8.6 (18R,19R)-3c ΔE = 2.21, ΔG = 1.94, P = 3.3 6a ΔE = 0.0, ΔG = 0.0, P =
9 9a ΔE = 0.0, ΔG = 0.11, P = b ΔE = 0.39, ΔG = 0.0, P = a ΔE = 0.0, ΔG = 0.0, P = b ΔE = 0.37, ΔG = 0.23, P = 40.4 (18S,19S)-15a ΔE = 0.0, ΔG = 0.0, P = (18R,19R)-15a ΔE = 0.0, ΔG = 0.0, P = Figure S4. Low-energy conformers and their relative thermal energies (ΔE, kcal/mol), relative free energies (ΔG, kcal/mol), and equilibrium populations (P, %; from ΔG values at K) of truncated structures of 3, 6, 9, 13, and 15 in MeO. Conformers with ΔG 3.0 kcal/mol were not considered. The molecular coordinates can be obtained from the corresponding author on request. 9
10 References (1) Frisch, M. J.; Trucks, G. W.; Schlegel,. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji,.; Caricato, M.; Li, X.; ratchian,. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; ada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; asegawa, J.; Ishida, M.; Nakajima, T.; onda, Y.; Kitao, O.; Nakai,.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; eyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision C.01. Gaussian, Inc.: Wallingford CT, (2) (a) Becke, A. D. J. Chem. Phys. 1993, 98, (b) Becke, A. D. Phys. Rev. A: At., Mol., Opt. Phys. 1988, 38, (c) Lee, T.; Yang, W. T.; Parr, R. G. Phys. Rev. B: Condens. Matter Mater. Phys. 1988, 37, (3) Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, (4) Schäfer, A.; uber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, (5) Bruhn, T.; Schaumlöffel, A.; emberger, Y.; Bringmann, G. Chirality 2013, 25, NMR Spectra and RESIMS 10
11 COO O CO Figure S5. 1 NMR (500 Mz) spectrum of 1 in pyridine-d 5 Figure S6. 13 C NMR (125 Mz) spectrum of 1 in pyridine-d 5 11
12 COO O CO Figure S7. SQC spectrum of 1 in pyridine-d 5 Figure S COSY spectrum of 1 in pyridine-d 5 12
13 COO O CO Figure S9. MBC spectrum of 1 in pyridine-d 5 Figure S10. NOESY spectrum of 1 in pyridine-d 5 13
14 COO O CO Figure S11. RESI( )MS of 1 14
15 COOC 3 O COO Figure S12. 1 NMR (500 Mz) spectrum of 2 in pyridine-d 5 Figure S C NMR (125 Mz) spectrum of 2 in pyridine-d 5 15
16 COOC 3 O COO Figure S14. SQC spectrum of 2 in pyridine-d 5 Figure S COSY spectrum of 2 in pyridine-d 5 16
17 COOC 3 O COO Figure S16. MBC spectrum of 2 in pyridine-d 5 Figure S17. NOSEY spectrum of 2 in pyridine-d 5 17
18 COOC 3 O COO Figure S18. RESI(+)MS of 2 18
19 Figure S19. 1 NMR (500 Mz) spectrum of 3 in pyridine-d 5 Figure S C NMR (125 Mz) spectrum of 3 in pyridine-d 5 19
20 Figure S21. SQC spectrum of 3 in pyridine-d 5 Figure S COSY spectrum of 3 in pyridine-d 5 20
21 Figure S23. MBC spectrum of 3 in pyridine-d 5 Figure S24. NOESY spectrum of 3 in pyridine-d 5 21
22 Figure S25. RESI(+)MS of 3 22
23 O O COO Figure S26. 1 NMR (500 Mz) spectrum of 4 in pyridine-d 5 Figure S C NMR (125 Mz) spectrum of 4 in pyridine-d 5 23
24 O O COO Figure S28. SQC spectrum of 4 in pyridine-d 5 Figure S COSY spectrum of 4 in pyridine-d 5 24
25 O O COO Figure S30. MBC spectrum of 4 in pyridine-d 5 Figure S31. NOSEY spectrum of 4 in pyridine-d 5 25
26 O O COO Figure S32. RESI(+)MS of 4 26
27 COOC 3 O COO Figure S33. 1 NMR (500 Mz) spectrum of 5 in pyridine-d 5 Figure S C NMR (125 Mz) spectrum of 5 in pyridine-d 5 27
28 COOC 3 O COO Figure S35. SQC spectrum of 5 in pyridine-d 5 Figure S COSY spectrum of 5 in pyridine-d 5 28
29 COOC 3 O COO Figure S37. MBC spectrum of 5 in pyridine-d 5 Figure S38. NOSEY spectrum of 5 in pyridine-d 5 29
30 COOC 3 O COO Figure S39. RESI( )MS of 5 30
31 Figure S40. 1 NMR (500 Mz) spectrum of 6 in methanol-d 4 Figure S C NMR (125 Mz) spectrum of 6 in methanol-d 4 31
32 Figure S42. SQC spectrum of 6 in methanol-d 4 Figure S COSY spectrum of 6 in methanol-d 4 32
33 Figure S44. MBC spectrum of 6 in methanol-d 4 Figure S45. NOESY spectrum of 6 in methanol-d 4 33
34 Figure S46. RESI( )MS of 6 34
35 Figure S47. 1 NMR (500 Mz) spectrum of 7 in methanol-d 4 Figure S C NMR (125 Mz) spectrum of 7 in methanol-d 4 35
36 Figure S49. SQC spectrum of 7 in methanol-d 4 Figure S COSY spectrum of 7 in methanol-d 4 36
37 Figure S51. MBC spectrum of 7 in methanol-d 4 Figure S52. NOESY spectrum of 7 in methanol-d 4 37
38 Figure S53. RESI(+)MS of 7 38
39 Figure S54. 1 NMR (500 Mz) spectrum of 8 in methanol-d 4 Figure S C NMR (125 Mz) spectrum of 8 in methanol-d 4 39
40 Figure S56. SQC spectrum of 7 in methanol-d 4 Figure S COSY spectrum of 8 in methanol-d 4 40
41 Figure S58. MBC spectrum of 8 in methanol-d 4 Figure S59. RESI(+)MS of 7 41
42 Figure S60. 1 NMR (500 Mz) spectrum of 9 in methanol-d 4 Figure S C NMR (125 Mz) spectrum of 9 in methanol-d 4 42
43 Figure S62. SQC spectrum of 9 in methanol-d 4 Figure S COSY spectrum of 9 in methanol-d 4 43
44 Figure S64. MBC spectrum of 9 in methanol-d 4 Figure S65. RESI( )MS of 9 44
45 Figure S66. 1 NMR (500 Mz) spectrum of 10 in pyridine-d 5 Figure S C NMR (125 Mz) spectrum of 10 in pyridine-d 5 45
46 Figure S68. SQC spectrum of 10 in pyridine-d 5 Figure S COSY spectrum of 10 in pyridine-d 5 46
47 Figure S70. MBC spectrum of 10 in pyridine-d 5 Figure S71. NOESY spectrum of 10 in pyridine-d 5 47
48 Figure S72. RESI( )MS of 10 48
49 Figure S73. 1 NMR (500 Mz) spectrum of 11 in methanol-d 4 Figure S C NMR (125 Mz) spectrum of 11 in methanol-d 4 49
50 Figure S75. SQC spectrum of 11 in methanol-d 4 Figure S COSY spectrum of 11 in methanol-d 4 50
51 Figure S77. MBC spectrum of 11 in methanol-d 4 Figure S78. RESI(+)MS of 11 51
52 Figure S79. 1 NMR (500 Mz) spectrum of 12 in methanol-d 4 Figure S C NMR (125 Mz) spectrum of 12 in methanol-d 4 52
53 O O 3 CO COO O Figure S81. SQC spectrum of 12 in methanol-d 4 Figure S COSY spectrum of 12 in methanol-d 4 53
54 O O 3 CO COO O Figure S83. MBC spectrum of 12 in methanol-d 4 Figure S84. RESI( )MS of 12 54
55 O O O COO O Figure S85. 1 NMR (500 Mz) spectrum of 13 in methanol-d 4 Figure S C NMR (125 Mz) spectrum of 13 in methanol-d 4 55
56 O O O COO O Figure S87. SQC spectrum of 13 in methanol-d 4 Figure S COSY spectrum of 13 in methanol-d 4 56
57 O O O COO O Figure S89. MBC spectrum of 13 in methanol-d 4 Figure S90. RESI( )MS of 13 57
58 Figure S91. 1 NMR spectrum of 15 in pyridine-d 5 Figure S C NMR spectrum of 15 in pyridine-d 5 58
59 O O O O Figure S93. SQC spectrum of 15 in pyridine-d 5 Figure S COSY spectrum of 15 in pyridine-d 5 59
60 O O O O Figure S95. MBC spectrum of 15 in pyridine-d 5 Figure S96. NOESY spectrum of 15 in pyridine-d 5 60
61 Figure S97. RESI(+)MS of 15 61
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