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

Table 2.

Stilbenic compounds in the vegetative organs of the grapevine plant.

ID 1 Compound Group Compound Name 1,2 Chemical Formula 3 MW (g/mol) [M–H]– Precursor Ion Main MS/MS Fragments (m/z) 4 λmax (CH3OH) (nm) Detection Mode 5 Tissue Distribution 6
LEAVES STEMS CANES WOODS ROOTS
106 Monomers trans-Astringin C20H22O9 406.383 405 243, 225, 201, 322, 159, 199, 173 331, 305 MS ✓ ✓ ✓
107 Monomers trans-Resveratroloside C20H22O8 390.388 389 227, 185, 179, 269, 143, 305, 371, 209 311 MS ✓ ✓
108 Monomers trans-Resveratrol-2-C-glucoside NA NA 389 269, 241, 299, 175, 163 326 MS, NMR ✓ ✓
109 Monomers trans-Resveratrol-10-C-glucoside NA NA 435 389, 227 315 MS, NMR ✓
110 Monomers trans-Resveratrol-O-glucoside C20H22O8 390.388 389 227, 305, 175, 185 321 MS, NMR ✓ ✓ ✓
183 Monomers cis-Resveratrol-O-glucoside C20H23O8 391.391 389 227 319, 306 MS ✓
113 Monomers trans-Piceid C20H22O8 390.383 389 227, 185, 251, 269, 209, 371, 143 318, 306, 229 MS, NMR, DAD ✓ ✓ ✓ ✓ ✓
117 Monomers cis-Astringin C20H22O9 406.383 405 243, 225, 201, 322, 405, 159, 228, 157 324, 260 MS ✓
119 Monomers trans-Piceatannol C14H12O4 244.246 243 175, 225, 149, 215, 201, 159, 181, 132, 199, 143 325, 290, 306 MS, NMR ✓ ✓ ✓ ✓ ✓
120 Monomers cis-Resveratroloside C20H22O8 390.388 389 227, 371, 209 280 MS ✓
121 Monomers cis-Piceid C20H22O8 390.383 389 227, 269, 241, 185, 209, 371, 143 284, 230 MS, NMR ✓ ✓ ✓
122 Monomers trans-Isorhapontin C21H24O9 420.411 419 257, 241, 225, 175, 242, 201, 159, 281, 132 326, 303, 290 MS ✓
123 Monomers trans-Resveratrol C14H12O3 228.247 227 185, 143, 183, 159, 157, 212, 205 306, 319, 228 MS, NMR, DAD ✓ ✓ ✓ ✓ ✓
124 Monomers 2,4,6-Trihydroxyphenanthrene-2-O-glucoside C20H20O8 388.372 389 371, 353, 335, 227, 209, 199 261, 222 MS ✓
126 Monomers trans-Isorhapontigenin C15H14O4 258.270 257 242, 241, 224, 172, 213, 185 325, 303, 290 MS ✓ ✓ ✓
127 Monomers trans-Pinostilbene-4′-O-glucoside C21H24O8 404.410 403 241, 226, 225 NA MS ✓
128 Monomers cis-Resveratrol C14H12O3 228.247 227 185, 159, 143, 157, 212, 143 285, 232 MS, NMR ✓ ✓
145 Monomers trans-Pterostilbene C16H16O3 256.296 255 239, 197, 209, 226, 165 298, 305, 275 MS, NMR, DAD ✓ ✓
146 Monomers cis-Pterostilbene C16H16O3 256.296 255 197, 239, 209, 226, 165 279 MS ✓
153 Monomers cis-Isorhapontigenin C15H14O4 258.270 257 241, 213, 185, 224 318, 220 MS ✓
154 Monomers trans-Rhaponticin C21H24O9 420.414 419 257, 241, 281, 299, 323, 405, 389, 243, 169, 395 324, 220 MS ✓
155 Monomers trans-Pinostilbene C15H14O3 242.270 241 181, 225, 197, 169 NA MS ✓
156 Monomers cis-Pinostilbene C15H14O3 242.270 241 181, 225, 197, 169 NA MS ✓
111 Dimers Leachianol G C28H24O7 472.496 471 387, 377, 349, 255, 121 280, 218 MS, NMR ✓ ✓ ✓
112 Dimers Leachianol F C28H24O7 472.496 471 349, 453, 255, 287, 153, 241, 121 280, 218 MS, NMR ✓ ✓ ✓
114 Dimers Restrytisol A C28H24O7 472.486 471 377, 255, 349, 121, 471 280, 221 MS ✓ ✓ ✓
115 Dimers Ampelopsin A C28H22O7 470.479 469 345, 451, 375, 363, 257, 357, 423, 317, 241 283 MS, NMR ✓ ✓ ✓ ✓
116 Dimers Pallidol C28H22O6 454.478 453 359, 265, 435, 406, 391, 346, 273 284 MS, NMR ✓ ✓ ✓ ✓ ✓
118 Dimers Caraphenol B C28H22O7 470.473 469 451, 281, 363, 375, 227, 423 326, 291 MS ✓ ✓
130 Dimers Ampelopsin D C28H22O6 454.478 453 359, 361, 437, 215, 343, 199, 255, 289 314, 280 MS, NMR ✓ ✓ ✓ ✓
131 Dimers Quadrangularin A C28H22O6 454.471 453 359, 289, 411, 435, 347, 253 314 MS, NMR ✓ ✓
132 Dimers (+)-cis-ε-Viniferin C28H22O6 454.471 453 435, 347, 411, 333, 359, 369, 253 286, 201, 230 MS, NMR ✓ ✓
134 Dimers (+)-trans-ε-Viniferin C28H22O6 454.471 453 359, 435, 347, 369, 411, 333, 253, 225 327, 285, 308 MS, NMR, DAD ✓ ✓ ✓ ✓ ✓
135 Dimers Viniferifuran C28H20O6 452.455 451 NA 317, 289, 209 MS, NMR ✓
136 Dimers Diptoindonesin A C34H32O11 616.610 615 453, 359, 411, 347, 585 326, 226 MS, NMR ✓ ✓
141 Dimers trans-ω-Viniferin C28H22O6 454.478 453 435, 359, 347, 411, 395, 333, 285 324, 280 MS, NMR ✓ ✓ ✓ ✓
144 Dimers cis-ω-Viniferin C28H22O6 454.478 453 435, 411, 395, 333, 285, 359, 225 294 MS. NMR ✓
149 Dimers trans-δ-Viniferin C28H22O6 454.478 453 435, 369, 411, 347, 333, 359, 225, 409 312, 225 MS, DAD ✓ ✓ ✓ ✓
152 Dimers cis-δ-Viniferin C28H22O6 454.478 453 435, 411, 369, 359, 333, 347, 317, 307, 251, 267 285, 232 MS ✓
157 Dimers trans-ε-Viniferin derivative (dimethylated) C30H26O6 482.523 481 387, 375, 226, 197, 466 325 MS ✓
158 Dimers trans-δ-Viniferin derivative (dimethylated) C30H26O6 482.523 481 397, 361, 439, 387, 463 313 MS ✓
159 Dimers trans-Scirpusin A C28H22O7 470.470 469 375, 451, 385, 359, 241, 427, 728, 445, 287, 514, 955 320, 286, 204 MS, NMR ✓
162 Dimers Maackin A C28H22O8 486.470 485 244, 226, 137 327, 288, 204 MS, NMR ✓
164 Dimers trans-ε-Viniferin derivative (γ-lactam ring) C32H26O7N 936.550 536 NA NA MS, NMR ✓
165 Dimers trans-Resveratrol derivative (γ-lactam ring) C18H16O4N 310.324 310 NA NA MS, NMR ✓
171 Dimers Malibatol A C28H20O7 468.454 467 NA NA MS, NMR ✓
172 Dimers Ampelopsin F C28H22O6 454.471 453 NA 282, 220 MS, NMR ✓
176 Dimers Viniferal C35H26O8 574.579 573 NA NA MS, NMR ✓
177 Dimers Vitisinol C C27H24O5 428.482 427 NA 358, 279 MS ✓
178 Dimers Vitisinol E C27H24O6 444.475 444 NA 281, 230, 204 MS, NMR ✓
179 Dimers Vitisinol B C35H26O8 574.579 573 NA 282, 228, 204 MS, NMR ✓
181 Dimers Viniferether A C29H26O7 486.509 485 NA 280, 229 MS, NMR ✓
182 Dimers Viniferether B C29H26O7 486.513 485 NA 280, 231 MS, NMR ✓
125 Trimers Ampelopsin B C28H22O6 454.478 453 359, 243, 211, 183, 265 281, 328 MS, NMR ✓ ✓ ✓
139 Trimers trans-Miyabenol C C42H32O9 680.698 679 661, 573, 479, 451, 637, 585, 447 322, 279 MS, NMR ✓ ✓ ✓ ✓ ✓
140 Trimers cis-Miyabenol C C42H32O9 680.699 679 661, 573, 479, 451, 637, 585, 447 285 MS, NMR ✓ ✓
142 Trimers Davidiol A C42H32O9 680.704 679 585, 447, 491, 385, 479, 465, 567 284, 219 MS ✓ ✓
143 Trimers α-Viniferin C42H30O9 678.682 677 571, 583, 437, 449, 463, 501, 331 284, 309 MS, NMR ✓ ✓ ✓
161 Trimers Ampelopsin C C42H32O9 680.709 679 NA 283 MS, NMR ✓ ✓
169 Trimers Viniferol D C42H32O9 680.702 679 NA NA MS, NMR ✓ ✓
173 Trimers Ampelopsin E C42H32O9 680.701 679 NA 325, 285 MS, NMR ✓ ✓
129 Tetramers Hopeaphenol C56H42O12 906.925 905 811, 717, 451, 611, 359, 299 283, 226 MS, NMR ✓ ✓ ✓ ✓
133 Tetramers Isohopeaphenol C56H42O12 906.925 905 451, 675, 811, 717, 358, 265 284 MS, NMR ✓ ✓ ✓ ✓ ✓
137 Tetramers Ampelopsin H C56H42O12 906.925 905 811, 717, 705, 793 281 MS, NMR ✓ ✓ ✓
138 Tetramers Vaticanol C-like isomer C56H42O12 906.929 905 811, 717, 793, 705, 611 281 MS, NMR ✓
147 Tetramers Vitisin A (r2-viniferin) C56H42O12 906.920 905 811, 887, 717, 693, 545, 451, 359, 265 328, 285 MS, NMR ✓ ✓ ✓ ✓
148 Tetramers Vitisifuran A C56H40O12 904.907 903 NA 322, 232 MS, NMR ✓
150 Tetramers Vitisin B (r-viniferin) C56H42O12 906.920 905 799, 887, 811, 717, 545, 451, 359, 317 321, 286 MS, NMR ✓ ✓ ✓ ✓
151 Tetramers Vitisifuran B C56H40O12 904.907 903 NA 324, 228 MS, NMR ✓
160 Tetramers Vitisin C C56H42O12 906.926 905 NA NA MS, NMR ✓
166 Tetramers Viniferol A C56H42O12 906.925 905 559, 813, 361, 453, 651, 541, 801, 783 284, 227 MS, NMR ✓
167 Tetramers Viniferol B C56H42O12 906.929 905 559, 813, 361, 453, 651, 541, 801, 783 283, 225 MS, NMR ✓
168 Tetramers Viniferol C C56H42O12 906.929 905 NA 284, 228 MS, NMR ✓
170 Tetramers Viniferol E C56H44O13 924.940 923 NA 284, 231 MS, NMR ✓
174 Tetramers Wilsonol C C56H42O12 906.929 905 NA 231 NMR ✓
175 Tetramers Heyneanol A C56H42O12 906.929 905 320, 284 322, 237 NMR ✓
180 Tetramers Stenophyllol C C56H42O12 906.923 905 NA 285, 330, 223 MS, NMR ✓
163 Hexamers Viniphenol A C84H64O18 1361.391 1360 NA NA MS, NMR ✓

1 Other reported names are found in Table S2, where compounds are numbered (ID) according to their elution patterns. 2 Another stilbene is reported in the literature as vitisinol E (compound 178), but with the formula C29H26O7, MW of 486,51, [M − H] − (m/z) of 485, λmax CH3OH of 358, 279, 253. 3 NA = not available or not applicable, MW = Molecular Weight. 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.