Table 1.
Application of DES/NADES in combination with the ultrasound-assisted extraction (UAE) of bioactive compounds from the various plant material in the last three years.
| Plant Material | Selected DES/NADES (Number of Tested Solvents) |
∆Extraction Conditions | Type of Chemical Compounds/Index Determined | Instrumental Analysis | Reference | ||||
|---|---|---|---|---|---|---|---|---|---|
| A | B | C | D | E | |||||
| Phenolic Compounds | |||||||||
| Olive cake | Lactic acid:glucose (3) |
1:5 | 15 | 75/1 | 60 | 40 °C |
Phenolic acids:trans-ferulic acid, caffeic acid Flavonoids: tyrosol, 3-hydroxytyrosol, rutin hydrate, apigenin, luteolin |
HPLC-DAD | [53] |
| Onion | |||||||||
| Tomato waste | |||||||||
| Pear waste | |||||||||
| Mulberry leaves (Morus alba L.) |
§ChCl:citric acid (12) |
2:1 | 25% | 50/1 | 30 | 40 °C |
Phenolic acids: gallic acid, gentisic acid, chlorogenic acid, catechinic acid, vanillic acid, caffeic acid, syringic acid, benzoic aicd Flavonoids: epicatechin, rutin, hysperin, astragalin, quercetin |
HPLC-UV | [107] |
| Lycium ruthenicum Murr. | ChCl:1,2-propanediol (4) |
1:2 | 10% | 50/1 | 45 | 52 °C |
Anthocyanins: petunidin-3-O-rutinoside-5-O-glucoside, malvidin-derivative, petunidin-3-O-(glucosyl-trans-p-coumaroyl)- rutinoside-5-O-glucoside, petunidin-3-O-(glucosyl-cis-p-coumaroyl)-rutinoside-5-O-glucoside, petunidin-derivative, delphinidin-derivative, petunidin-3-O-(caffeoyl)-rutinoside-5-O-glucoside, delphinidin-3-O-(p-coumaroyl)-rutinoside-5-O-glucoside, petunidin-3-O-(cis-p-coumaroyl)-rutinoside-5-O-glucoside, petunidin-3-O-(trans-p-coumaroyl)-rutinoside-5-O-glucoside, petunidin-derivative,malvidin-3-O-(p-coumaroyl)-rutinoside-5-O-glucoside, petunidin-3-O-(p-coumaroyl)-rutinoside isomer |
HPLC-DAD/ESI-MS UPLC-Q-TOF-MS |
[118] |
| Peppermint leaves (Mentha piperita L.) |
ChCl:glucose (9) |
5:2 | ND | 100/1 | 45 | RT |
Phenolic acids: rosmarinic acid, salvianolic acid Flavonoids: eriocitrin, luteolin 7-O-rutinoside |
UHPLC-Q-TOF-MS | [112] |
| TPC, TFC, DPPH, ABTS, FRAP | Spectrophotometry | ||||||||
| Camellia oleifera flowers | ChCl:lactic acid (13) |
1:2 | 35% | 40/1 | 50 | 40 °C | Flavonoids: quercetin 3-O-rhamnoside, kaempferol 3-O-rhamnoside, quercetin, kaempferol | HPLC-DAD | [119] |
| Pollen Typhae | ChCl:1,2-propanediol (8) |
1:4 | 30% | 50/1 | 35 | ND | Flavonoid aglycons: quercetin, naringenin, kaempferol, isorhamnetin | HPLC-DAD LC-MS |
[110] |
| Larrea cuneifolia | Lactic acid:dextrose (1) |
5:1 | 15% | 75/1 | 42 | 40 °C |
Phenolic acids: caffeic acid, trans-ferulic acid, rosmarinic acid, cinnamic acid, nordihydroguaiaretic acid Flavonoids: ( ± ) ctechin hydrate, tyrosol, naringenin, apigenin, quercetin, luteolin, rutin hydrate |
HPLC-DAD | [120] |
| Greek propolis | ChCl:tartaric acid (1) |
2:1 | ND | ND | 30 | ND | TFC, TCTC, DPPH | Spectrophotometry | [121] |
| Lycium barbarum L. | ChCl:p-toluenesulfonic acid (11) |
1:2 | No | 50/1 | 90 | 25 °C |
Phenolic acids: chlorogenic acid, ferulic acid, p-coumaric acid Flavonoids: luteolin, rutin, myricetin, quercitrin, apigenin, hyperoside |
HPLC-UV/ViS | [66] |
| Buckwheat sprouts (Fagopyrum esculentum M.) |
ChCl:triethylene glycol (18) |
1:4 | 20% | 20/1 | 40 | 56 °C | Flavonoids: orientin, isoorientin, vitexin, isovitexin, quercetin-3-O-robinobioside, rutin | HPLC-Q-TOF/MS HPLC-PDA |
[47] |
| TFC | Spectrophotometry | ||||||||
| Safflower (Carthamus tinctorius L.) |
ChCl:ethylene glycol | 1:1 | ND | 17.8/1 | 55.9 | 41 °C | TFC | Spectrophotometry | [111] |
| Mature citrus (Nobis tangerine) |
ChCl: levulinic acid:N-methyl urea (18) |
1:1.2:0.8 | 20% | 20/1 | 25 | 50 °C | Flavonoids: narirutin, hesperidin, sinensetin, nobiletin, tangeretin, kaempferol-3-O-rutinoside, isosinensetin, 3,5,6,7,8,3′,4′-pentamethoxyflavone, 5-hydroxy-6,7,8,3′,4′-penta- methoxyflavon | UHPLC-UV UHPLC-Q-Orbitrap-MS/MS |
[122] |
| Beal (Aegle marmelos) |
ChCl:oxalic acid (1) |
1:1 | 25% | 20/1 | ND | 80 °C |
Phenolic acids: ascorbic acid, gallic acid, protocatechuic acid, p-coumaric acid, ferulic acid Flavonoids: quercetin, kaempferol, apigenin |
HPLC-UV | [106] |
| TPC | Spectrophotometry | ||||||||
| Byrsonima intermedia leaves | ChCl:glycerol (5) |
1:1 | 20% | 70.6/1 | 25 | 45 °C |
Phenolic acid: digalloyl quinic acid Proanthocyanidins: proanthocyanidin dimer, galloylproanthocyanidin dimer, Flavonoids: quercetin-O-hexoside, galloyl quercetin hexoside, quercetin-O-pentoside and galloyl quercetin pentoside |
HPLC-MS/MS HPLC-DAD |
[109] |
| DPPH, ABTS | Spectrophotometry | ||||||||
| Chickpea sprouts (Cicer arietinum L.) |
ChCl:propilene glycol (20) |
1:1 | 33% | 40/1 | 35 | 59 °C | Isoflavones: ononin, sissotrin, formononetin, biochanin A | UPLC-QqQ-MS/MS | [48] |
| TFC, DPPH, ABTS | Spectrophotometry | ||||||||
| Flos Trollii | ChCL:ZnBr2 (12) |
1:1 | 48% | 23.8/1 | 28 | 50 °C | Flavones: orientin, vitexin, 2′’-O-galactopyranosylorientin | HPLC-UV | [79] |
| Epimedium pubescens Maxim. | ChCl:lactic acid (18) |
1:2 | 17.5% | 6.4/1 | 21 | 25 °C | Prenylflavonol glycosides: epimedin A, epimedin B, epimedin C, icariin | HPLC-UV | [123] |
| Medicus flowers (Abelmoschus manihot Linn.) |
ChCl:acetic acid (7) |
1:2 | 30% | 35/1 | 30 | 30 °C | Flavonoids: hyperoside, isoquercitrin, myricetin | UHPLC-MS/MS | [124] |
| Myrothamnus flabellifolia Welw. | Sucrose:citric acid:water (4) |
1:1:10 | 25% | 50/1 | 90 | 50–55 °C |
Anthocyanins: cyanidin-3-acetyl glucosamine, cyanidin-3-p-coumaryl glucoside, delphinidin-3- glucoside, delphinidin-3-p-coumaryl glucoside, malvidin-3-acetyl glucoside, malvidin-3-glucoside, malvidin-3-coumaryl glucoside, pet-3-acetyl glucoside, pet-3-coumaryl glucoside | LC-QTOF-MS/MS | [125] |
| Rosemary (Rosmarinus officinalis L.) |
ChCl:1,2-propanediol (4) |
1:2 | 10% | 52.6/1 | 120 | 40 °C |
Phenolic acids: rosmarinic acid and ferulic acid Flavonoids: 7-methylrosmanol, rutin, naringin Other compounds: caffeine |
HPLC-DAD | [126] |
| TPC, DPPH, FRAP | Spectrophotometry | ||||||||
| Ginger (Zingiber officinale Roscoe) |
L-carnitine:1,3-butanediol (15) |
1:4 | 25% | 30/1 | 30 | 50 °C | Gingerols: 10-gingerol, 8-gingerol, 6-gingerol | HPLC-DAD | [64] |
| FRAP, ABTS | Spectrophotometry | ||||||||
| Elderberry plant (Sambucus nigra) |
Lactic acid:glycine (5) |
5:1 | 15% | 16.7/1 | 28 | RT |
Phenolic acids: neochlorogenic acid, hlorogenic acid, di-caffeoylquinic acid, p-coumaroylquinic acid derivative Flavonols: quercetin 3-O-rutinoside (rutin), quercetin 3-O-glucoside (isoquercitrin), isorhamnetin-3-O-rutinoside, quercetin |
LC-DAD-MS HPLC-DAD |
[127] |
| TPC, TFC, DPPH, FRAP | Spectrophotometry | ||||||||
| Extra-virgin olive oil | Betaine:glycerol (10) |
1:2 | 30% | 1/1 | 20 | RT |
Phenolic aclohols: hydroxytyrosol, tyrosol Secoiridoid derivatives: dialdehydic form of oleuropein aglycone, oleuropein aglycone isomer, lygstroside aglycone |
HPLC-DAD-ESI-MS HPLC-DAD |
[108] |
| Coffee pulp Cocoa pod husk cocoa husk |
ChCl:lactic acid (6) |
1:2 | 10% | 200/1 | 3 | 45 °C | Phenolic acid: chlorogenic acid | HPLC-UV UPLC-MS |
[105] |
| TPC | Spectrophotometry | ||||||||
| Cortex Fraxini | Betaine:glycerin (17) |
1:3 | 20% | 15/1 | 30 | ND | Coumarins: aesculetin, aesculin, fraxetin and fraxin | HPLC-UV | [128] |
| Coffee beans | Betaine:triethylene glycol (15) |
1:2 | 30% | 66.7/1 | 20 | 65 °C |
Phenolic acids: 3-O-caffeoylquinic acid, caffeoylepi-quinic acid, caffeoylepi-quinic acid, 5-O-caffeoylquinic acid, 4-O-caffeoylquinic acid, 5-pcoumaroylquinic acid, quinolactone, 4-feruloylquinic acid, 3-feruloylquinic acid, quinolactone, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, caffeoylferuloylquinic acid, caffeoylferuloylquinic acid |
HPLC-PDA/ESI-MS | [129] |
| Chokeberry (Aronia melanocarpa) |
ChCl:lactic acid (4) |
1:2 | 33% | 200/1 | 20 | 35 °C |
Phenolic acids: gallic acid, protcatehuic acid, chlorogenic acid, vanillic acid, caffeic acid, syringic acid, p-coumaric acid, trans-cinnamic acid and ferulic acid Flavonoids: epicatechin and quercetin |
HPLC-DAD | [130] |
| TPC, TFC, TAC | Spectrophotometry | ||||||||
| Hibiscus sabdariffa | Citric acid:ethylene glycol (1) |
1:4 | 50% | 12.5/1 | 43 | ND | TPC, TAC, DPPH, FRAP | Spectrophotometry | [131] |
| Moringa oleifera L. leaves | L-proline:glycerol (13) |
2:5 | 37% | 12.5/1 | 15 | 40 °C |
Phenolic acids: gallic acid, p-hydroxybenzoic acid, rosmarinic acid, Flavonoids: ( + )-catechin, vicenin-2, orientin, rutin, hyperoside, kaempferol-3-O-rutinoside, isorhamnetin 3-O-glucoside, quercetin; apigenin, kaempferol, (−)-epigallocatechin |
HPLC-ESI-Q-TOF-MS/MS | [132] |
| TPC, TFC, DPPH, ABTS, FRAP | Spectrophotometry | ||||||||
| Peumus boldus leaves | L-proline:oxalic acid (7) |
1:1 | 20% | 10/1 | 20 | RT | 21 different phenolic compounds | HPLC-PDA-IT-MS HPLC-ESI-QTOF-MS |
[133] |
| TPC | Spectrophotometry | ||||||||
| Alkaloids | |||||||||
| Carinum powellii bulbs | ChCl:fructose (10) |
5:2 | 35% | 400/1 | 60 | 50 °C | Lycorine, crinine, crinamine | HPTLC | [116] |
| Chinese dark tea (Camellia Sinensis L.) |
ChCl:lactic acid (8) |
1:1 | 31% | 34.5/1 | 38 | 58 °C | Caffeine | HPLC-UV | [103] |
|
Caulis inomenii,
Coptis chinensis, Stephania tetrandra, Tetradium ruticarpum, Sophora flavescens |
ChCl:lactic acid (8) |
1:2 | 30% | 60/1 | 30 | 54 °C | Sinomenine, magnoflorine, berberine hydrochloride, epiberberine, coptisine, palmatine hydrochloride, tetrandrine, fangchinolinee, evodiamine, rutaecarpine, matrine, oxymatrine | HPLC-UV | [117] |
| Peumus boldus leaves | L-proline:oxalic acid (7) |
1:1 | 20% | 10/1 | 20 | RT | Coclaurine, N-methylcoclaurine, laurolitsine, isoboldine, boldine, reticuline, isocorydine, laurotetanine, N-methyllaurotetanine | HPLC-IT-MS/MS | [133] |
∆Extraction conditions: A- molar ratio between HBD and HBA in the selected DES/NADES; B-water content in the selected DES/NADES (%); C-solid to liquid ratio (mg∙mL−1); D-extraction time (min); E-extraction temperature (°C). §ChCl- choline chloride.