Comparison of Polysaccharides as Coatings for Quercetin-Loaded Liposomes (QLL) and Their Effect as Antioxidants on Radical Scavenging Activity
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials
2.2. Quercetin-Loaded Liposomes (QLL) Preparation
2.3. Chitosan Coated Liposomes
2.4. Polysaccharide Coated Liposomes
2.5. Liposomes Characterization
2.5.1. Particle Size Distribution
2.5.2. Morphology and Microstructure
2.6. Radical Scavenging Activity
2.7. Statistical Analysis
3. Results and Discussion
3.1. Particle Size Distribution
3.2. Particle Morphology
3.3. Particle Microstructure
3.4. Radical Scavenging Activity
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
- Eça, K.S.; Sartori, T.; Menegalli, F.C. Films and edible coatings containing antioxidants—A review. Braz. J. Food Technol. 2014, 17, 98–112. [Google Scholar]
- Lorenzo, J.M.; Pateiro, M.; Fontán, M.C.G.; Carballo, J. Effect of fat content on physical, microbial, lipid and protein changes during chill storage of foal liver pâté. Food Chem. 2014, 155, 57–63. [Google Scholar] [CrossRef] [PubMed]
- Sánchez-Ortega, I.; García-Almendárez, B.E.; Santos-López, E.M.; Amaro-Reyes, A.; Barboza-Corona, J.E.; Regalado, C. Antimicrobial Edible Films and Coatings for Meat and Meat Products Preservation. Sci. World J. 2014, 2014, 248935. [Google Scholar]
- Lobo, V.; Patil, A.; Phatak, A.; Chandra, N. Free radicals, antioxidants and functional foods: Impact on human health. Pharmacogn. Rev. 2010, 4, 118–126. [Google Scholar] [CrossRef] [Green Version]
- Lorenzo, J.M.; Pateiro, M.; Domínguez, R.; Barba, F.J.; Putnik, P.; Kovačević, D.B.; Shpigelman, A.; Granato, D.; Franco, D. Berries extracts as natural antioxidants in meat products: A review. Food Res. Int. 2018, 106, 1095–1104. [Google Scholar] [CrossRef]
- Przybylski, R.; Firdaous, L.; Châtaigné, G.; Dhulster, P.; Nedjar, N. Production of an antimicrobial peptide derived from slaughterhouse by-product and its potential application on meat as preservative. Food Chem. 2016, 211, 306–313. [Google Scholar] [CrossRef]
- Sanz, S.; Olarte, C.; Ayala, F.; Echávarri, J.F. Evolution of Quality Characteristics of Minimally Processed Asparagus During Storage in Different Lighting Conditions. J. Food Sci. 2009, 74, S296–S302. [Google Scholar] [CrossRef]
- Takahashi, O. Haemorrhages due to defective blood coagulation do not occur in mice and guinea-pigs fed butylated hydroxytoluene, but nephrotoxicity is found in mice. Food Chem. Toxicol. 1992, 30, 89–97. [Google Scholar] [CrossRef]
- Wang, W.; Kannan, P.; Xue, J.; Kannan, K. Synthetic phenolic antioxidants, including butylated hydroxytoluene (BHT), in resin-based dental sealants. Environ. Res. 2016, 151, 339–343. [Google Scholar] [CrossRef]
- Özcan, M.M.; Arslan, D. Antioxidant effect of essential oils of rosemary, clove and cinnamon on hazelnut and poppy oils. Food Chem. 2011, 129, 171–174. [Google Scholar] [CrossRef]
- Singh, G.; Maurya, S.; deLampasona, M.P.; Catalan, C.A.N. A comparison of chemical, antioxidant and antimicrobial studies of cinnamon leaf and bark volatile oils, oleoresins and their constituents. Food Chem. Toxicol. 2007, 45, 1650–1661. [Google Scholar] [CrossRef]
- Samoticha, J.; Jara-Palacios, M.J.; Hernández-Hierro, J.M.; Heredia, F.J.; Wojdyło, A. Phenolic compounds and antioxidant activity of twelve grape cultivars measured by chemical and electrochemical methods. Eur. Food Res. Technol. 2018, 244, 1933–1943. [Google Scholar] [CrossRef]
- Oroian, M.; Escriche, I. Antioxidants: Characterization, natural sources, extraction and analysis. Food Res. Int. 2015, 74, 10–36. [Google Scholar] [CrossRef] [PubMed]
- Russo, M.; Spagnuolo, C.; Tedesco, I.; Bilotto, S.; Russo, G.L. The flavonoid quercetin in disease prevention and therapy: Facts and fancies. Biochem. Pharmacol. 2012, 83, 6–15. [Google Scholar] [CrossRef] [PubMed]
- Althans, D.; Schrader, P.; Enders, S. Solubilisation of quercetin: Comparison of hyperbranched polymer and hydrogel. J. Mol. Liq. 2014, 196, 86–93. [Google Scholar] [CrossRef]
- Basu, A.; Kundu, S.; Sana, S.; Halder, A.; Abdullah, M.F.; Datta, S.; Mukherjee, A. Edible nano-bio-composite film cargo device for food packaging applications. Food Packag. Shelf Life 2017, 11, 98–105. [Google Scholar] [CrossRef]
- Scalia, S.; Mezzena, M. Incorporation of quercetin in lipid microparticles: Effect on photo- and chemical-stability. J. Pharm. Biomed. Anal. 2009, 49, 90–94. [Google Scholar] [CrossRef] [PubMed]
- Frenzel, M.; Steffen-Heins, A. Impact of quercetin and fish oil encapsulation on bilayer membrane and oxidation stability of liposomes. Food Chem. 2015, 185, 48–57. [Google Scholar] [CrossRef]
- Das, S.S.; Hussain, A.; Verma, P.R.P.; Imam, S.S.; Altamimi, M.A.; Alshehri, S.; Singh, S.K. Recent Advances in Liposomal Drug Delivery System of Quercetin for Cancer Targeting: A Mechanistic Approach. Curr. Drug Deliv. 2020, 17, 845–860. [Google Scholar] [CrossRef]
- Grit, M.; Crommelin, D.J.A. Chemical stability of liposomes: Implications for their physical stability. Chem. Phys. Lipids 1993, 64, 3–18. [Google Scholar] [CrossRef]
- Aditya, N.P.; Macedo, A.S.; Doktorovova, S.; Souto, E.B.; Kim, S.; Chang, P.-S.; Ko, S. Development and evaluation of lipid nanocarriers for quercetin delivery: A comparative study of solid lipid nanoparticles (SLN), nanostructured lipid carriers (NLC), and lipid nanoemulsions (LNE). LWT 2014, 59, 115–121. [Google Scholar] [CrossRef]
- Frenzel, M.; Steffen-Heins, A. Whey protein coating increases bilayer rigidity and stability of liposomes in food-like matrices. Food Chem. 2015, 173, 1090–1099. [Google Scholar] [CrossRef] [PubMed]
- Hao, J.; Guo, B.; Yu, S.; Zhang, W.; Zhang, D.; Wang, J.; Wang, Y. Encapsulation of the flavonoid quercetin with chitosan-coated nano-liposomes. LWT 2017, 85, 37–44. [Google Scholar] [CrossRef]
- Lopes, N.A.; Barreto Pinilla, C.M.; Brandelli, A. Antimicrobial activity of lysozyme-nisin co-encapsulated in liposomes coated with polysaccharides. Food Hydrocoll. 2019, 93, 1–9. [Google Scholar] [CrossRef]
- Lopes, N.A.; Pinilla, C.M.B.; Brandelli, A. Pectin and polygalacturonic acid-coated liposomes as novel delivery system for nisin: Preparation, characterization and release behavior. Food Hydrocoll. 2017, 70, 1–7. [Google Scholar] [CrossRef]
- Samadikhah, H.R.; Majidi, A.; Nikkhah, M.; Hosseinkhani, S. Preparation, characterization, and efficient transfection of cationic liposomes and nanomagnetic cationic liposomes. Int. J. Nanomed. 2011, 6, 2275–2283. [Google Scholar]
- Tai, K.; Rappolt, M.; Mao, L.; Gao, Y.; Li, X.; Yuan, F. The stabilization and release performances of curcumin-loaded liposomes coated by high and low molecular weight chitosan. Food Hydrocoll. 2020, 99, 105355. [Google Scholar] [CrossRef]
- Tan, C.; Feng, B.; Zhang, X.; Xia, W.; Xia, S. Biopolymer-coated liposomes by electrostatic adsorption of chitosan (chitosomes) as novel delivery systems for carotenoids. Food Hydrocoll. 2016, 52, 774–784. [Google Scholar] [CrossRef]
- Hasan, M.; Ben Messaoud, G.; Michaux, F.; Tamayol, A.; Kahn, C.J.F.; Belhaj, N.; Linder, M.; Arab-Tehrany, E. Chitosan-coated liposomes encapsulating curcumin: Study of lipid–polysaccharide interactions and nanovesicle behavior. RSC Adv. 2016, 6, 45290–45304. [Google Scholar] [CrossRef]
- Ramezanzade, L.; Hosseini, S.F.; Nikkhah, M. Biopolymer-coated nanoliposomes as carriers of rainbow trout skin-derived antioxidant peptides. Food Chem. 2017, 234, 220–229. [Google Scholar] [CrossRef]
- De Leo, V.; Milano, F.; Mancini, E.; Comparelli, R.; Giotta, L.; Nacci, A.; Longobardi, F.; Garbetta, A.; Agostiano, A.; Catucci, L. Encapsulation of Curcumin-Loaded Liposomes for Colonic Drug Delivery in a pH-Responsive Polymer Cluster Using a pH-Driven and Organic Solvent-Free Process. Molecules 2018, 23, 739. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Kang, E.-C.; Aklyoshi, K.; Sunamoto, J. Surface Coating of Liposomes with Hydrophobized Polysaccharides. J. Bioact. Compat. Polym. 1997, 12, 14–26. [Google Scholar] [CrossRef]
- Sunamoto, J.; Iwamoto, K.; Takada, M.; Yuzuriha, T.; Katayama, K. Improved Drug Delivery to Target Specific Organs Using Liposomes as Coated with Polysaccharides. In Polymers in Medicine: Biomedical and Pharmacological Applications; Chiellini, E., Giusti, P., Eds.; Springer US: Boston, MA, USA, 1983. [Google Scholar]
- Betker, J.L.; Anchordoquy, T.J. The Use of Lactose as an Alternative Coating for Nanoparticles. J. Pharm. Sci. 2020, 109, 1573–1580. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Iwabuchi, K.; Masuda, H.; Kaga, N.; Nakayama, H.; Matsumoto, R.; Iwahara, C.; Yoshizaki, F.; Tamaki, Y.; Kobayashi, T.; Hayakawa, T.; et al. Properties and functions of lactosylceramide from mouse neutrophils. Glycobiology 2015, 25, 655–668. [Google Scholar] [CrossRef] [PubMed]
- Araujo-Díaz, S.B.; Leyva-Porras, C.; Aguirre-Bañuelos, P.; Álvarez-Salas, C.; Saavedra-Leos, Z. Evaluation of the physical properties and conservation of the antioxidants content, employing inulin and maltodextrin in the spray drying of blueberry juice. Carbohydr. Polym. 2017, 167, 317–325. [Google Scholar] [CrossRef]
- Guldiken, B.; Linke, A.; Capanoglu, E.; Boyacioglu, D.; Kohlus, R.; Weiss, J.; Gibis, M. Formation and characterization of spray dried coated and uncoated liposomes with encapsulated black carrot extract. J. Food Eng. 2019, 246, 42–50. [Google Scholar] [CrossRef]
- Derksen, J.T.P.; Morselt, H.W.M.; Scherphof, G.L. Processing of different liposome markers after in vitro uptake of immunoglobulin-coated liposomes by rat liver macrophages. Biochim. Biophys. Acta Mol. Cell Res. 1987, 931, 33–40. [Google Scholar] [CrossRef]
- Takada, M.; Yuzuriha, T.; Katayama, K.; Iwamoto, K.; Sunamoto, J. Increased lung uptake of liposomes coated with polysaccharides. Biochim. Biophys. Acta Gen. Subj. 1984, 802, 237–244. [Google Scholar] [CrossRef]
- Park, S.N.; Jo, N.R.; Jeon, S.H. Chitosan-coated liposomes for enhanced skin permeation of resveratrol. J. Ind. Eng. Chem. 2014, 20, 1481–1485. [Google Scholar] [CrossRef]
- Vural, I.; Sarisozen, C.; Olmez, S.S. Chitosan Coated Furosemide Liposomes for Improved Bioavailability. J. Biomed. Nanotechnol. 2011, 7, 426–430. [Google Scholar] [CrossRef]
- Li, Z.; Paulson, A.T.; Gill, T.A. Encapsulation of bioactive salmon protein hydrolysates with chitosan-coated liposomes. J. Funct. Foods 2015, 19, 733–743. [Google Scholar] [CrossRef]
- Romero-Pérez, A.; García-García, E.; Zavaleta-Mancera, A.; Ramírez-Bribiesca, J.E.; Revilla-Vázquez, A.; Hernández-Calva, L.M.; López-Arellano, R.; Cruz-Monterrosa, R.G. Designing and evaluation of sodium selenite nanoparticles in vitro to improve selenium absorption in ruminants. Vet. Res. Commun. 2010, 34, 71–79. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Barea, M.J.; Jenkins, M.J.; Lee, Y.S.; Johnson, P.; Bridson, R.H. Encapsulation of Liposomes within pH Responsive Microspheres for Oral Colonic Drug Delivery. Int. J. Biomater. 2012, 2012, 458712. [Google Scholar] [CrossRef] [PubMed]
- Caddeo, C.; Díez-Sales, O.; Pons, R.; Carbone, C.; Ennas, G.; Puglisi, G.; Fadda, A.M.; Manconi, M. Cross-linked chitosan/liposome hybrid system for the intestinal delivery of quercetin. J. Colloid Interface Sci. 2016, 461, 69–78. [Google Scholar] [CrossRef] [Green Version]
- Tan, C.; Zhang, Y.; Abbas, S.; Feng, B.; Zhang, X.; Xia, S. Modulation of the carotenoid bioaccessibility through liposomal encapsulation. Colloids Surf. B Biointerfaces 2014, 123, 692–700. [Google Scholar] [CrossRef]
- Zhou, W.; Liu, W.; Zou, L.; Liu, W.; Liu, C.; Liang, R.; Chen, J. Storage stability and skin permeation of vitamin C liposomes improved by pectin coating. Colloids Surf. B Biointerfaces 2014, 117, 330–337. [Google Scholar] [CrossRef]
- Belhaj, N.; Arab-Tehrany, E.; Loing, E.; Bézivin, C. Skin delivery of hydrophilic molecules from liposomes and polysaccharide-coated liposomes. Int. J. Cosmet. Sci. 2017, 39, 435–441. [Google Scholar] [CrossRef]
- Aguiar, J.; Costa, R.; Rocha, F.; Estevinho, B.N.; Santos, L. Design of microparticles containing natural antioxidants: Preparation, characterization and controlled release studies. Powder Technol. 2017, 313, 287–292. [Google Scholar] [CrossRef]
- Henriksen, I.; Smistad, G.; Karlsen, J. Interactions between liposomes and chitosan. Int. J. Pharm. 1994, 101, 227–236. [Google Scholar] [CrossRef]
- Celli, G.B.; Ghanem, A.; Brooks, M.S.-L. Bioactive Encapsulated Powders for Functional Foods—A Review of Methods and Current Limitations. Food Bioprocess Technol. 2015, 8, 1825–1837. [Google Scholar] [CrossRef]
- Zhao, G.D.; Sun, R.; Ni, S.L.; Xia, Q. Development and characterisation of a novel chitosan-coated antioxidant liposome containing both coenzyme Q10 and alpha-lipoic acid. J. Microencapsul. 2015, 32, 157–165. [Google Scholar] [CrossRef] [PubMed]
- Caddeo, C.; Gabriele, M.; Fernàndez-Busquets, X.; Valenti, D.; Fadda, A.M.; Pucci, L.; Manconi, M. Antioxidant activity of quercetin in Eudragit-coated liposomes for intestinal delivery. Int. J. Pharm. 2019, 565, 64–69. [Google Scholar] [CrossRef]
- Takeuchi, H.; Kojima, H.; Yamamoto, H.; Kawashima, Y. Evaluation of circulation profiles of liposomes coated with hydrophilic polymers having different molecular weights in rats. J. Control. Release 2001, 75, 83–91. [Google Scholar] [CrossRef]
- Desiraju, G.R.; Steiner, T. The Weak Hydrogen Bond: In Structural Chemistry and Biology; Oxford University Press/International Union of Crystallography: Oxford, UK, 2001; Volume 9. [Google Scholar]
- Leyva-Porras, C.; Saavedra–Leos, M.Z.; López-Pablos, A.L.; Soto-Guerrero, J.J.; Toxqui-Terán, A.; Fozado-Quiroz, R.E. Chemical, Thermal and Physical Characterization of Inulin for its Technological Application Based on the Degree of Polymerization. J. Food Process Eng. 2017, 40, e12333. [Google Scholar] [CrossRef]
- Saavedra-Leos, M.Z.; Leyva-Porras, C.; López-Martínez, L.A.; González-García, R.; Martínez, J.O.; Compeán Martínez, I.; Toxqui-Terán, A. Evaluation of the Spray Drying Conditions of Blueberry Juice-Maltodextrin on the Yield, Content, and Retention of Quercetin 3-d-Galactoside. Polymers 2019, 11, 312. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Leyva-Porras, C.; Saavedra-Leos, M.Z.; Cervantes-González, E.; Aguirre-Bañuelos, P.; Silva-Cázarez, M.B.; Álvarez-Salas, C. Spray drying of blueberry juice-maltodextrin mixtures: Evaluation of processing conditions on content of resveratrol. Antioxidants 2019, 8, 437. [Google Scholar] [CrossRef] [PubMed] [Green Version]
Sample Name | Coating | Quercetin Loaded |
---|---|---|
CL | Uncoated | No |
ICCL | Inulin | No |
LCCL | Lactose | No |
CCCL | Chitosan | No |
QLL | Uncoated | Yes |
ICQLL | Inulin | Yes |
LCQLL | Lactose | Yes |
CCQLL | Chitosan | Yes |
Sample | Scavenging Activity (%) | ||
---|---|---|---|
15 µg/mL | 5 µg/mL | 2.5 µg/mL | |
QLL | 85.95 | 44.54 | 23.53 |
ICQLL | 9.06 | 1.78 | 0.71 |
LCQLL | 58.90 | 17.73 | 10.08 |
CCQLL | 27.83 | 10.93 | 4.85 |
CL | ---- | ---- | ---- |
ICCL | ---- | ---- | ---- |
LCCL | ---- | ---- | ---- |
CCCL | ---- | ---- | ---- |
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Román-Aguirre, M.; Leyva-Porras, C.; Cruz-Alcantar, P.; Aguilar-Elguézabal, A.; Saavedra-Leos, M.Z. Comparison of Polysaccharides as Coatings for Quercetin-Loaded Liposomes (QLL) and Their Effect as Antioxidants on Radical Scavenging Activity. Polymers 2020, 12, 2793. https://doi.org/10.3390/polym12122793
Román-Aguirre M, Leyva-Porras C, Cruz-Alcantar P, Aguilar-Elguézabal A, Saavedra-Leos MZ. Comparison of Polysaccharides as Coatings for Quercetin-Loaded Liposomes (QLL) and Their Effect as Antioxidants on Radical Scavenging Activity. Polymers. 2020; 12(12):2793. https://doi.org/10.3390/polym12122793
Chicago/Turabian StyleRomán-Aguirre, Manuel, César Leyva-Porras, Pedro Cruz-Alcantar, Alfredo Aguilar-Elguézabal, and María Zenaida Saavedra-Leos. 2020. "Comparison of Polysaccharides as Coatings for Quercetin-Loaded Liposomes (QLL) and Their Effect as Antioxidants on Radical Scavenging Activity" Polymers 12, no. 12: 2793. https://doi.org/10.3390/polym12122793