杏仁皮提取物对果糖及其两种代谢产物大鼠肝细胞毒性的保护作用
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摘要
近年来,果糖含量在人类饮食中增长已经成为肥胖及脂肪肝发生的重要因素。Day提出了非酒精性脂肪性肝炎(NASH)发病机制,即两次打击学说:第一次打击是脂肪变性,第二次打击为氧化应激。在动物模型中,糖摄取过量会造成由氧化应激和羰基应激,从而导致的细胞毒性、炎症和组织损伤。也已证实晚期糖基化终产物(AGEs)的形成是(NASH)和非酒精性脂肪肝疾病(NAFLD)的关键因素。用果糖饲喂的老鼠会导致胰岛素抵抗、血清中果糖代谢产物甲基乙二醛(MGO)的含量升高。AGEs的前体乙二醛(GO)诱导肝细胞毒性可能是NASH的第二次打击。但是有关果糖(乙二醛前体)的毒作用机制,目前尚无报道。本论文对果糖的肝细胞毒性及其机制进行了研究,并探讨杏仁皮提取物和天然产物儿茶素类对乙二醛的细胞毒性抑制作用。
为研究果糖的肝细胞毒性及其机制,论文首先在牛血清白蛋白(BSA)模型上研究Fenton反应体系下果糖及其两种代谢产物(甘油醛和乙醇醛)对BSA酰基化作用的机制;其次以用不同浓度的果糖及其两种代谢产物分别诱导肝细胞毒性,探讨其细胞毒性机制。研究表明:在BSA模型中,果糖本身并不导致BSA的酰基化,但在Fenton体系(FeII/H2O2或CuI/H2O2)作用下可酰基化蛋白,FeII/H2O2的作用比CuI/H2O2强。果糖代谢产物(甘油醛或乙醇醛)在Fenton反应体系下对蛋白质的羰基化作用显着增加。乙二醛捕获剂氨基胍可以完全阻止果糖、甘油醛和乙醇醛蛋白质羰基化。羟基自由基清除剂可以抑制FeII催化的Fenton反应导致的蛋白质羰基化,但羟基自由基清除剂没有抑制CuI/H2O2所导致的蛋白质羰基化。在肝细胞炎症模型中,果糖本身的毒性为1.5M,而在无毒剂量的H2O2存在时,其肝细胞毒性为10 mM,毒性在FeIII:HQ(8-羟基喹啉)的存在下进一步增加。甘油醛和乙醇醛在H2O2存在时肝细胞毒性增加,在FeIII:HQ/H2O2存在时毒性进一步增加。果糖、甘油醛和乙醇醛在H2O2或FeIII:HQ/H2O2存在时的毒性增加倍率的大小为:果糖>乙醇醛>甘油醛。甘油醛或乙醇醛的肝细胞毒性在CuII:HQ/H2O2的诱导下也增加,但羟自由基清除剂只抑制FeIII:HQ/H2O2诱导的细胞毒性而不抑制CuII:HQ/H2O2诱导的细胞毒性。氨基胍可以抑制FeIII:HQ/H2O2和CuII:HQ/H2O2诱导的细胞毒性及蛋白质羰基化。
果糖及其代谢产物(如乙二醛或甲基乙二醛)引起的氧化应激和羰基应激,是糖尿病并发症以及其他慢性疾病的关键因素。但富含生物活性化合物的饮食可以抑制这个过程。杏仁皮含有多种生物活性化合物和抗氧化剂,如类黄酮和多酚等天然产物,可以减缓氧化和羰基应激。本论文以不同的方法制备了四种杏仁皮提取物(ASEⅠ,ⅡASE,ASEⅢ,和ASEⅣ)并测定其抗氧化活性。并测定总多酚含量和抗氧化活性,其抗氧化能力强弱顺序与总多酚含量大小顺序一致,ASEⅠ最强;铜诱导的Fenton反应可导致蛋白质酰基化,ASE抑制此蛋白质酰基化的能力强弱依次为:ASEⅠ>ASEⅣ>ASEⅡ。在体外羰基应激模型,乙二醛或甲基乙二醛导致蛋白质羰基化。ASEⅠ、儿茶素和表儿茶素均可以营救出血清白蛋白。儿茶素和表儿茶素以等摩尔浓度营救出血清白蛋白。ASE可以抑制对叔丁基过氧化氢(TBH)诱导的大鼠微粒体脂质过氧化反应,保护作用由大到小的顺序为:ASEⅠ>ASEⅣ>ASEⅡ,ASEⅢ。ASE还可以保护叔丁基过氧化氢诱导的肝细胞毒作用,顺序为:ASEⅢ,ASEⅣ>ASEⅠ,ASEⅡ。同时,儿茶素类也保护TBH诱导肝脂质过氧化和肝细胞的细胞毒性。儿茶素、表儿茶素和ASEⅠ均抑制乙二醛诱导的肝细胞毒性,同时抑制活性氧ROS的产生。儿茶素类对乙二醛或甲基乙二醛诱导的肝细胞毒性有保护作用,同时也抑制蛋白质羰基化和活性氧的生成。
结论:果糖及其代谢产物(甘油醛和乙醇醛)在Fenton反应体系下代谢为乙二醛,引发氧化应激和羰基应激,应激中形成的ROS导致肝细胞毒性;果糖或果糖代谢物在Fenton体系反应下肝细胞毒性增加可能是NASH的第二次打击,肝细胞所受到的氧化应激环境可以继续增加肝细胞毒性和诱发NASH;杏仁皮成分多酚提取物是有效生物活性成分,可以抑制氧化应激诱导的肝细胞毒性,可以抑制有效活性羰基化合物诱导的细胞毒性;儿茶素类通过有效捕获乙二醛和甲基乙二醛,或者抑制肝细胞蛋白质羰基化的途径来抑制乙二醛和甲基乙二醛诱导的细胞毒性。
Dietary fructose consumption is associated with the development of obesity and hepatic steatosis. A two hit hypothesis by Day has been proposed for the pathogenesis of non-alcoholic steatohepatitis (NASH), the first hit being hepatic steatosis, and the second hit being oxidative stress. Excessive sugar intake in animal models may cause tissue damage associated with oxidative and carbonyl stress cytotoxicity as well as inflammation. AGEs (advanced glycation end products) formation is also key factors that are involved in aging and chronic diseases, including NASH (non-alcoholic steatohepatitis), NAFLD (non-alcoholic fatty liver disease) and diabetes. In addition, rats fed fructose developed insulin resistance and increased their serum methylglyoxal (MGO), a fructose metabolite. As previously reported, glyoxal (GO) induced hepatocyte toxicity could be attributed to mitochondrial toxicity. However the toxic mechanism of fructose, a glyoxal precursor has not been investigated. In present thesis, we investigate the the cytotoxicity
To test out whether hepatocyte toxicity is induced by fructose“Molecular Mechansm Removed”a cell free model was used to study the carbonyl stress caused by fructose and its metabolites (glyceraldehyde and glycoaldehyde). Isolated hepatocytes were incubated with different concentrations of fructose and its metabolites (glycolaldehyde and glyceraldehyde) . The toxicity and the molecular cytotoxic mechanisms involved were also investigated. Fructose alone did not carbonylate bovine serum albumin (BSA) in a cell free system but did so in the presence of low concentrations of FeII/H2O2 whereas CuI/H2O2 was less effective. Furthermore protein carbonylation by the fructose metabolites glyceraldehyde or glycolaldehyde were also markedly increased by FeII/H2O2 whereas CuI/H2O2 was less effective. Protein carbonylation was attributed to glyoxal formation as the glyoxal trapping agent aminoguanidine completely prevented the protein carbonylation. Glyoxal were also much more effective than most carbonyls at causing protein carbonylation. Glyoxal was rapidly formed when fructose, glycolaldehyde or glyceraldehyde were oxidized by FeII/H2O2.. Hydroxyl radical scavengers inhibited the protein carbonylation induced by fructose, glyceraldehyde or glycolaldehyde and catalysed by FeII/H2O2 but not by CuI/H2O2 suggesting that hydroxyl radicals were formed by a FeII catalysed Fenton reaction but less so by a CuI catalysed Fenton reaction. In the hepatocytes inflammation model, fructose itself was toxic at 1.5M, whereas only 10mM fructose was toxic when hepatocytes were also exposed to a non-cytotoxic dose of H2O2. The cytotoxicity was further increased in the presence of FeIII:HQ. The molecular mechanism for fructose cytotoxicity involved oxidative stress as endogenous reactive oxygen species (ROS) and H2O2 formation preceded cytotoxicity. Fructose/H2O2 cytotoxicity was markedly increased by trace amounts of FeIII: 8-hydroxyquinoline (HQ). Fructose, glyceraldehyde or glycolaldehyde cytotoxicity was also markedly increased by a non toxic H2O2 infusion generated by glucose/glucose oxidase which was further increased if the hepatocytes were loaded with non toxic 2μM FeIII:HQ. The order of the increased fold of cytotoxicity was : Fructose > glycolaldehyde > glyceraldehydes. Cytotoxicity induced by glyceraldehyde or glycolaldehyde/FeIII:HQ/H2O2 but not glyceraldehyde or glycolaldehyde/CuII:HQ/H2O2 was inhibited by hydroxyl radical scavengers. The glyoxal scavenger aminoguanidine inhibited the cytotoxicity by glyceraldehyde or glycolaldehyde /FeII:HQ/H2O2 and glyceraldehyde or glycolaldehyde /CuII:HQ/H2O2. Protein carbonylation by glyceraldehyde/FeII:HQ/H2O2 was inhibited by hydroxyl radical scavengers or the glyoxal scavenger aminoguanidine.
Oxidative and carbonyl stress induced by dicarbonyls such as glyoxal or methylglyoxal, are detrimental in the pathogenesis of diabetic complications, as well as in other chronic diseases. However, this process may be decreased by dietary bioactive compounds. Almond skin is an abundant source of bioactive compounds and antioxidants, including polyphenolic flavonoids, which may contribute to the decrease in oxidative and carbonyl stress. In this study, four Almond Skin Extracts (ASEⅠ, ASEⅡ, ASEⅢ, and ASEⅣ) were prepared by different methods and evaluated for their antioxidant activity. The order of the polyphenol content (totalμM gallic acid equivalents) of the four extracts was found to be, in decreasing order of effectiveness: ASEⅠ> ASEⅢ> ASEⅣ> ASEⅡ. The order of Ferric-reducing antioxidant power (FRAP,μM FeSO4/g) value, in decreasing order was ASEⅠ(216) > ASEⅢ(176) > ASEⅣ(89) > ASEⅡ(85). The order of ASE effectiveness for decreasing protein carbonylation induced by the copper Fenton reaction was ASEⅠ> ASEⅣ> ASEⅡ> ASEⅢ. The order of antioxidant effectiveness for inhibiting tertiary-butyl hydroperoxide (TBH) induced microsomal lipid peroxidation was ASEⅠ> ASEⅣ> ASEⅡ, ASEⅢ. Also, the order of ASE effectiveness for inhibiting TBH induced hepatocyte toxicity was: ASEⅢ, ASEⅣ> ASEⅠ, ASEⅡ. Catechin also protected hepatocytes from TBH induced hepatocyte lipid peroxidation and cytotoxicity. In a cell free model, ASEⅠ,catechin or epicatechin rescued lbumin from protein carbonylation induced by glyoxal. Equimolar concentrations of catechin or epicatechin rescued serum albumin from protein carbonylation induced by methylglyoxal. ASEⅠCatechin, epicatechin and ASEⅠall decreased glyoxal induced hepatocyte toxicity and Reactive oxygen species (ROS) formation in GSH depleted hepatocytes. Catechin and epicatechin protected against GO or MGO induced hepatocyte toxicity, protein carbonylation and ROS formation. Catechin was more effective than epicatechin.
Conclusion: Glyoxal is formed from fructose and its metabolites by Fenton reaction and contrbutes to cytotoxicity in a inflammatory model. Fatty liver induced by an excessive sugar diet in animal models has been proposed as the first hit for NASH whilst oxidative stress induced by the oxidation of fructose or fructose metabolites by Fenton FeII/H2O2 could be a‘second hit’. A perpetual cycle of oxidative stress in hepatocytes could lead to cytotoxicity and NASH development. Bioactive almond skin constituents in the non-lipophilic polyphenol extract were the most effective at protecting hepatocytes against hydroperoxide induced hepatocyte oxidative stress and in protecting against dicarbonyl induced cytotoxicity. Catechins, the major polyphenol in the extract, were also effective at preventing GO or MGO cytotoxicity likely by trapping GO and MGO and/or rescuing hepatocytes from protein carbonylation.
为研究果糖的肝细胞毒性及其机制,论文首先在牛血清白蛋白(BSA)模型上研究Fenton反应体系下果糖及其两种代谢产物(甘油醛和乙醇醛)对BSA酰基化作用的机制;其次以用不同浓度的果糖及其两种代谢产物分别诱导肝细胞毒性,探讨其细胞毒性机制。研究表明:在BSA模型中,果糖本身并不导致BSA的酰基化,但在Fenton体系(FeII/H2O2或CuI/H2O2)作用下可酰基化蛋白,FeII/H2O2的作用比CuI/H2O2强。果糖代谢产物(甘油醛或乙醇醛)在Fenton反应体系下对蛋白质的羰基化作用显着增加。乙二醛捕获剂氨基胍可以完全阻止果糖、甘油醛和乙醇醛蛋白质羰基化。羟基自由基清除剂可以抑制FeII催化的Fenton反应导致的蛋白质羰基化,但羟基自由基清除剂没有抑制CuI/H2O2所导致的蛋白质羰基化。在肝细胞炎症模型中,果糖本身的毒性为1.5M,而在无毒剂量的H2O2存在时,其肝细胞毒性为10 mM,毒性在FeIII:HQ(8-羟基喹啉)的存在下进一步增加。甘油醛和乙醇醛在H2O2存在时肝细胞毒性增加,在FeIII:HQ/H2O2存在时毒性进一步增加。果糖、甘油醛和乙醇醛在H2O2或FeIII:HQ/H2O2存在时的毒性增加倍率的大小为:果糖>乙醇醛>甘油醛。甘油醛或乙醇醛的肝细胞毒性在CuII:HQ/H2O2的诱导下也增加,但羟自由基清除剂只抑制FeIII:HQ/H2O2诱导的细胞毒性而不抑制CuII:HQ/H2O2诱导的细胞毒性。氨基胍可以抑制FeIII:HQ/H2O2和CuII:HQ/H2O2诱导的细胞毒性及蛋白质羰基化。
果糖及其代谢产物(如乙二醛或甲基乙二醛)引起的氧化应激和羰基应激,是糖尿病并发症以及其他慢性疾病的关键因素。但富含生物活性化合物的饮食可以抑制这个过程。杏仁皮含有多种生物活性化合物和抗氧化剂,如类黄酮和多酚等天然产物,可以减缓氧化和羰基应激。本论文以不同的方法制备了四种杏仁皮提取物(ASEⅠ,ⅡASE,ASEⅢ,和ASEⅣ)并测定其抗氧化活性。并测定总多酚含量和抗氧化活性,其抗氧化能力强弱顺序与总多酚含量大小顺序一致,ASEⅠ最强;铜诱导的Fenton反应可导致蛋白质酰基化,ASE抑制此蛋白质酰基化的能力强弱依次为:ASEⅠ>ASEⅣ>ASEⅡ。在体外羰基应激模型,乙二醛或甲基乙二醛导致蛋白质羰基化。ASEⅠ、儿茶素和表儿茶素均可以营救出血清白蛋白。儿茶素和表儿茶素以等摩尔浓度营救出血清白蛋白。ASE可以抑制对叔丁基过氧化氢(TBH)诱导的大鼠微粒体脂质过氧化反应,保护作用由大到小的顺序为:ASEⅠ>ASEⅣ>ASEⅡ,ASEⅢ。ASE还可以保护叔丁基过氧化氢诱导的肝细胞毒作用,顺序为:ASEⅢ,ASEⅣ>ASEⅠ,ASEⅡ。同时,儿茶素类也保护TBH诱导肝脂质过氧化和肝细胞的细胞毒性。儿茶素、表儿茶素和ASEⅠ均抑制乙二醛诱导的肝细胞毒性,同时抑制活性氧ROS的产生。儿茶素类对乙二醛或甲基乙二醛诱导的肝细胞毒性有保护作用,同时也抑制蛋白质羰基化和活性氧的生成。
结论:果糖及其代谢产物(甘油醛和乙醇醛)在Fenton反应体系下代谢为乙二醛,引发氧化应激和羰基应激,应激中形成的ROS导致肝细胞毒性;果糖或果糖代谢物在Fenton体系反应下肝细胞毒性增加可能是NASH的第二次打击,肝细胞所受到的氧化应激环境可以继续增加肝细胞毒性和诱发NASH;杏仁皮成分多酚提取物是有效生物活性成分,可以抑制氧化应激诱导的肝细胞毒性,可以抑制有效活性羰基化合物诱导的细胞毒性;儿茶素类通过有效捕获乙二醛和甲基乙二醛,或者抑制肝细胞蛋白质羰基化的途径来抑制乙二醛和甲基乙二醛诱导的细胞毒性。
Dietary fructose consumption is associated with the development of obesity and hepatic steatosis. A two hit hypothesis by Day has been proposed for the pathogenesis of non-alcoholic steatohepatitis (NASH), the first hit being hepatic steatosis, and the second hit being oxidative stress. Excessive sugar intake in animal models may cause tissue damage associated with oxidative and carbonyl stress cytotoxicity as well as inflammation. AGEs (advanced glycation end products) formation is also key factors that are involved in aging and chronic diseases, including NASH (non-alcoholic steatohepatitis), NAFLD (non-alcoholic fatty liver disease) and diabetes. In addition, rats fed fructose developed insulin resistance and increased their serum methylglyoxal (MGO), a fructose metabolite. As previously reported, glyoxal (GO) induced hepatocyte toxicity could be attributed to mitochondrial toxicity. However the toxic mechanism of fructose, a glyoxal precursor has not been investigated. In present thesis, we investigate the the cytotoxicity
To test out whether hepatocyte toxicity is induced by fructose“Molecular Mechansm Removed”a cell free model was used to study the carbonyl stress caused by fructose and its metabolites (glyceraldehyde and glycoaldehyde). Isolated hepatocytes were incubated with different concentrations of fructose and its metabolites (glycolaldehyde and glyceraldehyde) . The toxicity and the molecular cytotoxic mechanisms involved were also investigated. Fructose alone did not carbonylate bovine serum albumin (BSA) in a cell free system but did so in the presence of low concentrations of FeII/H2O2 whereas CuI/H2O2 was less effective. Furthermore protein carbonylation by the fructose metabolites glyceraldehyde or glycolaldehyde were also markedly increased by FeII/H2O2 whereas CuI/H2O2 was less effective. Protein carbonylation was attributed to glyoxal formation as the glyoxal trapping agent aminoguanidine completely prevented the protein carbonylation. Glyoxal were also much more effective than most carbonyls at causing protein carbonylation. Glyoxal was rapidly formed when fructose, glycolaldehyde or glyceraldehyde were oxidized by FeII/H2O2.. Hydroxyl radical scavengers inhibited the protein carbonylation induced by fructose, glyceraldehyde or glycolaldehyde and catalysed by FeII/H2O2 but not by CuI/H2O2 suggesting that hydroxyl radicals were formed by a FeII catalysed Fenton reaction but less so by a CuI catalysed Fenton reaction. In the hepatocytes inflammation model, fructose itself was toxic at 1.5M, whereas only 10mM fructose was toxic when hepatocytes were also exposed to a non-cytotoxic dose of H2O2. The cytotoxicity was further increased in the presence of FeIII:HQ. The molecular mechanism for fructose cytotoxicity involved oxidative stress as endogenous reactive oxygen species (ROS) and H2O2 formation preceded cytotoxicity. Fructose/H2O2 cytotoxicity was markedly increased by trace amounts of FeIII: 8-hydroxyquinoline (HQ). Fructose, glyceraldehyde or glycolaldehyde cytotoxicity was also markedly increased by a non toxic H2O2 infusion generated by glucose/glucose oxidase which was further increased if the hepatocytes were loaded with non toxic 2μM FeIII:HQ. The order of the increased fold of cytotoxicity was : Fructose > glycolaldehyde > glyceraldehydes. Cytotoxicity induced by glyceraldehyde or glycolaldehyde/FeIII:HQ/H2O2 but not glyceraldehyde or glycolaldehyde/CuII:HQ/H2O2 was inhibited by hydroxyl radical scavengers. The glyoxal scavenger aminoguanidine inhibited the cytotoxicity by glyceraldehyde or glycolaldehyde /FeII:HQ/H2O2 and glyceraldehyde or glycolaldehyde /CuII:HQ/H2O2. Protein carbonylation by glyceraldehyde/FeII:HQ/H2O2 was inhibited by hydroxyl radical scavengers or the glyoxal scavenger aminoguanidine.
Oxidative and carbonyl stress induced by dicarbonyls such as glyoxal or methylglyoxal, are detrimental in the pathogenesis of diabetic complications, as well as in other chronic diseases. However, this process may be decreased by dietary bioactive compounds. Almond skin is an abundant source of bioactive compounds and antioxidants, including polyphenolic flavonoids, which may contribute to the decrease in oxidative and carbonyl stress. In this study, four Almond Skin Extracts (ASEⅠ, ASEⅡ, ASEⅢ, and ASEⅣ) were prepared by different methods and evaluated for their antioxidant activity. The order of the polyphenol content (totalμM gallic acid equivalents) of the four extracts was found to be, in decreasing order of effectiveness: ASEⅠ> ASEⅢ> ASEⅣ> ASEⅡ. The order of Ferric-reducing antioxidant power (FRAP,μM FeSO4/g) value, in decreasing order was ASEⅠ(216) > ASEⅢ(176) > ASEⅣ(89) > ASEⅡ(85). The order of ASE effectiveness for decreasing protein carbonylation induced by the copper Fenton reaction was ASEⅠ> ASEⅣ> ASEⅡ> ASEⅢ. The order of antioxidant effectiveness for inhibiting tertiary-butyl hydroperoxide (TBH) induced microsomal lipid peroxidation was ASEⅠ> ASEⅣ> ASEⅡ, ASEⅢ. Also, the order of ASE effectiveness for inhibiting TBH induced hepatocyte toxicity was: ASEⅢ, ASEⅣ> ASEⅠ, ASEⅡ. Catechin also protected hepatocytes from TBH induced hepatocyte lipid peroxidation and cytotoxicity. In a cell free model, ASEⅠ,catechin or epicatechin rescued lbumin from protein carbonylation induced by glyoxal. Equimolar concentrations of catechin or epicatechin rescued serum albumin from protein carbonylation induced by methylglyoxal. ASEⅠCatechin, epicatechin and ASEⅠall decreased glyoxal induced hepatocyte toxicity and Reactive oxygen species (ROS) formation in GSH depleted hepatocytes. Catechin and epicatechin protected against GO or MGO induced hepatocyte toxicity, protein carbonylation and ROS formation. Catechin was more effective than epicatechin.
Conclusion: Glyoxal is formed from fructose and its metabolites by Fenton reaction and contrbutes to cytotoxicity in a inflammatory model. Fatty liver induced by an excessive sugar diet in animal models has been proposed as the first hit for NASH whilst oxidative stress induced by the oxidation of fructose or fructose metabolites by Fenton FeII/H2O2 could be a‘second hit’. A perpetual cycle of oxidative stress in hepatocytes could lead to cytotoxicity and NASH development. Bioactive almond skin constituents in the non-lipophilic polyphenol extract were the most effective at protecting hepatocytes against hydroperoxide induced hepatocyte oxidative stress and in protecting against dicarbonyl induced cytotoxicity. Catechins, the major polyphenol in the extract, were also effective at preventing GO or MGO cytotoxicity likely by trapping GO and MGO and/or rescuing hepatocytes from protein carbonylation.
引文
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