(−)-Epicatechin—An Important Contributor to the Antioxidant Activity of Japanese Knotweed Rhizome Bark Extract as Determined by Antioxidant Activity-Guided Fractionation
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals and Materials
2.2. The Preparation, Extraction Yield, and Antioxidant Activity of Various Extracts
2.3. Comparison between the Antioxidant Activities of the 70% Ethanol(aq) Extract of Japanese Knotweed Rhizome Bark and Ascorbic Acid over Time
2.4. SEC-HPLC-UV Fractionation of the 70% Ethanol(aq) JKRB Extract Guided by an On-Line Post-Column Reaction with DPPH
2.5. Analyses of SEC Fractions and Determination of the Strongest Antioxidant by RP-HPLC-MS
2.6. Identification of the Compounds in the Antioxidant Fraction by Orthogonal Methods and Confirmation of Their Antioxidant Activity by DPPH Assay
3. Results and Discussion
3.1. Extraction Yields and Antioxidant Activity of Various Extracts
3.2. Antioxidant Activity over Time—Ascorbic Acid Compared to the JKRB 70% Ethanol(aq) Extract
3.3. SEC-HPLC Fractionation of the JKRB 70% Ethanol(aq) Extract, On-Line Post-Column Reaction of the SEC Fractions with DPPH and Determination of the Antioxidant Fractions
3.4. Characterization of the Compounds in the Isolated SEC Fractions, Identification of the Antioxidant Fraction Compounds by Orthogonal Methods, and their Antioxidant Activity over Time
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Extraction Solvents | ||||||||
---|---|---|---|---|---|---|---|---|
Water | Methanol | Acetone | Ethanol | Ethyl Acetate | ||||
100% | 80% (aq) | 100% | 70% (aq) | 100% | 70% (aq) | 90% (aq) | ||
Extraction yield (w/w %) | 25.8 | 38.1 | 37.2 | 21.1 | 42.6 | 29.3 | 44.3 | 14.9 |
IC50 (µg mL−1) | 3.561 | 3.715 | 3.469 | 2.632 | 3.350 | 2.893 | 3.503 | 2.786 |
LogIC50 | 0.552 | 0.570 | 0.540 | 0.420 | 0.525 | 0.461 | 0.544 | 0.445 |
LogIC50 std. error | 0.016 | 0.014 | 0.022 | 0.018 | 0.017 | 0.016 | 0.014 | 0.020 |
Hillslope | 1.607 | 1.884 | 1.669 | 1.911 | 1.665 | 1.924 | 1.789 | 1.756 |
Hillslope std. error | 0.083 | 0.105 | 0.125 | 0.136 | 0.097 | 0.123 | 0.093 | 0.124 |
0 h | 2 h | 4 h | 6 h | 8 h | 24 h | 50 h | 7 d | 14 d | |
---|---|---|---|---|---|---|---|---|---|
IC50 AA (µM) | 17.6853.1 | 30.524 | 37.662 | 45.846 | 56.612 | ~96.886 | 164.933 | ~219.382 | 356.495 |
IC50 AA (µg mL−1) | 15 | 5.376 | 6.633 | 8.075 | 9.971 | ~17.064 | 29.049 | ~38.637 | 62.787 |
LogIC50 (µM) | 1.248 | 1.485 | 1.576 | 1.661 | 1.753 | ~1.986 | 2.217 | ~2.341 | 2.552 |
LogIC50 std. error | 0.011 | 0.005 | 0.003 | 0.006 | 0.006 | ~1.293 | 0.020 | ~33.874 | 0.015 |
Hillslope | 2.606 | 5.344 | 6.492 | 6.060 | 5.673 | ~17.640 | 7.444 | ~16.268 | 9.400 |
Hillslope std. error | 0.149 | 0.304 | 0.254 | 0.566 | 0.383 | ~1659.493 | 0.771 | ~9712.611 | 0.938 |
IC50 JKRB (µg mL−1) | 3.503 | 3.684 | 3.662 | 3.876 | 3.947 | 3.530 | 3.759 | 3.731 | 3.325 |
LogIC50 | 0.544 | 0.566 | 0.564 | 0.588 | 0.596 | 0.548 | 0.575 | 0.572 | 0.522 |
LogIC50 std. error | 0.014 | 0.013 | 0.015 | 0.017 | 0.021 | 0.016 | 0.011 | 0.014 | 0.024 |
Hillslope | 1.789 | 1.815 | 1.858 | 1.796 | 1.736 | 2.044 | 1.933 | 1.737 | 1.531 |
Hillslope std. error | 0.093 | 0.086 | 0.106 | 0.117 | 0.128 | 0.140 | 0.085 | 0.088 | 0.118 |
FR | tR a [min] | MS [M-H]− | MS2 and MS3 b | Tentatively Identified Compounds |
---|---|---|---|---|
1 | 6.9 | 395 | [395]: 215 | c |
10.2, 9.4 | 1005 | [1005]: 713, 917, 961, 458 | derivative of emodin bianthrone-hexose-malonic acid [10] | |
2 | 7.3 | 521 | [521]: 359 | c |
7.3 | 581 | [581]: 521, 522, 544, 563, 499, 483, 417 | c | |
7.3 | 603 | [603]: 543, 521 | c | |
3 | 10.2 | 919 | [919]: 713, 671, 875, 458, 509, 416 | emodin bianthrone-hexose-(malonic acid)-hexose [10] |
10.2 | 941 | No data | c | |
11.4, 12.2 | 933 | [933]: 889, 458, 727 | methyl derivative of emodin bianthrone-hexose-(malonic acid)-hexose [10] | |
4 | 10.2 | 919 | [919]: 713, 671, 875, 458, 416, 509 | emodin bianthrone-hexose-(malonic acid)-hexose [10] |
10.2 | 1005 | [1005]: 917, 961, 875, 713, 458 | derivative of emodin bianthrone-hexose-malonic acid [10] | |
10.2, 12.0 | 1027 | [1027]: 939, 983, 735 (10.2 min) | c | |
[1027]: 389, 489, 533, 449, 744, 862, 939, 983, | c | |||
994 (12.0 min) | ||||
12.3 | 1009 | [1009]: 471, 389, 515, 921, 965 | c | |
12.3 | 987 | [987]: 449, 943 | c | |
12.3 | 449 | [449]: 245 | torachrysone 8-O-(6′-O-acetyl)-glucoside [67] | |
5 | 6.6, 10.6 | 473 | [473]: 455, 413 (6.6 min) | c |
[473]: 269 (10.6 min) | emodin-O-(acetyl)-hexoside [67] | |||
6.6, 10.6 | 605 | [605]: 587 | c | |
6.6, 10.6 | 665 | [665]: 647, 605, 589, 545, 501, 567 | c | |
10.6, 20.6 | 269 | [269]: 225, 269, 251, 241, 187 | emodin [67,74] | |
6 | 11.2 | 265 | No data | c |
11.2 | 297 | No data | c | |
11.2, 11.8 | 1005, 502, 458 | [1005]: 713, 917, 458 | derivative of emodin bianthrone-hexose-malonic acid [10] | |
11.2, 11.8 | 1027 | [1027]: 781, 863, 699, 715, 945, 617 | c | |
13.7 | 1019, 975 | [1019]: 691, 773, 855, 609, 527, 937 | derivative of bianthrone [10] | |
11.2 | 265 | No data | c | |
7 | 11.6 | 407 | [407]: 245 | torachrysone-8-O-glucoside/procyanidin degradation product [67] |
13.5 | 933 | [933]: 889, 685, 416 | methyl derivative of emodin bianthrone-hexose-(malonic acid)-hexose [10] | |
13.5 | 1019 | No data | c | |
8 | 5.6, 6.3 | 289 | [289]: 245, 205, 179, 203; | (−)-epicatechin (6.32 min) [67], (−)-epicatechin standard |
[289➔245] b: 203, 227, 161, 175, 187, 217, 245 | ||||
9.2, 8.3 | 431 | [431]: 227, 389 | resveratrol acetyl hexoside [67] | |
9.7, 9.0, 8.3 | 445 | [445]: 385 (9.7 min) | c | |
[445]: 281, 325, 369, 427, 263, 211 (9.0, 8.3 min) | c | |||
9.2, 8.3 | 475 | [475]: 431 | resveratrol malonyl hexoside [67] | |
9.2, 8.3 | 491 | [491]: 431 | c | |
9.2, 8.3 | 227 | [227]: 185, 183, 159, 157, 227, 209, 143 | resveratrol [67,52] | |
5.6, 6.3 | 289 | [289]: 245, 205, 179, 203; | (−)-epicatechin (6.32 min) [67], (−)-epicatechin standard | |
9 | 5.6 | 289 | [289]: 245, 205, 203, 179 | catechin [67] |
9.9 | 431 | [431]: 269 | emodin-O-hexoside [67] | |
9.9, 20.5 | 269 | [269]: 269, 225, 241, 251, 209, 271 | emodin [67,74] | |
9.9 | 385 | No data | c | |
10 | 7.1, 8.9 | 389 | [389]: 227 | polydatin (piceid)/resveratroloside [67] |
7.1, 8.9 | 425d | [425]: 389 | polydatin (piceid) (dihydrate)/resveratroloside (dihydrate) [67] | |
7.1 | 449d | [449]: 389, 227 | resveratrol acetyl hexoside (hydrate) [67] | |
7.1, 8.9 | 227 | [227]: 185, 183, 159, 157, 209, 143, 165 | resveratrol [67] | |
10.8 | 473 | [473]: 269, 311 | emodin-O-(acetyl)-hexoside [67] | |
10.8 | 517 | [517]: 473, 431 | emodin-O-(6′-O-malonyl)-hexoside [67] | |
11 | 6.6, 8.3 | 405 | [405]: 243 | piceatannol-3-O-glucoside [10] |
6.6, 8.3 | 243 | [243]: 225, 201, 199, 175, 215, 159 | piceatannol [75] | |
12 | 7.9, 9.1 | 389 | [389]: 227 | polydatin (piceid)/resveratroloside [67] |
7.9, 9.1 | 227 | [227]: 185, 183, 209, 159, 157, 165, 143 | resveratrol [67] | |
7.9, 9.1 | 425 d | [425]: 389, 227 | polydatin (piceid) (dihydrate)/resveratroloside (dihydrate) [67] | |
13 | 11.6 | 431 | [431]: 269, 311, 413 | emodin-O-hexoside [67] |
11.6 | 269 | [269]: 225, 269, 241, 251 | emodin [67,74] | |
4.9 | 565 | No data | c | |
14 | 7.2, 9.5 | 245 | [245]: 230 (7.2 min) | c [67] |
[245]: 229 (230) (9.5 min) | c [67] | |||
7.2, 9.5 | 325 d | [325]: 245 (7.2 min) | catechin dihydrate/unknown [67] | |
7.2, 9.5 | 245 | [325]: 244 (245), 203, 283 (9.5 min) | catechin dihydrate/unknown [67] |
0 h | 2 h | 4 h | 6 h | 8 h | 24 h | 50 h | 7 d | 14 d | |
---|---|---|---|---|---|---|---|---|---|
IC50 (µM) | 6.298 | 4.967 | 4.738 | 5.539 | 6.393 | 4.949 | 5.129 | 6.280 | 4.190 |
IC50 (µg mL−1) | 1.828 | 1.442 | 1.375 | 1.608 | 1.856 | 1.436 | 1.489 | 1.823 | 1.216 |
LogIC50 | 0.799 | 0.696 | 0.676 | 0.744 | 0.806 | 0.695 | 0.710 | 0.798 | 0.622 |
LogIC50 std. error | 0.039 | 0.040 | 0.047 | 0.045 | 0.043 | 0.044 | 0.041 | 0.052 | 0.039 |
Hillslope | 1.690 | 1.427 | 1.282 | 1.441 | 1.669 | 1.315 | 1.367 | 1.375 | 1.538 |
Hillslope std. error | 0.176 | 0.110 | 0.106 | 0.134 | 0.188 | 0.107 | 0.109 | 0.153 | 0.112 |
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Jug, U.; Naumoska, K.; Vovk, I. (−)-Epicatechin—An Important Contributor to the Antioxidant Activity of Japanese Knotweed Rhizome Bark Extract as Determined by Antioxidant Activity-Guided Fractionation. Antioxidants 2021, 10, 133. https://doi.org/10.3390/antiox10010133
Jug U, Naumoska K, Vovk I. (−)-Epicatechin—An Important Contributor to the Antioxidant Activity of Japanese Knotweed Rhizome Bark Extract as Determined by Antioxidant Activity-Guided Fractionation. Antioxidants. 2021; 10(1):133. https://doi.org/10.3390/antiox10010133
Chicago/Turabian StyleJug, Urška, Katerina Naumoska, and Irena Vovk. 2021. "(−)-Epicatechin—An Important Contributor to the Antioxidant Activity of Japanese Knotweed Rhizome Bark Extract as Determined by Antioxidant Activity-Guided Fractionation" Antioxidants 10, no. 1: 133. https://doi.org/10.3390/antiox10010133