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. Author manuscript; available in PMC: 2013 Apr 11.
Published in final edited form as: J Agric Food Chem. 2011 Oct 24;59(22):12059–12072. doi: 10.1021/jf202556p

Table 1.

UHPLC-PAD-ESI/HRMS/MSn Data and Putative Identification of Anthocyanins in Red Mustard Green

peak tR (min) [M]+wt [M]+formula error (ppm) major and important MS2 ions (m/z) (%) MS3 ion (m/z) (%) UV–vis λmax (nm) tentative identificationa
27 Acyiated Cyanidin 3-Sophoroside-5-diglucosides
3 15.89 1141.3234 C50H61O30 −0.72 817 (100), 611 (48) 287 (100) ndb Cy 3-sinapoylsophoroside-5-diglucoside
28 35.41 1287.3604 C59H67O32 −0.46 963 (100), 611 (10) 287 (100) 328, 536 Cy 3-p-coumaroylsinapoylsophoroside-5-diglucoside#
14 30.37 1289.3394 C58H65O33 −0.67 965 (100), 611 (15) 287 (100) nd Cy 3-caffeoylhydroxyferuloylsophoroide-5-diglucoside
17 31.84 1303.3560 C59H67O33 0.07 1141 (8), 979 (100), 611 (26) 287 (100) 328, 536 Cy 3-caffeoylsinapoylsophoroside-5-diglucoside
34 36.32 1317.3724 C60H69O33 0.64 993 (100), 611 (9), 593 (5) 287 (100) 328, 536 Cy 3-sinfersophoroside-5-digluco side
adc-5 34.86 1183.27S2 C54H55O30 0.79 773 (69), 697 (39) 287 (100) 328, 534 Cy 3-caffeoylsophoroside-5-malonyldiglucoside
20 33.56 1197.3137 C52H61O32 −0.29 949 (17), 787 (61), 697 (100) 287 (100) 326, 538 Cy 3-feruloylsophoroside-5-malonyldiglucoside
6 19.0001 1227.3226 C53H63O33 −1.64 817 (16), 697 (100), 653 (7) 287 (100) 328,536 Cy 3-caffeoylsinapoylsophoroside-5-malonyldiglucoside
45 39.75 1343.3512 C61H67O34 0.35 933 (100), 697 (61), 455 (11) 287 (100) 328, 536 Cy 3-p-coumaroylferuloylsophoroside-5-malonyldiglucoside
24 34.56 1345.3313 C60H65O35 0.90 935 (91), 697 (100), 679 (2), 653 (11) 287 (100) 326, 538 Cy 3-dicaffeoylsophoroside-5-malonyldiglucoside
29 35.70 1359.3455 C61H67O35 −0.18 1315 (20), 949 (100), 697 (90), 653 (6) 287 (100) 328, 536 Cy 3-caffeoylferuloylsophoroside-5-malonyldiglucoside
43 39.12 1359.3472 C61H67O35 1.07 1195 (2), 1067 (2), 949 (85), 697 (100) 287 (100) 328, 536 Cy 3-caffeoylferuloylsophoroside-5-malonyldiglucoside
38 37.88 1359.3469 C61H67O35 0.85 1315 (38), 949 (100), 697 (85) 287 (100) 328, 536 Cy 3-caffeoylferuloylsophoroside-5-malonyldiglucoside
47 40.23 1373.3639 C62H69O35 1.83 963 (100), 962 (3), 697 (88), 653 (3) 287 (100) 328, 538 Cy 3-p-coumaroylsinapoylsophoroside-5-malonyldiglucoside#
48 40.23 1373.3628 C62H69O35 1.03 963 (54), 697 (100), 653 (12) 287 (100) 328, 536 Cy 3-p-coumaroylsinapoylsophoroside-5-malonyldiglucoside#
19 33.44 1375.3407 C61H67O36 0.03 965 (100), 697 (93), 611 (4), 541 (2) 287 (100) 326, 538 Cy 3-hydroxyferuloylcaffeoylsophoroside-5-malonyldiglucoside
22 34.40 1399.3557 C62H69O36 −0.44 979 (100), 697 (67), 653 (22) 287 (100) 330, 534 Cy 3-caffeoylsinapoylsophoroside-5-malonyldiglucoside
39 38.32 1389.3566 C62H69O36 0.21 1077 (27), 979 (17), 734 (17), 697 (57) 287 (100) 328, 538 Cy 3-caffeoylsinapoylsophoroside-5-malonyldiglucoside
42 39.12 1403.3719 C63H71O36 −0.04 1359 (6), 993 (81), 697 (100), 653 (5) 287 (100) 326, 538 Cy 3-feruloylsinapoylsophoroside-5-malonyldiglucoside
10 24.74 1211.3290 C53H63O32 −0.57 787 (28), 711 (100) 287 (100) nd Cy 3-feruloylsophoroside-5-succinoyldiglucoside
9 23.89 1241.3389 C54H65O33 −1.10 817 (20), 711 (100) 287 (100) 328, 536 Cy 3-sinapoylsophoroside-5-succinoyldiglucoside
53 41.63 1357.3668 C62H69O34 0.24 1325 (2), 933 (100), 711 (97) 287 (100) 326, 538 Cy 3-p-coumaroylferuloylsophoroside-5-succinoyldiglucoside
40 38.58 1373.3608 C62H69O35 −0.43 1111 (5), 963 (4), 949 (98), 711 (100) 287 (100) 328, 536 Cy 3-caffeoylferuloyisophoroside-5-succinoyldiglucoside
50 40.93 1387.3773 C63H71O35 0.19 1355 (2), 1287 (2), 963 (100), 711 (89) 287 (100) 328, 536 Cy 3-p-coumarolylsoylsophoroside-5-succinoyldiglucoside#
57 42.36 1387.3767 C63H71O35 −0.25 963 (100), 711 (68) 287 (100) 328, 536 Cy 3-p-coumarolylsoylsophoroside-5-succinoyldiglucoside#
44 39.12 1403.3726 C63H71O36 0.46 1347 (83), 979 (100), 711 (92) 287 (100) 328, 536 Cy 3-feruloylhydroxyferuloylsophoroside-5-succinoyldiglucoside
54 41.66 1417.3879 C64H73O36 0.21 993 (100), 711 (86) 287 (100) 328, 536 Cy 3-dihydroxyferuloylsophoroside-5-succinoyldiglucoside
37 Acylated Cyanidin 3-Sophoroside-5-glucosides and 3 Acylated Cyanidin 3-Triglucoside-5-glucosides
4 17.74 919.2494 C42H47O23 −0.94 757 (100), 449 (14), 287 (48) 287 (100) nd Cy 3-p-coumaroylsophoroside-5-glucoside*
13 29.37 949.2609 C43H49O24 0.08 787 (100), 707 (9), 503 (4), 287 (70) 287 (100) 328, 532 Cy 3-feruloylsophoroside-5-glucoside*
1 13.61 965.2542 C43H49O25 −1.60 803 (73), 449 (51), 287 (100) 287 (100) nd Cy 3-hydroxyferuloylsoplioroside-5-glycoside*
35 36.78 1095.2969 C52H55O26 −0.65 933 (100), 449 (13) 287 (100) 326, 536 Cy 3-p-coumaroylferuloylsophoroside-5-glucoside*
16 31.23 1097.2765 C51H53O27 −0.34 935 (100), 449 (14) 287 (100) nd Cy 3-dicaffeoylsoprioroside-5-glucoside*
18 33.35 1111.2936 C52H55O27 0.97 949 (100), 449 (10) 287 (100) 328, 536 Cy 3-caffeoylferuloylsophoroside-5-gIucoside*
31 35.87 1125.3087 C53H57O27 0.47 963 (100), 449 (12) 287 (100) 328, 536 Cy 3-diferuloylsophoroside-5-glucoside*
15 30.73 1127.2847 C52H55O28 −2.43 965 (100)449 (21) 287 (100) nd Cy 3-caffeoylhydroxyferuloylsophoroside-5-glucoside
30 35.77 1141.3057 C53H57O28 0.54 979 (100)449 (15) 287 (100) 328, 536 Cy 3-caffeoylsinapoylsophoroside-5-glucoside*
36 36.82 1155.3197 C54H59O28 0.83 993 (100)449(9) 287 (100) 328, 536 Cy 3-sinapoylferuloylsophoroside-5-glucoside*
2 13.91 859.2135 C36H43O24 −0.44 611 (9), 535 (100), 491 (6), 287 (50) 287 (100) nd Cy 3-sophoroside-5-malonlyglucoside*
23 34.44 1005.2513 C45H49O26 0.64 757 (68), 535 (100), 491 (10), 287 (59) 287 (100) 328, 536 Cy 3-p-coumaroylsophoroside-5-malonylglucoside
ad-2 27.87 1021.4979 C45H49O27 −1.16 773 (54),535 (100), 491 (15), 287 (76) 287 (100) nd Cy 3-caffeoylsophoroside-5-malonylglucoside
27 35.21 1035.2616 C46H51O27 0.37 787 (51),535 (100), 491 (7), 287 (9) 287 (100) 326, 538 Cy 3-feruloylsophoroside-5-malonylglucoside
5 18.02 1051.2565 C46H51O28 0.35 803 (20), 535 (100) 287 (100) nd Cy 3-hydroferuloylsophoroside-5-malonylglucoside
7 19.74 1065.2719 C47H53O28 0.11 817 (100)535 (85) 287 (100) nd Cy 3-sinapoylsophoroside-5-malonylglucoside
56 41.94 1151.2882 C54H55O28 0.66 903 (20),535 (100), 491 (23), 374 (20) 287 (100) 328, 536 Cy 3-di-p-coumaroylsophoroside-5-malonylglucoside
ad-3 32.10 1167.3049 C51H59O31 1.22 919 (100)535 (90) 287 (100) 328, 532 Cy 3-p-coumaroyltriglucoside-5-malonylglucoside
51 41.14 1181.2993 C55H57O29 1.10 933 (100)919 (2), 535 (95), 491 (8) 287 (100) 328, 536 Cy 3-p-coumaroylferuloylsophoroside-5-malonylglucoside#
ad-4 27.57 1183.2981 C51H59C32 −0.25 933 (40),535 (100) 287 (100) nd Cy 3-caffeoyltriglucoside-5-malonylglucoside
33 36.17 1197.3149 C52H61O32 0.71 949 (53),897 (26), 773 (74), 535 (100) 287 (100) nd Cy 3-feruloyltriglucoside-5-malonylglucoside
32 36.00 1197.2939 C55H57O30 0.82 949 (82),535 (100), 491 (6) 287 (100) 328, 536 Cy 3-feruloylcaffeoylsophoroside-5-malonylglucoside
52 41.41 1211.3101 C56H59O30 1.27 963 (82),949 (4), 535 (100), 491 (10) 287 (100) 328, 536 Cy 3-p-coumaroylsinapoylsophoroside-5-malonylglucoside*
46 39.96 1211.3086 C56H59O30 0.03 963 (100)535 (98) 287 (100) 328, 536 Cy 3-diferuloylsophoroside-5-malonylglucoside
21 33.73 1213.2893 C55H57O31 1.21 1169 (6),965 (67), 535 (100), 491 (9) 287 (100) 328, 538 Cy 3-hydroxyferuloylcaffeoylsophoroside-5-malonylglucoside
25 34.80 1227.3046 C56H59O31 0.91 979 (100)619 (25), 535 (12) 287 (100) 328, 536 Cy 3-caffeoylsinapoylsophoroside-5-malonylglucoside
49 40.29 1241.3198 C57H61O31 0.54 1197 (20)993 (100), 535 (98), 491 (7) 287 (100) 328, 536 Cy 3-feruloylsinapoylsophoroside-5-malonylglucoside*
ad-1 15.01 873.2288 C37H45O24 −0.83 611 (25),549 (100), 287 (52) 287 (100) nd Cy 3-sophoroside-5-succinoylglucoside
37 37.34 1019.2676 C46H51O26 1.27 757 (56),549 (100), 395 (2), 287 (33) 287 (100) 328, 536 Cy 3-p-coumaroylsophoroside-5-succinoylglucoside*
26 35.18 1035.2633 C46H51O27 2.01 611 (40),549 (100), 287 (100) 287 (100) 328, 534 Cy 3-caffeoylsophoroside-5-succinoylglucoside
12 26.83 1049.2778 C47H53O27 0.88 787 (18),549 (95) 287 (100) nd Cy 3-feruloylsophoroside-5-succinoylglucoside
41 38.70 1049.2781 C47H53O27 1.17 787 (56),549 (100) 287 (100) 328, 536 Cy 3-feruloylsophoroside-5-succinoylglucoside
8 23.50 1065.2705 C47H53O28 −1.21 803 (11),549 (100) 287 (100) nd Cy 3-hydroxyferuloylsophoroside-5-succinoylglucoside
11 26.05 1079.2866 C48H55O28 −0.78 817 (18),549 (100) 287 (100) 328, 536 Cy 3-sinapoylsophoroside-5-succinoylglucoside
55 41.86 1181.2992 C55H57O29 1.01 919 (72),549 (100) 287 (100) 328, 536 Cy 3-p-coumarolycaffeoylsophoroside-5-succinoylglucoside
61 43.20 1195.3138 C56H59O30 0.11 933 (82),821 (73), 549 (100) 287 (100) 328, 536 Cy 3-p-coumarolyferuloylsophoroside-5-succinoylglucoside
60 42.81 1211.3097 C56H59O30 0.94 949 (88),549 (100) 287 (100) 328, 536 Cy 3-caffeoylferuloylsophoroside-5-succinoylglucoside
59 42.51 1225.3260 C57H61O30 1.46 963 (82),549 (100) 287 (100) 328, 536 Cy 3-diferuloylsophoroside-5-succinoylglucoside
58 42.44 1241.3203 C57H61O31 0.94 979 (81),549 (100) 287 (100) 328, 536 Cy 3-feruloylhydroxyferuloylsophoroside-5-succinoylglucoside
62 43.52 1255.3348 C58H53O30 0.02 993 (84),549 (100) 287 (100) 328, 536 Cy 3-feruloylsinapoylsophoroside-5-succinoylglucoside
Parent Anthocyanins in the Alkaline-Hydrolyzed Extract
AH-1 11.56 773.2132 C33H41O21 0.14 611 (43),449 (76), 287 (100) 287 (100) 278, 514 Cy 3-sophoroside-5-glucoside*
AH-2 12.44 935.2670 C39H51O26 0.72 611 (100)287 (95) 287 (100) 282, 514 Cy 3-sophoroside-5-diglucoside
a

Cy, cyanidin.

*

known brassica anthocyanins (most were identified with the reference anthocyanin in the database).

#

might be the isomer with two feruloyl groups.

b

nd, not detected.

c

ad, additional.