Molecules 2017, 22, 236; doi: /molecules S1 of S21 Supplementary Materials: Bioactive Stilbenes from Cortex Mori Radicis, and Their Neur

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1 S1 of S21 Supplementary Materials: Bioactive Stilbenes from Cortex Mori Radicis, and Their Neuroprotective and Analgesic Activities Mediated by mglur1 Ya-Nan Wang, Mao-Feng Liu, Wei-Zhen Hou, Rui-Ming Xu, Jie Gao, An-Qi Lu, Mei-Ping Xie, Lan Li, Jian-Jun Zhang, Ying Peng, Li-Li Ma, Xiao-Liang Wang, Jian-Gong Shi and Su-Juan Wang Supporting information Figure SI-1a. 1 HNMR spectra of compound 1 Figure SI-1b. 13 CNMR spectra of compound 1 Figure SI-1c. HMQC spectra of compound 1 Figure SI-1d. HMBC spectra of compound 1 Figure SI-1e. (+)ESIMS spectra of compound 1 Figure SI-1f. IR spectra of compound 1 Figure SI-1g. CD and UV spectrum of compound 1 Figure SI-1h. The absolute configuration of sugar in 1 detered by HPLC Figure SI-2a. 1 HNMR spectra of compound 2 Figure SI-2b. 13 CNMR spectra of compound 2 Figure SI-2c. HMQC spectra of compound 2 Figure SI-2d. HMBC spectra of compound 2 Figure SI-2e. (+)ESIMS spectra of compound 2 Figure SI-2f. IR spectra of compound 2 Figure SI-2g. CD and UV spectrum of compound 2 Figure SI-2h. The absolute configuration of sugar in 2 detered by HPLC Figure SI-3a. 1 HNMR spectra of compound 3 Figure SI-3b. 13 CNMR spectra of compound 3 Figure SI-3c. HMQC spectra of compound 3 Figure SI-3d. HMBC spectra of compound 3 Figure SI-3e. (+)ESIMS spectra of compound 3 Figure SI-3f. IR spectra of compound 3 Figure SI-3g. CD and UV spectrum of compound 3 Figure SI-3h. The absolute configuration of sugar in 3 detered by HPLC Figure SI-4a. 1 HNMR spectra of compound 4 Figure SI-4b. 13 CNMR spectra of compound 4 Figure SI-4c. HMQC spectra of compound 4 Figure SI-4d. HMBC spectra of compound 4 Figure SI-4e. (+)ESIMS spectra of compound 4 Figure SI-4f. IR spectra of compound 4 Figure SI-4g. CD and UV spectrum of compound 4 Figure SI-4h. The absolute configuration of sugar in 4 detered by HPLC Table SI-1. Optical rotation of aglycones 1a 4a, moracin O (5), and P (8) Calculated ECD of 1a Figure SI-5a. Calculated ECD spectra of 1a-C1 C3

2 S2 of S21 Table SI-2. The Boltzmann distribution of three conformations (C1 C3) of 1a Figure SI-5b. MO related with two cotton effects of 1a HPLC profile of Cortex Mori Radicis and their main components identified by HPLC-MS Figure SI-6. HPLC profile of Cortex Mori Radicis Table SI-3. The main components of Cortex Mori Radicis identified by HPLC-MS Figure SI-1a. 1 H NMR spectra of compound 1.

3 S3 of S21 Figure SI-1b. 13 C NMR spectra of compound 1. Figure SI-1c. HMQC spectra of compound 1.

4 S4 of S21 Figure SI-1d. HMBC spectra of compound 1. x MS,. # m/z Figure SI-1e. (+)ESIMS spectra of compound 1.

5 S5 of S21 Figure SI-1f. IR spectra of compound 1. Figure SI-1g. CD and UV spectrum of compound 1.

6 S6 of S DAD1 A, Sig=25,4 Ref=36,1 (H:\ D) DAD1 A, Sig=25,4 Ref=36,1 (H:\ D) DAD1 A, Sig=25,4 Ref=36,1 (H:\ D) Compd 1* L-ara D-ara Figure SI-1h. HPLC of compound 1, D-arabinose, L-arabinose. Figure SI-2a. 1 H NMR spectra of compound 2.

7 S7 of S21 Figure SI-2b. 13 C NMR spectra of compound 2. Figure SI-2c. HMQC spectra of compound 2.

8 S8 of S21 Figure SI-2d. HMBC spectra of compound 2. Intens. x1 6 +MS,.2 # m/z Figure SI-2e. (+)ESIMS spectra of compound 2.

9 S9 of S21 Figure SI-2f. IR spectra of compound 2. Figure SI-2g. CD and UV spectrum of compound 2.

10 S1 of S21 DAD1 A, Sig=25,4 Ref=6,1 (H:\ D) Compd 2* DAD1 A, Sig=25,4 Ref=6,1 (H:\ D) D-glc DAD1 A, Sig=25,4 Ref=6,1 (H:\ D) L-glc Figure SI-2h. HPLC of compound 2, D-glucose and L-glucose. Figure SI-3a. 1 H NMR spectra of compound 3.

11 S11 of S21 Figure SI-3b. 13 C NMR spectra of compound 3. Figure SI-3c. HMQC spectra of compound 3.

12 S12 of S21 compound 3 SBP-34-2/3 Bruker AVIIIHD {HMBC etgpl3nd} DMSO D:\\ DATA f2 (ppm) Figure SI-3d. HMBC spectra of compound 3. 5 x Scan (6.319 ) d Subtract Counts (%) vs. Mass-to-Charge (m/z) Figure SI-3e. (+)ESIMS spectra of compound 3.

13 S13 of S21 Figure SI-3f. IR spectra of compound 3. Figure SI-3g. CD and UV spectrum of compound 3.

14 S14 of S DAD1 A, Sig=25,4 Ref=36,1 (H:\ D) DAD1 A, Sig=25,4 Ref=36,1 (H:\ D) DAD1 A, Sig=25,4 Ref=36,1 (H:\ D) Compd 3* D-glc L-glc Figure SI-3h. HPLC of compound 3, D-glucose and L-glucose. Figure SI-4a. 1 H NMR spectra of compound 4.

15 S15 of S21 Figure SI-4b. 13 C NMR spectra of compound 4. Figure SI-4c. HMQC spectra of compound 4.

16 S16 of S21 compound 4 SBP-31-1/3 Bruker AVIIIHD {HMBC etgpl3nd} DMSO D:\\ DATA f2 (ppm) Figure SI-4d. HMBC spectra of compound 4. Intens. x1 6 +MS,.2 # m/z Figure SI-4e. (+)ESIMS spectra of compound 4.

17 S17 of S21 Figure SI-4f. IR spectra of compound 4. Figure SI-4g. CD and UV spectrum of compound 4.

18 S18 of S DAD1 A, Sig=25,4 Ref=36,1 (H:\ D) DAD1 A, Sig=25,4 Ref=36,1 (H:\ D) DAD1 A, Sig=25,4 Ref=36,1 (H:\ D) Compd D-glc L-glc Figure SI-4h. HPLC of compound 4, D-glucose and L-glucose. Table SI-1. Optical rotation of aglycones 1a 4a, moracin O (5), and P (8). Compounds [α] 2 D (c.1 MeOH) [α] 28 D (c.4 MeOH) 1a.328 * 2a.21 * 3a.263 * 4a.95 * Moracin O (5) Moracin P (8) * [α] 2 D can t be calculated due to the non-quantitative deteration.

19 S19 of S21 Calculated ECD of 1a and MO Analysis Calculated ECD was carried out on R configuration of 1a. Conformation search was done with the MMFF94 using the MOE software package (MOE29.1, Chemical Computing Group, Montreal, QC, Canada). Calculated ECD was performed using TDDFT (Gaussian 9 B.1, Gaussian, Wallingford, CT, 29) at B3LYP/6-31+G(d,p)//B3LYP/6-311+G(d,p) level for the configurations within an energy window of 5 kcal/mol. The conductor-like polarizable continuum model was used with MeOH (ε = ) to take the solvent effects into consideration. The Boltzmann distribution was calculated based on the relative free energy (ΔG), and the final ECD (σ =.2 ev, UV shift = 15 nm) was simulated by using SpecDis (V1.64, University of Wuerzburg, Germany, 215). Table SI-2. The Boltzmann distribution of three conformations (C1 C3) of 1a Conformations of 1a ΔG (Kcal/mol) Boltzmann distribution (%) C C C calcd.1a MO: exp.1a MO: a-C a-C2 1a-C3 MO: MO: MO: MO: Figure SI-5a. Calculated ECD spectra of 1a-C1 C3.

S2 of S21... MO86: HOMO π of 2-benzylbenzofuran. MO87: LUMO π* of 2-benzylbenzofuran.

MO related with two Cotton effects of 1a.

HPLC condition: The mobile solvent was:.1% formic acid (A) and B: MeOH (B).

ml/. The column was Previl C18 (Grace, 25 4.6mm, 5μ). 7 2.89 23.129 6 3.

20 S2 of S21... MO86: HOMO π of 2-benzylbenzofuran. MO87: LUMO π* of 2-benzylbenzofuran.. MO89: LUMO+2 π* of benzyl moiety. MO9: LUMO+3 π* of benzofuran moiety Figure SI-5b. MO related with two Cotton effects of 1a. HPLC Profile of Cortex Mori Radicis and Their Main Components Identified by HPLC-MS HPLC condition: The mobile solvent was:.1% formic acid (A) and B: MeOH (B). The gradient was: 1% B ( ) 1% B (3 ). The wavelength was 29 nm. The flow rate was 1. ml/. The column was Previl C18 (Grace, mm, 5μ) Figure SI-6. HPLC profile of Cortex Mori Radicis.

21 S21 of S21 Table SI-3. Main components of Cortex Mori Radicis identified by HPLC-MS R.T. Area Area % M.W. Name Compound N.O moracin R oxyresveratrol , 3, mulberroside C morin moracin O moracin P morusin isomulberrofuran G mulberrofuran G norartocarpetin Sanggenon D cathayanins B Sanggenon C The area % was calculated by the area of 29 nm.

Microsoft Word _File000009_ doc

Microsoft Word _File000009_ doc Supporting information Cyclizidine-type Alkaloids from the Streptomyces sp. HNA39 Yong-Jun Jiang, Jia-Qi Li, Hao-Jian Zhang, Wan-Jing Ding, and Zhong-Jun Ma * Institute of Marine Biology, Ocean College,