The Application of Supercritical Fluid Extraction in Phenolic Compounds Isolation from Natural Plant Materials
Abstract
:1. Introduction
2. Phenolic Compounds
3. Low-Cost Sources of Phenolic Compounds
4. Separation of Phenolic Compounds with Supercritical CO2 Extraction
4.1. Applications
4.1.1. Pure Carbon Dioxide
4.1.2. Modified Carbon Dioxide
5. Combined SFE
6. SFE among Other Green Extraction Methods
7. Conclusions
8. Future Recommendations
Author Contributions
Funding
Conflicts of Interest
References
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Plant | Part of the Plant | Extraction Conditions | TPC (Total Phenolic Content) * | Reference | ||
---|---|---|---|---|---|---|
Solvent | Temperature [°C] | Pressure [bar] | ||||
Acai (Euterpe oleracea) | berries | CO2 | 50–70 | 150–490 | 137.5 mg/100 g (anthocyanins) | [98] |
Achillea millefolium | leaves | CO2 | 40 | 100–200 | 125–152.1 mg/g | [50] |
Baccharis dracunculifolia | leaves | CO2 | 40–60 | 200–400 | n.d. | [69] |
Blackberry (Rubus sp.) | bagasse | CO2 | 40–60 | 150–250 | 3.31–4.44 mg/g | [70] |
Black poplar (Populus nigra) | buds | CO2 | 60 | 300 | 31.09 µg/mg | [51] |
Cranberries | fruits | CO2 | 40 | 655 | n.d. | [66] |
Dandelion (Taraxacum officinale) | herb | CO2 | 40–60 | 200–400 | n.d. | [45] |
Dorema aucheri | herb | CO2 | 40–60 | 150–450 | n.d. | [72] |
Grape | seeds | CO2 | 35–60 | 50–150 | 15.6–22.56 g/kg | [41] |
seeds | CO2 | 75–104 | 230–538 | 190–350 mg/g | [40] | |
marc | CO2 | 40, 45 | 100, 120 | 300.9 mg/g | [99] | |
wine lees | CO2 | 40 | 350 | 11.9% (w/w) | [79] | |
Green tea | leaves | CO2 | 50, 70 | 100–300 | 530–578 mg/g | [100] |
Houttuynia cordata | grass | CO2 | 40 | 200 | n.d. | [78] |
Hyssop (Hyssop officinalis) | leaves | CO2 | 100 | 350 | n.d. | [33] |
Mango (Magnifera indica) | leaves | CO2 | 40–50 | 100–400 | n.d. | [82] |
Moringa oleifera | leaves | CO2 | 40–60 | 100–200 | n.d. | [25] |
Olive oil | mill waste | CO2 | 40 | 350 | 0.76% (w/w) | [58] |
Peach (Prunus persica) | fruits | CO2 | 40–60 | 100–300 | n.d. | [73] |
Phormidium valderianum | algae | CO2 | 40–60 | 200–500 | 117.15 μg/g | [74] |
Pomegranate (Punica granatum) | leaves | CO2 | 40, 50 | 100–300 | 257–389 mg/g | [81] |
Purslane (Portulaca oleracea) | seeds | CO2 | 60 | 235 | 173 mg/g | [71] |
Raspberry (Rubus sp.) | pomace | CO2 | 30–60 | 100–450 | n.d. | [88] |
Rosemary (Rosmarinus officinalis) | leaves | CO2 | 40,100 | 300 | n.d. | [80] |
CO2 | 100 | 350 | n.d. | [33] | ||
CO2 | 50 | 150–400 | 33% (w/w) | [37] | ||
CO2 | 25–50 | 80–120 | 230 mg/g | [85] | ||
CO2 | 30–40 | 100–300 | n.d. | [76] | ||
CO2 | 90–110 | 500–1000 | n.d. | [84] | ||
Rye (Secale cereale) | bran | CO2 | 30–70 | 250–550 | 14.62 mg/g | [89] |
Sage (Salvia officinalis) | leaves | CO2 | 100 | 350 | n.d. | [33] |
CO2 | 40, 100 | 300 | n.d. | [80] | ||
herbal dust | CO2 | 40–60 | 100–300 | n.d. | [96] | |
Spearmint (Mentha spicata) | leaves | CO2 | 40–60 | 100–300 | n.d. | [19] |
Strobilanthes crispus | leaves | CO2 | 40–60 | 100–200 | n.d. | [77] |
Theobroma cacao | hulls | CO2 | 50 | 100–200 | n.d. | [83] |
Thyme (Thymus vulgaris) | leaves | CO2 | 100 | 350 | n.d. | [33] |
Wheat germ | – | CO2 | 40–60 | 148–602 | 6 mg/g extract | [62] |
Wine | lees | CO2 | 40 | 300 | 11.9% (w/w) | [79] |
Whole flour, medium oat bran, fine bran, low bran | commercial | CO2 | 50 | 350 | n.d. | [87] |
Vaccinium meridionale | berries | CO2 | 40, 70 | 200, 300 | n.d. | [97] |
Plant | Part of the Plant | Extraction Conditions | TPC (Total Phenolic Content) * | Reference | ||
---|---|---|---|---|---|---|
Solvent | Temperature [°C] | Pressure [bar] | ||||
Acanthopanax Senticocus | leaves | CO2 + EtOH/H2O (80:20, v/v) | 30–60 | 200–350 | n.d. | [27] |
Anacardium occidentale | leaves | CO2, CO2 + EtOH (5%, w/w), CO2 + iPrOH (5%, w/w) | 35–55 | 100–300 | n.d. | [91] |
Apple | pomace | CO2 + EtOH (14–20%, wt %) | 40–60 | 200–600 | 0.47 mg/g | [4] |
Arrabidaea chica | leaves | CO2 (1 step), CO2 + EtOH + H2O (2 step) | 40 | 300 | 178 mg/g | [102] |
CO2 (1 step), CO2 + EtOH (acidified) (2 step), CO2 + H2O (acidified) (3 step) | 40, 50 | 300, 400 | 33–127 mg/g | [103] | ||
Bamboo (Sasa palmata) | leaves | CO2 + EtOH/H2O (5% (25:75, v/v)) | 50–110 | 100–250 | 7.31 mg/g (catechins) | [104] |
Bilberry (Vaccinium myrtillus) | press cake | CO2 + EtOH/H2O (50:50, v/v, acidified) | 50 | 350 | 16.67–43.66 mg/g | [105] |
fruits | CO2 + EtOH/H2O (6, 9%, w/w) | 45 | 250 | n.d. | [52] | |
Blackberry (Syzygium cumini) | fruits | CO2 + EtOH | 40–60 | 100–200 | n.d. | [106] |
Blueberry (Vaccinium myrtillus) | pomace | CO2 + EtOH | 60 | 80–300 | n.d. | [30] |
wastes | CO2 + EtOH (5%) + H2O (5%) | 40 | 150–250 | 134 mg/g | [20] | |
Bupleurum kaoi | roots | CO2 + EtOH | 40 | 50–200 | 180–190 μg/g | [107] |
Calycopteris florbunda | leaves | CO2 + EtOH (5%, mass%) | 30–50 | 100–300 | n.d. | [47] |
Carob (Ceratonia siliqua) | pods | CO2 + EtOH/H2O (10% (80:20, v/v)) | 40 | 220 | 27.1 mg/g | [108] |
Chokeberry (Aronia melanocarpa) | pomace | CO2 + EtOH (20, 50, 80, m/m) | 35, 50, 65 | 75, 100, 125 | 1.87–1.93 mg/g | [109] |
Citrus paradisi | peels | CO2 + EtOH (5, 10, 15%, wt %) | 58.6 | 95 | n.d. | [110] |
Coffee | spent ground coffee | CO2 + EtOH (5–25%, w/w) | 40–60 | 350–500 | 2.99 mg/g | [2] |
Cranberries | pomace | CO2 + EtOH | 60 | 80–300 | n.d. | [30] |
Elderberry (Sambucus nigra) | berries | CO2 + EtOH/H2O (50:50, v/v) | 20–60 | 150–300 | 60.6 mg/g | [111] |
CO2 + EtOH/H2O (10% (80:20, v/v)) | 40 | 210 | 15.8% | [31] | ||
Eucalyptus (Eucalyptus globulus) | bark | CO2, CO2 + EtOH, CO2 + EtAc, CO2 + H2O | 50–70 | 300 | 57.22 mg/g | [112] |
leaves | CO2 + EtOH | 35–50 | 100–200 | n.d. | [113] | |
Gingko (Ginkgo biloba) | leaves | CO2 + EtOH (5, 10, 12, 24% (mol%)) | 50–120 | 242–312 | 1342 µg/g | [114] |
Grape | cane | CO2 + EtOH (20%, v/v) | 50 | 300 | n.d. | [106] |
seeds | CO2 + MeOH (10, 40%, v/v), CO2 + EtOH (10, 40%, v/v) | 35, 55 | 350 | n.d. | [115] | |
seeds | CO2 + MeOH (2, 5,10, 15%, v/v), CO2 + EtOH (2, 5, 10, 15%, v/v) | 40 | 200–300 | n.d. | [116] | |
seeds | CO2, CO2 + MeOH (40%) | 80 | 646 | n.d. | [117] | |
seeds | CO2 + EtOH (7%) | 37–46 | 137–167 | 2.41 mg/g | [118] | |
seeds | CO2 + EtOH (10, 15, 20%, w/w) | 40 | 80, 100, 120 | 7221 mg/g | [7] | |
skins, seeds | CO2 + EtOH (5–25%, w/w) | 40–60 | 350–500 | 2.99 mg/g | [2] | |
marc | CO2 + EtOH/H2O (15% (57:43, v/v)) | 40 | 80–300 | 2600 mg/g | [119] | |
marc | CO2 + H2O (15%, w/w), CO2 + EtOH (15%, w/w) | 40–60 | 100, 200 | 733.6 mg/g | [120] | |
marc | CO2 + EtOH/H2O (10%) | 40 | 80 | 2736 mg/g | [108] | |
skin | CO2 + EtOH (7.5%) | 40 | 150 | n.d. | [121] | |
skin | CO2 + EtOH (25–30%) | 30–40 | 100–300 | n.d. | [122] | |
pomace | CO2, CO2 + EtOH (8%) | 35, 50 | 80, 350 | n.d. | [123] | |
pomace | CO2 + EtOH (5%, v/v) | 35, 55 | 100, 400 | n.d. | [124] | |
by–products | CO2, CO2 + MeOH (5%, v/v) | 45 | 150–250 | 18.1% (w/w) | [95] | |
peels | CO2 + EtOH (6–7%) | 37–46 | 157–162 | 2.156 mg/100 ml | [39] | |
bagasse | CO2 + EtOH (10%, wt %) | 40 | 200–350 | 23.0 g/kg | [13] | |
by–products, skin, marc | CO2 + EtOH | 45 | 200–500 | 28.12 mg/100g skin | [125] | |
wastes | CO2, CO2 + MeOH (40%) | 35 | 103 | n.d. | [17] | |
lees from the manufacturing of pisco | CO2 + EtOH (10%, wt %) | 40 | 200, 350 | 2796 mg/kg | [68] | |
Green algae | – | CO2 + EtOH (0–15%, wt %) | 40–60 | 100–300 | 30.20 mg/g | [126] |
Green coffee | beans | CO2, CO2 + EtOH (5%, w/w), CO2 + iPrOH (5%, w/w) | 50, 60 | 150, 248, 352 | n.d. | [92] |
Green propolis | – | CO2 + EtOH (1, 2%) | 40, 50 | 250–400 | 80.3 mg/g | [127] |
Green tea | commercial | CO2, CO2 + H2O, CO2 + EtOH (18%, 70%, 95%, 99.8%, aq) | 50 | 310 | n.d. | [93] |
powdered | CO2, CO2 +H2O | 40–60 | 200–300 | n.d. | [128] | |
leaves | CO2, CO2 + EtOH, CO2 + EtAc, CO2 + EtLac | 70 | 300 | 6.7 mg/g tea (catechin equivalent) | [129] | |
Guava (Psidium guajava) | seeds | CO2 + EtOH (10%, w/w), CO2 + EtAc | 50, 60 | 100–300 | n.d. | [46] |
Hazelnuts | bug– damaged nuts, rotten nuts | CO2 + EtOH (5–25%, w/w) | 40–60 | 350–500 | 2.99 mg/g | [2] |
Hops (Humulus lupulus) | pellets | CO2 + EtOH/H2O (80:20, v/v) | 50 | 250 | n.d. | [130] |
Jatoba (Hymenaea courbail) | bark | CO2 + H2O (9:1, v/v) | 50–60 | 150–350 | 335 mg/g (tannic acid equivalent) | [23] |
Jucara (Euterpe edulis) | residues | CO2 + EtOH/H2O (50:50, v/v) | 60 | 200 | 30 mg/g | [131] |
Koreanum nakai | leaves | CO2 + EtOH (70:30, v/v) | 40–70 | 200–350 | n.d. | [132] |
Maydis stigma | flowers | CO2 + EtOH (20% aq) | 40–60 | 250–450 | 3.99 mg/g | [5] |
Melia azedarach | fruits | CO2, CO2 + EtOH, EtOH, EtOH + H2O | 50 | 300 | 35 mg/g (catechin equivalent) | [133] |
Momordica charantia | fruits | CO2 + EtOH (85% aq) | 40–60 | 250–350 | 15 mg/g (flavonoids) | [134] |
Myrtle (Myrthus communis) | leaves | CO2, CO2 + EtOH (0–30%, wt %) | 35–60 | 100–300 | 4 μmol/g; 16 μmol/g | [94] |
leaves, berries | CO2 + EtOH | 45 | 230 | n.d. | [24] | |
Odontonema strictum | leaves | CO2 + EtOH (15%) | 55, 65 | 200, 250 | 99.33–247.78 mg/g | [135] |
Oats (Avena sativa) | – | CO2 + EtOH (80:20, v/v) | 40–70 | 140–620 | 1.25 mg/g | [136] |
Olive | leaves | CO2 + MeOH (10%) | 100 | 334 | n.d. | [137] |
Orange (Citrus sinensis) | pomace | CO2, CO2 + EtOH (2, 5, 8%, w/w) | 40, 50 | 100–300 | 36 mg/g | [59] |
Patrinia villosa | – | CO2 + MeOH (10, 20%) | 45–60 | 150–350 | n.d. | [138] |
Peach (Prunus persica) | pomace | CO2 + EtOH (14–20%, wt %) | 40–60 | 200–600 | 0.26 mg/g | [4] |
leaves | CO2 + EtOH (6–20%, wt %) | 40–80 | 150–300 | 79.92 mg/g | [139] | |
Pigeonpea (Cajanus cajan) | seedlings | CO2 + EtOH (80:20, v/v) | 45–65 | 250–350 | n.d. | [44] |
Pistachio (Pistachia vera) | hulls | CO2, CO2 + MeOH (5, 15%) | 35–55 | 100–350 | 7.8 mg/g (tannic acid equivalent) | [140] |
Pitanga (Eugenia uniflora) | leaves | CO2 (1 step), CO2 + EtOH (2 step), CO2 + H2O (3 step) | 60 | 400 | 240.5 mg/g | [18] |
Pomegranate (Punica granatum) | seeds | CO2 + H2O (0, 9, 18 ml/100 g sample), CO2 + EtOH (0, 9, 18 ml/100 g sample), CO2 + hexane (0, 9, 18 mL/100 g sample) | 40–60 | 200, 275, 350 | 7.8–72.1 mg/g (tannic acid equivalent) | [26] |
Pomelo (Citrus grandis) | peels | CO2 + EtOH (85:15, v/v) | 60–80 | 280–420 | n.d. | [60] |
Puearia lobata | roots | CO2 + EtOH (100, 200 mL) | 40–60 | 150–250 | 173.3 mg/g (flavonoids) | [48] |
Purple corn (Zea mays) | cob, pericarp | CO2 (1 step), CO2 + EtOH (2 step), CO2 + H2O (3 step) | 50 | 400 | n.d.. | [141] |
cobs | CO2 + EtOH/H2O (50, 70% aq) | 50 | 400 | 290 mg/g | [8] | |
cob | CO2 (1 step), CO2 + EtOH (2 step), CO2 + H2O (3 step) | 36–64 | 259–541 | n.d. | [142] | |
Raspberry (Rubus sp.) | pomace | CO2 + EtOH | 60 | 80–300 | n.d. | [30] |
Rosemary (Rosmarinus officinalis) | leaves | CO2, CO2 + EtOH (2%, v/v) | 40–60 | 300–350 | n.d. | [75] |
CO2, CO2 + EtOH (4, 7%, v/v) | 40–60 | 150–350 | n.d. | [90] | ||
CO2 (1 step), CO2 + EtOH (2 step) | 40 | 150, 300 | 177.61–203.92 mg/g | [143] | ||
CO2 + MeOH (5%) | 100 | 350 | 160 mg/g | [34] | ||
Scutellariae Radix | roots | CO2 + MeOH (5, 10, 15%, v/v) | 40–70 | 200–400 | n.d. | [144] |
Solanum stenotomun | peels | CO2, CO2 + EtOH (5%, v/v) | 35, 65 | 100, 400 | n.d. | [54] |
Soybean | meal | CO2 + MeOH /H2O (80:20, v/v) | 40–70 | 300–600 | n.d. | [65] |
cake | CO2 + EtOH/H2O (70:30, v/v) | 50–80 | 300–400 | n.d. | [64] | |
expellers | CO2 + EtOH | 35, 40 | 400 | 10.6–16.0 mg/100 g | [145] | |
Spruce bark (Picea abies) | wastes | CO2, CO2 + EtOH (70:30, v/v) | 40–60 | 100–200 | 314.49 mg/g | [57] |
Sweet basil (Ocimum basicilum) | leaves, roots | CO2 + H2O (1, 10, 20%, wt %) | 30–50 | 100–300 | n.d. | [146] |
Tea (Camelia sinensis) | seed cake | CO2 + EtOH/H2O (60:40, v/v) | 40–80 | 150–450 | n.d. | [147] |
Theobroma cacao | pod husk | CO2 + EtOH (13.7%) | 40–60 | 100–300 | 12.87 mg/g | [148] |
Undaria pinnatifida | seaweed | CO2 + EtOH (3%, v/v) | 30–60 | 80–300 | 700 µg/g | [86] |
Wine | by–products | CO2, CO2 + MeOH (5%, v/v) | 45 | 150–250 | 18.1% (w/w) | [95] |
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Tyśkiewicz, K.; Konkol, M.; Rój, E. The Application of Supercritical Fluid Extraction in Phenolic Compounds Isolation from Natural Plant Materials. Molecules 2018, 23, 2625. https://doi.org/10.3390/molecules23102625
Tyśkiewicz K, Konkol M, Rój E. The Application of Supercritical Fluid Extraction in Phenolic Compounds Isolation from Natural Plant Materials. Molecules. 2018; 23(10):2625. https://doi.org/10.3390/molecules23102625
Chicago/Turabian StyleTyśkiewicz, Katarzyna, Marcin Konkol, and Edward Rój. 2018. "The Application of Supercritical Fluid Extraction in Phenolic Compounds Isolation from Natural Plant Materials" Molecules 23, no. 10: 2625. https://doi.org/10.3390/molecules23102625