Table 1.
Characterization of polyphenolic compounds in male flowers of date palm using LCESI-MS/MS in negative ion mode.
| Comp. | Rt | Tentative Identification | MW | [M − H]− | Major Fragments (m/z) |
|---|---|---|---|---|---|
| Hydroxycinnamates | |||||
| 1 | 1.12 | Caffeoyl-O-hexoside | 342 | 341 | 179 (100), 161, 153, 143 |
| 2 | 16.93 | 5-O-caffeoylshikimic acid (5-CSA) | 336 | 335 | 317, 299, 291, 219, 273, 255, 179 (100), 161, 155, 137, 135, 93 |
| 3 | 17.34 | 4-O-caffeoylshikimic acid (4-CSA) | 336 | 335 | 317, 291, 219, 273, 255, 179 (100), 161 (100), 155, 137, 135, 95 |
| 4 | 18.27 | 3-O-caffeoylshikimic acid (3-CSA) | 336 | 335 | 317, 299, 291, 219, 273, 255, 179 (100), 161, 155, 137, 135, 93 |
| 5 | 21.13 | 5-O-p-coumaroylshikimic acid (5-p-CoSA) | 320 | 319 | 301, 275, 257, 243, 231, 217, 203, 171, 163 (100), 155, 145, 137, 119, 93 |
| 6 | 22.92 | 4-O-p-coumaroylshikimic acid (3-p-CoSA) | 320 | 319 | 275, 257, 199, 163 (100), 155, 145, 137, 119, 93 |
| 7 | 25.50 | caffeoyl-2-hydroxyethane-1,1,2-tricarboxylic acid | 340 | 339 | 295, 251, 179 (100) |
| 8 | 26.71 | Ferulic acid | 194 | 193 | 178, 161, 134 |
| 9 | 30.12 | caffeoylquinate shikmate derivative | 510 | 509 | 491 (100), 473, 455, 389, 371, 347, 329, 161 |
| 10 | 31.00 | 3,7-O-diferuloyl-4-O-caffeoyl quinic acid | 706 | 705 | 687, 663, 645, 559, 541, 529 (100), 527, 511, 483, 405, 337, 265, 259 |
| 11 | 32.22 | Feruloyl-O-p-coumaroyl-O-caffeoylshikimic acid | 676 | 675 | 643, 627, 603, 588, 513 (100), 495, 493, 463, 431, 375, 339, 313, 295 (100) |
| 12 | 32.64 | 5-O-p-coumaroyl-4-O-caffeoyl-4-methylpentanoic acid-5-hydroxy-3-quinate | 694 | 693 | 663, 499, 353, 345, 337, 221 |
| 13 | 32.80 | 1-O-caffeoyl-3-O-sinapoylquinic acid | 560 | 559 | 381 |
| 14 | 34.79 | Feruloyl-O-sinapoyl-O-caffeoylquinic acid | 736 | 735 | 693, 675, 559, 541, 527, 517, 513, 481, 479, 455, 323, 305 |
| 15 | 35.46 | 3-O-feruloyl-7-O-acyl-feruloyl-4-O-caffeoyl-quinic acid | 748 | 747 | 729, 705, 687, 591, 583, 574, 571 (100), 573, 559, 547, 529, 409, 381, 357, 333, 277 |
| 16 | 37.50 | (E)-3-(3,4-diacetoxy-5-methoxyphenyl)acroyl-4-O-p-coumaroyl-5-O-caffeoylquinic acid | 778 | 777 | 759, 735, 717, 693, 675, 615, 601, 559, 541, 527, 517, 513, 499, 481, 479, 455, 439, 425, 337,323, 305, 279, 271, 247, 245, 217 |
| 17 | 37.61 | Tri-caffeoylquinic acid | 712 | 711 | 679, 667, 635, 535, 387, 355, 353 |
| 18 | 40.95 | 3-O-p-coumaroyl-4-O-hydrosinapoyl-O-hexoside-5-O-caffeoylquinic acid | 870 | 869 | 707, 693 (100), 675, 661, 499, 413, 355, 337, 323, 265, 247 |
| 19 | 67.66 | p-coumaroyl-O-16-hydroxypalmatic acid | 419 | 418 | 163, 145, 119, 93 |
| Other organic acids | |||||
| 20 | 15.81 | Ascorbic acid | 176 | 175 | 157 |
| 21 | 25.51 | Trihydroxy-octadecanoic acid isomer | 330 | 329 | 314 (100), 135 |
| 22 | 29.05 | Trihydroxy-octadecadienoic acid isomer | 328 | 327 | 206 |
| 23 | 30.39 | Pentahydroxy-octadecanoic acid isomer | 348 | 347 | 329, 311, 304, 193, 161 |
| 24 | 32.42 | Trihydroxyoctadecanoic acid sulphate | 334 | 333 | 315 (100), 235, 151, 97 |
| Flavan-3-ols | |||||
| 25 | 11.63 | (E)Catechin a | 290 | 289 | 271, 247, 245 (100), 231, 221, 205, 179, 167, 151, 139, 125, 109 |
| 26 | 12.20 | (E)Catechin–(E)Catechin–(E)Catechin a | 866 | 865 | 847, 739, 713, 647, 627, 617, 577, 575 (100), 559, 515, 449, 477, 404, 327, 287 |
| 27 | 21.42 | (E)Catechin–(E)Catechin–(E)Catechin a | 866 | 865 | 847, 739, 713, 647, 627, 617, 577, 575 (100), 559, 515, 449, 477, 404, 327, 287 |
| 28 | 27.56 | (E)Catechin–(E)Gallocatechin a | 594 | 593 | 575, 557, 549, 513, 487, 473, 449, 441, 407, 343, 305 (100), 289, 187 |
| Flavan-3-ols | |||||
| 29 | 27.61 | (E)Catechin–(E)Catechin a | 578 | 577 | 435, 425, 407, 289 (100), 287 |
| 30 | 30.54 | (E)Catechin–(E)Catechin–(E)Catechin–(E)Catechina | 1154 | 1153 | 1065, 1043, 1027 (100), 983, 947, 865 (100), 711, 701, 693, 651, 605, 575, 549, 425, 407, 289 |
| Anthocyanidins | |||||
| 31 | 25.19 | Cyanidin | 287 | 286 | 271, 225, 151 (100), 135, 125, 107 |
| 32 | 30.27 | Pelargonidin dimethyl derivative | 301 | 300 | 271 (100), 243, 163 |
| Flavonols and flavones | |||||
| 33 | 21.23 | Dihexosylisorhamentin | 640 | 639 | 611, 477, 315 (100), 300, 280, 270, 255, 242, 214, 205 |
| 34 | 21.53 | Hexosylquercetin | 464 | 463 | 343, 301(100), 217 |
| 35 | 21.83 | Dihexosylquercetin | 626 | 625 | 463, 314, 301 (100) |
| 36 | 23.54 | Gliricidin or 3-O-methylorobol | 300 | 299 | 284 (100), 272, 271, 255, 254 |
| 37 | 24.21 | Rhamnosylhexosyl luteolin | 594 | 593 | 575, 447 (100), 429, 327, 285 (100), 257, 241, 215, 195, 177 |
| 38 | 24.47 | Isorhamentin b | 315 | 314 | 299 (100), 286, 285, 271, 255, 243, 230 |
| 39 | 24.67 | Rhamnosylhexosyl methyl quercetin | 624 | 623 | 608, 591, 519, 477, 459, 339, 315 (100), 299 |
| 40 | 25.14 | Dihydrokaempferol | 288 | 287 | 272, 225, 160, 151, 139, 125, 107 |
| 41 | 25.88 | Isorhamentin hexoside | 478 | 477 | 409, 357, 329, 315 (100), 300, 271, 243, 173 |
| 42 | 26.65 | Kaempferol | 286 | 285 | 257, 241, 217,213, 197 |
| 43 | 26.76 | Isorhamentin b | 315 | 314 | 299, 286 (100), 285, 271 |
| 44 | 26.85 | Orientin or Isoorientin | 448 | 447 | 299 (100), 284 |
| 45 | 28.22 | (Orientin or Isoorientin)-sulphate | 528 | 527 | 447, 299 |
| 46 | 28.90 | Quercetin rutinoside | 610 | 609 | 591, 465, 463, 373, 343, 301 (100), 287, 271, 255, 226, 179 |
| 47 | 29.73 | Gliricidin or 3-O-methylorobol | 300 | 299 | 284 (100), 272, 271, 255, 254, 202 |
| 48 | 29.99 | quercetin acetyl-hexoside | 506 | 505 | 463, 301 (100), 300 |
| 49 | 31.54 | Hexosyl-acyl-isorhamnetin | 520 | 519 | 459, 451, 357, 315 (100), 314, 299, 285, 243, 204, 187, 151 |
| 50 | 31.64 | Chrysoeriol hexoside | 462 | 461 | 446, 299 |
| 51 | 34.08 | Rhamnosyl-hexosyl-acyl-quercetin | 650 | 649 | 607, 589, 503, 485, 407, 341, 299 (100), 284 |
| 52 | 34.90 | Rhamnosylhexosyl-methyl-quercetin | 612 | 611 | 594, 521, 491, 449, 327, 286 |
| 53 | 35.84 | Quercetin | 302 | 301 | 273, 257, 229, 215 (100), 211, 193, 179, 169, 151, 111, 107 |
a: indicates there are two possibilities ‘‘catechin or epicatechin; gallocatechin or epigallocatechin”; b: indicates there are two possibilities; Base peaks between parenthesis and bold.