Superior Valorisation of Juglans regia L. Leaves of Different Maturity through the Isolation of Bioactive Compounds
Abstract
:1. Introduction
2. Results and Discussion
2.1. Obtaining and Characterization of Juglans regia L. Leaves Extracts
2.1.1. Processing of Plant Material
2.1.2. Establishing the Optimal Extraction Parameters
The Influence of the Extraction Time
The Influence of the Extraction Solvent and Processing Method
The Obtaining of Walnut Leaf Extracts (YGL, GL, MGL, YL)—The Influence of the Extraction Solvent
2.2. Phytochemical Characteristics of Walnut Leaves Extracts
Identification of Phytochemical Compounds from Walnut Leaf Extracts
3. Materials and Methods
3.1. Plant Material
3.2. Chemicals
3.3. Preparation of Plant Extracts
3.4. Determination of Total Polyphenol Content (TPC) Using Spectrophotometric Method
3.5. Evaluation of Trolox Equivalent Antioxidant Capacity (TEAC) Using the Spectrophotometric Method
3.6. Fourier-Transform Ion-Cyclotron-Resonance High-Resolution Mass Spectrometry (FT-ICR-MS Method)
3.7. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Vegetable Material | Harvest Date | Moisture Content, % |
---|---|---|
young green leaves (YGL) | 15 May 2023 | 75.74 ± 0.03 |
green leaves (GL) | 26 June 2023 | 72.73 ± 0.02 |
mature green leaves (MGL) | 14 October 2022 | 55.17 ± 0.04 |
yellow leaves (YL) | 15 November 2022 | 64.64 ± 0.03 |
Method | Solvent | TPC * | TEAC ** |
---|---|---|---|
mg GAE/g DM | mM TE/g DM | ||
magnetic stirring (MS) | ethanol | 27.76 ± 0.59 a | 2.88 ± 0.02 a |
water | 76.08 ± 0.90 b | 5.60 ± 0.02 b | |
water:ethanol | 109.21 ± 0.34 c | 7.53 ± 0.02 c | |
ultrasounds assisted extraction (UA) | ethanol | 38.40 ± 0.59 a | 3.49 ± 0.02 a |
water | 82.58 ± 0.90 b | 5.49 ± 0.02 b | |
water:ethanol | 106.65 ± 0.34 c | 8.27 ± 0.02 c | |
maceration (M) | ethanol | 42.35 ± 0.90 a | 2.79 ± 0.02 a |
water | 93.04 ± 0.34 b | 5.28 ± 0.02 b | |
water:ethanol | 110.39 ± 0.90 c | 6.79 ± 0.02 c |
No. Exp. | Extraction Method | Solvent | TPC (mg GAE/g DM) | TPCpred (mg GAE/g DM) | ΔTPC (mg GAE/g DM) |
---|---|---|---|---|---|
1 | MS | ethanol | 27.75 | 30.91 | −3.16 |
2 | MS | water | 76.08 | 78.64 | −2.56 |
3 | MS | water:ethanol | 109.21 | 103.49 | 5.72 |
4 | UA | ethanol | 38.40 | 35.77 | 2.63 |
5 | UA | water | 82.58 | 83.50 | −0.92 |
6 | UA | water:ethanol | 106.65 | 108.36 | −1.71 |
7 | M | ethanol | 42.35 | 41.82 | 0.53 |
8 | M | water | 93.04 | 89.55 | 3.48 |
9 | M | water:ethanol | 110.39 | 114.40 | −4.01 |
RMSE | 3.134 | ||||
R2 | 0.990 | ||||
Adjusted R2 | 0.979 | ||||
Predicted R2 | 0.950 | ||||
Adequate Precision | 23.82 | ||||
F | 94.34 | ||||
p | 0.0003 |
No. Exp. | Extraction Method | Solvent | TEAC (mg TE/g DM) | TEACpred (mg TE/g DM) | ΔTEAC (mg TE/g DM) |
---|---|---|---|---|---|
1 | MS | ethanol | 2.88 | 3.04 | −0.1628 |
2 | MS | water | 5.60 | 5.44 | 0.1526 |
3 | MS | water:ethanol | 7.53 | 7.52 | 0.0102 |
4 | UA | ethanol | 3.49 | 3.46 | 0.0315 |
5 | UA | water | 5.49 | 5.86 | −0.3687 |
6 | UA | water:ethanol | 8.27 | 7.93 | 0.3373 |
7 | M | ethanol | 2.79 | 2.66 | 0.1313 |
8 | M | water | 5.28 | 5.06 | 0.2162 |
9 | M | water:ethanol | 6.79 | 7.13 | −0.3474 |
RMSE | 0.232 | ||||
R2 | 0.985 | ||||
Adjusted R2 | 0.969 | ||||
Predicted R2 | 0.922 | ||||
Adequate Precision | 20.30 | ||||
F | 63.89 | ||||
p | 0.0007 |
Type of Leaves | Solvent | TPC * | TEAC ** |
---|---|---|---|
mg GAE/g DM | mM TE/g DM | ||
YGL | ethanol | 1.32 ± 0.34 a | 0.03 ± 0.00 a |
water | 2.90 ± 0.59 ab | 0.04 ± 0.00 a | |
water:ethanol | 18.28 ± 0.59 b | 0.09 ± 0.00 a | |
GL | ethanol | 0.73 ± 0.34 a | 0.03 ± 0.00 a |
water | 3.49 ± 0.59 ab | 0.03 ± 0.00 a | |
water:ethanol | 16.90 ± 0.90 b | 0.08 ± 0.00 a | |
MGL | ethanol | 38.40 ± 0.59 c | 3.50 ± 0.02 b |
water | 82.58 ± 0.90 cd | 5.50 ± 0.02 b | |
water:ethanol | 106.65 ± 0.34 c | 8.27 ± 0.02 b | |
YL | ethanol | 62.66 ± 0.59 c | 4.74 ± 0.02 b |
water | 110.20 ± 0.34 cd | 7.76 ± 0.02 b | |
water:ethanol | 146.29 ± 0.90 c | 11.67 ± 0.02 b |
No. Exp. | Plant Maturity | Solvent | TPC0.5 (mg GAE/g DM) | TPCpred0.5 (mg GAE/g DM) | ΔTPC0.5 (mg GAE/g DM) |
---|---|---|---|---|---|
1 | YGL | ethanol | 12.10 | 12.04 | 0.0531 |
2 | YGL | water | 1.70 | 2.34 | −0.6326 |
3 | YGL | water:ethanol | 9.09 | 8.50 | 0.5912 |
4 | GL | ethanol | 4.28 | 4.25 | 0.0273 |
5 | GL | water | 7.92 | 8.34 | −0.4218 |
6 | GL | water:ethanol | 0.7297 | 0.4047 | 0.3250 |
7 | MGL | ethanol | 4.11 | 4.11 | 0.0023 |
8 | MGL | water | 1.15 | 0.5443 | 0.6052 |
9 | MGL | water:ethanol | 6.20 | 6.71 | −0.5084 |
10 | YL | ethanol | 10.33 | 10.41 | −0.0827 |
11 | YL | water | 10.50 | 10.13 | 0.3687 |
12 | YL | water:ethanol | 1.87 | 2.20 | −0.3273 |
RMSE | 0.398 | ||||
R2 | 0.9895 | ||||
Adjusted R2 | 0.9808 | ||||
Predicted R2 | 0.9581 | ||||
Adequate Precision | 29.15 | ||||
F | 113.29 | ||||
p | <0.0001 |
No. Exp. | Plant Maturity | Solvent | log(TEAC) (mg TE/g DM) | log(TEACpred) (mg TE/g DM) | log(ΔTEAC) (mg TE/g DM) |
---|---|---|---|---|---|
1 | YGL | ethanol | 1.07 | 1.12 | −0.0556 |
2 | YGL | water | −1.39 | −1.37 | −0.0168 |
3 | YGL | water:ethanol | 0.7399 | 0.6910 | 0.0489 |
4 | GL | ethanol | −1.05 | −1.08 | 0.0351 |
5 | GL | water | 0.6760 | 0.6750 | 0.0010 |
6 | GL | water:ethanol | −1.60 | −1.60 | 0.0051 |
7 | MGL | ethanol | −1.07 | −1.15 | 0.0817 |
8 | MGL | water | −1.55 | −1.53 | −0.0183 |
9 | MGL | water:ethanol | 0.5433 | 0.5311 | 0.0122 |
10 | YL | ethanol | 0.9176 | 0.9787 | −0.0612 |
11 | YL | water | 0.8896 | 0.8350 | 0.0546 |
12 | YL | water:ethanol | −1.53 | −1.44 | −0.0867 |
RMSE | 0.049 | ||||
R2 | 0.998 | ||||
Adjusted R2 | 0.966 | ||||
Predicted R2 | 0.922 | ||||
Adequate Precision | 55.98 | ||||
F | 615.14 | ||||
p | <0.0001 |
Compound | Theoretical m/z (ESI+) | Type of Extract | ||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
MGL * | YGL ** | GL *** | MGL * | YL **** | ||||||||||||||||||||||||
Extraction Method | ||||||||||||||||||||||||||||
MS (m) | MS | UA | M | UA | ||||||||||||||||||||||||
Extraction Time (min) | Extraction Solvent (60 min) | Extraction Solvent (60 min) | ||||||||||||||||||||||||||
1 | 10 | 20 | 30 | 45 | 60 | e | w | m | e | w | m | e | w | m | e | w | m | e | w | m | e | w | m | e | w | m | ||
Sample Number | ||||||||||||||||||||||||||||
1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 6 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 9 | 10 | 11 | 21 | 22 | 23 | ||
Caffeic acid | 181.049535 | − | + | + | + | + | + | − | + | + | − | + | + | − | + | + | − | − | + | − | − | + | − | + | + | − | + | + |
Caftaric acid+Na | 335.037353 | + | + | + | + | + | + | − | + | + | − | + | + | − | + | + | − | + | − | − | + | − | − | + | + | − | + | − |
Chlorogenic acid | 355.102359 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + |
Ellagic acid | 303.013544 | − | − | − | − | − | − | − | − | − | − | − | − | − | − | − | − | + | − | − | + | − | − | − | − | − | − | − |
Ferulic acid | 196.065185 | + | + | + | + | + | + | − | + | + | − | + | + | − | + | + | − | − | − | − | + | − | − | + | + | − | + | + |
Juglone | 175.038971 | + | + | + | + | + | + | − | + | + | − | + | + | − | + | + | − | − | + | − | − | + | − | + | + | − | + | + |
p-coumaric acid | 165.054621 | + | + | + | + | + | + | − | + | + | − | + | + | − | + | + | − | − | − | − | − | − | − | + | + | − | + | + |
Sinapate | 225.075750 | + | + | + | + | + | + | − | + | + | − | + | + | − | + | + | − | − | − | − | − | − | − | + | + | − | + | + |
3-p-coumaroylquinic acid | 339.107444 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + |
Quercetin 3-o-arabinoside | 435.092188 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + |
Quercetin 3-rhamnoside | 449.107838 | + | + | + | + | + | + | − | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + |
Quercetin 3-o-pentoside | 567.134447 | − | − | − | − | − | − | − | + | − | − | + | − | − | − | − | − | − | − | − | − | − | − | + | − | − | + | − |
Quercetin | 303.049929 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + |
Myricetin | 319.044844 | + | + | + | + | + | + | − | + | + | − | + | + | − | + | + | − | − | + | − | − | + | − | + | + | − | + | + |
Kaempferol | 287.055014 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + |
Kaempferol 3-o-arabinoside | 419.097273 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + |
Kaempferol-3-o-rhamnoside | 433.112923 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + |
Isokaempferide | 301.070665 | + | + | + | + | + | + | − | + | + | − | + | + | − | + | + | − | − | + | − | + | + | − | + | + | − | + | + |
Catechin hydrate | 309.096879 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + |
Hyperoside | 465.102753 | + | + | + | + | + | + | − | + | + | − | + | + | − | + | + | + | + | − | − | + | + | − | + | + | − | + | + |
Luteolin | 287.055014 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + |
Naringenin | 273.075750 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | − | − | + | − | + | + | + | + | + | + | + | + |
Hesperetin | 303.086812 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | − | − | + | − | − | + | + | + | + | − | + | + |
Catechin | 291.086315 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + |
Epigallocatechin | 307.081229 | − | − | + | + | + | + | − | + | + | − | + | + | − | + | + | − | − | − | − | − | − | − | + | + | + | + | + |
Epigallocatechin gallate | 443.097273 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + |
Fisetinidol | 275.091400 | + | + | + | + | + | + | − | + | + | − | + | + | − | + | + | − | − | − | − | + | − | − | + | + | − | + | + |
Guibourtinidol | 259.096485 | + | + | + | + | + | + | − | + | + | − | + | + | − | + | + | − | − | − | − | + | + | − | + | + | − | + | − |
Oleanic acid | 457.367622 | + | + | + | + | + | + | + | − | + | + | + | + | + | − | + | + | − | + | + | − | + | + | + | + | + | − | + |
Stigmasterol | 413.377793 | + | + | + | + | + | + | + | − | + | + | + | + | + | − | + | + | + | + | − | + | + | + | + | + | + | + | + |
Resveratrol | 229.085921 | + | + | + | + | + | + | − | − | + | − | − | − | − | − | − | + | − | + | − | − | − | − | − | − | − | + | − |
Myo-inositol | 181.070665 | − | + | + | + | + | + | − | + | + | − | + | − | − | + | − | − | + | + | − | + | + | − | + | − | − | − | − |
Taxifolin | 305.065579 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + |
Pelargonidin | 271.060100 | + | + | + | + | + | + | − | + | + | − | + | + | − | + | + | − | + | + | − | − | − | − | + | + | − | + | + |
Malvidin | 331.081229 | − | − | − | − | − | − | − | + | − | − | + | + | − | + | + | + | + | + | − | + | + | − | + | + | − | + | + |
Cyanidin-3-glucoside chloride | 485.084516 | + | + | + | + | + | + | − | − | + | − | − | − | − | − | − | − | − | − | − | − | − | − | − | − | − | − | − |
Quinic acid | 193.070665 | + | + | + | + | + | + | − | + | + | − | + | + | − | + | + | − | + | + | − | + | + | − | + | + | − | + | + |
Citric acid+Na | 215.016223 | + | − | − | − | − | + | − | + | + | − | + | − | − | − | − | − | − | − | − | − | + | − | + | − | − | − | − |
Azelaic acid | 189.112135 | − | − | − | − | − | − | − | − | − | − | − | − | − | − | − | − | + | − | − | − | − | − | − | − | − | − | − |
Asiatic acid | 489.357451 | + | + | + | + | + | + | + | + | + | + | + | + | + | + | + | − | + | + | + | + | + | + | + | + | + | + | + |
Total number of compounds | 33 | 34 | 35 | 35 | 35 | 36 | 17 | 34 | 36 | 18 | 36 | 33 | 18 | 32 | 33 | 18 | 23 | 27 | 15 | 26 | 28 | 18 | 36 | 33 | 18 | 34 | 31 | |
Sample number | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 6 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 9 | 10 | 11 | 21 | 22 | 23 |
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Tociu, M.; Manolache, F.; Bălănucă, B.; Moroșan, A.; Stan, R. Superior Valorisation of Juglans regia L. Leaves of Different Maturity through the Isolation of Bioactive Compounds. Molecules 2023, 28, 7328. https://doi.org/10.3390/molecules28217328
Tociu M, Manolache F, Bălănucă B, Moroșan A, Stan R. Superior Valorisation of Juglans regia L. Leaves of Different Maturity through the Isolation of Bioactive Compounds. Molecules. 2023; 28(21):7328. https://doi.org/10.3390/molecules28217328
Chicago/Turabian StyleTociu, Mihaela, Fulvia Manolache, Brîndușa Bălănucă, Alina Moroșan, and Raluca Stan. 2023. "Superior Valorisation of Juglans regia L. Leaves of Different Maturity through the Isolation of Bioactive Compounds" Molecules 28, no. 21: 7328. https://doi.org/10.3390/molecules28217328