Antioxidant Activities of Chemical Constituents Isolated from Echinops orientalis Trauv.

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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

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

1.03 0. 1.16 1.07 0.99.07.1.16 1.94 1.14.00 1.0.40 1.11 1.11 1.11 16.4 1.70 1.91 3.1 3.36 3.9 4.41 4.41.16.174 6.31 6.3 6.476 6.41 6.66 6.67 6.09 6.1 6.39 6.910 6.93 7.36 7.37 7.47 7.14 7.934 7.96 13 1 11 10 9 7 6 4 3 1 0 ppm S1: 1 -NMR (400 Mz, DMS-d6) Spectrum of Compound 1 Kedi Nanesi yeni kolon fr 114 coken 3''' 1''' '' '' '' 1'' 7''' 1 7 6 4 3

1.47 14.37 17.347 160.40 161.604 161.3 163.149 164.700 166.9 9.133 99.90 103.463 10. 114.19 116.103 116.434 11.419 1.39 1.976 130.9 63.3 6.3 70.409 73.390 74.7 74.70 76.6 7''' '' 3''' 1''' '' 1'' '' 1 7 6 4 3 00 10 160 140 10 100 0 60 40 0 0 ppm S: 13 C-NMR (100 Mz, DMS-d6) Spectrum of compound 1

3''' 1''' 7''' '' '' 1'' '' 7 6 1 14.3 4 3 130.43 1.91 116.49 116.09 114.141 103.44 99.9 9.116 76.66 74. 73.37 70.34 NAME Kedi Nanesi yeni kolon fr 114 coken EXPN 3 PRCN 1 Date_ 01017 Time 1.4 INSTRUM spect PRBD mm DUL 13C-1 PULPRG dept90 TD 636 SLVENT DMS NS 471 DS 4 SW 403.461 z FIDRES 0.36679 z AQ 1.36319 sec RG 00 DW 0.00 usec DE 6.0 usec TE 300.0 K CNST 14.0000000 D1.00000000 sec D 0.00344 sec D1 0.0000000 sec TD0 1 ======== CANNEL f1 ======== NUC1 13C P1 9.00 usec P 1.00 usec PL1-1.00 db PL1W 46.169430 W SF1 100.69 Mz ======== CANNEL f ======== CPDPRG waltz16 NUC 1 P3 10.0 usec P4 0.40 usec PCPD 0.00 usec PL -3.11 db PL1 1.00 db PLW 19.14317 W PL1W 0.94901 W SF 400.131600 Mz SI 376 SF 100.617690 Mz WDW EM SSB 0 LB 1.00 z GB 0 PC 1.40 00 10 160 140 10 100 0 60 40 0 0 ppm S3: DEPT-90 (100 Mz, DMS-d6) Spectrum of compound 1

116.49 116.09 114.141 3''' 1''' '' 7''' '' 1'' '' 7 1 6 103.44 99.9 3 4 9.116 76.66 74. 73.37 70.34 NAME Kedi Nanesi yeni kolon fr 114 coken EXPN 3 PRCN 1 Date_ 01017 Time 1.4 INSTRUM spect PRBD mm DUL 13C-1 PULPRG dept90 TD 636 SLVENT DMS NS 471 DS 4 SW 403.461 z FIDRES 0.36679 z AQ 1.36319 sec RG 00 DW 0.00 usec DE 6.0 usec TE 300.0 K CNST 14.0000000 D1.00000000 sec D 0.00344 sec D1 0.0000000 sec TD0 1 ======== CANNEL f1 ======== NUC1 13C P1 9.00 usec P 1.00 usec PL1-1.00 db PL1W 46.169430 W SF1 100.69 Mz ======== CANNEL f ======== CPDPRG waltz16 NUC 1 P3 10.0 usec P4 0.40 usec PCPD 0.00 usec PL -3.11 db PL1 1.00 db PLW 19.14317 W PL1W 0.94901 W SF 400.131600 Mz SI 376 SF 100.617690 Mz WDW EM SSB 0 LB 1.00 z GB 0 PC 1.40 10 11 110 10 100 9 90 0 7 ppm S4: DEPT-90 (100 Mz, DMS-d6) Spectrum of compound 1(Expanded)

1.44 14.374 17.34 160.41 161.607 161.30 163.11 164.70 166.94 114.166 116.436 11.4 1.334 1.973 9.13 99.930 103.466 10.6 63.79 70.40 73.399 74.7 76.67 7''' '' 3''' 1''' '' 1'' '' 1 7 6 4 3 00 190 10 170 160 10 140 130 10 110 100 90 0 70 60 0 40 30 0 10 ppm S: APT (100 Mz, DMS-d6) Spectrum of compound 1

ppm 0. 1.0 1..0. 3.0 3. 4.0 4..0. 6.0 6. 7.0 7..0 13 130 1 10 11 110 10 100 9 90 0 7 70 6 60 0 4 40 3 30 0 1 10 ppm S6: ETCR (400 Mz, DMS-d6) Spectrum of compound 1

ppm '' 3''' 1''' 7''' '' 1'' '' 7 1 1 6 4 3 3 4 6 7 9 9.0..0 7. 7.0 6. 6.0..0 4. 4.0 3. 3.0..0 1. 1.0 0. ppm S7: CSY-90 (400 Mz, DMS-d6) Spectrum of compound 1

ppm 3''' '' 7''' 0 1''' '' 1'' '' 7 6 1 4 3 40 60 0 100 10 140 160 10 9.0..0 7. 7.0 6. 6.0..0 4. 4.0 3. 3.0..0 1. 1.0 0. ppm S: MBC (400 Mz, DMS-d6) Spectrum of compound 1

3''' '' 7''' 1''' '' 1'' '' 7 1 6 4 3 S9: PLC-QTF Spectrum of compound 1

1.13.00.0.0 1.10 1.36 1. 1.4 1.07 3.71 1. 3.99 1.44 1.9 0.3 1.94 6.41 6.40 6.77 6.93 6.96 6.993 7.9 7.976 3.171 3.07 3.4 3.69 3.91 3.314 3.70 3.73 4.01 4.036.06.00 '' '' 1'' 7 4 3 1 ' 13 1 11 10 9 7 6 4 3 1 0 ppm S10: 1 -NMR (400 Mz, DMS-d6) Spectrum of Compound

1.13.00.0.0 1.10 1.36 1. 1.4 1.07 3.71 1. 3.99 1.44 1.9 0.3 1.94 6.41 6.40 6.77 6.93 6.96 6.993 7.9 7.976 3.171 3.07 3.4 3.69 3.91 3.314 3.70 3.73 4.01 4.036.06.00 '' '' 1'' 7 4 3 1 '.0 7. 7.6 7.4 7. 7.0 ppm 13 1 11 10 9 7 6 4 3 1 0 ppm S11: 1 -NMR (400 Mz, DMS-d6) Spectrum of Compound (Expanded)

1.464 17.404 161.63 161.7 163.40 164.744 19.07 116.479 11.434 9.91 99.976 100.346 103.30 10.791 60.4 61.01 69.99 73.41 76.63 77.611 '' '' 1'' 7 4 3 1 ' 00 10 160 140 10 100 0 60 40 0 0 ppm S1: 13 C-NMR (100 Mz, DMS-d6) Spectrum of Compound

1.463 '' 164.746 163.40 161.70 161.63 17.404 1'' '' 7 19.077 11.43 116.40 10.796 103.34 100.3 99.90 9.97 7.99 77.614 76.67 73.46 70.007 67.66 67.647 63.31 61.07 60.39 4 3 1 ' NAME sakine kolon 1-16 fr cokelek EXPN 3 PRCN 1 Date_ 01117 Time 4.17 INSTRUM spect PRBD mm DUL 13C-1 PULPRG jmod TD 636 SLVENT DMS NS 307 DS 4 SW 403.461 z FIDRES 0.36679 z AQ 1.36319 sec RG 00 DW 0.00 usec DE 6.0 usec TE 300.0 K CNST 14.0000000 CNST11 1.0000000 D1.00000000 sec D0 0.00696 sec TD0 1 ======== CANNEL f1 ======== NUC1 13C P1 9.00 usec P 1.00 usec PL1-1.00 db PL1W 46.169430 W SF1 100.69 Mz ======== CANNEL f ======== CPDPRG waltz16 NUC 1 PCPD 0.00 usec PL -3.11 db PL1 1.00 db PLW 19.14317 W PL1W 0.94901 W SF 400.131600 Mz SI 376 SF 100.617690 Mz WDW EM SSB 0 LB 1.00 z GB 0 PC 1.40 00 10 160 140 10 100 0 60 40 0 ppm S13: APT (100 Mz, DMS-d6) Spectrum of Compound

'' 1'' '' 7 1 ' 4 3 S14: ETCR (100 Mz, DMS-d6) Spectrum of Compound

'' 1'' '' 7 1 ' 4 3 S1: PLC-QTF Spectrum of Compound

1.07 0.94 1.1 1.11 1.01 0.9 3.00 6.03 6.07 7.374 7.3 7.400 7.419 7.637 7.69 7.66 7.7 7.76 7.740 7.743 7.761 7.76 7.96 7.94.17.176.19.196 3.11 3 N..0 7. 7.6 ppm 6.10 6.0 ppm 11 10 9 7 6 4 3 1 0 S16: 1 -NMR (400 Mz, DMS-d6) Spectrum of Compound 3 sakine tohum kolon 34-3

3 N S17: 13 C-NMR, DEPT-90, DEPT-13 (100 Mz, DMS-d6) Spectrum of Compound 3

ETCR.ESP F Chemical Shift (ppm) 144 136 1 10 11 104 96 0 7 64 6 4 40 0. 1.0 1. F1 Chemical Shift (ppm).0. 3.0 3. 4.0 4. 3 N.0. 6.0 6. 7.0 7..0. S1:ETCR (400 Mz, DMS-d6) Spectrum of Compound 3

S19: DPP free radical scavenging activity of standards, compounds and extracts

S0: ABTS + scavenging activity of standards, compounds and extracts

S1: Reducing power activity of standard, compounds and extracts

S: Total phenolic compounds

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) 164.7 164.7 3 103. 6.3 s -3/C-, 4, 10, 1' 3 103. 6.9 s 4 1.4 4 1. 161. 13.0 s 163.4 13 s 6 99.9 6.47 (d, J=.1) -6/C-7, 6 9.3 6.4 brs 7 163. 7 161.6 9.1 6.1 (d, J=.1) -/C-6, 7, 9, 10 100.0 6.46 (d, J= 1.) 9 17.3 9 17.4 10 10. 10 10. 1' 11.4 1' 11.4 ', 6' 19.0 7.94 (d, J=.) -', 6'/C-, ', 6' 19.1 7.96 (d, J =.4) 3', ' 116. 6.9 (d, J=.) -3', '/ C-1', 3', ' 116. 6.97 (d, J =.4) 161.6 161.9 Glucose 1'' 99.9.16 (d, J = 7.3) -1''/C-7 1'' 100.3.06 (d, J = 7.0) '' 73.4 3.33 (t, J = 7.3) '' 73. 3.7 (t, J = 7.0) 3'' 76.7 3.34 m 3'' 76.9 3.30 m ' 70.4 3.1 m ' 70.0 3.1 m '' 74.3 3.3 m '' 77.6 3.44 m a 63.9 3.46 m a 61.1 3.4 m b 61.1 4.19 m b 61.1 3.7 m - 13.0 s - 13.0-10.4 s - 10.4 coumaroyl 1''' 166.9 ''' 114. 7.49 (d, J = 1.) -"'/C-1''', 3"', 3''' 14.4 6.33 (d, J = 1.) -3"'/C-"', 4"' '' 1.3 ''', 9"' 116.1 6.66 (d, J =.6) -"', 9"'/C-4"', 6"', "', 7"' ', "' 130. 7.36 (d, J=.6) -6"', "'/C-"', 9"', 7"', 4"' 7''' 160.

Table. Carbon and proton data of 1-methylquinolin-4(1)-one (3 ) C/ δ C ppm δ (J z) MBC ( C) 14. 7.9 (d,j=.0) -/C-3, 4,10 3 109.9 6.0 (d, J =.0) -3/C-, 4, 9 4 176.9 117.1 7.6(d, J =.0) -/C-6, 7 6 14.0 7.40 (t, J =.0) -6/C-, 7, 7 13. 7.74 (ddd, J =.0, 1.6) -7/C-6, 1.9.19 (dd, J =.0, 1.6) -/C-4, 6, 7, 10 9 17.0 10 141.0 C 3 40.6 3.7 s