The Potential Value of Debarking Water as a Source of Polyphenolic Compounds for the Specialty Chemicals Sector
Abstract
:1. Introduction
2. Results and Discussion
2.1. Identification of the Polyphenolic Compounds by HPLC-DAD-MS/MS
2.2. Polyphenolic Compounds in Debarking Water, Bark Press Water, and Bark Extracts
2.3. DPPH Tests
3. Materials and Methods
3.1. Materials and Instrumentation
3.2. Sample Collection
3.3. Sample Collection
3.4. LC-MS/MS Analysis
3.5. Radical Scavenging Activity Measured Using DPPH Assay
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Peak No. | Retention Time | Identity Compound | m/z | Detected Fragments | Fragments Found in Literature |
---|---|---|---|---|---|
1 | 2.0 | Quinic acid | 191.0555 | 173, 127, 111, 93, 87, 85 | 173, 127, 111, 85 |
2 | 4.9 | Protocatechuic acid | 153.0182 | 153, 109 | 153, 109 |
3 | 6.0 | Catechin | 289.0713 | 289, 245, 205, 203, 179, 125, 109 | 289, 271, 245 |
4 | 6.1 | Ferulic acid | 193.05 | 193, 178, 149, 134 | 178, 149, 134 |
5 | 7.8 | Dihydrorobinetin | 303.0506 | 303, 285 | 303, 285 |
6 | 9.0 | Quercitrin | 447.0927 | 301 | 300, 301, 271, 255, 151 |
7 | 9.4 | Spiraeoside | 463.0873 | 301 | 301 |
8 | 9.8 | Isorhamnetin rhamnoside | 461.1086 | 315 | 315 |
Peak No. | Retention Time | m/z | Detected Fragments | Possible Identity Compound |
---|---|---|---|---|
1a | 5.7 | 371.0970 | 325, 205, 163, 119, 45 | Oxomatairesinol |
2a | 6.3 | 443.1320 | 443, 113, 101, 89, 71, 59 | Unknown |
3a | 7.3 | 451.1248 | 406, 405, 243, 201, 199, 173, 159 | (Epi)catechin-O-glucoside |
4a | 7.3 | 441.0954 | 441, 405, 243, 201, 159, 113, 112, | (Epi)catechin monogallate |
5a | 7.5 | 525.1978 | 327, 179, 167, 161, 146, 134, 119, 89 | Isorhamnetin glucoside |
6a | 8.3 | 373.1506 | 373, 281, 161, 143, 101, 45 | (Iso)hdydroxymatairesinol |
7a | 8.5 | 647.1764 | 647, 605, 600, 485,435, 401, 361, 309, 241 | Piceatannol derivative |
8a | 8.8 | 171.0734 | 171, 145, 127, 103, 83 | Diethyl maleate |
Retention Time | Identity Compound | m/z | Detected Fragments | Fragments in Literature |
---|---|---|---|---|
4.8 | Syringaldehyde | 181.0499 | 181, 151 | 181, 166, 151 |
5.2 | Dihydroxyphenylacetic acid | 167.0342 | 123 | 123 |
6.7 | Vanillin | 151.0391 | 151, 136, 108, 107 | 151, 137, 136, 123, 108, 107 |
6.2 and 7.2 | Oxyresveratrol | 243.0652 | 225, 199, 157 | 225, 199, 157, 133, 115 |
7.8 | P-coumaric acid | 163.0395 | 163, 119 | 163, 119, 94 |
7.8 and 8.1 | Aromadendrin-rhamnoside | 433.1148 | 269, 179, 151 | 287, 269, 259, 180, 179, 151 |
9.2 | Isorhamnetin-O-hexoside | 477.1043 | 315 | 315 |
10.4 | Robinetin | 301.0359 | 301, 273, 245 | 301, 273, 245, 229, 135, 91 |
13.2 | Eugenol | 209.0808 | 163 | 163, 149, 147, 137 |
Compound (RT in min) | PC | PW | DC | DW |
---|---|---|---|---|
Quinic acid | 85,989 ± 1912 | 81,331 ± 2084 | 83,169 ± 2719 | |
Protocatechuic acid (isomer 1) | <LOQ | <LOQ | ||
Syringaldehyde | 6539 ± 581 | <LOQ | <LOQ | <LOQ |
Protocatechuic acid (isomer 2) | 16,204 ± 1184 | 23,408 ± 695 | <LOQ | 11,451 ± 1292 |
Catechin | 8461 ± 1419 | >LOQ | ||
Ferulic acid | 13,006 ± 523 | 15,998 ± 767 | 9151 ± 1304 | |
Vanillin | <LOQ | |||
Oxyresveratrol | <LOQ | |||
P-coumaric acid | 10,106 ± 2511 | <LOQ | ||
Isorhamnetin-O-hexoside | <LOQ | |||
Spiraeoside | <LOQ | |||
Eugenol | 6431 ± 727 | 9070 ± 247 | ||
Total polyphenol concentration (mg/mL) | 12.99 ± 0.22 | 15.55 ± 0.81 | 1.95 ± 0.02 | 4.76 ± 0.35 |
Compound | Bark Cold Water Extraction | Bark Ethanol/Water (1:1) Extraction | Bark Ethanol Extraction | Bark Hot Water Extraction | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
(RT in min) | 2 min | 5 min | 30 min | 2 min | 5 min | 30 min | 2 min | 5 min | 30 min | 2 min | 5 min | 30 min |
Quinic acid | 91,055 ± 5082 | 88,490 ± 4899 | 97,538 ± 5933 | 73,973 ± 4246 | 80,280 ± 1328 | 81,208 ± 2909 | 3734 ± 817 | 6093 ± 451 | 8290 ± 633 | 87,926 ± 2482 | 84,382 ± 4714 | 90,067 ± 570 |
Syringaldehyde | <LOQ | <LOQ | <LOQ | <LOQ | <LOQ | |||||||
Protocatechuic acid | 8274 ± 778 | 9894 ± 1117 | 11,650 ± 581 | 9432 ± 886 | 10,745 ± 214 | 10,132 ± 93 | 1011 ± 14 | 2090 ± 381 | 3696 ± 871 | 10,773 ± 361 | 11,477 ± 424 | 14,670 ± 1067 |
Dihydroxyphenylacetic acid | <LOQ | |||||||||||
Catechin | 17,701 ± 729 | 17,458 ± 1583 | 18,348 ± 1169 | 10,004 ± 670 | 13,353 ± 567 | 16,185 ± 105 | <LOQ | |||||
Ferulic acid | 7771 ± 857 | 7388 ± 416 | 9443 ± 220 | 7557 ± 261 | 6633 ± 871 | 7490 ± 85 | <LOQ | <LOQ | 7731 ± 80 | 8325 ± 763 | 8043 ± 57 | |
Aromadendrin-rhamnoside | <LOQ | |||||||||||
Dihydrorobinetin | 8214 ± 65 | 9153 ± 2554 | 16,081 ± 522 | 42,783 ± 4072 | 47,511 ± 3313 | 49,642 ± 894 | 20,044 ± 1785 | 27,636 ± 3964 | 44,938 ± 1006 | 10,325 ± 3840 | 14,068 ± 5642 | 14,914 ± 2224 |
Oxyresveratrol | <LOQ | 15,509 ± 2885 | 17,221 ± 3324 | |||||||||
Quercitrin | 3582 ± 911 | 3902 ± 784 | 5816 ± 419 | 15,565 ± 1036 | 16,300 ± 732 | 17,460 ± 296 | 5003 ± 834 | 6667 ± 323 | 9063 ± 596 | 4549 ± 299 | 5775 ± 192 | 7951 ± 94 |
Isorhamnetin-hexoside | <LOQ | <LOQ | <LOQ | |||||||||
Spiraeoside | <LOQ | 29,498 ± 1639 | 30,412 ± 4680 | 30,695 ± 1565 | 14,107 ± 2418 | 17,537 ± 695 | 22,268 ± 671 | <LOQ | ||||
Isorhamnetin-O-rhamnoside | <LOQ | < LOQ | 9333 ± 179 | 9493 ± 503 | <LOQ | 3243 ± 24 | 3873 ± 53 | 5688 ± 88 | ||||
Robinetin | 1089 ± 217 | 1404 ± 139 | 1528 ± 136 | |||||||||
Total polyphenol concentration (mg/mL) | 7.24 ± 1.11 | 7.07 ± 1.75 | 9.21 ± 0.55 | 15.86 ± 2.27 | 16.35 ± 1.62 | 16.74 ± 0.30 | 6.84 ± 0.41 | 9.39 ± 0.47 | 13.18 ± 2.03 | 7.54 ± 0.05 | 7.29 ± 0.01 | 9.41 ± 0.64 |
Sample | 0.2 µm Filtered Samples | 3000 Da Filtered Samples | ||
---|---|---|---|---|
EC50 (µg/mL) | mg GAE/g (Dry Mass) | EC50 (µg/mL) | mg GAE/g (Dry Mass) | |
CW2 | 154 ± 25 | 3.23 ± 0.97 | 560 ± 28 | 1.26 ± 0.06 |
CW5 | 203 ± 16 | 2.24 ± 0.16 | 920 ± 46 | 0.48 ± 0.02 |
CW30 | 213 ± 13 | 1.96 ± 0.22 | 971 ± 49 | 0.42 ± 0.02 |
CWE2 | 77 ± 24 | 6.90 ± 2.06 | 425 ± 21 | 1.02 ± 0.05 |
CWE5 | 105 ± 4 | 4.27 ± 1.70 | 450 ± 23 | 0.49 ± 0.02 |
CWE30 | 85 ± 16 | 4.54 ± 1.27 | 432 ± 22 | 0.51 ± 0.03 |
E2 | 317 ± 21 | 1.26 ± 0.05 | 332 ± 17 | 1.38 ± 0.07 |
E5 | 238 ± 81 | 1.31 ± 0.81 | 166 ± 8 | 2.26 ± 0.11 |
E30 | 161 ± 13 | 1.84 ± 0.99 | 153 ± 8 | 1.41 ± 0.07 |
HW2 | 108 ± 5 | 5.27 ± 0.90 | 584 ± 29 | 0.86 ± 0.04 |
HW5 | 113 ± 16 | 4.13 ± 0.23 | 901 ± 45 | 0.51 ± 0.03 |
HW30 | 167 ± 66 | 2.40 ± 0.62 | 1030 ± 52 | 0.34 ± 0.02 |
PC | 134 ± 1 | 4.02 ± 0.70 | 391 ± 20 | 1.73 ± 0.09 |
PW | 136 ± 5 | 3.53 ± 0.15 | 391 ± 20 | 1.04 ± 0.05 |
DC | 3333 ± 590 | 0.17 ± 0.04 | 3006 ± 150 | 0.18 ± 0.01 |
DW | 169 ± 18 | 1.62 ± 0.12 | 1340 ± 67 | 0.24 ± 0.01 |
Sample | Temperature | Time (min) | Solvent |
---|---|---|---|
CW2 | TR | 2 | Distilled water |
CW5 | TR | 5 | Distilled water |
CW30 | TR | 30 | Distilled water |
CWE2 | TR | 2 | Deionised water and ethanol (50:50) |
CWE5 | TR | 5 | Deionised water and ethanol (50:50) |
CWE30 | TR | 30 | Deionised water and ethanol (50:50) |
E2 | TR | 2 | Ethanol |
E5 | TR | 5 | Ethanol |
E30 | TR | 30 | Ethanol |
HW2 | 80 °C | 2 | Deionised water |
HW5 | 80 °C | 5 | Deionised water |
HW30 | 80 °C | 30 | Deionised water |
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Peeters, K.; Esakkimuthu, E.S.; Tavzes, Č.; Kramberger, K.; Miklavčič Višnjevec, A. The Potential Value of Debarking Water as a Source of Polyphenolic Compounds for the Specialty Chemicals Sector. Molecules 2023, 28, 542. https://doi.org/10.3390/molecules28020542
Peeters K, Esakkimuthu ES, Tavzes Č, Kramberger K, Miklavčič Višnjevec A. The Potential Value of Debarking Water as a Source of Polyphenolic Compounds for the Specialty Chemicals Sector. Molecules. 2023; 28(2):542. https://doi.org/10.3390/molecules28020542
Chicago/Turabian StylePeeters, Kelly, Esakkiammal Sudha Esakkimuthu, Črtomir Tavzes, Katja Kramberger, and Ana Miklavčič Višnjevec. 2023. "The Potential Value of Debarking Water as a Source of Polyphenolic Compounds for the Specialty Chemicals Sector" Molecules 28, no. 2: 542. https://doi.org/10.3390/molecules28020542