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. 2021 Nov 8;26(21):6750. doi: 10.3390/molecules26216750

Table 2.

UFLC/Q-TOF-MS data and identification 94 compounds from red wine.

Peak No. RT (min) Ion Found at Mass MS/MS Fragmentation Ions Formula Identification ppm
1 0.70 [M+H]+ 116.0702 70.0647 C5H9NO2 D-proline 0.8
2 0.76 [M+H]+ 175.1189 70.0652 C6H14N4O2 L-arginine −0.3
3 0.79 [M−H]− 179.0562 99.0087, 71.0137, 59.0139 C6H12O6 D-glucose 0.3
4 0.88 [M-H]− 181.0720 83.0143, 71.0140, 59.0140 C6H14O6 D-mannitol 1.5
5 0.96 [M−H]− 191.0199 85.0296, 59.0134 C6H8O7 citric acid 1.0
6 0.99 [M−H]− 149.0091 105.0217, 87.0085, 72.9928 C4H6O6 tartaric acid −0.7
7 1.04 [M+H]+ 138.0548 120.0433, 92.0495, 78.0339 C7H7NO2 4-aminobenzoic acid −1.5
8 1.12 [M−H]− 341.1088 161.0459, 71.0137, 59.0138 C12H22O11 trehalose −0.3
9 1.15 [M−H]− 149.0455 75.0221, 59.0133 C5H10O5 D-ribose −0.2
10 1.31 [M−H]− 133.0142 115.0018, 71.0136 C4H6O5 L-malic acid −0.5
11 1.33 [M+H]+ 118.0862 72.0809 C5H11NO2 L-valine −0.4
12 1.48 [M−H]− 173.0454 137.0225, 93.0343 C7H10O5 shikimic acid −1.0
13 1.71 [M+H]+ 150.0586 74.0243, 61.0108 C5H11NO2S L-methionine 1.8
14 2.03 [M+H]+ 124.0393 80.0506, 55.9346 C6H5NO2 niacin 0.2
15 3.27 [M−H]− 117.0192 99.9254, 73.0291 C4H6O4 succinic acid −1.2
16 3.51 [M+H]+ 165.0547 119.0479, 95.0503, 77.0388, 59.9302 C9H8O3 trans-4-hydroxycinnamic acid 0.7
17 3.85 [M+H]+ 137.0913 121.0616, 103.0616, 95.0561, 91.0556, 77.0391 C8H11NO tyramine −0.5
18 5.97 [M−H]− 169.0141 125.0244, 107.0156, 79.0186 C7H6O5 gallic acid −1.0
19 8.77 [M+H]+ 141.0182 123.0080, 95.0127, 67.0187, 55.9453 C6H4O4 coumalic acid −0.1
20 11.49 [M−H]− 153.0558 123.0085, 108.0221, 95.0139, 78.9590 C8H10O3 hydroxytyrosol 0.2
21 11.57 [M−H]− 153.0194 109.0298, 91.0298, 65.0029 C7H6O4 protocatechuic acid 0.3
22 13.85 [M−H]− 305.0664 179.0360, 165.0194, 137.0243, 125.0246 C15H14O7 (+)-gallocatechin −1.0
23 14.27 [M−H]− 179.0349 135.0560, 89.0394, 79.0550 C9H8O4 acetylsalicylic acid −0.7
24 14.27 [M−H]− 179.0348 161.0263, 135.0454, 117.0351 C13H12O9 caftaric acid −1.0
25 15.05 [M−H]− 153.0194 123.0061, 109.0298, 91.0298 C7H6O4 gentisic acid 0.4
26 15.21 [M−H]− 137.0255 108.0213 C7H6O3 protocatechualdehyde −2.7
27 15.31 [M−H]− 181.0506 135.0453 C9H10O4 homovanillic acid 0.0
28 15.43 [M−H]− 183.0299 124.0234, 95.0136 C8H8O5 methyl gallate 0.0
29 15.90 [M−H]− 137.0244 93.0340 C7H6O3 4-hydroxybenzoic acid 0.4
30 16.32 [M−H]− 353.0877 191.0616, 179.0341, 135.0439 C16H18O9 chlorogenic acid −0.2
31 17.36 [M−H]− 295.0458 163.0400, 119.0503, 87.0094 C13H12O8 p-coutaric acid 0.1
32 18.08 [M−H]− 163.0401 119.0498, 93.0347 C9H8O3 m-coumaric acid 0.2
33 18.08 [M−H]− 295.0458 163.0400, 119.0498 C13H12O8 coutaric acid −0.4
34 18.15 [M−H]− 145.0507 73.0273, 55.0191 C6H10O4 dimethyl succinate 0.6
35 19.24 [M−H]− 121.0296 108.0212, 92.0265 C7H6O2 benzoic acid 0.8
36 19.66 [M−H]− 577.1346 425.0864, 407.0775, 289.0714, 161.0238, 125.0243 C30H26O12 procyanidin B1 −0.9
37 19.89 [M−H]− 305.0664 245.0462, 219.0652, 139.0401, 125.0244 C15H14O7 (−)-epigallocatechin 0.2
38 19.98 [M−H]− 577.1346 407.0768, 289.0709 C30H26O12 procyanidin B3 0.0
39 20.01 [M−H]− 167.0350 108.0212 C8H8O4 vanillic acid 0.2
40 20.21 [M−H]− 163.0400 119.0502, 93.0343 C9H8O3 2-Hydroxycinnamic acid −0.1
41 20.47 [M−H]− 289.0713 245.0843, 203.0713, 151.0401, 109.0294 C15H14O6 catechin −1.5
42 20.58 [M−H]− 325.0563 193.0490, 117.0341 C14H14O9 fertaric acid −0.5
43 20.98 [M−H]− 179.0349 135.0449, 89.0393 C9H8O4 caffeic acid −1.0
44 21.90 [M−H]− 441.0186 289.0735, 217.0167, 191.0337, 151.0386 C22H18O10 epicatechin gallate 2.2
45 22.06 [M−H]− 197.0454 182.0256, 167.0014, 138.0317, 123.0090, 95.0142 C9H10O5 syringic acid −0.3
46 23.01 [M−H]− 577.1346 425.0893, 407.0782, 289.0721 C30H26O12 procyanidin B2 −0.7
47 23.11 [M−H]− 325.0926 163.0394, 145.0294, 117.0343 C15H18O8 p-coumaric acid glucoside −0.5
48 23.37 [M−H]− 189.0769 71.0503 C8H14O5 diethyl malate 0.3
49 23.69 [M−H]− 165.0556 119.0527, 103.0565 C9H10O3 desaminotyrosine −0.5
50 24.37 [M−H]− 137.0244 93.0470, 65.0473 C7H6O3 2-hydroxybenzoic acid 2.2
51 24.38 [M−H]− 289.0713 203.0710, 187.0396, 151.0401, 123.0449, 109.0290 C15H14O6 epicatechin −0.7
52 24.68 [M−H]− 167.0350 123.0436, 108.0212 C8H8O4 3-hydroxy-4-methoxybenzoic acid 2.5
53 25.16 [M−H]− 197.0454 169.0142, 125.0239, 79.0184 C9H10O5 ethyl gallate −0.9
54 25.32 [M]+ 493.1341 331.0822, 316.0553 C23H25O12 malvidin-3-O-glucoside 0.1
55 25.74 [M−H]− 163.0401 119.0503, 93.0347 C9H8O3 p-coumaric acid −0.6
56 30.75 [M−H]− 167.0350 123.0450, 65.0024 C8H8O4 homogentisic acid 0.8
57 30.80 [M−H]− 577.1346 425.0886, 407.0789, 289.0734 C30H26O12 procyanidin B7 0.6
58 34.06 [M−H]− 479.0826 316.0225, 271.0249, 151.0034 C21H20O13 myricetin-3-O-galactoside −1.0
59 35.93 [M−H]− 389.1242 227.0716, 185.0606, 143.0505 C20H22O8 trans-piceid −0.2
60 38.70 [M−H]− 300.9987 257.011, 229.0126, 145.0295 C14H6O8 ellagic acid −0.9
61 38.84 [M−H]− 181.0506 109.0286, 65.0032 C9H10O4 dihydrocaffeic acid 0.5
62 39.28 [M]+ 465.1036 303.051, 229.0488 C21H21O12 delphinidin-3-O-glucoside 1.9
63 39.31 [M−H]− 463.0884 301.0379, 271.0245, 243.0291, 151.0031 C21H20O12 hyperoside 0.4
64 39.71 [M−H]− 449.1090 285.0413, 151.0041 C21H22O11 quercitrin 0.2
65 39.83 [M]+ 627.1462 303.0351 C27H31O17 delphinidin-3,5-O-diglucoside 1.1
66 40.08 [M−H]− 477.0670 301.0352, 255.0296, 151.0034 C21H18O13 quercetin-3-O-glucuronide −0.9
67 41.28 [M−H]− 493.0985 330.0381, 315.0155, 271.0249, 151.0034 C22H22O13 laricitrin-3-O-glucoside −0.6
68 42.86 [M−H]− 447.0936 301.0372, 271.0256, 255.0295, 151.0020 C21H20O11 luteolin -3’-glucoside 1.2
69 42.98 [M−H]− 449.1090 285.0413, 151.0041 C21H22O11 astilbin 0.9
70 43.45 [M−H]− 463.0884 301.0379, 255.0305, 151.0039 C21H20O12 isoquercitrin 0.8
71 44.78 [M−H]− 447.0936 301.0372, 255.0293, 151.0016 C21H20O11 astragalin 0.8
72 45.19 [M−H]− 389.1242 227.0994, 185.0606 C20H22O8 cis-piceid 0.0
73 45.72 [M−H]− 317.0300 245.0504, 137.0241, 109.0292, 151.0035 C15H10O8 myricetin −0.9
74 45.77 [M]+ 479.1193 317.0648, 302.0429, 285.0362, 153.0184 C22H23O12 petunidin-3-O-glucoside 1.9
75 45.80 [M−H]− 477.1041 315.0530, 300.0263, 271.0255, 243.0306, 151.0036 C22H22O12 isorhamnetin-3-O-glucoside 0.6
76 47.17 [M−H]− 227.0715 185.0587, 143.0501, 115.0556 C14H12O3 trans-resveratrol 0.6
77 47.42 [M−H]− 435.1300 273.0769, 179.0349, 167.0352 C21H24O10 phloridzin 0.7
78 49.16 [M]+ 507.1141 303.0767, 187.0626, 113.0234 C23H23O13 delphindin-3-O-(6-O-acetylglucoside) 1.6
79 51.13 [M−H]− 207.0662 179.0433, 135.0446 C11H12O4 ethyl caffeate −0.6
80 51.94 [M]+ 639.1719 477.1176, 419.0853, 331.0874 C32H31O14 malvidin-3-O-(6-O-coumaroylglucoside) 1.7
81 52.60 [M+H]+ 303.0497 285.0398, 257.0456, 229.0492, 153.0188 C15H10O7 morin −0.8
82 52.60 [M]+ 303.0497 229.0492, 153.0188 C15H11O7 delphinidin −0.8
83 52.63 [M−H]− 301.0351 245.0447, 229.0513, 151.0034, 121.0292 C15H10O7 quercetin −1.0
84 52.67 [M−H]− 227.0715 143.0504 C14H12O3 resveratrol −0.9
85 53.23 [M−H]− 331.0459 316.0231, 271.0251, 178.9991, 151.0039 C16H12O8 laricitrin 0.0
86 55.82 [M−H]− 271.0613 229.0500, 177.0190, 151.0048, 119.0618 C15H12O5 naringenin 0.4
87 57.10 [M]+ 287.0549 213.0559, 153.0180, 137.0233 C15H11O6 cyanidin −0.3
88 57.12 [M−H]− 285.0403 239.0356, 187.0403, 151.004 C15H10O6 kamepferol −0.6
89 57.32 [M−H]− 345.0618 330.0385, 315.0153, 259.0252, 187.0394 C17H14O8 syringetin 0.6
90 57.39 [M]+ 317.0656 229.0498, 153.0188 C16H13O7 petunidin 0.0
91 57.41 [M−H]− 315.0508 300.0270, 271.0241, 255.0299, 227.0241, 151.0036 C16H12O7 isorhamnetin −0.6
92 58.32 [M+H]+ 193.1588 56.9419 C13H20O ionone 0.6
93 60.04 [M+H]+ 173.1536 76.0221 C10H20O2 ethyl caprylate 0.2
94 60.96 [M+H]+ 195.1748 177.1634, 107.0855, 77.0387 C13H22O theaspirane 2.1