Skip to main content
. 2019 Jul 28;8(8):296. doi: 10.3390/foods8080296

Table 3.

Phenolic compounds identified in sample’s 22 fractions.

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.