Antioxidant Activities of Chemical Constituents Isolated from Echinops orientalis Trauv.
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1 Supporting Information Rec. Nat. Prod. :1 (014) 3-36 Antioxidant Activities of Chemical Constituents Isolated from Echinops orientalis Trauv. Ramazan Erenler 1, SakineYilmaz 1, useyin Aksit 1, zkan Sen 1, Nusret Genc 1, Mahfuz Elmastas 1 and Ibrahim Demirtas 1 Department of Chemistry, Faculty of Art and Science, Gaziosmanpasa University, Taslıciftlik Campus, 6040 Tokat, Türkiye Department of Chemistry, Faculty of Science, Cankiri Karatekin University, Ballica Campus, 1100 Cankiri, Türkiye Table of Contents Page S1: 1 -NMR (400 Mz, DMS-d6) Spectrum of Compound 1 3 S: 13 C-NMR (100 Mz, DMS-d6) Spectrum of compound 1 4 S3: DEPT-90 (100 Mz, DMS-d6) Spectrum of compound 1 S4: DEPT-90 (100 Mz, DMS-d6) Spectrum of compound 1 (Expanded) 6 S: APT (100 Mz, DMS-d6) Spectrum of compound 1 7 S6: ETCR (400 Mz, DMS-d6) Spectrum of compound 1 S7: CSY-90 (400 Mz, DMS-d6) Spectrum of compound 1 9 S: MBC (400 Mz, DMS-d6) Spectrum of compound 1 10 S9: PLC-QTF Spectrum of compound 1 11 S10: 1 -NMR (400 Mz, DMS-d6) Spectrum of Compound 1 S11: 1 -NMR (400 Mz, DMS-d6) Spectrum of Compound (Expanded) 13 S1: 13 C-NMR (100 Mz, DMS-d6) Spectrum of Compound 14 S13: APT (100 Mz, DMS-d6) Spectrum of Compound 1 S14: ETCR (100 Mz, DMS-d6) Spectrum of Compound 16
2 S1: PLC-QTF Spectrum of Compound 17 S16: 1 -NMR (400 Mz, DMS-d6) Spectrum of Compound 3 1 S17: 13 C-NMR, DEPT-90, DEPT-13 (100 Mz, DMS-d6) Spectrum of Compound 3 19 S1:ETCR (400 Mz, DMS-d6) Spectrum of Compound 3 0 S19: DPP free radical scavenging activity of standarts, compounds and extracts 1 S0: ABTS + scavenging activity of standarts, compounds and extracts S1: Reducing power activity of standarts, compounds and extracts 3 S: Total phenolic compounds 4 S3: Carbon, proton and MBC data of the flavonoids (1, ) (Table 1) S4: Carbon and proton data of 1-methylquinolin-4(1)-one (3 ) (Table ) 6
3 ppm S1: 1 -NMR (400 Mz, DMS-d6) Spectrum of Compound 1 Kedi Nanesi yeni kolon fr 114 coken 3''' 1''' '' '' '' 1'' 7'''
4 ''' '' 3''' 1''' '' 1'' '' ppm S: 13 C-NMR (100 Mz, DMS-d6) Spectrum of compound 1
5 3''' 1''' 7''' '' '' 1'' '' NAME Kedi Nanesi yeni kolon fr 114 coken EXPN 3 PRCN 1 Date_ Time 1.4 INSTRUM spect PRBD mm DUL 13C-1 PULPRG dept90 TD 636 SLVENT DMS NS 471 DS 4 SW z FIDRES z AQ sec RG 00 DW 0.00 usec DE 6.0 usec TE K CNST D sec D sec D sec TD0 1 ======== CANNEL f1 ======== NUC1 13C P usec P 1.00 usec PL db PL1W W SF Mz ======== CANNEL f ======== CPDPRG waltz16 NUC 1 P usec P usec PCPD 0.00 usec PL db PL db PLW W PL1W W SF Mz SI 376 SF Mz WDW EM SSB 0 LB 1.00 z GB 0 PC ppm S3: DEPT-90 (100 Mz, DMS-d6) Spectrum of compound 1
6 ''' 1''' '' 7''' '' 1'' '' NAME Kedi Nanesi yeni kolon fr 114 coken EXPN 3 PRCN 1 Date_ Time 1.4 INSTRUM spect PRBD mm DUL 13C-1 PULPRG dept90 TD 636 SLVENT DMS NS 471 DS 4 SW z FIDRES z AQ sec RG 00 DW 0.00 usec DE 6.0 usec TE K CNST D sec D sec D sec TD0 1 ======== CANNEL f1 ======== NUC1 13C P usec P 1.00 usec PL db PL1W W SF Mz ======== CANNEL f ======== CPDPRG waltz16 NUC 1 P usec P usec PCPD 0.00 usec PL db PL db PLW W PL1W W SF Mz SI 376 SF Mz WDW EM SSB 0 LB 1.00 z GB 0 PC ppm S4: DEPT-90 (100 Mz, DMS-d6) Spectrum of compound 1(Expanded)
7 ''' '' 3''' 1''' '' 1'' '' ppm S: APT (100 Mz, DMS-d6) Spectrum of compound 1
8 ppm ppm S6: ETCR (400 Mz, DMS-d6) Spectrum of compound 1
9 ppm '' 3''' 1''' 7''' '' 1'' '' ppm S7: CSY-90 (400 Mz, DMS-d6) Spectrum of compound 1
10 ppm 3''' '' 7''' 0 1''' '' 1'' '' ppm S: MBC (400 Mz, DMS-d6) Spectrum of compound 1
11 3''' '' 7''' 1''' '' 1'' '' S9: PLC-QTF Spectrum of compound 1
12 '' '' 1'' ' ppm S10: 1 -NMR (400 Mz, DMS-d6) Spectrum of Compound
13 '' '' 1'' ' ppm ppm S11: 1 -NMR (400 Mz, DMS-d6) Spectrum of Compound (Expanded)
14 '' '' 1'' ' ppm S1: 13 C-NMR (100 Mz, DMS-d6) Spectrum of Compound
15 1.463 '' '' '' ' NAME sakine kolon 1-16 fr cokelek EXPN 3 PRCN 1 Date_ Time 4.17 INSTRUM spect PRBD mm DUL 13C-1 PULPRG jmod TD 636 SLVENT DMS NS 307 DS 4 SW z FIDRES z AQ sec RG 00 DW 0.00 usec DE 6.0 usec TE K CNST CNST D sec D sec TD0 1 ======== CANNEL f1 ======== NUC1 13C P usec P 1.00 usec PL db PL1W W SF Mz ======== CANNEL f ======== CPDPRG waltz16 NUC 1 PCPD 0.00 usec PL db PL db PLW W PL1W W SF Mz SI 376 SF Mz WDW EM SSB 0 LB 1.00 z GB 0 PC ppm S13: APT (100 Mz, DMS-d6) Spectrum of Compound
16 '' 1'' '' 7 1 ' 4 3 S14: ETCR (100 Mz, DMS-d6) Spectrum of Compound
17 '' 1'' '' 7 1 ' 4 3 S1: PLC-QTF Spectrum of Compound
18 N ppm ppm S16: 1 -NMR (400 Mz, DMS-d6) Spectrum of Compound 3 sakine tohum kolon 34-3
19 3 N S17: 13 C-NMR, DEPT-90, DEPT-13 (100 Mz, DMS-d6) Spectrum of Compound 3
20 ETCR.ESP F Chemical Shift (ppm) F1 Chemical Shift (ppm) N S1:ETCR (400 Mz, DMS-d6) Spectrum of Compound 3
21 S19: DPP free radical scavenging activity of standards, compounds and extracts
22 S0: ABTS + scavenging activity of standards, compounds and extracts
23 S1: Reducing power activity of standard, compounds and extracts
24 S: Total phenolic compounds
25 Table 1. Carbon, proton and MBC data of the flavonoids (1, ). Compound 1 Compound C/ δ C ppm δ (J z) MBC ( C) C/ δ C δ (J z) s -3/C-, 4, 10, 1' s s s (d, J=.1) -6/C-7, brs (d, J=.1) -/C-6, 7, 9, (d, J= 1.) ' ' 11.4 ', 6' (d, J=.) -', 6'/C-, ', 6' (d, J =.4) 3', ' (d, J=.) -3', '/ C-1', 3', ' (d, J =.4) Glucose 1'' (d, J = 7.3) -1''/C-7 1'' (d, J = 7.0) '' (t, J = 7.3) '' (t, J = 7.0) 3'' m 3'' m ' m ' m '' m '' m a m a m b m b m s s coumaroyl 1''' ''' (d, J = 1.) -"'/C-1''', 3"', 3''' (d, J = 1.) -3"'/C-"', 4"' '' 1.3 ''', 9"' (d, J =.6) -"', 9"'/C-4"', 6"', "', 7"' ', "' (d, J=.6) -6"', "'/C-"', 9"', 7"', 4"' 7''' 160.
26 Table. Carbon and proton data of 1-methylquinolin-4(1)-one (3 ) C/ δ C ppm δ (J z) MBC ( C) (d,j=.0) -/C-3, 4, (d, J =.0) -3/C-, 4, (d, J =.0) -/C-6, (t, J =.0) -6/C-, 7, (ddd, J =.0, 1.6) -7/C-6, (dd, J =.0, 1.6) -/C-4, 6, 7, C s
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