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. 2022 Dec 14;70(51):16241–16252. doi: 10.1021/acs.jafc.2c07457

Table 2. Spectral Data and (Tentative) Identifications of Hydroxycinnamoylagmatine Oxidative Coupling Products after 120 min of Incubation with HRP on a Small Scaled.

  UHPLC-PDA-ESI-IT-MS
 ESI-FT-MS
  
compound RT (min) λmax (nm) ionization m/z MS2 (m/z) (relative abundance)a molecular formula calculated m/z observed m/z error (ppm) annotation
CouAgm
2 6.27 n.d. [M + H]+ 277 260 (100), 235 (41), 114 (24), 217 (20) C14H20O2N4 277.16590 277.16565 –0.91 cis-CouAgmb
3 6.74 318 [M + 2H]2+ 276 421 (100), 131 (90), 234 (79), 211 (76), 114 (72), 404 (53), 246 (53), 362 (46), 230 (30), 361 (28), 422 (26), 255 (23), 267 (20), 157 (20), 534 (18), 405 (15), 231 (15) C28H38O4N8 276.15808 276.15771 –1.33 CouAgm-8-8′-DCouAgmb
5 9.55 294 [M + H]+ 277 260 (100), 114 (17), 217 (17), 115 (12), 235 (10) C14H20O2N4 277.16590 277.16568 –0.81 trans-CouAgmc
6 11.09 318 [M + 2H]2+ 276 246 (100), 267 (29), 234 (11), 260 (5), 534 (3), 157 (3), 421 (2), 211 (2), 114 (2), 131 (2) C28H38O4N8 276.15808 276.15793 0.53 CouAgm-8-8′/9-N-7′-DCouAgmb
9 19.69 310 [M + 2H]2+ 276 395 (100), 246 (90), 267 (79), 157 (24), 396 (24), 98 (19), 421 (17), 291 (12), 131 (12), 114 (12), 97 (11), 420 (11), 534 (5), 211 (3) C28H38O4N8 276.15808 276.15814 0.23 CouAgm-4-O-7′/3-8′-DCouAgmc
10 19.97 318 [M + 2H]2+ 276 395 (100), 246 (100), 267 (91), 157 (24), 396 (24), 98 (17), 421 (17), 97 (13), 291 (12), 255 (12), 131 (10), 114 (9), 534 (4) C28H38O4N8 276.15808 276.15808 –0.01 CouAgm-4-O-7′/3-8′-DCouAgmb
11 20.50 250 [M + 2H]2+ 276 246 (100), 267 (51), 211 (4), 421 (4), 395 (1), 114 (1) C28H38O4N8 276.15808 276.15802 –0.21 CouAgm-4-O-8′-CouAgmb
FerAgm
12 10.25 334 [M + 2H]2+ 306 131 (100), 241 (99), 481 (78), 114 (61), 297 (41), 157 (39), 464 (36), 276 (31), 323 (31), 422 (29), 227 (27), 482 (26), 285 (26), 179 (25), 298 (22), 421 (17), 594 (16), 436 (14), 465 (11), 351 (10) C30H42O6N8 306.16864 306.16864 –0.20 FerAgm-8-8′-FerAgmc
13 10.38 334 [M + 2H]2+ 306 131 (100), 481 (60), 464 (58), 241 (42), 114 (39), 297 (37), 157 (29), 227 (25), 422 (23), 323 (22), 436 (21), 594 (17), 285 (17), 465 (17), 340 (16), 482 (16), 298 (16), 276 (12), 439 (12), 331 (10) C30H42O6N8 306.16864 306.16840 –0.79 FerAgm-2-7′/8–8′-DFerAgmc
14 12.25 318 [M + H]+ 307 290 (100), 177 (22), 114 (18), 247 (14) C15H22O3N4 307.17647 307.17633 –0.45 trans-FerAgmc
16 14.07 n.d. [M + 2H]2+ 306 276 (100), 297 (32), 285 (11), 131 (10), 157 (7), 481 (6), 241 (6), 114 (5), 594 (4), 290 (4) C30H42O6N8 306.16864 306.16861 –0.10 FerAgm-8-8′/9-N-7′-DFerAgmb
18 21.06 322 [M + 2H]2+ 306 455 (100), 297 (55), 276 (49), 157 (44), 481 (27), 456 (27), 131 (16), 351 (12), 114 (10) C30H42O6N8 306.16864 306.16870 0.19 FerAgm-4-O-7′/3-8′-DFerAgmc
20 22.01 322 [M + 2H]2+ 306 455 (100), 297 (53), 276 (51), 157 (44), 456 (25), 481 (24), 131 (15), 351 (9), 114 (8) C30H42O6N8 306.16864 306.16855 –0.30 FerAgm-4-O-7′/3-8′-DFerAgmb
21 23.26 326 [M + 2H]2+ 306 276 (100), 297 (48), 289 (14), 481 (4), 241 (2), 455 (2), 114 (1), 290 (1) C30H42O6N8 306.16864 306.16855 –0.30 FerAgm-4-O-8′-FerAgmc
SinAgm
25 8.87 330 [M + 2H]2+ 336 131 (100), 361 (99), 157 (64), 328 (60), 383 (57), 306 (57), 327 (56), 370 (54), 271 (52), 541 (45), 315 (43), 114 (35), 344 (29), 301 (21), 496 (19), 362 (18), 181 (17), 654 (15), 524 (15), 542 (14) C32H46O8N8 336.17921 336.17923 0.07 SinAgm-2-7′/8-8′-SinAgmc
27 11.21 338 [M + 2H]2+ 336 271 (100), 131 (81), 315 (79), 306 (78), 541 (71), 411 (69), 383 (50), 157 (42), 328 (36), 327 (34), 114 (31), 542 (23) 524 (19), 344 (18), 361 (18), 412 (17), 370 (16), 387 (15), 231 (13) C32H46O8N8 336.17921 336.17899 –0.65 SinAgm-8-8′-SinAgmc
29 13.72 330 [M + 2H]2+ 336 306 (100), 327 (30), 315 (14), 157 (9) 131 (8), 320 (6), 114 (5), 271 (5), 541 (4), 654 (3) C32H46O8N8 336.17921 336.17905 –0.47 SinAgm-8-8′/9-N-7′-DSinAgmc
30 14.18 322 [M + H]+ 337 320 (100), 207 (55), 114 (18), 303 (14), 277 (12), 115 (10) C16H24O4N4 337.18703 337.18674 –0.87 trans-SinAgmc
a

All fragments with a relative abundance of 10% or higher and fragments linked to the fragmentation patterns (Figure 4) are reported.

b

Identified based on the fragmentation pattern.

c

Identified by NMR; n.d. = not detected.

d

Compound numbers correspond to selected numbers from Figure 3. RP-UHPLC- MS data of all peaks are given in Table S1.