Table 1. Identification of Nonanthocyanin Phenolic Compounds in White and Blue Bilberry Juices and Winesa.
| DAD | measured mass (m/z) | theoretical mass (m/z) | mass error (ppm) | fragment ion (m/z) | |||||
|---|---|---|---|---|---|---|---|---|---|
| peak | molecular formula | identification | retention time (min) | λmax (nm) | [M – H]−/[M + H]+ | [M – H]−/[M + H]+ | [M – H]−/[M + H]+ | [A – H]−/[A + H]+ | identification method |
| phenolic acids | |||||||||
| 1 | C16H18O9 | 5-caffeoylquinic acid | 3.1 | 324 | 353.0884/355.1033 | 353.0877/355.1025 | 2.01/2.33 | 191.0577/– | UV, MS, standard |
| 2 | C13H16O9 | protocatechuic acid hexoside | 3.4 | 317 | 315.0732/– | 315.0720/– | 3.68/– | 153.0200/– | UV, MS, literature47 |
| 3 | p-coumaric acid derivative-1 | 4.1 | 309 | 371.0985/– | – | – | 163.0408, 119.0509/– | UV, MS, literature29 | |
| 4 | p-coumaric acid derivative-2 | 4.5 | 324 | 371.0984/– | – | – | 163.0604, 119.0507/– | UV, MS, literature29 | |
| 5 | C15H18O9 | caffeic acid hexoside-1 | 5.2 | 314 | 341.0878/343.1039 | 341.0877/343.1025 | 0.32/4.16 | 179.0354, 135.0453/181.0502, 163.0494 | UV, MS, literature30 |
| 6 | C16H18O9 | 3-caffeoylquinic acid | 5.5 | 325 | 353.0873/– | 353.0877/– | –1.11/– | 191.0561/163.0409, 135.0455 | UV, MS, standard |
| 7 | C16H18O9 | 4-caffeoylquinic acid | 5.7 | 324 | 353.0873/– | 353.0877/– | –1.11/– | 191.0559/– | UV, MS, literature28 |
| 8 | C9H8O4 | caffeic acid | 6.1 | 321 | 179.0345/181.0497 | 179.0349/181.0495 | –2.05/0.91 | 161.0451/163.0408, 135.0447 | UV, MS, standard29 |
| 9 | C15H18O9 | caffeic acid hexoside-2 | 7.1 | 302 | 341.0881/– | 341.0877/– | 1.20/– | 179.0354, 135.0455/– | UV, MS, literature30 |
| 10 | C16H18O9 | caffeoylquinic acid isomer | 8.2 | 317 | 353.0882/– | 353.0877/– | 1.44/– | 191.0564/– | UV, MS, literature29 |
| 11 | C16H18O8 | p-coumaroylquinic acid | 8.6 | 310 | 337.0917/– | 337.0928/– | –3.19/– | 191.0550, 173.0446, 163.0388/– | UV, MS, literature29 |
| 12 | C9H8O3 | p-coumaric acid | 10.1 | 309 | 163.0407/165.0546 | 163.0400/165.0546 | 4.58/–0.13 | 119.0502, 93.0346/147.0443, 91.0543, 119.0491 | UV, MS, standard29 |
| 13 | C25H24O12 | dicaffeoylquinic acid-1 | 12.0 | 309 | 515.1176/517.1326 | 515.1194/517.1342 | –3.47/–3.03 | 353.0871/355.1027 | UV, MS, literature28 |
| 14 | C25H24O12 | dicaffeoylquinic acid-2 | 12.9 | 308 | 515.1173/517.1324 | 515.1194/517.1342 | –4.05/–3.42 | 353.0866/355.1026 | UV, MS, literature28 |
| 15 | caffeic acid derivative hexoside | 15.7 | 322 | –/559.1922 | –/397.1384, 181.0509 | UV, MS, literature29 | |||
| 16 | C25H28O13 | p-coumaroyl monotropein-1 | 18.2 | 307 | 535.1454/– | 535.1456/– | –0.37/– | 491.1575, 373.0942, 371.0990, 329.1035, 311.0930, 191.0357, 163.0409, 119.0509, 147.0451/– | UV, MS, literature30−32 |
| 17 | C25H28O13 | p-coumaroyl monotropein-2 | 19.2 | 311 | 535.1447/– | 535.1456/– | –1.68/– | 491.1550, 373.0924, 371.0980, 329.1023, 311.0920, 191.0348, 163.0400, 147.0451, 119.0502/– | UV, MS, literature30−32 |
| 18 | p-coumaric acid derivative | 22.6 | 311 | –/435.1664 | – | – | –/309.0954, 165.0548, 147.0427 | UV, MS, literature29 | |
| 19 | p-coumaric acid derivative-a | 24.9 | 310 | 411.1682/– | – | – | 163.0410, 145.0299, 119.0502/– | UV, MS, literature30 | |
| 20 | p-coumaric acid derivative-b | 25.0 | 312 | 411.1681/– | – | – | 163.0410, 145.0307, 119.0501/– | UV, MS, literature30 | |
| 21 | p-coumaric acid derivative-c | 25.1 | 310 | 411.1665/– | – | – | 163.0405, 145.0298, 119.0505/– | UV, MS, literature30 | |
| 22 | caffeic acid derivative | 25.3 | 310 | 445.1140/– | – | – | 411.1665, 179.0335, 135.0454/– | UV, MS, literature30 | |
| flavonols | |||||||||
| 23 | C21H20O13 | myricetin 3-O-galactoside | 13.7 | 353 | 479.0849/481.0982 | 479.0831/481.0977 | 3.73/1.11 | 317.0292/319.0452 | UV, MS, literature29,34 |
| 24 | C21H20O13 | myricetin 3-O-glucoside | 14.5 | 353 | 479.0848/481.0980 | 479.0831/481.0977 | 3.52/0.69 | 317.0295/319.0450 | UV, MS, literature29,34 |
| 25 | C21H20O12 | quercetin 3-O-galactoside | 17.8 | 351 | 463.0888/465.1043 | 463.0882/465.1028 | 1.30/3.33 | 301.0375/303.0509 | UV, MS, literature29 |
| 26 | C21H18O13 | quercetin 3-O-glucuronide | 18.6 | 352 | 477.0670/479.0836 | 477.0675/479.0820 | –0.97/3.3 | 301.0356/303.0508 | UV, MS, literature29 |
| 27 | C21H20O12 | quercetin 3-O-glucoside | 19.0 | 352 | 463.0875/465.1047 | 463.0882/465.1028 | –1.51/4.19 | 301.0330/303.0514 | UV, MS, standard29 |
| 28 | C22H22O13 | laricitrin 3-O-galactoside | 19.6 | 352 | –/495.1155 | –/495.1133 | –/4.41 | –/333.0625 | UV, MS, literature48 |
| 29 | C22H22O13 | laricitrin 3-O-glucoside | 20.1 | 352 | 493.0972/495.1153 | 493.0988/495.1133 | –3.17/4.01 | 331.0440/333.0623 | UV, MS, literature48 |
| 30 | C20H18O11 | quercetin 3-O-arabinoside | 20.4 | 353 | 433.0766/435.0925 | 433.0776/435.0922 | –2.39/0.72 | 301.0339/303.0529 | UV, MS, literature29 |
| 31 | C20H18O11 | quercetin 3-O-xyloside | 20.5 | 353 | 433.0767/435.0935 | 433.0776/435.0922 | –2.16/3.02 | 301.0344/303.0524 | UV, MS, literature29 |
| 32 | C15H10O8 | myricetin aglycone | 21.6 | 369 | 317.0289/319.0463 | 317.0303/319.0448 | –4.39/4.56 | – | UV, MS, literature48 |
| 33 | C22H22O12 | isorhamnetin 3-O-galactoside | 22.6 | 355 | 477.1024/479.1196 | 477.1039/479.1184 | –3.04/2.50 | –/317.0687 | UV, MS, literature29 |
| 34 | C23H24O13 | syringetin 3-O-galactoside | 22.7 | 353 | 507.1129/509.1293 | 507.1144/509.1290 | –2.99/0.65 | –/347.0767 | UV, MS, literature48 |
| 35 | C23H24O13 | syringetin 3-O-glucoside | 33.0 | 354 | 507.1130/509.1296 | 507.1144/509.1290 | –2.79/1.24 | –/347.0769 | UV, MS, standard48 |
| 36 | C15H10O7 | quercetin aglycone | 25.2 | 372 | 301.0360/303.0504 | 301.0354/303.0499 | 2.07/1.55 | – | UV, MS, literature48 |
| 37 | C17H14O8 | syringetin aglycone | 28.5 | 371 | 345.0627/347.0766 | 345.0616/347.0761 | 3.21/1.33 | – | UV, MS, literature48 |
| flavan-3-ols | |||||||||
| 38 | C15H14O7 | (−)-epigallocatechin | 4.4 | 279 | 305.0668/307.0820 | 305.0700/307.0812 | 0.78/2.51 | 219.0515/– | UV, MS, literature29,30 |
| 39 | C15H14O6 | (+)-catechin | 6.0 | 279 | 289.0714/291.0870 | 289.0718/291.0863 | –1.25/2.35 | 245.0824, 205.0513/– | UV, MS, standard |
| 40 | C30H26O12 | procyanidin B-type dimer | 6.1 | 280 | 577.1335/579.1514 | 577.1352/579.1497 | –2.86/2.93 | –/427.1040, 409.0923, 291.0894, 289.0739, 271.0632, 247.0629, 163.0417, 139.0393 | UV, MS, literature35 |
| 41 | C15H14O6 | (−)-epicatechin | 8.0 | 280 | 289.0709/291.0875 | 289.0718/291.0863 | –2.98/4.07 | 245.0819, 205.0509/207.0659, 165.0552, 139.0395, 123.0453 | UV, MS, standard |
| 42 | C45H38O18 | procyanidin B-type trimer | 8.9 | 279 | 865.1991/867.2172 | 865.1985/867.2131 | 0.65/4.74 | –/697.1443, 579.1522, 577.1326, 453.0842, 441.1737, 291.0875 | UV, MS, literature29,36 |
a
–: not recorded.