Table 3.
Identification of phenolic compounds using liquid chromatography–electrospray quadrupole-time of flight mass spectrometry (LC-ESI-QTOF/MS).
| Peak | Name | Formula | m/z cal [M-H]- |
OH | OM | OC | Reference/Specie | |||
|---|---|---|---|---|---|---|---|---|---|---|
| m/z exp [M-H]- |
Dif (ppm) |
m/z exp [M-H]- |
Dif (ppm) |
m/z exp [M-H]- |
Dif (ppm) |
|||||
| 1 | Methyl 4,6-O-di-O-galloyl-β-d-glucopyranoside/Methyl 6-O-digalloyl-β-d-glucopyranoside I/II | C21 H22 O14 | 497.0937 | 497.0953 | 3.23 | 497.0941 | 0.79 | - | - | Sanguisorba officinalis. |
| 2 | Tuliposide F/Cachinoside IV | C16 H24 O11 | 391.1246 | 391.1254 | 2.08 | 391.1243 | 0.51 | - | - | Tulipa turkestani/Campsis grandiflora |
| 3 | 5,7,8-trihydroxycoumarin-5-β-glucopyranoside | C15 H16 O10 | 355.0671 | 355.0667 | 0.98 | - | - | - | - | Polytrichum formosum |
| 4 | 1-O-(4-Hydroxybenzoyl)-β-d-glucose | C13 H16 O8 | 299.0772 | 299.0771 | 0.62 | - | - | - | - | Crocus sativus (pollen) y Luffa cylindrica |
| 5 | (2R)- and (2S)-3′,4′,5,6-tetrahydroxyflavanone 7-O-β-glucopyranoside/(2R)- and (2S)-3′,4′,5,8-tetrahydroxyflavanone 7-O-β-glucopyranoside | C21 H22 O12 | 465.1022, 465.1033/465.1023, 465.1029 | 465.1054 | 3.81 | - | - | - | - | [24] |
| 6 | Deacetyl asperulosidic acid/Teveside/Monotropein | C16 H22 O11 | 389.1089 | 389.1101 | 2.97 | 389.1087 | 0.02 | 389.1075 | 3.75 | Lasianthus acuminatissimus, Morinda citrifolia (fruit), Daphniphyllum macropodum, Lasianthus wallichi, Gardenia jasminoides/Thevetia neriifolia, Lippia citriodora, Lemon verbena/Cornus suecica, Morinda officinalis, Galium glaucum, Monotropa hypopitys, M. uniflora, Pyrola japonica, Arctostaphylos uva-ursi |
| 7 | Apigenin 6,8-di-C-glucoside/Kaempferol-3-O-rutinoside | C27 H30 O15 | 593.1512 | 593.1537 | 4.11 | - | - | - | - | [25,26] |
| 8 | (1R,2R)-5′-hydroxyjasmonic 5′-O-β-d-glucopiranoside acid/tuberonic glicoside acid | C18 H28 O9 | 387.1661 | 387.1668 | 2.00 | 387.1664 | 0.91 | 387.1646 | 3.89 | Thymus vulgaris, Perilla frutescens, Lippia citriodora. |
| 9 | (2R)- and (2S)-3′,4′,5,6-tetrahydroxyflavanone 7-O-β-glucopyranoside/(2R)- and (2S)-3′,4′,5,8-tetrahydroxyflavanone 7-O-β-glucopyranoside | C21 H22 O12 | 465.1022, 465.1033/465.1023, 465.1029 | 465.1055 | 3.51 | 465.1048 | 2.02 | 465.1032 | 1.31 | [24] |
| 10 | 6-Hydroxyluteolin-7-O-hexoside | C21 H20 O12 | 463.0877 | 463.0899 | 3.65 | 463.0891 | 2.01 | 463.0873 | 2.05 | [9,24] |
| 11 | (2R)- and (2S)-3′,4′,5,6-tetrahydroxyflavanone 7-O-β-glucopyranoside/(2R)- and (2S)-3′,4′,5,8-tetrahydroxyflavanone 7-O-β-glucopyranoside | C21 H22 O12 | 465.1022, 465.1033/465.1023, 465.1029 | 465.1050 | 2.54 | 465.1050 | 2.39 | 465.1023 | 3.31 | [24] |
| 12 | Verbascoside/Isoverbascoside/Forsitoside A | C29 H36 O15 | 623.1981 | 623.2023 | 4.21 | 623.2008 | 3.50 | 623.2007 | 0.26 | [24] |
| 13 | 3-Hydroxyphloretin 6′-O-hexoside | C21 H24 O11 | 451.1246 | - | - | 451.1252 | 1.47 | 451.1241 | 1.18 | [9] |
| 14 | (a) | C30 H28 O15 | 627.1355 | - | - | 627.1378 | 0.62 | - | - | - |
| 15 | Taxifolin | C15 H12 O7 | 303.0505 | 303.0511 | 0.24 | 303.0503 | 2.36 | 303.0571 | 6.65 | Standard |
| 16 | Cosmoside | C21 H20 O10 | 431.0984 | 431.0989 | 0.53 | 431.0989 | 2.37 | 431.0957 | 6.22 | Standard |
| 17 | Phlorizin | C21 H24 O10 | 435.1297 | 435.1302 | 0.90 | 435.1307 | 2.27 | 435.1283 | 3.22 | Standard |
| 18 | 4-methoxyphenyl 1-O-β-d-[5-O-(3,4-dimethoxybenzoyl)]-apio-furanosyl-(1-6)-β-d-glucopiranoside | C27 H34 O14 | 581.1876 | 581.1886 | 1.83 | - | - | - | - | Tabebuia impetiginosa |
| 19 | (b) | C21 H24 O9 | 419.1348 | 419.1347 | 0.13 | - | - | - | - | - |
| 20 | Eriodictyol | C15 H12 O6 | 287.0569 | 287.0554 | 2.55 | 287.0576 | 6.69 | 287.0581 | 11.89 | Standard |
| 21 | 2′′-O-(3′′′,4′′′-dimethoxybenzoyl) orientin | C30 H28 O14 | 611.1406 | 611.1413 | 1.12 | 611.1424 | 2.82 | 611.1393 | 2.24 | Trollius ledebourii (flowers). |
| 22 | Ikarisoside F | C31 H36 O14 | 631.2032 | - | - | 631.2057 | 3.85 | - | - | Epimedium koreanum, E. Sagittatum, E. pubescens, E. wushanense, E. brevicornum |
| 23 | 6′′-O-p-hidroxybenzoyliridyn | C31 H30 O15 | 641.1512 | - | - | 641.1531 | 2.90 | - | - | Belamcanda chinensis |
| 24 | (c) | C23 H32 O18 | 595.1516 | - | - | 595.1494 | 3.65 | 595.1426 | 5.23 | - |
| 25 | Quercetin | C15 H10 O7 | 301.0354 | 301.0346 | 1.62 | 301.0353 | 0.19 | 301.0329 | 7.59 | Standard |
| 26 | Sinapic C-hexoside acid | C17 H22 O10 | 385.1140 | 385.1138 | 0.58 | - | - | - | - | [25] |
| 27 | (d) | C18 H26 O7 | 353.1606 | - | - | - | - | 353.1595 | 3.18 | - |
| 28 | Phloretin | C15 H14 O5 | 273.0763 | 273.0755 | 4.82 | 273.0768 | 0.10 | 273.0774 | 10.90 | [24] |
| 29 | Naringenin | C15 H12 O5 | 271.0612 | 271.0604 | 3.05 | 271.0609 | 1.24 | 271.0593 | 6.96 | Standard |
| 30 | Hispidulin | C16 H12 O6 | 299.0561 | 299.0551 | 3.35 | 299.0559 | 0.77 | 299.0568 | 7.06 | Standard |
| 31 | Diterpenic taxoid | C30 H42 O12 | 593.2662/593.2604 | 593.2632 | 4.73/5.04 | - | - | - | - | - |
| 32 | Cirsimaritin | C17 H14 O6 | 313.0718 | 313.0705 | 4.03 | 313.0718 | 0.17 | 313.0723 | 5.12 | [9,12] |
| 33 | Pinocembrin | C15 H12 O4 | 255.0663 | 255.0673 | 3.99 | 255.0657 | 1.89 | 255.0644 | 7.50 | Standard |
| 34 | Galangin | C15 H10 O5 | 269.0501 | 269.0463 | 2.76 | 269.0451 | 1.66 | 269.0434 | 8.13 | Standard |
| 35 | Genkwanin | C16 H12 O5 | 283.0612 | 283.0605 | 0.01 | 283.0608 | 1.30 | 283.0620 | 8.12 | Standard |
| 36 | Diterpenic quinone | C20 H26 O3 | 313.1809 | - | - | 313.1814 | 1.63 | - | - | - |
| 37 | (e) | C20 H24 O4 | 327.1602 | - | - | 327.1599 | 0.71 | - | - | - |
| 38 | 13(R)-Hydroxy-octadeca-(9Z,11E,15Z)-trien-oic acid/Higrosforone F | C18 H30 O3 | 293.2122 | 293.2112 | 3.55 | - | - | - | - | Potamogeton lucens/Hygrophorus persoonii |
| 39 | (f) | C23 H46 O16 | 577.2713 | 577.2690 | 4.00 | - | - | - | - | - |
| 40 | (S)-cariolic acid/coronaric acid | C18 H32 O3 | 295.2279 | 295.2270 | 2.85 | - | - | - | - | Hernandia sonora/Chysantemun coronarium |
| 41 | (g) | C37 H28 O8 | 599.1711 | 599.1706 | 0.97 | - | - | - | - | - |
| 42 | Diterpenic quinone | C20 H26 O3 | 313.1809 | - | - | - | - | 313.1795 | 4.69 | - |
| 43 | Sesquiterpene | C15 H22 O4 | 265.1445 | - | - | - | - | 265.1459 | 5.01 | - |
| 44 | Chalcone | C25 H28 O5 | 407.1864 | 407.1858 | 1.41 | - | - | - | - | - |
| 45 | Lancilactone B | C30 H38 O4 | 461.2691 | - | - | 461.2694 | 0.74 | 461.2692 | 1.26 | Kadsura lancilimba |
| 46 | Diterpenic quinone | C20 H26 O3 | 313.1809 | - | - | 313.1808 | 0.53 | 313.1796 | 4.27 | - |
| 47 | Lancilactone B | C30 H38 O4 | 461.2697 | - | - | 461.2705 | 1.74 | - | - | Kadsura lancilimba |
| 48 | Diterpene | C20 H24 O3 | 311.1653 | - | - | - | - | 311.1641 | 3.78 | - |
| 49 | Flavonoid | C25 H28 O4 | 391.1915 | 391.1902 | 3.35 | - | - | - | - | - |
| 50 | Camaric acid | C35 H52 O6 | 567.3691 | - | - | - | - | 567.3688 | 0.23 | Lantana camara (aerial parts), Lantana cujabensis. |
| 51 | Flavonoid | C25 H28 O4 | 391.1915 | - | - | 391.1923 | 2.15 | - | - | - |
| 52 | Salviol | C20 H30 O2 | 301.2173 | - | - | 301.2172 | 0.48 | 301.2177 | 4.06 | [12] |
| 53 | Grandidone D | C40 H48 O8 | 655.3276 | - | - | - | - | 655.3278 | 0.30 | Plectranthus grandidentatus. |
| 54 | Flavonoid | C25 H26 O5 | 405.1707 | 405.1693 | 3.52 | - | - | - | - | - |
| 55 | Lespedezol B3 | C40 H36 O9 | 659.2287 | 659.2277 | 1.49 | - | - | - | - | Lespedeza homoloba. |
| 56 | Lantadene A/B | C35 H52 O5 | 551.3742 | 551.3721 | 3.75 | - | - | - | - | Lantana camara, Cardia multispicata. |
| 57 | Lancilactone B | C30 H38 O4 | 461.2684 | - | - | - | - | 461.2684 | 2.91 | Kadsura lancilimba |
| 58 | Anthron | C30 H36 O4 | 459.2541 | 459.2519 | 4.53 | - | - | - | - | - |
| 59 | (h) | C19 H30 O6 | 353.1969 | 353.1988 | 4.78 | - | - | - | - | - |
| 60 | (i) | C36 H60 O8 | 619.4215 | 619.4208 | 0.38 | - | - | - | - | - |
| 61 | (j) | C48 H82 O5 | 737.6089 | - | - | 737.6073 | 2.32 | - | - | - |
| 62 | (k) | C28 H44 O11 | 555.2811 | 555.2845 | 6.22 | 555.2847 | 6.62 | 555.2843 | 4.01 | - |
OH: oregano from Huejuquilla, OM: oregano from Mezquitic, OC: oregano from Colotlan.