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. 2021 Nov 5;10(11):1770. doi: 10.3390/antiox10111770

Table 3.

Characterization of polyphenolic compounds from Australian-grown herbs by LC-MS/MS-QTOF.

No Proposed Compounds Molecular Formula RT
(min)		 Ionization
ESI (+/−)		 Molecular Weight Theoretical (m/z) Observed
(m/z)		 Mass Error
(ppm)		 MS/MS Product Ions Herbs
Phenolic acids
Hydroxybenzoic acids
1 Gallic acid C7H6O5 10.544 [M − H]− 170.0215 169.0142 169.0144 0.3 125 * Bl, M
2 3-O-Methylgallic acid C8H8O5 10.632 [M − H]− 184.0372 183.0299 183.0294 −2.7 168, 140, 124 T
3 Gallic acid 4-O-glucoside C13H16O10 10.713 [M − H]− 332.0743 331.0670 331.0662 −2.4 169, 125 * T, By
4 3,4-O-Dimethylgallic acid C9H10O5 12.632 ** [M + H]+ 198.0528 199.0601 199.0595 3.0 153, 139, 125, 111 * Bl, M, R, S, T
5 Protocatechuic acid 4-O-glucoside C13H16O9 12.620 [M − H]− 316.0794 315.0721 315.0716 −1.6 153 * R, T, M, Bl
6 2,3-Dihydroxybenzoic acid C7H6O4 14.097 [M − H]− 154.0266 153.0193 153.0186 −4.6 109 * R, M, T, Bl
7 4-Hydroxybenzoic acid 4-O-glucoside C13H16O8 16.006 [M − H]− 300.0845 299.0772 299.0756 −0.7 255, 137 * Bl, T, S
8 2-Hydroxybenzoic acid C7H6O3 17.155 [M − H]− 138.0317 137.0244 137.0238 −0.6 93 * T, R, M, S, By, Bl, O
Hydroxycinnamic acids
9 Caffeoyl glucose C15H18O9 14.513 [M − H]− 342.0951 341.0878 341.0877 −0.3 179, 161 * T, R, Bl
10 Caffeoyl tartaric acid C13H12O9 15.864 [M − H]− 312.0481 311.0408 311.0401 −2.3 161 * M, Bl
11 3-p-Coumaroylquinic acid C16H18O8 16.456 [M − H]− 338.1002 337.0929 337.0929 0.0 265, 173, 162 * M, R, S
12 p-Coumaric acid 4-O-glucoside C15H18O8 16.984 [M − H]− 326.1002 325.0929 325.0917 −3.7 163 * T, Bl
13 3-Caffeoylquinic acid C16H18O9 17.680 [M − H]− 354.0951 353.0878 353.0870 −2.3 253, 190, 144 * T, M, R, S, Bl
14 3-Feruloylquinic acid C17H20O9 17.858 [M − H]− 368.1107 367.1034 367.1032 −0.5 298, 288, 192, 191 M
15 Sinapic acid C11H12O5 18.318 [M + H]+ 224.0685 225.0758 225.0760 0.9 193, 179, 149 134, Bl, O
16 m-Coumaric acid C9H8O3 20.039 ** [M − H]− 164.0473 163.0400 163.0405 3.1 119 * Bl, R, O, S, By
17 Ferulic acid 4-O-glucoside C16H20O9 20.816 [M − H]− 356.1107 355.1034 355.1028 −1.7 193, 178, 149, 134 * R, S
18 Feruloyl tartaric acid C14H14O9 21.620 [M − H]− 326.0638 325.0565 325.0542 −4.6 193, 149 * S, M, Bl
19 Caffeic acid C9H8O4 21.084 [M − H]− 180.0423 179.0350 179.0345 −1.7 161, 135 * Bl, R, M, O, S, T
20 Ferulic acid C10H10O4 21.595 [M − H]− 194.0579 193.0506 193.0501 −2.6 178, 149, 134 * S, Bl
21 p-Coumaroyl tartaric acid C13H12O8 20.039 ** [M − H]− 296.0532 295.0459 295.0446 −1.7 115 * Bl, S
22 Chicoric acid C22H18O12 30.115 ** [M − H]− 474.0798 473.0725 473.0736 2.3 293, 311 Bl
23 Rosmarinic acid C18H16O8 33.487 [M − H]− 360.0845 359.0772 359.0754 −3.2 179, 161, 135 * R, T, M, S, O, Bl, By
24 Cinnamoyl glucose C15H18O7 42.212 [M − H]− 310.1053 309.0980 309.0995 4.9 147, 131, 103 * T, M, O, R, S
Hydroxyphenyl acetic acids
25 3,4-Dihydroxyphenylacetic acid C8H8O4 12.532 [M − H]− 168.0423 167.0350 167.0349 −0.6 149, 123 * R, M, T, Bl
Hydroxyphenylpentanoic acids
26 5-(3′,4′,-dihydroxyphenyl)-γ-valerolactone C11H12O4 41.689 [M − H]− 208.0736 207.0663 207.0653 −4.8 163, 119 S
Hydroxyphenylpropanoic acids
27 3-Hydroxy-3-(3-hydroxyphenyl)propionic acid C9H10O4 14.984 [M − H]− 182.0579 181.0506 181.0512 3.3 163, 135, 119 * T, S
28 Dihydroferulic acid 4-O-glucuronide C16H20O10 22.759 [M − H]− 372.1056 371.0983 371.1014 3.4 195 * T, R, S
Flavonoids
Flavanols
29 (+)-Gallocatechin C15H14O7 16.244 [M − H]− 306.0740 305.0667 305.0639 −4.3 261, 219 * By, S
30 (+)-Catechin C15H14O6 21.158 [M − H]− 290.0790 289.0710 289.0701 −0.3 245, 205, 179 By
31 3′-O-Methyl-(−)-epicatechin-7-O-glucuronide C22H24O12 25.668 [M − H]− 480.1268 479.1195 479.1184 −2.3 149, 121 R
32 4′-O-Methyl-(−)-epigallocatechin-7-O-glucuronide C22H24O13 28.364 [M − H]− 496.1217 495.1144 495.1155 2.2 451, 313 T
33 Chrysoeriol 7-O-glucoside C22H22O11 40.831 [M − H]− 462.1162 461.1089 461.1075 −3.0 299, 285 * R, S, By
Flavones
34 Apigenin 6,8-di-C-glucoside C27H30O15 20.343 [M − H]− 594.1585 593.1512 593.1515 0.5 503, 473 * R, M, By
35 Apigenin 6-C-glucoside C21H20O10 27.103 [M − H]− 432.1056 431.0983 431.0979 −0.9 413, 341, 311 * T, R, S, By
36 6-Hydroxyluteolin 7-O-rhamnoside C21H20O11 28.258 ** [M−H]− 448.1006 447.0933 447.0926 −1.6 301 * R, M, S, T, D, By, Bl, F
37 Luteolin 7-O-glucuronide C21H18O12 28.447 [M − H]− 462.0798 461.0725 461.0716 −2.4 285, 216 * M, T, R, S, O
38 Rhoifolin C27H30O14 30.045 [M − H]− 578.1636 577.1563 577.1525 −4.3 413, 269 * R, M, S, D, F
39 Apigenin 7-O-glucuronide C21H18O11 32.538 [M − H]− 446.0849 445.0776 445.0765 −3.5 269, 175 * T, R, S
Flavanones
40 Neoeriocitrin C27H32O15 25.227 [M − H]− 596.1741 595.1668 595.1669 0.2 431, 287 * R, M, S
41 Narirutin C27H32O14 28.232 [M − H]− 580.1792 579.1719 579.1708 −1.9 271 M
42 Hesperetin 3′-O-glucuronide C22H22O12 29.202 [M−H]− 478.1111 477.1038 477.1022 −3.4 301, 175, 113, 85 * R, S
43 Hesperidin C28H34O15 30.888 [M − H]− 610.1898 609.1825 609.1803 −3.6 301 R
44 Naringenin 7-O-glucoside C21H22O10 31.079 [M − H]− 434.1213 433.1140 433.1136 −0.9 373, 343, 303 T
Flavonols
45 Kaempferol 3,7-O-diglucoside C27H30O16 24.228 [M − H]− 610.1534 609.1461 609.1464 0.5 447, 285 * R, M, S, T, By
46 Myricetin 3-O-rhamnoside C21H20O12 28.520 [M − H]− 464.0955 463.0882 463.0887 0.7 317 * Bl, R, S, T, By
47 Quercetin 3′-O-glucuronide C21H18O13 25.113 [M − H]− 478.0747 477.0674 477.0676 0.4 301 * R, S
48 Quercetin 3-O-(6″-malonyl-glucoside) C24H22O15 28.196 [M − H]− 550.0959 549.0886 549.0886 0.0 445, 300, 160 * T, Bl
49 Isorhamnetin 3-O-glucuronide C22H20O13 29.864 [M − H]− 492.0904 491.0831 491.0822 −1.8 315, 300, 272, 255 * R, S
50 Quercetin 3-O-arabinoside C20H18O11 30.940 [M − H]− 434.0849 433.0776 433.0756 −4.6 301 By
51 Isorhamnetin C16H12O7 36.775 [M − H]− 316.0583 315.0510 315.0498 −3.8 300, 271 * M, S
52 3,7-Dimethylquercetin C17H14O7 45.315 ** [M − H]− 330.0740 329.0667 329.0660 −1.1 314, 299, 271 * M, O, R, S, Bl
Dihydroflavonols
53 Dihydromyricetin 3-O-rhamnoside C21H22O12 15.838 [M − H]− 466.1111 465.1038 465.1024 −3.0 301 T
54 Dihydroquercetin C15H12O7 28.746 [M − H]− 304.0583 303.0510 303.0496 −4.6 285, 275, 151 * T, O
Dihydrochalcones
55 Phloretin 2′-O-xylosyl-glucoside C26H32O14 21.931 [M − H]− 568.1792 567.1719 567.1696 −4.1 437, 275, 169 * R, S
Anthocyanins
56 Cyanidin 3-O-(6″-p-coumaroyl-glucoside) C30H27O13 20.896 [M + H]+ 595.1452 596.1525 596.1527 0.3 287 * T, M, O
57 Quercetin 3-O-xylosyl-glucuronide C26H26O17 36.011 [M + H]+ 610.1170 611.1243 611.1247 0.7 679, 303, 285, 239 * T, O
Isoflavonoids
58 Dihydrobiochanin A C16H14O5 4.146 [M + H]+ 286.0841 287.0914 287.0914 0.0 269, 203, 175 O
59 3′,4′,5,7-Tetrahydroxyisoflavanone C15H12O6 34.208 [M − H]− 288.0634 287.0561 287.0564 1.0 269, 259 * T, O, Bl
60 5,6,7,3′,4′-Pentahydroxyisoflavone C15H10O7 40.677 [M − H]− 302.0427 301.0354 301.0346 −2.7 274, 200, 136 * T, O, S, By
61 3′,4′,7-Trihydroxyisoflavanone C15H12O5 45.000 [M − H]− 272.0685 271.0612 271.0609 −1.1 177, 151, 119, 107 * M, T, O
62 Sativanone C17H16O5 46.952 [M − H]− 300.0998 299.0925 299.0921 −1.3 284, 269, 225 S
63 3′-Hydroxydaidzein C15H10O5 47.113 [M − H]− 270.0528 269.0455 269.0451 −1.5 241, 224, 213, 181 * R, T, M, Bl, O, S
64 4′-Methoxy-2′,3,7-trihydroxyisoflavanone C16H14O6 47.278 [M − H]− 302.0790 301.0717 301.0704 −4.3 283, 177 R
65 3′-Hydroxymelanettin C16H12O6 54.909 [M − H]− 300.0634 299.0561 299.0559 −0.7 284 * T, M, O, R, S
Other polyphenols
Hydroxycoumarins
66 Esculin C15H16O9 15.852 [M − H]− 340.0794 339.0721 339.0690 −2.9 177 * S, R
67 Coumarin C9H6O2 17.634 [M + H]+ 146.0368 147.0441 147.0428 −4.8 103, 91 O
68 Esculetin C9H6O4 20.473 [M − H]− 178.0266 177.0193 177.0196 0.7 149, 133, 105, 89 * Bl, R, S, T
69 Umbelliferone C9H6O3 46.399 ** [M − H]− 162.0317 161.0244 161.0242 −1.2 133, 117, 105 * Bl, M, O, R, S
Hydroxybenzoketones
70 2-Hydroxy-4-methoxyacetophenone 5-sulfate C9H10O7S 12.281 [M − H]− 262.0147 261.0074 261.0076 0.8 181, 97 * R, T
Tyrosols
71 Oleoside 11-methylester C17H24O11 14.451 [M − H]− 404.1319 403.1246 403.1238 −2.0 223, 165 R, S
72 3,4-DHPEA-AC C10H12O4 85.689 [M − H]− 196.0736 195.0663 195.0656 −3.6 135 O
Phenolic terpenes
73 Rosmanol C20H26O5 53.370 [M − H]− 346.1780 345.1707 345.1693 −4.1 301 * R, S
74 Carnosol C20H26O4 79.943 [M − H]− 330.1831 329.1758 329.1742 −4.9 285 * R, T, S
75 Carnosic acid C20H28O4 85.366 [M − H]− 332.1988 331.1915 331.1907 −2.4 287 * R, S, Bl
Alkylphenols
76 3-Methylcatechol C7H8O2 14.350 [M − H]− 124.0524 123.0455 123.0455 1.8 281, 187, 165 * M, T
Other Polyphenols
77 Salvianolic acid B C36H30O16 32.130 [M − H]− 718.1534 717.1461 717.1442 −2.8 519, 339, 321, 295 * S, Bl
78 Lithospermic acid C27H22O12 35.122 [M−H]− 538.1111 537.1038 537.1013 −4.7 493, 339, 295 * T, O
Lignans
79 Enterolactone C18H18O4 4.786 [M + H]+ 298.1205 299.1278 299.1268 −3.3 281, 187, 165 O
80 Sesamin C20H18O6 18.227 [M − H]− 354.1103 353.1030 353.1021 −2.5 338, 163 P
81 7-Oxomatairesinol C20H20O7 18.661 [M + H]+ 372.1209 373.1282 373.1286 1.1 358, 343, 328, 325 D
82 Secoisolariciresinol C20H26O6 51.345 [M − H]− 362.1729 361.1656 361.1652 −1.1 165, 121 S
83 Deoxyschisandrin C24H32O6 84.114 [M − H]− 416.2199 415.2126 415.2107 −4.6 402, 347, 361, 301 S
Stilbenes
84 Piceatannol C14H12O4 8.718 [M − H]− 244.0736 243.0663 243.0662 −0.4 225, 201, 175, 159 * F, D

** = compound was identified in positive and negative mode [M + H]+/[M − H]− modes. * = proposed compound was identified in more than one sample. RT stands for “retention time”. Herbs were presented with abbreviations; Oregano (O), Rosemary (R), Basil (Bl), Bay (By), Parsley (P), Mint (M), Fenugreek (F), Dill (D), Sage (S) and Thyme (T).