Abstract
In the present study, sulfated polysaccharides were obtained by digestion of Sargassum horneri and preparation with enzyme-assisted extraction using three food-grade enzymes, and their anti- Alzheimer’s activities were investigated. The results demonstrated that the crude sulfated polysaccharides extracted using AMGSP, CSP and VSP dose-dependently (25–100 µg·mL− 1) raised the spontaneous alternating manner (%) in the Y maze experiment of mice and reduced the escape latency time in Morris maze test. AMGSP, CSP and VSP also exhibited good anti-AChE and moderate anti-BuChE activities. CSP displayed the best inhibitory efficacy against AChE. with IC50 values of 9.77 µM. And, CSP also exhibited good inhibitory selectivity of AChE over BuChE. Next, CSP of the best active crude extract was separated by the preparation type high performance liquid phase to obtain the sulphated fucooligosaccharide section: SFcup (→3-α-L-fucp(2-SO3−)-1→4-α-L-fucp(2,3-SO3−)-1→section), SFcup showed a best inhibitory efficacy against AChE with IC50 values of 4.03 µM. The kinetic research showed that SFcup inhibited AChE through dual binding sites. Moreover, the molecular docking of SFcup at the AChE active site was in accordance with the acquired pharmacological results.
Similar content being viewed by others
References
Hippius H, Neundörfer G (2003) The discovery of Alzheimer’s disease. Dialogues Clin Neuro 5:101–108
Uddin MS, Mamun AA, Kabir Md T, JakariaMd MB, Barreto GE, Ghulam Md A (2019) Nootropic and Anti-alzheimer’s actions of medicinal plants: molecular insight into therapeutic potential to alleviate Alzheimer’s neuropathology. MolNeurobiol56:4925–4944
World Alzheimer Report (2015) Available online: https://www.alz.co.uk/research/ world Alzheimer report 2015 summary.pdf (accessed on 26 January 2017)
Zhu Y, Peng L, Hu J, Chen Y, Chen FX (2019) Current anti-alzheimer’s disease effect of natural products and their principal targets. J Integr Neurosci 18(3):327–339
Sharma K (2019) Cholinesterase inhibitors as Alzheimer’s therapeutics (review). MolMed Rep 20(2):1479–1487
Chaurasiya ND, Leon F, Muhammad I, Tekwani BL (2022) Natural products inhibitors of monoamine oxidases-potential new drug leads for neuroprotection, neurological disorders, and neuroblastoma. Molecules 27:4297
Liu WH, Zhao DH, He ZW, Hu YM, Zhu YX, Zhang LJ, Jin LH, Guan LP Wang SH(2022)synthesis, characterization and biological evaluation of benzothiazole-isoquinoline derivative. Molecules 27: 9062
Wijesekara I, Pangestuti R, Kim SK (2011) Biological activities and potential health benefits of sulfated polysaccharides derived from marine algae. Carbohyd Polym 84:14–21
Lehmann L, Lo A, Knox KM, Barker-Haliski M (2021) Alzheimer’s disease and epilepsy: a perspec- tive on the opportunities for overlapping therapeutic innovation. Neurochem Res 46(8):1895–1912
Wan T, Fu MY, Jiang Y, Jiang WW, Li PL, Zhou SH (2022) Research progress on mechanism of neuroprotective roles of Apelin-13 in prevention and treatment of Alzheimer’s disease. Neurochem Res 47(2):205–217
Sanjeewa KKA, Kim EA, Son KT, Jeon YJ (2016) Bioactive properties and potentials cosmeceutical applications of phlorotannins isolated from brown seaweeds: a review. J Photo PhotobioB 162:100–105
Rathnayake AU, Abuine R, Kim YJ, Byun HG (2019) Anti-alzheimer’s materials isolated from marine bio-resources: a review. Curr Alzheimer Res 16(10):895–906
Gao YL, Li CM, Yin JG, Shen JY, Wang HT, Wu YZ, Jin HZ (2012) Fucoidan, a sulfated polysaccharide from brown algae, improves cognitive impairment induced by infusion of Aβ peptide in rats. EnvironToxicolPhar33(2):304–311
Pang SJ, Liu F, Shan FT, Gao SQ, Zhang ZH (2009) Cultivation of the brown alga Sargassum Horneri: sexual reproduction and seedling production in tank culture under reduced solar irradiance in ambient temperature. J ApplPhycol 21:413–422
Liu L, Heinrich M, Myers S, Dworjanyn SA (2012) Towards a better understanding of medicinal uses of the brown seaweed Sargassum in traditional Chinese medicine: a phytochemical and pharmacological review. J Ethnopharmacol 142(3):591–619
Asanka Sanjeewa KK, Shanura Fernand IP, Kim EA, Ahn G, Jee Y, Jeon YJ (2017) Anti- inflammatory activity of a sulfated polysaccharide isolated from an enzymatic digest of brown seaweed sargassumhorneri in RAW 264.7 cells. Nutr ResPract 11(1):3–10
Shao P, Chen X, ,Sun P (2014) Chemical characterization, antioxidant and antitumor activity of sulfated polysaccharide from Sargassumhorneri. Carbohyd Polym 105:260–269
Wen ZS, Xiang XW, Jin HX, Guo XY, Liu LJ, Huang YN, OuYang XK, Qu YL (2016) Composition and anti-inflammatory effect of polysaccharides from Sargassumhorneri in RAW264.7 macrophages. Int J Bio Macromol 88:403–413
DuBois M, Gilles KA, Hamilton JK, Rebers PA, Smith F (1956) Colorimetric method for determination of sugars and related substances. Anal Chem 28:350–356
Chandler SF, Dodds JL (1983) The effect of phosphate, nitrogen and sucrose on the production of phenolics and solasodine in callus cultures of solanumlaciniatum. Plant Cell Rep 2(4):205–208
Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248–254
Saito H, Yamagata T, Suzuki S (1968) Enzymatic methods for the determination of small quantities of isomeric chondroitin sulfates. J Biol Chem 243(7):1536–1542
Heo SJ, Jeon YJ, Lee JH, Kim HT, Lee KW (2003) Antioxidant effect of enzymatic hydrolyzate from a kelp. Ecklonia cava Algae 18:341–347
Shao P, Chen X, Sun P (2015) Improvement of antioxidant and moisture-preserving activities of Sargassum Horneri polysaccharide enzymatic hydrolyzates. Int J Biol Macromol 74:420–427
SilchenkoAS, Rasin AB, Kusaykin MI, Kalinovsky AI, Zhang MS, Liu CH, Zhao C, Li N, Wang C, Yan M, Shan J, Lin C, Guo T (2017) Structure, enzymatic transformation, anticancer activity of fucoidan and sulfated fucooligosaccharides from Sargassum Horneri. Carbohyd Polym 175:654–660
Vorhees CV, Williams MT (2006) Morris water maze: procedures for assessing spatial and related forms of learning and memory. Nat Protoc 1(2):848–858
Ellman GL, Courtney KD, Andres V, Featherstone RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 7:88–95
Singh T, Biswas D, Jayaram B (2011) AADS-an automated active site identification, docking, and scoring protocol for protein targets based on physicochemical descriptors. J Chem Information and Modeling 51(10):2515–2527
Schneider RW (1984) Effects of nonpathogenic strains of fusariumoxysporum on celery root infection by F. Oxysporum f. sp. apii and a novel use of the Lineweaver-Burk double reciprocal plot technique. Phytopathol 74:646
MOE. Chemical computing group, Inc., Montereal, https://www.chemcomp.com/
Jesumani V, Du H, Pei PB, Zheng CQ, Cheong KL, Huang N (2019) Unravelling property of polysaccharides from Sargassum Sp as an antiwrinkle and skin whitening property. Int J Biol Macromol 140:216–224
Wijesinghe WAJ, Jeon PYJ (2012) Biological activities and potential industrial applications of fucose rich sulfated polysaccharides and fucoidans isolated from brown seaweeds: a review. Carbohyd Polym 88:13–20
YangL, Zhang LM (2009) Chemical structural and chain conformational characterization of some bioactive polysaccharides isolated from natural sources. Carbohyd Polym 76:349–361
Gómez-Ordóñez E, Rupérez P (2011) FTIR-ATR spectroscopy as a tool for polysaccharide identification in edible brown and red seaweeds. Food Hydrocolloid 25:1514–1520
Leblhuber F, Steiner K, Schuetz B, Fuchs D, Gostner JM (2018) Probiotic supplementation in patients with Alzheimer’s dementia-an explorative intervention study. Curr Alzheimer Res 15(12):1106–1113
Morris R (1984) Developments of a water-maze procedure for studying spatial learning in the rat. JNeurosci Meth 11(1):47–60
Ali T, Badshah H, Kim TH, Kim MO (2015) Melatonin attenuates D-galactose-induced memory impairment, neuroinflammation and neurodegeneration via RAGE/NF-KB/JNK signaling pathway in aging mouse model. J Pineal Res 58(1):71–85
Bashir MA, Khan AU, Badshah H, Rodrigues-Filho E, Din ZU, Khan A (2019) Synthesis, characterization, molecular docking evaluation, antidepressant, and anti-alzheimer effects of dibenzylidene ketone derivatives. Drug Develp Res 80(5):595–605
Sharma A, Kumar Y (2019) Nature´s derivatives as alternative anti-Alzheimer´s disease treatments. J Alzheimer´s Dis Rep 3(1):279–297
Tan QW, He LY, Zhang SS, He ZW, Liu WH, Zhang L, Guan LP, Wang SH (2022) Design, synth- esis, and biological activity of chalcone analogs containing 4-phenylquinolin and benzohydrazide. Chem Biodivers 19:e202100610
Barage SH, Sonawane KD (2015) Amyloid cascade hypothesis: pathogenesis and therapeutic strategies in Alzheimer´s disease. Neuropeptides 52:1–18
Hussein W, Sağlık BN, Levent S, Korkut B, Ilgın S, Özkay ID Y, Kaplancıklı ZA (2018) Synthesis and biological evaluation of new cholinesterase inhibitors for Alzheimer´s Disease. Molecules 23(8): 2033
Acknowledgements
We thank Sihong Wang from Yanbian University, China, for spectrum testing and spectrum analysis in this article. We thank Liwen Bianji, Edanz Editing China (www.liwenbianji.cn/ac), for editing the English text of a draft of the article.
Funding
The work was funded by Fujian Provincial Key Laboratory of Innovative Drug Target Research (NO. FJ-YW-2023KF04) and Zhejiang Ocean University Undergraduate Innovation Project (Academic Papers, 2022).
Author information
Authors and Affiliations
Contributions
L.P., Y.J. and QH were Conceptualization, Writing-original draft, Writing-review & editing; L.J., H.Z., F.N., and Y.W. prepared Investigation, Finishing the Experiments, and Data Analysis; T. and M. Assisted Execution Experiments. All authors reviewed the manuscript.
Corresponding authors
Ethics declarations
Conflict of Interest
There is no declaration of interest.
Competing Interests
The authors declare no competing interests.
Additional information
Publisher’s Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic Supplementary Material
Below is the link to the electronic supplementary material.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Zhang, LJ., Zhang, HZ., Liu, YW. et al. Sulphated Fucooligosaccharide from Sargassum Horneri: Structural Analysis and Anti-Alzheimer Activity. Neurochem Res 49, 1592–1602 (2024). https://doi.org/10.1007/s11064-024-04107-x
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11064-024-04107-x