Recovery of Biologically Active Compounds from Stinging Nettle Leaves Part II: Processing of Exhausted Plant Material after Supercritical Fluid Extraction
Abstract
:1. Introduction
2. Material and Methods
2.1. Plant Material
2.2. Extraction Procedures
2.3. Total Phenolics and Flavonoids Contents
2.4. Polyphenolic Profile
2.5. Biological Activity
2.6. ANN Modeling
2.7. Statistical Analyses
3. Results and Discussion
3.1. Extraction Yield
3.2. Polyphenolic Profile and Composition of the Extracts
3.3. Biological Activity of Obtained Extracts
3.4. PCA Analysis
3.5. ANN Model
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Parameter | Extracts | |||||
---|---|---|---|---|---|---|
1 | 2 | 3 | 4 | 5 | 6 | |
Pressure (bar) | 100 | 100 | 200 | 200 | 300 | 300 |
Temperature (°C) | 40 | 60 | 40 | 60 | 40 | 60 |
Density (g/cm3) | 0.629 | 0.290 | 0.840 | 0.724 | 0.910 | 0.830 |
Separation parameters | ||||||
Pressure (bar) | 15 | 15 | 15 | 15 | 15 | 15 |
Temperature (°C) | 23 | 23 | 23 | 23 | 23 | 23 |
Sample | Yield (mg/mL) | Yield (g/100 g) |
---|---|---|
UAE | ||
UAE | 3.86 ± 0.06 b | 11.58 ± 0.09 |
UAE-1 | 3.06 ± 0.09 a | 9.18 ± 0.06 |
UAE-2 | 5.51 ± 0.07 c | 16.53 ± 0.10 |
UAE-3 | 6.09 ± 0.08 d | 18.27 ± 0.11 |
UAE-4 | 3.96 ± 0.04 b | 11.88 ± 0.08 |
UAE-5 | 8.40 ± 0.09 e | 25.20 ± 0.06 |
UAE-6 | 6.09 ± 0.03 d | 18.27 ± 0.11 |
MAE | ||
MAE | 10.27 ± 0.09 h | 30.81 ± 0.11 |
MAE-1 | 10.56 ± 0.10 i | 31.68 ± 0.12 |
MAE-2 | 10.79 ± 0.08 j | 32.37 ± 0.15 |
MAE-3 | 9.80 ± 0.06 g | 29.40 ± 0.10 |
MAE-4 | 9.65 ± 0.06 fg | 28.95 ± 0.09 |
MAE-5 | 10.74 ± 0.10 ij | 32.22 ± 0.09 |
MAE-6 | 9.58 ± 0.08 f | 28.74 ± 0.08 |
Sample | TPC (mg CAE/g SN) | TFC (mg CE/g SN) |
---|---|---|
UAE | ||
UAE | 133.41 ± 1.26 b | 3.31 ± 0.11 b |
UAE-1 | 110.80 ± 2.22 a | 2.86 ± 0.09 a |
UAE-2 | 185.35 ± 1.52 d | 5.18 ± 0.16 d |
UAE-3 | 194.52 ± 2.82 e | 5.33 ± 0.09 d |
UAE-4 | 149.29 ± 2.23 c | 3.60 ± 0.08 c |
UAE-5 | 289.23 ± 3.11 g | 8.41 ± 0.06 f |
UAE-6 | 219.57 ± 2.65 f | 6.33 ± 0.11 e |
MAE | ||
MAE | 371.92 ± 3.56 j | 10.92 ± 0.10 h |
MAE-1 | 395.14 ± 2.99 k | 12.27 ± 0.06 j |
MAE-2 | 428.14 ± 3.59 m | 12.36 ± 0.08 j |
MAE-3 | 347.46 ± 4.11 i | 10.77 ± 0.09 h |
MAE-4 | 337.69 ± 3.25 h | 10.25 ± 0.08 g |
MAE-5 | 404.50 ± 3.77 l | 11.32 ± 0.07 i |
MAE-6 | 341.37 ± 2.85 hi | 10.96 ± 0.09 h |
Compound | Content (mg/L) | ||||||
---|---|---|---|---|---|---|---|
UAE | UAE-1 | UAE-2 | UAE-3 | UAE-4 | UAE-5 | UAE-6 | |
Protocatechuic acid | 4.50 ± 0.20 c | 2.32 ± 0.02 b | 2.26 ± 0.04 b | ND * | ND | 1.20 ± 0.06 a | ND |
p-Hydroxybenzoic acid | 1.11 ± 0.06 a | 1.73 ± 0.01 d | 1.64 ± 0.06 c | 1.88 ± 0.09 e | 1.84 ± 0.02 e | 1.34 ± 0.05 b | 1.81 ± 0.03 e |
Caffeic acid | 20.85 ± 0.52 g | 9.88 ± 0.03 e | 10.70 ±0.09 f | 4.04 ± 0.10 a | 6.67 ± 0.09 c | 4.84 ± 0.05 b | 6.91 ± 0.10 d |
Vanillic acid | 1.05 ± 0.01 a | 1.96 ± 0.02 d | 1.74 ± 0.01 c | 1.95 ± 0.03 d | 2.05 ± 0.03 e | 1.33 ± 0.03 b | 2.01 ± 0.08 e |
Aesculin | 1.96 ± 0.06 e | 0.69 ± 0.01 a | 0.88 ± 0.01 b | 0.96 ± 0.06 c | 1.15 ± 0.03 d | 0.69 ± 0.02 a | 1.10 ± 0.06 d |
5-O-Caffeoylquinic acid | 31.00 ± 0.36 g | 0.54 ± 0.01 a | 1.58 ± 0.06 f | 0.63 ± 0.02 b | 1.40 ± 0.02 e | 0.77 ± 0.02 c | 1.21 ± 0.04 d |
p-Coumaric acid | 4.60 ± 0.05 a | 9.72 ± 0.06 e | 8.70 ± 0.05 c | 12.04 ± 0.11 f | 8.80 ± 0.09 c | 7.55 ± 0.08 b | 9.17 ± 0.12 d |
Ferulic acid | 1.71 ± 0.03 a | 3.58 ± 0.06 f | 2.88 ± 0.03 c | 3.16 ± 0.06 e | 2.84 ± 0.01 c | 2.11 ± 0.06 b | 2.97 ± 0.03 d |
p-Hydroxyphenylacetic acid | 0.33 ± 0.00 b | 0.42 ± 0.01 c | 0.42 ± 0.01 c | 0.48 ± 0.02 d | 0.51 ± 0.01 e | 0.30 ± 0.01 a | 0.51 ± 0.02 e |
Quercetin-3-O-galactoside | 0.05 ± 0.00 d | ND | 0.03 ± 0.00 c | 0.01 ± 0.00 a | 0.02 ± 0.00 b | ND | 0.03 ± 0.00 c |
Rutin | 1.05 ± 0.03 e | 0.07 ± 0.01 c | 0.09 ± 0.01 d | 0.02 ± 0.00 a | 0.07 ± 0.00 c | 0.05 ± 0.00 b | 0.08 ± 0.01 cd |
Apigenin-7-O-glucoside | ND | ND | ND | ND | ND | ND | ND |
Quercetin | ND | ND | ND | ND | ND | ND | ND |
Luteolin | ND | ND | ND | ND | ND | ND | ND |
Naringin | 2.20 ± 0.02 f | 1.05 ± 0.02 c | 0.91 ± 0.02 a | 1.13 ± 0.02 d | 1.12 ± 0.06 d | 0.97 ± 0.03 b | 1.34 ± 0.06 e |
Kaempferol | ND | ND | ND | ND | ND | ND | ND |
Apigenin | ND | ND | ND | ND | ND | ND | ND |
Isorhamnetin-3-O-rutinoside | 0.12 ± 0.00 d | 0.03 ± 0.00 b | 0.04 ± 0.00 c | 0.04 ± 0.00 c | 0.02 ± 0.00 a | 0.02 ± 0.00 a | 0.03 ± 0.00 b |
Taxifolin | 0.28 ± 0.00 a | 0.84 ± 0.02 c | 1.11 ± 0.05 f | 0.98 ± 0.03 e | 0.90 ± 0.03 d | 0.64 ± 0.02 b | 1.00 ± 0.01 g |
Isorhamnetin-3-O-glucoside | 0.20 ± 0.00 a | 0.46 ± 0.01 c | 0.59 ± 0.02 d | 0.56 ± 0.03 d | 0.57 ± 0.02 d | 0.38 ± 0.01 b | ND |
Daidzein | 0.03 ± 0.00 a | ND | ND | ND | ND | ND | ND |
Eriodictyol | ND | ND | ND | ND | ND | ND | ND |
Chrysoeriol | ND | 0.03 | ND | ND | ND | 0.02 | ND |
Chrysin | ND | ND | ND | ND | ND | ND | ND |
Acacetin | ND | ND | ND | ND | ND | ND | ND |
Genkwanin | ND | ND | ND | ND | ND | ND | ND |
Galangin | ND | ND | ND | ND | ND | ND | ND |
Kaempferide | ND | ND | ND | ND | ND | ND | ND |
Total | 71.04 | 33.31 | 33.56 | 27.88 | 27.95 | 22.19 | 28.15 |
Compound | Content (mg/L) | ||||||
MAE | MAE-1 | MAE-2 | MAE-3 | MAE-4 | MAE-5 | MAE-6 | |
Protocatechuic acid | ND * | ND * | ND | ND | ND | ND | ND |
p-Hydroxybenzoic acid | 1.40 ± 0.03 a | 2.44 ± 0.02 de | 2.35 ± 0.02 c | 2.28 ± 0.02 b | 2.52 ± 0.06 e | 2.41 ± 0.03 d | 2.45 ± 0.03 de |
Caffeic acid | 53.70 ± 0.53 b | 41.96 ± 0.12 a | ND | ND | ND | ND | ND |
Vanillic acid | 1.40 ± 0.01 a | 1.72 ± 0.01 cd | 1.77 ± 0.03 d | 1.64 ± 0.01 b | 1.69 ± 0.02 c | 1.72 ± 0.02 cd | 1.69 ± 0.02 c |
Aesculin | 3.55 ± 0.03 f | 2.13 ± 0.03 b | 2.05 ± 0.03 a | 2.16 ± 0.02 bc | 2.42 ± 0.03 e | 2.22 ± 0.03 c | 2.26 ± 0.03 d |
5-O-Caffeoylquinic acid | 71.00 ± 0.46 g | 22.44 ± 0.15 f | 13.68 ± 0.01 d | 13.31 ± 0.11 c | 14.18 ± 0.11 e | 10.27 ± 0.12 b | 8.96 ± 0.09 a |
p-Coumaric acid | 10.05 ± 0.11 e | 7.24 ± 0.02 d | 6.38 ± 0.06 a | 6.53 ± 0.06 b | 7.29 ± 0.09 d | 6.79 ± 0.06 c | 6.52 ± 0.06 b |
Ferulic acid | 6.60 ± 0.09 g | 6.15 ± 0.06 f | 4.95 ± 0.04 d | 4.82 ± 0.06 c | 5.50 ± 0.05 e | 4.69 ± 0.04 b | 4.45 ± 0.04 a |
p-Hydroxyphenylacetic acid | 0.95 ± 0.03 a | 1.19 ± 0.04 c | 1.08 ± 0.02 bc | 1.04 ± 0.03 b | 1.14 ± 0.05 c | 1.04 ± 0.03 b | 1.06 ± 0.02 b |
Quercetin-3-O-galactoside | 0.13 ± 0.01 b | 0.02 ± 0.00 b | 0.01 ± 0.00 a | ND | 0.01 ± 0.00 a | ND | ND |
Rutin | 2.60 ± 0.08 e | 0.30 ± 0.01 d | 0.15 ± 0.01 c | 0.14 ± 0.02 c | 0.15 ± 0.01 c | 0.07 ± 0.01 b | 0.06 ± 0.00 a |
Apigenin-7-O-glucoside | 0.03 ± 0.00 b | 0.02 ± 0.00 a | 0.02 ± 0.00 a | 0.02 ± 0.00 a | 0.03 ± 0.00 b | 0.02 ± 0.00 a | 0.03 ± 0.00 b |
Quercetin | ND | ND | ND | ND | ND | ND | ND |
Luteolin | ND | ND | ND | ND | ND | ND | ND |
Naringin | 3.66 ± 0.06 f | 2.33 ± 0.04 d | 2.03 ± 0.03 a | 2.12 ± 0.03 b | 2.19 ± 0.03 c | 2.59 ± 0.03 e | 2.21 ± 0.03 c |
Kaempferol | ND | ND | ND | ND | ND | ND | ND |
Apigenin | ND | ND | ND | ND | ND | ND | ND |
Isorhamnetin-3-O-rutinoside | 0.16 ± 0.00 c | 0.08 ± 0.00 b | ND | ND | 0.04 ± 0.00 a | ND | ND |
Taxifolin | 0.62 ± 0.00 a | 1.88 ± 0.06 c | 1.90 ± 0.06 d | 1.96 ± 0.05 d | 2.18 ± 0.09 e | 1.72 ± 0.06 b | 1.76 ± 0.05 b |
Isorhamnetin-3-O-glucoside | 0.10 ± 0.00 a | ND | ND | ND | ND | ND | ND |
Daidzein | 0.08 ± 0.00 b | 0.03 ± 0.00 a | ND | ND | ND | ND | ND |
Eriodictyol | ND | ND | ND | ND | ND | ND | ND |
Chrysoeriol | ND | ND | 0.05 ± 0.00 a | ND | ND | ND | ND |
Chrysin | ND | ND | ND | ND | ND | ND | ND |
Acacetin | ND | ND | ND | ND | ND | ND | ND |
Genkwanin | ND | ND | ND | ND | ND | ND | ND |
Galangin | ND | ND | ND | ND | ND | ND | ND |
Kaempferide | ND | ND | ND | ND | ND | ND | ND |
Total | 156.03 | 89.94 | 36.41 | 36.02 | 39.30 | 33.55 | 31.42 |
Sample | Antioxidant Activity | ||
---|---|---|---|
IC50 (μg/mL) | EC50 (μg/mL) | HPMC (%/mL) | |
UAE | |||
UAE | 22.25 ± 0.11 h | 113.10 ± 0.22 l | 53.2 ± 3.3 a |
UAE-1 | 24.64 ± 0.12 k | 69.54 ± 0.19 h | 92.9 ± 2.1 c |
UAE-2 | 23.71 ± 0.10 j | 71.33 ± 0.20 j | 118.6 ± 7.8 d |
UAE-3 | 19.71 ± 0.09 f | 71.97 ± 0.22 k | 117.5 ± 6.9 d |
UAE-4 | 23.10 ± 0.15 i | 71.35 ± 0.16 j | 80.9 ± 6.4 bc |
UAE-5 | 21.69 ± 0.12 g | 66.14 ± 0.19 g | 63.9 ± 1.0 ab |
UAE-6 | 25.62 ± 0.12 l | 70.44 ± 0.16 i | 77.1 ± 4.0 bc |
MAE | |||
MAE | 18.92 ± 0.13 e | 69.36 ± 0.11 h | 148.0 ± 8.2 efg |
MAE-1 | 13.08 ± 0.11 ab | 60.54 ± 0.21 e | 164.0 ± 5.3 g |
MAE-2 | 12.86 ± 0.09 a | 59.27 ± 0.16 c | 143.2 ± 6.6 ef |
MAE-3 | 17.41 ± 0.10 c | 59.90 ± 0.25 d | 151.9 ± 4.5 efg |
MAE-4 | 18.09 ± 0.11 d | 58.62 ± 0.23 b | 163.4 ± 9.1 g |
MAE-5 | 13.29 ± 0.15 b | 62.97 ± 0.29 f | 159.6 ± 9.2 fg |
MAE-6 | 17.61 ± 0.15 c | 55.70 ± 0.33 a | 141.8 ± 5.7 e |
Sample | Cell Line/IC50 (μg/mL) | ||
---|---|---|---|
Hep2c | RD | L2OB | |
UAE | |||
UAE | 36.36 ± 0.12 i | 29.67 ± 0.34 g | 39.16 ± 0.32 i |
UAE-1 | 35.45 ± 0.39 i | 32.49 ± 0.98 h | 36.23 ± 0.76 h |
UAE-2 | 31.29 ± 0.83 h | 29.24 ± 0.38 g | 33.19 ± 0.43 g |
UAE-3 | 29.46 ± 0.54 g | 26.76 ± 0.83 f | 28.76 ± 0.64 e |
UAE-4 | 23.39 ± 0.72 e | 20.84 ± 0.16 d | 26.48 ± 0.13 d |
UAE-5 | 13.35 ± 0.15 b | 11.39 ± 0.30 b | 14.60 ± 0.08 c |
UAE-6 | 9.23 ± 0.67 a | 8.72 ± 0.23 a | 13.13 ± 0.32 b |
MAE | |||
MAE | 38.47 ± 0.43 j | 31.32 ± 0.54 h | 49.28 ± 0.45 j |
MAE-1 | 25.28 ± 0.20 f | 23.73 ± 0.67 e | 36.43 ± 0.18 h |
MAE-2 | 23.29 ± 0.82 e | 20.89 ± 0.29 d | 32.39 ± 0.38 fg |
MAE-3 | 20.43 ± 0.14 d | 18.18 ± 0.56 c | 31.45 ± 0.24 f |
MAE-4 | 18.34 ± 0.30 c | 17.35 ± 0.91 c | 25.83 ± 0.92 d |
MAE-5 | 14.49 ± 0.29 b | 11.08 ± 0.18 b | 15.65 ± 0.15 c |
MAE-6 | 10.17 ± 0.89 a | 9.46 ± 0.37 c | 11.30 ± 0.27 a |
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Đurović, S.; Pezo, L.; Gašić, U.; Gorjanović, S.; Pastor, F.; Bazarnova, J.G.; Smyatskaya, Y.A.; Zeković, Z. Recovery of Biologically Active Compounds from Stinging Nettle Leaves Part II: Processing of Exhausted Plant Material after Supercritical Fluid Extraction. Foods 2023, 12, 809. https://doi.org/10.3390/foods12040809
Đurović S, Pezo L, Gašić U, Gorjanović S, Pastor F, Bazarnova JG, Smyatskaya YA, Zeković Z. Recovery of Biologically Active Compounds from Stinging Nettle Leaves Part II: Processing of Exhausted Plant Material after Supercritical Fluid Extraction. Foods. 2023; 12(4):809. https://doi.org/10.3390/foods12040809
Chicago/Turabian StyleĐurović, Saša, Lato Pezo, Uroš Gašić, Stanislava Gorjanović, Ferenc Pastor, Julia G. Bazarnova, Yulia A. Smyatskaya, and Zoran Zeković. 2023. "Recovery of Biologically Active Compounds from Stinging Nettle Leaves Part II: Processing of Exhausted Plant Material after Supercritical Fluid Extraction" Foods 12, no. 4: 809. https://doi.org/10.3390/foods12040809