Table 2.
UHPLC-PAD-ESI/HRMS/MSn Data and Putative Identification of Flavonol Glycosides in Red Mustard Greens
| peak | tR (min) | [M − H]− wt | [M − H]− formula | error (ppm) | major and important MS2 ions (m/z) (%) | major and important MS3 ions (m/z) (%) | UV λmax (nm) | tentative identificationa |
|---|---|---|---|---|---|---|---|---|
| 2 | 6.33 | 949.2465 | C39H49Q27 | −0.178 | 737 (100) | 625 (40), 607 (100), 301 (75) | ndb | qn 3-sophorotrioside-7-glucoside**# |
| 43 | 17.46 | 1095.2536 | C48H55Q29 | 0.14 | 949 (12), 933 (100), 787 (13) | 787 (100), 769 (9) | 265, 334 | qn 3-p-coumaroylsophorotrioside-7-glucoside* |
| 7 | 9.02 | 1111.276 | C48H55Q30 | −2.126 | 949 (10), 787 (30) | 787 (100) | 255, 337 | qn 3-caffeoylsophorotrioside-7-glucoside* |
| 23 | 12.64 | 1125.2933 | C49H57Q30 | −0.713 | 963 (100), 949 (82), 787 (30) | 787 (100), 300 (4) | 256, 336 | qn 3-feruloylsophorotrioside-7-glucoside** |
| 45 | 17.81 | 1125.295 | C49H57Q30 | 0.88 | 963 (100), 949 (19), 787 (21) | 801 (13), 787 (100), 769 (13) | 256, 336 | qn 3-feruloylsophorotrioside-7-glucoside |
| 6 | 8.68 | 1141.2889 | C49H57Q31 | 1.069 | 979 (100) 949 (93), 787 (72) | 787 (100) | 256, 336 | qn 3-hydroxyferuloylsophorotrioside-7-glucoside |
| ad-1 | 14.59 | 1141.2861 | C49H57Q31 | −2.478 | 949 (56), 787 (100), 653 (28) | nd | 256, 336 | qn 3-triglucoside-7-hydroxyferuloylglucoside |
| 22 | 12.54 | 1155.3037 | C50H59Q31 | −0.76 | 993 (100), 949 (4), 625 (2) | 787 (100) | 254, 338 | qn 3-sinapoylsophorotrioside-7-glucoside** |
| ad-2 | 20.01 | 1155.3021 | C50H59Q31 | −2.478 | 993 (100), 949 (26) | 787 (100) | nd | qn 3-sinapoylsophorotrioside-7-glucoside** |
| 4 | 9.68 | 933.2486 | C39H49Q26 | −0.791 | 771 (100) | 609 (11), 591 (100), 285 (51) | 265, 348 | km 3-sophorotrioside-7-glucoside**# |
| 8 | 9.33 | 933.2507 | C39H49Q26 | 0.942 | 771 (100) | 609 (13), 591 (100), 285 (52) | nd | km 3-triglucoside-7-glucoside**# |
| 34 | 14.78 | 1079.2903 | C48H55Q28 | 1.64 | 917 (100) 915 (3), 771 (15), 753 (6) | 771 (100), 753 (33), 591 (6) | 268, 330 | km 3-p-coumaroylsophorotrioside-7-glucoside |
| 60 | 20.65 | 1079.2878 | C48H55Q28 | −0.68 | 917 (100) | 771 (100), 754 (33), 591 (12) | nd | km 3-p-coumaroylsophorotrioside-7-glucoside |
| 14 | 10.72 | 1095.2826 | C48H55Q29 | −0278 | 975 (2), 933 (100), 809 (7) | 771 (100), 753 (57), 591 (8) | 268, 334 | km 3-caffeoylsophorotrioside-7-glucoside* |
| 32 | 14.46 | 1109.3016 | C49H57Q26 | 2.26 | 947 (100), 771 (6), 753 (2) | 785 (83), 771 (100), 753 (51) | 268, 330 | km 3-feruloylsophorotrioside-7-glucoside** |
| 61 | 21.02 | 1109.3016 | C49H59Q29 | 1.08 | 947 (100) | 785 (68), 771 (100), 753 (56), 591 (12) | 268, 334 | km 3-feruloylsophorotrioside-7-glucoside** |
| 9 | 9.46 | 1125.2937 | C49H57Q30 | −0.278 | 963 (100) | 785 (68), 771 (100) | 268, 334 | km 3-hydroxyferuloylsophorotrioside-7-glucoside** |
| 31 | 14.2 | 1139.3103 | C50H59Q30 | 0.56 | 977 (100), 771 (3) | 771 (100), 753 (56), 285(3) | 268, 330 | km 3-sinapoylsophorotrioside-7-glucoside** |
| 59 | 20.47 | 1139.3093 | C50H59Q30 | −0.32 | 977 (100) | 785 (73), 771 (100), 753 (46) | 263, 334 | km 3-sinapoylsophorotrioside-7-glucoside** |
| 5 | 7.92 | 787.1942 | C33H39Q22 | 1.451 | 625 (100) | 505 (18), 445 (45), 300 (100) | 268, 346 | qn 3-sophoroside-7-glucoside**# |
| 25 | 13.1 | 787.1939 | C33H39Q22 | 0.054 | 625 (100), 607 (93), 505 (45) | 505 (18), 463 (18), 445 (40), 300 (100) | nd | qn 3-sophorotrioside**# |
| 11 | 9.93 | 787.1949 | C33H39Q22 | 1.339 | 625 (100) | 607 (2), 343 (8), 301 (100), 300 (20) | nd | qn 3-diglucoside-7-glucoside**# |
| 29 | 13.9 | 933.2303 | C42H45Q24 | −0.325 | 771 (100), 625 (25), 607 (9) | 625 (100), 607 (8) | 254, 328 | qn 3-p-coumaroylsophoroside-7-glucoside* |
| 54 | 19.46 | 933.2306 | C42H45O24 | −0.03 | 787 (14), 771 (100), 625 (11) | 625 (100), 607 (8) | nd | qn 3-p-coumaroylsophoroside-7-glucoside* |
| 13 | 10.51 | 949.2256 | C42H45O25 | 0.063 | 787 (100) 625 (22) | 625 (100) | 254, 330 | qn 3-caffeoylsophoroside-7-glucoside** |
| 21 | 12.28 | 949.226 | C42H45O25 | 1.56 | 787 (100) | 625 (46), 607 (94), 505 (55), 301 (100) | nd | qn 3-caffeoylsophoroside-7-glucoside** |
| 53 | 19.36 | 963.2413 | C43H47O25 | 0.11 | 801 (21), 787 (100), 769 (15) | 625 (31), 607 (100), 505 (45), 301 (74) | nd | qn 3-feruloylsophoroside-7-glucoside** |
| 57 | 19.92 | 963.2422 | C43H47O25 | 1.05 | 801 (100) 787 (47), 625 (26) | 639 (13), 625 (100), 607 (14) | nd | qn 3-feruloyldiglucoside-7-glucoside |
| 12 | 10.11 | 979.2349 | C43H47O26 | −1.23 | 817 (98), 787 (100), 625 (59) | 625 (100), 463 (2) | 255, 336 | qn 3-hydroxyferuloylsophoroside-7-glucoside* |
| 36 | 15.65 | 979.2359 | C43H47O26 | −0.21 | 787 (100) | 625 (100) | 255, 336 | qn 3-hydroxyferuloyltriglucoside* |
| 27 | 13.47 | 993.2523 | C44H49O26 | 0.55 | 831 (99), 787 (100), 625 (59) | 639 (19), 625 (100), 607 (11) | 255, 336 | qn 3-sinapoylsophoroside-7-glucoside** |
| 55 | 19.76 | 993.2541 | C44H49O26 | 2.36 | 831 (100), 787 (91), 625 (45) | 639 (22), 625 (100), 607 (13) | nd | qn 3-sinapoylsophoroside-7-glucoside** |
| 10 | 9.53 | 771.1978 | C33H39O21 | −1.131 | 609 (100) | 447 (14), 429 (100), 235 (100) | 265, 346 | km 3-sophoroside-7-glucoside**# |
| 67 | 22.53 | 917.2366 | C42H45O23 | 0.97 | 755 (100) | 609 (100), 591 (25) | nd | km 3-p-coumaroylsophoroside-7-glucoside** |
| 70 | 23.57 | 917.2348 | C42H45O23 | −0.99 | 771 (100), 753 (32) | 609 (12), 591 (100), 285 (57), 284 (16) | nd | km 3-p-coumaroylsophorotrioside* |
| 19 | 12.23 | 933.2297 | C42H45O24 | −0.925 | 771 (100), 647 (4), 591 (2) | 591 (100), 393 (12), 285 (37) | 268, 330 | km 3-caffeoylsophoroside-7-glucoside** |
| 37 | 15.76 | 947.2429 | C43H47O24 | −2.278 | 827 (2), 785 (100), 609 (2) | 624 (92), 609 (100), 591 (51) | 268, 330 | km 3-feruloylsophoroside-7-glucoside |
| 18 | 11.68 | 963.2355 | C43H47O25 | −5.69 | 801 (100), 609 (2) | 609 (100), 591 (3), 235 (3) | 268, 330 | km 3-hydroxyferuloylsophoroside-7-glucoside** |
| 49 | 18.42 | 963.2418 | C43H47O25 | 0.63 | 801 (100) | 609 (100) | 268, 330 | km 3-hydroxyferuloyldiglucoside-7-glucoside* |
| 35 | 15.37 | 977.2535 | C44H49O25 | −2.243 | 815 (100), 609 (3) | 609 (100), 591 (39), 285 (4) | 268, 330 | km 3-sinapoylsophoroside-7-glucoside** |
| 62 | 21.14 | 977.2571 | C44H49O25 | 0.27 | 785 (77), 771 (100), 753 (47), 591 (11) | 591 (100), 285 (45), 284 (15) | nd | km 3-sinapoylsophotrioside* |
| 90 | 29.94 | 1139.2876 | C53H55O28 | −0.82 | 977 (100), 933 (9), 771 (11), 663 (6) | 815 (21), 771 (100), 753 (18), 609 (10) | nd | km 3-caffeoylsinapoylsophoroside-7-glucoside* |
| 101 | 33.99 | 1153.3057 | C54H57O28 | 1.32 | 991 (100), 947 (10), 785 (23) | 815 (6), 785 (100), 767 (15), 339 (8) | nd | km 3-sinapoylferuloylsophoroside-7-glucoside |
| 109 | 37.85 | 1179.2847 | C55H55O29 | 1.06 | 1135 (100) | 931 (100) 755 (25) | nd | km 3-p-coumaroylferuloylsophoroside-7-malonylglucoside |
| 111 | 38.22 | 1179.2854 | C55H55O29 | 1.66 | 1135 (100), 931 (11) | 959 (7), 931 (100), 755 (20) | nd | km 3-p-coumaroylferuloylsophoroside-7-malonylglucoside |
| 104 | 35.59 | 1195.2771 | C55H55O30 | −1.06 | 1151 (100) | 959 (57), 947 (100), 755(36) | nd | km 3-p-coumaroylhydroxyferuloylsophoroside-7-malonylglucoside |
| 106 | 36.61 | 1209.2947 | C56H57O30 | 0.57 | 1165 (100) | 961 (100), 755 (23) | nd | km 3-p-coumaroylsinapoylsophoroside-7-malonylglucoside |
| 15 | 11.09 | 801.2083 | C34H41O22 | −1.196 | 639 (100), 477 (46), 315 (85) | 459 (64), 315 (100), 314 (52) | nd | is 3-sophoroside-7-glucoside**# |
| 30 | 14.07 | 801.2083 | C34H41O22 | 2.00 | 639 (100) | 315 (100), 300 (19) | nd | is 3-sophoroside-7-glucoside**# |
| 89 | 29.85 | 947.2464 | C43H47O24 | 0.13 | 785 (100) | 639 (96), 605 (46), 459 (46), 315 (100) | nd | is 3-p-coumaroylsophoroside-7-glucoside |
| 28 | 13.64 | 963.2419 | C43H47O25 | −0.74 | 801 (100) | 639 (100) | nd | is 3-caffeoylsophoroside-7-glucoside |
| ad-3 | 14.05 | 963.2405 | C43H47O25 | −0.72 | 801 (100), 797 (11), 625 (7) | 639 (100), 625 (46), 607 (7) | nd | is 3-caffeoylsophoroside-7-glucoside |
| 46 | 17.92 | 977.2575 | C44H49O25 | 0.68 | 815 (100) | 639 (100) | nd | is 3-feruloylsophoroside-7-glucoside |
| 26 | 13.17 | 993.2510 | C44H49O26 | −0.76 | 831 (100) | 639 (100) | nd | is 3-hydroxyferuloylsophoroside-7-glucoside |
| 41 | 17.05 | 1007.2683 | C45H51O26 | 0.89 | 845 (100) | 639 (100) | nd | is 3-sinapoylsophoroside-7-glucoside* |
| 102 | 34.25 | 1139.2888 | C53H55O28 | 0.23 | 977 (100) | 815 (100), 801 (10) | nd | is 3-caffeoylferuloylsophoroside-7-glucoside |
| 99 | 33.77 | 1169.2991 | C54H57O29 | 0.00 | 1007 (100) | 815 (100) | nd | is 3-caffeoylsinapoylsophoroside-7-glucoside |
| 115 | 39.05 | 1179.2837 | C55H55O29 | 0.21 | 1135 (100), 931 (11) | 989 (10), 931 (100), 785 (27) | nd | is 3-p-coumaroylcaffeoylsophoroside-7-malonylglucoside |
| 116 | 39.40 | 1179.2837 | C55H55O30 | 0.21 | 1135 (100), 931 (11) | 989 (10), 931 (100), 785 (27) | nd | is 3-p-coumaroylcaffeoylsophoroside-7-malonylglucoside |
| 107 | 36.99 | 1195.2786 | C56H57O31 | 0.20 | 1151 (100) | 989 (28), 947 (100), 785 (52) | nd | is 3-p-coumaroylcaffeoylsophoroside-7-malonylglucoside |
| 105 | 36.18 | 1225.2889 | C27H29O17 | −0.02 | 1181 (100) | 989 (40), 977 (100), 735 (30) | nd | is 3-p-coumaroylhydroxyferuloylsophoroside-7-malonylglucoside |
| 47 | 18.03 | 625.1414 | C27H29O17 | 0.60 | 505 (18), 463 (17), 445 (54), 300 (100) | 271 (100), 255 (52) | nd | qn 7-sophoroside**# |
| 17 | 11.49 | 625.1409 | C27H29O17 | 0.974 | 463 (100), 301 (24) | 301 (100), 300 (30) | nd | qn 3-glucoside-7-glucoside**# |
| 51 | 19.12 | 625.1410 | C27H29O17 | −0.04 | 463 (8), 343 (16), 301 (100) | 273 (17), 257 (17), 179 (100), 151 (73) | nd | qn diglucoside**# |
| 77 | 25.35 | 771.1788 | C36H35O19 | 1.29 | 625 (100) | 505 (18), 445 (52), 301 (49), 300 (100) | nd | qn 3-p-coumaroylsophoroside |
| 56 | 19.82 | 787.1788 | C37H37O20 | 0.87 | 625 (100) | 505 (18), 445 (56), 301 (53), 300(100) | nd | qn 3-caffeoylsophoroside* |
| 76 | 25.06 | 801.1833 | C37H37O20 | 1.42 | 625 (100), 607 (12) | 505 (18), 445 (55), 301 (46), 300 (100) | nd | qn 3-feruloylsophoroside* |
| 39 | 16.29 | 817.1833 | C37H37O21 | 0.02 | 625 (100) | 445 (53), 301 (100) | nd | qn 3-hydroxyferuloylsophoroside* |
| 48 | 18.25 | 817.1833 | C37H37O21 | 0.02 | 625 (100) | 505 (18), 445 (53), 301 (51), 300 (100) | nd | qn 3-hydroxyferuloylsophoroside* |
| 68 | 23.09 | 831.1997 | C38H39O21 | 0.93 | 625 (100) | 505 (17), 445 (48), 301 (41), 300 (100) | nd | qn 3-sinapoylsophoroside* |
| 33 | 14.68 | 609.1468 | C27H29O16 | 1.14 | 489 (13), 447 (100), 285 (18) | 327 (19), 285 (42), 284 (100), 255 (17) | nd | km 3-glucoside-7-glucoside**# |
| 51 | 19.32 | 609.1467 | C27H29O16 | 0.97 | 447 (59), 446 (27), 285 (100) | 257 (96), 151 (100) | nd | km 3-diglucoside*# |
| 65 | 22.34 | 609.1458 | C27H29O16 | −0.51 | 447 (14), 429 (100), 285 (89) | 339 (100), 327 (23), 313 (27), 309 (81) | nd | km 7-sophoroside*# |
| 72 | 24.18 | 609.1466 | C27H29O16 | 0.81 | 429 (2), 327 (3), 306 (3), 285 (100) | 267 (51), 257 (100), 241 (39), 229 (55) | nd | km 7-diglucoside*# |
| 88 | 29.56 | 755.1831 | C36H35O18 | 0.28 | 609 (100), 591 (26) | 429 (100), 285 (77), 284 (62), 255 (14) | nd | km 3-p-coumaroyldiglucoside** |
| 86 | 29.10 | 785.1942 | C37H38O19 | 0.95 | 623 (62), 609 (100), 591 (44), 429 (6) | 447 (12), 429 (100), 285 (90), 284 (66) | nd | km 3-feruloyldiglucoside* |
| 40 | 16.94 | 801.1863 | C37H37O20 | −2.067 | 623 (7), 609 (100), 591 (6) | 429 (100), 285 (91), 284 (87) | nd | km 3-hydroxyferuloylferuloylsophoroside* |
| 66 | 22.77 | 801.1890 | C37H37O20 | 0.79 | 609 (100) | 429 (100), 285 (91), 284 (62) | nd | km 3-hydroxyferuloylferuloylsophoroside* |
| 83 | 26.94 | 815.2046 | C38H39O20 | 0.72 | 623 (73), 609 (100), 591 (37) | 429 (100), 285 (76), 284 (50) | nd | km 3-sinapoylsophoroside* |
| ad-4 | 35.37 | 961.2399 | C47H45O22 | −0.896 | 815 (32), 755 (100) | 609 (56), 576 (30), 339 (100), 284 (29) | nd | km 3-p-coumaroylsinapoyldiglucoside |
| 38 | 16.19 | 639.1566 | C27H29O16 | 2.08 | 519 (10), 477 (100), 315 (12) | 357 (21), 315 (42), 314 (100) | 253,348 | is 3-glucoside-7-glucoside**# |
| 42 | 17.36 | 639.1567 | C28H31O17 | 0.04 | 519 (9), 477 (100), 315 (14) | 357 (20), 315 (43), 314 (100) | nd | is diglucoside*# |
| 63 | 21.59 | 639.1566 | C28H31O17 | −0.11 | 477(56), 315 (100), 313 (23) | 300(100) | nd | is 3-diglucoside*# |
| 71 | 23.97 | 639.1567 | C28H317O16 | 0.04 | 477 (26), 459 (51), 315 (100), 314 (45) | 300 (100) | nd | is 7-sophoroside*# |
| 81 | 26.21 | 639.1569 | C28H31O16 | 0.36 | 315 (100) | 300 (100) | nd | is diglucoside*# |
| 44 | 17.76 | 609.1462 | C27H29O16 | 0.15 | 477 (34), 476 (24), 447 (86), 515 (100) | 300 (100) | nd | is 3-pentaside-7-glucoside |
| 58 | 19.98 | 681.1677 | C30H33O18 | 0.68 | 519 (100), 477 (18), 315 (53) | 357 (23), 315 (30), 314 (100) | nd | is 3-acetylglucoside-7-glucoside |
| 98 | 33.73 | 815.2043 | C38H39O20 | 0.35 | 653 (100) | 477 (26), 329 (41), 323 (100), 315 (73) | nd | is 3-feruloylglucoside-7-glucoside |
| 117 | 39.52 | 815.2045 | C38H39O20 | 0.59 | 653 (100), 315 (11) | 315 (100), 300 (21) | nd | is 3-feruloylglucoside-7-glucoside |
| 100 | 33.94 | 831.1998 | C38H39O21 | 1.05 | 669 (100), 515 (6) | 353 (73), 315 (100), 300 (24) | nd | is 3-hydroxyferuloylglucoside-7-glucoside |
| ad-5 | 15.19 | 845.2127 | C39H41O21 | −0.784 | 653 (94), 639 (100), 621 (37), 315 (6) | 459 (24), 315 (100), 314 (81), 300 (24) | nd | is 3-sinapoylsophoroside |
| ad-6 | 33.99 | 961.239 | C47H45O22 | −0.596 | 785 (100), 767 (37), 755 (19), 339 (11) | 639 (100), 621 (70), 605 (95), 315 (65) | nd | is 3-p-coumaroylferuloyldiglucoside |
| ad-7 | 32.19 | 977.2352 | C47H45O23 | −0.522 | 799 (8), 785 (100), 771 (7), 623 (3) | 639 (60), 605 (49), 315 (100) | nd | is 3-hydroxyferuloyl-p-coumaroyldiglucoside |
| ad-8 | 33.33 | 991.2502 | C48H47O23 | −1.171 | 845 (8), 799 (91), 785 (100), 767 (36) | 639 (69), 605 (21), 315 (100), 300 (60) | nd | is 3-sinapoyl-p-coumaroyldiglucoside |
| ad-9 | 34.94 | 991.2502 | C48H47O23 | −1.171 | 829 (55), 815 (100), 797 (33), 485 (16) | 653 (89), 639 (76), 485 (100), 314 (46) | nd | is 3-diferuloyldiglucoside |
| ad-10 | 34.13 | 1021.2601 | C49H49O24 | −1.825 | 829 (45), 815 (100), 797 (22) | 639 (100), 621 (27), 485 (46) | nd | is 3-sinapoylferuloyldiglucoside |
| 74 | 24.63 | 463.0884 | C21H19O12 | 0.43 | 301 (100), 300 (25) | 179 (100), 151 (76) | 255, 368 | qn 7-glucoside**# |
| 85 | 28.43 | 505.0993 | C23H21O13 | 1.06 | 343 (6), 301 (100) | 285 (27), 273 (24), 179 (100), 151 (96) | nd | qn 3-acetylglucoside |
| 87 | 29.36 | 447.0936 | C21H19O11 | 0.71 | 327 (21), 285 (87), 284 (100), 255 (17) | 255 (100), 227 (12) | 264, 363 | km 7-glucoside**# |
| 91 | 30.95 | 477.1044 | C22H21O12 | 1.15 | 315 (35), 314 (100) | 285 (100), 271 (75), 243 (23) | 255, 349 | is 3-glucoside**# |
| 96 | 32.76 | 477.1042 | C22H21O12 | 0.74 | 315 (100), 314 (22) | 300 (100) | 255, 369 | is 7-glucoside**# |
| 103 | 34.73 | 519.1144 | C24H23O13 | −0.03 | 315 (100) | 300 (100) | nd | is 3-acetylglucoside |
a
km, kaempferol; qn, quercetin; is, isorhamnetin
*
known brassica flavonoid.
**
known brassica flavonoids identified with reference compound in the database.
#
detected in the alkaline hydrolyzed extract, too, and offered the UV data.
b
nd, not detected.