Mechanism of selective hydrolysis of alginates under hydrothermal conditions

Taku Michael Aida; Yasuaki Kumagai; Smith Jr Richard Lee

doi:10.1016/j.jobab.2022.04.001

Volume 7 Issue 3

Jul. 2022

Turn off MathJax

Article Contents

Article Navigation > Journal of Bioresources and Bioproducts > 2022 > 7(3): 173-179

Taku Michael Aida, Yasuaki Kumagai, Smith Jr Richard Lee. Mechanism of selective hydrolysis of alginates under hydrothermal conditions[J]. Journal of Bioresources and Bioproducts, 2022, 7(3): 173-179. doi: 10.1016/j.jobab.2022.04.001

Citation:

Taku Michael Aida, Yasuaki Kumagai, Smith Jr Richard Lee. Mechanism of selective hydrolysis of alginates under hydrothermal conditions[J]. Journal of Bioresources and Bioproducts, 2022, 7(3): 173-179. doi: 10.1016/j.jobab.2022.04.001

Citation:

PDF( 1064 KB)

Mechanism of selective hydrolysis of alginates under hydrothermal conditions

doi: 10.1016/j.jobab.2022.04.001

a.
Department of Chemical Engineering, Faculty of Engineering, Fukuoka University, Nanakuma Jonan-ku, Fukuoka 814-0180, Japan
b.
Research Center of Composite Material, Fukuoka University, Nanakuma Jonan-ku, Fukuoka, 814-0180, Japan
c.
Graduate School of Environmental Studies, Tohoku University, Aoba-ku, Sendai, 980-8579, Japan

More Information

Corresponding author: E-mail address: aida@fukuoka-u.ac.jp (T.M. Aida)
Received Date: 2022-03-23
Accepted Date: 2022-04-23
Rev Recd Date: 2022-04-20

Available Online: 2022-05-04

Publish Date: 2022-07-31

Abstract

Abstract

Mechanisms of selective hydrolysis of alginates under hydrothermal conditions were investigated by comparing reactivities of sodium alginate (Na-ALG, 960 ku) solutions and calcium alginate (Ca-ALG) gels as substrates. Under hydrothermal conditions (150 ℃), hydrolysis of Na-ALG gave product molecular weights of 223, 66, 26 and 17 ku while those of Ca-ALG gave product molecular weights of 340, 102, 45 and 31 ku for reaction times of 10, 20, 30 and 60 min, respectively. The ratios of mannuronic acid (M) to guluronic acid (G) varied only slightly (from 1.3 to 1.2) for Na-ALG over the range of reaction times at 150 ℃, while ratios (M/G) for Ca-ALG exhibited a remarkable decrease (from 1.1 to 0.8). Diad sequence of alginate products obtained for Na-ALG were 17%, 23%, 27% and 31% (GG); 30%, 32%, 36% and 38% (MM); and 53%, 46%, 37% and 32% (GM+MG); while for Ca-ALG they were 18%, 22%, 24% and 33% (GG); 26%, 23%, 26% and 18% (MM); and 56%, 54%, 50% and 48% (GM+MG). Reaction mechanisms are proposed for hydrolysis of alginate solutions and alginate gels under hydrothermal conditions; de-polymerization of alginates into monomers and monomeric sequences can be controlled not only by hydrothermal conditions, but also by varying the physical state (solution, gel) of the starting materials.
- Biomaterial,
- Biopolymer,
- De-polymerization,
- High temperature water

FullText(HTML)

References(36)

References

Aida, T.M., 2022. Fundamental of Hydrothermal Processing of Biomass-Related Molecules for Converting Organic Solid Wastes into Chemical Products in Production of Biofuels and Chemicals from Sustainable Recycling of Organic Solid Waste. Springer-Nature, Singapore.

Aida, T.M., Oshima, M., Smith, R.L., 2017. Controlled conversion of proteins into high-molecular-weight peptides without additives with high-temperature water and fast heating rates. ACS Sustain. Chem. Eng. 5, 7709–7715. doi: 10.1021/acssuschemeng.7b01146

Aida, T.M., Yamagata, T., Abe, C., Kawanami, H., Watanabe, M., Smith, R.L., 2012. Production of organic acids from alginate in high temperature water. J. Supercrit. Fluids 65, 39–44. doi: 10.1016/j.supflu.2012.02.021

Aida, T.M., Yamagata, T., Watanabe, M., Smith, R.L., 2010. Depolymerization of sodium alginate under hydrothermal conditions. Carbohydr. Polym. 80, 296–302. doi: 10.1016/j.carbpol.2009.11.032

Augst, A.D., Kong, H.J., Mooney, D.J., 2006. Alginate hydrogels as biomaterials. Macromol. Biosci. 6, 623–633. doi: 10.1002/mabi.200600069

Burana-Osot, J., Hosoyama, S., Nagamoto, Y., Suzuki, S., Linhardt, R.J., Toida, T., 2009. Photolytic depolymerization of alginate. Carbohydr. Res. 344, 2023–2027. doi: 10.1016/j.carres.2009.06.027

Draget, K.I., Smidsrod, O., Skjak-Braek, G., 2002. Biopolymers. Polysaccharides II: Polysaccharides from Eukaryotes. Wiley-VCH Verlag GmbH, Weinheim, pp. 215–245.

Feng, L.P., Cao, Y.P., Xu, D.X., Wang, S.J., Zhang, J., 2017. Molecular weight distribution, rheological property and structural changes of sodium alginate induced by ultrasound. Ultrason. Sonochem. 34, 609–615. doi: 10.1016/j.ultsonch.2016.06.038

Fenoradosoa, T.A., Ali, G., Delattre, C., Laroche, C., Petit, E., Wadouachi, A., Michaud, P., 2010. Extraction and characterization of an alginate from the brown seaweed Sargassum turbinarioides grunow. J. Appl. Phycol. 22, 131–137. doi: 10.1007/s10811-009-9432-y

Fernando, I.P.S., Kim, D., Nah, J.W., Jeon, Y.J., 2019. Advances in functionalizing fucoidans and alginates (bio)polymers by structural modifications: a review. Chem. Eng. J. 355, 33–48. doi: 10.1016/j.cej.2018.08.115

Goh, C.H., Heng, P.W.S., Chan, L.W., 2012. Alginates as a useful natural polymer for microencapsulation and therapeutic applications. Carbohydr. Polym. 88, 1–12. doi: 10.1016/j.carbpol.2011.11.012

Grant, G.T., Morris, E.R., Rees, D.A., Smith, P.J.C., Thom, D., 1973. Biological interactions between polysaccharides and divalent cations: the egg-box model. FEBS Lett 32, 195–198. doi: 10.1016/0014-5793(73)80770-7

Grasdalen, H., 1983. High-field, 1H-NMR spectroscopy of alginate: sequential structure and linkage conformations. Carbohydr. Res. 118, 255–260. doi: 10.1016/0008-6215(83)88053-7

Haug, A., Larsen, B., Smidsrød, O., Haug, A., Hagen, G., 1967. Alkaline degradation of alginate. Acta Chem. Scand. 21, 2859–2870. doi: 10.3891/acta.chem.scand.21-2859

Haug, A., Larsen, B., Smidsrød, O., Møller, J., Brunvoll, J., Bunnenberg, E., Djerassi, C., Records, R., 1966. A study of the constitution of alginic acid by partial acid hydrolysis. Acta Chem. Scand. 20, 183–190. doi: 10.3891/acta.chem.scand.20-0183

Haug, A., Larsen, B., Smidsröd, O., Munch-Petersen, J., Munch-Petersen, J., 1963. The degradation of alginates at different pH values. Acta Chem. Scand. 17, 1466–1468. doi: 10.3891/acta.chem.scand.17-1466

Hernández-González, A.C., Téllez-Jurado, L., Rodríguez-Lorenzo, L.M., 2020. Alginate hydrogels for bone tissue engineering, from injectables to bioprinting: a review. Carbohydr. Polym. 229, 115514. doi: 10.1016/j.carbpol.2019.115514

Holme, H.K., Lindmo, K., Kristiansen, A., Smidsrød, O., 2003. Thermal depolymerization of alginate in the solid state. Carbohydr. Polym. 54, 431–438. doi: 10.1016/S0144-8617(03)00134-6

Ikeda, A., Takemura, A., Ono, H., 2000. Preparation of low-molecular weight alginic acid by acid hydrolysis. Carbohydr. Polym. 42, 421–425. doi: 10.1016/S0144-8617(99)00183-6

Kelishomi, Z.H., Goliaei, B., Mahdavi, H., Nikoofar, A., Rahimi, M., Moosavi-Movahedi, A.A., Mamashli, F., Bigdeli, B., 2016. Antioxidant activity of low molecular weight alginate produced by thermal treatment. Food Chem 196, 897–902. doi: 10.1016/j.foodchem.2015.09.091

Lee, K.Y., Mooney, D.J., 2012. Alginate: properties and biomedical applications. Prog. Polym. Sci. 37, 106–126. doi: 10.1016/j.progpolymsci.2011.06.003

Li, X.X., Xu, A.H., Xie, H.G., Yu, W.T., Xie, W.Y., Ma, X.J., 2010. Preparation of low molecular weight alginate by hydrogen peroxide depolymerization for tissue engineering. Carbohydr. Polym. 79, 660–664. doi: 10.1016/j.carbpol.2009.09.020

Liu, J., Yang, S.Q., Li, X.T., Yan, Q.J., Reaney, M.J.T., Jiang, Z.Q., 2019. Alginate oligosaccharides: production, biological activities, and potential applications. Compr. Rev. Food Sci. Food Saf. 18, 1859–1881. doi: 10.1111/1541-4337.12494

Matsushima, K., Minoshima, H., Kawanami, H., Ikushima, Y., Nishizawa, M., Kawamukai, A., Hara, K., 2005. Decomposition reaction of alginic acid using subcritical and supercritical water. Ind. Eng. Chem. Res. 44, 9626–9630. doi: 10.1021/ie0502640

Meillisa, A., Woo, H.C., Chun, B.S., 2015. Production of monosaccharides and bio-active compounds derived from marine polysaccharides using subcritical water hydrolysis. Food Chem 171, 70–77. doi: 10.1016/j.foodchem.2014.08.097

Pina, S., Oliveira, J.M., Reis, R.L., 2015. Natural-based nanocomposites for bone tissue engineering and regenerative medicine: a review. Adv. Mater. 27, 1143–1169. doi: 10.1002/adma.201403354

Rehm, B.H.A., Valla, S., 1997. Bacterial alginates: biosynthesis and applications. Appl. Microbiol. Biotechnol. 48, 281–288. doi: 10.1007/s002530051051

Smidsrød, O., Glover, R.M., Whittington, S.G., 1973. The relative extension of alginates having different chemical composition. Carbohydr. Res. 27, 107–118. doi: 10.1016/S0008-6215(00)82430-1

Stokke, B.T., Smidsrød, O., Brant, D.A., 1993. Predicted influence of monomer sequence distribution and acetylation on the extension of naturally occurring alginates. Carbohydr. Polym. 22, 57–66. doi: 10.1016/0144-8617(93)90166-2

Sun, J.Y., Zhao, X.H., Illeperuma, W.R.K., Chaudhuri, O., Oh, K.H., Mooney, D.J., Vlassak, J.J., Suo, Z.G., 2012. Highly stretchable and tough hydrogels. Nature 489, 133–136. doi: 10.1038/nature11409

Szekalska, M., Puciłowska, A., Szymańska, E., Ciosek, P., Winnicka, K., 2016. Alginate: current use and future perspectives in pharmaceutical and biomedical applications. Int. J. Polym. Sci. 2016, 7697031.

Vold, I.M.N., Kristiansen, K.A., Christensen, B.E., 2006. A study of the chain stiffness and extension of alginates, in vitro epimerized alginates, and periodate-oxidized alginates using size-exclusion chromatography combined with light scattering and viscosity detectors. Biomacromolecules 7, 2136–2146. doi: 10.1021/bm060099n

Wang, C.Y., Yokota, T., Someya, T., 2021. Natural biopolymer-based biocompatible conductors for stretchable bioelectronics. Chem. Rev. 121, 2109–2146. doi: 10.1021/acs.chemrev.0c00897

Yang, Z., Li, J.P., Guan, H.S., 2004. Preparation and characterization of oligomannuronates from alginate degraded by hydrogen peroxide. Carbohydr. Polym. 58, 115–121. doi: 10.1016/j.carbpol.2004.04.022

Yue, W., Zhang, H.H., Yang, Z.N., Xie, Y., 2021. Preparation of low-molecular-weight sodium alginate by ozonation. Carbohydr. Polym. 251, 117104. doi: 10.1016/j.carbpol.2020.117104

Zhao, X.H., Kim, J., Cezar, C.A., Huebsch, N., Lee, K., Bouhadir, K., Mooney, D.J., 2011. Active scaffolds for on-demand drug and cell delivery. Proce. Natl. Acad. Sci. U.S.A. 108, 67–72. doi: 10.1073/pnas.1007862108

Relative Articles

Supplements(0)

Cited By

Proportional views