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. 2020 May 8;9(5):398. doi: 10.3390/antiox9050398

Table 1.

Polyphenols (excluding stilbenes) in the vegetative organs of the grapevine plant.

ID 1 Compound Group Compound
Name 1 		Chemical Formula 2 MW (g/mol) [M–H]– Main MS/MS Fragments (m/z) 3,4 λmax (CH3OH) (nm) Detection Mode 5 Tissue Distribution 6
LEAVES STEMS CANES WOODS ROOTS
1 Hydroxybenzoic acid Quinic acid C7H12O6 192.167 191 111, 173, 85, 127 308, 280 MS ✓
2 Hydroxybenzoic acid Gallic acid C7H6O5 170.120 169 125, 124, 79, 51 278, 214 MS, NMR, DAD ✓ ✓ ✓
4 Hydroxybenzoic acid Protocatechuic acid C7H6O4 154.121 153 109, 108 297, 258 MS ✓ ✓
7 Hydroxybenzoic acid p-Hydroxybenzoic acid C7H6O3 138.122 137 93, 60, 79, 108, 118, 137 272, 310sh MS ✓ ✓
8 Hydroxybenzoic acid Gentisic acid C7H6O4 154.121 153 109, 81, 42, 108 281, 228, 330sh MS ✓
9 Hydroxybenzoic acid γ-Resorcylic acid C7H6O4 154.121 153 109, 136, 154, 110, 52, 80, 137, 39, 155 313, 245 MS ✓
30 Hydroxybenzoic acid Vanillic acid C8H8O4 168.149 167 123, 152, 108, 91 292, 260 MS, NMR, DAD ✓ ✓
36 Hydroxybenzoic acid Syringic acid C9H10O5 198.174 197 182, 153, 167, 138 276 MS, NMR, DAD ✓ ✓ ✓
50 Hydroxybenzoic acid Ellagic acid C14H6O8 302.194 301 284, 300, 257, 229, 184 367, 256, 301sh MS ✓ ✓
14 Hydroxycinnamic acid 1-O-Sinapoyl-β-D-glucose C17H22O10 386.353 385 223, 205, 341, 265, 190, 179, 119, 247 282 MS ✓
16 Hydroxycinnamic acid 1-O-(4-Coumaroyl)-glucose C15H18O8 326.301 325 163, 145, 119, 187, 265, 205 322 MS ✓ ✓
20 Hydroxycinnamic acid 1-Caffeoyl-β-D-glucose C15H18O9 342.300 341 179, 161, 143, 149, 131, 135 290, 304sh, 328 MS ✓ ✓
21 Hydroxycinnamic acid Ferulic acid pentose NA NA 325 149, 178, 193 326, 275 MS ✓ ✓
22 Hydroxycinnamic acid Caftaric acid isomer C13H11O9 311.224 311 179, 135, 149 325, 286 MS ✓
24 Hydroxycinnamic acid Caftaric acid C13H12O9 312.230 311 179, 135, 149, 267, 161, 237 326, 298sh, 243 MS, NMR, DAD ✓ ✓ ✓
27 Hydroxycinnamic acid Coutaric acid C13H12O8 296.231 295 163, 149, 119 316, 234, 300sh MS, DAD ✓ ✓
28 Hydroxycinnamic acid Chlorogenic acid C16H18O9 354.311 353 191, 179, 135, 161, 335, 172, 284 328, 244, 303sh MS, DAD ✓
31 Hydroxycinnamic acid Chicoric acid C22H18O12 474.374 473 311, 293, 179, 149, 135, 219 328, 305sh, 279 MS ✓
32 Hydroxycinnamic acid Fertaric acid C14H14O9 326.259 325 193, 175, 149, 281, 134 314, 279 MS ✓
35 Hydroxycinnamic acid Caffeic acid C9H8O4 180.159 179 135, 134, 96 324, 299sh, 240 MS, NMR, DAD ✓ ✓ ✓
43 Hydroxycinnamic acid p-Coumaric acid C9H8O3 164.160 163 119, 104, 93 310, 225, 211, 310sh MS, NMR, DAD ✓ ✓ ✓
46 Hydroxycinnamic acid Ferulic acid C10H10O4 194.186 193 134, 149, 178, 116 323, 289, 238sh MS, NMR, DAD ✓ ✓ ✓
48 Hydroxycinnamic acid Sinapic acid C11H12O5 224.212 223 164, 149, 208, 164, 193, 179 318, 238 MS ✓ ✓
83 Hydroxycinnamic acid Cinnamic acid C9H8O2 148.161 147 103, 77, 87, 129 276, 215, 203 DAD ✓
3 Flavan-3-ol Gallocatechin C15H14O7 306.270 305 179, 221, 219, 165, 261, 125, 137 274, 370 MS ✓
6 Flavan-3-ol Procyanidin B1 C30H26O12 578.526 577 425, 407, 289, 451, 287, 245, 451 275, 322 MS, NMR, DAD ✓ ✓ ✓
10 Flavan-3-ol Procyanidin A1 C30H24O12 576.501 575 449, 289, 423, 539, 477, 407, 441 280 MS ✓ ✓ ✓
15 Flavan-3-ol Epigallocatechin C15H14O7 306.270 305 179, 165, 219, 221, 261, 125, 261, 125 274, 212, 235 MS ✓
18 Flavan-3-ol Procyanidin C1 C45H38O18 866.778 865 695, 407, 577, 287, 713, 739, 575, 425, 289 279 MS, DAD ✓ ✓
19 Flavan-3-ol Procyanidin T2 C45H38O18 866.778 865 577, 713, 289, 287, 425, 575, 695, 407, 739 280 MS, DAD ✓ ✓
23 Flavan-3-ol Catechin C15H14O6 290.271 289 245, 203, 179, 205, 227, 109, 123, 165, 125, 151 275, 222 MS, NMR, DAD ✓ ✓ ✓
25 Flavan-3-ol Procyanidin B3 C30H26O12 578.526 577 425, 407, 289, 151, 559, 445 270, 330 MS, NMR, DAD ✓ ✓
26 Flavan-3-ol Procyanidin B4 C30H26O12 578.526 577 425, 407, 289 280, 240 MS, DAD ✓ ✓
29 Flavan-3-ol Procyanidin B2 C30H26O12 578.526 577 425, 407, 289, 451, 287, 245, 125 280, 240, 370 MS, NMR, DAD ✓ ✓ ✓
37 Flavan-3-ol Epigallocatechin gallate C22H18O11 458.375 457 305, 219, 261, 221, 359, 169, 305, 289, 271, 125, 331 274, 238 MS, DAD ✓
38 Flavan-3-ol Prodelphinidin A-type C30H26O13 594.527 593 425, 441, 573, 423, 407, 289, 531, 273, 339, 245, 177, 161 276, 228, 320 MS ✓ ✓
39 Flavan-3-ol Procyanidin dimer gallate NA NA 729 577, 407, 559, 451, 711, 289, 593, 437, 425 280 MS, DAD ✓ ✓
40 Flavan-3-ol Epicatechin C15H14O6 290.271 289 245, 203, 109, 179, 205, 123, 125, 151 277, 226 MS, NMR, DAD ✓ ✓ ✓
42 Flavan-3-ol Gallocatechin gallate C22H18O11 458.375 457 169, 161, 359, 331, 169, 305, 193 276, 240 MS ✓
47 Flavan-3-ol Epicatechin gallate C22H18O10 442.376 441 289, 245, 205, 169, 125, 331, 271, 179 278, 240 MS, NMR, DAD ✓ ✓
61 Flavan-3-ol Catechin gallate C22H18O10 442.376 441 289, 245, 205, 331, 169, 125, 425, 271, 395, 169, 193, 405 278 MS ✓ ✓
33 Anthocyanin Delphinidin-3-O-glucoside C21H21O12+ 465.387 463 301, 300, 271, 125 526, 361, 277, 402sh DAD ✓
34 Anthocyanin Cyanidin-3-O-glucoside C21H21O11+ 449.388 447 284, 211, 285, 255, 147, 227 516, 262, 301sh MS, DAD ✓
44 Anthocyanin Petunidin-3-O-glucoside C22H23O12+ 479.414 477 314, 315, 299, 300 526, 344sh, 277 DAD ✓
45 Anthocyanin Peonidin-3-O-glucoside C22H23O11+ 463.415 461 299, 298, 284, 255, 227, 211 517, 280, 330sh, 421sh MS, DAD ✓
52 Anthocyanin Malvidin-3-O-glucoside C23H25O12+ 493.441 491 329, 314, 299 528, 348sh, 288 MS, DAD ✓ ✓
59 Anthocyanin Petunidin-3-(6-O-acetyl)glucoside C24H25O13+ 521.451 519 315, 302, 274, 149 528, 270, 350sh DAD ✓
62 Anthocyanin Peonidin-3-(6-O-acetyl)glucoside C24H25O12+ 505.452 504 301 , 286, 230, 258, 268 522, 280 DAD ✓
67 Anthocyanin Malvidin-3-(6-O-acetyl)glucoside C25H27O13+ 535.478 533 329, 315 522, 344, 278 DAD ✓
72 Anthocyanin Cyanidin-3-(6-O-coumaroyl)glucoside C30H27O13+ 595.533 593 287 , 259, 231, 213, 259 524, 314, 284, 449sh DAD ✓
80 Anthocyanin Petunidin-3-(6-O-coumaroyl)glucoside C31H29O14+ 625.553 624 317 , 302, 274, 218, 228, 246 534, 282, 313 DAD ✓
81 Anthocyanin Peonidin-3-(6-O-coumaroyl)glucoside C31H29O13+ 609.554 608 301 , 286, 230, 258, 268 522, 312 MS, DAD ✓
85 Anthocyanin Malvidin-3-(6-O-coumaroyl)glucoside C32H31O14+ 639.586 637 329, 299, 281 534, 318 DAD ✓
86 Anthocyanin Malvidin-3-(6-O-caffeoyl)glucoside C32H31O15+ 655.581 655 331, 299, 637, 315, 475 532, 324, 284 MS ✓
87 Anthocyanin Malvidin-3-O-rutinoside C29H35O16+ 639.583 637 331 526, 288 MS ✓
41 Flavanone Taxifolin C15H12O7 304.254 303 285, 125, 177, 275, 151, 259, 217 290, 326sh MS ✓
55 Flavanone Taxifolin-O-pentoside C20H20O11 436.371 435 303, 285, 399, 151, 241, 217, 175 274, 317 MS ✓
56 Flavanone Taxifolin-3-O-glucoside C21H22O12 466.395 465 285, 303, 151, 339, 177, 259, 447 290 MS ✓
57 Flavanone Taxifolin-3-O-rhamnoside C21H22O11 450.396 449 303, 285, 151, 323, 431 292, 235 MS ✓
88 Flavanone Hesperetin C16H14O6 302.282 301 258, 143, 157, 137, 286 284, 324sh, 221 MS ✓
95 Flavanone Eriodictyol-7-O-glucoside C21H22O11 450.396 449 287, 269, 151, 135, 259, 225, 209, 431 281, 327 MS ✓
103 Flavanone Naringenin C15H12O5 272.256 271 151, 177, 119, 165, 125, 107, 227, 191 289, 228, 336sh MS ✓
104 Flavanone Naringenin-7-O-glucoside C21H22O10 434.397 433 271, 269, 313, 177, 151, 119, 107 282, 222 MS ✓
49 Flavonol Myricetin-3-O-galactoside C21H20O13 480.378 479 317, 316, 178, 271 360, 265 MS, DAD ✓
51 Flavonol Myricetin-3-O-glucuronide C21H18O14 494.361 493 317 353, 300sh, 261 MS, DAD ✓
53 Flavonol Myricetin-3-O-glucoside C21H20O13 480.378 479 317, 316, 169, 271, 303, 227, 179, 151 362, 298sh, 260 MS, DAD ✓
54 Flavonol Quercetin-3-O-rutinoside C27H30O16 610.521 609 301, 300, 271, 255, 179, 343, 151 353, 256, 294sh MS, NMR, DAD ✓ ✓
58 Flavonol Quercetin-3-O-galactoside C21H20O12 464.379 463 301, 300, 179, 273, 257, 151 362, 256, 301sh MS, NMR, DAD ✓ ✓ ✓
60 Flavonol Quercetin-3-O-glucoside C21H20O12 464.379 463 301, 300, 271, 161, 179, 255, 151 358, 256, 300sh MS, NMR, DAD ✓ ✓
63 Flavonol Quercetin-3-O-glucuronide C21H18O13 478.362 477 301, 179, 151, 283, 459, 431, 501 356, 254, 300sh MS, NMR, DAD ✓ ✓
65 Flavonol Myricetin-3-O-rhamnoside C21H20O12 464.379 463 317, 316, 271, 300, 179, 287, 151 372, 302sh, 248 MS ✓
68 Flavonol Myricetin C15H10O8 318.237 317 151, 179, 137, 287, 271, 109, 192 372, 253, 303sh, 207 MS, NMR, DAD ✓
69 Flavonol Quercetin-3-O-rhamnoside C21H20O11 448.380 447 301, 300, 179, 151, 271, 257 354, 258, 307sh MS, NMR, DAD ✓ ✓
70 Flavonol Kaempferol-3-O-galactoside C21H20O11 448.380 447 285, 255, 227, 327 361, 260 MS ✓
71 Flavonol Kaempferol-3-O-rutinoside C27H30O15 594.522 593 285, 257, 151, 447, 199, 241, 93 354, 274 MS, DAD ✓ ✓
73 Flavonol Kaempferol-3-O-glucuronide C21H18O12 462.363 461 285, 267, 443, 417, 257, 229 348, 265 MS, DAD ✓
74 Flavonol Quercetin-3-(6-O-acetyl)glucoside C23H22O13 506.416 505 301, 300, 463, 271, 255 354, 256, 267sh, 298sh MS ✓
75 Flavonol Quercetin-3-(3-O-arabinosyl)glucoside C26H28O16 596.493 595 301, 517, 151, 300, 463, 179, 445, 271, 255 354, 260, 231 MS ✓
76 Flavonol Quercetin-3-(7-O-glucosyl)glucuronide C27H28O18 640.503 639 477, 301, 179, 151 361, 300, 268, 256 DAD ✓
77 Flavonol Quercetin-3-O-arabinose C20H18O11 434.350 433 301, 179, 151, 300, 283 358, 311 MS ✓ ✓
78 Flavonol C33H40O21 772.662 771 609, 301 355, 259, 299sh, 204 NMR, DAD ✓
79 Flavonol Kaempferol-3-O-glucoside C21H20O11 448.380 447 285, 255, 151, 227, 327, 243 348, 263, 297sh MS, DAD ✓ ✓
82 Flavonol Quercetin C15H10O7 302.239 301 151, 179, 273, 193, 257, 229 372, 255, 202sh, 300sh MS, NMR, DAD ✓ ✓
84 Flavonol Kaempferol C15H10O6 286.239 285 187, 117, 211, 127, 257, 151, 169, 241 369, 258, 390 MS, NMR, DAD ✓ ✓
89 Flavonol Kaempferol-3-O-xyloside C20H18O10 418.354 417 285, 255, 227 350 MS ✓
90 Flavonol Kaempferol-3-O-rhamnoside C21H20O10 432.381 431 285 351, 264, 202, 294sh MS ✓
91 Flavonol Dihydrokaempferol-3-O-rhamnoside C21H22O10 434.397 433 269, 287, 259, 180, 151, 368 286, 230 MS ✓
92 Flavonol Isorhamnetin-3-O-galactoside C22H22O12 478.406 477 315,.314 271, 300, 357 366, 289, 259 MS ✓
93 Flavonol Isorhamnetin-3-O-glucoside C22H22O12 478.406 477 315, 314, 285, 357, 271 354, 265sh MS, DAD ✓
94 Flavonol Quercetin-3-(6-O-rhamnosyl)galactoside C27H30O16 610.517 609 301, 541, 463, 300, 271, 255, 179, 447, 151 356, 256, 300 NMR, DAD ✓
96 Flavonol Isorhamnetin-3-O-arabinose C21H20O11 448.381 447 315, 314, 271, 243 345, 258 MS ✓
97 Flavonol Isorhamnetin-3-O-glucuronide C22H20O13 492.389 491 315, 255, 151 355, 265sh MS ✓
98 Flavonol Isorhamnetin-3-O-rutinoside C28H32O16 624.548 623 315, 300, 468 354, 256 MS ✓
99 Flavonol Isorhamnetin-3-(6-O-feruloyl)glucoside C32H30O15 654.577 653 315 320, 274 MS ✓
100 Flavonol Isorhamnetin-3-(4-O-rhamnosyl)rutinoside C34H42O20 770.685 769 461, 623, 163 354, 256 MS, DAD ✓
101 Flavonol Kaempferol-3-(6-O-coumaroyl)glucoside C30H26O13 594.525 593 285, 227, 255 317, 265, 356sh, 310sh MS ✓
102 Flavonol Kaempferol-3 (7-O-glucosyl)galactoside C27H30O16 610.521 609 447, 489, 285 343, 300sh, 265 DAD ✓
105 Flavonol Diquercetin-3-(3-O-glucosyl)glucuronide C42H36O24 924.722 923 765, 755, 837, 903, 935, 808 374 MS ✓
64 Flavone Apigenin-7-O-glucoside C21H20O10 432.381 431 269, 283, 311, 413, 231, 225, 201, 197, 149 335, 269, 253 MS, NMR, DAD ✓
66 Flavone Luteolin-7-O-glucoside C21H20O11 448.380 447 285, 226, 257, 217, 241, 198 349, 254sh, 205 MS, NMR, DAD ✓
5 Coumarin Aesculin C15H16O9 340.282 339 133, 177, 150 346, 289 MS ✓
11 Dihydrochalcone Phlorizin C21H24O10 436.413 435 273, 167, 229, 297 285, 230sh MS ✓
12 Coumarin Fraxin C16H18O10 370.310 369 207, 192, 354, 149, 123 332, 308sh MS ✓
13 Coumarin Aesculetin C9H6O4 178.143 177 149, 133, 105, 91, 115, 89, 65 334, 288sh MS ✓
17 Coumarin Umbelliferone C9H6O3 162.144 161 133, 117, 105, 51, 78 323, 236 MS ✓

1 Other reported names are found in Table S1, where compounds are numbered (ID) according to their elution patterns. 2 NA = not available or not applicable, MW = Molecular Weight. 3 MS-MS values in italic (compounds 62, 72, 80, 81) are reported in positive mode. 4 The most abundant fragments are highlighted in bold. 5 MS = mass spectrometry detection, NMR = nuclear magnetic resonance detection, DAD = diode array or ultraviolet detection. 6 In blue with √ are detected compounds; in light red are undetected compounds or unavailable information.