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    請使用永久網址來引用或連結此文件: https://ir.cnu.edu.tw/handle/310902800/9740


    標題: 合成羥基取代之N-酪胺桂皮醯胺衍生物探討其抗氧化及抑制酪胺酸活性之研究探討
    Studies on Synthesis of Hydroxy Subsituted of N-Cinnamoyltyramine Derivatives as Inhibitory Activity of Antioxidant and Tyrosinase
    作者: 曾維毅
    Wei-Yi Tseng
    貢獻者: 楊朝成
    嘉南藥理科技大學:化妝品科技研究所
    關鍵字: 抗老化
    美白
    醯胺化反應
    自由基
    抗氧化能力
    N-羥基苯酪胺桂皮醯胺衍生物
    free radical
    Benzamides reaction
    whitening
    Anit-aging
    Antioxidant
    Hydroxy Subsituted of N-Cinnamoyltyramine Deriva
    日期: 2008
    上傳時間: 2008-12-29 15:22:38 (UTC+8)
    摘要: 本研究主要利用有機合成的方法,將一系列不同數量及在不同位置的羥基取代之桂皮酸分別與酪胺及多巴胺進行醯胺化反應後,得到一系列的羥基取代之N-酪胺桂皮醯胺類衍生物(Compounds 1~16),再經由下列不同活性測試方法,探討其在化粧品上的應用價值。一、抗氧化活性清除DPPH自由基能力測試;二、總抗氧化能力—TEAC活性測試;三、抑制酪胺美白活性測試;四、紫外線/可見光光譜儀吸收測試。
    羥基取代之桂皮醯胺化合物在清除DPPH自由基試驗結果顯示,其清除DPPH自由基的能力與羥基數量及位置有關。當羧酸苯環上羥基取代數量越多,其清除DPPH自由基能力就越強;而羧酸苯環上二羥基取代時,其清除DPPH自由基能力比單羥基或單甲氧基取代的衍生物為佳。例如咖啡酸其具有兩個羥基取代且互為鄰位取代,所以具有很強的清除DPPH自由基能力;而當羧酸苯環上為單取代羥基時,不論是在哪一個位置有羥基取代,其清除DPPH自由基抗氧化能力並未有明顯的差異。而另一邊的胺基苯環上之羥基取代,二羥基取代的多巴胺其對清除DPPH自由基的能力比單羥基取代的酪胺強,尤其是酪胺系列的衍生物其羧酸苯環為單羥基取代時,其清除DPPH自由基的能力明顯下降。故可得到一個結論:在清除DPPH自由基能力測試上面,多巴胺優於酪胺的衍生物,其原因與胺基苯環上之羥基取代數目有關;尤其是咖啡酸與多巴胺合成反應之衍生物效果最強(Compound 9),其IC50 =8.08±1.09 μg/ml,另外咖啡酸與酪胺反應的衍生物其效果次之(Compound 1;IC50 =10.52±0.82 μg/ml)。
    羥基取代之N-酪胺桂皮醯胺類衍生物在總抗氧化能力—TEAC活性測試結果顯示,大部分衍生物皆有良好的抗氧化活性,除了多巴胺的甲氧基單取代衍生物(Compound 15,IC50 =10.18±0.43 μg/ml)明顯比標準對照組Trolox (IC50 =5.41±0.22 μg/ml)差之外,其餘皆比Trolox來的強。我們也可以從結構上羥基取代數量的關聯性來觀察出一些端倪:當羧酸苯環上具有二羥基取代之醯胺化合物時,普遍其抗氧化能力較單羥基取代的抗氧化能力來的強些,但差異並不顯著;而比較特別的是酪胺的甲氧基單取代衍生物(Compound 7)有不錯的清除能力。
    羥基取代之N-酪胺桂皮醯胺類衍生物在抑制酪胺酸美白活性測試結果,所合成的衍生物,均具有抑制酪胺酸的活性,其中以m-Coumaric acid、Isoferulic acid和 4-Methoxycinnamic acid之醯胺衍生物(Compounds 3、6、7、11)效果最為顯著。不論是多巴胺或酪胺為胺基苯環取代的衍生物,其抑制酪胺酸的活性皆比對照組維生素C(IC50=133.71±15.80)來的強;更甚之,m-Coumaric acid以及Isoferulic acid的酪胺衍生物(Compounds 3、6)其抑制酪胺酸的活性比麴酸(IC50=91.35±12.59)更強。
    羥基取代之N-酪胺桂皮醯胺衍生物在紫外線光譜儀吸收測試結果,其具有吸收UVB、UVC的防曬能力,在結構上具有C=C雙鍵結構者其防曬效能較佳。酪胺與多巴胺合成的衍生物來比較,其酪胺系列具有較佳的防曬效能,原因與胺基苯環上的羥基取代數目有關;羧酸苯環上只有單取代基時,其防曬效果會比雙取代基來的更佳;並且當羧酸苯環上R3的位置具有甲氧基取代時,如Compounds 7以及15(莫耳消光係數分別為93.67及83.50 L/mole*cm)其具有較強的防曬效果,而其結構與對照組Parsol MCX(莫耳消光係數為103.01 L/mole*cm)之化學結構式相似,其共通點是在它們的羧酸苯環上(R3)皆只有一個甲氧基的取代。
    This research utilized the method of organic synthesis to put different amounts and positions of Hydroxy-substituted Tyramine and Hydroxy-substituted Dopamine into Cinnamic acid or Caffeic acid so as to produce a series of Hydroxy-substituted N-Cinnamoyltyramine Derivatives (Compounds 1~16). Through the following tests, this research studies those compounds’ applied value of cosmetics. I. The activity of antioxidant and the experiment of ability to scavenge DPPH free radical, II. The ability of total antioxidant—the activity of TEAC, III. The activity test of inhibit Tyrosinase, IV. The ability to absorb UV in UV-Vis spectrometer.
    The result of scavenging DPPH free radical by the Hydroxy-substituted N-Cinnamoyltyramine Derivatives shows that the ability to scavenge DPPH free radical is related to the position of substitution of hydroxy group. The more hydroxy groups substituted at the carboxylic acid benzene ring, the stronger the ability to scavenge DPPH free radical. Moreover, Bi-Hydroxy substitution at the carboxylic acid benzene ring has the better ability to scavenge DPPH free radical than Mono-Hydroxy substitude derivatives or Methoxy substituted derivatives does. For example, Caffeic acid has Bi-Hydroxy substitution and orth-substitution, so that it has stronger ability to scavenge DPPH free radical. On the other hand, the carboxylic acid benzene ring which has only mono-hydroxy substituted is not significantly good at scavenging the DPPH free radical, no matter its position. On the contrary, at amino benzene ring, bi-Hydroxy substituted Dopamine have better ability to scavenge DPPH free radical than Hydroxy substituted, and the mono-Hydroxy substituted derivatives at carboxylic acid benzene ring, which is related to Tyramine, is not significantly able to scavenge the free radical. In sum, in the experiment of the ability to scavenge DPPH free radical, Dopamine derivatives are better than Tyramine derivatives, the fact of which is related to the amount of Hydroxy substitution at amino benzene ring. Moreover, the derivative (Compound 9) synthesized by caffeic acid and Dopamine is the best at scavenging DPPH free radical (IC50 =8.08±1.09 μg/ml), and the derivative synthesized by caffeic acid and Tyramine is second to it (Compound 1; IC50 =10.52±0.82 μg/ml).
    The results in the experiments of the ability of total antioxidant—the activity of TEAC—shows that, Hydroxy substituted N-Cinnamoyltyramine Derivatives all have good antioxidant activity. Almost each derivatives are stronger than controlled group, Trolox (IC50 =5.41±0.22 μg/ml), except Methoxy substituted derivatives (Compound 15, IC50 =10.18±0.43 μg/ml). We can infer the reason from the amount of Hydroxy substitution. When there is bi-Hydroxy substituted Benzamides derivatives at carboxylic acid benzene ring, the ability of antioxidant are normally stronger than mono substitution, but not significant. However, this study found that Methoxy substituted Tyamine derivatives (Compound 7) is pretty good at scavenging free radical.
    The result of applying Hydroxy substituted N-Cinnamoyltyramine Derivatives to inhibit tyrosinase and whitening shows that all the derivative have a activity to inhibit tyrosinase, and meta-Coumaric acid, Isoferulic acid, and 4-Methoxycinnamic acid’s Benzamides derivatives (compound 3, 6, 7, 11) have significant effects. Both Dopamine and Tyramine substitution at Amino benzene ring have stronger tyrosinase inhibition than Vitamin C (IC50=133.71±15.80). Further, meta-Coumaric acid and Isoferulic acid’s Tyramine derivatives (Compounds 3, 6) have strong inhibition than kojic acid (IC50=91.35±12.59).
    Hydroxy substituted N-Cinnamoyltyramine Derivatives are proven to be able to absorb UVB and UVC in UV-Vis spectrometer, especially when the derivatives are C=C structured. On the other hand, Tyramine derivatives have better ability to absorb UVB and UVC, compared with Dopamine, the fact of which results from the amount of hydroxy groups substituted at the carboxylic acid benzene ring, and the ability is better when Bi-substituted derivatives at the carboxylic acid benzene ring than Mono-substituted derivatives. Moreover, when there is Methoxy-substitution at R3 in carboxylic acid benzene ring, such as compound 7 and 15 (ε= 93.67 andε= 83.50 L/mole*cm, respectively), it is better at absorbing UVB and UVC. The result can be supported by the controlled group, Parsol MNX (ε= 103.01 L/mole*cm), which has similar structure— Methoxy-substitution at R3 in carboxylic acid benzene ring.
    關聯: 校內外均一年後公開
    顯示於類別:[化妝品應用與管理系(所)] 博碩士論文

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