Enzymatic Treatment of Ferulated Arabinoxylans from Distillers Dried Grains with Solubles: Influence on the Fabrication of Covalent Electro-Sprayed Nanoparticles
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials
2.2. Enzymatic Treatment of AXs
2.3. Phenolic Acid Analysis
2.4. Protein Analysis
2.5. Fourier Transform Infra-Red (FTIR) Spectroscopy
2.6. Macromolecular Characteristics
2.7. AX and AXPP Covalent Cross-Linking
2.8. Nanoparticles Fabrication
2.9. Dynamic Light Scattering (DLS) Analysis
2.10. Transmission Electron Microscopy (TEM) Analysis
2.11. Confocal Laser Scanning Microscopy (CLSM) Analysis
2.12. Statistical Analysis
3. Results and Discussion
3.1. AX and AXPP Characterization
3.2. AX and AXPP Covalent Cross-Linking
3.3. NAX and NAXPP Fabrication and Characteristics
3.4. CLSM Analysis of Gels and NAXs and NAXPPs
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
- Saulnier, L.; Guillon, F.; Sado, P.-E.; Chateigner-Boutin, A.-L.; Rouau, X. Plant Cell Wall Polysaccharides in Storage Organs: Xylans (Food Applications). In Reference Module in Chemistry, Molecular Sciences and Chemical Engineering; Elsevier: Amsterdam, The Netherlands, 2013; pp. 653–689. ISBN 978-0-12-409547-2. [Google Scholar]
- Izydorczyk, M.; Biliaderis, C.G.; Bushuk, W. Comparison of the structure and composition of water-soluble pentosans from different wheat varieties. Cereal Chem. 1991, 68, 139–144. [Google Scholar]
- Mendez-Encinas, M.A.; Carvajal-Millan, E.; Rascon-Chu, A.; Astiazaran-Garcia, H.F.; Valencia-Rivera, D.E. Ferulated Arabinoxylans and Their Gels: Functional Properties and Potential Application as Antioxidant and Anticancer Agent. Oxid. Med. Cell. Longev. 2018, 2018, 2314759. [Google Scholar] [CrossRef]
- Marquez-Escalante, J.A.; Carvajal-Millan, E. Feruloylated Arabinoxylans from Maize Distiller’s Dried Grains with Solubles: Effect of Feruloyl Esterase on their Macromolecular Characteristics, Gelling, and Antioxidant Properties. Sustainability 2019, 11, 6449. [Google Scholar] [CrossRef]
- Roth, M.; Jekle, M.; Becker, T. Opportunities for upcycling cereal byproducts with special focus on Distiller’s grains. Trends Food Sci. Technol. 2019, 91, 282–293. [Google Scholar] [CrossRef]
- Izydorczyk, M.S.; Biliaderis, C.G. Cereal arabinoxylans: Advances in structure and physicochemical properties. Carbohydr. Polym. 1995, 28, 33–48. [Google Scholar] [CrossRef]
- Morales-Ortega, A.; Niño-Medina, G.; Carvajal-Millán, E.; Gardea-Béjar, A.; Torres-Chávez, P.; López-Franco, Y.; Rascón-Chu, A.; Lizardi-Mendoza, J. Los Arabinoxilanos Ferulados De Cereales. Una Revisión De Sus. Rev. Fitotec. Mex. 2013, 36, 439–446. [Google Scholar]
- Saulnier, L.; Crépeau, M.J.; Lahaye, M.; Thibault, J.F.; Garcia-Conesa, M.T.; Kroon, P.A.; Williamson, G. Isolation and structural determination of two 5,5′-diferuloyl oligosaccharides indicate that maize heteroxylans are covalently cross-linked by oxidatively coupled ferulates. Carbohydr. Res. 1999, 320, 82–92. [Google Scholar] [CrossRef]
- Saulnier, L.; Marot, C.; Chanliaud, E.; Thibault, J.F. Cell wall polysaccharide interactions in maize bran. Carbohydr. Polym. 1995, 26, 279–287. [Google Scholar] [CrossRef]
- Carvajal-Millan, E.; Landillon, V.; Morel, M.-H.; Rouau, X.; Doublier, J.-L.; Micard, V. Arabinoxylan gels: Impact of the feruloylation degree on their structure and properties. Biomacromolecules 2005, 6, 309–317. [Google Scholar] [CrossRef]
- Martínez-López, A.L.; Carvajal-Millan, E.; Marquez-Escalante, J.; Campa-Mada, A.C.; Rascón-Chu, A.; López-Franco, Y.L.; Lizardi-Mendoza, J. Enzymatic cross-linking of ferulated arabinoxylan: Effect of laccase or peroxidase catalysis on the gel characteristics. Food Sci. Biotechnol. 2019, 28, 311–318. [Google Scholar] [CrossRef]
- Carvajal-Millan, E.; Rascón-Chu, A.; Márquez-Escalante, J.A.; Micard, V.; de León, N.P.; Gardea, A. Maize bran gum: Extraction, characterization and functional properties. Carbohydr. Polym. 2007, 69, 280–285. [Google Scholar] [CrossRef]
- Mendez-Encinas, M.A.; Carvajal-Millan, E.; Yadav, M.P.; López-Franco, Y.L.; Rascon-Chu, A.; Lizardi-Mendoza, J.; Brown-Bojorquez, F.; Silva-Campa, E.; Pedroza-Montero, M. Partial removal of protein associated with arabinoxylans: Impact on the viscoelasticity, crosslinking content, and microstructure of the gels formed. J. Appl. Polym. Sci. 2019, 136, 47300. [Google Scholar] [CrossRef]
- Yadav, M.P.; Fishman, M.L.; Chau, H.K.; Johnston, D.B.; Hicks, K.B. Molecular Characteristics of Corn Fiber Gum and Their Influence on CFG Emulsifying Properties. Cereal Chem. J. 2007, 84, 175–180. [Google Scholar] [CrossRef]
- Yadav, M.P.; Nuñez, A.; Hicks, K.B. Isolation, Purification, and Identification of Protein Associated with Corn Fiber Gum. J. Agric. Food Chem. 2011, 59, 13289–13294. [Google Scholar] [CrossRef]
- Fincher, G.; Stone, B. A Water-soluble Arabinogalactan-Peptide From Wheat Endosperm. Aust. J. Biol. Sci. 1974, 27, 117–132. [Google Scholar] [CrossRef]
- Yadav, M.P.; Cooke, P.; Johnston, D.B.; Hicks, K.B. Importance of Protein-Rich Components in Emulsifying Properties of Corn Fiber Gum. Cereal Chem. J. 2010, 87, 89–94. [Google Scholar] [CrossRef]
- Rudjito, R.C.; Ruthes, A.C.; Jiménez-Quero, A.; Vilaplana, F. Feruloylated arabinoxylans from wheat bran: Optimization of extraction process and validation at pilot scale. ACS Sustain. Chem. Eng. 2019, 7, 13167–13177. [Google Scholar] [CrossRef]
- Paesani, C.; Degano, A.L.; Ines, Z.; Zalosnik, M.I.; Fabi, J.P.; Pérez, G.T. Enzymatic modification of arabinoxylans from soft and hard Argentinian wheat inhibits the viability of HCT-116 cells. Food Res. Int. 2021, 147, 110466. [Google Scholar] [CrossRef]
- Tavano, O.L.; Berenguer-Murcia, A.; Secundo, F.; Fernandez-Lafuente, R. Biotechnological Applications of Proteases in Food Technology. Compr. Rev. Food Sci. Food Saf. 2018, 17, 412–436. [Google Scholar] [CrossRef]
- Méndez-Encinas, M.; Carvajal-Millan, E.; Yadav, M.; Valenzuela-Soto, E.M.; Figueroa-Soto, C.G.; Tortoledo-Ortiz, O.; García-Sánchez, G. Gels of ferulated arabinoxylans: Rheology, structural parameters and microstructure. In Advances in Physicochemical Properties of Biopolymers; Bentham Science Publishers: Beijing, China, 2017; pp. 208–221. [Google Scholar]
- Méndez-Encinas, M.; Carvajal-Millan, E.; Rascón-Chu, A.; López-Franco, Y.; Lizardi, J. Arabinoxilanos y la Relación de la Fracción Proteica Remanente con la Capacidad Gelificante del Polisacárido. Acta Univ. 2019, 29, e1755. [Google Scholar] [CrossRef]
- González-Estrada, R.; Calderón-Santoyo, M.; Carvajal-Millan, E.; De Jesús Ascencio Valle, F.; Ragazzo-Sánchez, J.A.; Brown-Bojorquez, F.; Rascón-Chu, A. Covalently cross-linked arabinoxylans films for Debaryomyces hansenii entrapment. Molecules 2015, 20, 11373–11386. [Google Scholar] [CrossRef]
- Paz-Samaniego, R.; Rascón-Chu, A.; Brown-Bojorquez, F.; Carvajal-Millan, E.; Pedroza-Montero, M.; Silva-Campa, E.; Sotelo-Cruz, N.; López-Franco, Y.L.; Lizardi-Mendoza, J. Electrospray-assisted fabrication of core-shell arabinoxylan gel particles for insulin and probiotics entrapment. J. Appl. Polym. Sci. 2018, 135, 46411. [Google Scholar] [CrossRef]
- Morales-Burgos, A.M.; Carvajal-Millan, E.; Rascón-Chu, A.; Martínez-López, A.L.; Lizardi-Mendoza, J.; López-Franco, Y.L.; Brown-Bojorquez, F. Tailoring reversible insulin aggregates loaded in electrosprayed arabinoxylan microspheres intended for colon-targeted delivery. J. Appl. Polym. Sci. 2019, 136, 47960. [Google Scholar] [CrossRef]
- Ohlmaier-Delgadillo, F.; Carvajal-Millan, E.; López-Franco, Y.L.; Islas-Osuna, M.A.; Micard, V.; Antoine-Assor, C.; Rascón-Chu, A. Ferulated Pectins and Ferulated Arabinoxylans Mixed Gel for Saccharomyces boulardii Entrapment in Electrosprayed Microbeads. Molecules 2021, 26, 2478. [Google Scholar] [CrossRef]
- Seidi, F.; Jenjob, R.; Phakkeeree, T.; Crespy, D. Saccharides, oligosaccharides, and polysaccharides nanoparticles for biomedical applications. J. Control. Release 2018, 284, 188–212. [Google Scholar] [CrossRef] [PubMed]
- Jacob, J.; Haponiuk, J.T.; Thomas, S.; Gopi, S. Biopolymer based nanomaterials in drug delivery systems: A review. Mater. Today Chem. 2018, 9, 43–55. [Google Scholar] [CrossRef]
- De Anda-Flores, Y.; Carvajal-Millan, E.; Lizardi-Mendoza, J.; Rascon-Chu, A.; Martínez-López, A.L.; Marquez-Escalante, J.; Brown-Bojorquez, F.; Tanori-Cordova, J. Covalently Cross-Linked Nanoparticles Based on Ferulated Arabinoxylans Recovered from a Distiller’s Dried Grains Byproduct. Processes 2020, 8, 691. [Google Scholar] [CrossRef]
- De Anda-Flores, Y.; Carvajal-Millan, E.; Lizardi-Mendoza, J.; Rascon-Chu, A.; Tanori-Cordova, J.; Martínez-López, A.L.; Burgara-Estrella, A.J.; Pedroza-Montero, M.R. Conformational Behavior, Topographical Features, and Antioxidant Activity of Partly De-Esterified Arabinoxylans. Polymers 2021, 13, 2794. [Google Scholar] [CrossRef]
- Vansteenkiste, E.; Babot, C.; Rouau, X.; Micard, V. Oxidative gelation of feruloylated arabinoxylan as affected by protein. Influence on protein enzymatic hydrolysis. Food Hydrocoll. 2004, 18, 557–564. [Google Scholar] [CrossRef]
- Bradford, M.M.; Pedroche, J.; Yust, M.M.; Girón-Calle, J.; Alaiz, M.; Millán, F.; Vioque, J. A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding. Anal. Biochem. 1976, 72, 248–254. [Google Scholar] [CrossRef]
- Dervilly-Pinel, G.; Thibault, J.-F.; Saulnier, L. Experimental evidence for a semi-flexible conformation for arabinoxylans. Carbohydr. Res. 2001, 330, 365–372. [Google Scholar] [CrossRef]
- Rascón-Chu, A.; Díaz-Baca, J.A.; Carvajal-Millan, E.; Pérez-López, E.; Hotchkiss, A.T.; González-Ríos, H.; Balandrán-Quintana, R.; Campa-Mada, A.C. Electrosprayed core-shell composite microbeads based on pectin-arabinoxylans for insulin carrying: Aggregation and size dispersion control. Polymers 2018, 10, 108. [Google Scholar] [CrossRef]
- Rochín-Wong, S.; Rosas-Durazo, A.; Zavala-Rivera, P.; Maldonado, A.; Martínez-Barbosa, M.; Vélaz, I.; Tánori, J. Drug Release Properties of Diflunisal from Layer-By-Layer Self-Assembled κ-Carrageenan/Chitosan Nanocapsules: Effect of Deposited Layers. Polymers 2018, 10, 760. [Google Scholar] [CrossRef]
- Keeratiburana, T.; Hansen, A.R.; Soontaranon, S.; Blennow, A.; Tongta, S. Porous high amylose rice starch modified by amyloglucosidase and maltogenic α-amylase. Carbohydr. Polym. 2020, 230, 115611. [Google Scholar] [CrossRef]
- Al-Assaf, S.; Sakata, M.; McKenna, C.; Aoki, H.; Phillips, G.O. Molecular associations in acacia gums. Struct. Chem. 2009, 20, 325–336. [Google Scholar] [CrossRef]
- Iravani, S.; Fitchett, C.S.; Georget, D.M.R. Physical characterization of arabinoxylan powder and its hydrogel containing a methyl xanthine. Carbohydr. Polym. 2011, 85, 201–207. [Google Scholar] [CrossRef]
- Kačuráková, M.; Ebringerová, A.; Hirsch, J.; Hromádková, Z. Infrared study of arabinoxylans. J. Sci. Food Agric. 1994, 66, 423–427. [Google Scholar] [CrossRef]
- Kacuráková, M. FT-IR study of plant cell wall model compounds: Pectic polysaccharides and hemicelluloses. Carbohydr. Polym. 2000, 43, 195–203. [Google Scholar] [CrossRef]
- Morales-Ortega, A.; Carvajal-Millan, E.; López-Franco, Y.; Rascón-Chu, A.; Lizardi-Mendoza, J.; Torres-Chavez, P.; Campa-Mada, A. Characterization of Water Extractable Arabinoxylans from a Spring Wheat Flour: Rheological Properties and Microstructure. Molecules 2013, 18, 8417–8428. [Google Scholar] [CrossRef]
- Sárossy, Z.; Tenkanen, M.; Pitkänen, L.; Bjerre, A.-B.; Plackett, D. Extraction and chemical characterization of rye arabinoxylan and the effect of β-glucan on the mechanical and barrier properties of cast arabinoxylan films. Food Hydrocoll. 2013, 30, 206–216. [Google Scholar] [CrossRef]
- Sene, C.; McCann, M.C.; Wilson, R.H.; Grinter, R. Fourier-Transform Raman and Fourier-Transform Infrared Spectroscopy (An Investigation of Five Higher Plant Cell Walls and Their Components). Plant Physiol. 1994, 106, 1623–1631. [Google Scholar] [CrossRef] [PubMed]
- Robert, P.; Marquis, M.; Barron, C.; Guillon, F.; Saulnier, L. FT-IR investigation of cell wall polysaccharides from cereal grains. Arabinoxylan infrared assignment. J. Agric. Food Chem. 2005, 53, 7014–7018. [Google Scholar] [CrossRef] [PubMed]
- Mendez-Encinas, M.A.; Carvajal-Millan, E.; Rascón-Chu, A.; Astiazarán-García, H.; Valencia-Rivera, D.E.; Brown-Bojorquez, F.; Alday, E.; Velazquez, C. Arabinoxylan-Based Particles: In Vitro Antioxidant Capacity and Cytotoxicity on a Human Colon Cell Line. Medicina 2019, 55, 349. [Google Scholar] [CrossRef] [PubMed]
AX | AXPP | |
---|---|---|
Protein (% p/p) | 16 ± 0.05 a | 11 ± 0.12 b |
A/X ratio | 1.16 ± 0.08 a | 1.13 ± 0.01 a |
* Ferulic acid (FA) | 7.3 ± 0.2 a | 7.3 ± 0.2 a |
* Dimers of FA (di-FAs) | 0.212 ± 0.009 b | 0.32 ± 0.07 a |
* Trimers of FA (tri-FAs) | traces | 0.06 ± 0.02 |
+ Molecular weight (Mw) (kDA) | 661 | 420 |
+ Intrinsic viscosity [η] (mL/g) | 149 | 165 |
+ Polydispersity index (PI) (Mw/Mn) | 2.4 | 2.0 |
+ Radius of gyration RG (nm) | 40 | 37 |
+ Hydrodynamic radius Rh (nm) | 22.5 | 20.0 |
+ Characteristic ratio (C∞) | 14.2 | 18.6 |
+ q (nm) | 4.1 | 5.3 |
+ Mark–Houwink–Sakurada α | 0.536 | 0.607 |
+ Mark–Houwink–Sakurada K (mL/g) | 1.394 × 10−1 | 7.804 × 10−2 |
Gel | di-FA Structures | Total di-FAs | tri-FAs | di-FA/tri-FA Ratio | ||
---|---|---|---|---|---|---|
5-5′ | 8-O-4′ | 8-5′ | ||||
AX | 0.166 ± 0.027 a | 0.218 ± 0.036 a | 1.109 ± 0.162 a | 1.49 ± 0.22 a | 0.31 ± 0.05 a | 4.82 ± 0.04 a |
AXPP | 0.161 ± 0.004 a | 0.225 ± 0.007 a | 1.246 ± 0.027 a | 1.63 ± 0.04 a | 0.31 ± 0.02 a | 5.35 ± 0.50 a |
Parameter | NAX | NAXPP |
---|---|---|
Hydrodynamic diameter (nm) | 328 ± 25 a | 307 ± 46 a |
Z potential (mV) | −30 ± 0.7 a | −27 ± 0.7 b |
Disclaimer/Publisher’s Note: The statements, opinions and data contained in all publications are solely those of the individual author(s) and contributor(s) and not of MDPI and/or the editor(s). MDPI and/or the editor(s) disclaim responsibility for any injury to people or property resulting from any ideas, methods, instructions or products referred to in the content. |
© 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
De Anda-Flores, Y.; Lizardi-Mendoza, J.; Rascón-Chu, A.; Tanori-Cordova, J.; Martínez-López, A.L.; Carvajal-Millan, E. Enzymatic Treatment of Ferulated Arabinoxylans from Distillers Dried Grains with Solubles: Influence on the Fabrication of Covalent Electro-Sprayed Nanoparticles. Polysaccharides 2023, 4, 358-370. https://doi.org/10.3390/polysaccharides4040021
De Anda-Flores Y, Lizardi-Mendoza J, Rascón-Chu A, Tanori-Cordova J, Martínez-López AL, Carvajal-Millan E. Enzymatic Treatment of Ferulated Arabinoxylans from Distillers Dried Grains with Solubles: Influence on the Fabrication of Covalent Electro-Sprayed Nanoparticles. Polysaccharides. 2023; 4(4):358-370. https://doi.org/10.3390/polysaccharides4040021
Chicago/Turabian StyleDe Anda-Flores, Yubia, Jaime Lizardi-Mendoza, Agustín Rascón-Chu, Judith Tanori-Cordova, Ana Luisa Martínez-López, and Elizabeth Carvajal-Millan. 2023. "Enzymatic Treatment of Ferulated Arabinoxylans from Distillers Dried Grains with Solubles: Influence on the Fabrication of Covalent Electro-Sprayed Nanoparticles" Polysaccharides 4, no. 4: 358-370. https://doi.org/10.3390/polysaccharides4040021