EGCG分子修饰在化妆品中的应用
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摘要
总结了化妆品功效添加剂表没食子儿茶素没食子酸酯[(-)-epigallocatechin-3-gallate,EGCG]在化妆品实际应用中存在的稳定性差、配伍性差、色泽变化、透皮吸收利用度不高等问题,对EGCG的基团修饰和包埋修饰在化妆品中的潜在应用进行了综述,为EGCG在化妆品中更好的应用提供理论资料。
The problems of cosmetic additive(-)-epigallocatechin-3-gallate[EGCG]such as poor stability and compatibility,color change,trans cutaneous absorption and low utilization were summarized.The potential applications of modification of chemical groups and encapsulation of EGCG in cosmetics were reviewed.This work provides information for better use of EGCG in cosmetics.
The problems of cosmetic additive(-)-epigallocatechin-3-gallate[EGCG]such as poor stability and compatibility,color change,trans cutaneous absorption and low utilization were summarized.The potential applications of modification of chemical groups and encapsulation of EGCG in cosmetics were reviewed.This work provides information for better use of EGCG in cosmetics.
引文
[1]YANG H,LANDIS-PIWOWAR K,CHAN T H,et al.Green Tea Polyphenols as ProteasomeInhibitors:Implication in Chemoprevention[J].Curr Cancer Drug Targets,2011,11(3):296-306.
[2]FENG B,FANG Y,WEI S M.Effect and Mechanism of Epigallocatechin-3-gallate(EGCG).Against the Hydrogen Peroxide-induced Oxidative Damage in Human Dermal Fibroblasts[J].J Cosmetic Sci,2013,64(1):35-44.
[3]KIM D S,PARK S H,KWON S B,et al.(-)-Epigallocatechin-3-gallate and Hinokitiol Reduce Melanin Synthesis via Decreased MITF Production[J].Arch Pharm Res,2004,27:334-339.
[4]FUJIMURA Y,UMEDA D,YAMADA K,et al.The Impact of the 67kDa LamininReceptor on both Cell-surface Binding and Anti-allergic Action of Tea Catechins[J].Arch Biochem Biophys,2008,476(2):133-138.
[5]YOON J Y,KWON H H,MIN S U.Epigallocatechin-3-gallate Improves Acne in Humans by Modulating Intracellular Molecular Targets and Inhibiting P.Acnes[J].J Invest Dermatol,2013,133(2):429-440.
[6]HASLAM E,LILLEY T H,CAI Y,et al.Traditional Herbal Medicines-the Role of Polyphenols[J].Planta Medica,1989,55(1):1-8.
[7]GIANETI M D,MERCURIO D G,CAMPOS PMBGM.The Use of Green Tea Extract in Cosmetic Formulations:not only an Antioxidant Active Ingredient[J].Dermatol Therapy,2013,26(3):267-271.
[8]于莎莎,丁阳平,罗赛,等.儿茶素衍生物合成及药理作用研究进展[J].食品科学,2012,33(17):318-326.
[9]ZHONG Y,SHAHIDI F.Lipophilized Epigallocatechin Gallate(EGCG)Derivatives as Novel Antioxidants[J].J Agric Food Chem,2011,59(12):6526-6533.
[10]ZHU S,LI Y,LI Z,et al.Lipase-catalyzed Synthesis of Acetylated EGCG and Antioxidant Properties of the Acetylated Derivatives[J].Food Res Int,2014,56:279-286.
[11]ZHONG Y,CHIOU Y S,PAN M H,et al.Anti-inflammatory Activity of Lipophilic Epigallocatechin Gallate(EGCG)Derivatives in LPS-stimulated Murine Macrophages[J].Food Chem,2012,134(2):742-748.
[12]李卫,宁正祥.黄酮类化合物的分子修饰[J].食品科学,2005,26(8):505-507.
[13]LAM W H,KAZI A,KUHN D J,et al.A Potential Prodrug for a Green Tea Polyphenol Proteasome Inhibitor:Evaluation of the Peracetate Ester of(-)-Gpigallocatechin Gallate[(-)-EGCG][J].Bioorga&Med Chem,2004,12(21):5587-5593.
[14]CHEN P,DICKINSON D,HSU S.Lipid-soluble Green Tea Polyphenols:Stabilized for Effective Formulation[J].Handbook of Green Tea and Health Res,2009,(4):45-61.
[15]BERGERON L,GONDRANC,OBERTO G,et al.Skin Presenting a Higher Level of Caspase-14is Better Protected from UVB Irradiation According to in Vitro and in Vivo Studies[J].J Cosmetic Dermatol,2012,11(2):111-121.
[16]龙丹,江和源,张建勇,等.儿茶素分子修饰方法及应用进展[J].茶叶科学,2013,33(1):1-12.
[17]KAGAYA N,HARA Y,SAIJO R,et al.Novel Function of Rare Catechin,Epigallocatechin-3-(3″-OMethyl)Gallate,Against Cold Injury in Primary Rat Hepatocytes[J].J Biosci Bioeng,2003,96(6):559-563.
[18]SUZUKI M,YOSHINO K,MAEDA-YAMAMOTO M,et al.Inhibitory Effects of Tea Catechins and Omethylated Derivatives of(-)-Epigallocatechin-3-Ogallate on Mouse TypeⅣAllergy[J].J Agric Food Chem,2000,48(11):5649-5653.
[19]FUJIMURA Y,TACHIBANA H,MAEDAYAMAMOTO M,et al.Antiallergic Tea Catechin,(-)-Epigallocatechin-3-O-(3-O-methyl)-gallate,Suppresses FcεRI Expression in Human Basophilic KU812Cells[J].JAgric Food Chem,2002,50(20):5729-5734.
[20]MAEDA-YAMAMOTO M,INAGAKI N,KITAURA J,et al.O-Methylated Catechins from Tea Leaves Inhibit Multiple Protein Kinases in Mast Cells[J].J Immunol,2004,172(7):4486-4492.
[21]FUJIMURA Y,UMEDA D,YANO S,et al.The67kDa Laminin Receptor as a Primary Determinant of Anti-allergic Effects of O-Methylated EGCG[J].Biochem Bioph Res Co,2007,364(1):79-85.
[22]MAEDA-YAMAMOTO M.Human Clinical Studies of Tea Polyphenols in Allergy or Life Style-related Diseases[J].Curr Pharm Design,2013,19(34):6148-6155.
[23]YAMAMOTO M,NAGAI H.Anti-allergic Agent and Beverage/Food,Preparation for External Application or Cosmetic Comprising the Agent:JP,4 997 523B2[P],2012.
[24]YAMAMOTO M,KIRITA M,HONMA D,et al.Novel Methylated Catechin and Composion Containing the Same:Eur,20 080 703 535[P],2009.
[25]KIRITA M,HONMA D,TANAKA Y,et al.Cloning of a Novel O-Methyltransferase from Camellia Sinensis and Synthesis of O-Methylated EGCG and Evaluation of Their Bioactivity[J].J Agric Food Chem,2010,58(12):7196-7201.
[26]ANON.Inoveol EGCG(epigallocatechin gallateα-Dglucoside):Cosmetic and Pharmacological Activities[J/OL].IP.com Journal,2009,9(5A):35.
[27]KITAO S,SHIMAOKA Y,SEKINE H,et al.Preparation of Epigallocatechin Gallate Glycosides as TyrosinaseInhibitors:JP,07 010 897[P],1995.
[28]NADIM M,AURIOL D,LAMERANT-FAYEL N,et al.Improvement of Polyphenol Properties Upon Glucosylation in a UV-induced Skin Cell Ageing Model[J].Int J Cosmetic Sci,2014,36(6):579-587.
[29]陈荣义.茶多酚的提取纯化及其改性的研究[D].成都:四川大学,2005.
[30]OHARA M,OHYAMA Y.Delivery and Application of Dietary Polyphenols to Target Organs,Tissues and Intracellular Organelles[J].Curr Drug Metab,2014,15(1):37-47.
[31]FANG J Y,HWANG T L,HUANG Y L,et al.Enhancement of the Transdermal Delivery of Catechins by Liposomes Incorporating Anionic Surfactants and Ethanol[J].Int J Pharm,2006,310(1-2):131-138.
[32]FANG Z X,BHANDARI B.Encapsulation of Polyphenols[J].Trends Food Sci Tech,2010,21(10):510-523.
[33]TOUITOU E,DAYAN N,BERGELSON L,et al.Ethosomes-novel Vesicular Carriers for Enhanced Delivery:Characterization and Skin Penetration Properties[J].J Control Release,2000,65(3):403-418.
[34]PAOLINO D,LUCANIA G,MARDENTE D,et al.Ethosomes for Skin Delivery of Ammonium Glycyrrhizinate:in vitro Percuteneous Permeation through Human Skin and In vivo Anti-inflammatory Activity on Human Volunteers[J].J Control Release,2005,106(1-2):99-110.
[35]VERMA P,PATHAK K.Therapeutic and Cosmeceutical Potential of Ethosomes:an Overview[J].J Adv Pharm Tech Res,2010,1(3):274-282.
[36]陈元岭,王丹,王技,等.茶多酚醇质体的制备和体外透皮吸收研究[J].中国新药杂志,2013,22(15):1757-1760,1778.
[37]WISUITIPROT W,SOMSIRI A,INGKANINAN K,et al.In Vitro Human Skin Permeation and Cutaneous Metabolism of Catechins from Green Tea Extract and Green Tea Extract-loaded Chitosan Microparticles[J].Int J Cosmetic Sci,2011,33(6):572-579.
[38]WISUITIPROT W,SOMSIRI A,INGKANINAN K,et al.A Novel Technique for Chitosan Microparticle Preparation Using a Water/Silicone Emulsion:Green Tea Model[J].Int J Cosmetic Sci,2011,33(4):351-358.
[39]KUMAR S A,SURESH M,KUMAR S N K,et al.Synthesis and Characterization of Major Green Tea Catechin Nanoparticle[J].Asian J Chem,2013,25(Suppl.Issue):343-346.
[40]SIDDIQUI I A,NIHAL M,ADHAMI VM,et al.Excellent Anti-proliferative and Pro-apoptotic Effects of(-)-Epigallocatechin-3-gallate Encapsulated in Chitosan Nanoparticles on Human Melanoma Cell Growth both in Vitro and in Vivo[J].Nanomed,2014,10(8):1619-1626.
[41]HU B,TING Y W,ZENG X X,et al.Cellular Uptake and Cytotoxicity of Chitosan-caseinophosphopeptides Nanocomplexes Loaded with Epigallocatechin Gallate[J].Carbohyd Polym,2012,89(2):362-370.
[42]HU B,TING Y W,ZENG X X,et al.Bioactive Peptides/Chitosan Nanoparticles Enhance Cellular Antioxidant Activity of(-)-Epigallocatechin-3-gallate[J].J Agric Food Chem,2013,61(4):875-881.
[43]SHIN G H,HUANG Q R.Encapsulation and Controlled Release of Polyphenols Using Protein/Polysaccharide Coacervates[C].Abstracts of Papers of the Am Chem Soc,Washington D C,2005:48.
[44]SHPIGELMAN A,ISRAELI G,LIVNEY Y D.Thermally-induced Proteine-polyphenol Co-assemblies:Beta Lactoglobulin-based Nanocomplexes as Protective Nanovehicles for EGCG[J].Food Hydrocolloids,2010,24:735-743.
[2]FENG B,FANG Y,WEI S M.Effect and Mechanism of Epigallocatechin-3-gallate(EGCG).Against the Hydrogen Peroxide-induced Oxidative Damage in Human Dermal Fibroblasts[J].J Cosmetic Sci,2013,64(1):35-44.
[3]KIM D S,PARK S H,KWON S B,et al.(-)-Epigallocatechin-3-gallate and Hinokitiol Reduce Melanin Synthesis via Decreased MITF Production[J].Arch Pharm Res,2004,27:334-339.
[4]FUJIMURA Y,UMEDA D,YAMADA K,et al.The Impact of the 67kDa LamininReceptor on both Cell-surface Binding and Anti-allergic Action of Tea Catechins[J].Arch Biochem Biophys,2008,476(2):133-138.
[5]YOON J Y,KWON H H,MIN S U.Epigallocatechin-3-gallate Improves Acne in Humans by Modulating Intracellular Molecular Targets and Inhibiting P.Acnes[J].J Invest Dermatol,2013,133(2):429-440.
[6]HASLAM E,LILLEY T H,CAI Y,et al.Traditional Herbal Medicines-the Role of Polyphenols[J].Planta Medica,1989,55(1):1-8.
[7]GIANETI M D,MERCURIO D G,CAMPOS PMBGM.The Use of Green Tea Extract in Cosmetic Formulations:not only an Antioxidant Active Ingredient[J].Dermatol Therapy,2013,26(3):267-271.
[8]于莎莎,丁阳平,罗赛,等.儿茶素衍生物合成及药理作用研究进展[J].食品科学,2012,33(17):318-326.
[9]ZHONG Y,SHAHIDI F.Lipophilized Epigallocatechin Gallate(EGCG)Derivatives as Novel Antioxidants[J].J Agric Food Chem,2011,59(12):6526-6533.
[10]ZHU S,LI Y,LI Z,et al.Lipase-catalyzed Synthesis of Acetylated EGCG and Antioxidant Properties of the Acetylated Derivatives[J].Food Res Int,2014,56:279-286.
[11]ZHONG Y,CHIOU Y S,PAN M H,et al.Anti-inflammatory Activity of Lipophilic Epigallocatechin Gallate(EGCG)Derivatives in LPS-stimulated Murine Macrophages[J].Food Chem,2012,134(2):742-748.
[12]李卫,宁正祥.黄酮类化合物的分子修饰[J].食品科学,2005,26(8):505-507.
[13]LAM W H,KAZI A,KUHN D J,et al.A Potential Prodrug for a Green Tea Polyphenol Proteasome Inhibitor:Evaluation of the Peracetate Ester of(-)-Gpigallocatechin Gallate[(-)-EGCG][J].Bioorga&Med Chem,2004,12(21):5587-5593.
[14]CHEN P,DICKINSON D,HSU S.Lipid-soluble Green Tea Polyphenols:Stabilized for Effective Formulation[J].Handbook of Green Tea and Health Res,2009,(4):45-61.
[15]BERGERON L,GONDRANC,OBERTO G,et al.Skin Presenting a Higher Level of Caspase-14is Better Protected from UVB Irradiation According to in Vitro and in Vivo Studies[J].J Cosmetic Dermatol,2012,11(2):111-121.
[16]龙丹,江和源,张建勇,等.儿茶素分子修饰方法及应用进展[J].茶叶科学,2013,33(1):1-12.
[17]KAGAYA N,HARA Y,SAIJO R,et al.Novel Function of Rare Catechin,Epigallocatechin-3-(3″-OMethyl)Gallate,Against Cold Injury in Primary Rat Hepatocytes[J].J Biosci Bioeng,2003,96(6):559-563.
[18]SUZUKI M,YOSHINO K,MAEDA-YAMAMOTO M,et al.Inhibitory Effects of Tea Catechins and Omethylated Derivatives of(-)-Epigallocatechin-3-Ogallate on Mouse TypeⅣAllergy[J].J Agric Food Chem,2000,48(11):5649-5653.
[19]FUJIMURA Y,TACHIBANA H,MAEDAYAMAMOTO M,et al.Antiallergic Tea Catechin,(-)-Epigallocatechin-3-O-(3-O-methyl)-gallate,Suppresses FcεRI Expression in Human Basophilic KU812Cells[J].JAgric Food Chem,2002,50(20):5729-5734.
[20]MAEDA-YAMAMOTO M,INAGAKI N,KITAURA J,et al.O-Methylated Catechins from Tea Leaves Inhibit Multiple Protein Kinases in Mast Cells[J].J Immunol,2004,172(7):4486-4492.
[21]FUJIMURA Y,UMEDA D,YANO S,et al.The67kDa Laminin Receptor as a Primary Determinant of Anti-allergic Effects of O-Methylated EGCG[J].Biochem Bioph Res Co,2007,364(1):79-85.
[22]MAEDA-YAMAMOTO M.Human Clinical Studies of Tea Polyphenols in Allergy or Life Style-related Diseases[J].Curr Pharm Design,2013,19(34):6148-6155.
[23]YAMAMOTO M,NAGAI H.Anti-allergic Agent and Beverage/Food,Preparation for External Application or Cosmetic Comprising the Agent:JP,4 997 523B2[P],2012.
[24]YAMAMOTO M,KIRITA M,HONMA D,et al.Novel Methylated Catechin and Composion Containing the Same:Eur,20 080 703 535[P],2009.
[25]KIRITA M,HONMA D,TANAKA Y,et al.Cloning of a Novel O-Methyltransferase from Camellia Sinensis and Synthesis of O-Methylated EGCG and Evaluation of Their Bioactivity[J].J Agric Food Chem,2010,58(12):7196-7201.
[26]ANON.Inoveol EGCG(epigallocatechin gallateα-Dglucoside):Cosmetic and Pharmacological Activities[J/OL].IP.com Journal,2009,9(5A):35.
[27]KITAO S,SHIMAOKA Y,SEKINE H,et al.Preparation of Epigallocatechin Gallate Glycosides as TyrosinaseInhibitors:JP,07 010 897[P],1995.
[28]NADIM M,AURIOL D,LAMERANT-FAYEL N,et al.Improvement of Polyphenol Properties Upon Glucosylation in a UV-induced Skin Cell Ageing Model[J].Int J Cosmetic Sci,2014,36(6):579-587.
[29]陈荣义.茶多酚的提取纯化及其改性的研究[D].成都:四川大学,2005.
[30]OHARA M,OHYAMA Y.Delivery and Application of Dietary Polyphenols to Target Organs,Tissues and Intracellular Organelles[J].Curr Drug Metab,2014,15(1):37-47.
[31]FANG J Y,HWANG T L,HUANG Y L,et al.Enhancement of the Transdermal Delivery of Catechins by Liposomes Incorporating Anionic Surfactants and Ethanol[J].Int J Pharm,2006,310(1-2):131-138.
[32]FANG Z X,BHANDARI B.Encapsulation of Polyphenols[J].Trends Food Sci Tech,2010,21(10):510-523.
[33]TOUITOU E,DAYAN N,BERGELSON L,et al.Ethosomes-novel Vesicular Carriers for Enhanced Delivery:Characterization and Skin Penetration Properties[J].J Control Release,2000,65(3):403-418.
[34]PAOLINO D,LUCANIA G,MARDENTE D,et al.Ethosomes for Skin Delivery of Ammonium Glycyrrhizinate:in vitro Percuteneous Permeation through Human Skin and In vivo Anti-inflammatory Activity on Human Volunteers[J].J Control Release,2005,106(1-2):99-110.
[35]VERMA P,PATHAK K.Therapeutic and Cosmeceutical Potential of Ethosomes:an Overview[J].J Adv Pharm Tech Res,2010,1(3):274-282.
[36]陈元岭,王丹,王技,等.茶多酚醇质体的制备和体外透皮吸收研究[J].中国新药杂志,2013,22(15):1757-1760,1778.
[37]WISUITIPROT W,SOMSIRI A,INGKANINAN K,et al.In Vitro Human Skin Permeation and Cutaneous Metabolism of Catechins from Green Tea Extract and Green Tea Extract-loaded Chitosan Microparticles[J].Int J Cosmetic Sci,2011,33(6):572-579.
[38]WISUITIPROT W,SOMSIRI A,INGKANINAN K,et al.A Novel Technique for Chitosan Microparticle Preparation Using a Water/Silicone Emulsion:Green Tea Model[J].Int J Cosmetic Sci,2011,33(4):351-358.
[39]KUMAR S A,SURESH M,KUMAR S N K,et al.Synthesis and Characterization of Major Green Tea Catechin Nanoparticle[J].Asian J Chem,2013,25(Suppl.Issue):343-346.
[40]SIDDIQUI I A,NIHAL M,ADHAMI VM,et al.Excellent Anti-proliferative and Pro-apoptotic Effects of(-)-Epigallocatechin-3-gallate Encapsulated in Chitosan Nanoparticles on Human Melanoma Cell Growth both in Vitro and in Vivo[J].Nanomed,2014,10(8):1619-1626.
[41]HU B,TING Y W,ZENG X X,et al.Cellular Uptake and Cytotoxicity of Chitosan-caseinophosphopeptides Nanocomplexes Loaded with Epigallocatechin Gallate[J].Carbohyd Polym,2012,89(2):362-370.
[42]HU B,TING Y W,ZENG X X,et al.Bioactive Peptides/Chitosan Nanoparticles Enhance Cellular Antioxidant Activity of(-)-Epigallocatechin-3-gallate[J].J Agric Food Chem,2013,61(4):875-881.
[43]SHIN G H,HUANG Q R.Encapsulation and Controlled Release of Polyphenols Using Protein/Polysaccharide Coacervates[C].Abstracts of Papers of the Am Chem Soc,Washington D C,2005:48.
[44]SHPIGELMAN A,ISRAELI G,LIVNEY Y D.Thermally-induced Proteine-polyphenol Co-assemblies:Beta Lactoglobulin-based Nanocomplexes as Protective Nanovehicles for EGCG[J].Food Hydrocolloids,2010,24:735-743.