Table 3.
Phytochemical profile of M. pulegium leaf and flower extracts (MPLE and MPFE, respectively) elucidated by LC-DAD-ESI-MS analysis. Results are expressed as mean area percentage (%) based on LC-DAD data acquired at 280 nm ± standard deviation of nine independent analyses in triplicate (n = 3) with respect to the total area of identified and unidentified (unknown) compounds.
| n. | Compound | λmax nm |
[M-H]- m/z |
MPLE (Area %) | MPFE (Area %) | ||||
|---|---|---|---|---|---|---|---|---|---|
| I | II | III | I | II | III | ||||
| 1 | Riboflavine 5’-(dihydrogen phosphate) | 300 | 455 | - | 3.34 ± 0.16 b | 19.23 ± 0.56 | - | - | 7.31 ± 0.33 |
| 2 | Epicatechin hydroxybenzoate | 272 | 409 | - | - | 0.73 ± 0.03 | 1.10 ± 0.04 a | 0.29 ± 0.01 b | 0.26 ± 0.01 |
| 3 | Gallocatechin-3-gallate § | 278 | 457 | - | - | - | - | 0.70 ± 0.03 | - |
| 4 | Epigallocatechin-3-O-gallate § | 274 | 457 | 0.37 ± 0.01 | - | - | - | - | - |
| 5 | Floridin | 256,282 | 414 | - | - | 2.48 ± 0.08 | - | - | - |
| 6 | Caffeoylhydroxycitric acid | 236,326 | 369 | - | - | - | - | - | 3.68 ± 0.15 |
| 7 | Ferulic acid hexoside | 234,322 | 355 | - | - | - | 0.68 ± 0.02 | - | - |
| 8 | Catechin hexoside | 276,320 | 451 | - | 0.28 ± 0.01 | - | - | 0.13 ± 0.00 | - |
| 9 | Coumaroylquinic acid | 216,320 | 338 | 0.72 ± 0.02 | - | - | - | - | - |
| 10 | Salvianolic acid J | 276,344 | 537 | - | - | 0.42 ± 0.02 | - | - | - |
| 11 | Epicatechin methylgallate | 278 | 455 | - | - | - | 0.38 ± 0.01 | - | - |
| 12 | Malonyl-daidzin | 264,308 | 297 | - | - | 0.72 ± 0.01 | - | - | 8.3 ± 0.27 |
| 13 | Luteolin malonyl-hexoside | 263,348 | 533 | 0.88 ± 0.03 | - | - | - | - | - |
| 14 | Apigenin apiosyl-hexoside | 268,328 | 563 | - | 5.43 ± 0.17 | - | - | 3.37 ± 0.12 | - |
| 15 | Unknown | 300 | 567 | - | - | 2.98 ± 0.12 | - | - | 0.98 ± 0.03 |
| 16 | Unknown | 300 | 391 | - | - | 1.13 ± 0.03 | - | - | 1.35 ± 0.05 |
| 17 | Epitheaflagallin 3-O-gallate § | 260,294 | 551 | - | - | - | - | 0.62 ± 0.03 b | 5.35 ± 0.18 |
| 18 | Epigallocatechin § | 278 | 305 | - | - | - | 2.07 ± 0.08 | - | - |
| 19 | Gallocatechin § | 278 | 305 | 8.31 ± 0.15 a | 1.99 ± 0.07 b | 0.64 ± 0.02 | - | - | - |
| 20 | Eriodictyol-7-O-glucoside | 296,326 | 449 | - | - | - | - | 0.99 ± 0.02 | - |
| 21 | Medioresinol § | 278 | 387 | - | - | 0.15 ± 001 | - | - | - |
| 22 | Dimethylepigallocatechin gallate | 278 | 485 | - | - | 3.52 ± 0.12 | - | - | 1.91 ± 0.05 |
| 23 | Eriodictyol § | 292,328 | 287 | - | - | - | - | 0.38 ± 0.01 | - |
| 24 | Tuberonic acid hexoside | 274,304 | 387 | - | 1.17 ± 0.04 b | 0.96 ± 0.02 | 0.35 ± 0.01 a | 1.05 ± 0.03 b | 1.68 ± 0.04 |
| 25 | Methyl-galloylgalactarate | 226,268 | 375 | 2.27 ± 0.05 | - | - | - | - | - |
| 26 | Hydroxyluteolin-xyloside | - | 433 | - | - | - | - | - | 0.20 ± 0.01 |
| 27 | Trihydroxy-methoxy-MDF-glucuronide | 274,314 | 519 | - | 0.42 ± 0.02 b | 1.08 ± 0.04 | - | - | 0.47 ± 0.02 |
| 28 | Epigallocatechin digallate | 278 | 609 | - | - | - | 0.63 ± 0.02 a | 0.38 ± 0.02 | - |
| 29 | Unknown | - | 374 | - | - | - | - | - | 0.30 ± 0.02 |
| 30 | Limocitrin§ | 280,328,379 | 375 | - | - | - | - | 0.49 ± 0.03 b | 0.24 ± 0.01 |
| 31 | Kaempferol 3-O-glucuronide § | 272,368 | 461 | - | - | - | - | - | 5.28 ± 0.12 |
| 32 | Luteolin 7-O-rutinoside § | 272,344 | 593 | 2.89 ± 0.03 a | 2.37 ± 0.14 b | 5.36 ± 0.25 | 2.98 ± 0.17 a | 1.65 ±0.04 b | 0.27 ± 0.02 |
| 33 | Kaempferol 3-O-rutinoside § | 266,323,364 | 593 | - | - | - | - | - | 0.55 ± 0.02 |
| 34 | Unknown | 250,294 | 559 | - | - | - | - | 0.25 ± 0.01 | - |
| 35 | Salvianolic acid G | 258,346 | 417 | 0.30 ± 0.01 a | 0.78 ± 0.04 b | 1.37 ± 0.02 | - | 2.40 ± 0.12 b | 1.05 ± 0.24 |
| 36 | Unknown | 256,326 | 639 | - | 0.34 ± 0.02 | - | - | - | - |
| 37 | Salvianolic acid K | 286,321 | 555 | - | - | - | - | - | 0.75 ± 0.02 |
| 38 | Ellagic acid acetyl pentoside | 256,326 | 475 | - | 0.31 ± 0.01 b | 0.59 ± 0.02 | - | 0.22 ± 0.01 | - |
| 39 | 5-Nonadecylresorcinol | 275 | 375 | - | - | - | - | - | 0.25 ± 0.01 |
| 40 | Quercetin acetyl hexoside | 262,354 | 505 | - | - | - | 0.96 0.03 | - | - |
| 41 | Todolactol A | 236,288 | 375 | - | - | - | - | - | 6.71 ± 0.22 |
| 42 | Limocitrol | 280,327,390 | 375 | - | 2.0 ± 0.08 b | 2.54 ± 0.08 | - | 1.51 ±0.05 | - |
| 43 | Caffeoyl-rosmarinic acid | 284,328 | 537 | - | - | - | - | 0.15 ± 0.00 | - |
| 44 | Valoneic acid dilactone | 298 | 469 | - | - | - | - | - | 0.5 ± 0.02 |
| 45 | Syringic acid hexose | 240,318 | 359 | 0.83 ± 0.04 | - | - | - | - | - |
| 46 | Unknown | 282,344 | 491 | - | 0.23 ± 0.01 | - | - | - | - |
| 47 | Quercetin 3-O-(6’’-O-malonyl-β-D-glucoside) § | 262,352 | 549 | - | - | 1.34 ± 0.03 | - | - | 0.85 ± 0.03 |
| 48 | Unknown | 300 | 442 | - | - | - | - | 0.09 ± 0.00 | - |
| 49 | Salvianolic acid I | 252,318,352 | 537 | 3.15 ± 0.05 a | 8.41 ± 0.22 | - | 6.82 ± 0.22 a | 8.76 ± 0.32 | - |
| 50 | Dihydroquercetin 3-rhamnoside § | 254,368 | 449 | - | - | 0.37 ± 0.02 | - | - | - |
| 51 | Apigenin 6,8-di-C-glucoside § | 244,266,334 | 593 | 0.72 ± 0.02 a | - | 1.35 ± 0.03 | 2.01 ± 0.12 a | - | 1.50 ± 0.05 |
| 52 | Salvianolic acid D § | 254,347 | 417 | 0.64 ± 0.01 a | 3.41 ± 0.11 b | 0.82 ± 0.02 | - | 0.67 ± 0.02 b | 1.24 ± 0.04 |
| 53 | Myricetin acetylhexoside | 240,374 | 521 | - | - | 1.28 ± 0.04 | - | - | - |
| 54 | Unknown | 248,312,364 | 513 | - | - | 0.81 ± 0.04 | - | - | - |
| 55 | Galloylgalactaric acid | 209,275 | 361 | 8.71 ± 0.11 | - | - | - | - | - |
| 56 | Daidzin § | 252,312 | 415 | - | - | 1.17 ± 0.02 | - | - | 0.92 ± 0.02 |
| 57 | Unknown | 240,310 | 559 | - | - | 0.45 ± 0.01 | - | - | - |
| 58 | 3,4-Dicaffeoylquinic acid § | 216,326 | 515 | - | - | 2.08 ± 0.13 | 11.64 ± 0.67 a | - | 2.06 ± 0.08 |
| 59 | Salvianolic acid B § | 244,285,336 | 717 | - | 0.25 ± 0.01 | - | 5.50 ± 0.22 a | 6.85 ± 0.28 | - |
| 60 | Isosalvianolic acid B | 254,285,340 | 717 | - | - | - | 0.79 ± 0.03 a | 6.41 ± 0.32 | - |
| 61 | Syringaresinol § | 240,271 | 417 | - | - | - | - | - | 1.22 ± 0.04 |
| 62 | Diosmin § | 260,350 | 607 | 3.61 ± 0.06 a | 1.23 ± 0.03 b | 3.33 ± 0.14 | 0.54 ± 0.02 a | 0.11 ± 0.00 b | 0.15 ± 0.01 |
| 63 | Unknown | 246,266,312 | 424 | - | - | - | - | 0.20 ± 0.01 | - |
| 64 | Salvianolic acid K | 250,270,345 | 555 | - | 0.61 ± 0.03 b | 2.95 ± 0.11 | - | 0.25 ± 0.01 | - |
| 65 | Unknown | 300 | 553 | - | - | 0.12 ± 0.00 | - | - | - |
| 66 | Rosmarinic acid § | 292,332 | 359 | 0.52 ± 0.02 a | 19.16 ± 0.48 b | 0.26 ± 0.01 | 24.31 ± 0.84 a | 25.52 ± 0.76 | - |
| 67 | Malonylglycitin | 256,320 | 531 | - | - | 0.46 ± 0.02 | - | - | - |
| 68 | Pentacosenylresorcinol | 300 | 457 | - | - | - | - | - | 0.63 ± 0.02 |
| 69 | Salvianolic acid E § | 286,314,350 | 717 | - | 6.08 ± 0.12 | - | 1.94 ± 0.06 a | 1.74 ± 0.04 | - |
| 70 | Unknown | 246,266,312 | 506 | - | - | 1.51 ± 0.04 | - | 0.05 ± 0.00 | - |
| 71 | Lithospermic acid § | 238,336 | 537 | - | - | - | 1.59 ± 0.04 a | 0.37 ± 0.02 | - |
| 72 | Unknown | 286,323 | 519 | - | 1.01 ± 0.02 | - | - | - | - |
| 73 | Salvianolic acid L | 286,314,340 | 717 | - | - | - | 2.33 ± 0.08 | - | - |
| 74 | Glucoerucin § | 217,236 | 419 | - | - | 0.6 ± 0.03 | - | 0.31 ± 0.01 | - |
| 75 | 3,5-Dicaffeoylquinic acid § | 216,322 | 515 | - | 0.22 ± 0.01 | - | - | - | 0.74 ± 0.03 |
| 76 | Quercetin hydroxybenzoylhexoside | 257,358 | 583 | 2.37 ± 0.04 | - | - | - | - | - |
| 77 | Unknown | 266,300,334 | 531 | 0.26 ± 0.01 | - | - | - | - | - |
| 78 | Isorhamnetin sulfate | 253,370 | 395 | - | - | 0.83 ± 0.02 | - | - | 1.23 ± 0.04 |
| 79 | Apigenin 8-C-α-L-arabinoside 6-C-β-D-glucoside § | 268,333 | 563 | - | - | 0.27 ± 0.01 | - | - | - |
| 80 | Rosmanol § | 262,288 | 345 | - | - | - | - | 5.51 ± 0.22 | - |
| 81 | Syringetin § | 284,370 | 345 | - | 0.22 ± 0.00 | - | 0.13 ± 0.01 | - | - |
| 82 | Salvianolic acid C § | 264,342 | 491 | - | 0.22 ± 0.01 b | 1.89 ± 0.04 | 6.04 ± 0.22 a | 0.19 ± 0.01 b | 0.88 ± 0.03 |
| 83 | Isorhamnetin 3-glucuronide § | 260,370 | 491 | - | 8.04 ± 0.32 | - | - | - | 0.45 ± 0.02 |
| 84 | Unknown | 222,290,362 | 581 | 0.28 ± 0.01 | - | - | - | - | - |
| 85 | Luteolin § | 254,266,346 | 285 | 3.65 ± 0.15 | - | - | - | - | - |
| 86 | Mangiferin gallate | 260,362 | 573 | - | 0.11 ± 0.00 | - | - | - | - |
| 87 | Peonidin § | 282,526 | 300 | - | - | - | 0.78 ± 0.04 a | 0.58 ± 0.04 | 0.65 ± 0.03 |
| 88 | Patuletin hexoside | 262,354 | 493 | - | 0.42 ± 0.02 | - | - | - | - |
| 89 | Jaceosidin § | 214,282,342 | 329 | - | 4.44 ± 0.12 b | 1.42 ± 0.05 | 1.35 ± 0.03 a | 3.50 ± 0.14 b | 2.6 ± 0.01 |
| 90 | Unknown | 216,286,402 | 328 | - | - | - | - | 0.09 ± 0.00 | - |
| 91 | Unknown | 288,312,398 | 598 | - | - | - | 1.01 ± 0.02 | - | - |
| 92 | Diosmetin 7-glucuronide § | 230,266,346 | 475 | - | - | - | - | 0.05 ± 0.00 | - |
| 93 | Salvigenin § | 284,334 | 327 | - | 0.37 ± 0.01 b | 0.96 ± 0.03 | 0.76 ± 0.03 | - | 1.15 ± 0.02 |
| 94 | Jaceidin Isomer A | 282,352 | 359 | 4.84 ± 0.18 a | 14.47 ± 0.58 b | 23.63 ± 1.05 | 15.73 ± 0.83 a | 13.45 ± 0.48 b | 30.79 ± 1.58 |
| 95 | Kaempferide § | 254,266,344 | 299 | 52.81 ± 0.64 | - | - | - | - | - |
| 96 | Jaceosidin Isomer I | 252,268,346 | 329 | - | 1.00 ± 0.04 b | 0.27 ± 0.01 | 0.73 ± 0.03 a | 0.21 ± 0.01 b | 1.51 ± 0.05 |
| 97 | Quercetin sulfate | 246,354 | 381 | - | - | - | - | 1.77 ± 0.05 | - |
| 98 | Jaceidin isomer II | 270,354 | 359 | - | 1.74 ± 0.03 b | 0.76 ± 0.03 | 0.64 ± 0.02 a | - | 1.40 ± 0.04 |
| 99 | Phloretin xylosyl-hexoside | 230,288 | 567 | - | - | 0.49 ± 0.02 | - | - | 0.36 ± 0.01 |
| 100 | 6-Methoxyapigenin § | 260,330 | 299 | - | 0.32 ± 0.01 | - | - | - | - |
| 101 | Unknown | 254,264,348 | 344 | - | - | 0.65 ± 0.03 | - | - | - |
| 102 | Apigenina-7-glucoside § | 268,330 | 431 | 0.72 ± 0.03 | - | - | - | - | - |
| 103 | Methyl digalloyl-β-D-hexopyranoside | 268,310,360 | 497 | 0.59 ± 0.01 | - | - | - | - | - |
| 104 | Dihydroxyphenyl galloyl-β-D-hexopyranoside | 252,290,342 | 439 | 0.56 ± 0.02 a | 7.14 ± 0.21 b | 0.45 ± 0.02 | 6.21 ± 0.02 a | 8.27 ± 0.14 b | 0.96 ± 0.02 |
| 105 | 5-Galloylquinic acid § | - | 343 | - | 0.28 ± 0.01 | - | - | - | - |
| 106 | Trachelogenin § | - | 387 | - | 0.07 ± 0.00 | - | - | - | - |
| 107 | Unknown | - | 381 | - | - | - | - | 0.06 ± 0.00 | - |
| 108 | Hexopyranuronosyl-xylose | 266,334 | 325 | - | 0.13 ± 0.00 | - | - | 0.09 ± 0.00 b | 0.69 ± 0.03 |
| 109 | Quercetin 4’-glucuronide § | 258,368 | 477 | - | - | 0.64 ± 0.02 | - | - | - |
| 110 | Unknown | 266,332 | 488 | - | - | - | - | 0.06 ± 0.00 | - |
| 111 | Epigallocatechin-caffeate | 274,344 | 467 | - | 1.56 ± 0.03 b | 4.0 ± 0.21 | - | - | - |
| 112 | Unknown | 276,340 | 675 | - | 0.43 ± 0.01 b | 0.94 ± 0.02 | - | 0.26 ± 0.01 b | 0.63 ± 0.02 |
§ Absolute identification by commercially available reference standards purchased from Merck (Darmstadt, Germany), Extrasynthase (Geney, France) and MedChemExpress (Sollentuna, Sweden); - not detected; a p < 0.001 vs. MPII and MPIII; b p < 0.001 vs. MPIII.