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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.