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研究生:吳志鴻
研究生(外文):Jyh-Horng Wu
論文名稱:相思樹心材具抗氧化及抗發炎成分之分析與鑑定
論文名稱(外文):Identification and Analysis of Antioxidative and Antiinflammatory Ingredients Isolated from the Heartwood of Acacia confusa
指導教授:張上鎮張上鎮引用關係
學位類別:博士
校院名稱:國立臺灣大學
系所名稱:森林學研究所
學門:農業科學學門
學類:林業學類
論文種類:學術論文
論文出版年:2004
畢業學年度:92
語文別:中文
論文頁數:191
中文關鍵詞:COX-2iNOS抗發炎抗氧化抽出成分相思樹
外文關鍵詞:extractivesiNOSantioxidantAcacia confusaCOX-2antiinflammation
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相思樹為台灣常見的本土樹種,主要分布於台灣低海拔山地與丘陵地。目前,有關相思樹的主要功用,除了可供作為傳統薪炭材之外,亦可作為部分結構用材。此外,相思樹為具植物相剋作用之樹種之一,其部份葉部抽出物中所含之Flavonol galloylglycoside類化合物,經海蝦致死試驗已證實具有生物活性。然而,對於相思樹樹皮、心材甚至是葉部中所潛藏具保健醫療功效之抽出物,截至目前為止仍缺乏相關性研究。因此,本研究利用管柱層析、高效能液相層析等技術,分離及純化相思樹抽出成分,並利用自由基捕捉、超氧自由基捕捉、脂質過氧化、氫氧自由基引發DNA破壞、細胞抗氧化壓力以及調節巨噬細胞發炎反應等方法,評估其抗氧化以及抗發炎活性。經由上述活性評估所得之具抗氧化與抗發炎活性成分,則運用質譜儀及核磁共振分析儀等儀器,分析與鑑定其確切結構。
試驗結果顯示,相思樹心材及樹皮抽出物均具有極佳的抗氧化活性。二者對於DPPH自由基及脂質過氧化具有相同的抑制活性;而在超氧自由基捕捉能力方面,心材抽出物則較樹皮抽出物略佳。再者,心材抽出物對DNA具有良好的保護作用,可防止ΦX174超螺旋DNA受過氧化氫光解時所產生氫氧自由基的攻擊;同時,由流式細胞儀的分析結果發現,相思樹心材抽出物亦可降低細胞內過氧化氫的含量。
此外,由相思樹心材乙醇抽出物中共分離出15種酚類化合物,其中,包括:3,7,8,3’-Tetrahydroxy-4’-methoxyflavone、7,8,3’,4’- Tetrahydroxy-4-methoxyflavan-3-ol、7,8,3’4’-Tetrahydroxyflavone、7,8,3’-Trihydroxy-3,4’-dimethoxyflavone、7,3’,4’-Trihydroxyflavone和7,3’,4’-Trihydroxy-3-methoxyflavone六種新黃酮類化合物,以及7,8,3’,4’-Tetrahydroxyflavanone、7,8,3’,4’-Tetrahydroxy-3-methoxy- flavone和3,4,2’,3’,4’-Pentahydroxy-trans-chalcone等三種主要抗氧化物。此外,7,8,3’,4’-Tetrahydroxyflavanone(Melanoxetin)證實具有抑制LPS誘導RAW 264.7巨噬細胞iNOS及COX-2 mRNA表現之能力。


Acacia confusa Merr. (Leguminosae), a species indigenous to Taiwan, is widely distributed on the hills and lowlands of Taiwan. It represents a traditionally important commodity used for charcoal-making and construction materials. It has been reported that A. confusa is an allelopathic plant, and the leaves contain flavonol galloylglycosides, some of those exhibit anti-hatch activity against brine shrimp. However, the potential health benefits of A. confusa bark, heartwood, and leaf extracts have not been studied to date. In this study, column chromatography (CC) and high performance liquid chromatography (HPLC) were employed to separate and purify the constituents of the ethanolic extracts of A. confusa. Furthermore, the antioxidative and antiinflammatory activities were evaluated by various assays including free radical and superoxide radical scavenging assays, lipid peroxidation assay, hydroxyl radical-induced DNA strand scission assay, cellular antioxidative stress assay, and modulation of macrophage activity assay. In addition, the chemical structure of bioactive constituents from A. confusa was identified by the analyses of mass spectroscopy and nucleus magnetic resonance spectroscopy (NMR), etc.
Results demonstrated that the bark and heartwood extracts from A. confusa have strong antioxidant effects. Significant and similar inhibitory activities of both extract samples were found for 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical generation and lipid peroxidation. As for the superoxide radical scavenging activity, the heartwood extract was more effective than the bark extract. Furthermore, the heartwood extract protected ФX174 supercoiled DNA against strand scission induced by ultraviolet photolysis of H2O2, and it also reduced the amounts of intracellular hydrogen peroxide, a reactive oxygen species, when it was co-incubated with human promyelocytic leukemia (HL-60) cells under oxidative stress.
Fifteen pure phenolic compounds, including six new flavonoids (3,7,8,3’-tetrahydroxy-4’-methoxyflavone, 7,8,3’,4’-tetrahydroxy-4- methoxyflavan-3-ol, 7,8,3’4’-tetrahydroxyflavone, 7,8,3’-trihydroxy- 3,4’-dimethoxyflavone, 7,3’,4’-trihydroxyflavone, and 7,3’,4’-trihydroxy- 3-methoxyflavone) and three novel antioxidants (7,8,3’,4’-tetrahydroxy- flavanone, 7,8,3’,4’-tetrahydroxy-3-methoxyflavone, and 3,4,2’,3’,4’- pentahydroxy-trans-chalcone), were isolated from the ethanolic extracts of A. confusa heartwood. Among them, 7,8,3’,4’-tetrahydroxyflavanone (melanoxetin) significantly affects iNOS and COX-2 mRNA expression in LPS-stimulated RAW 264.7 macrophage cells.


目錄(I)
表目次(IV)
圖目次(VI)
摘要(1)
Abstract(3)
壹、前言(5)
貳、文獻回顧(8)
一、單寧的結構與類別(13)
(一)Proanthocyanidin類(13)
(二)水解性單寧(Hydrolyzable tannin)(19)
二、氧的危害(22)
三、細胞中活性氧的形成與抗氧化之防禦(25)
參、材料與方法(28)
一、試驗材料(28)
(一)相思樹(28)
(二)試驗藥品(28)
(三)分離純化用品(31)
(四)細胞培養用品(31)
(五)儀器設備(31)
(六)試驗動物(33)
(七)細胞株(33)
二、試驗方法(34)
(一)相思樹抽出成分的萃取(34)
(二)相思樹心材萃取物的分離與純化(34)
1. 溶劑分配層析(35)
2. 管柱層析與高效能液相層析(35)
3. 化合物結構鑑定(37)
(三)相思樹抽出物抗氧化與自由基清除活性之檢測(39)
1. DPPH自由基清除效應(39)
2. 超氧自由基捕捉試驗(NBT assay)(39)
3. 抑制脂質過氧化試驗(40)
4. 氫氧自由基清除效應(氫氧自由基引發DNA破壞試驗(41)
5. 過氧化氫清除效應(41)
(四)抽出成分酚類化合物總量測定(42)
(五)相思樹抽出物抗發炎機制之探討(43)
1. 抑制LPS誘導巨噬細胞產生一氧化氮自由基之生物檢測模式(43)
2. 抑制LPS誘導巨噬細胞產生前列腺素E2之生物檢測模式(44)
3. RT-PCR分析(44)
肆、結果與討論(47)
一、相思樹各部位乙醇抽出物之抗氧化活性 (47)
(一)DPH自由基清除效應(47)
(二)超氧自由基清除效應(49)
(三)脂質過氧化之抑制效應(52)
(四)氫氧自由基清除效應(氫氧自由基引發DNA破壞試驗)(55)
(五)過氧化氫清除效應(細胞抗氧化活性試驗)(57)
二、相思樹各部位乙醇抽出物之總酚含量(59)
三、相思樹抗氧化活性成分之分離與純化(61)
四、相思樹心材主要黃酮類化合物之含量及其抗氧化活性之比較(145)
五、酚類化合物抗氧化力與其結構之關係(148)
(一)黃酮類化合物(148)
(二)苯甲酸類化合物(153)
六、相思樹抽出物抗發炎機制之探討(157)
(一)相思樹不同部位乙醇抽出物及其抗氧化成分對LPS誘導巨噬細胞產生一氧化氮之影響(157)
(二)相思樹心材抗氧化成分Melanoxetin對LPS誘導巨噬細胞產生前列腺素E2之影響(166)
(三)Melanoxetin抑制LPS誘導巨噬細胞iNOS mRNA之表現(168)
(四)Melanoxetin抑制LPS誘發巨噬細胞COX-2 mRNA之表現(171)
伍、結論與建議(174)
陸、參考文獻(177)
柒、附錄–博士班修業期間之研究成果(1998-2004年)(188)


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