Chemical Constituents and Antioxidant Activity of Teucrium barbeyanum Aschers.
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1 Supporting Information Rec. Nat. Prod. 9:1 (2015) Chemical Constituents and Antioxidant Activity of Teucrium barbeyanum Aschers. Mohamed Ali A. Alwahsh, Melati Khairuddean * and Wong Keng Chong School of Chemical Sciences, Universiti Sains Malaysia, 11800, Penang, Malaysia Table of Contents Page S1: 1 H NMR (CDCl 3, 500 MHz) spectrum of compound 1 (5-hydroxy- 3,6,7,4 -tetramethoxyflavone) 3 S2: 13 C NMR (CDCl 3, 125 MHz) spectrum of compound 1 4 S3: (a) DEPT 135 and (b) DEPT 90 NMR (CDCl 3, 125 MHz) spectra of compound 1 4 S4: 1 H NMR (CDCl 3, 500 MHz) spectrum of compound 2 (Salvigenin) 5 S5: 13 C NMR (CDCl 3, 125 MHz) spectrum of compound 2 6 S6: (a) DEPT 135 and (b) DEPT 90 NMR (CDCl 3, 125 MHz) spectra of compound 2 6 S7: 1 H NMR (CDCl 3, 500 MHz) spectrum of compound 3 7 (5-hydroxy-6,7,3,4 -tetramethoxyflavone) S8: 13 C NMR (CDCl 3, 125 MHz) spectrum of compound 3 8 S9: (a) DEPT 135 and (b) DEPT 90 NMR (CDCl 3, 125 MHz) spectra of compound 3 8 S10: 1 H NMR (Acetone-d 6, 500 MHz) spectrum of compound 4 (Chrysosplenetin) 9 S11: 13 C NMR (Acetone-d 6, 125 MHz) spectrum of compound 4 10 S12: (a) DEPT 135 and (b) DEPT 90 NMR (Acetone-d 6, 125 MHz) spectra of 10 compound 4 * Corresponding author: melati@usm.my; Phone: Fax:
2 S13: 1 H NMR (Acetone-d 6, 500 MHz) spectrum of compound 5 (Cirsilineol) 11 S14: 13 C NMR (Acetone-d 6, 125 MHz) spectrum of compound 5 12 S15: (a) DEPT 135 and (b) DEPT 90 NMR (Acetone-d 6, 125 MHz) spectra of 12 compound 5 S16: 1 H NMR (DMSO-d 6, 500 MHz) spectrum of compound 6 (Cirsimaritin) 13 S17: 13 C NMR (DMSO-d 6, 125 MHz) spectrum of compound 6 14 S18: (a) DEPT 135 and (b) DEPT 90 NMR (DMSO-d 6, 125 MHz) spectra of 14 compound 6 S19: 1 H NMR (DMSO-d 6, 500 MHz) spectrum of compound 7 (Cirsiliol) 15 S20: 13 C NMR (DMSO-d 6, 125 MHz) spectrum of compound 7 16 S21: (a) DEPT 135 and (b) DEPT 90 NMR (DMSO-d 6, 125 MHz) spectra of 16 compound 7 S22: 1 H NMR (DMSO-d 6, 500 MHz) spectrum of compound 8 (Apigenin) 17 S23: 13 C NMR (DMSO-d 6, 125 MHz) spectrum of compound 8 18 S24: (a) DEPT 135 and (b) DEPT 90 NMR (DMSO-d 6, 125 MHz) spectra of 18 compound 8 S25: 1 H NMR (DMSO-d 6, 500 MHz) spectrum of compound 9 (Luteolin) 19 S26: 13 C NMR (DMSO-d 6, 125 MHz) spectrum of compound 9 20 S27: (a) DEPT 135 and (b) DEPT 90 NMR (DMSO-d 6, 125 MHz) spectra of 20 compound 9 S28: 1 H NMR (acetone-d 6, 500 MHz) spectrum of compound 10 (methyl caffeate) 21 S29: (a) 13 C, (b) DEPT 135 and (c) DEPT 90 NMR (acetone-d 6, 125 MHz) 22 spectra of compound 10 S30: (a) 1 H, (b) 13 C and (c) DEPT 90 NMR (acetone-d 6, 500/125 MHz) 23 spectra of compound 11 (4-hydroxybenzaoic acid) S31: Inhibition effect at various concentrations of extracts and standards (trolox, 24 gallic acid and ascorbic acid) on DPPH radical. S32: Inhibition effect at various concentrations of extracts and standards (trolox, 24 gallic acid and luteolin) on ABTS radical. Table S33: Correlation (Pearson s correlation coefficients). 25 2
3 H 3 CO H 3 CO 6 7 3' 2' 4' 8 1' 9 O 2 5' 6' OCH 3 OH O OCH 3 S1: 1 H NMR (CDCl 3, 500 MHz) spectrum of compound 1 (5-hydroxy-3,6,7,4 - tetramethoxyflavone) Compound 1 (5-hydroxy-3,6,7,4 -tetramethoxyflavone), yellow wax: -ESI-MS m/z: [M H] ; UVλ max (nm): (MeOH) 234 (sh), 273, 335, (NaOMe) 291, 366 (sh), (AlCl 3 ) 233 (sh), 283, 299 (sh), 363, (AlCl 3 /HCl) 235, 285, 299 (sh), 357, (NaOAc) 294, 320 (sh), (NaOAc/H 3 BO 3 ) 272, 336; 1 H NMR (500 MHz, CDCl 3 ): δ (s, 1 H, 5-OH), 8.04 (d, J = 9.0 Hz, 2 H, H-2, 6 ), 7.00 (d, J = 9.0 Hz, 2 H, H-3, 5 ), 6.47 (s, 1 H, H-8), 3.93 (s, 3 H, 7-OMe), 3.89 (s, 3 H, 6-OMe), 3.87 (s, 3 H, 4 -OMe), 3.83 (s, 3 H, 3-OMe); 13 C NMR (125 MHz, CDCl 3 ): δ (C-4), (C-4 ), (C-7), (C-2), (C-5), (C-9), (C-3), (C-6), (C-2, 6 ), (C-1 ), (C-3, 5 ), (C-10), (C-8), (6-OMe), (3-OMe), (4 -OMe), (7-OMe). 3
4 S2: 13 C NMR (CDCl 3, 125 MHz) spectrum of compound 1 (5-hydroxy-3,6,7,4 - tetramethoxyflavone) S3: (a) DEPT 135 and (b) DEPT 90 NMR (CDCl 3, 125 MHz) spectra of compound 1 (5- hydroxy-3,6,7,4 -tetramethoxyflavone) 4
5 H 3 CO H 3 CO O OH O 2' 1' 2 3 3' 6' 4' 5' OCH 3 S4: 1 H NMR (CDCl 3, 500 MHz) spectrum of compound 2 (Salvigenin) Compound 2 (Salvigenin), yellow wax: -ESI-MS m/z: [M H] ; UV λ max (nm): (MeOH) 275, 333, (NaOMe) 295, 369 (sh), (AlCl 3 ) 263, 289 (sh), 301, 357, (AlCl 3 /HCl) 261, 289 (sh), 300, 354, (NaOAc) 280, 328, (NaOAc/H 3 BO 3 ) 275, 332; 1 H NMR (500 MHz, CDCyl 3 ): δ (s, 1 H, 5-OH), 7.82 (d, J = 8.9 Hz, 2 H, H-2, 6 ), 6.99 (d, J = 8.9 Hz, 2 H, H-3, 5 ), 6.57 (s, 1 H, H-3), 6.52 (s, 1 H, H-8) 3.95 (s, 3 H, 7-OMe), 3.90 (s, 3 H, 6-OMe), 3.87 (s, 3 H, 4 -OMe); 13 C NMR (125 MHz, CDCl 3 ): δ (C-4), (C-2), (C-4 ), (C-7), (C-9), (C-5), (C-6), (C-2, 6 ), (C-1 ), (C- 3, 5 ), (C-10), (C-3), (C-8), (6-OMe), (7-OMe), (4 - OMe). 5
6 S5: 13 C NMR (CDCl 3, 125 MHz) spectrum of compound 2 (Salvigenin) S6: (a) DEPT 135 and (b) DEPT 90 NMR (CDCl 3, 125 MHz) spectra of compound 2 (Salvigenin) 6
7 H 3 CO H 3 CO O OH O 2' 1' 2 3 OCH 3 3' OCH 3 4' 5' 6' S7: 1 H NMR (CDCl 3, 500 MHz) spectrum of compound 3 (5-hydroxy-6,7,3,4 - tetramethoxyflavone) Compound 3 (5-hydroxy-6,7,3,4 -tetramethoxyflavone), yellow needles: -ESI-MS m/z: [M H] ; UV λ max (nm): (MeOH) 276, 337, (NaOMe) 291, 371 (sh), (AlCl 3 ) 257 (sh), 285, 364, (AlCl 3 /HCl) 257 (sh), 287, 359, (NaOAc) 282, 325, (NaOAc/H 3 BO 3 ) 275, 338; 1 H NMR (500 MHz, acetone-d 6 ): δ (s, 1 H, 5-OH), 7.71 (dd, J = 8.5, 2.2 Hz, 1 H, H-6 ), 7.63 (d, J = 2.2 Hz, 1 H, H-2 ), 7.15 (d, J = 8.5 Hz, 1 H, H-5 ), 6.87 (s, 1 H, H-8), 6.78 (s, 1 H, H-3), 3.98 (s, 1 H, 7-OMe), 3.96 (s, 1 H, 3 -OMe), 3.93 (s, 1 H, 4 -OMe), 3.80 (s, 1 H, 6- OMe); 13 C NMR (125 MHz, acetone-d 6 ): δ (C-4), (C-2), (C-7), (C-5), (C-9), (C-4 ), (C-3 ), (C-6), (C-1 ), (C-6 ), (C-5 ), (C-2 ), (C-10), (C-3), (C-8), (6-OMe), (7-OMe), (3 -OMe), (4 -OMe). 7
8 S8: 13 C NMR (CDCl 3, 125 MHz) spectrum of compound 3 (5-hydroxy-6,7,3,4 - tetramethoxyflavone) S9: (a) DEPT 135 and (b) DEPT 90 NMR (CDCl 3, 125 MHz) spectra of compound 3 (5- hydroxy-6,7,3,4 -tetramethoxyflavone) 8
9 H 3 CO H 3 CO ' 9 O 1' 2 6' OCH 3 OH O OCH 3 3' OH 4' 5' S10: 1 H NMR (Acetone-d 6, 500 MHz) spectrum of compound 4 (Chrysosplenetin) Compound 4 (Chrysosplenetin), yellow solid: EI-MS m/z: [M] + ; UV λ max (nm): (MeOH) 257, 269 (sh), 351, (NaOMe) 268, 405, (AlCl 3 ) 268, 379, (AlCl 3 /HCl) 265, 279 (sh), 366, (NaOAc) 268, 292 (sh), 413, (NaOAc/H 3 BO 3 ) 257, 268 (sh), 354; 1 H NMR (500 MHz, acetone-d 6 ): δ (s, 1 H, 5-OH), 7.80 (d, J = 2.0 Hz, 1 H, H-2 ), 7.72 (dd, J = 2.0, 8.5 Hz, 1 H, H-6 ), 7.01 (d, J = 8.5 Hz, 1 H, H-5 ), 6.82 (s, 1 H, H-8), 3.97 (s, 3 H, 7-OMe), 3.94 (s, 3 H, 3 -OMe), 3.90 (s, 3 H, 3-OMe), 3.80 (s, 3 H, 6-OMe); 13 C NMR (125 MHz, acetone-d 6 ): δ (C-4), (C-2), (C-7), (C-5), (C-9), (C-4 ), (C-3 ), (C-3), (C-6), (C-6 ), (C-1 ), (C-5 ), (C-2 ), (C-10), (C-8), (6-OMe), (3-OMe), (7-OMe), (3 -OMe). 9
10 S11: 13 C NMR (Acetone-d 6, 125 MHz) spectrum of compound 4 (Chrysosplenetin) S12: (a) DEPT 135 and (b) DEPT 90 NMR (Acetone-d 6, 125 MHz) spectra of compound 4 (Chrysosplenetin) 10
11 H 3 CO H 3 CO O OH O 2' 1' 2 3 OCH 3 3' OH 4' 5' 6' S13: 1 H NMR (Acetone-d 6, 500 MHz) spectrum of compound 5 (Cirsilineol) Compound 5 (Cirsilineol), yellow amorphous: EI-MS m/z: [M] + ; UV λ max (nm): (MeOH) 241, 275, 343, (NaOMe) 266, 402, (AlCl 3 ) 261, 285, 373, (AlCl 3 /HCl) 259, 289, 365, (NaOAc) 271, 416, (NaOAc/H 3 BO 3 ) 275, 347; 1 H NMR (500 MHz, acetone-d 6 ): δ (s, 1 H, 5-OH), 7.63 (m, 2 H, H-2, 6 ), 7.08 (d, J = 8.2 Hz, 1 H, H-5 ), 6.84 (s, 1 H, H-8), 6.74 (s, 1 H, H-3), 3.99 (s, 3 H, 3 -OMe), 3.97 (s, 3 H, 7-OMe), 3.80 (s, 3 H, 6-OMe); 13 C NMR (125 MHz, acetone-d 6 ): δ (C-4), (C-2), (C-7), (C-5), (C- 9), (C-4 ), (C-3 ), (C-6), (C-1 ), (C-6 ), (C-5 ), (C-2 ), (C-10), (C-3), (C-8), (6-OMe), (7-OMe), (3 -OMe). 11
12 S14: 13 C NMR (Acetone-d 6, 125 MHz) spectrum of compound 5 (Cirsilineol) S15: (a) DEPT 135 and (b) DEPT 90 NMR (Acetone-d 6, 125 MHz) spectra of compound 5 (Cirsilineol) 12
13 H 3 CO H 3 CO O OH O 2' 1' 2 3 3' 6' 4' 5' OH S16: 1 H NMR (DMSO-d 6, 500 MHz) spectrum of compound 6 (Cirsimaritin) Compound 6 (Cirsimaritin), yellow crystal: EI-MS m/z: [M] + ; UV λ max (nm): (MeOH) 276, 332, (NaOMe) 274, 383, (AlCl 3 ) 265 (sh), 290 (sh), 301, 361, (AlCl 3 /HCl) 265 (sh), 290 (sh), 300, 354, (NaOAc) 273, 388, (NaOAc/H 3 BO 3 ) 275, 337; 1 H NMR (500 MHz, acetoned 6 ): δ (s, 1 H, 5-OH), 7.95 (d, J = 8.8 Hz, 2 H, H-2, 6 ), 7.02 (d, J = 8.8 Hz, 2 H, H-3, 5 ), 6.85 (s, 1 H, H-8), 6.68 (s, 1 H, H-3), 3.98 (s, 3 H, 7-OMe), 3.79 (s, 3 H, 6-OMe); 13 C NMR (125 MHz, acetone-d 6 ): δ (C-4), (C-2), (C-4 ) (C-7), (C-9), (C-5), (C-6), (C-2, 6 ), (C-1 ), (C-3, 5 ), (C-10), (C-3), (C-8), (6-OMe), (7-OMe). 13
14 S17: 13 C NMR (DMSO-d 6, 125 MHz) spectrum of compound 6 (Cirsimaritin) S18: (a) DEPT 135 and (b) DEPT 90 NMR (DMSO-d 6, 125 MHz) spectra of compound 6 (Cirsimaritin) 14
15 H 3 CO H 3 CO O OH O 2' 1' 2 3 OH 3' 6' 4' 5' OH S19: 1 H NMR (DMSO-d 6, 500 MHz) spectrum of compound 7 (Cirsiliol) Compound 7 (Cirsiliol), yellow powder: EI-MS m/z: [M] + ; UV λ max (nm): (MeOH) 255, 273, 345, (NaOMe) 239 (sh), 268, 400, (AlCl 3 ) 240 (sh), 275, 300 (sh), 342 (sh), 423, (AlCl 3 /HCl) 262, 284, 366, (NaOAc) 269, 402, (NaOAc/H 3 BO 3 ) 263, 370; 1 H NMR (500 MHz, acetone-d 6 ): δ (s, 1 H, 5-OH), 7.45 (m, 2 H, H-2, 6 ), 6.91 (d, J = 8.8 Hz, 1 H, H- 5 ), 6.87 (s, 1 H, H-8), 6.73 (s, 1 H, H-3),3.93 (s, 3 H, 7-OMe), 3.74 (s, 3 H, 6-OMe); 13 C NMR (125 MHz, DMSO-d 6 ): δ (C-4), (C-2), (C-7), (C-9), (C-5), (C-4 ), (C-3 ), (C-6), (C-1 ), (C-6 ), (C-5 ), (C-2 ), (C-10), (C-3), (C-8), (6-OMe), (7- OMe). 15
16 S20: 13 C NMR (DMSO-d 6, 125 MHz) spectrum of compound 7 (Cirsiliol) S21: (a) DEPT 135 and (b) DEPT 90 NMR (DMSO-d 6, 125 MHz) spectra of compound 7 (Cirsiliol) 16
17 HO O OH O 2' 1' 2 3 3' 6' 4' 5' OH S22: 1 H NMR (DMSO-d 6, 500 MHz) spectrum of compound 8 (Apigenin) Compound 8 (Apigenin), yellow powder: EI-MS m/z: [M] + ; UV λ max (nm): (MeOH) 268, 336, (NaOMe) 275, 325, 393, (AlCl 3 ) 275, 302, 349, 379, (AlCl 3 /HCl) 277, 300, 340, 374, (NaOAc) 275, 312, 389, (NaOAc/H 3 BO 3 ) 269, 343; 1 H NMR (500 MHz, DMSO-d 6 ): δ (s, 1 H, 5-OH), 7.93 (d, J = 8.8 Hz, 2 H, H-2, 6 ), 6.93 (d, J = 8.8 Hz, 2 H, H-3, 5 ), 6.78 (s, 1 H, H-3), 6.48 (d, J = 2.0 Hz, 1 H, H-8), 6.19 (d, J = 2.0 Hz,1 H, H-6); 13 C NMR (125 MHz, DMSO-d 6 ): δ (C-4), (C-7), (C-2), (C-5), (C- 4 ), (C-9), (C-2, 6 ), (C-1 ), (C-3, 5 ), (C-10), (C-3), (C-6), (C-8). 17
18 S23: 13 C NMR (DMSO-d 6, 125 MHz) spectrum of compound 8 (Apigenin) S24: (a) DEPT 135 and (b) DEPT 90 NMR (DMSO-d 6, 125 MHz) spectra of compound 8 (Apigenin) 18
19 HO OH O 4 O 2' 1' 2 3 OH 3' 6' 4' 5' OH S25: 1 H NMR (DMSO-d 6, 500 MHz) spectrum of compound 9 (Luteolin) Compound 9 (Luteolin), yellow powder: EI-MS m/z: [M] + ; UV λ max (nm): (MeOH) 254, 265, 295 (sh), 348, (NaOMe) 267, 333, 403, (AlCl 3 ) 273, 300 (sh), 333, 424, (AlCl 3 /HCl) 263, 275, 295 (sh), 357, 381, (NaOAc) 270, 326, 399, (NaOAc/H 3 BO 3 ) 262, 300 (sh), 374, 422 (sh); 1 H NMR (500 MHz, DMSO-d 6 ): δ (s, 1 H, 5-OH), 7.42 (m, 2 H, H- 2, 6 ), 6.90 (d, J = 8.0 Hz, 1 H, H-5 ), 6.67 (s, 1 H, H-3), 6.45 (d, J = 2.0 Hz, 1 H, H-8), 6.19 (d, J = 2.0 Hz, 1 H, H-6); 13 C NMR (125 MHz, DMSO-d 6 ): δ (C-4), (C-7), (C-2), (C-5), (C-9), (C-4 ), (C-3 ), (C-1 ), (C-6 ), (C-5 ), (C-2 ), (C-10), (C-3), (C-6), (C-8). 19
20 S26: 13 C NMR (DMSO-d 6, 125 MHz) spectrum of compound 9 (Luteolin) S27: (a) DEPT 135 and (b) DEPT 90 NMR (DMSO-d 6, 125 MHz) spectra of compound 9 (Luteolin) 20
21 2 HO 3 1 HO ' 2' O OCH 3 S28: 1 H NMR (acetone-d 6, 500 MHz) spectrum of compound 10 (methyl caffeate) Compound 10 (methyl caffeate), brown solid: EI-MS m/z: [M] + ; 1 H NMR (500 MHz, DMSO-d 6 ): δ 7.54 (d, J = 15.9 Hz, 1 H, H-1 ), 7.17 (d, J = 2.0 Hz, 1 H, H-2), 7.03 (dd, J = 8.2, 2.0 Hz, 1 H, H-6), 6.87 (d, J = 8.2 Hz, 1 H, H-5), 6.29 (d, J = 15.9 Hz, 1 H, H-2 ), 3.73 (s, 3 H, -OMe); 13 C NMR (125 MHz, DMSO-d 6 ): δ (CO), (C-4), ), (C-3), (C-1 ), (C-1), (C-6), (C-5), (C-2), (C-2 ), (- OMe). 21
22 S29: (a) 13 C, (b) DEPT 135 and (c) DEPT 90 NMR (acetone-d 6, 125 MHz) spectra of compound 10 (methyl caffeate) 22
23 O OH OH 6 5 S30: (a) 1 H, (b) 13 C and (c) DEPT 90 NMR (acetone-d 6, 500/125 MHz) spectra of compound 11 (4-hydroxybenzaoic acid) Compound 11 (4-hydroxybenzaoic acid), brown solid: -ESI-MS m/z: [M H] ; 1 H NMR (500 MHz, acetone-d 6 ): δ 7.91 (d, J = 8.7 Hz, 2 H, H-2, 6), 6.91 (d, J = 8.7 Hz, 2 H, H-3, 5); 13 C NMR (125 MHz, DMSO-d 6 ): δ (CO), (C-4), (C-2, 6), (C-1), (C-3, 5). 23
24 S31: Inhibition effect at various concentrations of extracts and standards (trolox, gallic acid and ascorbic acid) on DPPH radical. S32: Inhibition effect at various concentrations of extracts and standards (trolox, gallic acid and luteolin) on ABTS radical. 24
25 Table S33: Correlation (Pearson s correlation coefficients). Extract TFC (QE) DPPH (IC 50 ) ABTS (TEAC) ABTS (IC 50 ) FRAP (TE) TPC (GAE) TFC (QE) DPPH (IC 50 ) ABTS (TEAC) ABTS (IC 50 ) Correlation is significant at the 0.01 level. 25
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