Phenological Variations in the Content of Polyphenols and Triterpenoids in Epilobium angustifolium Herb Originating from Ukraine
Abstract
:1. Introduction
2. Results and Discussion
2.1. Variation in the Total Content of Phenolic Compounds
2.2. HPLC Metabolite Profiling
2.3. The Quantification of Core Metabolites
2.3.1. Phenolic Acids
2.3.2. Flavonoids
2.3.3. Tannins
2.3.4. Triterpenoids
2.4. Validation of the HPLC Method
2.5. Chemical Antioxidant Profile
2.6. Effects of the Flowering Phase on the Content of Metabolites
2.6.1. Quantitative Dynamics of Polyphenols
2.6.2. Quantitative Dynamics of Triterpenoids
3. Discussion
4. Materials and Methods
4.1. Plant Collection and Authentication
4.2. Chemicals and Solvents
4.3. Preparation of Extracts
4.4. Standard Solutions
4.5. Determination of Total Phenol Content
4.6. HPLC Chromatographic Analysis
4.7. Validation of the Analytical Method
4.8. Antioxidant Profile
4.8.1. ABTS Radical Scavenging Assay
4.8.2. FRAP Radical Scavenging Effects Assay
4.9. Statistical Analyses
5. Conclusions
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
Appendix A
Metabolite | Factor | Sum of Squares | df | Mean Square | F | p |
---|---|---|---|---|---|---|
Gallic acid | Plant part | 0.0544 | 1 | 0.0544 | 72.60 | <0.001 |
Phase | 0.0129 | 2 | 0.0064 | 8.58 | 0.005 | |
Interaction | 0.1303 | 2 | 0.0065 | 86.87 | <0.001 | |
Within | 0.0090 | 12 | 0.0001 | |||
Total | 0.0266 | 17 | ||||
Neochlorogenic acid | Plant part | 0.0660 | 1 | 0.0660 | 56.04 | <0.001 |
Phase | 1.3073 | 2 | 0.6536 | 555.00 | <0.001 | |
Interaction | 2.7751 | 2 | 1.3876 | 1178.00 | <0.001 | |
Within | 0.0141 | 12 | 0.0012 | |||
Total | 4.1626 | 17 | ||||
Oenothein B | Plant part | 831.95 | 1 | 831.95 | 11,330.00 | <0.001 |
Phase | 1258.79 | 2 | 629.39 | 8571.00 | <0.001 | |
Interaction | 1426.10 | 2 | 713.05 | 9710.00 | <0.001 | |
Within | 0.88 | 12 | 0.07 | |||
Total | 3517.72 | 17 | ||||
Oenothein A | Plant part | 9.6478 | 1 | 9.6478 | 3177.00 | <0.001 |
Phase | 50.7050 | 2 | 25.3525 | 8348.00 | <0.001 | |
Interaction | 61.8870 | 2 | 30.9435 | 10,190.00 | <0.001 | |
Within | 0.0364 | 12 | 0.0030 | |||
Total | 122.276 | 17 | ||||
Chlorogenic acid | Plant part | 0.5940 | 1 | 0.5940 | 136.20 | <0.001 |
Phase | 2.4310 | 2 | 1.2155 | 278.70 | <0.001 | |
Interaction | 2.2987 | 2 | 1.1493 | 263.50 | <0.001 | |
Within | 0.0523 | 12 | 0.0044 | |||
Total | 5.3761 | 17 | ||||
Ellagic acid | Plant part | 0.1166 | 1 | 0.1166 | 44.44 | <0.001 |
Phase | 0.0388 | 2 | 0.0194 | 7.40 | 0.008 | |
Interaction | 0.0393 | 2 | 0.0197 | 7.50 | 0.007 | |
Within | 0.0315 | 12 | 0.0026 | |||
Total | 0.2263 | 17 | ||||
Rutin | Plant part | 0.0390 | 1 | 0.0390 | 21.81 | <0.001 |
Phase | 10.0197 | 2 | 5.0098 | 2800.00 | <0.001 | |
Interaction | 0.8145 | 2 | 0.4072 | 227.60 | <0.001 | |
Within | 0.0215 | 12 | 0.0018 | |||
Total | 10.8947 | 17 | ||||
Hyperoside | Plant part | 0.1262 | 1 | 0.1262 | 99.06 | <0.001 |
Phase | 6.4952 | 2 | 3.2476 | 2550.00 | <0.001 | |
Interaction | 0.6669 | 2 | 0.3335 | 261.80 | <0.001 | |
Within | 0.0153 | 12 | 0.0013 | |||
Total | 7.3035 | 17 | ||||
Isoquercitrin | Plant part | 3.7174 | 1 | 3.7174 | 483.10 | <0.001 |
Phase | 46.9873 | 2 | 23.4937 | 3053.00 | <0.001 | |
Interaction | 39.1820 | 2 | 19.5910 | 2546.00 | <0.001 | |
Within | 0.0923 | 12 | 0.0077 | |||
Total | 89.9790 | 17 | ||||
Quercitrin | Plant part | 10.3983 | 1 | 10.3983 | 5658.00 | <0.001 |
Phase | 11.5140 | 2 | 5.7570 | 3132.00 | <0.001 | |
Interaction | 5.2254 | 2 | 2.6127 | 1422.00 | <0.001 | |
Within | 0.0220 | 12 | 0.0018 | |||
Total | 27.1597 | 17 | ||||
Quercetin | Plant part | 0.0000 | 1 | 0.0000 | 0.9134 | |
Phase | 0.0057 | 2 | 0.0028 | <0.001 | ||
Interaction | 0.0026 | 2 | 0.0013 | <0.001 | ||
Within | 0.0008 | 12 | 0.0007 | |||
Total | 0.0091 | 17 | ||||
Afzelin | Plant part | 49.6008 | 1 | 49.6008 | 54,770.00 | <0.001 |
Phase | 25.2428 | 2 | 12.6214 | 13,940.00 | <0.001 | |
Interaction | 25.7776 | 2 | 12.8888 | 14,230.00 | <0.001 | |
Within | 0.0109 | 12 | 0.0009 | |||
Total | 100.6320 | 17 | ||||
Guaijaverin | Plant part | 0.2594 | 1 | 0.2594 | 170.20 | <0.001 |
Phase | 5.1129 | 2 | 2.5564 | 1677.00 | <0.001 | |
Interaction | 0.9601 | 2 | 0.4800 | 314.90 | <0.001 | |
Within | 0.0183 | 12 | 0.0015 | |||
Total | 6.3507 | 17 | ||||
All phenolic compounds | Plant part | 1503.35 | 1 | 1503.35 | 25,270.00 | <0.001 |
Phase | 4119.62 | 2 | 2059.81 | 34,630.00 | <0.001 | |
Interaction | 2452.70 | 2 | 1226.35 | 20,610.00 | <0.001 | |
Within | 0.7139 | 12 | 0.0595 | |||
Total | 8076.38 | 17 |
Metabolite | Factor | Sum of Squares | df | Mean Square | F | p |
---|---|---|---|---|---|---|
Maslinic acid | Plant part | 0.0004 | 1 | 0.0004 | 0.8889 | 0.3644 |
Phase | 0.2103 | 2 | 0.1051 | 262.80 | <0.001 | |
Interaction | 0.0854 | 2 | 0.0427 | 106.80 | <0.001 | |
Within | 0.0048 | 12 | 0.0004 | |||
Total | 0.3008 | 17 | ||||
Corosolic acid | Plant part | 0.6013 | 1 | 0.6013 | 339.30 | <0.001 |
Phase | 6.4816 | 2 | 3.2408 | 1829.00 | <0.001 | |
Interaction | 1.0422 | 2 | 0.5211 | 294.00 | <0.001 | |
Within | 0.0213 | 12 | 0.0018 | |||
Total | 8.1464 | 17 | ||||
Oleanolic acid | Plant part | 0.0280 | 1 | 0.0280 | 42.36 | <0.001 |
Phase | 0.5697 | 2 | 0.2849 | 430.90 | <0.001 | |
Interaction | 0.1934 | 2 | 0.0967 | 146.30 | <0.001 | |
Within | 0.0079 | 12 | 0.0007 | |||
Total | 0.7990 | 17 | ||||
Ursolic acid | Plant part | 12.8863 | 1 | 12.8863 | 27,950.00 | <0.001 |
Phase | 0.6752 | 2 | 0.3376 | 732.20 | <0.001 | |
Interaction | 1.5075 | 2 | 0.7538 | 1635.00 | <0.001 | |
Within | 0.0055 | 12 | 0.0005 | |||
Total | 15.0746 | 17 | ||||
Betulin | Plant part | 0.0533 | 1 | 0.0533 | 96.04 | <0.001 |
Phase | 0.0588 | 2 | 0.0294 | 52.92 | <0.001 | |
Interaction | 0.0782 | 2 | 0.0391 | 70.36 | <0.001 | |
Within | 0.0067 | 12 | 0.0005 | |||
Total | 0.1970 | 17 | ||||
Erythrodiol | Plant part | 0.0047 | 1 | 0.0047 | 2.59 | 0.1337 |
Phase | 0.0053 | 2 | 0.0027 | 1.48 | 0.2664 | |
Interaction | 0.0053 | 2 | 0.0027 | 1.48 | 0.2664 | |
Within | 0.0217 | 12 | 0.0018 | |||
Total | 0.0370 | 17 | ||||
Uvaol | Plant part | 0.0002 | 1 | 0.0002 | 9.24 | 0.0102 |
Phase | 0.0004 | 2 | 0.0002 | 9.24 | 0.0037 | |
Interaction | 0.0004 | 2 | 0.0002 | 9.24 | 0.0037 | |
Within | 0.0002 | 12 | 0.0000 | |||
Total | 0.0011 | 17 | ||||
All triterpenoids | Plant part | 19.0550 | 1 | 19.0550 | 3076.00 | <0.001 |
Phase | 13.6317 | 2 | 6.8158 | 1100.00 | <0.001 | |
Interaction | 0.0261 | 2 | 0.0131 | 2.11 | 0.1639 | |
Within | 0.0743 | 12 | 0.0062 | |||
Total | 32.7872 | 17 |
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Indicator | Early Flowering | Mass Flowering | Late Flowering | ||||
---|---|---|---|---|---|---|---|
Flowers | Leaves | Flowers | Leaves | Rhizomes | Flowers | Leaves | |
Total amount of polyphenols, mg GA/g dw | 1.13 ± 0.02 | 1.29 ± 0.02 | 1.19 ±0.02 | 1.54 ± 0.03 | 0.56 ± 0.01 | 1.14 ± 0.02 | 1.17 ± 0.02 |
ABTS radical scavenging effects, μg TE/g dw | 8744.44 ± 153.20 | 9755.56 ± 171.15 | 8750.44 ± 153.85 | 8655.56 ± 152.18 | 2577.78 ± 45.32 | 8742.41 ± 153.71 | 9865.10 ± 177.34 |
Ferric reducing antioxidant power, mg FE(II)/g dw | 2287.50 ± 40.22 | 11,677.51 ± 205.32 | 3352.50 ± 58.95 | 9097.50 ± 159.96 | 2552.50 ± 44.87 | 3052.52 ± 53.67 | 3532.51 ± 62.11 |
RT | Metabolite | Early Flowering | Mass Flowering | Late Flowering | ||||
---|---|---|---|---|---|---|---|---|
Raw Material | Flowers | Leaves | Flowers | Leaves | Rhizomes | Flowers | Leaves | |
Polyphenols | ||||||||
6.06 | Gallic acid | 0.60 ± 0.01 | 0.51 ± 0.01 | 0.77 ± 0.01 | 0.41 ± 0.01 | 0.14 ± 0.01 | 0.57 ± 0.02 | 0.64 ± 0.01 |
9.53 | Neochlorogenic acid | 0.73 ± 0.01 | 1.35 ± 0.02 | 1.54 ± 0.03 | 0.54 ± 0.01 | 0.01 ± 0.00 | 1.23 ± 0.03 | 1.99 ± 0.04 |
10.68 | Oenothein B | 39.70 ± 0.70 | 24.90 ± 0.44 | 50.26 ± 0.88 | 15.45 ± 0.27 | 1.95 ± 0.03 | 45.95 ± 0.81 | 54.62 ± 0.96 |
11.68 | Chlorogenic acid | 0.91 ± 0.02 | 1.61 ± 0.03 | 1.77 ± 0.03 | 1.10 ± 0.02 | 0.01 ± 0.00 | 1.55 ± 0.03 | 2.60 ± 0.05 |
13.04 | Oenothein A | 3.96 ± 0.07 | 4.40 ± 0.08 | 8.44 ± 0.15 | 1.85 ± 0.03 | 0.13 ± 0.01 | 7.26 ± 0.13 | 9.00 ± 0.16 |
22.72 | Ellagic acid | 0.41 ± 0.01 | 0.27 ± 0.01 | 0.51 ± 0.02 | 0.23 ± 0.01 | 0.17 ± 0.02 | 0.52 ± 0.02 | 0.41 ± 0.01 |
22.73 | Rutin | 0.18 ± 0.00 | 0.01 ± 0.00 | 1.19 ± 0.03 | 0.90 ± 0.02 | - | 1.56 ± 0.03 | 2.26 ± 0.04 |
23.65 | Hyperoside | 0.16 ± 0.00 | 0.29 ± 0.01 | 1.05 ± 0.02 | 0.80 ± 0.01 | - | 1.38 ± 0.02 | 2.00 ± 0.04 |
24.90 | Isoquercitrin | 4.77 ± 0.08 | 8.08 ± 0.14 | 7.98 ± 1.14 | 4.69 ± 0.08 | 0.05 ± 0.00 | 8.41 ± 0.15 | 11.18 ± 0.20 |
31.11 | Quercitrin | 2.75 ± 0.05 | 0.53 ± 0.01 | 0.72 ± 0.03 | - | - | 2.92 ± 0.05 | 0.56 ± 0.01 |
31.13 | Quercetin | 0.03 ± 0.00 | 0.04 ± 0.00 | 0.05 ± 0.01 | 0.02 ± 0.01 | - | 0.06 ± 0.00 | 0.08 ± 0.01 |
37.74 | Afzelin | 3.24 ± 0.06 | 0.41 ± 0.01 | 0.66 ± 0.02 | - | - | 6.47 ± 0.12 | - |
27.82 | Guaijaverin | - | 0.50 ± 0.02 | 1.63 ± 0.03 | 1.24 ± 0.02 | - | 0.99 ± 0.02 | 1.58 ± 0.03 |
Total phenolic acid content | 0.66 ± 0.01 | 0.94 ± 0.03 | 1.15 ± 0.02 | 0.57 ± 0.01 | 0.08 ± 0.00 | 0.97 ± 0.03 | 1.41 ± 0.03 | |
Total tannin content | 21.83 ± 0.40 | 14.65 ± 0.26 | 29.35 ± 0.51 | 8.65 ± 0.15 | 1.04 ± 0.02 | 26.61 ± 0.47 | 31.81 ± 0.56 | |
Total flavonoid content | 1.86 ± 0.03 | 1.41 ± 0.02 | 1.90 ± 0.03 | 1.53 ± 0.03 | 0.05 ± 0.01 | 3.11 ± 0.06 | 2.94 ± 0.05 | |
Total polyphenol content | 57.44 ± 1.01 | 42.90 ± 0.75 | 75.85 ± 1.33 | 27.24 ± 0.48 | 2.45 ± 0.04 | 78.87 ± 1.39 | 86.92 ± 1.53 | |
Triterpenoids | ||||||||
6.278 | Maslinic acid | 0.50 ± 0.01 | 0.26 ± 0.01 | 0.13± 0.00 | 0.17 ± 0.01 | 0.10 ± 0.00 | 0.06 ± 0.00 | 0.21 ± 0.01 |
6.790 | Corosolic acid | 1.05 ± 0.02 | 0.81 ± 0.01 | 1.32 ± 0.02 | 2.23 ± 0.04 | 0.22 ± 0.01 | 0.12 ± 0.01 | 0.53 ± 0.01 |
12.06 | Oleanolic acid | 0.61 ± 0.01 | 0.54 ± 0.01 | 0.13 ± 0.00 | 0.50 ± 0.01 | 0.51 ± 0.01 | 0.19 ± 0.01 | 0.10 ± 0.00 |
12.69 | Ursolic acid | 1.08 ± 0.02 | 3.51 ± 0.06 | 2.20 ± 0.04 | 3.20 ± 0.06 | 0.11 ± 0.00 | 1.46 ± 0.03 | 3.12 ± 0.05 |
13.75 | Betulin | 0.51 ± 0.01 | 0.52 ± 0.02 | 0.53 ± 0.01 | 0.22 ± 0.01 | 0.08 ± 0.00 | 0.42 ± 0.01 | 0.38 ± 0.01 |
19.75 | Erythrodiol | - | 0.02 ± 0.00 | - | 0.02 ± 0.00 | - | - | - |
21.05 | Uvaol | - | - | - | 0.02 ± 0.00 | - | - | - |
Total content | 3.75 ± 0.07 | 5.66 ± 0.10 | 4.31 ± 0.08 | 6.36 ± 0.11 | 1.02 ± 0.02 | 2.25 ± 0.04 | 4.34 ± 0.08 |
Metabolite | RT, min | Coefficient of Determination R2 a | Equation | Linearity Range (µg/mL) | LOD (µg/mL) b | LOQ (µg/mL) c | Repeatability RT/Area (%) | Precision RT/Area (%) |
---|---|---|---|---|---|---|---|---|
Gallic acid | 6.10 | 0.99996 | y = 3.39 × 104x + 4.28 × 103 | 0.679–174.000 | 0.154 | 0.662 | 0.2/0.7 | 0.3/0.8 |
Neochlorogenic acid | 9.53 | 0.99982 | y = 5.50 × 104x − 2.29 × 103 | 0.195–25.000 | 0.102 | 0.307 | 0.3/0.7 | 0.4/0.8 |
Oenothein B | 10.66 | 0.99764 | y = 1.81 × 104x − 9.31 × 103 | 0.781–100.000 | 0.210 | 0.424 | 0.1/0.8 | 0.3/1.2 |
Chlorogenic acid | 11.95 | 0.99980 | y = 3.10 × 104x − 7.62 × 103 | 0.406–208.200 | 0.049 | 0.147 | 0.2/0.6 | 0.4/0.8 |
Ellagic acid | 22.48 | 0.99999 | y = 1.00 × 105x − 6.18 × 103 | 0.185–23.700 | 0.067 | 0.126 | 0.1/0.3 | 0.2/0.5 |
Rutin | 22.80 | 0.99993 | y = 1.85 × 104x − 5.68 × 103 | 2.456–78.600 | 0.200 | 0.731 | 0.3/0.7 | 0.4/0.8 |
Hyperoside | 23.62 | 0.99985 | y = 2.10 × 104x − 5.17 × 103 | 1.514–193.800 | 0.126 | 0.378 | 0.2/0.6 | 0.3/0.8 |
Isoquercitrin | 24.50 | 0.99978 | y = 2.18 × 104x − 7.31 × 103 | 1.462–187.200 | 0.278 | 0.772 | 0.2/0.7 | 0.4/0.9 |
Guaijaverin | 28.31 | 0.99838 | y = 1.21 × 104x + 5.33 × 103 | 1.562–100.000 | 0.260 | 0.781 | 0.1/1.0 | 0.3/1.2 |
Quercitrin | 30.90 | 0.99991 | y = 1.98 × 104x − 9.22 × 103 | 0.802–205.500 | 0.134 | 0.401 | 0.3/0.9 | 0.4/1.0 |
Afzelin | 37.95 | 0.99981 | y = 9.52 × 103x + 7.46 × 103 | 0.781–100.000 | 0.155 | 0.390 | 0.8/0.9 | 0.9/1.0 |
Quercetin | 43.65 | 0.99994 | y = 3.61 × 104x − 1.42 × 103 | 1.025–131.200 | 0.162 | 0.995 | 0.1/0.5 | 0.2/0.8 |
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Ivanauskas, L.; Uminska, K.; Gudžinskas, Z.; Heinrich, M.; Georgiyants, V.; Kozurak, A.; Mykhailenko, O. Phenological Variations in the Content of Polyphenols and Triterpenoids in Epilobium angustifolium Herb Originating from Ukraine. Plants 2024, 13, 120. https://doi.org/10.3390/plants13010120
Ivanauskas L, Uminska K, Gudžinskas Z, Heinrich M, Georgiyants V, Kozurak A, Mykhailenko O. Phenological Variations in the Content of Polyphenols and Triterpenoids in Epilobium angustifolium Herb Originating from Ukraine. Plants. 2024; 13(1):120. https://doi.org/10.3390/plants13010120
Chicago/Turabian StyleIvanauskas, Liudas, Kateryna Uminska, Zigmantas Gudžinskas, Michael Heinrich, Victoriya Georgiyants, Alla Kozurak, and Olha Mykhailenko. 2024. "Phenological Variations in the Content of Polyphenols and Triterpenoids in Epilobium angustifolium Herb Originating from Ukraine" Plants 13, no. 1: 120. https://doi.org/10.3390/plants13010120