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| 題名: | (一) 樟葉槭之成分研究 (二) 兒茶酚衍生物於人類黑色素細胞活性探討 |
| 作者: | 黃靜儀 |
| 貢獻者: | 生藥學研究所 |
| 日期: | 2010 |
| 上傳時間: | 2010-10-20 13:05:43 (UTC+8) |
| 摘要: | 樟葉槭 (Acer albopurpurascens Hayata) 為楓科 (Aceraceaez) 常綠喬木，台灣特有種，分布於台灣全島低至中海拔山區。本論文第一部分乃採集樟葉槭之葉部，以95%乙醇萃取，進行成分分離。經管柱層析分離純化得到七個化合物，經由光譜分析與文獻比對。結構為
chlorgenic acid methyl ester (1)、(-)-epicatechin (2) tricin-7-O-β-D-glucopyranoside (3)、tricin-4´-O-β-D-glucopyranoside (4)、quercetin (5)、dendratnhemoside
A (6) 和 dihydrodendranthemoside A (7)。第二部分為探討由白花水竹草 (Trandescantia albiflora Kunth) 所分出七種兒茶酚
(catechol) 化合物及其半合成衍生物，對人類正常黑色素細胞抑制黑色素生成的活性。此十六種化合物於100 μM濃度下對於人類正常黑色素細胞之細胞存活率皆大於80%，進一步進行細胞內酪胺酸酵素活性測試，結果顯示化合物AR9 及AR10 具最佳之酪胺酸酵素抑制活性，其 IC50 分別為 81.1及 90.7 μM；以西方墨點法分析，結果顯示AR9 具有抑制酪胺酸酵素和酪胺酸相關蛋白酵素-2 蛋白質之表現，而AR10 具有抑制酪胺酸酵素蛋白質之表現，對於酪胺酸相關蛋白酵素-1 及酪胺酸相關蛋白酵素-2 則無明顯作用。另外以細胞免疫染色法觀察亦有相同的結果。
Acer albopurpurascens Hayata is an evergreen and endemic species in Taiwan. It was found widely throughout the island and from the low lands up to an altitude of 1800 m. The fresh leaves of A. albopurpurascens were extracted with 95% ethanol at room temperature. After filtering and
concentrating under reduced pressure, the 95% ethanolic extraet was partitioned with a sequence of n-hexane, ethyl acetate (EtOAc), and n-butanol (n-BuOH), and water to give four fractions. The EtOAc and n-BuOH extracts were subject to gel filtration and reversed-phase chromatography to obtain seven known compounds. These known
compounds were identified as chlorgenic acid methyl ester (1), (-)-epicatechin (2), tricin-7-O-β-D-glucopyrano-side (3), tricin-4´-O-β-Dglucopyranoside (4), quercetin (5), dendranthemoside A (6) and dihydrodendranthemoside A (7) by comparison of spectroscopic data of the literature or authentic sample.
Part 2 is study seven compounds isolated from Trandescantia albiflora Kunth and five compounds of catechol derivatives by chemical synthesis. Those 16 compounds were further evaluated their abilities to inhibit cellular melanin synthesis in human epidermal melanocytes (HEMn). Cell viabilities of 16 compounds were higher then 80%, when cells were treated with 100 μM of different compounds. The 16 compounds were further evaluated their cellular tyrosinase activity in HEMn, and the compounds AR9 and AR10 were the most potent in inhibiting tyrosinase activity. The copmounds AR9 and AR10 IC50 were 81.1 and 90.7 μM respective. Results of the protein expression of cellular tyrosinase and TRP-2 showed AR9 X possessed significant inhibitory effects by blotting analysis, and tyrosinase
showed AR10, too. |
| 關聯: | 119頁 |
| 描述: | 目錄 .................................................... Ⅰ
圖目錄 .................................................. Ⅲ
表目錄 .................................................. Ⅶ
中文摘要 ........................................... Ⅷ
英文摘要 ................................................ Ⅸ
第一部份：樟葉槭之成分研究 .............................. 1
第一章 緒論 ............................................. 2
一、 樟葉槭基本介紹 ..................................... 2
二、 槭屬植物相關介紹 ................................... 2
三、 槭屬植物活性研究回顧.................................5
四、 槭屬植物之化學成分研究 ............................. 7
五、 研究動機 ........................................... 16
第二章 實驗材料與方法 ................................... 17
一、 樟葉槭之萃取與分離 ................................. 17
(一) 一般試藥及溶媒...................................... 17
(二) 色層分析之材料 ..................................... 17
(三) 儀器 ............................................... 18
(四) 樟葉槭萃取及分離流程 ............................... 19
(五) 各成分之物理數據 ................................... 21
第三章 結果與討論 ........................................26
一、 樟葉槭之化合物及其結構鑑定 ......................... 26
(一) Chlorogenic acid methyl ester (1) 之結構解析 ....... 26
(二) (-)-Epicatechin (2) 之結構解析 ..................... 29
(三) Tricin-7-O-β-D-glucopyranoside (3) 之結構解析 ..... 32
(四) Tricin-4′-O-β-D-glucopyranoside (4) 之結構解析 ... 36
(五) Quercetin (5) 之結構解析 .......................... 39
(六) Dendranthemoside A (6) 之結構解析 ................. 40
(七) Dihydrodendranthemoside A (7) 之結構解析........... 44
結論 ................................................... 47
第二部份：兒茶酚衍生物於人類黑色素細胞活性探討 ......... 49
II第一章 緒論 .......................................... 50
一、 人類黑色素細胞 (Melanocytes) ...................... 50
二、 黑色素 (Melanin) .................................. 50
三、 酪胺酸酵素 (Tyrosinase) ........................... 51
四、 黑色素之生化合成 (Melanogensis) ................... 52
五、 抑制黑色素生成的方法 .............................. 52
六、 酪胺酸酵素動力學機制之研究 ........................ 53
七、 十六種兒茶酚衍生物之介紹 .......................... 55
八、 十六種兒茶酚衍生物活性之研究回顧 .................. 56
九、 研究動機 .......................................... 58
第二章 實驗材料與方法 .................................. 59
一、 化學合成化合物之活性實驗部份 ...................... 59
(一) 一般藥品與試劑 .................................... 59
(二) 細胞株及細胞培養液 ................................ 60
(三) 實驗抗體 .......................................... 60
(四) 活性儀器設備 ...................................... 61
(五) 分析軟體 ...........................................61
(六) 人類黑色素細胞培養 ................................ 61
(七) 細胞存活率試驗 .................................... 62
(八) 蛋白定量法 ........................................ 62
(九) 細胞內酪胺酸酵素活性試驗 ...........................63
(十) 西方墨點法 ........................................ 63
(十一) 免疫螢光染色試驗 ................................ 64
第三章 結果與討論 ...................................... 66
一、 十六種兒茶酚衍生物之活性探討 ...................... 66
(一) 細胞存活率試驗 .................................... 66
(二) 人類黑色素細胞內酪胺酸酵素活性試驗................. 66
(三) 人類黑色素細胞內酪胺酸酵素之西方墨點法試驗 ........ 67
(四) 人類黑色素細胞內酪胺酸酵素相關蛋白表現之免疫螢光染色
法試驗 ................................................. 69
結論 ................................................... 72
第四章 參考文獻 ........................................ 74
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