臺灣博碩士論文加值系統

台灣紅豆杉(Taxus mairei)又稱南洋紅豆杉(Taxus sumatrana)，紅豆杉科，紅豆杉屬，為裸子植物，是台灣貴重針葉五木之一。許多研究表示，紫杉醇藥物對於腫瘤尤其是卵巢癌和轉移性乳腺癌有效，如同其它化學治療一般，紫杉醇也有許多藥物毒性，較常見的毒性包括急性過敏反應。台灣紅豆杉萃取液來自於枝葉萃取物，目前已有商業化產品，由於有關紅豆杉的研究幾乎都著重於抗癌成分，對於其枝葉所含功效成分卻缺乏相關科學佐證資料。礙於紫杉醇的副作用，本研究利用高效液相層析儀(HPLC)為基礎，確定萃取液樣品中內不含紫杉醇及其前驅物(10-DAB)化合物，透過分析方法確認萃取液中功能性成分，總萜含量0.393±0.010 mg/mL、總酚含量0.448±0.020 mg/mL、總黃酮含量0.032±4.5×10⁻⁴ mg/mL。傅立葉紅外線光譜儀(FT-IR)建立特性光譜圖，結果在3367, 2927, 1603, 1516, 1384, 1265, 1052 cm⁻¹處有特徵峰，顯示樣品中可能含有酚類(3367~3345 cm⁻¹, 1268~1265 cm⁻¹)、黃酮類(1603~1595 cm⁻¹ and 1514~1516 cm⁻¹)及萜類(2939~2927 cm⁻¹)。以半製備型HPLC分為四區進行收集，從生物活性試驗較佳之片段三，收集該區間各單一化合物，透過LC/MS、GC/MS、¹H-NMR、¹³C-NMR及FT-IR等分析鑑定，實驗結果得到兩個化合物皆為酚類化合物。

Taxus mairei is also known as “Taxus sumatrana”, it belongs to the family of Taxaceae. T. mairei is a gymnosperm plant, one of the five valuable woods of conifer leaves and the national treasure varieties in Taiwan. The extraction of T. mairei is the first-found main source of paclitaxel. Several studies have shown that the paclitaxel which is also named taxol drug is effective against tumors, especially ovarian cancer and metastatic breast cancer and other types of solid tumor cancers. Yet paclitaxel also has many kind of drug toxicities, the most common allergic reactions such as acute toxicity. T. mairei extract which is derived from the branch and leaves is found there is still a lot of other commercial products. Since studies on T. mairei almost exclusively focus on anti-cancer components, there is a lack of research on the other functional components contained in the branch and leaf. A research confirmed by HPLC analytical technique show the result that T. mairei's leaves and branch extract solvent didn't detect any presence of paclitaxel. The solvent extraction contains functional compositions, which has confirmed by analytical methods. Preliminarily results showed that total phenol content was found to be 0.393±0.010 mg/mL of gallic acid equivalents, total triterpenes content was found to be 0.448±0.020 mg/mL of ursolic acid equivalents and total flavonoids content was found to be 0.032±4.5×10⁻⁴ mg/mL of quercetin equivalents in the crude extract of T. mairei. Fourier transform infrared spectroscopy (FT-IR) was employed to characterized the extract of T. mairei. The adsorption peaks were observed at 3367, 2927, 1603, 1516, 1384, 1265, 1052 cm⁻¹ correspond to the phenols (3367-3345 cm⁻¹, 1268-1265 cm⁻¹), flavonoids (1603-1595 cm⁻¹) (1514-1516 cm⁻¹) and terpene (2939-2927 cm⁻¹). The semi-preparative HPLC was used to collect four fractions and the fragment 3 was found to be the best activity. The compounds were identified by LC/MS, GC/MS, ¹H-NMR, ¹³C-NMR and FT-IR. As a result, both compounds were phenolic compounds.

目錄
中文摘要 ................................ I
Abstract ................................ II
致謝 …………………………………………………… ………………………IV
目錄 …………………………………………………… …………………………………………… VI
表目錄 ................................ VIII
圖目錄 ................................ IX
第一章 緒論............................1
1-1 前言...............................1
1-2 研究目的...........................2
第二章 文獻回顧........................3
2-1 紅豆杉..............................3
2-1-1 台灣紅豆杉簡介.....................3
2-1-2 紅豆杉植物型態與分類...............5
2-1-3 紫杉醇與前驅物10-去乙醯巴卡亭III....6
2-1-4 台灣紅豆杉成分.....................9
2-1-4.1 萜類化合物.......................9
2-1-4.2 紫杉烷類化合物...................11
2-1-4.3 酚類和木脂素類化合物.............18
第三章 紅豆杉萃取液功能性成分分析探討.....22
3-1 前言................................22
3-2 材料與方法...........................23
3-2-1 實驗材料與設備.....................23
3-2-2 實驗方法..........................25
3-2-2.1 紫杉醇與前驅物10-DAB測試..........25
3-2-2.2 定量顯色分析.....................27
3-2-2.3 建立特性光譜.....................30
3-3 結果與討論...........................31
3-3-1 紫杉醇與10-DAB之確認................31
3-3-2 定量分析...........................35
3-3-3 特性光譜...........................37
3-4 結論..................................42
第四章 紅豆杉萃取液之分離純化...............43
4-1 前言..................................43
4-2 材料與方法.............................44
4-2-1 實驗材料與設備.......................44
4-2-2 實驗方法............................45
4-2-2.1 HPLC梯度分離......................45
4-2-2.2 樣品液-液萃取.....................46
4-2-2.3 分析鑑定條件......................48
4-3 結果與討論............................50
4-3-1 HPLC分離...........................50
4-3-2 樣品液-液萃取.......................54
4-3-3 結構分析與鑑定......................57
4-4 結論.................................75
第五章 總結與未來展望....................76
參考文獻.................................78
作者簡歷.................................85

表目錄
表2-1、台灣紅豆杉中二萜類化合物成分..........10
表2-2、台灣紅豆杉中紫杉烷類二萜化合物成分.....13
表2-3、台灣紅豆杉中酚類和木脂素類化合物成分...20
表3-1、紅豆杉萃取液定量顯色試驗之成分含量.....36

圖目錄
圖.2-1 台灣紅豆杉(A)胸徑超過1公尺的臺灣紅豆杉樹(B)紅豆杉全株...4
圖.2-2 台灣紅豆杉枝葉與種子...4
圖.2-3 紫杉醇(Taxol)化學結構...8
圖.2-4 10-去乙醯巴卡亭III (10-DAB)化學結構...8
圖.2-5 紫杉烷類二萜化合物基本架構...12
圖.3-1 紫杉醇與10-DAB之UV全波長圖...32
圖.3-2 紅豆杉萃取液(水萃A、蒸餾B)與紫杉醇之HPLC層析圖...33
圖.3-3 紅豆杉萃取液(水萃A、蒸餾B)與10-DAB之HPLC層析圖...34
圖.3-4 沒食子酸之FT-IR光譜圖...38
圖.3-5 槲皮素之FT-IR光譜圖...39
圖.3-6 熊果酸之FT-IR光譜圖...40
圖.3-7 紅豆杉萃取液之FT-IR光譜圖...41
圖.4-1 樣品液液分配萃取流程圖...47
圖.4-2 紅豆杉萃取液之UV全波長圖...51
圖.4-3 紅豆杉萃取液之半製備HPLC層析圖...52
圖.4-4 紅豆杉萃取液之分析型HPLC層析圖...53
圖.4-5 液-液萃取之分析型HPLC圖譜(A)正己烷層(B)二氯甲烷層(C)乙酸乙酯層(D)水層...55
圖.4-6 二氯甲烷層之半製備型HPLC圖譜...56
圖.4-7 peak-B之分析型HPLC層析圖...58
圖.4-8 peak-B之LC/MS圖譜...59
圖.4-9 peak-B之GC-FID層析圖...60
圖.4-10 peak-B之GC/MS層析圖...60
圖.4-11 peak-B之GC/MS圖譜(A) peak-B3；(B) peak-B2；(C) peak-B1...61
圖.4-12 peak-B1之GC/MS資料庫比對結果...62
圖.4-13 peak-B中含peak-B1之1H-NMR圖譜...63
圖.4-14 對羥基苯甲醛標準品之1H-NMR圖譜...65
圖.4-15 peak-B1之13C-NMR圖譜(A)預測圖；(B)樣品圖...66
圖.4-16 peak-B1之FT-IR光譜圖...67
圖.4-17 peak-B2之GC/MS資料庫比對結果...68
圖.4-18 peak-B3之GC/MS資料庫比對結果...70
圖.4-19 peak-B中含peak-B3之1H-NMR圖譜...71
圖.4-20 peak-B3之13C-NMR圖譜(A)預測圖；(B)樣品圖...72
圖.4-21 對3-(4-羥基苯基)-1-丙醇標準品之1H-NMR圖譜...73
圖.4-22 peak-B3之FT-IR光譜圖...74

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