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On-line Access: 2023-07-15

Received: 2022-12-06

Revision Accepted: 2023-02-27

Crosschecked: 2023-07-17

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Citations:  Bibtex RefMan EndNote GB/T7714

 ORCID:

Wei CHEN

https://orcid.org/0000-0002-2373-2437

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Journal of Zhejiang University SCIENCE B 2023 Vol.24 No.7 P.574-586

http://doi.org/10.1631/jzus.B2200629


Polysaccharide isolated from wax apple suppresses ethyl carbamate-induced oxidative damage in human hepatocytes


Author(s):  Tao BAO, Naymul KARIM, Huihui KE, Jitbanjong TANGPONG, Wei CHEN

Affiliation(s):  Department of Traditional Chinese Medicine, Sir Run Run Shaw Hospital, School of Medicine, Zhejiang University, Hangzhou 310016, China; more

Corresponding email(s):   zjuchenwei@zju.edu.cn

Key Words:  Wax apple polysaccharide, Polysaccharide characterization, Ethyl carbamate, Hepatic oxidative stress


Tao BAO, Naymul KARIM, Huihui KE, Jitbanjong TANGPONG, Wei CHEN. Polysaccharide isolated from wax apple suppresses ethyl carbamate-induced oxidative damage in human hepatocytes[J]. Journal of Zhejiang University Science B, 2023, 24(7): 574-586.

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Abstract: 
Wax apple (Syzygium samarangense) has received growing research interest for its high nutritional and medicinal value due to its constituents such as polysaccharide, organic acids, flavonoids, minerals, and other substances. In this study, wax apple polysaccharide (WAP) was isolated from this plant and its protective effect against ethyl carbamate (EC)‍-induced oxidative damage was evaluated in human hepatocytes (L02 cells). Firstly, a series of analyses such as high-performance liquid chromatography (HPLC), high-performance gel permeation chromatography (HPGPC), Fourier transform infrared spectroscopy (FT-IR), gas chromatography/mass spectrometry (GC/MS), and 1H and 13C nuclear magnetic resonance (NMR) were conducted to identify the structure of WAP. Thereafter, in vitro cell experiments were performed to verify the protective effects of WAP against EC-induced cytotoxicity, genotoxicity, and oxidative damage in L02 cells. Our results revealed that WAP is composed of mannose, rhamnose, glucuronic acid, galacturonic acid, glucose, galactose, arabinose, and fucose in a molar ratio of 2.20:‍3.94:‍4.45:‍8.56:‍8.86:‍30.82:‍39.78:‍1.48. Using a combination of methylation and NMR spectroscopic analysis, the primary structure of WAP was identified as Araf-(1→, Glcp-(1→, →2)‍-Araf-(1→, →3)‍-Galp-(1→, →3)‍-Araf-‍(1→, and →6)‍-Galp-‍(1→. Cell experiments indicated that WAP exhibited significant protective effects on EC-treated L02 cells via suppressing cytotoxicity and genotoxicity, reducing reactive oxygen species (ROS) and O2•- formation, as well as improving mitochondrial membrane potential (MMP) and glutathione (GSH). In a nutshell, WAP has the potential as an important therapeutic agent or supplement for hepatic oxidative damage. Meanwhile, further studies are needed to prove the above effects in vivo at the biological and clinical levels.

莲雾多糖对氨基甲酸乙酯诱导人肝细胞氧化损伤的抑制作用研究

鲍涛1,2,Naymul KARIM1,2,柯慧慧2,Jitbanjong TANGPONG4,陈卫1,2,3
1浙江大学医学院附属邵逸夫医院中医科,中国杭州市,310016
2浙江大学食品科学与营养系,中国杭州市,310058
3浙江大学宁波创新中心,中国宁波市,315100
4泰国瓦莱拉大学联合健康科学学院生物医学科学,泰国洛坤府,80161
摘要:莲雾(Syzygium samarangense)因其含有多糖、有机酸、类黄酮、矿物质等功能活性成分而具有很高的营养和药用价值,受到越来越多研究者的关注。本研究从莲雾中分离出水溶性多糖(WAP),并在人肝细胞(L02细胞)中评估了其对氨基甲酸乙酯(EC)诱导的氧化损伤的保护作用。首先采用高效液相色谱法(HPLC)、高效凝胶渗透色谱(HPGPC)、傅里叶变换红外光谱(FT-IR)、气相色谱/质谱(GC/MS)、1H和13C核磁共振(NMR)等一系列分析方法来鉴定WAP的结构。随后进行体外细胞实验验证WAP对EC诱导的L02细胞中的细胞毒性、遗传毒性和氧化损伤的保护作用。结果表明,莲雾的WAP由甘露糖、鼠李糖、葡萄糖醛酸、半乳糖醛酸、葡萄糖、半乳糖、阿拉伯糖和岩藻糖组成,其摩尔比为2.20:3.94:4.45:8.56:8.86:30.82:39.78:1.48。结合甲基化和NMR光谱分析,WAP的一级结构为Araf-(1→、Glcp-(1→、→2)-Araf-(1→、→3)-Galp-(1→、→3)-Araf-(1→和→6)-Galp-(1→。体外细胞实验表明,WAP通过抑制细胞毒性和遗传毒性,减少活性氧(ROS)和超氧根离子(O2??)的形成,对EC诱导的L02细胞表现出显著的保护作用。综上所述,WAP具有作为肝脏氧化损伤的重要治疗剂或补充剂的潜力,但仍需通过体内生物学和临床研究进一步证实上述作用。

关键词:莲雾多糖;多糖表征;氨基甲酸乙酯;肝脏氧化应激

Darkslateblue:Affiliate; Royal Blue:Author; Turquoise:Article

Reference

[1]AgrawalPK, 1992. NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides. Phytochemistry, 31(10):3307-3330.

[2]BaoT, XuY, GowdV, et al., 2016. Systematic study on phytochemicals and antioxidant activity of some new and common mulberry cultivars in China. J Funct Foods, 25:‍537-547.

[3]BaoT, ZhangM, ZhouYQ, et al., 2021. Phenolic profile of jujube fruit subjected to gut microbiota fermentation and its antioxidant potential against ethyl carbamate-induced oxidative damage. J Zhejiang Univ-Sci B (Biomed & Biotechnol), 22(5):397-409.

[4]BhatAH, DarKB, AneesS, et al., 2015. Oxidative stress, mitochondrial dysfunction and neurodegenerative diseases; a mechanistic insight. Biomed Pharmacother, 74:101-110.

[5]ChenW, ZhaoZ, LiYQ, 2011. Simultaneous increase of mycelial biomass and intracellular polysaccharide from Fomes fomentarius and its biological function of gastric cancer intervention. Carbohydr Polym, 85(2):369-375.

[6]ChenW, ZhuangJJ, LiY, et al., 2013. Myricitrin protects against peroxynitrite-mediated DNA damage and cytotoxicity in astrocytes. Food Chem, 141(2):927-933.

[7]ChenW, ShenY, SuHM, et al., 2014. Hispidin derived from Phellinus linteus affords protection against acrylamide-induced oxidative stress in Caco-2 cells. Chem Biol Interact, 219:83-89.

[8]ChenW, SuHM, XuY, et al., 2016a. Protective effect of wild raspberry (Rubus hirsutus Thunb.) extract against acrylamide-induced oxidative damage is potentiated after simulated gastrointestinal digestion. Food Chem, 196:943-952.

[9]ChenW, XuY, ZhangLX, et al., 2016b. Blackberry subjected to in vitro gastrointestinal digestion affords protection against Ethyl Carbamate-induced cytotoxicity. Food Chem, 212:620-627.

[10]ChenW, XuY, ZhangLX, et al., 2016c. Wild raspberry subjected to simulated gastrointestinal digestion improves the protective capacity against ethyl carbamate-induced oxidative damage in Caco-2 cells. Oxid Med Cell Longev, 2016:3297363.

[11]ChenW, LiYT, BaoT, et al., 2017. Mulberry fruit extract affords protection against ethyl carbamate-induced cytotoxicity and oxidative stress. Oxid Med Cell Longev, 2017:1594963.

[12]ChenXQ, TianXZ, ShinI, et al., 2011. Fluorescent and luminescent probes for detection of reactive oxygen and nitrogen species. Chem Soc Rev, 40(9):4783-4804.

[13]ChunSH, ChaYN, KimC, 2013. Urethane increases reactive oxygen species and activates extracellular signal-regulated kinase in RAW 264.7 macrophages and A549 lung epithelial cells. Arch Pharm Res, 36(6):775-782.

[14]Cichoż-LachH, MichalakA, 2014. Oxidative stress as a crucial factor in liver diseases. World J Gastroenterol, 20(25):8082-8091.

[15]CiucanuI, KerekF, 1984. A simple and rapid method for the permethylation of carbohydrates. Carbohydr Res, 131(2):209-217.

[16]CuiX, WangJY, QiuNN, et al., 2016. In vitro toxicological evaluation of ethyl carbamate in human HepG2 cells. Toxicol Res, 5(2):697-702.

[17]da Silva MarineliR, MoraesÉA, LenquisteSA, et al., 2014. Chemical characterization and antioxidant potential of Chilean chia seeds and oil (Salvia hispanica L.). LWT-Food Sci Technol, 59(2):1304-1310.

[18]DuBoisM, GillesKA, HamiltonJK, et al., 1956. Colorimetric method for determination of sugars and related substances. Anal Chem, 28(3):350-356.

[19]EsuaJO, ChinNL, YusofYA, et al., 2017. Antioxidant bioactive compounds and spoilage microorganisms of wax apple (Syzygium samarangense) during room temperature storage. Int J Fruit Sci, 17(2):188-201.

[20]GorinPAJ, MazurekM, 1975. Further studies on the assignment of signals in 13C magnetic resonance spectra of aldoses and derived methyl glycosides. Can J Chem, 53(8):1212-1223.

[21]GottliebHE, KotlyarV, NudelmanA, 1997. NMR chemical shifts of common laboratory solvents as trace impurities. J Org Chem, 62(21):7512-7515.

[22]GowdV, SuHM, KarlovskyP, et al., 2018a. Ethyl carbamate: an emerging food and environmental toxicant. Food Chem, 248:312-321.

[23]GowdV, BaoT, WangLL, et al., 2018b. Antioxidant and antidiabetic activity of blackberry after gastrointestinal digestion and human gut microbiota fermentation. Food Chem, 269:618-627.

[24]GowdV, BaoT, ChenW, 2019. Antioxidant potential and phenolic profile of blackberry anthocyanin extract followed by human gut microbiota fermentation. Food Res Int, 120:523-533.

[25]GuoSD, MaoWJ, HanY, et al., 2010. Structural characteristics and antioxidant activities of the extracellular polysaccharides produced by marine bacterium Edwardsiella tarda. Bioresour Technol, 101(12):4729-4732.

[26]HuangDW, ChangWC, WuJSB, et al., 2016. Vescalagin from pink wax apple [Syzygium samarangense (Blume) Merrill and Perry] alleviates hepatic insulin resistance and ameliorates glycemic metabolism abnormality in rats fed a high-fructose diet. J Agric Food Chem, 64(5):1122-1129.

[27]IARC, 2010. Alcohol consumption and ethyl carbamate. In: IARC Monographs on the Identification of Carcinogenic Hazards to Humans. IARC, Lyon, France. http://monographs.iarc.fr/ENG/Monographs/vol96/index.php

[28]JiaoZH, DongYC, ChenQH, 2014. Ethyl carbamate in fermented beverages: presence, analytical chemistry, formation mechanism, and mitigation proposals. Compr Rev Food Sci Food Saf, 13(4):611-626.

[29]JinHF, LiuMC, ZhangX, et al., 2016. Grape seed procyanidin extract attenuates hypoxic pulmonary hypertension by inhibiting oxidative stress and pulmonary arterial smooth muscle cells proliferation. J Nutr Biochem, 36:81-88.

[30]KarimN, JiaZQ, ZhengXD, et al., 2018. A recent review of citrus flavanone naringenin on metabolic diseases and its potential sources for high yield-production. Trends Food Sci Technol, 79:35-54.

[31]KarimN, ShishirMRI, LiYT, et al., 2022. Pelargonidin-3-O-glucoside encapsulated pectin-chitosan-nanoliposomes recovers palmitic acid-induced hepatocytes injury. Antioxidants, 11(4):623.

[32]KodaliVP, SenR, 2008. Antioxidant and free radical scavenging activities of an exopolysaccharide from a probiotic bacterium. Biotechnol J, 3(2):245-251.

[33]LiYH, WangS, SunY, et al., 2020. Apple polysaccharide could promote the growth of Bifidobacterium longum. Int J Biol Macromol, 152:1186-1193.

[34]LiYT, BaoT, ChenW, 2018. Comparison of the protective effect of black and white mulberry against ethyl carbamate-induced cytotoxicity and oxidative damage. Food Chem, 243:65-73.

[35]LinMT, BealMF, 2006. Mitochondrial dysfunction and oxidative stress in neurodegenerative diseases. Nature, 443(7113):787-795.

[36]LiuHC, CuiB, XuY, et al., 2017. Ethyl carbamate induces cell death through its effects on multiple metabolic pathways. Chem Biol Interact, 277:21-32.

[37]LiuXC, ZhuZY, TangYL, et al., 2016. Structural properties of polysaccharides from cultivated fruit bodies and mycelium of Cordyceps militaris. Carbohydr Polym, 142:63-72.

[38]LuY, BaoT, MoJL, et al., 2021. Research advances in bioactive components and health benefits of jujube (Ziziphus jujube Mill.) fruit. J Zhejiang Univ-Sci B (Biomed & Biotechnol), 22(6):431-449.

[39]LuoQL, TangZH, ZhangXF, et al., 2016. Chemical properties and antioxidant activity of a water-soluble polysaccharide from Dendrobium officinale. Int J Biol Macromol, 89:219-227.

[40]MengM, ChengD, HanLR, et al., 2017. Isolation, purification, structural analysis and immunostimulatory activity of water-soluble polysaccharides from Grifola Frondosa fruiting body. Carbohydr Polym, 157:1134-1143.

[41]MengSL, ChenX, GyimahE, et al., 2020. Hepatic oxidative stress, DNA damage and apoptosis in adult zebrafish following sub-chronic exposure to BDE-47 and BDE-153. Environ Toxicol, 35(11):1202-1211.

[42]NgTB, PiZF, FuM, et al., 2006. A polysaccharopeptide complex and a condensed tannin with antioxidant activity from dried rose (Rosa rugosa) flowers. J Pharm Pharmacol, 58(4):529-534.

[43]PervaizS, ClementMV, 2007. Superoxide anion: oncogenic reactive oxygen species? Int J Biochem Cell Biol, 39(7-8):1297-1304.

[44]RenYY, ZhuZY, SunHQ, et al., 2017. Structural characterization and inhibition on α-glucosidase activity of acidic polysaccharide from Annona squamosa. Carbohydr Polym, 174:1-12.

[45]Resurreccion-MagnoMHC, VillaseñorIM, HaradaN, et al., 2005. Antihyperglycaemic flavonoids from Syzygium samarangense (Blume) Merr. and Perry. Phytother Res, 19(3):246-251.

[46]Rodríguez-RamiroI, RamosS, BravoL, et al., 2011. Procyanidin B2 and a cocoa polyphenolic extract inhibit acrylamide-induced apoptosis in human Caco-2 cells by preventing oxidative stress and activation of JNK pathway. J Nutr Biochem, 22(12):1186-1194.

[47]ShilaS, SubathraM, DeviMA, et al., 2005. Arsenic intoxication-induced reduction of glutathione level and of the activity of related enzymes in rat brain regions: reversal by DL-α-lipoic acid. Arch Toxicol, 79(3):140-146.

[48]ShishirMRI, KarimN, GowdV, et al., 2019. Liposomal delivery of natural product: a promising approach in health research. Trends Food Sci Technol, 85:177-200.

[49]SimirgiotisMJ, AdachiS, ToS, et al., 2008. Cytotoxic chalcones and antioxidants from the fruits of Syzygium samarangense (Wax Jambu). Food Chem, 107(2):813-819.

[50]SongS, ZhangB, WuSF, et al., 2018. Structural characterization and osteogenic bioactivity of a sulfated polysaccharide from pacific abalone (Haliotis discus hannai Ino). Carbohydr Polym, 182:207-214.

[51]SrivastavaR, ShawAK, KulshreshthaDK, 1995. Triterpenoids and chalcone from Syzygium samarangense. Phytochemistry, 38(3):687-689.

[52]SulaimanSF, OoiKL, 2014. Antioxidant and α‍-glucosidase inhibitory activities of 40 tropical juices from Malaysia and identification of phenolics from the bioactive fruit juices of Barringtonia racemosa and Phyllanthus acidus. J Agric Food Chem, 62(39):9576-9585.

[53]SunJ, HeH, XieBJ, 2004. Novel antioxidant peptides from fermented mushroom Ganoderma lucidum. J Agric Food Chem, 52(21):6646-6652.

[54]TamielloCS, doNascimento GE, IacominiM, et al., 2018. Arabinogalactan from edible jambo fruit induces different responses on cytokine secretion by THP-1 macrophages in the absence and presence of proinflammatory stimulus. Int J Biol Macromol, 107:35-41.

[55]UttaraB, SinghAV, ZamboniP, et al., 2009. Oxidative stress and neurodegenerative diseases: a review of upstream and downstream antioxidant therapeutic options. Curr Neuropharmacol, 7(1):65-74.

[56]WangBH, CaoJJ, ZhangB, et al., 2019. Structural characterization, physicochemical properties and α-glucosidase inhibitory activity of polysaccharide from the fruits of wax apple. Carbohydr Polym, 211:227-236.

[57]WangJQ, HuSZ, NieSP, et al., 2016. Reviews on mechanisms of in vitro antioxidant activity of polysaccharides. Oxid Med Cell Longev, 2016:5692852.

[58]WangWH, HanZJ, GuoDQ, et al., 2021. Renal transcriptomics reveals the carcinogenic mechanism of ethyl carbamate in musalais. Onco Targets Ther, 14:1401-1416.

[59]XieJH, WangZJ, ShenMY, et al., 2016. Sulfated modification, characterization and antioxidant activities of polysaccharide from Cyclocarya paliurus. Food Hydrocolloids, 53:7-15.

[60]YanCY, YinY, ZhangDW, et al., 2013. Structural characterization and in vitro antitumor activity of a novel polysaccharide from Taxus yunnanensis. Carbohydr Polym, 96(2):389-395.

[61]YanMX, MaoWJ, LiuX, et al., 2016. Extracellular polysaccharide with novel structure and antioxidant property produced by the deep-sea fungus Aspergillus versicolor N2bc. Carbohydr Polym, 147:272-281.

[62]YangHW, 2022. Research and application progress of bioactive components in fruits and leaves of wax apple. Food Sci Technol, 47(2):262-267 (in Chinese).

[63]ZengWC, ZhangZ, JiaLR, 2014. Antioxidant activity and characterization of antioxidant polysaccharides from pine needle (Cedrus deodara). Carbohydr Polym, 108:58-64.

[64]ZhangLX, XuY, LiYT, et al., 2017. Protective property of mulberry digest against oxidative stress‍‍—a potential approach to ameliorate dietary acrylamide-induced cytotoxicity. Food Chem, 230:306-315.

[65]ZhangQB, LiN, ZhouGF, et al., 2003. In vivo antioxidant activity of polysaccharide fraction from Porphyra haitanesis (Rhodephyta) in aging mice. Int J Biol Macromol, 48(2):151-155.

[66]ZorovDB, JuhaszovaM, SollottSJ, 2014. Mitochondrial reactive oxygen species (ROS) and ROS-induced ROS release. Physiol Rev, 94(3):909-950.

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