根皮苷及苹果幼果多酚对酪氨酸酶活性的抑制作用
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摘要
为比较苹果幼果多酚及其主要组分根皮苷作为酪氨酸酶抑制剂的潜质,本文以曲酸为阳性对照,分析并比较了三者对酪氨酸酶的抑制效果及抑制动力学。结果表明,根皮苷、苹果幼果多酚和曲酸均能有效抑制酪氨酸酶单酚酶及二酚酶活性,三者抑酶效果的强弱顺序为曲酸>苹果幼果多酚>根皮苷,对单酚酶活性的IC50分别为55.80、54.30和23.81μg/m L,对二酚酶活性的IC50分别为75.30、56.15和23.45μg/m L;根皮苷浓度为200μg/m L时为竞争型抑制,低于200μg/m L时为混合型抑制,苹果幼果多酚为非竞争型抑制,曲酸为混合型抑制。因此,抑制剂的组成成分和浓度均能影响其抑酶效果和抑酶机理,三种抑制剂均可通过抑制酪氨酸羟化生成多巴及抑制多巴氧化成多巴醌来减少黑色素的合成,苹果幼果多酚对酪氨酸酶活性的抑制效果优于根皮苷,且含量丰富,价格便宜,更适合作为酪氨酸酶抑制剂,有望开发应用于美白产品中。
To compare the potential of young apple polyphenols and phlorizin as tyrosinase inhibitors, the inhibitory effect and kinetics of phlorizin, young apple polyphenols and kojic acid on tyrosinase activity were analyzed and compared by spectrophotometry, in which kojic acid was used as a positive control. Results: phlorizin, young apple polyphenols and kojic acid could effectively inhibit tyrosinase activity. The order of their inhibitory effects was kojic acid>young apple polyphenols>phloridin, and their IC50 for monophenolase activity was 55.80, 54.30 and 23.81 μg/m L, respectively, and their IC50 for diphenolase activity was 75.30, 56.15 and 23.45 μg/m L, respectively. The phlorizin showed mixed inhibition at a concentration lower than 200 μg/m L and competitive inhibition at a concentration of 200 μg/m L, the young apple polyphenols showed non-competitive inhibition and the kojic acid showed mixed inhibition. In summary, the inhibitory effect and inhibitory mechanism of the inhibitor is not only related to its composition, but also related to its concentration. All three inhibitors can reduce the synthesis of melanin by inhibiting the hydroxylation of tyrosine to dopa and the oxidation of dopa to dopaquinone and dopachrome. Compared with phlorizin, young apple polyphenols is more suitable as tyrosinase inhibitors and has great potential for application in whitening products because of its better inhibitory effect, cheaper price and richer content.
To compare the potential of young apple polyphenols and phlorizin as tyrosinase inhibitors, the inhibitory effect and kinetics of phlorizin, young apple polyphenols and kojic acid on tyrosinase activity were analyzed and compared by spectrophotometry, in which kojic acid was used as a positive control. Results: phlorizin, young apple polyphenols and kojic acid could effectively inhibit tyrosinase activity. The order of their inhibitory effects was kojic acid>young apple polyphenols>phloridin, and their IC50 for monophenolase activity was 55.80, 54.30 and 23.81 μg/m L, respectively, and their IC50 for diphenolase activity was 75.30, 56.15 and 23.45 μg/m L, respectively. The phlorizin showed mixed inhibition at a concentration lower than 200 μg/m L and competitive inhibition at a concentration of 200 μg/m L, the young apple polyphenols showed non-competitive inhibition and the kojic acid showed mixed inhibition. In summary, the inhibitory effect and inhibitory mechanism of the inhibitor is not only related to its composition, but also related to its concentration. All three inhibitors can reduce the synthesis of melanin by inhibiting the hydroxylation of tyrosine to dopa and the oxidation of dopa to dopaquinone and dopachrome. Compared with phlorizin, young apple polyphenols is more suitable as tyrosinase inhibitors and has great potential for application in whitening products because of its better inhibitory effect, cheaper price and richer content.
引文
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[14] Mei-Zhen L, Wei-Ming C, Chong O Y, et al. Antityrosinase mechanism of omeprazole and its application on the preservation of fresh-cut Fuji apple[J]. International Journal of Biological Macromolecules, 2018, 117:538-545
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[19] Lin Y F, Hu Y H, Lin H T, et al. Inhibitory effects of propyl gallate on tyrosinase and its application in controlling pericarp browning of harvested longan fruits[J]. Journal of Agricultural&Food Chemistry, 2013, 61(11):2889-2895
[20] Li B, He X L, Zhao Y P, et al. Tyrosinase-related protein 1,(TYRP1)gene polymorphism and skin differential expression related to coat color in mongolian horse[J]. Livestock Science, 2014, 167(1):58-64
[21] Hseu Y C, Cheng K C, Lin Y C, et al. Synergistic effects of linderanolide B combined with arbutin, PTU or kojic acid on tyrosinase inhibition[J]. Current Pharmaceutical Biotechnology, 2015, 16(12):1-7
[22] Yan W, Mi-Mi H, Ying S, et al. Synergistic promotion on tyrosinase inhibition by antioxidants[J]. Molecules, 2018,23(1):106-118
[23] Guo N, Wang C, Shang C, et al. Integrated study of the mechanism of tyrosinase inhibition by baicalein using kinetic,multispectroscopic and computational simulation analyses[J].International Journal of Biological Macromolecules, 2018,118:57-68
[24] Yue L M, Lee J, Zhi-Rong Lü, et al. Effect of Cd2+on tyrosinase:Integration of inhibition kinetics with computational simulation[J]. International Journal of Biological Macromolecules, 2016, 94:836-844
[25] Hu Y H, Zhuang J X, Yu F, et al. Inhibitory effects of cefotaxime on the activity of mushroom tyrosinase[J].Journal of Bioscience&Bioengineering, 2016, 121(4):385-389
[26] Si H, Wang X, Li L, et al. Inhibitory effects of4-chlorocinnamaldehyde on the activity of mushroom tyrosinase[J]. Medicinal Chemistry Research, 2017, 26(7):1377-1381
[27] Chai W M, Lin M Z, Feng H L, et al. Proanthocyanidins purified from fruit pericarp of Clausena lansium(Lour.)Skeels as efficient tyrosinase inhibitors:structure evaluation,inhibitory activity and molecular mechanism[J]. Food&Function, 2017, 8(3):1043
[28] Freitas M M D, Fontes P R, Souza P M, et al. Extracts of Morus nigra L. leaves standardized in chlorogenic acid, rutin and isoquercitrin:tyrosinase inhibition and cytotoxicity[J].Plos One, 2016, 11(9):e0163130
[29] Li H R, Habasi M, Xie L Z, et al. Effect of chlorogenic acid on melanogenesis of B16 melanoma cells[J]. Molecules, 2014,19(9):12940-12948
[30] Hwang J M, Kuo H C, Lin C T, et al. Inhibitory effect of liposome-encapsulated anthocyanin on melanogenesis in human melanocytes[J]. Pharmaceutical Biology, 2013, 51(8):941-947
[31]王庆华,邓志刚,刘山,等.荔枝壳提取物对酪氨酸酶的抑制作用[J].日用化学工业, 2010,40(1):31-34WANG Qing-hua, DENG Zhi-gang, LIU Shan, et al.Inhibitory mechanism of extracts from litchi shell on mushroom tyrosinase[J]. China Surfactant Detergent&Cosmetics, 2010, 40(1):31-34
[32]罗耀红.漆酶对苹果多酚的酶促氧化及其产物分析[D].咸阳:西北农林科技大学,2008LUO Yao-hong. Study on laccase catelyzed oxidatio of phenolic compounds from apple and the characterization of its end products[D]. Xianyang:Northwest A&F University,2008
[33]黄璜,宋康康,陈清西.曲酸作为化妆品添加剂的增白作用机理研究[J].厦门大学学报(自然科学版),2003,42(5):652-656HUANG Huang, SONG Kang-kang, CHEN Qing-xi. Studies on whitening effect of kojic acid as cosmetic additive[J].Journal of Xiamen University(Natural Edition), 2003, 42(5):652-656
[34] Meng W, Zhang C, Xiao D. The effect of different activated carbon and bleaching temperature on kojic acid bleaching[J].Lecture Notes in Electrical Engineering, 2015, 333:325-333
[2] Tian J, Wu X, Zhang M, et al. Comparative study on the effects of apple peel polyphenols and apple flesh polyphenols on cardiovascular risk factors in mice[J]. Clinical&Experimental Hypertension, 2017, 40(10):1-8
[3] Zeng B, Su M, Chen Q, et al. Antioxidant and hepatoprotective activities of polysaccharides from Anoectochilus roxburghii[J]. Carbohydrate Polymers, 2016,153:391-398
[4]霍彦雄,任亚梅,袁春龙,等.根皮苷豆蔻酸酯的抗氧化活性[J].食品科学,2017,38(9):119-125HUO Yan-xiong, REN Ya-mei, YUAN Chun-long, et al.Antioxidant activities of Phloridzin myristate[J]. Food Science, 2017, 38(9):119-125
[5] Xiao Z, Zhang Y, Chen X, et al. Extraction, identification,and antioxidant and anticancer tests of seven dihydrochalcones from malus'red splendor'fruit[J]. Food Chemistry, 2017, 231:324-331
[6] Sun L, Guo Y, Fu C, et al. Simultaneous separation and purification of total polyphenols, chlorogenic acid and phlorizin from thinned young apples[J]. Food Chemistry,2013, 136(2):1022-1029
[7]谭飓,周志钦.根皮苷研究进展[J].食品与发酵工业,2013,39(8):182-186TAN Ju, ZHOU Zhi-qin. Research progress of phlorizin[J].Food and fermentation Industries, 2013, 39(8):182-186
[8]潘越,冯志勇,陈辉,等.食用菌黑色素代谢的研究进展[J].生物学杂志,2014,31(1):68-70,74PAN Yue, FENG Zhi-yong, CHEN Hui, et al. Advances in research on the melanin metabolism of edible fungi[J].Journal of Biology, 2014, 31(1):68-70, 74
[9] Jimenezcervantes C, Garciaborron J C, Valverde P, et al.Tyrosinase isoenzymes in mammalian melanocytes:Biochemical characterization of two melanosomal tyrosinases from B16 mouse melanoma[J]. Febs Journal,2010, 217(2):549-556
[10] Tief K, Hahne M, Schmidt A, et al. Tyrosinase, the key enzyme in melanin synthesis, is expressed in murine brain[J].Febs Journal, 2010, 241(1):12-16
[11] Niu C, Aisa H A. Upregulation of melanogenesis and tyrosinase activity:Potential agents for vitiligo[J]. Molecules,2017, 22(8):1303-1030
[12]陈清西.酶学及其研究技术[M].厦门:厦门大学出版社,2010,99-145CHEN Qing-xi. Enzymology and Its Research Techniques[M]. Xiamen:Xiamen University Press. 2010, 99-145
[13]李瑜,杨国浩,詹丽娟,等.双孢菇中多酚氧化酶活性的影响因素[J].食品科学,2011,32(18):319-322LI Yu, YANG Guo-hao, ZHAN LI-juan, et al. Affecting factors of polyphenol oxidase activity in Agaricus bisporus[J]. Food Science, 2011, 32(18):319-322
[14] Mei-Zhen L, Wei-Ming C, Chong O Y, et al. Antityrosinase mechanism of omeprazole and its application on the preservation of fresh-cut Fuji apple[J]. International Journal of Biological Macromolecules, 2018, 117:538-545
[15]胡泳华,贾玉龙,陈清西.酪氨酸酶抑制剂的应用研究进展[J].厦门大学学报(自然版),2016,55(5):760-768HU Yong-hua, JIA Yu-long, CHEN Qing-xi. Research progress in the application of tyrosinase Inhibitor[J]. Journal of Xiamen University(Natural Edition), 2016, 55(5):760-768
[16] Cui Y, Liang G, Hu Y H, et al. Alpha-substituted derivatives of cinnamaldehyde as tyrosinase inhibitors:Inhibitory mechanism and molecular analysis[J]. Journal of Agricultural&Food Chemistry, 2015, 63(2):716-722
[17] Mohamad R, Mohamed M S, Suhaili N, et al. Kojic acid:Applications and development of fermentation process for production[J]. Biotechnology&Molecular Biology Reviews, 2010, 2:24-37
[18] Ortiz-Ruiz C V, Berna J, Garcia-Molina M D M, et al.Identification of p-hydroxybenzyl alcohol, tyrosol, phloretin and its derivate phloridzin as tyrosinase substrates[J].Bioorganic&Medicinal Chemistry, 2015, 23(13):3738-3746
[19] Lin Y F, Hu Y H, Lin H T, et al. Inhibitory effects of propyl gallate on tyrosinase and its application in controlling pericarp browning of harvested longan fruits[J]. Journal of Agricultural&Food Chemistry, 2013, 61(11):2889-2895
[20] Li B, He X L, Zhao Y P, et al. Tyrosinase-related protein 1,(TYRP1)gene polymorphism and skin differential expression related to coat color in mongolian horse[J]. Livestock Science, 2014, 167(1):58-64
[21] Hseu Y C, Cheng K C, Lin Y C, et al. Synergistic effects of linderanolide B combined with arbutin, PTU or kojic acid on tyrosinase inhibition[J]. Current Pharmaceutical Biotechnology, 2015, 16(12):1-7
[22] Yan W, Mi-Mi H, Ying S, et al. Synergistic promotion on tyrosinase inhibition by antioxidants[J]. Molecules, 2018,23(1):106-118
[23] Guo N, Wang C, Shang C, et al. Integrated study of the mechanism of tyrosinase inhibition by baicalein using kinetic,multispectroscopic and computational simulation analyses[J].International Journal of Biological Macromolecules, 2018,118:57-68
[24] Yue L M, Lee J, Zhi-Rong Lü, et al. Effect of Cd2+on tyrosinase:Integration of inhibition kinetics with computational simulation[J]. International Journal of Biological Macromolecules, 2016, 94:836-844
[25] Hu Y H, Zhuang J X, Yu F, et al. Inhibitory effects of cefotaxime on the activity of mushroom tyrosinase[J].Journal of Bioscience&Bioengineering, 2016, 121(4):385-389
[26] Si H, Wang X, Li L, et al. Inhibitory effects of4-chlorocinnamaldehyde on the activity of mushroom tyrosinase[J]. Medicinal Chemistry Research, 2017, 26(7):1377-1381
[27] Chai W M, Lin M Z, Feng H L, et al. Proanthocyanidins purified from fruit pericarp of Clausena lansium(Lour.)Skeels as efficient tyrosinase inhibitors:structure evaluation,inhibitory activity and molecular mechanism[J]. Food&Function, 2017, 8(3):1043
[28] Freitas M M D, Fontes P R, Souza P M, et al. Extracts of Morus nigra L. leaves standardized in chlorogenic acid, rutin and isoquercitrin:tyrosinase inhibition and cytotoxicity[J].Plos One, 2016, 11(9):e0163130
[29] Li H R, Habasi M, Xie L Z, et al. Effect of chlorogenic acid on melanogenesis of B16 melanoma cells[J]. Molecules, 2014,19(9):12940-12948
[30] Hwang J M, Kuo H C, Lin C T, et al. Inhibitory effect of liposome-encapsulated anthocyanin on melanogenesis in human melanocytes[J]. Pharmaceutical Biology, 2013, 51(8):941-947
[31]王庆华,邓志刚,刘山,等.荔枝壳提取物对酪氨酸酶的抑制作用[J].日用化学工业, 2010,40(1):31-34WANG Qing-hua, DENG Zhi-gang, LIU Shan, et al.Inhibitory mechanism of extracts from litchi shell on mushroom tyrosinase[J]. China Surfactant Detergent&Cosmetics, 2010, 40(1):31-34
[32]罗耀红.漆酶对苹果多酚的酶促氧化及其产物分析[D].咸阳:西北农林科技大学,2008LUO Yao-hong. Study on laccase catelyzed oxidatio of phenolic compounds from apple and the characterization of its end products[D]. Xianyang:Northwest A&F University,2008
[33]黄璜,宋康康,陈清西.曲酸作为化妆品添加剂的增白作用机理研究[J].厦门大学学报(自然科学版),2003,42(5):652-656HUANG Huang, SONG Kang-kang, CHEN Qing-xi. Studies on whitening effect of kojic acid as cosmetic additive[J].Journal of Xiamen University(Natural Edition), 2003, 42(5):652-656
[34] Meng W, Zhang C, Xiao D. The effect of different activated carbon and bleaching temperature on kojic acid bleaching[J].Lecture Notes in Electrical Engineering, 2015, 333:325-333
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