Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations
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1 Enantiomeric Lignans and Neolignans from Phyllanthus glaucus: Enantioseparation and Their Absolute Configurations Zhaodi Wu, 1,* Yongji Lai, 2,* Lei Zhou, 1 Ye Wu, 1 Hucheng Zhu, 1 Zhengxi Hu, 1 Jing Yang, 3 Jinwen Zhang, 4 Jianping Wang, 1 Zengwei Luo, 1 Yongbo Xue, 1 and Yonghui Zhang 1 1 Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 433, Hubei Province, People s Republic of China. 2 Department of Pharmacy, the Central Hospital of Wuhan, Wuhan 4314, Hubei Province, People s Republic of China. 3 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 6524, People s Republic of China. 4 Tongji Hospital Affiliated to Tongji Medical College,Huazhong University of Science and Technology,Wuhan 433, People s Republic of China. * These authors contributed equally to the work. Correspondence and requests for materials should be addressed to Y. Z. (zhangyh@mails.tjmu.edu.cn) or Y. X. (yongboxue@mail.hust.edu.cn)
2 CONTENTS ECD Calculations for compound 7R,8R-2 at LC-wPBE/ G(2d,p)//B3LYP/ G(2d,p) level... 3 ECD Calculations for compound 7R,8R-2 at CAM-B3LYP/ G(2d,p)//B3LYP/ G(2d,p) level ECD Calculations for compound 7R,8R-2 at WB97XD/ G(2d,p)//B3LYP/ G(2d,p) level HRESIMS, UV, IR, and NMRspectra of HRESIMS, UV, IR, and NMRspectra of HRESIMS, UV, IR, and NMRspectra of HRESIMS, UV, IR, and NMRspectra of HRESIMS, UV, IR, and NMRspectra of HRESIMS, UV, IR, and NMRspectra of HRESIMS, UV, IR, and NMRspectra of HRESIMS, UV, IR, and NMRspectra of Chiral HPLC separation profiles of 1a/1b 8a/8b... 56
3 ECD Calculation a b c d e f g h i Figure S1. Optimized geometries of predominant conformers for compound 7R,8R-2 at the B3LYP/ G(2d,p) level in MeOH using the IEFPCM solvation model. 3
4 Table S1. Important thermodynamic parameters (a.u.) and Boltzmann distributions of the optimized compound 7R,8R-2 calculated at LC-wPBE/ G(2d,p)//B3LYP/ G(2d,p) level in MeOH with IEFPCM solvation model. Conformations E+ZPE G % a b c d e f g h i E is the total electronic energy in MeOH at LC-wPBE/ G(2d,p)//B3LYP/ G(2d,p) level with IEFPCM solvation model, ZPE is the zero point energy in MeOH at B3LYP/ G(2d,p) level with IEFPCM solvation model, and G is the Gibbs free energy by the sum of E and the thermal correction obtained at B3LYP/ G(2d,p) level. %: Boltzmann distributions, using the relative Gibbs free energies as weighting factors. Table S2. Optimized coordinates of 7R,8R-2 in MeOH (Å) at B3LYP/ G(2d,p) level using IEFPCM solvation model. a b C C C C C C C C C C C C O O C C C C C C C C C C C C C C C C
5 O O C C O O O O C C O O C C O O C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H c d C C C C C C C C C C C C O O C C C C C C C C
6 C C C C C C C C O O C C O O O O C C O O C C O O C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H e f C C C C C C C C C C C C O O
7 C C C C C C C C C C C C C C C C O O C C O O O O C C O O C C O O C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H g h C C C C C C
8 C C C C C C O O C C C C C C C C C C C C C C C C O O C C O O O O C C O O C C O O C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
9 i C C C C C C O C C C C C C C C O C O O C O C O C H H H H H H H H H H H H H H H H H H
10 H H H H (a) (b) (c) (d) (e).4 (f) 1
11 (g) (h) (i) Figure S2. Calculated ECDs of each conformations of 7R,8R-2 (calculated at the LC-wPBE/ G(2d,p)//B3LYP/ G(2d,p) level in MeOH with IEFPCM solvation model. 11
12 Table S3. Important thermodynamic parameters (a.u.) and Boltzmann distributions of the optimized compound 7R,8R-2 calculated at CAM-B3LYP/ G(2d,p)//B3LYP/ G(2d,p) level in MeOH with IEFPCM solvation model. Conformations E+ZPE G % a b c d e f g h i E is the total electronic energy in MeOH at CAM-B3LYP/ G(2d,p)//B3LYP/ G(2d,p) level with IEFPCM solvation model, ZPE is the zero point energy in MeOH at B3LYP/ G(2d,p) level with IEFPCM solvation model, and G is the Gibbs free energy by the sum of E and the thermal correction obtained at B3LYP/ G(2d,p) level. %: Boltzmann distributions, using the relative Gibbs free energies as weighting factors (a) (b) 12
13 (c) (d) (e) (f) (g) (h) (i) Figure S3. Calculated ECDs of each conformations of 7R,8R-2 (calculated at the 13
14 CAM-B3LYP/ G(2d,p)//B3LYP/ G(2d,p) level in MeOH with IEFPCM solvation model. Figure S4. Calculated and experimental ECDs of 2 and 7R,8R-2 at the CAM-B3LYP/ G(2d,p)//B3LYP/ G(2d,p) level in MeOH with IEFPCM solvation model. Table S4. Important thermodynamic parameters (a.u.) and Boltzmann distributions of the optimized compound 7R,8R-2 calculated at WB97XD/ G(2d,p)//B3LYP/ G(2d,p) level in MeOH with IEFPCM solvation model. Conformations E+ZPE G % a b c d e f g h i E is the total electronic energy in MeOH at WB97XD/ G(2d,p)//B3LYP/ G(2d,p) level with IEFPCM solvation model, ZPE is the zero point energy in MeOH at B3LYP/ G(2d,p) level with IEFPCM solvation model, and G is the Gibbs free energy by the sum of E and the thermal correction obtained at B3LYP/ G(2d,p) level. %: Boltzmann 14
15 distributions, using the relative Gibbs free energies as weighting factors (a)(b) (c) (d) (e) (f)
16 (g) (h) (i) Figure S5. Calculated ECDs of each conformations of 7R,8R-2 (calculated at the WB97XD/ G(2d,p)//B3LYP/ G(2d,p) level in MeOH with IEFPCM solvation model. FigureS6. Calculated and experimental ECDs of 2 and 7R,8R-2 at the WB97XD/ G(2d,p)//B3LYP/ G(2d,p) level in MeOH with IEFPCM solvation model. 16
17 HRESIMS of compound 1 T: FTMS + p ESI Full ms [5.-15.] Relative Abundance m/z UV spectrum of compound 1 17
18 IR spectrum of compound Transmittance [%] Wavenumber cm-1 1 H NMR of compound 1 18
19 13 C NMR and DEPT of compound 1 HSQC of compound 1 19
20 HMBC of compound 1 1 H 1 H COSY of compound 1 2
21 NOESY of compound 1 HRESIMS of compound 2 HO 5 3 O OH 9 1' 1 7 O O 3' 5' OH 21
22 UV spectrum of compound 2 IR spectrum of compound Transmittance [%] Wavenumber cm
23 1 H NMR of compound 2 13 C NMR and DEPT of compound 2 23
24 HSQC of compound 2 HMBC of compound 2 24
25 1 H 1 H COSY of compound 2 NOESY of compound 2 25
26 HRESIMS of compound 3 UV spectrum of compound 3 26
27 IR spectrum of compound Transmittance [%] Wavenumber cm H NMR of compound 3 27
28 13 C NMR and DEPT of compound 3 HSQC of compound 3 28
29 HMBC of compound 3 1 H 1 H COSY of compound 3 29
30 NOESY of compound 3 HRESIMS of compound 4 yj T: FTMS + p ESI Full ms [5.-15.] Relative Abundance m/z 3
31 UV spectrum of compound 4 IR spectrum of compound Transmittance [%] Wavenumber cm
32 1 H NMR of compound 4 13 C NMR and DEPT of compound 4 32
33 HSQC of compound 4 HMBC of compound 4 33
34 1 H 1 H COSY of compound 4 NOESY of compound 4 34
35 HRESIMS of compound 5 T: FTMS + p ESI Full ms [5.-15.] Relative Abundance UV spectrum of compound m/z 35
36 IR spectrum of compound 5 Transmittance [%] Wavenumber cm H NMR of compound 5 36
37 13 C NMR and DEPT of compound 5 HSQC of compound 5 37
38 HMBC of compound 5 1 H 1 H COSY of compound 5 38
39 NOESY of compound 5 1 H NMR of compound 5 in Acetone-d 6 (4 MHz) 39
40 HRESIMS of compound 6 UV spectrum of compound 6 4
41 IR spectrum of compound Transmittance [%] Wavenumber cm H NMR of compound 6 41
42 13 C NMR and DEPT of compound 6 HSQC of compound 6 42
43 HMBC of compound 6 1 H 1 H COSY of compound 6 43
44 NOESY of compound 6 1 H NMR of compound 6 in Acetone-d 6 (4 MHz) 44
45 HRESIMS of compound 7 UV spectrum of compound 7 45
46 IR spectrum of compound Transmittance [%] Wavenumber cm-1 46
47 1 H NMR of compound 7 47
48 13 C NMR and DEPT of compound 7 HSQC of compound 7 48
49 HMBC of compound 7 1 H 1 H COSY of compound 7 49
50 NOESY of compound 7 1 H NMR of compound 7 in Acetone-d 6 (4 MHz) 5
51 HRESIMS of compound 8 T: FTMS + p ESI Full ms [5.-15.] Relative Abundance m/z UV spectrum of compound 8 51
52 IR spectrum of compound Transmittance [%] Wavenumber cm H NMR of compound 8 52
53 13 C NMR and DEPT of compound 8 HSQC of compound 8 53
54 HMBC of compound 8 1 H 1 H COSY of compound 8 54
55 NOESY of compound 8 1 H NMR of compound 8 in Acetone-d 6 (4 MHz) 55
56 Chiral HPLC separation profiles of 1a/1b 8a/8b 56
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