Table 3.
Soaking Water | Soaked Coats | Soaked Cotyledons | Whole Flour | References | ||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Class | Compound | CF | Expected Mass Da | Fragments MS2 | RT Average ± SD (min) | Found at Mass Da [M-H]- | Error ppm | IS | Found at Mass Da [M-H]- | Error ppm | IS | Found at Mass Da [M-H]- | Error ppm | IS | Found at Mass Da [M-H]- | Error ppm | IS | |
HBA | (1) Protocatechuic acid-4-O-Gl | C13H16O9 | 316.0794 | 108.0241/109.0319/152.0150/153.0229 | 27.8 ± 0.1 | 315.0722 | 0.0 | 0.8835 | 315.0724 | 0.8 | 0.8915 | 315.0716 | −1.8 | 0.8896 | 315.0701 | −6.5 | 0.7409 | [49] |
(2) Vanillic acid | C8H8O4 | 168.0423 | 108.0240/123.0489/124.0157/152.0158 | 28.1 ± 0.1 | 167.0351 | 1.0 | 0.9916 | 167.0352 | 1.4 | 0.7308 | 167.0351 | 0.7 | 0.9901 | 167.0351 | 0.8 | 0.9683 | [50,51] | |
(5) Protocatechuic acid* | C7H6O4 | 154.0266 | 108.0241/109.0325 | 31.4 ± 0.1 | 153.0196 | 1.7 | 0.9835 | 153.0200 | 4.4 | 0.9558 | 153.0195 | 0.9 | 0.9721 | 153.0194 | 0.5 | 0.9770 | [52,53] | |
(12) p-Hydroxybenzoic acid-4-O-Gl | C13H16O8 | 300.0845 | 93.0372/137.0304 | 36.5 ± 0.1 | 299.0775 | 0.9 | 0.8742 | 299.0770 | −0.8 | 0.8896 | 299.0771 | −0.5 | 0.8573 | 299.0756 | −5.6 | 0.9116 | [49] | |
(25) p-Hydroxybenzoic acid* | C7H6O3 | 138.0317 | 65.0413/93.0369 | 41.4 ± 0.1 | 137.0246 | 1.0 | 0.9898 | 137.0245 | 0.7 | 0.9804 | 137.0246 | 1.0 | 0.9797 | 137.0245 | 0.7 | 0.9880 | [51] | |
(27) Gentisic acid* | C7H6O4 | 154.0266 | 108.0241/109.0322 | 43.4 ± 0.1 | 153.0199 | 3.8 | 0.9684 | 153.0195 | 1.2 | 0.9061 | 153.0194 | 0.6 | 0.9798 | 153.0193 | −0.4 | 0.8411 | [13,54] | |
HCA | (3) p-Coumaroyl aldaric acid 1 | C15H16O10 | 356.0743 | 57.0358/59.0152/85.0312/89.0261/119.0370/129.0215/147.0313/191.0233/209.0339 | 29.5 ± 0.1 | 355.0673 | 0.6 | 0.9334 | 355.0653 | −4.9 | 0.9543 | 355.0745 | 20.8 | 0.9266 | 355.0714 | 12.3 | 0.9840 | [51] |
(6) p-Coumaroyl aldaric acid 2 | C15H16O10 | 356.0743 | 57.0363/59.0156/85.0316/129.0216/147.0330/163.0428/191.0235/209.0343 | 32.7 ± 0.1 | 355.067 | −0.3 | 0.8553 | 355.0656 | −4.2 | 0.9724 | 355.0657 | −3.9 | 0.8463 | 355.0654 | −4.6 | 0.8660 | [51] | |
(7) Feruloyl aldaric acid 1 | C16H18O11 | 386.0849 | 57.0362/59.0154/85.0315/129.0216/147.0327/191.0234/209.0339 | 33.4 ± 0.1 | 385.0772 | −1.1 | 0.8642 | 385.0755 | −5.5 | 0.9330 | 385.0761 | −4.0 | 0.8615 | 385.0761 | −3.9 | 0.8802 | [51,55] | |
(8) p-Coumaroyl aldaric acid 3 | C15H16O10 | 356.0743 | 57.0364/59.0159/85.0320/129.0225/147.0336/ 191.0246/ 209.0357 | 34.9 ± 0.1 | 355.0672 | 0.3 | 0.8547 | 355.0659 | −3.4 | 0.9032 | 355.0659 | −3.3 | 0.8706 | 355.0655 | −4.4 | 0.8581 | ND | |
HCA | (9) Sinapoyl aldaric acid 1 | C17H20O12 | 416.0955 | 57.0363/59.0155/85.0316/129.0220/147.0329/191.0230/209.0338 | 35.0 ± 0.1 | 415.0869 | −3.0 | 0.9592 | 415.0878 | −1.0 | 0.9388 | 415.0882 | 0.1 | 0.9354 | 415.0856 | −6.4 | 0.8778 | [55] |
(10) Feruloyl aldaric acid 2 | C16H18O11 | 386.0849 | 57.0362/85.0312/147.0323/191.0227/209.0339/223.0495 | 35.3 ± 0.1 | 385.0761 | −4.0 | 0.9050 | 385.0755 | −5.4 | 0.9710 | 385.0761 | −3.9 | 0.8701 | 385.0756 | −5.3 | 0.8887 | [51,55] | |
(13) Feruloyl aldaric acid 3 | C16H18O11 | 386.0849 | 57.0359/59.0154/85.0311/129.0217/147.0319/191.0228/193.0539/209.0331 | 36.6 ± 0.1 | 385.0764 | −3.3 | 0.9242 | 385.0753 | −6.0 | 0.9524 | 385.0763 | −3.4 | 0.8808 | 385.0758 | −4.8 | 0.8981 | [51,55] | |
(14) p-Coumaroyl aldaric acid 4 | C15H16O10 | 356.0743 | 85.0315/147.0326/191.0233/209.0343 | 36.8 ± 0.2 | 355.0665 | −1.6 | 0.8922 | 355.0653 | −4.8 | 0.9581 | 355.0659 | −3.2 | 0.8631 | 355.065 | −5.7 | 0.8873 | ND | |
(15) p-Coumaroyl aldaric acid 5 | C15H16O10 | 356.0743 | 57.0361/59.0153/85.0315/129.0216/147.0324/191.0234/209.0343 | 37.6 ± 0.1 | 355.0664 | −1.9 | 0.8651 | 355.0658 | −3.6 | 0.9319 | 355.0660 | −3.1 | 0.8480 | 355.0655 | −4.5 | 0.8628 | ND | |
(16) Feruloyl aldaric acid 4 | C16H18O11 | 386.0849 | 57.0361/85.0313/129.0211/147.0322/191.0228/209.0333 | 38.2 ± 0.1 | 385.0775 | −0.5 | 0.8943 | 385.0762 | −3.7 | 0.9035 | 385.0766 | −2.6 | 0.8748 | 385.076 | −4.3 | 0.8851 | [55] | |
(19) Sinapoyl aldaric acid 2 | C17H20O12 | 416.0955 | 57.0360/59.0154/85.0314/129.0214/147.0327/191.0234/209.0339/223.0661 | 38.7 ± 0.1 | 415.0865 | −4.0 | 0.9481 | 415.0856 | −6.2 | 0.9243 | 415.0855 | −6.4 | 0.9349 | 415.0851 | −7.5 | 0.9162 | [55] | |
(20) Sinapoyl aldaric acid 3 | C17H20O12 | 416.0955 | 57.0363/85.0317/129.0220/147.0329/191.0237/209.0343 | 39.4 ± 0.1 | 415.0871 | −2.5 | 0.8585 | 415.0855 | −6.5 | 0.9589 | 415.0859 | −5.5 | 0.8748 | 415.0857 | −6.1 | 0.8622 | ND | |
(22) Feruloyl aldaric acid 5 | C16H18O11 | 386.0849 | 57.0363/85.0315/129.0216/147.0326/191.0232/209.0342 | 40.2 ± 0.1 | 385.0774 | −0.7 | 0.8745 | 385.0758 | −4.8 | 0.9144 | 385.0767 | −2.5 | 0.8842 | 385.0762 | −3.6 | 0.8726 | [55] | |
(23) Sinapoyl aldaric acid 4 | C17H20O12 | 416.0955 | 57.0362/59.0154/85.0315/129.0215/147.0324/191.0234/209.0343 | 40.8 ± 0.1 | 415.0861 | −5.0 | 0.9706 | 415.0853 | −7.1 | 0.9082 | 415.0861 | −4.9 | 0.8771 | 415.0856 | −6.3 | 0.8977 | ND | |
HCA | (26) p-Coumaroyl aldaric acid 6 | C15H16O10 | 356.0743 | 57.0361/59.0154/85.0313/ 129.0212/147.0326/163.0420/191.0232/209.0339 | 41.8 ± 0.1 | NF | - | - | 355.0654 | −4.7 | 0.7331 | 355.0658 | −3.6 | 0.8664 | 355.0654 | −4.7 | 0.8717 | ND |
(30) Feruloyl aldaric acid 6 | C16H18O11 | 386.0849 | 57.0364/59.0157/85.0317/111.0106/129.0218/147.0333/191.0241/209.0348 | 44.5 ± 0.1 | 385.0772 | −1.0 | 0.8900 | 385.0760 | −4.1 | 0.8934 | 385.0766 | −2.8 | 0.9271 | 385.0764 | −3.2 | 0.8801 | ND | |
(31) Sinapoyl aldaric acid 5 | C17H20O12 | 416.0955 | 57.0361/59.0152/85.0314/129.0219/147.0326/191.0232/209.0339 | 44.8 ± 0.1 | 415.0871 | −2.7 | 0.8610 | 415.0857 | −6.1 | 0.9493 | 415.0863 | −4.7 | 0.8794 | 415.0858 | −5.9 | 0.8865 | ND | |
(40) p-Coumaric acid* | C9H8O3 | 164.0473 | 93.0364/117.0369/119.0529 | 58.9 ± 0.2 | 163.0407 | 4.2 | 0.9776 | 163.0404 | 1.9 | 0.9503 | NF | - | - | 163.0401 | 0.2 | 0.8870 | [25] | |
(43) Sinapic acid* | C11H12O5 | 224.0685 | 93.0361/121.0308/149.0272/163.0423/164.05077/165.0227/193.0175/208.0417 | 63.1 ± 0.2 | 223.0613 | 0.6 | 0.9604 | 223.0610 | −1.0 | 0.7187 | 223.0611 | −0.5 | 0.9814 | 223.0605 | −3.1 | 0.9721 | [25] | |
(44) Ferulic acid* | C10H10O4 | 194.0579 | 102.9351/133.0316/134.0400/149.0636/178.0305 | 63.8 ± 0.2 | 193.0510 | 1.9 | 0.9545 | 193.0506 | −0.3 | 0.8344 | NF | - | - | 193.0507 | 0.3 | 0.9355 | [25,51] | |
Flavanol | (4) (+)-Catechin 3′-O-glucose | C21H24O11 | 452.1319 | 137.0279/245.0874/289.0836/299.0835 | 30.8 ± 0.1 | 451.1234 | −2.5 | 0.8674 | 451.1227 | −4.2 | 0.8103 | 451.1220 | −5.8 | 0.8440 | 451.1218 | −6.1 | 0.8412 | [51] |
(11) Procyanidin B1 | C30H26O12 | 578.1424 | 125.0272/161.0276/287.0613/289.0771/407.0836/425.0935/451.1095 | 36.3 ± 0.1 | 577.1338 | −2.4 | 0.8707 | 577.1322 | −5.1 | 0.8217 | NF | - | - | 577.1308 | −7.6 | 0.8528 | [51] | |
(17) (+)-Catechin 7-O-β-D-Gl | C21H24O11 | 452.1319 | 245.0860/289.0766 | 37.7 ± 0.1 | 451.124 | −1.3 | 0.8408 | 451.1226 | −4.5 | 0.8522 | 451.1216 | −6.6 | 0.9377 | 451.1214 | −7.1 | 0.8410 | [56] | |
(18) Procyanidin B2* | C30H26O12 | 578.1424 | 125.0270/289.0768/407.0831/425.0936/451.1091 | 38.3 ± 0.1 | 577.1334 | −3.0 | 0.8429 | 577.1320 | −5.5 | 0.7773 | 577.1306 | −7.8 | 0.7106 | 577.1306 | −7.8 | 0.8349 | [51] | |
(21) Procyanidin C1 | C45H38O18 | 866.2058 | 575.1276/577.1431/695.1510/713.1622 | 40.2 ± 0.1 | 865.1957 | −3.3 | 0.7994 | 865.1925 | −7.0 | 0.7427 | 865.1950 | −4.1 | 0.5898 | 865.1907 | −9.0 | 0.8559 | [43,57] | |
Flavanol | (24) (+)-Catechin* | C15H14O6 | 290.079 | 109.0321/123.0479/125.0272/137.0274/151.0433/179.0388/203.0753/205.0546/221.0865/245.0866 | 40.6 ± 0.1 | 289.0719 | 0.4 | 0.8594 | 289.0718 | 0.0 | 0.8649 | 289.0711 | −2.1 | 0.9019 | 289.0714 | −1.1 | 0.8714 | [51] |
(28) Procyanidin B3 | C30H26O12 | 578.1424 | 125.0267/287.0609/289.0762/407.0829/425.0932/451.1094 | 43.7 ± 0.1 | 577.1331 | −3.5 | 0.8371 | 577.1312 | −6.9 | 0.8396 | NF | - | - | 577.1290 | −10.7 | 0.9183 | [51] | |
(32) Procyanidin B4 | C30H26O12 | 578.1424 | 125.0266/161.0267/287.0598/289.0756/407.0813/425.0923/451.1092 | 46.4 ± 0.1 | 577.1327 | −4.2 | 0.8305 | 577.1310 | −7.2 | 0.8814 | NF | - | - | 577.1294 | −9.9 | 0.7277 | [53] | |
(33) (-)-Epicatechin* | C15H14O6 | 290.079 | 109.0317/123.0476/125.0267/151.0425/203.0749/205.0537/245.0860 | 46.8 ± 0.1 | 289.0719 | 0.6 | 0.8671 | 289.0716 | −0.4 | 0.8691 | 289.0705 | −4.2 | 0.9701 | 289.0712 | −1.8 | 0.8682 | [58] | |
(35) Procyanidin C2 | C45H38O18 | 866.2058 | 575.1269 | 48.1 ± 0.2 | 865.1952 | −3.9 | 0.7947 | 865.1920 | −7.6 | 0.7222 | 865.1909 | −8.8 | 0.8242 | 865.1908 | −8.9 | 0.7730 | [57] | |
(36) Procyanidin B5 | C30H26O12 | 578.1424 | 125.0266/287.0603/289.0760/407.0825/425.0924/451.1082 | 50.8 ± 0.2 | 577.1334 | −3.0 | 0.8527 | 577.1316 | −6.2 | 0.8447 | 577.1296 | −9.6 | 0.7375 | 577.1308 | −7.6 | 0.8452 | [59] | |
Flavanones | (29) Eriodictyol-hexoside 1 | C21H22O11 | 450.1162 | 125.0267/179.0017/243.0698/259.0662/283.0657/287.0615/301.0764/421.1202 | 43.7 ± 0.1 | 449.1074 | −3.4 | 0.8475 | 449.1054 | −8.0 | 0.8682 | 449.1052 | −8.3 | 0.8673 | 449.1052 | −8.4 | 0.8317 | [51,55] |
(34) Eriodictyol-hexoside 2 | C21H22O11 | 450.1162 | 125.0273/259.0672/269.0510/287.0618 | 47.2 ± 0.1 | 449.108 | −2.0 | 0.8735 | 449.1068 | −4.6 | 0.8607 | 449.1070 | −4.3 | 0.8465 | 449.1061 | −6.2 | 0.8569 | [55] | |
(37) Eriodictyol-hexoside 3 | C21H22O11 | 450.1162 | 259.0651/287.0607 | 53.6 ± 0.1 | 449.1077 | −2.7 | 0.8574 | 449.1060 | −6.6 | 0.9051 | 449.1057 | −7.3 | 0.8843 | 449.1064 | −5.7 | 0.8703 | ND | |
Flavanones | (38) Eriodictyol-hexoside 4 | C21H22O11 | 450.1162 | 125.0262/151.0061/152.0143/179.0014/180.0094/269.0497/287.0590 | 56.7 ± 0.2 | 449.1078 | −2.6 | 0.8554 | 449.1056 | −7.5 | 0.9268 | 449.1056 | −7.4 | 0.9693 | 449.1062 | −6.1 | 0.8633 | ND |
(42) Naringenin-7-Gl | C21H22O10 | 434.1213 | 119.0521/151.0057/271.0647/313.0589 | 60.4 ± 0.2 | 433.1119 | −4.8 | 0.9503 | 433.1107 | −7.6 | 0.8883 | 433.1088 | −12.0 | 0.7686 | 433.1097 | −10.0 | 0.9045 | [53] | |
(50) Eriodictyol | C15H12O6 | 288.0634 | 125.0269/243.0703/259.0659 | 82.7 ± 0.2 | 287.0561 | −0.1 | 0.9315 | 287.0557 | −1.5 | 0.8979 | 287.0547 | −4.8 | 0.9471 | 287.0553 | −2.7 | 0.9044 | [51] | |
(53) Naringenin | C15H12O5 | 272.0685 | 107.0160/119.0524/151.0058/177.0228 | 95.4 ± 0.1 | 271.0610 | −0.7 | 0.9873 | 271.0605 | −2.6 | 0.9748 | 271.0605 | -2.7 | 0.9126 | 271.0602 | −3.8 | 0.9438 | [51] | |
Flavonols | (39) Luteolin 3′,7-di-O-Gl or kaempferol-3′,7-dihexoside | C27H30O16 | 610.1534 | 284.0373/285.0446 | 56.8 ± 0.2 | 609.1442 | −3.1 | 0.8322 | 609.1415 | −7.5 | 0.8720 | 609.1409 | −8.6 | 0.9374 | 609.1417 | −7.3 | 0.8715 | [60] |
(41) Rutin* | C27H30O16 | 610.1534 | 284.0370/285.0453/300.0320/301.0386/327.0554/607.2499 | 59.9 ± 0.2 | 609.1441 | −3.2 | 0.8302 | 609.1421 | −6.6 | 0.8892 | 609.1418 | −7.1 | 0.8585 | 609.1410 | −8.3 | 0.8494 | [25,55] | |
(45) Kaempferol-3-O-xylosyl-Gl | C26H28O15 | 580.1428 | 284.0377/285.0453/429.0891 | 64.7 ± 0.1 | 579.1335 | −3.5 | 0.8194 | NF | - | - | NF | - | - | 579.1316 | −6.9 | 0.8276 | [25,61] | |
(46) Quercetin-3-O-Gl | C21H20O12 | 464.0955 | 300.0318/301.0392 | 65.0 ± 0.2 | 463.0867 | −3.2 | 0.8117 | 463.0855 | −5.9 | 0.8163 | NF | - | - | 463.0849 | −7.1 | 0.8265 | [25,61] | |
(47) Quercetin-3-(6-O-acetyl-β-Gl) | C23H22O13 | 506.106 | 300.0319/301.0399/463.0923 | 73.2 ± 0.2 | 505.0970 | −3.5 | 0.8666 | 505.0942 | −9.1 | 0.9576 | NF | - | - | 505.0952 | −7.0 | 0.8700 | [55,62] | |
(48) Kaempferol-3-O-Gl | C21H20O11 | 448.1006 | 227.0397/255.0363/284.0447/285.0476 | 78.1 ± 0.1 | 447.0934 | 0.3 | 0.8361 | 447.0918 | −3.4 | 0.8064 | 447.0904 | −6.4 | 0.8319 | 447.0909 | −5.2 | 0.8716 | [25,55,61] | |
(49) Kaempferol-3-O-acetyl-Gl | C23H22O12 | 490.1111 | 255.0339/284.0386/285.0451 | 82.4 ± 0.1 | 489.1027 | −2.2 | 0.8634 | 489.1004 | −7.1 | 0.8248 | 489.1006 | −6.5 | 0.8577 | 489.1010 | −5.8 | 0.8644 | [61] | |
(52) Quercetin* | C15H10O7 | 302.0427 | 107.0143/121.0312/151.0059/179.0017/255.2372/273.0434 | 91.2 ± 0.1 | 301.0347 | −2.1 | 0.9273 | 301.0353 | −0.2 | 0.8619 | 301.0341 | −4.3 | 0.9211 | 301.0336 | −5.9 | 0.9445 | [25,51] | |
Flavonols | (55) Kaempferol* | C15H10O6 | 286.0477 | 93.0368/107.0159/151.0062/159.0479/185.0639/187.0428/211.0429/229.0545/239.0385/257.0493 | 97.4 ± 0.1 | 285.0407 | 1.0 | 0.8786 | 285.0403 | −0.5 | 0.8557 | 285.0402 | −1.0 | 0.8565 | 285.0400 | −1.6 | 0.8669 | [25,61] |
Isoflavones | (51) Daidzein* | C15H10O4 | 254.0579 | 209.0643/224.0538/225.0617 | 88.5 ± 0.1 | 253.0505 | −0.4 | 0.9479 | 253.0503 | −1.2 | 0.8295 | 253.0502 | −1.7 | 0.9510 | 253.0495 | −4.4 | 0.7987 | [61] |
(54) Genistein* | C15H10O5 | 270.0528 | 133.0309 | 96.3 ± 0.1 | 269.0452 | −1.2 | 0.7351 | 269.0447 | −3.1 | 0.9337 | 269.0449 | −2.5 | 0.8803 | NF | - | - | [61] |
CF—Chemical Formula; IS—Isotope Score; RT—Retention Time; SD—Standard Deviation; HBA—Hydroxybenzoic Acid; HCA—Hydroxycinnamic Acid; Gl—Glucoside; * Compounds identified by comparison with standards; the major fragments are underlined; NF—Not Found; ND—Not Described.