臺灣博碩士論文加值系統

鴨舌癀為多年生草本植物，化學成分種類眾多，其中以黃酮類為主要成分。然而，植物的化學組成會受到不同地理環境及後生長因子等因素影響其一致性。因此，發展系統性的品質控管方法是必要的。本研究藉由DPPH、ABTS、黃嘌呤/黃嘌呤氧化酶及酪胺酸酶系統評估鴨舌癀之抗氧化及酪胺酸酶抑制效果並探討結構與活性之關係。另外以高壓液相層析搭配紫外/可見光偵測器的方法同時建立鴨舌癀之指紋圖譜並定量onopordin (4)及eupafolin (7)二個活性成分。鴨舌癀地上部經由管柱層析分離，共分離得到七個已知化合物，包括3,7,4'',5''-tetrahydroxy-3''-methoxyflavone (1)、nodifloretin (2)、4''- hydroxywogonin (3)、onopordin (4)、cirsiliol (5)、5,7,8,4''-tetrahydroxy-3''- methoxyflavone (6)及eupafolin (7)。其中onopordin (4)、cirsiliol (5)及eupafolin (7)因為B環上有兒茶酚結構而呈現良好的自由基清除效果。在酪胺酸酶抑制實驗，化合物4及7的抑制能力分別為熊果素的1.8倍及2.2倍。在定量分析中，二個分析物皆具有良好的線性(R2 > 0.9994)、精密度(相對標準偏差小於6.99%)及準確度。結果顯示鴨舌癀具有良好的抗氧化及酪胺酸酶抑制活性，且所發展的分析方法可作為日後鴨舌癀添加在化粧品或保健食品上定性定量的參考依據。

Phyla nodiflora (L.) Greene is a perennial herb containing various chemical constituents, which are abundant in flavonoids as major components. However, the consistency of phytochemical profile might be affected by different geography conditions and post-growth factors. Thus, a systematic quality criterion for controlling the quality of P. nodiflora is imperative. In the study, the antioxidant and antityrosinase activities of P. nodiflora were estimated by DPPH, ABTS, xanthine/xanthine oxidase, and tyrosinase systems and revealed some structure-activity relationships. Besides, a method combined with high- performance liquid chromatography (HPLC) with UV/Vis detector was developed for simultaneous chemical fingerprint and quantification of two active compounds, known as onopordin (4) and eupafolin (7). By separated with silica column chromatography, seven known compounds, 3,7,4'',5''-tetrahydroxy-3''- methoxyflavone (1), nodifloretin (2), 4''-hydroxywogonin (3), onopordin (4), cirsiliol (5), 5,7,8,4''-tetrahydroxy-3''-methoxyflavone (6), and eupafolin (7), were isolated from P. nodiflora. Onopordin (4), cirsiliol (5), and eupafolin (7) containing with catechol moiety in the ring B showed good radical scavenging abilities. In tyrosinase inhibitory assay, the activities of compounds 4 and 7 were 1.8-times and 2.2-times stronger than arbutin. In quantitative analysis, two analytes showed good linearity (R2 > 0.9994), precision (relative standard deviation < 6.99%) and accuracy. The results indicated that P. nodiflora possess good antioxidant and antityrosinase potentials and the developed fingerprint could further serve for quality and quantity of P. nodiflora added in cosmetic industry and health food.

目錄...................................................................................................... Ⅰ
圖目錄.................................................................................................. Ⅲ
表目錄.................................................................................................. Ⅴ
中文摘要................................................................................................ 1
Abstract ................................................................................................. 2
第一章 序論.......................................................................................... 3
第1-1節 前言與研究目的............................................................... 3
第1-2節 研究背景........................................................................... 9
第1-2-1項 馬鞭草科(Verbenaceae)植物介紹............................ 9
第1-2-2項 鴨舌癀(Phyla nodiflora (L.) Greene)植物介紹...... 10
第二章 材料與研究方法..................................................................... 22
第2-1節 儀器與材料..................................................................... 22
第2-2節 萃取與分離..................................................................... 26
第2-3節 化合物之物理化學性質................................................. 30
第2-4節 生物活性試驗篩選方法................................................. 35
第2-4-1項 總酚含量評估.......................................................... 35
第2-4-2項 抗氧化能力之評估.................................................. 37
第2-4-3項 酪胺酸酶活性抑制試驗.......................................... 42
第2-4-4項 酵素動力學.............................................................. 43
第2-5節 指紋圖譜......................................................................... 45
第2-6節 統計方法......................................................................... 47
第三章 結果與討論............................................................................. 48
第3-1節 化合物之結構解析......................................................... 48
第3-1-1項 3,7,4'',5''-Tetrahydroxy-3''-methoxyflavone (1)之
結構證明.................................................................. 48
第3-1-2項 Nodifloretin (2)之結構證明.................................... 51
第3-1-3項 4''-Hydroxywogonin (3)之結構證明....................... 55
第3-1-4項 Onopordin (4)之結構證明....................................... 59
第3-1-5項 Cirsiliol (5)之結構證明........................................... 63
第3-1-6項 5,7,8,4''-Tetrahydroxy-3''-methoxyflavone (6)之
結構證明................................................................... 67
第3-1-7項 Eupafolin (7)之結構證明......................................... 71
第3-2節 鴨舌癀粗抽物活性試驗結果與討論.............................. 74
第3-2-1項 鴨舌癀粗抽物總酚含量評估............................. 74
第3-2-2項 鴨舌癀粗抽物抗氧化能力試驗......................... 75
第3-2-3項 鴨舌癀粗抽物還原能力試驗............................. 80
第3-2-4項 鴨舌癀粗抽物酪胺酸酶抑制試驗..................... 81
第3-2-5項 鴨舌癀活粗抽物性試驗總結............................. 81
第3-3節 化合物活性試驗結果與討論.......................................... 83
第3-3-1項 抗氧化能力試驗結果......................................... 83
第3-3-2項 酪胺酸酶抑制試驗結果..................................... 89
第3-3-3項 酵素動力學......................................................... 91
第3-3-4項 討論..................................................................... 93
第3-4節 指紋圖譜........................................................................... 99
第3-4-1項 層析條件之探討........................................................ 99
第3-4-2項 層析方法確認.......................................................... 103
第3-4-3項 不同批次樣品比較.................................................. 105
第四章 結論......................................................................................... 107
第五章 參考文獻................................................................................. 109
第六章 附件......................................................................................... 120

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