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研究生:賴錫淮
研究生(外文):Hsi-Huai Lai
論文名稱:大豆異黃酮對一氧化氮及活性氮化物傷害性生物效應影響之研究
論文名稱(外文):Effects of Soybean Isoflavones on the Adverse Biological Activities of Nitric Oxide and Reactive Nitrogen Species
指導教授:顏 國 欽
指導教授(外文):Gow-Chin Yen
學位類別:博士
校院名稱:國立中興大學
系所名稱:食品科學系
學門:農業科學學門
學類:食品科學類
論文種類:學術論文
論文出版年:2002
畢業學年度:90
語文別:中文
論文頁數:151
中文關鍵詞:異黃酮化合物一氧化氮過氧化亞硝酸根低密度脂蛋白酪胺酸硝化作用DNA傷害RAW 264.7巨噬細胞誘導型一氧化氮合成酶
外文關鍵詞:isoflavonesnitric oxideperoxynitritelow density lipoproteintyrosine nitrationDNA damageRAW 264.7 macrophageiNOS
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過量一氧化氮(NO)之生合成,與活性氧分子反應會進一步形成具有毒性之活性氮化合物(RNS),進而攻擊一些生物分子包括含血基質蛋白、過氧化酶、含硒蛋白、脂質及DNA,故被認為與一些慢性發炎疾病及某些癌症有關。研究顯示許多類黃酮(flavonoids)及一些多酚類抗氧化物可以有效降低活性氮化合物之毒性。異黃酮 (isoflavones) 為屬於類黃酮之一群化合物,被認為是大豆及其製品之主要抗氧化物質之一,且具有許多生理活性包括植物雌性激素特性、抗發炎活性及減少心血管疾病,亦為酪胺酸激酶(tyrosine kinase)抑制物,而具有抗癌特性。因此本研究主要探討大豆異黃酮對於活性氮化合物(包括一氧化氮及過氧化亞硝酸根) 所造成生物分子之傷害及細胞基因毒性是否具有保護的能力。內容主要分為四部分:(一) 異黃酮對於過氧化亞硝酸根誘導人類低密度脂蛋白以及酪胺酸氧化修飾之影響、(二) 大豆異黃酮對於脂多醣所誘導之RAW 264.7巨噬細胞誘導型一氧化氮合成酶(iNOS)之相關效應及機制、(三) 異黃酮對於sodium nitroprusside (SNP)及過氧化亞硝酸根誘發X174 DNA及巨噬細胞DNA傷害之抑制效應及、(四) 異黃酮及大豆製品抽出物對活性氮化物於體外及體內之抑制效應。
結果顯示:(一)異黃酮genistein及daidzein抑制過氧化亞硝酸根誘導人類低密度脂蛋白氧化修飾之能力較genistin及daidzin為佳,且呈現濃度效應(於25,50及100 M)。另外亦發現此四種異黃酮皆可降低酪胺酸被硝化作用的程度,而表現出清除過氧化亞硝酸根能力。與對照組比較時,四種異黃酮抑制酪胺酸被硝化作用的程度分別為genistein (49 %)、daidzein (40 %)、daidzin (41 %)及genistin (42 %)。(二) Genistein、daidzein及glycitein對於脂多醣(LPS)所活化之巨噬細胞生成亞硝酸鹽的量呈現濃度效應之抑制能力(IC50 50 M),而三種異黃酮皆可直接抑制誘導型一氧化氮合成酶的活性,且對於誘導型一氧化氮合成酶的蛋白質及mRNA 量亦有抑制現象。(三) 異黃酮能夠抑制SNP或過氧化亞硝酸根引起之DNA傷害之效應,此可能與異黃酮對於SNP或過氧化亞硝酸根之清除能力及減少胞內抗氧化相關酵素之去活化有關。(四) 體外之試驗結果顯示大豆製品抽出物具有抗氧化能力,且此能力與抽出物之總異黃酮含量具有相關性。而動物試驗結果顯示,腹腔注射LPS之處理結果會增加大鼠血清中一氧化氮代謝產物包括亞硝酸根、硝酸根及硝化酪胺酸等濃度,分別達安慰劑對照組(4,10 M及58  14 pmol/ml)之4、16及5倍量。以異黃酮(4.0 mg/ kg b.w.)或大豆製品抽出物(1.0 g/kg b.w.)餵食大鼠一週之處理結果,則可顯著性(p<0.05)降低LPS所誘導大鼠血清中亞硝酸根、硝酸根及硝化酪胺酸的濃度。
由於有越來越多的證據闡明活性氮化物與疾病發生過程的關係,因此本研究有關大豆異黃酮具有清除活性氮化物活性,可減少低密度脂蛋白的氧化,抑制酪胺酸硝化作用,降低DNA之傷害程度,抑制誘導型一氧化氮合成酶活性以及可降低LPS所誘導大鼠血清中亞硝酸根、硝酸根及硝化酪胺酸的濃度等結果顯示,多攝取大豆異黃酮也許有助於預防一些與活性氮化物相關之疾病,如一些慢性發炎、心血管疾病及某些癌症的發生。
The overproduction of the molecule nitric oxide (NO) can further react with reactive oxygen species to produce reactive nitrogen species (RNS), which may attack a number of biomolecules such as heme-containing proteins, peroxidases, seleno-proteins, lipids and DNA. Therefore, RNS has been indicated as physiologically contributing to many diseases such as cancer, vascular diseases and some chronic inflammatory diseases. It has been reported that flavonoids and other polyphenol antioxidants efficiently against RNS toxicity. Isoflavones, a member of flavonoids, were recognized to be the main antioxidant components of soybean and its products. In addition, isoflavones also show many bioactivities including phytoestroges properties, anti-inflammation, a lower incidence of heat disease and the activities of tyrosine kinase inhibition which have been implicated in the prevention of cancers. Therefore, the objectives of this study were to investigated the protective effect of isoflavones to NO- or peroxynitrite-mediated damage in vitro and in vivo. There are four topics included in this study: (1) Inhibitory effect of isoflavones on peroxynitrite-mediated low-density lipoprotein oxidation; (2) Suppression effect of soy isoflavones on nitric oxide production in RAW 264.7 macrophages; (3) Inhibitory effects of isoflavones on nitric oxide- or peroxynitrite-mediated DNA damage in RAW 264.7 cells and X174 DNA; and (4) Inhibition of reactive nitrogen species effects by isoflavones and soy-based food extracts in vitro and in vivo.
Results shows that (1) Genistein and daidzein were observed to dose-dependently inhibit peroxynitrite-mediated LDL oxidation, while their glucoside conjugates showed reduced activities. Moreover, all isoflavones used in this study were found to be potent peroxynitrite scavengers, preventing the nitration of tyrosine. The ability of the isoflavones at 50 M to decrease tyrosine nitration induced by peroxynitrite (1 mM) was at the ratios of genistein (49 %), daidzein (40 %), daidzin (41 %) and genistin (42 %), when compared to the control (tyrosine incubated with peroxynitrite only); (2) Genistein, daidzein and glycitein dose-dependently suppress NO production (IC50 50 M) in supernatants of LPS-activated macrophages as measured by nitrite accumulation. In addition, direct inhibition of iNOS activity and markedly reduced iNOS protein were found in homogenates of LPS-activated cells treated with each isoflavone; (3) The inhibition by isoflavones of SNP or peroxynitrite- mediated DNA damage could be attributed to their nitric oxide or peroxynitrite scavenging activities and their prevention of antioxidant enzyme inactivation; (4) In the in vitro experiments, extracts from soy-based foods showed a potent antioxidant activity and which was in correlated with their total isoflavone contents. In the in vivo experiments, oral administration of isoflanones and extracts from soy-based products significantly decreased in serum nitrite, nitrate and nitrotyrosine levels in LPS-induced rat.
Increasing evidence indicates that RNS plays the key role in many diseases development. In this study, we found the RNS scavenging abilities of isoflavone could inhibit LDL oxidation, tyrosine nitration, DNA damage and the activities of iNOS in vitro. Moreover, isoflavone also could significantly decreased in serum nitrite, nitrate and nitrotyrosine levels in LPS-induced rat. Taken together, these results suggest that intake of isoflavones could contribute to the protection against RNS-related disorders such as cardiovascular diseases, chronic inflammatory diseases and cancers.
全文摘要(中)……………………………………………………… I
全文摘要(英)……………………………………………………… III
第一章、文獻整理……………………………………………….. 1
一、一氧化氮的簡介……………………………………………… 1
二、一氧化氮之作用機制………………………………………… 2
三、過氧化亞硝酸根(peroxynitrite)之形成及作用機制…… 5
四、抗氧化物對一氧化氮之影響………………………………… 8
五、類黃銅化合物………………………………………………… 9
六、異黃酮化合物………………………………………………… 10
七、研究目的……………………………………………………… 13
第二章、異黃酮對於過氧化亞硝酸根(peroxynitrite)誘導人類低
密度脂蛋白氧化修飾之抑制效應………………………………… 18
中文摘要…………………………………………………………… 19
英文摘要…………………………………………………………… 20
壹、前言…………………………………………………………… 21
貳、材料與方法…………………………………………………… 23
參、結果…………………………………………………………… 29
肆、討論…………………………………………………………… 32
第三章、大豆異黃酮對於脂多醣所誘導RAW 264.7巨噬細胞誘導型
一氧化氮合成酶之抑制效應……………………………………… 42
中文摘要…………………………………………………………… 43
英文摘要…………………………………………………………… 44
壹、前言…………………………………………………………… 45
貳、材料與方法…………………………………………………… 48
參、結果…………………………………………………………… 54
肆、討論…………………………………………………………… 58
第四章、異黃酮對活性氮化物誘發X174 DNA及RAW 264.7巨噬細
胞DNA傷害之抑制效應………………………………………………66
中文摘要…………………………………………………………… 67
英文摘要…………………………………………………………… 68
壹、前言…………………………………………………………… 69
貳、材料與方法…………………………………………………… 72
參、結果…………………………………………………………… 80
肆、討論…………………………………………………………… 84
第五章、異黃酮及大豆製品抽出物對活性氮化物於體外及體內之抑
制效應……………………………………………………………… 93
中文摘要…………………………………………………………… 94
英文摘要…………………………………………………………… 95
壹、前言…………………………………………………………… 96
貳、材料與方法…………………………………………………… 98
參、結果…………………………………………………………… 109
肆、討論…………………………………………………………… 115
總結論……………………………………………………………… 130
第六章、參考文獻………………………………………………… 132
縮寫………………………………………………………………… 150
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