Phenylpropanoids, Sesquiterpenoids and Flavonoids from Pimpinella tragium Vill. subsp. lithophila (Schischkin) Tutin
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1 Supporting Information Rec. Nat. Prod. 10:2 (2016) Phenylpropanoids, Sesquiterpenoids and Flavonoids from Pimpinella tragium Vill. subsp. lithophila (Schischkin) Tutin Hilal Özbek 1, Zühal Güvenalp 1*, Ayşe Kuruüzüm-Uz 2, Cavit Kazaz 3 and L. Ömür Demirezer 2 1 Department of Pharmacognosy, Faculty of Pharmacy, Atatürk University, Erzurum, Türkiye 2 Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Türkiye 3 Department of Chemistry, Faculty of Science, Atatürk University, Erzurum 25240, Türkiye Table of Contents Page S1: HR-ESI-MS Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-D- glucoside) 3 S2: 1 H-NMR (400 MHz, CD 3 D) Spectrum of Compound 1 (Germacradiene-6--(6'-acetyl)-β-D-glucoside) 4 S3: 13 C-NMR (100 MHz, CD 3 D) Spectrum of Compound 1 (Germacradiene-6--(6'-acetyl)-β-D-glucoside) 5 S4: DEPT (100 MHz) Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-Dglucoside) 6 S5: CSY (400 MHz) Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-Dglucoside) 7 S6: CSY Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-D-glucoside) (From 1.0 to 5.5 ppm) 8 S7: HMQC (400 MHz) Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-Dglucoside) 9 S8: HMQC (400 MHz) Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-Dglucoside) (From 10 to 55 ppm) 10 1
2 S9: HMQC (400 MHz) Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-Dglucoside) (From 60 to 85 ppm) 11 S10: HMBC (400 MHz) Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-Dglucoside) 12 S11: HR-ESI-MS Spectrum of Compound 2 (Rhamnetin-3--(2 --β-d-glucopyranosyl)-β- D-galactopyranoside) 13 S12: 1 H-NMR (400 MHz, CD 3 D) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) 14 S13: 13 C-NMR (100 MHz, CD 3 D) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) 15 S14: DEPT 90 (100 MHz, CD 3 D) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) 16 S15: DEPT 135 (100 MHz, CD 3 D) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) 17 S16: CSY (400 MHz) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) 18 S17: CSY Spectrum of Compound 2 (Rhamnetin-3--(2 --β-d-glucopyranosyl)-β-dgalactopyranoside) (From 3.0 to 8.0 ppm) 19 S18: HMQC (400 MHz) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) 20 S19: HMQC (400 MHz) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) (From 40 to 80 ppm) 21 S20: HMQC (400 MHz) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) (From 90 to 125 ppm) 22 S21: HMBC (400 MHz) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) 23 2
3 S1: HR-ESI-MS Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-D-glucoside) 3
4 Protons of sugar H-3a H-9a CCH 3 H-14 H-13 H-8b H-9b H-3b H-15 H-8a H-7 H-12 H-6 H-6 a H-1 H-6 b H ' H-5 H-1 H-2 H 3CC 6' 5' 2' 3' 4' H S2: 1 H-NMR (400 MHz, CD 3 D) Spectrum of Compound 1 (Germacradiene-6--(6'-acetyl)-β-D-glucoside) Germacradiene-6--(6'--acetyl)-β-D-glucoside (1): White amorphous powder. UV (λ max, CHCl 3, nm): 275, 241. IR ( max cm -1 ): 3338 (-), 1731 (C=). 1 H-NMR (CD 3 D, 400 MHz), δ: 1.23 (3H, s, H-12), 1.23 (1H, m, H-7), 1.39 (3H, s, H-13), 1.52 (3H, s, H-15), 1.70 (1H, m, H-9b), 1.71 (1H, m, H-8b), 1.71 (3H, s, H-14), 2.03 (3H, s, CCH 3 ), 2.03 (1H, m, H-8a), 2.10 (1H, m, H-3b), 2.47 (1H, dd, H-3a), 2.47 (1H, m, H-9a), 3.13 (1H, t, H-2'), 3.21 (1H, t, H-4'), 3.33 (1H, m, H-3'), 3.40 (1H, m, H-5'), 4.20 (1H, dd, H-6'b), 4.28 (1H, dd, H-6'a), 4.30 (1H, d, H-1'), 4.60 (1H, ddd, H-2), 4.82 (1H, d, H- 6), 5.05 (1H, d, H-1), 5.36 (1H, d, H-5). 13 C-NMR (CD 3 D, 100 MHz), δ: (C-1), 66.0 (C-2), 48.0 (C-3), (C-4), (C-5), 80.4 (C-6), 50.0 (C-7), 25.8 (C-8), 35.6 (C-9), (C-10), 73.3 (C- 11), 27.1 (C-12), 28.3 (C-13), 21.3 (C-14), 16.2 (C-15), (C-1'), 73.7 (C-2'), 76.8 (C-3'), 70.4 (C- 4'), 74.0 (C-5'), 63.4 (C-6'), (C=), 19.4 (CH 3 ). HR-ESI-MS: m/z (calc. for C 23 H 38 9 Na). 4
5 CCH 3 H C9 C13 C12 C8 C14 C ' 1' H 3CC 6' 5' 3' C6 C3' C5' C2' C11 C4' C2 C6' C7 4' H C3 C5 C1 CCH 3 C10 C4 C1' S3: 13 C-NMR (100 MHz, CD 3 D) Spectrum of Compound 1 (Germacradiene-6--(6'-acetyl)-β-D-glucoside) 5
6 H DEPT 90 C5 C1 C1' C3' C6 C4' C2 C H 3CC 5 7 6' 4' 5' 6 2' H 1' 3' C5' C2' C14 C12 CCH 3 C15 DEPT 135 C13 C6' C3 C9 C8 S4: DEPT (100 MHz) Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-Dglucoside) 6
7 S5: CSY (400 MHz) Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-Dglucoside) 7
8 S6: CSY Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-D-glucoside) (From 1.0 to 5.5 ppm) 8
9 C1'/H-1' C5/H-5 C1/H-1 S7: HMQC (400 MHz) Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-Dglucoside) 9
10 C14/H-14 C15/H-15 CH 3 C8/H-8 C9/H-9 C12/H-12 C13/H-13 C3/H-3 C7/H-7 S8: HMQC (400 MHz) Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-Dglucoside) (From 10 to 55 ppm) 10
11 C2/H-2 C6 /H-6 C4 /H-4 C2 /H-2 C5 /H-5 C6/H-6 C3 /H-3 S9: HMQC (400 MHz) Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-Dglucoside) (From 60 to 85 ppm) 11
12 H-6' CCH 3 H-1' C-8 CCH 3 S10: HMBC (400 MHz) Spectrum of Compound 1 (Germacradiene-6--(6'--acetyl)-β-Dglucoside) 12
13 S11: HR-ESI-MS Spectrum of Compound 2 (Rhamnetin-3--(2 --β-d-glucopyranosyl)-β- D-galactopyranoside) 13
14 CH 3 Protons of sugars H-1'' H-1''' H-2' H-6' H-5' H-8 H-6 H 3C ' 1' 3' 6' 4' 5' H 6'' 4'' 5'' 2'' 1'' 3'' 1''' 5''' 6''' H 2''' 4''' 3''' S12: 1 H-NMR (400 MHz, CD 3 D) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) Rhamnetin-3--(2 --β-d-glucopyranosyl)-β-d-galactopyranoside (2): Yellow amorphous powder, UV (λ max, Me, nm): 357, 256. IR ( max cm -1 ): 3301 (-), 1651 (C=), 1592 (C=C). 1 H-NMR (CD 3 D, 400 MHz), δ: 3.33 (1H, m, H-3 ), 3.43 (1H, m, H-2 ), 3.44 (1H, m, H-4 ), 3.45 (1H, m, H- 5 ), 3.46 (1H, m, H-5 ), 3.53 (1H, dd, H-6 b), 3.61 (1H, dd, H-6 a), 3.72 (1H, m, H-6 b), 3.73 (1H, m, H- 3 ), 3.79 (1H, m, H-6 a), 3.87 (1H, m, H-4 ), 3.87 (3H, s, CH 3 ), 4.07 (1H, t, H-2 ), 4.76 (1H, d, H-1 ), 5.29 (1H, d, H-1 ), 6.31 (1H, bs, H-6), 6.57 (1H, bs, H-8), 6.89 (1H, d, H-5 ), 7.58 (1H, dd, H-6 ), 7.77 (1H, d, H-2 ). 13 C-NMR (CD 3 D, 100 MHz), δ: (C-2), (C-3), (C-4), (C-5), 97.6 (C- 6), (C-7), 91.6 (C-8), (C-9), (C-10), (C-1'), (C-2'), (C-3'), (C- 4'), (C-5'), (C-6'), 55.1 (-CH 3 ), (C-1''), 79.2 (C-2''), 73.4 (C-3''), 68.6 (C-4''), 75.5 (C-5''), 60.4 (C-6''), (C-1'''), 74.0 (C-2'''), 76.6 (C-3'''), 69.6 (C-4'''), 76.4 (C-5'''), 60.8 (C-6'''). HR- ESI-MS: m/z (calc. for C 28 H Na). 14
15 C2''' 2' 3' 4' C3''' C5''' C5'' C2'' C3'' C4''' C4'' C6''' C6'' CH 3 H 3C ' 5' 6' H 6'' 4'' 5'' 2'' 1'' 3'' 1''' 5''' 6''' H 2''' 4''' 3''' C7 C5 C2 C9 C2' C10 C4' C1' C5' C1''' C3' C1'' C6' C6 C8 C4 C3 S13: 13 C-NMR (100 MHz, CD 3 D) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) 15
16 2' 3' 4' H 3 C ' 6' 5' C3''' C5''' H 6'' 4'' 5'' 2'' 1'' 3'' 1''' 5''' 6''' H 2''' 4''' C2'' C5'' C2''' C3'' C4''' C4'' 3''' C6' C2' C5' C1''' C1'' C6 C8 S14: DEPT 90 (100 MHz, CD 3 D) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) 16
17 2' 3' 4' H 3 C ' 6' 5' H 6'' 4'' 5'' 2'' 1'' 3'' 1''' 5''' 6''' H 2''' 4''' 3''' CH 3 C6''' C6'' S15: DEPT 135 (100 MHz, CD 3 D) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) 17
18 S16: CSY (400 MHz) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) 18
19 S17: CSY Spectrum of Compound 2 (Rhamnetin-3--(2 --β-d-glucopyranosyl)-β-dgalactopyranoside) (From 3.0 to 8.0 ppm) 19
20 S18: HMQC (400 MHz) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) 20
21 CH 3 C4 /H-4 C6 /H-6 C6 /H-6 C4 /H-4 C3 /H-3 C2 /H-2 C2 /H-2 C5 /H-5 C5 /H-5 C3 /H-3 S19: HMQC (400 MHz) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) (From 40 to 80 ppm) 21
22 C8/H-8 C6/H-6 C1 /H-1 C1 /H-1 C2 /H-2 C5 /H-5 C6 /H-6 S20: HMQC (400 MHz) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) (From 90 to 125 ppm) 22
23 CH 3 H-1'' H-1''' C-2'' C-3 C-7 S21: HMBC (400 MHz) Spectrum of Compound 2 (Rhamnetin-3--(2 --β-dglucopyranosyl)-β-d-galactopyranoside) 23
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