HPLC-DAD-ESI-QTOF-MS Determination of Bioactive Compounds and Antioxidant Activity Comparison of the Hydroalcoholic and Water Extracts from Two Helichrysum italicum Species
Abstract
:1. Introduction
2. Results and Discussion
2.1. Qualitative Analysis
2.1.1. Hydroxycinnamic Acids (Chlorogenic Acid Derivatives)
2.1.2. Hydroxybenzoic Acids and Their Glucosides
2.1.3. Flavonoids and Their Glycosides
2.1.4. Coumarins
2.1.5. Arzanol and Other Pyrone Derivatives
2.1.6. Other Phenolic Compounds
2.2. Semi-Quantitative and Quantitative Analysis
2.3. Antioxidant Activity
3. Materials and Methods
3.1. Reagents and Chemicals
3.2. Plant Collection
3.3. Extraction Procedures
3.4. HPLC-DAD-ESI-QTOF-MS Analysis
3.5. Antioxidant Assay
3.6. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Appendix A
No. | RT (Min) | Compound Name | Compound Formula | Molar Mass | Diff. (ppm) | m/z ESI− | MS2 ESI− | m/z ESI+ | MS2 ESI+ | UVmax (nm) | Level of Identification 1 |
---|---|---|---|---|---|---|---|---|---|---|---|
1 | 2.90 | Gallic acid glucoside | C13H16O10 | 332.0757 | −3.35 | 331.0682 | 331.1; 168.0; 125.0; 167.0; 149.9; 124.0; | NPR/MS2 | |||
2 | 4.25 | Hydroxyphthalide glucoside 1 | C14H16O9 | 328.079 | −0.24 0.92 | 327.0722 373.0773 | 165.1; 146.9; 103.0; 93.0; 77.0 | 329.0857 | 167.0; 121.0; 111.0; 149.0 | PR in [37]/MS | |
3 | 4.84 | Protocatechuic acid O−hexoside | C13H16O9 | 316.0789 | 1.83 | 315.0720 | 315.1; 152.0; 153.0; 108.0; 109.0 | 210 | NPR/MS2 | ||
4 | 5.49 | CQA−glucoside: 3−O−(4′−caffeoyl glucosyl) quinic acid | C22H28O14 | 516.1486 | −1.24 | 515.1413 | 515.1; 179.0; 341.1; 173.0; 353.1; 135.0 | NPR/MS2 | |||
5 | 5.55 | Hydroxyphthalide glucoside 2 | C14H16O9 | 328.079 | 1.17 | 327.0717 | 327.1; 165.0; 146.9; 121.0 | 207 | PR in [37]/MS | ||
6 | 5.95 | CQA−glucoside: 5−O−(4′caffeoyl glucosyl) quinic acid | C22H28O14 | 516.1469 | 1.87 | 515.1400 | 515.1; 191.1; 353.1; 341.1; 179.0; 323.1; 135.0; 161.0 | 517.1547 | 163.0; 325.1; 135.0 | 220; 324 | NPR/MS2 |
7 | 6.00 | Caffeoylquinic acid: 3−O−CQA (neochlorogenic acid) | C16H18O9 | 354.0947 | −0.11 | 353.0875 | 353.1; 191.1;179.0; 135.0; 146.9; 107.0 | 355.101 | 163.0; 145.0; 135.0; 117.0; 89.0 | PR in [14]/MS2 | |
8 | 6.08 | Vanillic acid derivative 1 | C14H18O9 | 330.0949 | 0.31 | 329.0876 | 329.1; 167.0; 123.0; 149.0; 102.9; 79.0 | 220; 204 280 | NPR/SI | ||
9 | 6.18 | Caffeic acid hexoside 1 | C15H18O9 | 342.0956 | −1.76 | 341.0884 | 179.0; 341.1; 229.9; 135.0; 205.0; 133.0 | 202 | NPR/MS2 | ||
10 | 6.28 | Hydroxybenzoic acid derivative | C14H20O9 | 332.0543 | −3.49 | 331.0471 | 165.0; 123.0; 121.0; 93.0; 77.0; 137.0; 79.0 | NPR/SI | |||
11 | 6.47 | p−Hydroxybenzoic acid | C7H6O3 | 138.0313 | 0.19 | 137.0244 | 93.0; 137.0; 65.0; 41.0; 75.0; 49.0; 67.0 | 318; 226 | PR in [24]/MS2 | ||
12 | 6.58 | CQA−glucoside: 5−O−(3′−O−caffeoyl glucosyl) quinic acid | C22H28O14 | 516.1477 | −0.31 | 515.1404 | 515.1; 323.1; 191.1; 341.1; 161.0; 85.0 | 517.1546 | 163.0; 325.1; 517.1; 145.0; 85.0; 135.0 | PR in [22]/MS2 | |
13 | 6.75 | Hydroxybenzoic acid hexoside | C13H16O8 | 300.0843 | 0.54 | 299.0771 | 137.0; 299.1; 179.0; 59.0; 93.0; 71.0; 65.0 | 213 | NPR/MS2 | ||
14 | 6.82 | Caffeic acid hexoside 2 | C15H18O19 | 342.095 | −0.14 | 341.0874 | 341.1; 179.0; 135.0; 84.9; 73.9; 153.1 | 326; 297; 194; 218; 244 | NPR/MS2 | ||
15 | 6.88 | Caffeoylquinic acid: 5−O−CQA (chlorogenic acid) | C16H18O9 | 354.0953 | 0.49 | 353.0878 | 191.0; 353.1; 161.0; 85.0; 127.0; 87.0; 133.0; 83.0 | 355.1013 | 163.0; 135.0; 117.0; 135.0; 145.0 | PR in [14,22,24]/ STD | |
16 | 7.01 | Caffeic acid hexoside 3 | C15H18O9 | 342.0951 | −0.01 | 387.0932 341.0894 | 179.0; 341.0; 135.0; 107.0 | 216; 259; 288; 330 | NPR/MS2 | ||
17 | 7.04 | Caffeoylquinic acid: 4−O−CQA (cryptochlorogenic acid) | C16H18O9 | 354.0951 | −0,07 | 353.0878 399.0944 | 191.1; 353.1; 173.0; 179.0; 161.0; 135.0; 93.0; 85.0 | 355.1011 | 163.0; 193.0; 145.0; 135.0; 117.0; 89.0; 193.0 | PR in [14]/MS2 | |
18 | 7.05 | Vanillic acid O−hexoside | C14H18O9 | 330.0951 | −0.16 | 329.0879 | 167.0; 329.1; 99.0; 230.7; 123.0; 125.0; 41.0 | NPR/MS2 | |||
19 | 7.08 | Coumaric acid hexoside 1 | C15H18O8 | 326.1009 | −2.2 | 325.0930 | 163.0; 325.1; 119.0; | 214 | PR in [8]/MS2 | ||
20 | 7.18 | Esculetin | C9H6O4 | 178.0266 | 0.2 | 177.0193 | 177.0; 133.0; 89.0; 41.0; 79.0; 53.0; | 326; 297; 194; 218; 240 | PR in [35]/MS2 | ||
21 | 7.24 | Caffeic acid | C9H8O4 | 180.0419 | 2.12 | 179.0346 | 135.0; 179.0; 164.0; 134.0; 45; 89.0 | PR in [22,35]/MS2 | |||
22 | 7.26 | Dicaffeoylhexaric acid | C23H34O14 | 534.1017 | −0.94 | 533.0939 | 371.1; 533.1; 209.0; 191.0; 85.0; 57.0; 147.0; 179.0 | NPR/MS2 | |||
23 | 7.45 | 2,4−Dihydroxybenzoic acid | C7H6O4 | 154.0259 | 4.21 | 153.0187 | 109.0; 153.0; 108.0; 65.0; 91.0 | 210; 245; 325; 295 | NPR/MS2 | ||
24 | 7.51 | Coumaric acid hexoside 2 | C15H18O8 | 326.0997 | 1.1 | 325.0925 | 265.1; 163.0; 205.0; 161.0; 145.0; 119.0; 117.0; 59.0 | 325;298; 210; 245 | PR in [8]/MS2 | ||
25 | 7.53 | Caffeoylquinic acid: cis−5−O−CQA (cis−chlorogenic acid) | C16H18O9 | 354.095 | 0.18 | 353.0878 | 191.1; 353.1; 85.0; 111.0; 127.0; 135.0 | 355.1015 | 163.0; 254.9; 145.0; 111.0; 117.0; 135.0; 89.0 | NPR/MS2 | |
26 | 7.60 | Coumaroylquinic acid | C16H18O8 | 338.1011 | −3.31 | 337.094 | 191.1; 337.1; 87.0; 69.0; 163.0; 93.0; 43.0; 67.0; | NPR/MS2 | |||
27 | 7.71 | Vanillic acid derivative 2 | C14H18O9 | 330.0955 | −0.53 | 329.088 | 167.0; 329.1; 108.0; 191.0 | 211; 204 | NPR/SI | ||
28 | 7.73 | Quercetin diglycoside | C27H30O17 | 626.15 | −1.41 | 625.1419 | 625.1; 593.1; 301.0; 463.1; 488.9; 300.0 | NPR/MS2 | |||
29 | 7.80 | Vanillic acid derivative 3 | C14H18O9 | 330.0955 | −1.89 | 329.0878 | 191.0; 167.0; 329.1; 123.0; 83.0; 81.0 | 216; 204 | NPR/SI | ||
30 | 7.97 | Kaempferol diglycoside | C27H30O16 | 610.1535 | −1.76 | 609.1472 | 609.2; 283.0; 49.4; 441.2; 285.0; 447.1; 328.0 | 200; 218; 180; 345 | NPR/MS2 | ||
31 | 7.97 | 5−O−Feruloylquinic acid | C17H20O9 | 368.1094 | −3.62 | 367.1037 | 191.1; 367.1; 173.0; 87.0; 93.0; 134.0; 85.0 | 369.1186 | 177.1; 369.1; 145.0; 117.0; 149.1 | PR in [8]/MS2 | |
32 | 8.0 | Myricetin glycoside | C21H20O13 | 480.0914 | −2.05 | 479.0842 | 479.1; 317.0; 316.0; 165.98; 139.0 | 481.0969 | 319.0; 481.1; 435.1; 169.0; 137.0 | PR in [22]/MS2 | |
33 | 8.15 | Quercetin O−hexoside 1 | C21H20O12 | 464.0959 | −0.24 | 463.0883 | 463.1; 300.0; 301.0; 137; 300.0 | PR in [20]/MS2 | |||
34 | 8.20 | 5−O−Cumaroylquinic acid | C16H18O8 | 338.1001 | −0.57 | 337.0931 | 191.1; 337.1; 145.0; 163.0, 81.0; 85.0; 93.0 | 320; 295; 195; 234 | NPR/MS2 | ||
35 | 8.3 | Dihydroxybenzoic acid derivative | C9H10O5 | 198.0532 | −2.67 | 197.455 | 197.0; 153.1; 138.0; 123.0; 109.0; 108.0; 137.0 | 320; 295; 195, 234 | NPR/SI | ||
36 | 8.37 | Dicaffeoylquinic acid glycoside | C31H34O17 | 678.1806 | −1.47 | 677.1734 | 677.2; 515.1; 353.1; 179.0; 191.1; 323.1 | NPR/MS2 | |||
37 | 8.40 | Herbacetin methyl ether | C16H12O17 | 316.0583 | 0.6 | 315.0508 | 315.0; 287.1; 255.0; 283.0; 227.0; 211.0; 183.0 | 216; 257; 291 | PR in [34]/MS2 | ||
38 | 8.42 | Caffeoyl derivative | C34H36O19 | 748.1856 | −1.71 | 747.1791 | 747.2; 585.1; 422.1; 459.1 | PR in [8]/SI | |||
39 | 8.49 | Myricetin malonylhexoside | C24H22O16 | 520.0861 | −1.39 | 565.0843 | 521.1; 317.0; 565.1; 178.9; 174.0; 161.0 | NPR/MS2 | |||
40 | 8.56 | Coumaric acid | C9H8O3 | 164.0472 | 1.06 | 163.0399 | 119.0; 163.0; 91.1; 93.0; 117.0; | 203; 228; 284; 340 | PR in [44,45]/MS2 | ||
41 | 8.59 | Quercetin O−hexoside 2 | C21H20O12 | 464.0955 | −3.28 | 463.097 | 463.1; 301.0; 300.0; 271 | 465.103 | 303.0; 465.1; 392.1; 229.0; 153.0; 285.0 | PR in [31]/MS2 | |
42 | 8.61 | Scopoletin | C10H8O4 | 192.0431 | −3.39 | 191.0359 | 176.0; 191.0; 148.0; 59; 104.0; 102.9; 120.0 | PR in [35]/STD | |||
43 | 8.64 | Quercetin malonylhexoside 1 | C24H22O15 | 550.0973 | −2.05 | 549.0897 | 505.1; 301.0; 445.1; 300.0 | NPR/MS2 | |||
44 | 8.66 | Dihydrodehyrodiconiferyl glycoside derivative 1 | C27H36O13 | 568.2157 | −0.21 | 567.2085 | 567.2; 359.1; 341.1; 521.2; 329.1; 44.9; | NPR/MS2 | |||
45 | 8.70 | Quercetin O−hexoside 3 | C21H20O12 | 464.0958 | −0.29 | 463.0882 | 463.1; 300.0; 301.0; 271.0; 255.0; 151.0 | 465.1027 | 303.0; 145.0; 85.0; 229.0; 97.0 | 196; 218: 244; 302; 328 | PR in [31]/MS2 |
46 | 8.79 | Dicaffeoyl quinic acid isomer: 3,4−diCQA | C25H24O12 | 516.1264 | 0.76 | 515.1189 | 515.1; 353.1; 203.0; 173.0; 179.0; 191.1; 135.0 | 517.1339 | 163.0; 499.1; 135.0; 145.0; 89.0; 117.0 | PR in [14]/MS2 | |
47 | 8.83 | Myricetin acetylglycoside | C23H22O14 | 522.1012 | 0.28 | 521.0935 | 521.1; 503.1; 127; 367.1; 152.0; 108.0; 179.0 | NPR/MS2 | |||
48 | 8.87 | Isorhamnetin hexoside 1 | C22H22O12 | 478.1121 | −0.09 | 477.1039 | 477.1; 315.1; 314.0; 300.0; 299.0; 271.0; 201.0; 179.0 | 196; 218: 244; 302; 328 | PR in [20]/MS2 | ||
49 | 8.90 | Dicaffeoyl quinic acid isomer: 3,5−diCQA | C25H24O12 | 516.1268 | 0.01 | 515.1193 | 353.1; 515.1; 191.1; 179.0; 135.0; 173.0; 161.0; | 517.1331 | 163.0; 499.1; 337.1; 145.0; 135.0; 117.0 | PR in [14]/MS2 | |
50 | 8.90 | Quercetin malonylhexoside 2 | C24H22O15 | 550.0963 | −0.58 | 549.0931 | 505.1; 300.4; 301.0; 287; 271.0 | 551.1028 | 303.0; 551.1; 127.0; 85.0; 109.0 | NPR/MS2 | |
51 | 9.07 | Dicaffeoyl quinic acid isomer: 1,5−diCQA | C25H24O12 | 516.1271 | −0.14 | 515.1196 | 353.1; 515.1; 191.1; 179.0; 135.0 | 517.1332 | 163.0; 499.1; 319.1; 145.0; 89.0; 117.0 | 196; 218: 244; 302; 328 | PR in [14]/MS2 |
52 | 9.11 | Tricaffeoyl hexaric acid | C33H28O17 | 696.1331 | −0.14 | 695.1255 | 695.1; 533.1; 371.1; 209.0; 85.0; 191.0 | NPR/MS2 | |||
53 | 9.17 | Dihydrodehyrodiconiferyl glycoside derivative 2 | C27H36O13 | 568.2165 | −1.4 | 567.2091 | 521.2; 491.2; 503.2; 476.2; 250.1; 329.1; 341.1; 99.0; | 196; 218: 244; 302; 328 | NPR/MS | ||
54 | 9.20 | Kaempferol glycoside | C21H20O11 | 448.101 | −1.07 | 447.0936 | 447.1; 284.0; 285.0; 255.0; 227.0 | PR in [22]/MS2 | |||
55 | 9.21 | Herbacetin | C15H10O7 | 302.0428 | −0.94 | 301.0357 | 301.0; 268.0; 133.0; 211.0; 135.0; 159.0; 132.0 | 303.0496 | 303.0; 313.0; 163.0; 137.1; 135.0; 123.0; 169.0; 285.0 | NPR/MS2 | |
56 | 9.23 | Dicaffeoyl quinic acid isomer: 4,5−diCQA | C25H24O12 | 516.1268 | −0.11 | 515.1192 | 515.1; 353.1; 173.0; 179.0; 191.1; 135.0; 93.0 | 517.1333 | 163.0; 499.1; 145.0; 135.0; 117.0 | PR in [14]/MS2 | |
57 | 9.29 | Caffeic acid O−hexoside derivative | C27H36O13 | 568.2137 | 2.16 | 567.2071 | 179.1; 521.2; 341.1; 161.0; 326.1; 89.0; 71.0 | 207; 247, 305; 325 | NPR/SI | ||
58 | 9.33 | Isorhamnetin hexoside 2 | C22H22O12 | 478.1118 | −3.25 | 477.1051 | 477.1; 315.0; 314.0; 243.0; 271.0; 285.0; 299.0 | 479.1177 | 317.1; 479.1; 85.0; 302.0; 153.0; | PR in [20]/MS2 | |
59 | 9.35 | Methoxyoxalyl dicaffeoylquinic acid | C28H26O15 | 602.128 | −1.92 | 601.121 | 395.1; 439.1; 557.1; 353.1; 233.1; 191.0; 173.0; 179.0 | PR in [8]/MS2 | |||
60 | 9.44 | Eriodictyol O−hexoside | C21H22O11 | 450.1193 | −3.96 | 449.1107 | 449.1; 287.1; 135.0; 151.0; 123.0; 152.0 | NPR/MS2 | |||
61 | 9.47 | Kaempferol acetylglycoside | C23H22O12 | 490.1121 | −5.52 | 489.1065 | 489.1; 417.0; 285.0; 284.0; 255.0; 227.0 | NPR/MS2 | |||
62 | 9.59 | Salicylic acid | C7H6O3 | 138.0313 | 0.99 | 137.0244 | 93.0; 137.0; 65.0; 53.0 | 194; 224 | PR in [8]/MS2 | ||
63 | 9.61 | 3−Feruloyl−5−caffeoylquinic acid | C26H26O12 | 530.143 | −2.38 | 529.1364 | 367.1; 529.1; 193.0; 191.1; 134.0; 113 | 531.1493 | 177.1; 513.1; 531.2; 509.0; 163.0; 145.0; 117.0 | 295; 316; 250 | NPR/MS2 |
64 | 9.66 | Quercetin O−hexoside 4 | C21H20O12 | 464.096 | −1.07 | 463.0886 | 463.1; 301.0; 151.0; 178.9; 300.0; 121.0 | 465.1027 | 303.0; 465.1; 85.0; 97.0; 153.0; 61.0 | PR in [31]/MS2 | |
65 | 9.73 | Ferulic acid | C10H10O4 | 194.0579 | −0.21 | 193.0504 | 193.0; 161.0; 134.0; 132.0; 133.0; 104.0 | PR in [8,45]/MS2 | |||
66 | 9.84 | 4−hydroxy−3−(2−hydroxy−3− isopentenyl) acetophenone 1 | C13H16O3 | 220.1095 | 1.94 | 219.1022 | 219.1; 201.1; 119.0; 218.9; 45; 189.1; 157.1; 41.0 | 196 | PR in [46]/MS | ||
67 | 9.90 | 4−Feruloyl−5−caffeoylquinic acid | C26H26O12 | 530.1433 | −3.1 | 529.1368 | 529.1;367.1; 353.1; 173.0; 193.1; 161.0 | NPR/MS2 | |||
68 | 9.98 | Quercetin coumaroylglucoside 1 | C30H26O14 | 610.1321 | −0.6 | 609.1254 | 609.1; 463.1; 300.0; 301.0; 255.0; 272.0; | 611.1393 | 147.0; 309.1; 303.0; | 208; 225; 265; 315; 360; 194; 292 | PR in [8]/MS2 |
69 | 10.04 | 4−hydroxy−3−(2−hydroxy−3− isopentenyl) acetophenone 2 | C13H16O3 | 220.1095 | 1.79 | 219.1022 | 219.1; 201.1; 119.0; 218.9; 45; 143.0; 185.1; | PR in [46]/MS | |||
70 | 10.17 | Quercetin coumaroylglucoside 2 | C30H26O14 | 610.1319 | −1.91 | 609.1253 | 609.1; 463.1; 301.0; 300.0; 151.0; 255.0; | 204; 222; 295; 330 | PR in [8]/MS2 | ||
71 | 10.24 | Eriodictyol | C15H12O6 | 288.0641 | −1.76 | 287.0566 | 151.0; 287.1; 135.0; 65.0; 68.0; 41.0 | NPR/MS2 | |||
72 | 10.27 | Tricaffeoylquinic acid | C34H30O15 | 678.1579 | 0.89 | 677.1502 | 677.2; 515.1; 631.1; 515.1; 353.1; 179.0; 173.0; 335.1; 161.0. 191.1 | NPR/MS2 | |||
73 | 10.49 | Quercetin | C15H10O7 | 302.0431 | −0.59 | 301.0356 | 301.0; 179.0; 151.0; 121.0; 65.0; 63.0; 83.0; 107.0;93.0 | 303.049 | − | 192; 225 | PR in [8]/MS2 |
74 | 10.49 | Pinocembrin derivative | C27H32O15 | 596.1749 | 1.65 | 595.1678 | 549.2; 255.1; 279.1; 297.1 | NPR/SI | |||
75 | 10.50 | Tiliroside | C30H26O13 | 594.1389 | −2.71 | 593.131 | 593.1; 285.0; 284.0; 255.0; 145.0 | 595.1456 | 147.0; 309.1; 287.1; 165.1; 291.1; 91.1 | PR in [8,20]/MS2 | |
76 | 10.53 | Luteolin | C15H10O6 | 286.0483 | −0.46 | 285.0406 | 285.0; 151.0; 133.0; 107.0; 132.0; 63.0; 65.0; | PR in [22]/STD | |||
77 | 10.91 | Isorhamnetin 1 | C16H12O7 | 316.0591 | −2.45 | 315.0518 | 315.0;300.0; 271.0; 243.0; 255.0; 227.0 | 192; 225 | PR in [8,34]/MS2 | ||
78 | 11.06 | Naringenin | C15H12O5 | 272.0683 | 0.61 | 271.061 | 271.1; 151.0; 119.0; 65.0; 63.0; 41.0 | PR in [22,47]/MS2 | |||
79 | 11.12 | Gnaphaliol glucopyranoside | C19H24O9 | 396.1423 | −0.7 | 395.135 441.1419 | 233.1; 395.1; 190.9; 146.9; 189.1; 83.0; 41.0; 191.1 | 195; 335 | PR in [37]/MS | ||
80 | 11.34 | Naringenin isomer | C15H12O5 | 272.0683 | 0.61 | 271.061 | 271.1; 253.0; 151.0; 197.1; 63.0; 65.0; 83.0; 125.0; | 273.0751 | 227.1; 153.0; 255.1; 273.1; 199.1; | 209; 292 | PR in [8]/MS2 |
81 | 11.37 | Kaempferol | C15H10O6 | 286.0477 | 0.97 | 285.0405 | 285.0; 123.0; 185.1; 169.1; 159.0; 93.0; 155.1; 117.0 | PR in [8,20,22]/ MS2 | |||
82 | 11.40 | Pinocembrin isomer | C15H12O4 | 256.0741 | −2.53 | 255.0669 | 255.1; 153.1; 213.0; 151.0; 171.0; 63.0; 65.0; 83.0 | NPR/MS2 | |||
83 | 11.63 | Isorhamnetin 2 | C16H12O7 | 316.0596 | −4.15 | 315.0525 | 315.0; 300.0; 60.7; 149.0; 271.0; 107.0; 83.0; 255.0 | PR in [8,34]/MS2 | |||
84 | 11.78 | Isokaempferide 1 | C16H12O6 | 300.0632 | 0.69 | 299.0559 | 299.1; 284.0; 256.0; 255.0; 239.0; 227.0; 132.0; 183.0 | 205; 290 | PR in [34]/MS2 | ||
85 | 11.85 | Quercetin dimethyl ether | C17H14O7 | 330.0749 | −2.53 | 329.0675 | 329.1; 314.0; 299.0; 271.0; 133.0; 215.0; | 331.0807 | 331.1; 316.1; 301.0; 273.0; 217.0; 121.0 | NPR/MS2 | |
86 | 11.90 | Micropyrone | C14H20O4 | 252.1345 | 0.01 | 251.1287 | 251.1; 207.1; 113.1; 151.1; 123.1; 85.1; 55.0 | PR in [36]/MS | |||
87 | 12.29 | Isokaempferide 2 | C16H12O6 | 300.0634 | −0.06 | 299.0567 | 299.1; 284.0; 256.0; 255.0; 239.0; 227.0; 132.0; 183.0 | 301.0707 | 301.1; 107.1; 269.2; 286.0; 285.0; 212.0 | PR in [34]/MS2 | |
88 | 13.16 | 3−Prenyl−4− hydroxyacetophenone | C13H16O2 | 204.1147 | −1.45 | 203.108 | 203.1; 148.1; 71.0; 105.0 | 197; 228; 290 | PR in [46]/MS2 | ||
89 | 13.21 | Pinocembrin | C15H12O4 | 256.074 | −1.68 | 255.0667 | 255.1; 59.0; 151.0; 187.1; 213.0; 65.0; 83.0; 137.0 | PR in [34]/STD | |||
90 | 13.81 | Gnaphaliin | C17H14O6 | 314.0797 | −2.07 | 313.07 | 313.1; 298.0; 283.0; 227.0; 255.0; 199.0; 139.1; 183.0 | 315.086 | 315.1; 300.1; 285.0; 257.0; 138.9 | 210; 280 | PR in [8,34]/MS2 |
91 | 13.87 | Galangin methyl ether | C16H12O5 | 284.0689 | −1.44 | 283.0615 | 283.1; 268.0; 211.0; 239.0; 167.1; 195.0 | 285.075 | 285.3; 270.0; 269.0; 136.0; 241.0; 168.1 | PR in [34]/MS2 | |
92 | 15.53 | Heliarzanol 1 | C24H30O8 | 446.1941 | −0.8 | 445.1871 | 445.2; 279.1; 291.1; 235.1; 247.1; 205.1; 193.1; 191.1; | 210; 295 | PR in [44]/MS | ||
93 | 15.65 | Arzanol | C22H26O7 | 402.167 | −1.95 | 401.1606 | 401.2; 235.1; 247.1; 153.1; 191.1; 109.1; 205.1; 166.0; | 403.1743 | 249.1; 347.1; 237.1; 181.0; 403.2; 155.1; 193.0; 163.1; | PR in [8,36]/STD | |
94 | 16.21 | Helipyrone | C17H20O6 | 320.1258 | −1.09 | 319.1189 | 153.1; 109.1; 198.1; 41.0 | 321.1318 | 155.1; 321.1; 167.1; 139.1; 81.1; 57.0; 43.0 | 210; 230; 295 | PR in [8,36]/MS2 |
95 | 16.57 | Italipyrone 1 | C22H24O7 | 400.1531 | −0.66 | 399.1452 | 233.1; 399.1; 245.1; 153.1;109.1; 189.1 | 401.1601 | 401.2; 247.1; 235.1; 167.1; 187.0 | 19894 | PR in [36]/MS |
96 | 16.69 | 3−Methylarzanol | C23H28O7 | 416.1836 | −0.23 | 415.1769 | 415.2; 261.1; 249.1; 205.1; 180.0; 153.1; 109.1; 193.1 | 417.1909 | 263.1; 251.1; 361.1; 195.1; 155.1; 207.1; 177.1; 189.1 | 199; 225; 275 | PR in [8,48]/MS2 |
97 | 17.45 | Arzanol derivative | C31H36O10 | 568.2318 | −2.35 | 567.2249 | 567.2; 401.2; 413.2; 247.1; 235.1; 221.1; 191.1; 179.0 | 208; 295 | NPR/SI | ||
98 | 17.92 | Arzanol isomer | C22H26O7 | 402.167 | −1.95 | 401.1606 | 401.2;235.1; 153.1; 247.1; 109.1; 179.0; 166.0; 191.1 | 215; 295 | NPR/MS2 | ||
99 | 17.97 | Heliarzanol 2 | C24H30O8 | 446.1956 | −4.58 | 445.1888 | 445.1; 279.1; 291.1; 261.1; 109.1 | PR in [44]/MS | |||
100 | 18.73 | Italipyrone 2 | C22H24O7 | 400.1533 | −3.82 | 399.1455 | 233.1; 399.1; 245.1; 153.1; 109.1; 189.1 | 401.1595 | 401.2;235.1; 247.1; 193.0 | 292; 214 | PR in [36]/MS |
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Sample | Chlorogenic Acid | Arzanol | TPC 1 |
---|---|---|---|
HII MWE | 4.6 ± 0.1 | 2.9 ± 0.1 | 31.4 ± 0.9 |
HIT MWE | 5.7 ± 0.3 | 2.1 ± 0.2 | 84 ± 3 |
HII EWE | 5.2 ± 0.2 | 6.72 ± 0.07 | 40.0 ± 0.7 |
HIT EWE | 5.1 ± 0.1 | 3.50 ± 0.05 | 83.1 ± 0.5 |
HII HWE | 4 ± 1 | <LOD | 19 ± 5 |
HIT HWE | 5 ± 1 | <LOD | 43 ± 6 |
HII CWE | <2.1 | <LOD | 40 ± 1 |
HIT CWE | 3 ± 1 | <LOD | 153 ± 1 |
Sample | EC50 [µg/mL] | Inhmax [%] | mg AAE/g Dry Mass |
---|---|---|---|
Ascorbic acid | 3.5 | 90.2 | / |
HII MWE | 26 ± 1 a,b | 83 ± 3 | 30 ± 3 a |
HIT MWE | 15 ± 1 | 82.75 ± 0.07 | 104 ± 33 c |
HII EWE | 20 ± 1 | 83.0 ± 0.6 | 44 ± 2 a |
HIT EWE | 19 ± 7 | 83 ± 2 | 66 ± 5 |
HII HWE | 41 ± 4 a,d | 83.2 ± 0.9 d | 22 ± 20 d |
HIT HWE | 29 ± 4 e | 82.8 ± 0.8 e | 28 ± 29 e |
HII CWE | 268 ± 67 a | 75 ± 5 a | 3.8 ± 0.3 a |
HIT CWE | 171 ± 63 | 86.6 ± 0.9 | 5.7 ± 0.9 |
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Kramberger, K.; Barlič-Maganja, D.; Bandelj, D.; Baruca Arbeiter, A.; Peeters, K.; Miklavčič Višnjevec, A.; Jenko Pražnikar, Z. HPLC-DAD-ESI-QTOF-MS Determination of Bioactive Compounds and Antioxidant Activity Comparison of the Hydroalcoholic and Water Extracts from Two Helichrysum italicum Species. Metabolites 2020, 10, 403. https://doi.org/10.3390/metabo10100403
Kramberger K, Barlič-Maganja D, Bandelj D, Baruca Arbeiter A, Peeters K, Miklavčič Višnjevec A, Jenko Pražnikar Z. HPLC-DAD-ESI-QTOF-MS Determination of Bioactive Compounds and Antioxidant Activity Comparison of the Hydroalcoholic and Water Extracts from Two Helichrysum italicum Species. Metabolites. 2020; 10(10):403. https://doi.org/10.3390/metabo10100403
Chicago/Turabian StyleKramberger, Katja, Darja Barlič-Maganja, Dunja Bandelj, Alenka Baruca Arbeiter, Kelly Peeters, Ana Miklavčič Višnjevec, and Zala Jenko Pražnikar. 2020. "HPLC-DAD-ESI-QTOF-MS Determination of Bioactive Compounds and Antioxidant Activity Comparison of the Hydroalcoholic and Water Extracts from Two Helichrysum italicum Species" Metabolites 10, no. 10: 403. https://doi.org/10.3390/metabo10100403