Table 5.
Secondary metabolites in Echinops ritro extracts.
| No. | Identified/Tentatively Annotated Compound | Molecular Formula | Exact Mass [M-H]− |
tR (min) |
Δ ppm | Distribution |
|---|---|---|---|---|---|---|
| Hydroxybenzoic acids, hydroxycinnamic acids, phenylethanoid glycosides and coumarins | ||||||
| 1 | protocatechuic acid-O-hexoside | C13H16O9 | 315.0727 | 1.67 | 1.316 | A, B |
| 2 | vanillic acid-O-hexoside b | C14H18O9 | 329.0875 | 1.76 | −0.381 | A, B |
| 3 | protocatechuic acid a | C7H6O4 | 153.0181 | 2.01 | −8.247 | A, B |
| 4 | vanillyl alcohol-hexoside b | C14H20O8 | 315.1085 | 2.12 | 1.299 | A, B |
| 5 | p-hydroxyphenylacetic acid O-hexoside b | C14H18O8 | 313.0929 | 2.13 | 3.926 | A, B |
| 6 | syringic acid-O-hexoside b | C15H20O10 | 359.0985 | 2.29 | 0.473 | A, B |
| 7 | hydroxybenzoic acid-O-hexoside b | C13H16O8 | 299.0778 | 2.43 | 0.800 | A, B |
| 8 | p-hydroxyphenylacetic acid b | C8H8O3 | 151.0401 | 2.50 | −8.789 | A, B |
| 9 | gentisic acid-O-hexoside b | C13H16O9 | 315.0727 | 2.55 | 1.316 | A, B |
| 10 | syringic acid-O-pentoside b | C14H18O9 | 329.0878 | 2.69 | 1.199 | A, B |
| 11 | aesculetin-O-hexoside b | C15H15O9 | 339.0724 | 2.71 | 0.515 | A, B |
| 12 | syringyl-O-hexose b | C15H20O10 | 359.0984 | 2.76 | 2.952 | A, B |
| 13 | 4-hydroxybenzoic acid a,b | C7H6O3 | 137.0230 | 2.84 | −10.928 | A, B |
| 14 | hydroxybenzoic acid-O-hexoside isomer b | C13H16O8 | 299.0778 | 3.00 | −2.443 | A, B |
| 15 | p-hydroxyphenylacetic acid O-hexoside isomer b | C14H18O8 | 313.0929 | 3.01 | 0.030 | A, B |
| 16 | O-caffeoyl hexose b | C15H18O9 | 341.0871 | 3.08 | −2.068 | A, B |
| 17 | quinic acid b | C7H12O6 | 191.0549 | 3.15 | −6.079 | A, B |
| 18 | p-hydroxyphenylacetic acid O-hexoside isomer b | C14H18O8 | 313.0929 | 3.30 | 0.030 | B |
| 19 | coumaric acid-O-hexoside b | C15H18O8 | 325.0930 | 3.33 | −1.386 | A, B |
| 20 | p-coumaric acid a,b | C9H8O3 | 163.0389 | 3.35 | −6.547 | A, B |
| 21 | shikimic acid b | C7H10O5 | 173.0455 | 3.37 | −5.875 | A, B |
| 22 | aesculetin b | C9H6O4 | 177.0193 | 3.46 | −6.225 | A, B |
| 23 | vanillyl alcohol- (acetyl)-hexoside b | C16H22O9 | 357.1191 | 3.47 | 3.681 | A, B |
| 24 | caffeic acid a,b | C9H8O4 | 179.0339 | 3.55 | −6.211 | A, B |
| 25 | hydroxybenzoic acid-dihexoside b | C19H26O13 | 461.1301 | 3.63 | −0.399 | A, B |
| 26 | ferulic acid a,b | C10H10O4 | 193.0494 | 3.79 | −6.330 | A, B |
| 27 | gentisic acid a,b | C7H6O4 | 153.0180 | 3.86 | −8.443 | A, B |
| 28 | o-coumaric acid a,b | C9H8O3 | 163.0389 | 4.56 | −7.160 | A |
| 29 | vanillic acid a | C8H8O4 | 167.0338 | 4.78 | −7.376 | A |
| 30 | caffeic acid-(salicyl)-dihexoside b | C28H32O16 | 623.1618 | 5.78 | 1.833 | A, B |
| 31 | gentisic acid-(caffeoyl)-hexoside b | C22H22O12 | 477.1038 | 6.53 | −2.996 | A, B |
| 32 | protocatechuic acid-(salicyl)-hexoside b | C20H20O11 | 435.0933 | 7.65 | 1.208 | A, B |
| Mono-, diacyl- and triacylquinic acids and their hexosides | ||||||
| 33 | 1-caffeoylquinic acid b | C16H18O9 | 353.0876 | 1.89 | −0.893 | A, B |
| 34 | neochlorogenic (3-caffeoylquinic) acid a | C16H18O9 | 353.0867 | 2.36 | −0.100 | A, B |
| 35 | caffeoylquinic acid-hexoside b | C22H27O14 | 515.1395 | 2.86 | 1.420 | A, B |
| 36 | 3-p-coumaroylquinic acid b | C16H18O8 | 337.0928 | 3.02 | −2.524 | A, B |
| 37 | chlorogenic (5-caffeoylquinic) acid a | C16H18O9 | 353.0874 | 3.19 | −1.233 | A, B |
| 38 | 4-caffeoylquinic acid b | C16H18O9 | 353.0878 | 3.37 | −0.100 | A, B |
| 39 | 3-feruloylquinic acid b | C17H20O9 | 367.1040 | 3.44 | 1.402 | A |
| 40 | caffeoylquinic acid-hexoside b | C22H27O14 | 515.1395 | 3.74 | 1.420 | A, B |
| 41 | 5-caffeoylquinic acid isomer | C16H18O9 | 353.0874 | 3.89 | 1.543 | A, B |
| 42 | 5-p-coumaroylquinic acid b | C16H18O8 | 337.0928 | 3.95 | −0.180 | A, B |
| 43 | 3-caffeoyl-5-hydroxy-dihydrocaffeoylquinic acid b | C25H26O13 | 533.1288 | 4.02 | 1.043 | A, B |
| 44 | 4-hydroxy-dihydrocaffeoyl-5-caffeoylquinic acid b | C25H26O13 | 533.1288 | 4.24 | 4.232 | A, B |
| 45 | 5-feruloylquinic acid b | C17H20O9 | 367.1034 | 4.41 | −0.096 | A, B |
| 46 | 1-caffeoyl-3-hydroxy-dihydrocaffeoylquinic acid b | C25H26O13 | 533.1288 | 4.43 | 1.043 | A, B |
| 47 | 4-feruloylquinic acid b | C17H20O9 | 367.1034 | 4.66 | 1.157 | A, B |
| 48 | dicaffeoylquinic acid-hexoside | C31H34O17 | 677.1723 | 5.17 | 2.492 | A, B |
| 49 | dicaffeoylquinic acid-hexoside isomer | C31H34O17 | 677.1723 | 5.25 | 2.580 | A, B |
| 50 | 1-hydroxy-dihydrocaffeoyl-3-caffeoylquinic acid b | C25H26O13 | 533.1288 | 5.06 | 1.831 | A, B |
| 51 | dicaffeoylquinic acid-hexoside isomer b | C31H34O17 | 677.1723 | 5.66 | 2.403 | B |
| 52 | 3,4-dicaffeoylquinic acid a,b | C25H24O12 | 515.1190 | 5.69 | 1.321 | A, B |
| 53 | 3,5-dicaffeoylquinic acid a,b | C25H24O12 | 515.1189 | 5.85 | 2.020 | A, B |
| 54 | 3-caffeoyl-5-dehydrocaffeoylquinic acid b | C25H22O12 | 513.1018 | 5.87 | −3.974 | A, B |
| 55 | 1,5-dicaffeoylquinic acid a,b | C25H24O12 | 515.1190 | 6.03 | 0.720 | A, B |
| 56 | 4,5-dicaffeoylquinic acid a,b | C25H24O12 | 515.1190 | 6.22 | −1.163 | A, B |
| 57 | 3-caffeoyl-5-p-coumaroylquinic acid b | C25H24O11 | 499.1251 | 6.53 | 1.513 | A, B |
| 58 | 4-p-coumaroyl-5-caffeoylquinic acid b | C25H24O11 | 499.1252 | 6.92 | −0.630 | A, B |
| 59 | 4-feruloyl-5-caffeoylquinic acid b | C26H26O12 | 529.1356 | 7.09 | −0.490 | A, B |
| 60 | 3,4,5-tricaffeoylquinic acid a,b | C34H30O15 | 677.1528 | 7.78 | 2.417 | A, B |
| Flavonoids | ||||||
| 61 | kaempferol O-dihexoside b | C27H30O16 | 609.1464 | 4.45 | −1.629 | A, B |
| 62 | eriodyctiol O-dihexoside b | C27H32O16 | 611.1618 | 4.65 | −0.324 | A, B |
| 63 | rutin a,b | C27H30O16 | 609.1464 | 5.09 | 2.121 | A, B |
| 64 | isoquercitrin a | C21H20O12 | 463.0885 | 5.15 | 0.585 | A, B |
| 65 | luteolin 7-O-rutinoside a,b | C27H30O15 | 593.1512 | 5.22 | 1.832 | A, B |
| 66 | patuletin O-rutinoside b | C28H32O17 | 639.1567 | 5.22 | 2.484 | B |
| 67 | hyperoside a | C21H20O12 | 463.0885 | 5.29 | 0.585 | A, B |
| 68 | luteolin-O-hexuronide b | C21H18O12 | 461.0736 | 5.37 | 0.718 | A, B |
| 69 | luteolin-7-O-glucoside a,b | C21H19O11 | 447.0934 | 5.39 | 0.348 | A, B |
| 70 | patuletin O-hexoside b | C22H22O13 | 493.0987 | 5.45 | 1.655 | A, B |
| 71 | quercetin O-acetylhexoside b | C23H22O13 | 505.0988 | 5.60 | 2.210 | A, B |
| 72 | kaempferol 3-O-rutinoside a,b | C27H30O15 | 593.1512 | 5.64 | 1.630 | A, B |
| 73 | isorhamnetin 3-O-rutinoside a,b | C28H32O17 | 623.1618 | 5.78 | 2.025 | A, B |
| 74 | apigenin O-rutinoside b | C27H30O14 | 577.1563 | 5.81 | 1.960 | A, B |
| 75 | kaempferol-3-O-glucoside a,b | C21H19O11 | 447.0934 | 5.86 | 0.348 | A, B |
| 76 | isorhamnetin 3-O-glucoside a,b | C22H21O12 | 477.1044 | 6.01 | 1.092 | A, B |
| 77 | apigenin 7-O-glucoside a,b | C21H19O10 | 431.0980 | 6.07 | −0.881 | A, B |
| 78 | apigenin O-hexuronide | C21H18O11 | 445.0774 | 6.12 | −0.617 | A, B |
| 79 | kaempferol O-acetylhexoside b | C23H22O12 | 489.1038 | 6.29 | 1.433 | A, B |
| 80 | chrysoeriol O-hexoside b | C22H22O11 | 461.1093 | 6.31 | 0.684 | A, B |
| 81 | chrysoeriol O-hexuronide b | C22H20O12 | 475.0885 | 6.33 | 0.381 | A, B |
| 82 | isorhamnetin O-acetylhexoside b | C24H24O13 | 519.1144 | 6.47 | 1.707 | B |
| 83 | jaceosidine O-hexoside b | C23H24O12 | 491.1195 | 6.50 | 1.875 | A, B |
| 84 | eupatorin O-hexoside b | C24H26O12 | 505.1351 | 6.67 | 2.139 | A, B |
| 85 | cirsimaritin O-hexoside b | C23H24O11 | 475.1246 | 6.76 | 1.379 | A, B |
| 86 | luteolin O-acetylhexoside b | C23H22O12 | 489.1038 | 6.85 | 2.312 | B |
| 87 | luteolin a,b | C15H9O7 | 285.0406 | 7.58 | 0.346 | A, B |
| 88 | patuletin b | C16H12O8 | 331.0464 | 7.70 | 1.388 | B |
| 89 | apigenin O-acetylhexoside b | C23H22O11 | 473.1089 | 7.82 | 1.406 | A, B |
| 90 | apigenin a,b | C15H9O5 | 269.0455 | 8.61 | −0.285 | A, B |
| 91 | hispidulin b | C16H12O6 | 299.0561 | 8.84 | 0.430 | A, B |
| 92 | cirsiliol b | C17H14O7 | 329.0677 | 8.87 | 1.045 | A, B |
| 93 | chrysoeriol a,b | C16H12O6 | 299.0561 | 8.92 | 0.330 | A, B |
| 94 | spinacetin b | C17H14O8 | 345.0616 | 8.99 | 0.897 | A, B |
| 95 | apigenin-O-(p-coumaroyl)hexoside | C30H26O12 | 577.1341 | 9.02 | 1.665 | A, B |
| 96 | apigenin-O-(p-coumaroylhexoside) isomer | C30H26O12 | 577.1341 | 9.07 | 1.872 | A, B |
| 97 | quercetagetin-3,6,3′(4′)-trimethyl ether b | C18H16O8 | 359.0772 | 9.07 | 1.196 | B |
| 98 | isorhamnetin a,b | C16H12O7 | 315.0512 | 9.11 | 0.870 | A, B |
| 99 | jaceosidin (6-hydroxyluteolin-6,3′-dimethyl ether) a,b | C17H14O7 | 329.0677 | 9.14 | 1.319 | A, B |
| 100 | naringenin O-(p-coumaroyl)hexoside | C30H28O12 | 579.1497 | 9.15 | 1.241 | A, B |
| 101 | naringenin O-(p-coumaroylhexoside) isomer | C30H28O12 | 579.1497 | 9.25 | 0.871 | A, B |
| 102 | axillarin b | C17H14O8 | 345.0616 | 9.25 | 1.042 | A, B |
| 103 | quercetin-7,3′(4′)-dimethyl ether b | C17H14O7 | 329.0677 | 9.44 | 1.319 | A, B |
| 104 | cirsimaritin b | C17H14O6 | 313.0719 | 10.38 | 1.401 | A, B |
| 105 | eupatilin a,b | C18H16O7 | 343.0812 | 10.67 | 0.653 | A, B |
| 106 | ayanin b | C18H16O7 | 343.0812 | 11.03 | 0.390 | A, B |
| 107 | genkwanin a,b | C16H12O5 | 283.0612 | 11.59 | −0.103 | A, B |
| 108 | ayanin isobar b | C18H16O7 | 343.0812 | 11.76 | 0.653 | A, B |
a Identified by comparison with an authentic standard; b reported for the first time in E. ritro; A—flower head extract; B—leaf extract.