Selective Extraction of Piceatannol from Passiflora edulis by-Products: Application of HSPs Strategy and Inhibition of Neurodegenerative Enzymes
Abstract
:1. Introduction
2. Results and Discussion
2.1. Piceatannol–Solvent Affinity
2.2. Single-Cycle PLE: PLE Yield, Piceatannol, and Total Phenolic Content (TPC) Quantification
2.3. Multi-Cycle PLE: Effect of Temperature and Number of Cycles
2.4. Tentative Identification of Phenolic Compounds from d-PFBP by UHPLC-q-TOF-MS/MS
2.5. Bioactivity of d-PFBP Extracts (AChE and LOX Inhibitory Effects)
3. Materials and Methods
3.1. Materials
3.2. Estimative of Hansen Solubility Parameters
3.3. Extraction Procedures
3.3.1. Supercritical Fluid Extraction: Defatting Step
3.3.2. Pressurized Liquid Extraction (PLE)
3.3.3. Conventional Solid–Liquid Extraction
3.4. Extract Characterization
3.4.1. High-Performance Liquid Chromatography with a Diode-Array Detector (HPLC-DAD): Piceatannol Quantification
3.4.2. Total Phenolic Content (TPC)
3.4.3. Phenolics Profile of d-PFBP Extract Using UHPLC-q-TOF-MS/MS
3.5. Bioactivities of d-PFBP Extracts
3.5.1. Acetylcholinesterase (AChE) Inhibition
3.5.2. Lipoxygenase (LOX) Inhibition
3.6. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Molecular Structure | Molecular Formula | Tb (°C) (at 0.1 Mpa) | δD (Mpa1/2) | δP (Mpa1/2) | δH (Mpa1/2) | δT (Mpa1/2) | Ra (Mpa1/2) | |
---|---|---|---|---|---|---|---|---|
Piceatannol (target) | C14H12O4 | - | 21.3 | 7.0 | 10.4 | 24.7 | 0 | |
BnOH | C7H8O | 205 | 18.4 | 6.3 | 13.7 | 23.8 | 6.7 | |
EtOAc | C4H8O | 77 | 15.8 | 5.3 | 7.2 | 18.2 | 11.6 | |
EtOH | C2H5OH | 78 | 15.8 | 8.8 | 19.4 | 26.5 | 14.3 | |
EtOH:H2O (79:21) | - | - | 15.7 | 10.3 | 24.2 | 31.0 | 18.0 |
Extraction | Solvent | T (°C) | Ra Value | Piceatannol (mg/g of Dried d-PFBP) | Piceatannol (mg/g of Dried Extract) | TPC (mg GAE/g of Dried Extract) |
---|---|---|---|---|---|---|
PLE (10 Mpa) | EtOH | 50 | 14.53 | n.q. | n.q. | 34.00 ± 0.08 d |
65 | 14.72 | n.q. | n.q. | n.d. | ||
80 | 14.96 | 0.23 ± 0.03 d | 3 ± 0 c | n.d. | ||
95 | 15.25 | 0.49 ± 0.03 c | 4.48 ± 0.05 c | n.d. | ||
110 | 15.59 | 1.43 ± 0.03 b | 11.0 ± 1.8 b | 91.4 ± 11.4 b | ||
EtOAc | 50 | 12.36 | n.q. | n.q. | 11.77 ± 0.25 d | |
65 | 12.84 | n.q. | n.q. | n.d. | ||
80 | 13.33 | n.q. | n.q. | n.d. | ||
95 | 13.83 | 0.128 ± 0.002 d | 3.130 ± 0.295 c | n.d. | ||
110 | 14.36 | 0.268 ± 0.007 d | 6.24 ± 0.36 c | 65.1 ± 8.5 c | ||
BnOH | 50 | 6.87 | n.q. | n.q. | 24.68 ± 2.55 d | |
65 | 6.99 | n.q. | n.q. | n.d. | ||
80 | 7.13 | n.q. | n.q. | n.d. | ||
95 | 7.27 | 0.27 ± 0.04 d | 3.4 ± 0.7 c | n.d. | ||
110 | 7.42 | 0.48 ± 0.04 c | 5.6 ± 0.2 c | 65.05 ± 8.03 c | ||
Solid–liquid | EtOH:H2O (79:21) | 85 | 17.6 | 1.81 ± 0.07 a | 23.4 ± 1.5 a | 269.6 ± 4.4 a |
Extraction | Solvent | T (°C) | Ra Value | Cycle | Yield (%, g/g of Dried d-PFBP) | Piceatannol (mg/g of Dried Extract) | TPC (mg GAE/g of Dried Extract) |
---|---|---|---|---|---|---|---|
PLE (10 MPa) | EtOH | 110 | 15.59 | 1 | 19.7 ± 1.5 ab | 11.0 ± 1.9 d | 91.4 ± 11.4 g |
2 | 3.17 ± 0.06 ef | 55.5 ± 6.9 a | 419.18 ± 10.15 b | ||||
3 | 1.80 ± 0.08 f | 56.5 ± 4.6 a | 490.1 ± 13.3 a | ||||
150 | 16.77 | 1 | 23 ± 1 a | 12.26 ± 0.16 d | 206 ± 5 de | ||
200 | 18.71 | 1 | 19.1 ± 2.2 b | 10.7 ± 0.8 d | 177 ± 7 ef | ||
EtOAc | 110 | 14.36 | 1 | 5.0 ± 0.7 de | 6.2 ± 0.4 d | 65 ± 8 g | |
2 | 0.980 ± 0.015 f | 23.8 ± 0.6 bc | 158 ± 12 f | ||||
3 | 0.51 ± 0.05 f | 32 ± 2 b | 178 ± 20 ef | ||||
BnOH | 110 | 7.42 | 1 | 8.7 ± 0.4 c | 5.6 ± 0.2 d | 65 ± 8 g | |
2 | 2.8 ± 0.1 ef | 6.09 ± 0.07 d | 176 ± 34 ef | ||||
3 | 1.8 ± 0.2 ef | 9.2 ± 0.7 d | 225 ± 43 cd | ||||
Solid-Liquid | EtOH:H2O (79:21) | 85 | 17.6 | - | 7.5 ± 0.3 cd | 23.4 ± 1.5 c | 270 ± 4 c |
Tentative Identification | RT (Min) | Molecular Formula | Calculated [M-H]− (m/z) | Experimental [M-H]− (m/z) | Error (ppm) | MS/MS Product Ions (m/z) | Reference a |
---|---|---|---|---|---|---|---|
Citric acid isomer I | 0.60 | C6H8O8 | 191.0197 | 191.0199 | 1.0 | 85.0312, 57.0367, 87.0111, 111.0102 | [42] |
Citric acid isomer II | 0.92 | C6H8O8 | 191.0197 | 191.0193 | −2.1 | 87.0112, 111.0118, 85.0324, 57.0371 | [42] |
Acacetin | 2.03 | C16H12O5 | 283.0612 | 283.0615 | 1.1 | 151.0278, 283.0685 | [CFM-ID] |
Dihydroxybenzoic acid | 2.41 | C7H6O4 | 153.0193 | 153.0194 | 0.7 | 109.0318, 108.0251, 91.0214, 65.0055 | [42] |
4-Hydroxybenzoic acid | 3.11 | C7H6O3 | 137.0244 | 137.0243 | −0.7 | 93.035, 65.0418 | [Std] |
Catechin | 3.54 | C15H14O6 | 289.0718 | 289.0720 | 0.7 | 123.0467, 203.0718, 245.0843, | [Std] |
Caffeic acid | 3.81 | C9H8O4 | 179.0350 | 179.0357 | 3.9 | 133.0322, 79.0585, 89.0429 | [Std] |
Taxifolin isomer I | 3.84 | C15H12O7 | 303.0510 | 303.0505 | −1.6 | 175.0368, 285.0424 | [Metlin] |
Catechin hexoside | 4.10 | C21H24O11 | 451.1246 | 121.0300 | 4.1 | 289.0741 | [42] |
Piceatannol diglucoside | 4.15 | C26H32O14 | 567.1719 | 451.1228 | −4.0 | 405.1208, 243.0677, 406.1224 | [CFM-ID] |
Epicatechin | 4.23 | C15H14O6 | 289.0718 | 567.1699 | −3.5 | 123.0466, 203.0718, 245.0843 | [Metlin] |
p-Coumaric acid | 4.69 | C9H8O3 | 163.0401 | 163.0398 | −1.8 | 119.0364, 163.0201, 147.0334 | [Std] |
Phloridzin | 4.70 | C21H24O10 | 435.1297 | 435.1284 | −3.0 | 273.0807, 123.0475 | [Metlin] |
Passiflorinol C/D-type | 4.90 | C29H24O10 | 531.1296 | 531.1289 | −1.5 | 362.0812, 265.0533 | [43] |
Passiflorinol C/D-type isomer | 5.38 | C29H24O10 | 531.1296 | 531.1288 | −1.6 | 283.0642, 165.0226 | [43] |
Taxifolin isomer II | 5.47 | C15H12O7 | 303.0510 | 303.0502 | −2.6 | 125.027, 175.0411, 285.0438 | [Metlin] |
Cyperusphenol B | 5.56 | C42H32O12 | 727.1821 | 727.1795 | −3.6 | 495.1126, 373.0740, 265.0542 | [43] |
Piceatannol | 5.72 | C14H12O4 | 243.0663 | 243.0667 | 1.6 | 243.0696, 159.0476, 201.0588 | [Std] |
Passiflorinol A/B-type | 6.09 | C42H32O12 | 727.1821 | 727.1803 | −2.5 | 617.1471, 361.0748, 243.0681 | [43] |
Tetrahydroxy(iso)flavanone | 6.30 | C15H12O6 | 287.0562 | 287.0567 | 1.7 | 259.0632, 125.0272 | [Metlin] |
cis-Resveratrol | 6.75 | C14H12O3 | 227.0714 | 227.0718 | 1.8 | 143.0521, 227.0735, 185.0654 | [Metlin] |
Scirpusin B | 7.13 | C28H22O8 | 485.1242 | 485.1228 | −2.9 | 485.1289, 375.0916, 486.1316 | [7] |
Passiflorinol A/B-type isomer | 7.19 | C42H32O12 | 727.1821 | 727.1805 | −2.2 | 618.1516, 483.1165, 373.0758, 243.0709 | [43] |
Cyperusphenol D | 7.36 | C42H30O12 | 725.1665 | 725.1640 | −3.4 | 617.1509, 481.0925, 373.0747, 243.0685 | [43] |
Quercetin | 7.56 | C15H10O7 | 301.0354 | 301.0352 | −0.7 | 151.0059, 179.0006, 301.0385 | [Std] |
Passiflorinol A/B-type isomer | 7.92 | C42H32O12 | 727.1821 | 727.1800 | −2.9 | 617.1516, 495.1102, 373.0747, 241.0555 | [43] |
Cassigarol D isomer I | 8.10 | C28H20O8 | 483.1085 | 483.1062 | −4.9 | 243.0695, 201.0571 | [43] |
Cassigarol D isomer II | 8.88 | C28H20O8 | 483.1085 | 483.1072 | −2.8 | 295.0637, 241.0519 | [43] |
Extraction | Solvent | T (°C) | Cycle | AChE IC50 (μg/mL) | LOX IC50 (μg/mL) |
---|---|---|---|---|---|
PLE (10 MPa) | 50 | 1 | 395.63 ± 9.774 a | 211.689 ± 12.279 a | |
EtOH | 110 | 1 | n.d. | 40.478 ± 0.597 b | |
2 | 43.297 ± 3.249 bc | 32.035 ± 1.355 b | |||
3 | 29.420 ± 1.615 c | 27.682 ± 2.477 b | |||
Solid-Liquid | EtOH:H2O (79:21) | 85 | - | 58.87 ± 0.05 b | 29.720 ± 2.627 b |
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dos Santos, L.C.; Mendiola, J.A.; Sánchez-Camargo, A.d.P.; Álvarez-Rivera, G.; Viganó, J.; Cifuentes, A.; Ibáñez, E.; Martínez, J. Selective Extraction of Piceatannol from Passiflora edulis by-Products: Application of HSPs Strategy and Inhibition of Neurodegenerative Enzymes. Int. J. Mol. Sci. 2021, 22, 6248. https://doi.org/10.3390/ijms22126248
dos Santos LC, Mendiola JA, Sánchez-Camargo AdP, Álvarez-Rivera G, Viganó J, Cifuentes A, Ibáñez E, Martínez J. Selective Extraction of Piceatannol from Passiflora edulis by-Products: Application of HSPs Strategy and Inhibition of Neurodegenerative Enzymes. International Journal of Molecular Sciences. 2021; 22(12):6248. https://doi.org/10.3390/ijms22126248
Chicago/Turabian Styledos Santos, Luana Cristina, Jose Antonio Mendiola, Andrea del Pilar Sánchez-Camargo, Gerardo Álvarez-Rivera, Juliane Viganó, Alejandro Cifuentes, Elena Ibáñez, and Julian Martínez. 2021. "Selective Extraction of Piceatannol from Passiflora edulis by-Products: Application of HSPs Strategy and Inhibition of Neurodegenerative Enzymes" International Journal of Molecular Sciences 22, no. 12: 6248. https://doi.org/10.3390/ijms22126248