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2022 | OriginalPaper | Buchkapitel

Antioxidant Effect of Syringic Acid Grafted Chitooligosaccharides in RAW264.7 Cells

verfasst von : Van-Hoai Bui, Hong-Tham N Vo, Dai-Nghiep Ngo

Erschienen in: 8th International Conference on the Development of Biomedical Engineering in Vietnam

Verlag: Springer International Publishing

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Abstract

Reactive oxygen species (ROS) that attack biomolecules leading to many health disorders. Chitooligosaccharides (COSs) is a natural antioxidant that has a positive effect against ROS. It may be applied in the functional food and pharmaceutical industries. In recent years, importance has been given to synthesize functionalized COSs by chemical modifications to improve the bioactivities of COSs while keeping intact the basic chemical properties. Therefore, this work aims to develop a novel COSs derivatives by conjugation of syringic acid onto plain COSs to improve the antioxidant activity of COSs. In this study, the syringic acid was grafted onto COSs by a free radical mediated grafting method with an ascorbic acid/hydrogen peroxide redox catalysis pair. Antioxidant effects of the novel COSs derivatives were determined by reducing power, free radical scavenging ability, and the inhibition of cellular macromolecules’ oxidation, such as lipid and DNA in RAW264.7 cells. The result showed that free radical scavenging effects and inhibitory effects of the novel derivatives of biomacromolecules oxidation were significative improved more than free COSs. These results suggest that the novel COSs derivatives can be potentially used as a free radical scavenger to protect biomacromolecules in cellular systems. Besides, the research is a foundation for further study of other activities such as the anti-inflammatory properties of these derivatives.

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Vorheriges Kapitel The Influence of High D-glucose Concentrations on Increasing the Expression of EGR-1, PTEN and GGPS-1 Involved in Insulin Resistance of AT-MSCs

Nächstes Kapitel Identification of Plant Disease Based on Multi-feature Extraction

Cross CE, Halliwell B, Borish ET, Pryor WA, Ames BN, Saul RL, Mccord JM, Harman D (1987) Oxygen radicals and human disease. Ann Intern Med 107(4):526–545. https://doi.org/10.7326/0003-4819-107-4-526CrossRef

McCord JM (2000) The evolution of free radicals and oxidative stress. Am J Med 108(8):652–659. https://doi.org/10.1016/S0002-9343(00)00412-5CrossRef

Veselinovic M, Barudzic N, Vuletic M, Zivkovic V, Tomic-Lucic A, Djuric D, Jakovljevic V (2014) Oxidative stress in rheumatoid arthritis patients: relationship to diseases activity. Mol Cell Biochem 391(1–2):225–232. https://doi.org/10.1007/s11010-014-2006-6CrossRef

Quinonez-Flores CM, Gonzalez-Chavez SA, Del Rio Najera D, Pacheco-Tena C (2016) Oxidative stress relevance in the pathogenesis of the rheumatoid arthritis: a systematic review. Biomed Res Int 2016:6097417. https://doi.org/10.1155/2016/6097417CrossRef

Butterfield DA, Perluigi M, Sultana R (2006) Oxidative stress in Alzheimer’s disease brain: new insights from redox proteomics. Eur J Pharmacol 545(1):39–50. https://doi.org/10.1016/j.ejphar.2006.06.026CrossRef

Dias V, Junn E, Mouradian MM (2013) The role of oxidative stress in Parkinson’s disease. J Parkinsons Dis 3(4):461–491. https://doi.org/10.3233/JPD-130230CrossRef

Pollari E, Goldsteins G, Bart G, Koistinaho J, Giniatullin R (2014) The role of oxidative stress in degeneration of the neuromuscular junction in amyotrophic lateral sclerosis. Front Cell Neurosci 8:131. https://doi.org/10.3389/fncel.2014.00131CrossRef

Pignatelli P, Menichelli D, Pastori D, Violi F (2018) Oxidative stress and cardiovascular disease: new insights. Kardiol Pol 76(4):713–722. https://doi.org/10.5603/KP.a2018.0071CrossRef

Bowler RP, Crapo JD (2002) Oxidative stress in allergic respiratory diseases. J Allergy Clin Immunol 110(3):349–356. https://doi.org/10.1067/mai.2002.126780CrossRef

10.

Biller-Takahashi JD, Takahashi LS, Mingatto FE, Urbinati EC (2015) The immune system is limited by oxidative stress: dietary selenium promotes optimal antioxidative status and greatest immune defense in pacu Piaractus mesopotamicus. Fish Shellfish Immunol 47(1):360–367. https://doi.org/10.1016/j.fsi.2015.09.022CrossRef

11.

Hamada Y, Fujii H, Fukagawa M (2009) Role of oxidative stress in diabetic bone disorder. Bone 45:35–38. https://doi.org/10.1016/j.bone.2009.02.004CrossRef

12.

Khandrika L, Kumar B, Koul S, Maroni P, Koul HK (2009) Oxidative stress in prostate cancer. Cancer Lett 282(2):125–136. https://doi.org/10.1016/j.canlet.2008.12.011CrossRef

13.

Lodhi G, Kim YS, Hwang JW, Kim SK, Jeon YJ, Je JY, Ahn CB, Moon SH, Jeon BT, Park PJ (2014) Chitooligosaccharide and its derivatives: preparation and biological applications. Biomed Res Int 2014:654913. https://doi.org/10.1155/2014/654913CrossRef

14.

Hamed I, Özogul F, Regenstein JM (2016) Industrial applications of crustacean by-products (chitin, chitosan, and chitooligosaccharides): a review. Trends Food Sci Technol 48:40–50CrossRef

15.

Liaqat F, Eltem R (2018) Chitooligosaccharides and their biological activities: a comprehensive review. Carbohydr Polym 184:243–259. https://doi.org/10.1016/j.carbpol.2017.12.067CrossRef

16.

Phil L, Naveed M, Mohammad IS, Bo L, Bin D (2018) Chitooligosaccharide: an evaluation of physicochemical and biological properties with the proposition for determination of thermal degradation products. Biomed Pharmacother 102:438–451. https://doi.org/10.1016/j.biopha.2018.03.108CrossRef

17.

Park PJ, Je JY, Kim SK (2003) Free radical scavenging activity of chitooligosaccharides by electron spin resonance spectrometry. J Agric Food Chem 51:4624–4627. https://doi.org/10.1021/jf034039CrossRef

18.

Lillo L, Alarco’n J, Cabello G, Céspedes C, Caro C (2008) Antibacterial activity of chitooligosaccharides. J Biosci 63:644–648. https://doi.org/10.1515/znc-2008-9-1005

19.

Jeon YJ, Kim SK (1999) Production of chitooligosaccharides using an ultrafiltration membrane reactor and their antibacterial activity. Carbohydr Polym 41:133–141. https://doi.org/10.1016/S0144-8617(99)00084-3CrossRef

20.

Shen KT, Chen MH, Chan HY, Jeng JH, Wang YJ (2009) Inhibitory effects of chitooligosaccharides on tumor growth and metastasis. Food Chem Toxicol 47:1864–1871. https://doi.org/10.1016/j.fct.2009.04.044CrossRef

21.

Li X, Wang J, Chen X, Tian J, Li L, Zhao M, Jiao Y, Zhou C (2011) Effect of chitooligosaccharides on cyclin D1, bcl-xl and bcl-2 mRNA expression in A549 cells using quantitative PCR. Chin Sci Bull 56(15):1629–1632. https://doi.org/10.1007/s11434-010-4501-9CrossRef

22.

Yang Y, Xing R, Liu S, Qin Y, Li K, Yu H, Li P (2019) Immunostimulatory effects of chitooligosaccharides on RAW 264.7 mouse macrophages via regulation of the MAPK and PI3K/Akt signaling pathways. Mar Drugs 17(1). https://doi.org/10.3390/md17010036

23.

Ma P, Liu HT, Wei P, Xu QS, Bai XF, Du YG (2011) Chitosan oligosaccharides inhibit LPS-induced over-expression of IL-6 and TNF-α in RAW264.7 macrophage cells through blockade of mitogen-activated protein kinase (MAPK) and PI3K/Akt signaling pathways. Carbohydr Polym 84(4):1391–1398. https://doi.org/10.1016/j.carbpol.2011.01.045

24.

Artan M, Karadeniz F, Karagozlu MZ, Kim MM, Kim SK (2010) Anti-HIV-1 activity of low molecular weight sulfated chitooligosaccharides. Carbohydr Res 345(5):656–662. https://doi.org/10.1016/j.carres.2009.12.017CrossRef

25.

Yoon NY, Ngo DN, Kim SK (2009) Acetylcholinesterase inhibitory activity of novel chitooligosaccharide derivatives. Carbohyd Polym 78:869–872. https://doi.org/10.1016/j.carbpol.2009.07.004CrossRef

26.

Liu J, Wang X, Bai R, Zhang N, Kan J, Jin C (2018) Synthesis, characterization, and antioxidant activity of caffeic-acid-grafted corn starch. Starch—Stärke 70(1–2). https://doi.org/10.1002/star.201700141

27.

Cikman O, Soylemez O, Ozkan OF, Kiraz HA, Sayar I, Ademoglu S, Taysi S, Karaayvaz M (2015) Antioxidant activity of syringic acid prevents oxidative stress in l-arginine-induced acute pancreatitis: an experimental study on rats. Int Surg 100(5):891–896. https://doi.org/10.9738/INTSURG-D-14-00170.1CrossRef

28.

Ngo DH, Qian ZJ, Vo TS, Ryu B, Ngo DN, Kim SK (2011) Antioxidant activity of gallate-chitooligosaccharides in mouse macrophage RAW264.7 cells. Carbohydr Polym 84:1182–1288. https://doi.org/10.1016/j.carbpol.2011.01.022

29.

Cho YS, Kim SK, Ahn CB, Je JY (2011) Preparation, characterization, and antioxidant properties of gallic acid-grafted-chitosans. Carbohydr Polym 83(4):1617–1622. https://doi.org/10.1016/j.carbpol.2010.10.019CrossRef

30.

Eom TK, Senevirathne M, Kim SK (2012) Synthesis of phenolic acid conjugated chitooligosaccharides and evaluation of their antioxidant activity. Environ Toxicol Pharmacol 34:519–527. https://doi.org/10.1016/j.etap.2012.05.004CrossRef

31.

Vo TS, Ngo DH, Bach LG, Ngo DN, Kim SK (2017) The free radical scavenging and anti-inflammatory activities of gallate-chitooligosaccharides in human lung epithelial A549 cells. Process Biochem 54:188–194. https://doi.org/10.1016/j.procbio.2017.01.001CrossRef

32.

Bui VH, Ngo DN (2019) The research determines appropriate parameters in the synthesis process of syringic acid grafted chitooligosaccharides. Sci Technol Dev J 22(3):317–323. https://doi.org/10.32508/stdj.v22i3.1289CrossRef

33.

Ngo DN, Kim MM, Kim SK (2012) Protective effects of aminoethyl-chitooligosaccharides against oxidative stress in mouse macrophage RAW 264.7 cells. Int J Biol Macromol 50:624–631. https://doi.org/10.1016/j.ijbiomac.2012.01.036

34.

Lee DS, Woo JY, Ahn CB, Je JY (2014) Chitosan–hydroxycinnamic acid conjugates: preparation, antioxidant and antimicrobial activity. Food Chem 148:97–104. https://doi.org/10.1016/j.foodchem.2013.10.019CrossRef

35.

Blois MS (1958) Antioxidant determination by the use of a stable free radical. Nature 181:1199–1200CrossRef

36.

Halliwell B, Gutteridge JMC, Aruoma OI (1987) The deoxyribose method: a simple “test-tube” assay for determination of rate constants for reactions of hydroxyl radicals. Anal Biochem 165:215–219. https://doi.org/10.1016/0003-2697(87)90222-3CrossRef

37.

Ngo DH, Qian ZJ, Ngo DN, Vo TS, Wijesekara I, Kim SK (2011) Gally chitooligosaccharides inhibit intracellular free radical-mediated oxidation. Food Chem 128:974–981. https://doi.org/10.1016/j.foodchem.2011.03.128

38.

Ngo DN, Kim MM, Kim SK (2008) Chitin oligosacchride inhibit oxidative stress in live cells. Carbohydr Polym 74:119–123. https://doi.org/10.1016/j.carbpol.2008.02.005CrossRef

39.

Ngo D-H, Qian Z-J, Ngo D-N, Vo T-S, Wijesekara I, Kim S-K (2011) Gallyl chitooligosaccharides inhibit intracellular free radical-mediated oxidation. Food Chem 128(4):974–981. https://doi.org/10.1016/j.foodchem.2011.03.128CrossRef

40.

Canabady-Rochelle LL, Harscoat-Schiavo C, Kessler V, Aymes A, Fournier F, Girardet JM (2015) Determination of reducing power and metal chelating ability of antioxidant peptides: revisited methods. Food Chem 183:129–135. https://doi.org/10.1016/j.foodchem.2015.02.147CrossRef

41.

Aytekin AO, Morimura S, Kida K (2011) Synthesis of chitosan-caffeic acid derivatives and evaluation of their antioxidant activities. J Biosci Bioeng 111(2):212–216. https://doi.org/10.1016/j.jbiosc.2010.09.018CrossRef

42.

Chatterjee NS, Panda SK, Navitha M, Asha KK, Anandan R, Mathew S (2015) Vanillic acid and coumaric acid grafted chitosan derivatives: improved grafting ratio and potential application in functional food. J Food Sci Technol 52(11):7153–7162. https://doi.org/10.1007/s13197-015-1874-4CrossRef

43.

Trinh MDL, Dinh MH, Ngo DH, Tran DK, Tran QT, Vo TS, Ngo DN (2014) Prevention of H₂O₂-induced oxidative stress in Chang liver cells by 4-hydroxybenzyl-chitooligomers. Carbohydr Polym 103:502–509. https://doi.org/10.1016/j.carbpol.2013.12.061CrossRef

44.

Liu J, Pu H, Liu S, Kan J, Jin C (2017) Synthesis, characterization, bioactivity and potential application of phenolic acid grafted chitosan: a review. Carbohydr Polym 174:999–1017. https://doi.org/10.1016/j.carbpol.2017.07.014CrossRef

Titel: Antioxidant Effect of Syringic Acid Grafted Chitooligosaccharides in RAW264.7 Cells
verfasst von: Van-Hoai Bui
Hong-Tham N Vo
Dai-Nghiep Ngo
Verlag: Springer International Publishing
Buch: 8th International Conference on the Development of Biomedical Engineering in Vietnam
Print ISBN: 978-3-030-75505-8

Electronic ISBN: 978-3-030-75506-5

Copyright-Jahr: 2022
DOI: https://doi.org/10.1007/978-3-030-75506-5_43

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