茶树表没食子儿茶素-3-O-(3-O-甲基)没食子酸酯研究进展
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摘要
表没食子儿茶素-3-O-(3-O-甲基)没食子酸酯(EGCG3"Me)是茶叶中最常检测到的甲基化表没食子儿茶素没食子酸酯(EGCG"Me),具有较表没食子儿茶素没食子酸酯(EGCG)更好的保健功效。本文对EGCG3"Me的理化性质、制备方法、保健功效、茶树EGCG3"Me含量影响因素、EGCG3"Me体内合成路径等国内外研究现状进行了综述,展望EGCG3"Me的体内代谢途径及其深加工产品研发将成为研究热点。
Epigallocatechin-3-O-(3-O-methyl) gallate(EGCG3"Me) is the most common methylated epigallocatechin(EGCG"Me) in tea which is better health function than the epigallocatechin gallate(EGCG).The physical and chemical properties,preparation methods,health care efficacy of EGCG3"Me,influencing factors of EGCG3"Me content of tea tree,in vivo synthesis pathway of EGCG3"Me and other domestic and foreign research status were reviewed.It is suggested that the in vivo metabolic pathway of EGCG3"Me and the creation of deep-processed products will become popular.
Epigallocatechin-3-O-(3-O-methyl) gallate(EGCG3"Me) is the most common methylated epigallocatechin(EGCG"Me) in tea which is better health function than the epigallocatechin gallate(EGCG).The physical and chemical properties,preparation methods,health care efficacy of EGCG3"Me,influencing factors of EGCG3"Me content of tea tree,in vivo synthesis pathway of EGCG3"Me and other domestic and foreign research status were reviewed.It is suggested that the in vivo metabolic pathway of EGCG3"Me and the creation of deep-processed products will become popular.
引文
1 Li YH.Isolation and purification of methylation EGCG from tea plant and cloning and expression of its related genes[D].Hunan:Hunan Agricultural University(湖南农业大学),2013.
2 Chen YL,et al.Research on the relationship of common pollen allergens in patients with allergic diseases[J].Med&Phi:B(医学与哲学:B),2018,(4):1002-0772.
3 MariMaeda Y,et al.O-methylated catechins from tea leaves inhibit mutiple protein kinases in mast cells[J].Immunology,2004,172:4486-4492.
4 Liu M,et al.Research advance in synthesis and pharmacological effects of EGCG derivatives[J].Tea Sci(茶叶科学),2016,2:119-130.
5 Li YH,et al.DPPH radical scavenging capacity by EGCG,EGCG4″Me and EGCG3″Me[J].Farm Prod Proc(农产品加工:学刊),2012,3:26-28.
6 Lv HP,et al.DPPH scavenging activity and total antioxidant activity of methylated EGCG derivatives[J].Food and Ferment Ind(食品与发酵工业),2011,9:166-170.
7 Kurita I,et al.Antihypertensive effect of Benifuuki tea containing O-methylated EGCG[J].J Agric Food Chem,2010,58:1903-1908.
8 Meng XF,et al.Identification and characterization of methylated and ring-fission metabolites of tea catechins formed in humans,mice,and rats[J].Chem Res Toxicol,2002,15:1042-1050.
9 Forester SC,et al.The catechol-O-methyltransferase inhibitor,tolcapone,increases the bioavailability of unmethylated(-)-epigallocatechin-3-gallate in mice[J].J Func Foods,2015,17:183-188.
10 Oritani Y,et al.Comparison of-epigallocatechin-3-O-gallate(EGCG)and O-methylEGCG bioavailability in rats[J].Biol Pharm Bull,2013,36:1577-1582.
11 Sun YL,et al.Study on the analytical method of EGCG 3″Me by HPLC in tea[J].Tea Sci(茶叶科学),2009,5:379-384.
12 Gong ZL,et al.Process for preparing methicatechin from tea leaves:CN101177422A.[P].2008-5-14.
13 Zhou B,et al.Isolation of methylated catechins from tea and their analysis by high performance liquid chromatography[J].Anal Chem(分析化学),2008,36:494-498.
14 Fei DM.Synthesis of methylated EGCG by O-methyltransferase from Camellia Sinensis[D].Zhejiang:Chinese Academy of Agricultural Sciences(中国农业科学院),2011.
15 Liao ZZ.To study the synthesizing methyl derivatives of(-)epigallocatechin-3-gallate and its reversal of multidrug resistance on human hepatocellular carcinoma cells[D].Guangxi:Guangxi Medical University(广西医科大学),2011.
16 Maeda YM,et al.Manufacturing method for low caffeine‘Benifuki’,‘Benihomare’green tea remaining the contents of anti-allergic compounds[J].J Jpn Soci Food Sci Tech(Japan),2004,51:435-439.
17 Chiu FL,et al.HPLC analysis of naturally occurring methylated catechins,3"-and 4"-methyl-epigallocatechin gallate,in various fresh tea leaves and commercial teas and their potent inhibitory effects on inducible nitric oxide synthase in macrophages[J].J Agric Food Chem,2005,53:7035-42.
18 Fujimura Y,et al.Antiallergicteacatechin,(-)-epigallocatechin-3-O-(3-O-methyl)-gallate,suppresses Fc epsilon RI expression in human basophilic KU812 cells[J].J Agric Food Chem,2002,50:5729-5734.
19 Maeda YM,et al.O-methylated catechins from tea leaves inhibit multiple protein kinases in mast cells[J].Immunology,2004,172:4486-4492.
20 Yang Y,et al.In vitro monitoring of the probiotic activity of tea catechins on human intestinal flora[J].Mod Food Sci Tech(现代食品科技),2015,4:128-136.
21 Zhang X,et al.Regulatory effect of tea catechins on intestinal microecology[J].Food Sci(食品科学),2013,5:232-237.
22 Zhang X,et al.Metagenomics analysis of gut microbiota in a high fat diet-induced obesity mouse model fed with-epigallocatechin 3-O-(3-O-methyl)gallate(EGCG3″Me)[J/OL].Mole Nutri&Food Res,2018.
23 Zheng XJ,et al.The modulatory effect of nanocomplexes loaded with EGCG3"Me on intestinal microbiota of high fat die-induced obesity mice model[J].J Food Biochem,2018,42(3):e12501.
24 Fei QQ,et al.In vitro inhibitory effects of oolong tea polyphenols,EGCG and EGCG3"Me onα-glucosidase activity[J].Food Sci(食品科学),2014,21:10-15.
25 Fei QQ.Inhibitory effects of oolong tea polyphenols and their catechins monomers on digestive enzymes and their mechanisms[D].Nanjing:Nanjing Agricultural University(南京农业大学),2015.
26 Yang Y,et al.Effect of methylated tea catechins from chinese oolong tea on the proliferation and differentiation of 3T3-L1preadipocyte[J].Fitoterapia.2015,104:45-49.
27 Kagaya N,et al.Novel function of rare catechin,epigallocatechin-3-(3″-O-methyl)gallate,against cold injury in primary rat hepatocytes[J].Biosci bioengin,2003,96:559-563.
28 Maeda YM,et al.Anti-allergic action of O-methylated EGCGin green tea cultivar Benifuuki[C].5th International Conference on Food Factors(ICo FF),2011.
29 Wang Y.Investigation of methylation of EGCG in tea[D].Chongqing:Southwestern University(西南大学),2006.
30 Lv HP,et al.Analysis of naturally occurring 3″-methyl-epigallocatechin gallate in 71 major tea cultivars grown in china and its processing characteristics[J].J Funct Foods,2014,7:727-736.
31 Li JH,et al.Cluster analysis of the biochemical composition in 53 Sichuan EGCG3"Me tea resources[C].IOP Conference Series:Materials Science and Engineering(MSE).2017,231(1):12125.
32 Li JH,et al.Analysis of 3"-methyl-epigallocatechin gallate in Sichuan tea varieties resources[J].Sci Tech Food Ind(食品工业科技),2015,16:108-113.
33 Lyu HP,et al.Study on the content and variation rule of EGCG3 Me in tea germplasm resources[J].Tea Sci(茶叶科学),2006,4:310-314.
34 Lyu HP,et al.Study of EGCG3"Me content in Zijuan tea[J].Mod Food Sci Tech(现代食品科技),2014(9):286-289.
35 Tang N,et al.Study on high levels of O-methylated EGCG in Hunan tea resources[J].Farm Prod Proc(农产品加工(创新版)),2010,5:36-38.
36 Ji HG,et al.Diverse metabolite variations in tea(Camellia sinensis L.)leaves grown under various shade conditions revisited:a metabolomics study[J].J Agric Food Chem,2018,66:1889-1897.
37 Chen ZY,et al.Effects of small green leafhopper on the content of catechins in tea leaves before and after ingestion[C].Tea industry Symposium on both sides of the Straits(海峡两岸茶业学术研讨会),2010.
38 Sun YL.Study on O-methylated EGCG in tea[D].Nanjing:Nanjing Agricultural University(南京农业大学),2009.
39 Tang N.Study on analysis method and resources of O-methylated EGCG in tea[D].Hunan:Hunan Agricultural University(湖南农业大学),2010.
40 Du HB.QRT-PCR analysis and TLC analysis of methylation of EGCG biosynthesis related genes[D].Hunan:Hunan Agricultural University(湖南农业大学),2014.
41 Chen ZM.Changes of methylation of catechin in tea plant[J].Chinese Tea(中国茶叶),2004,4:40.
42 Guo ZH,et al.Effects of different processing methods on the content and antioxidant activity of main catechins in taiwan characteristic tea varietie[C].Tea industry Symposium on both sides of the Straits(海峡两岸茶业学术研讨会),2010.
43 Luo ZF,et al.Studies on O-methylated epigallocatechin-3-O-gallate in tea[J].J Southwest Univ:Nat Sci(西南大学学报:自科版),2008,30(3):56-59.
44 Li JH,et al.Determination of methylated catechins in Sichuan green tea,yellow tea,dark tea,black tea and green tea by high performance liquid chromatography-diode array detection method[J].Sci Tech Food Ind(食品工业科技),2018(5):261-267.
45 Wu YJ,et al.Synthesis of methylated EGCG and its stability in artificial simulation gastric juice and artificial simulation intestinal juice[J].J Anhui Agric Univ(安徽农业大学学报),2010,4:688-691.
46 Wan J.Design,synthesis and activity evaluation of methylated polyphenol derivatives as MDR reversal agents[D].Shandong:Ocean University of China(中国海洋大学),2012.
47 Fei DM,et al.Study on expression conditions of EGCG-O-methyltransferase in recombinant escherichia coli bacteria[J].Tea Sci(茶叶科学),2011,4:333-340.
48 Zhang Y,et al.Cloning of a caffeoyl-coenzyme a O-methyltransferase from Camellia sinensis and analysis of its catalytic activity[J].J Zhejiang Univ:Sci B(浙江大学学报B),2015,16:103-112.
49 Masami N,et al.Determination of theaflavins including methylated theaflavins in black tea leaves by solid-phase extraction and HPLC analysis[J].J Agric Food Chem,2007,55:7252-7257.
50 Ji HG,et al.Metabolic phenotyping of various tea(Camellia sinensis L.)cultivars and understanding of their intrinsic metabolism[J].Food Chem,2017,233:321-330.
51 Luo Y,et al.Characterization of the transcriptional regulator Csb HLH62 that negatively regulates EGCG3"Me biosynthesis in Camellia sinensis[J].Gene,2019,699:8-15.
52 Lee SC,et al.Screen and genetic assessment of tea germplasms with elevated methylated catechin,(-)-epigallocatechin-3-O-(3-O-methyl)gallate[J].J Agric Food Chem,2009,57:8906-8912.
2 Chen YL,et al.Research on the relationship of common pollen allergens in patients with allergic diseases[J].Med&Phi:B(医学与哲学:B),2018,(4):1002-0772.
3 MariMaeda Y,et al.O-methylated catechins from tea leaves inhibit mutiple protein kinases in mast cells[J].Immunology,2004,172:4486-4492.
4 Liu M,et al.Research advance in synthesis and pharmacological effects of EGCG derivatives[J].Tea Sci(茶叶科学),2016,2:119-130.
5 Li YH,et al.DPPH radical scavenging capacity by EGCG,EGCG4″Me and EGCG3″Me[J].Farm Prod Proc(农产品加工:学刊),2012,3:26-28.
6 Lv HP,et al.DPPH scavenging activity and total antioxidant activity of methylated EGCG derivatives[J].Food and Ferment Ind(食品与发酵工业),2011,9:166-170.
7 Kurita I,et al.Antihypertensive effect of Benifuuki tea containing O-methylated EGCG[J].J Agric Food Chem,2010,58:1903-1908.
8 Meng XF,et al.Identification and characterization of methylated and ring-fission metabolites of tea catechins formed in humans,mice,and rats[J].Chem Res Toxicol,2002,15:1042-1050.
9 Forester SC,et al.The catechol-O-methyltransferase inhibitor,tolcapone,increases the bioavailability of unmethylated(-)-epigallocatechin-3-gallate in mice[J].J Func Foods,2015,17:183-188.
10 Oritani Y,et al.Comparison of-epigallocatechin-3-O-gallate(EGCG)and O-methylEGCG bioavailability in rats[J].Biol Pharm Bull,2013,36:1577-1582.
11 Sun YL,et al.Study on the analytical method of EGCG 3″Me by HPLC in tea[J].Tea Sci(茶叶科学),2009,5:379-384.
12 Gong ZL,et al.Process for preparing methicatechin from tea leaves:CN101177422A.[P].2008-5-14.
13 Zhou B,et al.Isolation of methylated catechins from tea and their analysis by high performance liquid chromatography[J].Anal Chem(分析化学),2008,36:494-498.
14 Fei DM.Synthesis of methylated EGCG by O-methyltransferase from Camellia Sinensis[D].Zhejiang:Chinese Academy of Agricultural Sciences(中国农业科学院),2011.
15 Liao ZZ.To study the synthesizing methyl derivatives of(-)epigallocatechin-3-gallate and its reversal of multidrug resistance on human hepatocellular carcinoma cells[D].Guangxi:Guangxi Medical University(广西医科大学),2011.
16 Maeda YM,et al.Manufacturing method for low caffeine‘Benifuki’,‘Benihomare’green tea remaining the contents of anti-allergic compounds[J].J Jpn Soci Food Sci Tech(Japan),2004,51:435-439.
17 Chiu FL,et al.HPLC analysis of naturally occurring methylated catechins,3"-and 4"-methyl-epigallocatechin gallate,in various fresh tea leaves and commercial teas and their potent inhibitory effects on inducible nitric oxide synthase in macrophages[J].J Agric Food Chem,2005,53:7035-42.
18 Fujimura Y,et al.Antiallergicteacatechin,(-)-epigallocatechin-3-O-(3-O-methyl)-gallate,suppresses Fc epsilon RI expression in human basophilic KU812 cells[J].J Agric Food Chem,2002,50:5729-5734.
19 Maeda YM,et al.O-methylated catechins from tea leaves inhibit multiple protein kinases in mast cells[J].Immunology,2004,172:4486-4492.
20 Yang Y,et al.In vitro monitoring of the probiotic activity of tea catechins on human intestinal flora[J].Mod Food Sci Tech(现代食品科技),2015,4:128-136.
21 Zhang X,et al.Regulatory effect of tea catechins on intestinal microecology[J].Food Sci(食品科学),2013,5:232-237.
22 Zhang X,et al.Metagenomics analysis of gut microbiota in a high fat diet-induced obesity mouse model fed with-epigallocatechin 3-O-(3-O-methyl)gallate(EGCG3″Me)[J/OL].Mole Nutri&Food Res,2018.
23 Zheng XJ,et al.The modulatory effect of nanocomplexes loaded with EGCG3"Me on intestinal microbiota of high fat die-induced obesity mice model[J].J Food Biochem,2018,42(3):e12501.
24 Fei QQ,et al.In vitro inhibitory effects of oolong tea polyphenols,EGCG and EGCG3"Me onα-glucosidase activity[J].Food Sci(食品科学),2014,21:10-15.
25 Fei QQ.Inhibitory effects of oolong tea polyphenols and their catechins monomers on digestive enzymes and their mechanisms[D].Nanjing:Nanjing Agricultural University(南京农业大学),2015.
26 Yang Y,et al.Effect of methylated tea catechins from chinese oolong tea on the proliferation and differentiation of 3T3-L1preadipocyte[J].Fitoterapia.2015,104:45-49.
27 Kagaya N,et al.Novel function of rare catechin,epigallocatechin-3-(3″-O-methyl)gallate,against cold injury in primary rat hepatocytes[J].Biosci bioengin,2003,96:559-563.
28 Maeda YM,et al.Anti-allergic action of O-methylated EGCGin green tea cultivar Benifuuki[C].5th International Conference on Food Factors(ICo FF),2011.
29 Wang Y.Investigation of methylation of EGCG in tea[D].Chongqing:Southwestern University(西南大学),2006.
30 Lv HP,et al.Analysis of naturally occurring 3″-methyl-epigallocatechin gallate in 71 major tea cultivars grown in china and its processing characteristics[J].J Funct Foods,2014,7:727-736.
31 Li JH,et al.Cluster analysis of the biochemical composition in 53 Sichuan EGCG3"Me tea resources[C].IOP Conference Series:Materials Science and Engineering(MSE).2017,231(1):12125.
32 Li JH,et al.Analysis of 3"-methyl-epigallocatechin gallate in Sichuan tea varieties resources[J].Sci Tech Food Ind(食品工业科技),2015,16:108-113.
33 Lyu HP,et al.Study on the content and variation rule of EGCG3 Me in tea germplasm resources[J].Tea Sci(茶叶科学),2006,4:310-314.
34 Lyu HP,et al.Study of EGCG3"Me content in Zijuan tea[J].Mod Food Sci Tech(现代食品科技),2014(9):286-289.
35 Tang N,et al.Study on high levels of O-methylated EGCG in Hunan tea resources[J].Farm Prod Proc(农产品加工(创新版)),2010,5:36-38.
36 Ji HG,et al.Diverse metabolite variations in tea(Camellia sinensis L.)leaves grown under various shade conditions revisited:a metabolomics study[J].J Agric Food Chem,2018,66:1889-1897.
37 Chen ZY,et al.Effects of small green leafhopper on the content of catechins in tea leaves before and after ingestion[C].Tea industry Symposium on both sides of the Straits(海峡两岸茶业学术研讨会),2010.
38 Sun YL.Study on O-methylated EGCG in tea[D].Nanjing:Nanjing Agricultural University(南京农业大学),2009.
39 Tang N.Study on analysis method and resources of O-methylated EGCG in tea[D].Hunan:Hunan Agricultural University(湖南农业大学),2010.
40 Du HB.QRT-PCR analysis and TLC analysis of methylation of EGCG biosynthesis related genes[D].Hunan:Hunan Agricultural University(湖南农业大学),2014.
41 Chen ZM.Changes of methylation of catechin in tea plant[J].Chinese Tea(中国茶叶),2004,4:40.
42 Guo ZH,et al.Effects of different processing methods on the content and antioxidant activity of main catechins in taiwan characteristic tea varietie[C].Tea industry Symposium on both sides of the Straits(海峡两岸茶业学术研讨会),2010.
43 Luo ZF,et al.Studies on O-methylated epigallocatechin-3-O-gallate in tea[J].J Southwest Univ:Nat Sci(西南大学学报:自科版),2008,30(3):56-59.
44 Li JH,et al.Determination of methylated catechins in Sichuan green tea,yellow tea,dark tea,black tea and green tea by high performance liquid chromatography-diode array detection method[J].Sci Tech Food Ind(食品工业科技),2018(5):261-267.
45 Wu YJ,et al.Synthesis of methylated EGCG and its stability in artificial simulation gastric juice and artificial simulation intestinal juice[J].J Anhui Agric Univ(安徽农业大学学报),2010,4:688-691.
46 Wan J.Design,synthesis and activity evaluation of methylated polyphenol derivatives as MDR reversal agents[D].Shandong:Ocean University of China(中国海洋大学),2012.
47 Fei DM,et al.Study on expression conditions of EGCG-O-methyltransferase in recombinant escherichia coli bacteria[J].Tea Sci(茶叶科学),2011,4:333-340.
48 Zhang Y,et al.Cloning of a caffeoyl-coenzyme a O-methyltransferase from Camellia sinensis and analysis of its catalytic activity[J].J Zhejiang Univ:Sci B(浙江大学学报B),2015,16:103-112.
49 Masami N,et al.Determination of theaflavins including methylated theaflavins in black tea leaves by solid-phase extraction and HPLC analysis[J].J Agric Food Chem,2007,55:7252-7257.
50 Ji HG,et al.Metabolic phenotyping of various tea(Camellia sinensis L.)cultivars and understanding of their intrinsic metabolism[J].Food Chem,2017,233:321-330.
51 Luo Y,et al.Characterization of the transcriptional regulator Csb HLH62 that negatively regulates EGCG3"Me biosynthesis in Camellia sinensis[J].Gene,2019,699:8-15.
52 Lee SC,et al.Screen and genetic assessment of tea germplasms with elevated methylated catechin,(-)-epigallocatechin-3-O-(3-O-methyl)gallate[J].J Agric Food Chem,2009,57:8906-8912.