臺灣博碩士論文加值系統

薏苡自古以來便為藥食兼備的食材，許多中國傳統的藥書中對於其功效諸多記載。1950年代起，日本學者對薏苡開始進行一連串科學實驗，已有初步結果證明薏苡具有多項功能性。本實驗室自民國七十八年起致力於薏苡保健機能方面之研究，至目前為止，證明薏苡在抗致突變性、抗腫瘤、 降血脂和調節免疫力均有成效，但對於其有效成分並不明瞭。除此之外，許多的研究顯示上述多種機能可能與自由基多寡有關。故本實驗的目的為以薏苡殼為原料，探討其甲醇萃取物中有效清除自由基的化合物，並以此等化合物進行清除DPPH自由基模式其它抗氧化模式之研究。
實驗結果顯示，薏苡殼甲醇萃取物（AHM）清除DPPH自由基的能力明顯高於薏苡籽實其它部位之甲醇萃取物，其中又以經分配層析後的乙酸乙酯層（AHM-EA）和正丁醇層（AHM-B）效果最佳。乙酸乙酯層經純化所得的十七種化合物中包含二種類固醇，一種長鏈醇與十四種酚類化合物。經過清除DPPH自由基試驗，確定五種有效成分，分別4-hydroxy-3,5-dimethoxy-(E)-cinnamaldehyde（7）、4-oxo-inoresinol（11）、mayuenolide（12）、5-hydroxyindole-3-carbaldehyde（16）和dehydrodiconifreyl alcohol（17），在系統濃度為250μg/mL時，DPPH自由基的清除率均可達到60%以上， mayuenolide（12）的清除率更可達到90%。在還原力與抗氧化性測定模式中，各化合物作用能力趨勢與清除DPPH自由基能力並不完全相同，其中以mayuenolide（12）的作用能力最為穩定，在不同模式中均有很好的成效。
4-oxo-inoresinol（11）、mayuenolide（12）與lehydrodiconifreyl alcohol（17）同為木酚素（lignans），實驗結果顯示，木酚素在各測定模式中要比其它類化合物的作用能力強，且穩定許多。

Adlay has been used as an essential material both in drugs and foods for a long time. There were many reports about its function in old Chinese traditional herb books. A series of scientific experiments of adlay was reported by Japanese scholars from 1950s, and many functions were proved initially. From 1989, our laboratory was engaged in the study of adlay’s biological function. We have found that it’s efficient in anti-mutagenic, anti-tumor, decreasing the lipemia and the control of the immunity so far. But it’s not clear about its effective components. Besides, many studies revealed that all mechanisms mentioned above may be associated with the amounts of formation of free radicals. The purpose of this study was to isolate and identify active components of free radical scavenger from the methanolic adlay hull extract, and to test their antioxidative and free radicals scavenging activity using suitable models.
The results of this experiment revealed the efficiency of scavenging DPPH free radicals in AHM(adlay hull methanol extract) was higher than those of other parts of adlay. The most effective fractions were the ethyl acetate layer and the 1-butanol layer after partition of AHM. Seventeen pure compounds were isolated from the ethyl acetate layer, which included two steroids, one long chain fatty alcohol and fourteen phenolic compounds. Five active compounds were confirmed by the test of scavenging DPPH free radicals, and they were hydroxy-3,5-dimethoxy-(E)-cinnamaldehyde(7), 4-oxo-inoresinol(11), mayuenolide(12), 5-hydroxyindole-3-carbaldehyde (16) and dehydrodiconifreyl alcohol(17). The DPPH free radical scavenging effiency reached higher than 60%, and mayuenolide(12) was higher than 90%. The abilities of reducing power and antioxidative test of each compound were not the same trend with scavenging DPPH free radicals. The ability of mayuenolide(12) was the most stable and it had good ability in each testing model.
4-Oxo-inoresinol(11), mayuenolide(12) and dehydrodiconifreyl alcohol(17) are all lignans. The experimented result revealed lignans were more powerful than other kinds of compounds in all testing models.

中文摘要……………………………………………………………………..I
英文摘要……………………………………………………………………..II
目錄………………………………………………………………………….III
圖次…………………………………………………………………………..V
表次………………………………………………………………………...VII
縮寫表……………………………………………………………………..VIII
壹、 前言………………………………………………………………1
貳、 文獻整理…………………………………………………………2
一、自由基與活性氧…………………………………………………………2
（一）、何謂自由基………………………………………………………….2
（二）、體內常見自由基與活性氧的種類………………………………….2
（三）、體內自由基的來源………………………………………………….8
（四）、自由基對生物體的影響…………………………………………….9
（五）、細胞內清除自由基的酵素系統……………………………………10
1. Superoxide dismutase (SOD)……………………………………10
2. Catalase…………………………………………………………..11
3. Glutathione peroxidase (GSHp)………………………………….11
（六）、其它可能清除自由基的機制………………………………………12
二、薏苡……………………………………………………………………..14
（一）、薏苡之簡介…………………………………………………………14
（二）、本實驗室薏苡機能性的研究成果………………………….……15
1. 輔助抑制腫瘤機能…………………………………………………...16
2. 改善腸道菌叢作用…………………………………………………...16
3. 抗致突變性…………………………………………………………...16
4. 降血脂作用…………………………………………………………...17
5. 抗過敏作用…………………………………………………………...17
參、 材料與方法………………………………………………….24
一、薏苡殼中化合物之分離與純化………………………………………..24
（一）、實驗藥品與器材……………………………………………………24
1. 原料來源………..………………….…………………………………24
2. 藥品………………...…………………………………………………24
3. 器材…………………………..….……………………………………24
（二）、實驗方法……………………………………………………………25
1. 原料製備…………………………………………………………………25
2. 甲醇萃取物的純化與分析………………………………………………26
3. 光譜儀器…………………………………………………………………27
二、薏苡殼甲醇萃取物之清除自由基試驗………………………………..28
（一）、實驗藥品與器材……………………………………………………28
1. 實驗樣品來源……………………………………………………………28
2. 藥品………………………………………………………………………28
3. 器材………………………………………………………………………28
（二）、實驗方法……………………………………………………………29
1. 清除DPPH自由基試驗……………………………………………………29
2. 還原力測定………………………………………………………………29
3. 抗氧化性測定……………………………………………………………29
肆、 結果與討論………………………………………………………32
一、薏苡殼甲醇萃取物乙酸乙酯層之成分與分析………….……………32
（一）、薏苡殼甲醇萃取物乙酸乙酯層分離結果………………..………32
（二）、化合物摘要………………………………………………….…….33
（三）、化合物之分析與鑑定………………………………………….…38
二、薏苡殼甲醇萃取物之清除自由基作用……………………………….101
（一）、清除DPPH自由基……………………………………………..….101
（二）、還原力測定…………………………………………………….…111
（三）、抗氧化性測定-硫氰酸鐵法……..………………………………113
（四）、化合物之討論……………………………………………………117
伍、 結論……………………………………………………………119
陸、 參考文獻………………………………………………………120

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