Comprehensive Extraction and Chemical Characterization of Bioactive Compounds in Tepals of Crocus sativus L.
Abstract
:1. Introduction
2. Phenolic Compounds
2.1. Flavonoids
2.2. Anthocyanins
3. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Antioxidant Activity | Flavonols | Benzoic Acids | Catechins | ||||||
---|---|---|---|---|---|---|---|---|---|
Extraction Method | TPC | Anthocyanins | FRAP | DPPH | ABTS | Hyperoside | Rutin | Ellagic Acid | Epicatechin |
M | 465.7 ± 36.4 | 119.7 ± 15.6 | 167.3 ± 10.2 | 5.53 ± 0.79 | 5.84 ± 1.1 | 2.00 ± 0.72 | 0.15 ± 0.04 | 1.63 ± 0.35 | 3.13 ± 0.72 |
UA | 486.9 ± 41.8 | 119.3 ± 12.8 | 141.1 ± 7.3 | 6.06 ± 1.12 | 8.88 ± 0.97 | 2.42 ± 0.37 | 0.13 ± 0.05 | 3.06 ± 0.66 | 5.27 ± 0.42 |
p | ns | ns | ** | ns | *** | ns | ns | *** | * |
Solvent (% methanol) | |||||||||
0% | 449.8 ± 35.5 b | 142.5 ± 23.5 a,b | 253.5 ± 5.3 a | 4.61 ± 1.27 | 5.56 ± 1.03 b | 2.96 ± 0.64 a | 0.16 ± 0.07 | 1.42 ± 0.35 b | 0.00 ± 0.00 b |
20% | 374.8 ± 47.2 b | 103.3 ± 18.9 a,b | 108.8 ± 11.7 c | 4.82 ± 1.86 | 6.45 ± 0.98 b | 2.98 ± 0.59 a | 0.09 ± 0.02 | 2.52 ± 0.18 a | 0.00 ± 0.00 b |
50% | 402.9 ± 28.0 b | 88.8 ± 15.9 b | 105.9 ± 15.2 c | 6.99 ± 1.43 | 10.53 ± 1.23 a | 1.34 ± 0.79 b | 0.16 ± 0.10 | 2.71 ± 0.31 a | 9.18 ± 0.97 a |
80% | 677.7 ± 23.4 a | 143.3 ± 22.3 a | 148.6 ± 10.4 b | 6.77 ± 1.76 | 6.79 ± 0.72 b | 1.53 ± 0.68 b | 0.21 ± 0.09 | 2.72 ± 0.22 a | 7.62 ± 1.65 a |
p | *** | * | *** | ns | *** | *** | ns | ** | *** |
Interaction | |||||||||
Extraction × Solvent | ns | ns | ** | ns | *** | *** | ns | ns | * |
Extractions | Cinnamic Acids | Benzoic Acids | Flavonols | Catechins | Vitamin C | ||||
---|---|---|---|---|---|---|---|---|---|
Ferulic Acid | Ellagic Acid | Hyperoside | Isoquercitrin | Quercitrin | Rutin | Epicatechin | |||
M | Water | 0.00 ± 0.00 b | 7.67 ± 3.69 a,b,c | 4.35 ± 1.04 c | 0.31 ± 0.22 c,d | 0.00 ± 0.00 b | 8.52 ± 3.91 c | 0.00 ± 0.00 b | 29.61 ± 6.05 a |
M | Met20 | 1.83 ± 0.31 a | 4.43 ± 4.15 c,d | 5.61 ± 0.52 a,b,c | 0.22 ± 0.12 c,d | 6.33 ± 5.27 a | 0.32 ± 0.31 d | 0.00 ± 0.00 b | 33.72 ± 0.89 a |
M | Met50 | 9.65 ± 2.62 a | 0.00 ± 0.00 e | 5.85 ± 4.31 b,c | 4.36 ± 3.49 a,b,c | 9.27 ± 3.47 a | 0.00 ± 0.00 d | 0.00 ± 0.00 b | 0.00 ± 0.00 b |
M | Met80 | 0.00 ± 0.00 b | 1.32 ± 0.33 d,e | 23.93 ± 15.51 a,b,c | 7.82 ± 3.09 a | 6.53 ± 0.29 a | 37.61 ± 2.22 a | 0.00 ± 0.00 b | 0.00 ± 0.00 b |
UAE | Water | 0.00 ± 0.00 b | 8.53 ± 8.45 b,c,d | 11.58 ± 4.09 a,b,c | 0.00 ± 0.00 d | 0.00 ± 0.00 b | 28.24 ± 4.83 a,b | 0.00 ± 0.00 b | 26.68 ± 4.71 a |
UAE | Met20 | 0.00 ± 0.00 b | 26.74 ± 10.80 a,b | 9.68 ± 6.77 a,b,c | 6.46 ± 5.03 a,b | 0.00 ± 0.00 b | 13.46 ± 10.25 b,c | 16.62 ± 15.89 a | 29.17 ± 2.31 a |
UAE | Met50 | 0.00 ± 0.00 b | 28.39 ± 4.32 a | 27.26 ± 4.29 a | 5.57 ± 1.90 a,b,c | 7.07 ± 5.12 a | 7.24 ± 1.35 c | 0.00 ± 0.00 b | 0.00 ± 0.00 b |
UAE | Met80 | 0.00 ± 0.00 b | 23.51 ± 5.11 a,b | 24.77 ± 2.25 a,b | 0.00 ± 0.00 d | 0.00 ± 0.00 b | 9.10 ± 2.17 c | 4.22 ± 2.90 a | 0.00 ± 0.00 b |
p | 0.001802 ** | 2.235 × 10−7 *** | 0.004662 ** | 0.005466 ** | 0.005407 ** | 1.452 × 10−10 *** | 0.001995 ** | 0.003143 ** |
Sample | Polyphenol Content (µg GA eq/mg Extract) |
---|---|
STG | (34.41 ± 1.09) |
TPL | (64.66 ± 0.20) |
LV | (38.56 ± 0.34) |
Extraction Method | Pre-Status | Main Compounds | Reference | Ref. N°. |
acidified methanol 80%, sonicated for 30 min in ice bath | frozen | flavonol glycosides and anthocianis | Orlando et al., 2022 | [24] |
Subcritical water | dried | phenolic compounds | Ahmadian-Kouchaksaraie et al., 2016 | [27] |
Supercritical Carbon Dioxide | dried | phenolic compounds, anthocyanins, flavonoids | Ahmadian-Kouchaksaraie et al., 2017 | [28] |
(a) hot water, (b) ohmic heating assisted extraction, (c) ultrasound assisted extraction, (d) microwave assisted extraction | dried | kaempferol derivatives and anthocyanins | Hashemi Gahruiea et al., 2020 | [29] |
(a) water/HCl 100:1 at 40 °C by stirring for 1h. (b) water/ACN/TFA (47:50:3). (c) water/ACN/HCl (50:50:1). (d) water/ethanol/HCl (50:50:1). (e) water/acetone/HCl (50:50:1) | frozen | kaempferol 3-O-sophoroside, kaempferol 3-O-glucoside, kaempferol, delphinidin 3,5-O-diglucoside, petunidin 3,5-O-diglucoside | Serrano-Diaz et al., 2014 | [30] |
(a) diethyl ether, (b) ethyl acetate, (c) aqueous | - | kaempferol, quercetin, naringenin, flavanone and flavanol derivatives glycosylated and esterified with phenylpropanoic acids. | Termentzi et al., 2008 | [31] |
methanol | - | flavonoids, glycosidic derivatives of quercetin and kaempferol | Montoro et al., 2008 | [33] |
dichloromethane, methanol, acetonitrile, diethyl ether, n-hexane and ethyl acetate | vacuum freeze drying | glycosilated forms of kaempferol, isorhamnetin, quercetin, glycolilated forms of anthocyanins | Goupy et al., 2013 | [38] |
ethanol | fresh | kinsenoside, goodyeroside, 3-hydroxy-γ-butyrolactone, kaempferol 3-O-sophoroside | Righi et al., 2015 | [39] |
methanol/HCL 9:1 | dried | kaempferol 3-O-sophoroside-7-O-glucoside, quercetin 3,4′-di-O-glucoside, delphinidin 3,5-di-O-β-glucoside, petunidin 3,5-di-O-β-glucoside, delphinidin 3-O-β-glucoside, petunidin 3-O-β-glucoside kaempferol 3,7′-di-O-glucoside, | Cusano et al., 2018 | [41] |
methanol/water 1:1 with ultrasonication | dried | astragalin, 1-monopalmitin, kaempferol-3,7-di-O-β-d-glucoside | Xu et al., 2019 | [43] |
ethanol/water 1:1 with ultrasonication | dired | kaempferol-3-O-sophoroside, quercetin-3-O-sophoroside, kaempferol-3-O-glucoside; | Mottaghipisheh et al., 2020 | [44] |
deionised water; deionized water:methanol (80:20 v/v); deionised water:methanol (50:50 v/v); deionised water:methanol (20:80 v/v). assisted extraction | fresh | hyperoside, rutin, ellagic acid, epicatechin, flavonols | Caser et al., 2020 | [45] |
Pressurized-Liquid Extraction | freeze dried | kaempferol 3-O-sophoroside, kaempferol 3-O-sophoroside 7-O-glucoside, quercetin 3-O-sophoroside, kaempferol 3-O-glucoside,. Delphinidin 3,5-di-O-glucoside, delphinidin 3-O-glucoside, petunidin 3,5-di-O-glucoside, delphinidin 3,5-di-O-glucoside | Pappas et al., 2021 | [46] |
Deep eutectic solvent (lactate and glycine) | dried | kaempferol 3-O-sophoroside 7-O-glucoside, quercetin 3-O-sophoroside, kaepferol 3-O-sophoroside, kaempferol 3-O-glucoside, delphinidin 3,5-di-O-glucoside, petunidin 3,5-di-O-glucoside, delphinidin 3-O-glucoside | Lakka et al., 2009 | [47] |
Ultrasound Assisted Extraction, using different water and methanol ratios like 20%, 50%, and 80% | ferulic acid (cinnamic acid); ellagic acid; hyperoside, isoquercitrin, quercitrin, rutin, epicatechin (catechin), vitamin C | Stelluti et al., 2021 | [48] | |
ultrasound assisted extractio of 4.5 g with 20 mL ethanol at 70 °C for 20 min | dried | kaempferol 3-O-glucoside, isorhamnetin 3-O-glucoside, kaempferol 3,7,4′-O-triglucoside, delphinidin 3,5-di-O-glucoside, myricetin-di-glucoside, primflasine | Gigliobianco et al., 2021 | [49] |
80/20 ethanol/water for 24 H | dried | kaempferol-3-O-sophoroside, quercetin and isorhamnetin glucosides. | Ouahhoud et al., 2022 | [50] |
methanol/MTBE 1:1 | freeze dried | several compounds divided into chemical classes | Bellachioma et al., 2022 | [51] |
water/HCl (100:1 v/v) | dried | delphinidin 3,5-di-O-β-glucoside, petunidin 3,5-di-O-β-glucoside, delphinidin 3-O-β-glucoside, malvidin 3,5-di-O-β-glucoside and petunidin 3-O-β-glucoside | Moratalla-López et al., 2017 | [67] |
ethanol/HCl (85:15 v/v) | freeze dried | Pelargonidin 3-glycosides,Pelargonidin 3,5-glycosides, Petunidin, 3,5 Cyanidin-diglycosides, Delphinidin 3-glycosides | Lofti et al., 2015 | [68] |
1 g extracted with 13 mL acetonitrile/water 1:1 containing 3.0% trifluoroacetic acid | freeze dried | several compounds divided into chemical classes | Nørbæk 2002 | [37] |
50 g extracted with acetonitrile/water 1:1 containing 0.5% trifluoroacetic acid | freeze dried | delphinidin 3-glucoside-5-(6-malonyl)glucoside, delphinidin 3,7-diglucosides, petunidin 3,7-diglucosides, delphinidin 3,5-diglucosides, petunidin 3,5-diglucosides | Nørbæk 1999 | [72] |
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Ruggieri, F.; Maggi, M.A.; Rossi, M.; Consonni, R. Comprehensive Extraction and Chemical Characterization of Bioactive Compounds in Tepals of Crocus sativus L. Molecules 2023, 28, 5976. https://doi.org/10.3390/molecules28165976
Ruggieri F, Maggi MA, Rossi M, Consonni R. Comprehensive Extraction and Chemical Characterization of Bioactive Compounds in Tepals of Crocus sativus L. Molecules. 2023; 28(16):5976. https://doi.org/10.3390/molecules28165976
Chicago/Turabian StyleRuggieri, Fabrizio, Maria Anna Maggi, Michela Rossi, and Roberto Consonni. 2023. "Comprehensive Extraction and Chemical Characterization of Bioactive Compounds in Tepals of Crocus sativus L." Molecules 28, no. 16: 5976. https://doi.org/10.3390/molecules28165976