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    Please use this identifier to cite or link to this item: http://ir.cnu.edu.tw/handle/310902800/9249


    標題: N-(羥基苯)多羥基苯醯胺化合物之抗氧化與抑制酪胺酸酶之活性研究
    Studies on the Antioxidant and Tyrosinase Inhibitory Activityof N-(Hydroxy-phenyl) polyhydroxy benzamides
    作者: 張嘉苓
    Chia-ling Chang
    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: N-(羥基苯)多羥基苯醯胺化合物
    抗氧化
    美白
    化粧品
    Cosmetic
    Whitening
    Antioxidant
    N-(Hydroxyl-phenyl) polyhydroxy benzamides
    日期: 2007
    上傳時間: 2008-12-03 11:17:46 (UTC+8)
    摘要: 本研究主要利用有機合成方法,將具有不同數量及在不同位置之羥基取代之安息香酸及咖啡酸分別與胺基苯酚(aminophenol)化合物進行醯胺化反應,得到一系列高產率之多酚醯胺類衍生物(1~40),經由下列不同活性測試方法,探討其化粧品上的應用價值。一、清除DPPH自由基能力測試;二、清除過氧化氫自由基能力測試;三、抑制酪胺酸酶( Tyrosinase )活性測試。
    多酚醯胺化合物在清除DPPH自由基結果顯示,其清除DPPH自由基的能力與羥基數量及其取代位置有關,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,另外,羧酸苯環上二羥基取代位置互為鄰位或對位時,其抗氧化能力明顯較間位強。而當多酚醯胺化合物其抗氧化能力與Trolox差不多時(IC50 =13.90 μg/ml),胺基苯環上之羥基取代對整體抗氧化能力影響不明顯,但在羧酸苯環上具單羥基時,其清除自由基能力明顯下降,使得胺基苯環上羥基取代發揮了影響力,無羥基取代時,抗氧化能力最差,而羥基與胺基互為鄰位或是對位時較間位有提升效果。
    多酚醯胺化合物在抑制過氧化氫活性結果,皆有良好抑制效果且明顯與羥基取代數量有關;當羧酸苯環上具有三羥基或二羥基取代之醯胺化合物(IC50 = 0.18~17.02 μg/ml)普遍其抗氧化力較單羥基取代時比Trlox (IC50 = 12.06 μg/ml)之抑制過氧化氫活性能力強,但也有少釣狴~,如(Compound 25之IC50 = 53.96 μg/ml、Compound 28之IC50 = 45.77 μg/ml及Compound 33之IC50 = 30.56 μg/ml)。
    多酚醯胺化合物在美白活性結果,抑制酪胺酸酶活性評估,以咖啡酸、沒食子酸及2, 5-二羥基苯甲酸之醯胺衍生物效果最為顯著(IC50 = 62.41~130.28 μg/ml),但也有少酗坐X物顯示出明顯抑制酪胺酸酶活性能力,如(Compound 12之IC50 = 71.70 μg/ml、Compound 24之IC50 = 57.26 μg/ml)也出現較強之抑制酪胺酸酶活性能力。
    由以上實驗總結歸納:多羥基苯醯胺化合物以20、24、34、37、39及40同時在清除DPPH自由基、抑制過氧化氫及抑制酪胺酸酶活性皆具有極強能力,值得進一步探討其應用於抗老化兼具美白化粧品之有效成分。
    This research utilizes the method of organic synthesis to put different amount of aminophenol into hydroxybenzoic acid or caffeic acid so as to produce a series of high yield of polyhydroxy benzamides (1~40).Through the following different activity tests, discussing the applied value of cosmetics.Ⅰ. The experiment of their ability to scavenge DPPH free radical, Ⅱ. The test of inhibitory activity of H2O2, Ⅲ. The activity test of inhibit Tyrosinase.
    The result of scavenging DPPH free radical by the polyhydroxy benzamides:
    The ability to scavenge DPPH free radical which is related to the amount of substitution of hydroxy groups and their positions. The more hydroxy groups substituted at the carboxylic acid benzene ring, the scavenging of DPPH free radical is more stronger, otherwise, the substitution of two hydroxy groups are at the ortho-position or para-position of carboxylic acid benzene ring, the ability of antioxidant is apparently more stronger. And the ability of antioxidant of polyhydroxy benzamides don’t have too many differences with Trolox (IC50 =13.90 μg/ml), the substition of hydroxy group at amino benzene ring doesn’t affect the whole ability of antioxidant apparently, but while the single hydroxy group at carboxylic acid benzene ring, they are apparently decrease to scavenge the ability of free radical, as a result, the hydroxy at amino benzene ring substitutes its function, without the hydroxy group, the ability of antioxidant is worst, but it upgrades its function while the hydroxy and amino are in the ortho-position or para-position.
    In the evaluation of polyhydroxy benzamides inhibit H2O2, both of them have better depressing effect and related to the amount of the substitution of hydroxy groups at the carboxylic acid benzene ring for the antioxidant activity are more stronger than Trolox (IC50 = 12.06 μg/ml), but a few of them is exception, (ex: IC50 = 53.96 μg/ml of compound 25, IC50 =45.77 μg/ml of compound 28 and IC50 =30.56 μg/ml of compound 33).
    The result of polyhydroxy benzamides for whitening, the activity evaluation of tyrosinase inhibitory, it has apparently effect on the caffeic acid, gallic acid and 2, 5-dihydroxybenzoic acid of amide derivatives (IC50 = 62.41~130.28 μg/ml), but some of the compounds show apparently the activity of tyrosinase inhibitory, (ex:IC50 = 71.70 μg/ml of compound 12 and 57.26 μg/ml of compound 24) inhibitory efficacy.
    Form the experiment, the compounds 20、24、34、37、39 and 40 of Poly-
    hydroxy benzamides have powerful activity to scavenge of DPPH free radical, inhibitory activity of H2O2 and tyrosinase, They are worthy to discuss the effective function which applied for anti-aging and whitening cosmetics.
    關聯: 校內公開,校外永不公開
    Appears in Collections:[化妝品應用與管理系(所)] 博碩士論文

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