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. 2021 Feb 4;10(2):234. doi: 10.3390/antiox10020234

Table 3.

Qualitative characterization of phenolic compounds in stone fruits waste by Liquid chromatography coupled with electrospray-ionization quadrupole time-of-flight mass spectrometry (LC-ESI-QTOF-MS/MS).

No. Compound
Name		 Moleular
Formula		 RT
(min)		 Ionization
(ESI−/ESI+)		 Molecular Weight Theoretical Weight (m/z) Observed Weight (m/z) Error (ppm) MS/MS Product Ions Samples
Phenolic acids
Hydroxycinnamic acids
1 1,5-Dicaffeoylquinic acid C25H24O12 4.134 [M − H]− 516.1268 515.1195 515.1198 0.6 353, 335, 191, 179 NE
2 Isoferulic acid 3-sulfate C10H10O7S 5.341 [M − H]− 274.0147 273.0074 273.0067 −2.6 193, 178 PL
3 Cinnamic acid C9H8O2 9.317 [M − H]− 148.0524 147.0451 147.0449 −1.4 103 NE, *AP, PL
4 Caffeoyl glucose C15H18O9 14.833 [M − H]− 342.0951 341.0878 341.0887 2.6 179, 161 NE, *PL
5 p-Coumaric acid 4-O-glucoside C15H18O8 14.953 [M − H]− 326.1002 325.0929 325.0926 −0.9 163 *PE, PL
6 3-Caffeoylquinic acid C16H18O9 20.038 [M − H]− 354.0951 353.0878 353.0864 −4.0 253, 190, 144 *NE, AP, PE, PL
7 3-Feruloylquinic acid C17H20O9 20.817 [M − H]− 368.1107 367.1034 367.1023 −3.0 298, 288, 192, 191 NE, AP, *PE, PL
8 Ferulic acid 4-O-glucuronide C16H18O10 22.305 [M − H]− 370.0900 369.0827 369.0826 −0.3 193 AP, *PL
9 Ferulic acid C10H10O4 23.467 [M − H]− 194.0579 193.0506 193.0501 −2.6 178, 149, 134 *NE, PL, AP
10 Ferulic acid 4-O-glucoside C16H20O9 23.500 [M − H]− 356.1107 355.1034 355.1032 −0.6 193, 178, 149, 134 *NE, AP, PL
11 3-p-Coumaroylquinic acid C16H18O8 27.013 [M − H]− 338.1002 337.0929 337.0918 −3.3 265, 173, 162 PL, *PE, AP, NE
12 m-Coumaric acid C9H8O3 27.808 [M − H]− 164.0473 163.0400 163.0394 −3.7 119 *NE, AP, PE, PL
13 Caffeic acid C9H8O4 32.032 [M − H]− 180.0423 179.0350 179.0347 −1.7 143, 133 *NE, PL
14 1-Sinapoyl-2-feruloylgentiobiose C33H40O18 36.370 [M − H]− 724.2215 723.2142 723.2124 −2.5 529, 499 AP
15 Hydroxycaffeic acid C9H8O5 37.033 [M − H]− 196.0372 195.0299 195.0298 −0.5 151 PE, *PL
16 3-Sinapoylquinic acid C18H22O10 41.574 [M − H]− 398.1213 397.1140 397.1129 −2.8 233, 179 NE
Hydroxybenzoic acids
17 Ellagic acid acetyl-xyloside C21H16O13 4.101 [M − H]− 476.0591 475.0518 475.0498 −4.2 301 PE
18 Gallic acid 4-O-glucoside C13H16O10 6.914 [M − H]− 332.0743 331.0670 331.0675 1.5 169, 125 *PL, AP
19 Protocatechuic acid 4-O-glucoside C13H16O9 7.382 [M − H]− 316.0794 315.0721 315.0732 3.5 153 *PE, APt, PL
20 2-Hydroxybenzoic acid C7H6O3 20.237 [M − H]− 138.0317 137.0244 137.0240 −2.9 93 *NE, AP, PE
21 2,3-Dihydroxybenzoic acid C7H6O4 32.082 [M − H]− 154.0266 153.0193 153.0190 −2.0 109 *NE, PE, PL
22 3-O-Methylgallic acid C8H8O5 84.390 **[M + H]+ 184.0372 185.0445 185.0450 2.7 170, 142 PE
Hydroxyphenylpropanoic acids
23 Dihydroferulic acid 4-O-glucuronide C16H20O10 5.689 [M − H]− 372.1056 371.0983 371.0988 1.3 195 NE, AP, *PL
24 3-Hydroxy-3-(3-hydroxyphenyl)propionic acid C9H10O4 7.083 [M − H]− 182.0579 181.0506 181.0511 2.8 163, 135, 119 PE
25 Dihydrocaffeic acid 3-O-glucuronide C15H18O10 17.454 [M − H]− 358.0900 357.0827 357.0819 −2.2 181 PE
Hydroxyphenylacetic acids
26 3,4-Dihydroxyphenylacetic acid C8H8O4 20.715 [M − H]− 168.0423 167.0350 167.0344 −3.6 149, 123 NE, *AP, PE, PL
Flavonoids
Flavonols
27 Isorhamnetin C16H12O7 27.076 [M − H]− 316.0583 315.0510 315.0504 −1.9 300, 271 PL
28 Myricetin 3-O-rutinoside C27H30O17 32.960 [M − H]− 626.1483 625.1410 625.1399 −1.8 301 *NE, PE
29 Quercetin 3-O-glucosyl-xyloside C26H28O16 34.730 [M − H]− 596.1377 595.1304 595.1290 −2.4 265, 138, 116 NE, *PL
30 Kaempferol 3,7-O-diglucoside C27H30O16 37.284 [M − H]− 610.1534 609.1461 609.1445 −2.6 447, 285 *NE, AP, PE, PL
31 Myricetin 3-O-rhamnoside C21H20O12 39.355 [M − H]− 464.0955 463.0882 463.0874 −1.7 317 *NE, PE, PL
32 Kaempferol 3-O-glucosyl-rhamnosyl-galactoside C33H40O20 40.283 [M − H]− 756.2113 755.2040 755.2064 3.2 285 *PE, PL
33 Kaempferol 3-O-(2″-rhamnosyl-galactoside) 7-O-rhamnoside C33H40O19 42.036 [M − H]− 740.2164 739.2091 739.2106 2.0 593, 447, 285 AP, *PL
34 Quercetin 3-O-arabinoside C20H18O11 42.798 [M − H]− 434.0849 433.0776 433.0772 −0.9 301 PE, *PL
Flavanols
35 Procyanidin dimer B1 C30H26O12 17.139 [M − H]− 578.1424 577.1351 577.1342 −1.6 451 NE, *PE, PL
36 Procyanidin trimer C1 C45H38O18 19.177 [M − H]− 866.2058 865.1985 865.1959 −3.0 739, 713, 695 *PE, PL
37 Cinnamtannin A2 C60H50O24 19.422 [M − H]− 1154.2692 1153.2619 1153.2609 −0.9 739 PL
38 (+)-Catechin C15H14O6 19.704 [M − H]− 290.0790 289.0717 289.0717 0.0 245, 205, 179 *AP, PL, PE
39 4′-O-Methyl-(-)-epigallocatechin 7-O-glucuronide C22H24O13 32.112 [M − H]− 496.1217 495.1144 495.1138 −1.2 451, 313 NE, PE, *PL
Flavones
40 Apigenin 7-O-(6″-malonyl-apiosyl-glucoside) C29H30O17 4.416 [M − H]− 650.1483 649.1410 649.1429 2.9 605 PE
41 Apigenin 6,8-di-C-glucoside C27H30O15 43.461 [M − H]− 594.1585 593.1512 593.1500 −2.0 503, 473 *AP, PE, PL
42 6-Hydroxyluteolin 7-O-rhamnoside C21H20O11 46.460 [M − H]− 448.1006 447.0933 447.0938 1.1 301 *AP, PE, PL
43 Apigenin 6-C-glucoside C21H20O10 55.256 [M − H]− 432.1056 431.0983 431.0984 0.2 413, 341, 311 PL
Isoflavonoids
44 6″-O-Acetyldaidzin C23H22O10 4.413 [M − H]− 458.1213 457.1140 457.1125 −3.3 221 PL
45 Violanone C17H16O6 20.267 [M − H]− 316.0947 315.0874 315.0868 −1.9 300, 285, 135 PL
46 3′-Hydroxydaidzein C15H10O5 81.970 [M + H]+ 270.0528 271.0601 271.0610 3.3 253, 241, 225 AP
Flavanones
47 Neoeriocitrin C27H32O15 34.931 [M − H]− 596.1741 595.1668 595.1650 −3.0 431, 287 NE
48 Narirutin C27H32O14 41.624 [M − H]− 580.1792 579.1719 579.1696 −4.0 271 NE
49 Hesperetin 3′-O-glucuronide C22H22O12 46.562 [M − H]− 478.1111 477.1038 477.1044 1.3 301, 175, 113, 85 NE, *PE
Dihydroflavonols
50 Dihydroquercetin C15H12O7 5.775 [M − H]− 304.0583 303.0510 303.0507 −1.0 285, 275, 151 PE
51 Dihydromyricetin 3-O-rhamnoside C21H22O12 23.846 [M − H]− 466.1111 465.1038 465.1050 2.6 301 *NE, PE, PL
52 Dihydroquercetin 3-O-rhamnoside C21H22O11 27.029 [M − H]− 450.1162 449.1089 449.1069 −4.5 303 NE
Anthocyanins
53 Cyanidin 3-O-(2-O-(6-O-(E)-caffeoyl-D glucoside)-D-glucoside)-5-O-D-glucoside C43H49O24 39.482 [M + H]+ 949.2614 950.2687 950.2676 −1.2 787, 463, 301 PE
Dihydrochalcones
54 Phloridzin C21H24O10 51.681 [M − H]− 436.1369 435.1296 435.1307 2.5 273 PE
Lignans
55 7-Hydroxymatairesinol C20H22O7 41.309 [M − H]− 374.1366 373.1293 373.1298 1.3 343, 313, 298, 285 NE
Other polyphenols
Hydroxybenzaldehydes
56 4-Hydroxybenzaldehyde C7H6O2 44.769 [M − H]− 122.0368 121.0295 121.0298 2.5 77 PE, *PL
57 p-Anisaldehyde C8H8O2 55.681 **[M + H]+ 136.0524 137.0597 137.0599 1.5 122, 109 NE, AP, PE, *PL
Hydroxycoumarins
58 Scopoletin C10H8O4 36.851 [M − H]− 192.0423 191.0350 191.0345 −2.6 176 AP
Tyrosols
59 3,4-DHPEA-AC C10H12O4 11.802 [M − H]− 196.0736 195.0663 195.0657 −3.1 135 AP

* Compound was detected in more than one stone fruit samples, data presented in this table are from asterisk sample. ** Compounds were detected in both negative [M − H]− and positive [M + H]+ mode of ionization while only single mode data are presented. RT refers to retention time. Stone fruits samples mentioned in abbreviations are Peach “PE”, Plum “PL”, Apricot “AP’’, and Nectarine “NE”.