Antioxidant Properties of Polyphenolic Extracts from Quercus Laurina, Quercus Crassifolia, and Quercus Scytophylla Bark
Abstract
:1. Introduction
2. Materials and Methods
2.1. Raw Material
2.2. Polyphenol Crude Extracts
2.2.1. Extraction by Maceration
2.2.2. Extraction by Hot Water
2.3. Crude Extract Composition
2.4. Antioxidant Capacity of Crude Extracts
2.4.1. Superoxide Anion Radical (O2•−) Scavenging Activity
2.4.2. Hydrogen Peroxide (H2O2) Scavenging Activity
2.4.3. Hydroxyl Radical (OH•) Scavenging Activity
2.4.4. Nitric Oxide Radical (NO•) Scavenging Activity
2.4.5. Peroxyl Radical (ROO•) Scavenging Activity
2.4.6. Hypochlorous Acid (HClO) Scavenging Activity
2.5. Liquid–Liquid Purification of the Most Antioxidant Extract Selected: Composition and Antioxidant Capacity of the Purified Extract
2.6. Statistical Analysis
3. Results and Discussion
3.1. Yields and Chemical Composition of Crude Extracts from Quercus sp.
3.2. Antioxidant Capacity of Crude Extracts from Quercus sp.
3.3. Chemical Composition and Antioxidant Capacity of Purified Q. crassifolia Extract
4. Conclusions
Author Contributions
Acknowledgments
Conflicts of Interest
References
- Castro-Vázquez, L.; Alañón, M.E.; Ricardo-da-Silva, J.M.; Pérez-Coello, M.S.; Laureano, O. Evaluation of Portuguese and Spanish Quercus pyrenaica and Castanea sativa species used in cooperage as natural source of phenolic compounds. Eur. Food Res. Technol. 2013, 237, 367–375. [Google Scholar] [CrossRef]
- Aroso, I.M.; Fernandes, E.M.; Pires, R.A.; Mano, J.F.; Reis, R.L. Cork extractives exhibit thermo-oxidative protection properties in polypropylene–cork composites and as direct additives for polypropylene. Polym. Degrad. Stab. 2015, 116, 45–52. [Google Scholar] [CrossRef] [Green Version]
- Rosales-Castro, M.; González-Laredo, R.F.; Rocha-Guzman, N.E.; Gallegos-Infante, J.A.; Rivas-Arreola, M.J.; Karchesy, J.J. Antioxidant activity of fractions from Quercus sideroxyla bark and identifi cation of proanthocyanidins by HPLC-DAD and HPLC-MS. Holzforschung 2012, 66, 577–584. [Google Scholar] [CrossRef]
- Sroka, Z.; Franiczek, R. Antiradical and Antimicrobial Activity of Extracts Obtained from Plant Raw Materials. Adv. Clin. Exp. Med. 2008, 17, 275–283. [Google Scholar]
- Dróżdż, P.; Pyrzynska, K. Assessment of polyphenol content and antioxidant activity of oak bark extracts. Eur. J. Wood Wood Prod. 2018, 7, 793–795. [Google Scholar] [CrossRef]
- Ruiz-Aquino, F.; González-Peña, M.M.; Valdez-Hernández, J.I.; Revilla, U.S.; Romero-Manzanares, A. Chemical Characterization and Fuel Properties of Wood and Bark of Two Oaks from Oaxaca, Mexico. Ind. Crops Prod. 2015, 65, 90–95. [Google Scholar] [CrossRef]
- Stevanovic, T.; Diouf, P.N.; Garcia-Perez, M.E. Bioactive Polyphenols from Healthy Diets and Forest Biomass. Curr. Nutr. Food Sci. 2009, 5, 264–295. [Google Scholar] [CrossRef]
- Garrido, J.; Borges, F. Wine and grape polyphenols—A chemical perspective. Food Res. Int. 2013, 54, 1844–1858. [Google Scholar] [CrossRef]
- Duda-Chodak, A. The inhibitory effect of polyphenols on human gut microbiota. J. Physiol. Pharmacol. 2012, 63, 497–503. [Google Scholar] [PubMed]
- Lü, J.-M.; Lin, P.H.; Yao, Q.; Chen, C. Chemical and molecular mechanisms of antioxidants: Experimental approaches and model systems. J. Cell. Mol. Med. 2010, 14, 840–860. [Google Scholar] [CrossRef] [PubMed]
- Upadhyay, S.; Dixit, M. Role of polyphenols and other phytochemicals on molecular signaling. Oxid. Med. Cell. Longev. 2015, 2015, 504253. [Google Scholar] [CrossRef] [PubMed]
- He, Y.-Q.; Ma, Z.-Y.; Zhang, J.; Du, B.-Z.; Yao, B.-H. Antioxidant activity of the chemical constituents from the leaves of Quercus macrocarpa. Chem. Nat. Compd. 2011, 47, 472–473. [Google Scholar] [CrossRef]
- Popovic, B.M.; Štajner, D.; Zdero, R.; Orlovi, S.; Galic, Z. Antioxidant Characterization of Oak Extracts Combining Spectrophotometric Assays and Chemometrics. Sci. World J. 2013, 2013, 134656. [Google Scholar] [CrossRef] [PubMed]
- Custódio, L.; Patarra, J.; Alberício, F.; Neng, N.R.; Nogueira, J.M.F.; Romano, A. Extracts from Quercus sp. acorns exhibit in vitro neuroprotective features through inhibition of cholinesterase and protection of the human dopaminergic cell line SH-SY5Y from hydrogen peroxide-induced cytotoxicity. Ind. Crops Prod. 2013, 45, 114–120. [Google Scholar] [CrossRef]
- Söhretoğlu, D.; Sabuncuoğlu, S.; Harput, U.Ş. Evaluation of antioxidative, protective effect against H2O2 induced cytotoxicity, and cytotoxic activities of three different Quercus species. Food Chem. Toxicol. 2012, 50, 141–146. [Google Scholar] [CrossRef] [PubMed]
- Vázquez, L.M.; Valencia, A.S.; Nixon, K.C. Notes on red oaks (Quercus sect. Lobatae) in eastern Mexico, with description of a new species, Quercus hirtifolia. Brittonia 2004, 56, 136–142. [Google Scholar] [CrossRef]
- Sánchez-Burgos, J.A.; Ramírez-Mares, M.V.; Larrosa, M.M.; Gallegos-Infante, J.A.; González-Laredo, R.F.; Medina-Torres, L.; Rocha-Guzmán, N.E. Antioxidant, antimicrobial, antitopoisomerase and gastroprotective effect of herbal infusions from four Quercus species. Ind. Crops Prod. 2013, 42, 57–62. [Google Scholar] [CrossRef]
- Alañón, M.E.; Castro-Vázquez, L.; Díaz-Maroto, M.C.; Hermosín-Gutiérrez, I.; Gordon, M.H.; Pérez-Coello, M.S. Antioxidant capacity and phenolic composition of different woods used in cooperage. Food Chem. 2011, 129, 1584–1590. [Google Scholar] [CrossRef]
- Rakić, S.; Povrenović, D.; Tešević, V.; Simić, M.; Maletić, R. Oak acorn, polyphenols and antioxidant activity in functional food. J. Food Eng. 2006, 74, 416–423. [Google Scholar] [CrossRef]
- Rodríguez-Flores, S.M.; Escuredo, O.; Seijo, C.M. Assessment of Physicochemical and Antioxidant Characteristics of Quercus pyrenaica Honeydew Honeys. Food Chem. 2015, 166, 101–106. [Google Scholar] [CrossRef] [PubMed]
- Moreno-Jimenez, M.R.; Trujillo-Esquivel, F.; Gallegos-Corona, M.A.; Reynoso-Camacho, R.; González-Laredo, R.F.; Gallegos-Infante, J.A.; Rocha-Guzmán, N.E.; Ramos-Gomez, M. Antioxidant, anti-inflammatory and anticarcinogenic activities of edible red oak (Quercus spp.) infusions in rat colon carcinogenesis induced by 1,2-dimethylhydrazine. Food Chem. Toxicol. 2015, 80, 144–153. [Google Scholar] [CrossRef] [PubMed]
- McCune, L.M.; Johns, T. Antioxidant activity in medicinal plants associated with the symptoms of diabetes mellitus used by the Indigenous Peoples of the North American boreal forest. J. Ethnopharmacol. 2002, 82, 197–205. [Google Scholar] [CrossRef]
- Diouf, P.N.; Stevanovic, T.; Cloutier, A. Study on chemical composition, antioxidant and anti-inflammatory activities of hot water extract from Picea mariana bark and its proanthocyanidin-rich fractions. Food Chem. 2009, 113, 897–902. [Google Scholar] [CrossRef]
- Poussard, S.; Pires-Alves, A.; Diallo, R.; Dupuy, J.-W.; Dargelos, E. A Natural Antioxidant Pine Bark Extract, Oligopin(R), Regulates the Stress Chaperone HSPB1 in Human Skeletal Muscle Cells: A Proteomics Approach. Phyther. Res. 2013, 27, 1529–1535. [Google Scholar] [CrossRef] [PubMed]
- Scalbert, A.; Monties, B.; Janin, G. Tannins in Wood: Comparison of Different Estimation Methods. J. Agric. Food Chem. 1989, 37, 1324–1329. [Google Scholar] [CrossRef]
- Brighente, I.M.C.; Dias, M.; Verdi, L.G.; Pizzolatti, M.G. Antioxidant Activity and Total Phenolic Content of Some Brazilian Species. Pharm. Biol. 2007, 45, 156–161. [Google Scholar] [CrossRef] [Green Version]
- Council of Europe. European Pharmacopoeia, 4th ed.; European Directorate for the Quality of Medicines and Heald Care: Strausbourg, Francia, 2002; pp. 331–332. [Google Scholar]
- Porter, L.J.; Hrstich, L.N.; Chan, B.G. The Conversion of Procyanidins and Prodelphinidins to Cyanidin and Delphinidin. Phytochemistry 1986, 26, 223–230. [Google Scholar] [CrossRef]
- García-Pérez, M.-E.; Royer, M.; Duque-fernandez, A.; Diouf, P.N.; Stevanovic, T.; Pouliot, R. Antioxidant, toxicological and antiproliferative properties of Canadian polyphenolic extracts on normal and psoriatic keratinocytes. J. Ethnopharmacol. 2010, 132, 251–258. [Google Scholar] [CrossRef] [PubMed]
- Nishikimi, M.; Rao, A.N.; Yagi, K. The Occurrence of Superoxide Anion in the Reaction of Reduced Phenazine Methosulfate and Molecular Oxygen. Biochem. Biophys. Res. Commun. 1972, 46, 849–854. [Google Scholar] [CrossRef]
- Ruch, R.J.; Cheng, S.; Klaunig, J.E. Prevention of Cytotoxicity and Inhibition of Intercellular Communication by Antioxidant Catechins Isolated from Chinese Green Tea. Carcinogenesis 1989, 10, 1003–1008. [Google Scholar] [CrossRef] [PubMed]
- Smirnoff, N.; Cumbes, Q.J. Hydroxyl radical scavenging activity of compatible solutes. Phytochemistry 1989, 28, 1057–1060. [Google Scholar] [CrossRef]
- Rao, M.N.A. Nitric oxide scavenging by curcuminoids. J. Pharm. Pharmacol. 1997, 49, 105–107. [Google Scholar] [CrossRef]
- López-Alarcón, C.; Lissi, E. Interaction of pyrogallol red with peroxyl radicals. A basis for a simple methodology for the evaluation of antioxidant capabilities. Free Radic. Res. 2005, 39, 729–736. [Google Scholar] [CrossRef] [PubMed]
- Aruoma, O.I.; Halliwell, B. Action of hypochlorous acid on the antioxidant protective enzymes superoxide dismutase, catalase and glutathione peroxidase. Biochem. J. 1987, 248, 973–976. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- StatSoft, STATISTICA. 2007. Available online: http://statistica.io (accessed on 22 June 2018).
- Naima, R.; Oumam, M.; Hannache, H.; Sesbou, A.; Charrier, B.; Pizzi, A.; Charrier, F.; Bouhtoury, F. Comparison of the impact of different extraction methods on polyphenols yields and tannins extracted from Moroccan Acacia mollissima barks. Ind. Crops Prod. 2015, 70, 245–252. [Google Scholar] [CrossRef]
- Ammon, H.P.; Wahl, M.A. Pharmacology of Curcuma longa. Planta Med. 1991, 57, 1–7. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Natić, M.M.; Dabić, D.Č.; Papetti, A.; Fotirić, M.M.; Ognjanov, A.V.; Ljubojević, M.; Tešić, Ž.L. Analysis and characterisation of phytochemicals in mulberry (Morus alba L.) fruits grown in Vojvodina, North Serbia. Food Chem. 2015, 171, 128–136. [Google Scholar] [CrossRef] [PubMed]
- Metrouh-Amir, H.; Duarte, C.M.M.; Maiza, F. Solvent effect on total phenolic contents, antioxidant, and antibacterial activities of Matricaria pubescens. Ind. Crops Prod. 2015, 67, 249–256. [Google Scholar] [CrossRef]
- Quettier-Deleu, C.; Gressier, B.; Vasseur, J.; Dine, T.; Brunet, C.; Luyckx, M.; Cazin, M.; Cazin, J.C.; Bailleul, F.; Trotin, F. Phenolic compounds and antioxidant activities of buckwheat (Fagopyrum esculentum Moench) hulls and flour. J. Ethnopharmacol. 2000, 72, 35–42. [Google Scholar] [CrossRef]
- Zhao, C.-F.; Lei, D.J.; Hao Song, G.; Zhang, H.; Xu, H.; Yu, L.J. Characterisation of water-soluble proanthocyanidins of Pyracantha fortuneana fruit and their improvement in cell bioavailable antioxidant activity of quercetin. Food Chem. 2015, 169, 484–491. [Google Scholar] [CrossRef] [PubMed]
Extract | Extraction Method | % Extraction Yield (w/w Dry Bark) † |
---|---|---|
Quercus crassifolia | Hot water | 20.0 ± 7.7 a * |
Purified Quercus crassifolia | Hot water | 2.7 ± 0.3 |
Quercus crassifolia | Maceration | 11.0 ± 1.0 b,c |
Quercus laurina | Hot water | 14.2 ± 0.2 b |
Quercus laurina | Maceration | 13.6 ± 0.1 b |
Quercus scytophylla | Hot water | 6.8 ± 1.9 c,d |
Quercus scytophylla | Maceration | 4.4 ± 0.2 d |
Extract | Total Phenols (mg GAE/g) | Total Flavonoids (mg QE/g) | Hydroxycinnamic Acids (mg ChAE/g) | Proanthocyanidins (mg CChE/g) |
---|---|---|---|---|
Q. crassifolia hot water | 747 ± 41 a | 25.4 ± 0.6 a | 235 ± 2 c | 25.7 ± 1.3 d * |
Purified Q. crassifolia hot water | 860 ± 6 * | 43.6 ± 0.3 * | 362 ± 13 * | 9.4 ± 0.3 |
Q. crassifolia maceration | 695 ± 62 a | 14.0 ± 0.3 d | 269 ± 37 b | 53.5 ± 1.0 b |
Q. laurina hot water | 474 ± 44 b | 24.1 ± 1.1 b | 133 ± 4 e,f | 14.2 ± 0.4 e |
Q. laurina maceration | 756 ± 17 a | 15.7 ± 0.2 e | 145 ± 17 e,f | 24.3 ± 1.8 d |
Q. scytophylla hot water | 329 ± 38 c | 24.1 ± 0.5 b | 113 ± 3 e,f | 12.6 ± 2.3 e |
Q. scytophylla maceration | 521 ± 40 b | 12.9 ± 0.3 c | 173 ± 13 d,e | 48.4 ± 3.8 c |
Oligopin® | 736 ± 20 a | 6.4 ± 0.2 f | 337 ± 28 a | 69.2 ± 0.8 a |
Extract | OH• EC50 (µg/mL) | O2•− EC50 (µg/mL) | ROO• EC50 (µg/mL) | H2O2 EC50 (µg/mL) | NO• EC50 (µg/mL) | HClO EC50 (µg/mL) |
---|---|---|---|---|---|---|
Q. crassifolia hot water | 918 ± 9 c * | 80.5 ± 0.7 e * | 577 ± 40 c | 597 ± 162 b * | >4000 a * | 740 ± 54 b * |
Purified Q. crassifolia hot water | 467 ± 50 | 58.1 ± 1.6 | 717 ± 9 * | 22.0 ± 1.8 | >4000 * | 108 ± 25 |
Q. crassifolia maceration | 2024 ± 198 b | 40.9 ± 16.4 e | 1747 ± 87 a | 653 ± 122 b | 873 ± 49 b | 1276 ± 40 a |
Q. laurina hot water | 1257 ± 75 c | 629 ± 9 c | 582 ± 15 c | 727 ± 57 b | >4000 a | 774 ± 192 b |
Q. laurina maceration | >4000 a | 3213 ± 917 b | 622 ± 48 c | 519 ± 116 b | 149 ± 17 d | 387 ± 86 c |
Q. scytophylla hot water | 1865 ± 396 b | > 4000 a | 390 ± 160 d | 1102 ± 49 a | >4000 a | 866 ± 183 b |
Q. scytophylla maceration | >4000 a | 406 ± 135 d | 856 ± 24 b | 1050 ± 166 a | 661 ± 177 c | 953 ± 212 b |
Oligopin® | 1271 ± 72 c | 104 ± 8 e | 563 ± 33 c | 174 ± 10 c | >4000 a | 1310 ± 114 a |
Terana® turmeric | 53.8 ± 39.0 d |
ROO• | O2•− | OH• | H2O2 | NO• | HClO | |
---|---|---|---|---|---|---|
Total phenols | 0.298 | −0.567 * | −0.441 * | −0.821 * | −0.070 | −0.411 |
Total flavonoids | −0.005 | −0.223 | −0.631 * | −0.119 | 0.511 * | −0.532 * |
Total hydroxycinnamic acids | 0.403 | −0.829 * | −0.545 * | −0.835 * | 0.186 | 0.023 |
Proanthocyanidins | −0.261 | −0.245 | 0.324 | −0.056 | −0.331 | 0.687 * |
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Valencia-Avilés, E.; García-Pérez, M.E.; Garnica-Romo, M.G.; Figueroa-Cárdenas, J.D.D.; Meléndez-Herrera, E.; Salgado-Garciglia, R.; Martínez-Flores, H.E. Antioxidant Properties of Polyphenolic Extracts from Quercus Laurina, Quercus Crassifolia, and Quercus Scytophylla Bark. Antioxidants 2018, 7, 81. https://doi.org/10.3390/antiox7070081
Valencia-Avilés E, García-Pérez ME, Garnica-Romo MG, Figueroa-Cárdenas JDD, Meléndez-Herrera E, Salgado-Garciglia R, Martínez-Flores HE. Antioxidant Properties of Polyphenolic Extracts from Quercus Laurina, Quercus Crassifolia, and Quercus Scytophylla Bark. Antioxidants. 2018; 7(7):81. https://doi.org/10.3390/antiox7070081
Chicago/Turabian StyleValencia-Avilés, Eréndira, Martha Estrella García-Pérez, Ma. Guadalupe Garnica-Romo, Juan De Dios Figueroa-Cárdenas, Esperanza Meléndez-Herrera, Rafael Salgado-Garciglia, and Héctor E. Martínez-Flores. 2018. "Antioxidant Properties of Polyphenolic Extracts from Quercus Laurina, Quercus Crassifolia, and Quercus Scytophylla Bark" Antioxidants 7, no. 7: 81. https://doi.org/10.3390/antiox7070081