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. 2021 Jan 31;26(3):731. doi: 10.3390/molecules26030731

Table 2.

The list of tentatively identified metabolites in the by-product seed extracts by Ultra Performance Liquid Chromatography equipped with Electron Spray Ionization source coupled with High Resolution Mass Spectrometer UPLC-ESI-HRMS/MS-orbitrap.

Grape Seed Paste By-Product
Proposed Compound Rt (min) EC m/z exp. Delta
(ppm)		 RDB Ref. Extract (Peak Area × 106)
SFE-CO2 UAE
10% EtOH 20% EtOH EtOH EtOH/H2O
Gluconic acid 0.59 C6H12O7 195.0515 2.73 1.5 [37] 4.25 1.98 3.19 1.83
Tartaric acid 0.71 C4H6O6 149.0097 3.62 2.5 [37] 2.21 13.1 1.37 0.91
Citric acid 0.91 C6H8O7 191.0202 2.59 3.5 [37] 1.19 12.2 1.58 1.67
Gallic acid 1.35 C7H6O5 169.0147 2.62 5.5 [37] 18.0 18.1 5.96 1.77
Glucogallin 2.84 C13H16O10 331.0673 0.57 6.5 [38] 3.07 19.5 4.76 1.08
Epicat./cat. 4.96 C15H14O6 289.0723 1.97 9.5 [39] 0.04 40.3 32.7 48.2
Epicat./cat. 5.35 C15H14O6 289.0722 1.41 9.5 [39] 0.09 64.1 43.4 61.2
Epicat. galate 6.33 C22H18O10 441.0832 1.07 14.5 [39] - 16.1 5.58 9.27
Dimer proanth 4.79 C30H26O12 577.1348 0.51 18.5 [40] - 10.6 15.1 23.6
5.20 C30H26O12 577.1361 1.67 18.5 [40] - 12.2 13.4 20.1
5.30 C30H26O12 577.1360 1.47 18.5 [40] - 8.78 35.6 52.3
Dimer proanth gall 5.58 C37H30O16 729.1470 1.18 23.5 [41] 1.51 1.04 1.67
5.80 C37H30O16 729.1468 0.94 23.5 [41] - 7.51 18.8 27.3
Trimer proanth 4.92 C45H38O18 865.1979 −0.56 27.5 [42] - 0.36 1.89 2.74
5.07 C45H38O18 865.1986 0.09 27.5 [42] - 0.72 2.01 2.81
5.37 C45H38O18 865.1985 0.36 27.5 [42] - 1.52 3.12 4.45
5.67 C45H38O18 865.1984 −0,12 27.5 [42] - 2.41 5.26 7.56
6.14 C45H38O18 865.1989 0.50 27.5 [42] - 0.61 5.67 7.64
Trimer proanth.-gall 5.37 C52H47O22 1017.2103 0.76 32.5 [42] - - 1.35 2.27
5.77 C52H47O22 1017.2093 −0.20 32.5 [42] - - 1.53 2.46
6.30 C52H47O22 1017.2098 0.28 32.5 [42] - - 1.97 3.44
Tetramer proanth. 5.11 C60H49O24 1153.2622 0.25 36.5 [43] - - 0.48 1.05
5.61 C60H49O24 1153.2630 0.98 36.5 [43] - - 0.69 1.17
5.75 C60H49O24 1153.2621 0.13 36.5 [43] - - 1.36 2.36
6.01 C60H49O24 1153.2613 −0.50 36.5 [43] - - 0.66 1.17
Pomegranate Seed Paste By-Product
Proposed Compound Rt (min) EC m /z exp. Delta
(ppm) 		RDB Ref. Extract (Peak Area × 106)
SFE-CO2 UAE
10% EtOH 20% EtOH EtOH EtOH/H2O
Gulonic acid 0.60 C6H11O7 195.0514 1.713 1.5 [44] 19.9 45.9 27.9 24.7
Glucopyranose 0.67 C6H11O6 179.0565 2.171 1.5 [45] 29.2 31.3 18.2 16.8
Gallic acid 1.37 C7H5O5 169.0149 3.748 5.5 [44] 1.84 3.97 2.36 1.38
Quinic acid 1.42 C7H11O6 191.0566 2.505 2.5 [44] 2.01 - 0.33 -
Protocatechuic acid 2.73 C7H5O4 153.0199 3.712 5.5 [45] 3.31 2.04 1.63 0.86
4-Hydroxybenzoic acid 4.30 C7H5O3 137.0251 4.753 5.5 [45] 5.48 0.04 1.53 0.43
Vanillic acid 5.01 C8H7O4 167.03552 3.221 5.5 [44] 1.14 0.07 0.38 0.13
Couma ric acid 5.91 C9H7O3 163.04056 3.021 6.5 [46] 0.75 0.10 0.11 0.14
Kaempferol 8.60 C15H9O6 285.04089 1.504 11.5 [46] 0.33 0.23 0.09 0.04
Asiatic acid 11.08 C30H47O5 487.34357 1.379 7.5 [46] 2.06 - 1.49 0.50
Hemp Seed Paste By-Product
Proposed Compound Rt (min) EC m /z exp. Delta
(ppm) 		RDB Ref. Extract (Peak Area × 106)
SFE-CO2 UAE
10% EtOH 20% EtOH EtOH EtOH/H2O
Hydroxybenzoic acid 7.05 C7H5O3 137.0251 4.613 5.5 [47] 80.9 70.1 2.42 12.4
Cannabinolic acid 12.93 C22H25O4 353.1764 1.578 10.5 [48] 3.99 0.60 0.32 0.28
Cannabichromevarinic acid 13,31 C20H25O4 329.1762 1.056 8.5 [47] 5.81 0.25 0.83 0.63
Caffeoyl tyramine
isomer I 		6.65 C17H16O4N 298.1086 0.633 10.5 [47] 16.5 122.3 7.62 13.7
Caffeoyl tyramine
isomer II 		6.91 C17H16O4N 298.1084 −0.273 10.5 [47] 20.9 112.1 11.5 26.3
Cannabisin A 7.40 C34H29O8N2 593.1927 0.319 21.5 [49] - 9.50 3.97 5.54
Cannabisin B
isomer I 		7.43 C34H31O8N2 595.2086 0.049 20.5 [50] 0.37 42.1 11.2 22.1
Cannabisin B
isomer II 		8.76 C34H31O8N2 595.2089 0.657 20.5 [50] 0.49 28.5 3.74 5.69
Cannabisin C 7.85 C35H33O8N2 609.2243 0.100 20.5 [50] 1.24 57.5 3.05 9.65
Cannabidiolic acid 14.34 C22H29O4 357.2073 0.496 8.5 [48] 93.2 7.16 27.2 13.2
(±)-6,7-cis/trans-epoxy cannabigerolic acid 12.41 C22H31O5 375.2164 −0.454 7.5 [51] 0.76 0.08 0.09 0.20
α / β -cannabielsoic acid
isomer I 		11.29 C22H29O5 373.2022 0.516 8.5 [51] 10.4 1.73 0.93 0.67
α / β -cannabielsoic acid
isomer II 		12.47 C22H29O5 373.2023 0.758 8.5 [51] 8.43 1.37 0.51 0.62
α / β -cannabielsoic acid
isomer III 		13.60 C22H29O5 373.2027 0.918 8.5 23.6 5.38 2.26 2.01
Fennel Seed Paste By-Product
Proposed Compound Rt (min) EC m/z exp. Delta
(ppm) 		RDB Ref. Extract (Peak Area × 106)
SFE-CO2 UAE
10% EtOH 20% EtOH EtOH EtOH/H2O
Malic acid 0.64 C4H5O5 133.0147 4.086 2.5 [52] 1.56 17.0 4.32 50.9
Quercetin-O-Glucuronide 6.35 C21H17O13 477.0675 0.034 13.5 [52] - 20.8 9.61 35.5
Chlorogenic acid 5.02 C16H17O9 353.0881 0.551 8.5 [52] 0.05 12.7 6.45 6.87
Kaempferol-O-Glucuronoside 6.70 C21H17O12 461.073 0.978 13.5 [53] - 6.46 3.13 6.45
2-(Hydroxymethyl)-1,2,3,4-butanetetrol or deoxytetritol 0.61 C5H11O5 151.06163 2.868 0.5 [53] 2.21 1.21 0.92 0.43
Casearicoside A 5.17 C18H25O11 417.1408 1.235 6.5 [54] 11.9 16.7 27.9 2.07
Myristicin * 5.15 C11H13O3 193.08562 −1.558 5.5 [54] 26.4 - 44.6 2.97
2,4-Thujanediol * 6.37 C10H19O2 171.13763 −1.907 1.5 [54] 22.6 - 37.8 3.14
Isorhamnetin 8.77 C16 H11O7 315.0513 0.965 11.5 [55] 0.41 0.23 0.39 -
Naringenin 8.17 C15 H11O5 271.0613 0.418 10.5 [53] 0.33 0.09 0.29 -
Rosmarinic acid 7.56 C18 H15O8 359.0775 0.862 11.5 [55] 0.09 0.38 1.57 -

* Ionization in positive mode.