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. 2021 May 12;10(5):1070. doi: 10.3390/foods10051070

Table 1.

Differential metabolites in ZJT and YKT samples by metabolomics analysis based on ultra-high performance liquid chromatography combined with Orbitrap mass spectrometry (UHPLC-Orbitrap-MS/MS).

Compound Name RT (min) Detected Mass Theoretical Mass Adduct Formula MS/MS Fragment VIP p-Value |Log2 FC| FC
Flavan-3-ols
Epiafzelechin 3-O-gallate 4.30 426.0945 426.0951 [M-H2O-H]- C22H18O9 169, 125 1.38 2.00 × 10−9 1.30 2.46
Epicatechin 3-O-gallate 4.49 442.0925 442.0905 [M-H2O-H]- C22H18O10 123, 139, 153 1.37 3.00 × 10−8 1.97 3.91
Catechin * 4.60 290.0785 290.0790 [M+H]+ C15H14O6 95,97,109,123,125 1.23 2.00 × 10−4 0.83 1.78
Epigallocatechin gallate * 5.02 458.0831 458.0849 [M+H]+ C22H18O11 139, 151, 289 1.45 4.00 × 10−3 1.31 0.40
Epigallocatechin 3-(3”-methylgallate) 5.96 472.1006 472.1006 [M-H]- C23H20O11 139, 140, 167 1.38 4.00 × 10−9 6.06 66.66
Epicatechin 3-O-(3-O-methylgallate) 7.32 456.1055 456.1056 [M-H]- C23H20O10 109, 124, 168, 183, 289 1.38 2.00 × 10−8 7.61 195.68
Epicatechin * 7.34 290.0793 290.0790 [M-H]- C15H14O6 123, 139, 147, 207 1.37 2.00 × 10−8 3.57 11.87
Epigallocatechin 3-p-coumaroate 8.12 452.1109 452.1107 [M-H]- C24H20O9 196, 255 1.37 5.00 × 10−8 1.60 3.03
Proanthocyanins
Epigallocatechin-(4beta->8)-epicatechin 3-O-gallate 4.27 746.1481 746.1483 [M+H]+ C37H30O17 305, 443, 579 1.36 3.00 × 10−7 1.73 3.32
Procyanidin B5 5.25 578.1430 578.1424 [M-H2O-H]- C30H26O12 289, 469 1.37 8.00 × 10−8 3.05 8.29
3-O-beta-D-Galactopyranosylproanthocyanidin A5′ 5.50 738.1771 738.1796 [M+Na]+ C36H34O17 195, 455, 723 1.31 8.00 × 10−6 9.93 976.56
Prodelphinidin B 6.01 610.1335 610.1323 [M+H]+ C30H26O14 309, 757 1.38 2.00 × 10−9 2.46 5.49
Epigallocatechin 3-O-gallate-(4beta->6)-epicatechin 3-O-gallate 6.67 898.1590 898.1593 [M+H]+ C44H34O21 433, 741 1.32 5.00 × 10−6 1.39 2.62
Epiafzelechin 3-O-gallate-(4beta->6)-epigallocatechin 3-O-gallate 7.41 882.1608 882.1643 [M+H]+ C44H34O20 271, 441, 591 1.25 8.00 × 10−5 1.53 2.89
Flavonol and flavone glycosides
Myricetin 3.65 318.0383 318.0376 [M-H2O-H]- C15H8O7 125, 169, 241 1.39 9.00 × 10−10 4.31 19.85
Vitexin 2″-O-rhamnoside-4‴-acetate 3.77 620.1727 620.1741 [M-H2O-H]- C29H32O15 339, 449, 493 1.16 9.00 × 10−4 0.69 1.61
Kaempferol 3-O-arabinoside 4.05 418.0891 418.0900 [M+H]+ C20H18O10 211, 401 1.37 7.00 × 10−8 5.07 33.57
Quercetin 3-galloylglucosyl-arabinofuranoside 4.32 748.1520 748.1487 [M-H]- C33H32O20 229, 285 1.38 8.00 × 10−9 2.46 5.50
Myricetin 3-rhamnoside-3′-glucoside 4.95 626.1495 626.1483 [M-H]- C27H30O17 178, 316 1.05 5.00 × 10−3 0.72 1.64
Isovitexin 2″-O-rhamnoside 4.95 578.1621 578.1636 [M+H]+ C27H30O14 247, 291, 409, 427 1.24 1.00 × 10−4 2.67 6.36
Kaempferol 3-glucoside 5.27 448.1007 448.1006 [M-H2O-H]- C21H20O11 145, 301, 377 1.29 2.00 × 10−5 1.34 2.52
Kaempferol 7,4′-dirhamnoside 5.50 578.1629 578.1636 [M-H]- C27H30O14 245, 289 1.26 6.00 × 10−5 2.75 6.72
Pelargonidin 3-rhamnoside 5-glucoside 5.50 579.1722 579.1714 [M-H]- C27H31O14 154, 245, 289, 469 1.25 1.00 × 10−4 2.79 6.90
Cyanidin 3-sambubioside 5.63 581.1510 581.1506 [M-H]- C26H29O15 419, 435, 449, 458 1.28 3.00 × 10−5 0.99 1.99
Quercetin 3-rutinoside-4′-glucoside 5.90 772.2045 772.2062 [M-H]- C33H40O21 151, 255, 271, 301, 300 1.31 7.00 × 10−6 9.73 849.64
Cyanidin 3-diglucoside 5-glucoside 5.90 773.2145 773.2140 [M-H]- C33H41O21 277, 513 1.30 1.00 × 10−5 11.33 2579.02
Kaempferol 3-(2″-hydroxypropionylglucoside)-4′-glucoside 5.94 682.1734 682.1745 [M-H2O-H]- C30H34O18 213, 249, 327 1.36 3.00 × 10−7 4.87 29.33
Delphinidin 3-(6-p-coumaroylgalactoside) 6.01 611.1379 611.1401 [M+H]+ C30H27O14 138, 331, 409 1.38 2.00 × 10−9 2.65 6.29
Quercetagetin 7-methylether 6-glucoside 6.04 494.1060 494.1060 [M-H]- C22H22O13 163, 319, 337 1.30 1.00 × 10−5 2.04 4.10
Quercetin 3-arabinoside 6.11 434.0853 434.0849 [M-H]- C20H18O11 343, 313 1.36 1.00 × 10−7 2.15 4.43
Delphinidin-3-O-arabinoside 6.12 435.0933 435.0927 [M-H]- C20H19O11 165, 289, 341 1.26 8.00 × 10−5 2.11 4.33
Quercetin 3-galactoside 6.14 464.0944 464.0955 [M+H]+ C21H20O12 138, 303 1.08 3.00 × 10−3 0.91 1.88
Cyanidin 3-(6″-acetylglucoside)-5-glucoside 6.31 652.1641 652.1639 [M-H2O-H]- C29H32O17 207, 315, 515 1.08 3.00 × 10−3 0.63 1.55
Pelargonidin 3-sophoroside 5-glucoside 6.32 757.2184 757.2191 [M+H]+ C33H41O20 287, 433, 595 1.39 5.00 × 10−10 5.98 63.09
Cyanidin 3-O-(6-O-p-coumaroyl)glucoside 6.46 594.1373 594.1373 [M+H]+ C30H26O13 166, 273, 424, 442, 527 1.39 2.00 × 10−10 2.17 4.49
Kaempferol 3-(6″-ferulylglucoside) 6.51 624.1464 624.1479 [M+H]+ C31H28O14 317, 165, 203 1.33 2.00 × 10−6 8.49 360.45
Pelargonidin 3-coumarylglucoside-5-acetylglucoside 6.52 782.2061 782.2058 [M-H2O-H]- C38H38O18 457, 461, 337 1.31 1.00 × 10−5 3.73 13.26
Kaempferol 3-O-[2″-(4‴--acetyl-rhamnosyl)-6″-glucosyl] glucoside 6.53 798.2216 798.2219 [M+H]+ C35H42O21 519, 524 1.36 2.00 × 10−7 4.01 16.15
Kaempferol 3-glucoside-7-xyloside 6.83 580.1452 580.1428 [M+H]+ C26H28O15 271, 396 1.33 2.00 × 10−6 3.93 15.27
Kaempferol 3-(4″-acetyl-6″-p-coumarylglucoside) 8.14 636.1456 636.1479 [M-H2O-H]- C29H32O16 313, 465, 483 1.36 2.00 × 10−7 3.16 8.93
Quercetin 3,3′-dimethyl ether 4′-glucoside 8.58 510.1369 510.1373 [M-H2O-H]- C23H26O13 285, 442, 599 1.18 5.00 × 10−4 1.04 2.05
Kaempferol 8.90 286.0465 286.0477 [M+H]+ C15H10O6 121, 165, 241 1.55 4.00 × 10−3 1.80 0.29
Phenolic acids
Phenol 0.74 94.0414 94.0419 [M+H]+ C6H6O 62, 73, 82 1.23 4.00 × 10−3 1.24 0.42
5-O-Caffeoylquinic acid 1.51 354.0955 354.0951 [M-H]+ C16H18O9 103, 175 1.36 2.00 × 10−7 2.33 5.02
Chlorogenic acid 2.42 354.0933 354.0951 [M+Na]+ C16H18O9 93, 135, 173, 191 1.47 4.00 × 10−3 0.71 0.61
Salicylic acid 4.24 138.0309 138.0317 [M+H]+ C7H6O3 56, 65, 116, 139, 140 1.52 4.00 × 10−3 1.44 0.37
4-Hydroxybenzoic acid 5.02 138.0312 138.0317 [M+H]+ C7H6O3 56, 111, 116, 139, 140 1.40 4.00 × 10−3 0.69 0.62
3-O-Methylgallate 7.35 184.0376 184.0372 [M-H]- C8H8O5 124, 139, 168 1.33 3.00 × 10−6 0.97 1.97
3-O-p-Coumaroylquinic acid 7.54 338.1000 338.1002 [M-H2O-H]- C16H18O8 93, 119, 173, 191 1.15 1.00 × 10−3 1.31 2.48
Shikimic acid 9.49 174.0521 174.0528 [M-H2O-H]- C7H10O5 61, 67, 93, 173 1.33 4.00 × 10−3 0.68 0.62
Amino acids
Lysine 0.63 146.1050 146.1055 [M+H]+ C6H14N2O2 72, 84, 128, 130 1.36 4.00 × 10−3 1.01 0.50
Alanine 0.72 89.0472 89.0477 [M+H]+ C3H7NO2 68, 77 1.27 4.00 × 10−3 0.88 0.54
Aspartic acid 0.74 133.0371 133.0375 [M+H]+ C4H7NO4 74, 88, 102, 116 1.15 4.00 × 10−3 1.84 0.28
Methionine 1.04 149.0503 149.0510 [M+H]+ C5H11NO2S 102, 131 1.23 4.00 × 10−3 1.37 0.39
Valine 1.05 117.0785 117.0790 [M+H]+ C5H11NO2 58, 59, 118, 119 1.32 4.00 × 10−3 1.04 0.49
Isoleucine 1.92 131.0939 131.0946 [M+H]+ C6H13NO2 69, 72, 86, 90 1.39 4.00 × 10−3 0.89 0.54
Tyrosine 2.76 181.1882 181.1885 [M-H]- C9H11NO3 91, 119, 123, 136, 165 1.37 7.00 × 10−8 3.57 11.84
Cysteine 5.63 121.1586 121.1582 [M-H]- C3H7NO2S 74, 100, 98 1.22 2.00 × 10−4 0.90 1.87
Alkaloids
Adenine 0.63 135.0556 135.0545 [M-H]- C5H5N5 119 1.28 4.00 × 10−3 0.84 0.56
2-Acetylpyrazine 1.04 122.0475 122.0480 [M+H]+ C6H6N2O 80, 95, 96, 123 1.28 4.00 × 10−3 1.91 0.27
3-Methylxanthine 1.15 166.0487 166.0491 [M+H]+ C6H6N4O2 120 1.28 4.00 × 10−5 3.17 9.01
Ellagic acid 3.86 302.0048 302.0063 [M+H]+ C14H6O8 57, 275, 285, 303 1.20 4.00 × 10−3 1.71 0.31
2-Acetylpyrrole 4.27 109.0526 109.0528 [M+Hac-H]- C6H7NO 67, 83 1.29 4.00 × 10−3 1.42 0.37
Theophylline 6.27 180.0641 180.0647 [M-H2O+H]- C7H8N4O2 135, 146, 161, 164 1.50 4.00 × 10−3 0.62 0.65
Aquifoliunine EII 6.32 721.2591 721.2582 [M+K]+ C34H43NO16 231, 273, 411 1.39 2.00 × 10−10 4.82 28.31
Caffeine * 9.54 194.0800 194.0804 [M-H2O-H]- C8H10N4O2 85, 93 1.30 4.00 × 10−3 0.59 0.66

Note: Fold change (FC) is based on comparing the mass intensity of metabolites between ZJT and YKT; metabolite marked with * is confirmed by standards.