茶叶中天然累积和人工合成的甲基化EGCG的研究进展
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摘要
基于国内外甲基化表没食子儿茶素没食子酸酯[O-methylated (-)-epigallocatechin-3-O-gallate,O-methylated EGCG]的研究现状,阐述种质资源、采摘时间、叶片成熟度标准、加工工艺对茶叶中甲基化EGCG含量的影响,并探讨当前人工合成甲基化EGCG的研究进展。
Based on the research status of methylation gallic acid ester gallic catechins(EGCG)both at home and abroad,this paper expounded the influence of germplasm resources,harvesting time,leaf maturity and processing technology on O-methylated EGCG content in tea. Meanwhile,the progress of synthetic of O-methylated EGCG was discussed.
Based on the research status of methylation gallic acid ester gallic catechins(EGCG)both at home and abroad,this paper expounded the influence of germplasm resources,harvesting time,leaf maturity and processing technology on O-methylated EGCG content in tea. Meanwhile,the progress of synthetic of O-methylated EGCG was discussed.
引文
[1]严鸿德.茶叶深加工技术[M].北京:中国轻工业出版社,1998:1-6
[2]Ryoya Su Sauo.Isolation and Chemical Structures of Two New Catechins from Fresh tea leaf[J].Agricultural and Biological Chemistry,1982(7):1969-1970
[3]Mitsuaki Sano,Masazumi Suzuki,Toshio Miyase,et al.Novel antiallergic catechin derivatives isolated from oolong tea[J].Journal of Agriculture and Food Chemistry,1999,47(5):1906-1910
[4]Maeda-Yamamoto M,Sano M.The change of epigallocatechin-3-O-(3-O-Methyl)gallate content in tea ofdifferent varieties,tea seasons of crop and processing Method[J].The Japanese Society for Food Science and Technology,2001,48:64-68
[5]Suzuki M,Sano M,Yoshida R.Epimerization of Tea Catechins and O-Methylated Derivatives Relationship between Epimerization and Chemical Structure[J].Journal of Agricultural and Food Chemistry,2003,5(51):510-514
[6]Maeda-Yamamoto M,Tachibana H.Anti-Allergic Action of O-methylated EGCG in Green Tea Cultivar Benifuuki[J].Journal of Food&Drug Analysis,2012,20:313-317
[7]Maeda-Yamamoto,M EmaK,ShibuichiI.In vitro and in vivo anti-allergic effects of‘benifuuki’green tea containing O-methylated catechin and ginger extract enhancement[J].Cytotechnology,2007,55(2/3):135-142
[8]Tantoush Z,Apostolovic D,Kravic B,et al.Green tea catechins of food supplements facilitate pepsin digestion of major food allergens,but hampers their digestion if oxidized by phenol oxidase[J].Journal of Functional Foods,2012,4(3):650-660
[9]Maeda-Yamamoto M.Effects of tea infusions of varieties or different manufacturing types on inhibition of mouse mast cell activation[J].Biosci Biotechnol Biochem,1998,62(11):2277-2279
[10]Suzuki M,Yoshino K,Maeda-Yamamoto M,et al.Inhibitory effects of tea catechins and O-Methylated derivatives of(-)-epigallocatechin-3-O-gallate on mouse type IV allergy[J].Journal of Agricultural and Food Chemistry,2000,48(11):5649-5653
[11]吕海鹏,谭俊峰,林智.茶树种质资源EGCG3”Me含量及其变化规律研究[J].茶叶科学,2006,26(4):310-314
[12]Sano M.Inhibitory effects of O-methylated catechin derivatives on mouse type-I allergy[C].Shizuoka:Proceedings of the 2001 International Conference on O-CHA(tea)Culture and Science,SessionⅢ,Health and Benefits,2011:159-162
[13]Maeda-Yamamoto M.Anti-allegic and anti-cancer metastatic actions of green tea[J].Nippon Shokuhin kagaku Kaishi,2002,49(10):631-638
[14]Lambert J D,Sang S,Yang C S.Biotransformation of green tea polyphenols and the biological activities of those metabolites[J].Molecular pharmaceutics,2007,4(6):819-825
[15]Akaike T,Ijiri S,Sato K,et al.Determination of peroxyl radicalscavenging activity in food by using bactericidal action of alkyl peroxyl radical[J].Journal of Agricultural and Food Chemistry,1995,43(7):1864-1870
[16]Yano S,Fujimura Y,Umeda D,et al.Relationship between the biological activities of methylated derivatives of(-)-epigallo catechin-3-O-gallate(EGCG)and their cell surface binding activities[J].Journal of agricultural and food chemistry,2007,55(17):7144-7148
[17]李银花.茶树中甲基化EGCG的分离纯化与相关基因的克隆及其表达研究[D].长沙:湖南农业大学,2013
[18]Maeda-Yamamoto M,Nagal H,Suzuki Y,et al.Manufacturing Method for Low Caffeine“Benifuuki’’,“Banihomare’’Green Tea remaining the Contents of Anti-Allergic Compounds[J].Journal of the Japanese Society for Food Science and Technology,2004,51(8):435-439
[19]汪毅.茶叶中甲基化EGCG的调查研究[D].重庆:西南大学,2006
[20]罗正飞,龚正礼,汪毅,等.茶叶中甲基化EGCG的研究[J].西南大学学报(自然科学版),2008(3):56-59
[21]Lee S C,Yan R H,Cheng HY,et al.Screen and genetic assessment of tea germplasms with elevated methylated catechin,(-)-epigallocatechin-3-O-(3-O-methyl)gallate[J].Journal of agricultural and food chemistry,2009,57(19):8906-8912
[22]唐娜.茶叶中甲基化EGCG的分析方法建立与资源化学研究[D].长沙:湖南农业大学,2010
[23]李建华,齐桂年,陈盛相,等.四川茶树品种资源中EGCG3″Me研究[J].食品工业科技,2015,36(16):108-113
[24]吕海鹏,杨停,梁名志,等.“紫娟”茶中的EGCG3"Me成分研究[J].现代食品科技,2014,30(9):286-289,296
[25]Wang Kunbo,Chen Qincao,Lin Yong,et al.Separation of Catechins and O-methylated(-)-epigallocatechin Gallate Using Polyamide Thin-layer Chromatography[J].Journal of Chromatography B,2016,1017-1018,221-225
[26]Kurita I,Maeda-Yamamoto M,Tachibana H,et al.Antihypertensive effect of Benifuuki tea containing O-methylated EGCG[J].Journal of Agricultural and Food Chemistry,2010,58:1903-1908
[27]吕海鹏,林智,谭俊峰,等.茶叶中的EGCG3″Me研究[J].食品与发酵工业,2008(10):22-25
[28]吕海鹏,费冬梅,张悦,等.EGCG甲基化衍生物酶促合成的反应条件研究[J].茶叶科学,2012,32(5):441-447
[29]叶俭慧,梁月荣.茶梗木质纤维素选择性吸附茶儿茶素类及其机理研究[C].福州:经济发展方式转变与自主创新——第十二届中国科学技术协会年会,2010
[30]Feng-Lan Chiu,Jen-Kun Lin.HPLC Analysis of Naturally Occurring Methylated Catechins,3"-and4"-Methyl-epigallocatechin Gallate in Various Fresh Tea Leaves and Commercial Teas and Their Potent Inhibitory Effects on Inducible Nitric Oxide Synthase in Macrophages[J].Journal of Agriculture and Food Chemistry,2005,53:7035-7042
[31]kyoji Yoshino,Kenjiro Ogawa,Toshio Miyase,et al.Inhibitory Effects of the C-2 Epimeric Isomers of Tea Catechins on Mouse Type IV Allergy[J].J Agric Food Chem,2004,52(15):4660-4663
[32]孙业良.茶叶中甲基EGCG的研究[D].南京:南京农业大学,2009
[33]Sano M,Miyase T,Tachibana H,et al.Anti-allergic actionof tea catechins[J].Food Style,2000,21(4):72-74
[34]陈椽.制茶学[M].2版.北京:中国农业出版社,2010:6-7
[35]吕海鹏,林智,谭俊峰,等.茶叶中EGCG3″Me的研究与开发[J].食品工业科技,2008(12):275-277
[36]J Yanase E,Matsumoto E,Shinoda Y,et al.Synthesis of Methyl Derivatives of Epigallocatechin Galiate(EGCg)and Their Stabilities[J].ITE Letters on Batteries,NewTechnologies&Medicine(with News),2005,6(1):34-37
[37]Meng XF,Sang SM,Zhu N,et al.Identification and Characterization of Methylatedand Ring-Fission Metabolites of Tea Catechins Formed in Humans,Mice,and Rats[J].Chemical Research in Toxicology,2002,15(8):1042-1050
[38]吕海鹏,孙业良,林智,等.表没食子儿茶素没食子酸醋的甲基化分子修饰[J].食品科学,2010,31(15):139-142
[39]Utenova B T,Malterud K E,Rise F.Antioxidant activity of O-protected derivativesof(-)-epigallocatechin-3-gallate:inhibition of soybean and rabbit 15-lipoxygenases[J].Archive for Organic Chemistry,2007,9:6-16
[40]伍妍俊,汪小钢,宛晓春.甲基化EGCG的合成及其在人工模拟胃肠液中的稳定性[J].安徽农业大学学报,2010,37(4):688-691
[41]Aihara Y,Yoshida A,Furuta T,et al.Regioselective synthesis of methylated·epigallocatechin gallate via nitro benzenesulfonyl(Ns)protecting group[J].Bioorganicand Medicinal Chemistry Letters,2009,19(15):4171-4174
[42]Sheng BiaoWan,Q Ping Dou,Tak Hang Chan.Regiospecific and enantioselectivesynthesis of methylated metabolites of tea catechins[J].Tetrahedron,2006,62(25):5897-5904
[43]山本万里,切田雅信,佐见学.编码甲基化儿茶素生物合成酶的基因:101061222A[P].2007-10-24
[44]Kirita M,Honma D,Tanaka Y,et al.Cloning of a novel O-methyltransferase fromCamelliasinensisand synthesis of O-methylated EGCG and evaluation of theirbioactivity[J].Journal ofAgricultural and Food Chemistry,2010,58(12):7196-7201
[45]费冬梅.甲基化EGCG的酶法合成研究[D].杭州:中国农业科学院,2011
[46]吕海鹏,费冬梅,张悦,等.EGCG-O-甲基转移酶(EOMT)催化EGCG形成的EGCG甲基化衍生物分析[J].茶叶科学,2012,32(2):100-106
[47]Okushio K,Suzuki M,Matsumoto N,et al.Methylation of tea catechins byrat liver homogenates[J].Bioscience,biotechnology,and biochemistry,1999,63(2):430-432
[48]Lu H,Meng XF,Yang CS.Enzymology of methylation of tea catechins and inhibitionof catechol-O-methyltransferase by(-)-epigallocatechin gallate[J].Drug Metabolism and Disposition,2003,31(5):572-579
[49]Zhu BT,Patel UK,Cai MX,et al.O-Methylation of tea polyphenols catalyzed byhuman placental cytosolic catechol-O-methyltransferase[J].Drug metabolism anddisposition:the biological fate of chemicals,2000,28(9):1024-1030
[50]Nagai,Maeda-Yamamoto M,Suzuki Y,et al.The development of asuitable manufacturing process for‘Benifuuki’green tea beverage with anti-allergic effects[J].J.Sci.Food Agric,2005,85:1606-1612
[2]Ryoya Su Sauo.Isolation and Chemical Structures of Two New Catechins from Fresh tea leaf[J].Agricultural and Biological Chemistry,1982(7):1969-1970
[3]Mitsuaki Sano,Masazumi Suzuki,Toshio Miyase,et al.Novel antiallergic catechin derivatives isolated from oolong tea[J].Journal of Agriculture and Food Chemistry,1999,47(5):1906-1910
[4]Maeda-Yamamoto M,Sano M.The change of epigallocatechin-3-O-(3-O-Methyl)gallate content in tea ofdifferent varieties,tea seasons of crop and processing Method[J].The Japanese Society for Food Science and Technology,2001,48:64-68
[5]Suzuki M,Sano M,Yoshida R.Epimerization of Tea Catechins and O-Methylated Derivatives Relationship between Epimerization and Chemical Structure[J].Journal of Agricultural and Food Chemistry,2003,5(51):510-514
[6]Maeda-Yamamoto M,Tachibana H.Anti-Allergic Action of O-methylated EGCG in Green Tea Cultivar Benifuuki[J].Journal of Food&Drug Analysis,2012,20:313-317
[7]Maeda-Yamamoto,M EmaK,ShibuichiI.In vitro and in vivo anti-allergic effects of‘benifuuki’green tea containing O-methylated catechin and ginger extract enhancement[J].Cytotechnology,2007,55(2/3):135-142
[8]Tantoush Z,Apostolovic D,Kravic B,et al.Green tea catechins of food supplements facilitate pepsin digestion of major food allergens,but hampers their digestion if oxidized by phenol oxidase[J].Journal of Functional Foods,2012,4(3):650-660
[9]Maeda-Yamamoto M.Effects of tea infusions of varieties or different manufacturing types on inhibition of mouse mast cell activation[J].Biosci Biotechnol Biochem,1998,62(11):2277-2279
[10]Suzuki M,Yoshino K,Maeda-Yamamoto M,et al.Inhibitory effects of tea catechins and O-Methylated derivatives of(-)-epigallocatechin-3-O-gallate on mouse type IV allergy[J].Journal of Agricultural and Food Chemistry,2000,48(11):5649-5653
[11]吕海鹏,谭俊峰,林智.茶树种质资源EGCG3”Me含量及其变化规律研究[J].茶叶科学,2006,26(4):310-314
[12]Sano M.Inhibitory effects of O-methylated catechin derivatives on mouse type-I allergy[C].Shizuoka:Proceedings of the 2001 International Conference on O-CHA(tea)Culture and Science,SessionⅢ,Health and Benefits,2011:159-162
[13]Maeda-Yamamoto M.Anti-allegic and anti-cancer metastatic actions of green tea[J].Nippon Shokuhin kagaku Kaishi,2002,49(10):631-638
[14]Lambert J D,Sang S,Yang C S.Biotransformation of green tea polyphenols and the biological activities of those metabolites[J].Molecular pharmaceutics,2007,4(6):819-825
[15]Akaike T,Ijiri S,Sato K,et al.Determination of peroxyl radicalscavenging activity in food by using bactericidal action of alkyl peroxyl radical[J].Journal of Agricultural and Food Chemistry,1995,43(7):1864-1870
[16]Yano S,Fujimura Y,Umeda D,et al.Relationship between the biological activities of methylated derivatives of(-)-epigallo catechin-3-O-gallate(EGCG)and their cell surface binding activities[J].Journal of agricultural and food chemistry,2007,55(17):7144-7148
[17]李银花.茶树中甲基化EGCG的分离纯化与相关基因的克隆及其表达研究[D].长沙:湖南农业大学,2013
[18]Maeda-Yamamoto M,Nagal H,Suzuki Y,et al.Manufacturing Method for Low Caffeine“Benifuuki’’,“Banihomare’’Green Tea remaining the Contents of Anti-Allergic Compounds[J].Journal of the Japanese Society for Food Science and Technology,2004,51(8):435-439
[19]汪毅.茶叶中甲基化EGCG的调查研究[D].重庆:西南大学,2006
[20]罗正飞,龚正礼,汪毅,等.茶叶中甲基化EGCG的研究[J].西南大学学报(自然科学版),2008(3):56-59
[21]Lee S C,Yan R H,Cheng HY,et al.Screen and genetic assessment of tea germplasms with elevated methylated catechin,(-)-epigallocatechin-3-O-(3-O-methyl)gallate[J].Journal of agricultural and food chemistry,2009,57(19):8906-8912
[22]唐娜.茶叶中甲基化EGCG的分析方法建立与资源化学研究[D].长沙:湖南农业大学,2010
[23]李建华,齐桂年,陈盛相,等.四川茶树品种资源中EGCG3″Me研究[J].食品工业科技,2015,36(16):108-113
[24]吕海鹏,杨停,梁名志,等.“紫娟”茶中的EGCG3"Me成分研究[J].现代食品科技,2014,30(9):286-289,296
[25]Wang Kunbo,Chen Qincao,Lin Yong,et al.Separation of Catechins and O-methylated(-)-epigallocatechin Gallate Using Polyamide Thin-layer Chromatography[J].Journal of Chromatography B,2016,1017-1018,221-225
[26]Kurita I,Maeda-Yamamoto M,Tachibana H,et al.Antihypertensive effect of Benifuuki tea containing O-methylated EGCG[J].Journal of Agricultural and Food Chemistry,2010,58:1903-1908
[27]吕海鹏,林智,谭俊峰,等.茶叶中的EGCG3″Me研究[J].食品与发酵工业,2008(10):22-25
[28]吕海鹏,费冬梅,张悦,等.EGCG甲基化衍生物酶促合成的反应条件研究[J].茶叶科学,2012,32(5):441-447
[29]叶俭慧,梁月荣.茶梗木质纤维素选择性吸附茶儿茶素类及其机理研究[C].福州:经济发展方式转变与自主创新——第十二届中国科学技术协会年会,2010
[30]Feng-Lan Chiu,Jen-Kun Lin.HPLC Analysis of Naturally Occurring Methylated Catechins,3"-and4"-Methyl-epigallocatechin Gallate in Various Fresh Tea Leaves and Commercial Teas and Their Potent Inhibitory Effects on Inducible Nitric Oxide Synthase in Macrophages[J].Journal of Agriculture and Food Chemistry,2005,53:7035-7042
[31]kyoji Yoshino,Kenjiro Ogawa,Toshio Miyase,et al.Inhibitory Effects of the C-2 Epimeric Isomers of Tea Catechins on Mouse Type IV Allergy[J].J Agric Food Chem,2004,52(15):4660-4663
[32]孙业良.茶叶中甲基EGCG的研究[D].南京:南京农业大学,2009
[33]Sano M,Miyase T,Tachibana H,et al.Anti-allergic actionof tea catechins[J].Food Style,2000,21(4):72-74
[34]陈椽.制茶学[M].2版.北京:中国农业出版社,2010:6-7
[35]吕海鹏,林智,谭俊峰,等.茶叶中EGCG3″Me的研究与开发[J].食品工业科技,2008(12):275-277
[36]J Yanase E,Matsumoto E,Shinoda Y,et al.Synthesis of Methyl Derivatives of Epigallocatechin Galiate(EGCg)and Their Stabilities[J].ITE Letters on Batteries,NewTechnologies&Medicine(with News),2005,6(1):34-37
[37]Meng XF,Sang SM,Zhu N,et al.Identification and Characterization of Methylatedand Ring-Fission Metabolites of Tea Catechins Formed in Humans,Mice,and Rats[J].Chemical Research in Toxicology,2002,15(8):1042-1050
[38]吕海鹏,孙业良,林智,等.表没食子儿茶素没食子酸醋的甲基化分子修饰[J].食品科学,2010,31(15):139-142
[39]Utenova B T,Malterud K E,Rise F.Antioxidant activity of O-protected derivativesof(-)-epigallocatechin-3-gallate:inhibition of soybean and rabbit 15-lipoxygenases[J].Archive for Organic Chemistry,2007,9:6-16
[40]伍妍俊,汪小钢,宛晓春.甲基化EGCG的合成及其在人工模拟胃肠液中的稳定性[J].安徽农业大学学报,2010,37(4):688-691
[41]Aihara Y,Yoshida A,Furuta T,et al.Regioselective synthesis of methylated·epigallocatechin gallate via nitro benzenesulfonyl(Ns)protecting group[J].Bioorganicand Medicinal Chemistry Letters,2009,19(15):4171-4174
[42]Sheng BiaoWan,Q Ping Dou,Tak Hang Chan.Regiospecific and enantioselectivesynthesis of methylated metabolites of tea catechins[J].Tetrahedron,2006,62(25):5897-5904
[43]山本万里,切田雅信,佐见学.编码甲基化儿茶素生物合成酶的基因:101061222A[P].2007-10-24
[44]Kirita M,Honma D,Tanaka Y,et al.Cloning of a novel O-methyltransferase fromCamelliasinensisand synthesis of O-methylated EGCG and evaluation of theirbioactivity[J].Journal ofAgricultural and Food Chemistry,2010,58(12):7196-7201
[45]费冬梅.甲基化EGCG的酶法合成研究[D].杭州:中国农业科学院,2011
[46]吕海鹏,费冬梅,张悦,等.EGCG-O-甲基转移酶(EOMT)催化EGCG形成的EGCG甲基化衍生物分析[J].茶叶科学,2012,32(2):100-106
[47]Okushio K,Suzuki M,Matsumoto N,et al.Methylation of tea catechins byrat liver homogenates[J].Bioscience,biotechnology,and biochemistry,1999,63(2):430-432
[48]Lu H,Meng XF,Yang CS.Enzymology of methylation of tea catechins and inhibitionof catechol-O-methyltransferase by(-)-epigallocatechin gallate[J].Drug Metabolism and Disposition,2003,31(5):572-579
[49]Zhu BT,Patel UK,Cai MX,et al.O-Methylation of tea polyphenols catalyzed byhuman placental cytosolic catechol-O-methyltransferase[J].Drug metabolism anddisposition:the biological fate of chemicals,2000,28(9):1024-1030
[50]Nagai,Maeda-Yamamoto M,Suzuki Y,et al.The development of asuitable manufacturing process for‘Benifuuki’green tea beverage with anti-allergic effects[J].J.Sci.Food Agric,2005,85:1606-1612