普洱熟茶化学成分研究进展
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摘要
普洱熟茶是一种独特的微生物发酵茶,由中国云南省的大叶种茶的晒干叶制成,为中国特有名茶。近年来,普洱熟茶由于其降血脂、抗氧化、减肥、抗菌等多重保健功效而备受欢迎,目前已从普洱熟茶中分离出多种功能性成分并进行了验证。该文综述了近年来国内外对普洱熟茶化学成分及主要化学成分转化的研究,特别是普洱茶中特有的加成儿茶素类成分,为进一步研究普洱熟茶的生物活性物质及其形成机制提供了一定的理论基础。
Pu-erh tea is a special microbial fermented tea produced from sun-dried leaves of large-leaf tea species(Camellia assamica) in Yunnan province,China. Pu-erh tea has become increasingly popular in recent years,which due to its multiple health benefits,such as hypolipidemic,antioxidant,antiobesity and antibacterial effects. Many functional components of Pu-erh tea have been isolated and identified,the chemical constituents and transformations of major chemical components of Pu-erh tea,especially substituted catechins,were reviewed and discussed in this paper. This review aimed to provide a theoretical basis for further investigation on bioactive compounds of Pu-erh tea and their formation mechanisms.
Pu-erh tea is a special microbial fermented tea produced from sun-dried leaves of large-leaf tea species(Camellia assamica) in Yunnan province,China. Pu-erh tea has become increasingly popular in recent years,which due to its multiple health benefits,such as hypolipidemic,antioxidant,antiobesity and antibacterial effects. Many functional components of Pu-erh tea have been isolated and identified,the chemical constituents and transformations of major chemical components of Pu-erh tea,especially substituted catechins,were reviewed and discussed in this paper. This review aimed to provide a theoretical basis for further investigation on bioactive compounds of Pu-erh tea and their formation mechanisms.
引文
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[3]曹冠华,王文光,孔楠,等.普洱茶中主要微生物与品质的关系及发酵方法优化的探讨[J].茶叶学报,2011(4):1-5.
[4]冯玲然,王强,罗玮,等.普洱茶中功能性微生物的筛选及其对普洱茶感官品质的影响[J].生物加工过程,2015(2):93-97.
[5]ZHANG W,YANG R,FANG W,et al.Characterization of thermophilic fungal community associated with pile fermentation of Pu-erh tea[J].International Journal of Food Microbiology,2016,227:29-33.
[6]SHAO W,POWELL C,CLIFFORD M N.The analysis by HPLC of green,black and Pu'er teas produced in Yunnan[J].Journal of the Science of Food&Agriculture,2010,69(4):535-540.
[7]WANG K,FANG L,LIU Z,et al.Comparison of catechins and volatile compounds among different types of tea using high performance liquid chromatograph and gas chromatograph mass spectrometer[J].International Journal of Food Science&Technology,2011,46(7):1 406-1 412.
[8]LIANG Y,ZHANG L,LU J.A study on chemical estimation of pu-erh tea quality[J].Journal of the Science of Food&Agriculture,2005,85(3):381-390.
[9]TANAKA T,UMEKI H,NAGAI S,et al.Transformation of tea catechins and flavonoid glycosides by treatment with Japanese post-fermented tea acetone powder[J].Food Chemistry,2012,134(1):276-281.
[10]ZHANG C,SUEN C L C,YANG C,et al.Antioxidant capacity and major polyphenol composition of teas as affected by geographical location,plantation elevation and leaf grade[J].Food Chemistry,2018,244:109-119.
[11]GRZESIK M,NAPARO K,BARTOSZ G,et al.Antioxidant properties of catechins:Comparison with other antioxidants[J].Food Chemistry,2018,241:480-492.
[12]王淑敏,门田重利,刘志强,等.沱茶中抗自由基化学成分的研究[J].天然产物研究与开发,2005,17(2):131-137.
[13]ZHAO Y,YANG L,HUANG Z,et al.Synergistic effects of caffeine and catechins on lipid metabolism in chronically fed mice via the AMP-activated protein kinase signaling pathway[J].European Journal of Nutrition,2017,56(7):2 309-2 318.
[14]YI W,XIE X,DU M,et al.Green tea polyphenols ameliorate the early renal damage induced by a high-fat diet via ketogenesis/sirt3 pathway[J].Oxidative Medicine and Cellular Longevity,2017,2017:1-14.
[15]东方,杨子银,何普明,等.普洱茶抗氧化活性成分的LC-MS分析[J].中国食品学报,2008,8(2):133-141.
[16]ZHOU Z H,ZHANG Y J,XU M,et al.Puerins A and B,two new 8-C substituted flavan-3-ols from Pu-er tea[J].Journal of Agricultural&Food Chemistry,2005,53(22):8 614-8 617.
[17]WANG W,ZHANG L,WANG S,et al.8-C N-ethyl-2-pyrrolidinone substituted flavan-3-ols as the marker compounds of Chinese dark teas formed in the post-fermentation process provide significant antioxidative activity[J].Food Chem,2014,152:539-545.
[18]TIAN L W,TAO M K,XU M,et al.Carboxymethyl-and carboxyl-catechins from ripe Pu-er tea[J].Journal of Agricultural&Food Chemistry,2014,62(50):12 229-12 234.
[19]张云天,姚晓玲,鲁江,等.黑茶茶褐素的研究现状及进展[J].食品工业科技,2017,38(11):395-399.
[20]XIE G,YE M,WANG Y G,et al.Characterization of pu-erh tea using chemical and metabolic profiling approaches[J].Journal of Agricultural&Food Chemistry,2009,57(8):3 046-3 054.
[21]GONG J S,TANG C,PENG C X.Characterization of the chemical differences between solvent extracts from Pu-erh tea and Dian Hong black tea by CP-Py-GC/MS[J].Journal of Analytical&Applied Pyrolysis,2012,95:189-197.
[22]谭超,彭春秀,高斌,等.普洱茶茶褐素类主要组分特征及光谱学性质研究[J].光谱学与光谱分析,2012,32(4):1 051-1 056.
[23]WANG Y,ZHANG M,ZHANG Z,et al.High-theabrownins instant dark tea product by Aspergillus niger via submerged fermentation:α-glucosidase and pancreatic lipase inhibition and antioxidant activity[J].J Sci Food Agric,2017,97(15):5 100-5 106.
[24]徐湘婷,王鹏,罗绍忠,等.普洱熟茶茶褐素对2型糖尿病小鼠降糖作用研究[J].中国民族民间医药,2015(20):9-10.
[25]岳随娟,刘建,龚加顺.普洱茶茶褐素对大鼠肠道菌群的影响[J].茶叶科学,2016,36(3):261-267.
[26]龚加顺,陈文品,周红杰,等.云南普洱茶特征成分的功能与毒理学评价[J].茶叶科学,2007,27(3):201-210.
[27]林智,吕海鹏,崔文锐,等.普洱茶的抗氧化酚类化学成分的研究[J].茶叶科学,2006,26(2):112-116.
[28]ZHANG L,LI N,MA Z Z,et al.Comparison of the chemical constituents of aged pu-erh tea,ripened pu-erh tea,and other teas using HPLC-DAD-ESI-MSn[J].Journal of Agricultural&Food Chemistry,2011,59(16):8754-8 760.
[29]吕海鹏,林智,钟秋生,等.普洱茶E8组分的化学成分研究[J].茶叶科学,2010,30(6):423-428.
[30]刘通讯,谭梦珠.不同储存时间对普洱茶有机溶剂萃取物清除自由基活性的影响[J].现代食品科技,2013(10):2 372-2 377.
[31]XU Y Q,WANG C,LI C W,et al.Characterization of aroma-active compounds of Pu-erh tea by headspace solidphase microextraction(HS-SPME)and simultaneous distillation-extraction(SDE)coupled with GC-olfactometry and GC-MS[J].Food Analytical Methods,2016,9(5):1 188-1 199.
[32]曹艳妮,刘通讯.普洱生茶和熟茶香气中萜烯类和甲氧基苯类成分分析[J].食品工业科技,2012,33(5):128-130.
[33]WANG Q,PENG C,GONG J.Effects of enzymatic action on the formation of theabrownin during solid state fermentation of Pu-erh tea[J].Journal of the Science of Food&Agriculture,2011,91(13):2 412-2 418.
[34]陈梅春,张海峰,潘志针,等.陈年普洱茶香气成分及清除DPPH自由基活性研究[J].中国农学通报,2015,31(4):274-279.
[35]KAWAKAMI M,SHIBAMOTO T.The volatile constituents of piled tea:Toyama kurocha[J].Journal of the Agricultural Chemical Society of Japan,2006,55(7):1 839-1 847.
[36]YAMAUCHI H,DOI M.O-methylation of 2,6-dimethoxy-4-methylphenol by Aspergillus glaucus and their possible contribution to Katsuobushi flavor[J].Journal of the Agricultural Chemical Society of Japan,1997,61(8):1 386-1 387.
[37]折改梅,陈可可,张颖君,等.8-氧化咖啡因和嘧啶类生物碱在普洱熟茶中的存在[J].植物分类与资源学报,2007,29(6):713-716.
[38]HULL C,HUGHES S,JALBERT R,et al.Analysis of catechin and methylxanthine composition in tea(Camellia sinensis)by high pressure liquid chromatography[C]//255th ACS National Meeting&Exposition.LA:American Chemical Society,2018:CHED-383.
[39]HWANG L S,LIN L C,CHEN N T,et al.Hypolipidemic effect and antiatherogenic potential of Pu-Erh tea[J].Acs Symposium,2003,859:87-103.
[40]吕海鹏,张悦,杨停,等.普洱茶滋味品质化学成分分析[J].食品与发酵工业,2016,42(2):178-183.
[41]ALCZAR A,BALLESTEROS O,JURADO J M,et al.Differentiation of green,white,black,oolong,and Puerh teas according to their free amino acids content[J].JAgric Food Chem,2007,55(15):5 960-5 965.
[42]田洋,肖蓉,徐昆龙,等.普洱茶加工过程中主要成分变化及相关性研究[J].食品科学,2010,31(11):20-24.
[43]ANANINGSIH V K,SHARMA A,ZHOU W.Green tea catechins during food processing and storage:A review on stability and detection[J].Food Research International,2013,50(2):469-479.
[44]李家华,赵明,胡艳萍,等.普洱茶发酵过程中黄酮醇类物质含量变化的研究[J].西南大学学报(自然科学版),2012,34(2):59-65.
[45]WANG D,XIAO R,HU X,et al.Comparative safety evaluation of Chinese Pu-erh green tea extract and Pu-erh black tea extract in Wistar rats[J].Journal of Agricultural&Food Chemistry,2010,58(2):1 350-1 358.
[46]JENG K C,CHEN C S,FANG Y P,et al.Effect of microbial fermentation on content of statin,GABA,and polyphenols in Pu-erh tea[J].Journal of Agricultural&Food Chemistry,2007,55(21):8 787-8 792.
[47]JIANG C,ZENG Z,HUANG Y,et al.Chemical compositions of Pu'er tea fermented by Eurotium Cristatum and their lipid-lowering activity[J].LWT-Food Science and Technology,2018,98:204-211.
[48]XIE J,YU H,SONG S,et al.Pu-erh tea water extract mediates cell cycle arrest and apoptosis in MDA-MB-231human breast cancer cells[J].Frontiers in Pharmacology,2017,8(E547):190.
[49]JIE G,LIN Z,ZHANG L,et al.Free radical scavenging effect of Pu-erh tea extracts and their protective effect on oxidative damage in human fibroblast cells[J].Journal of Agricultural&Food Chemistry,2006,54(21):8 058-8 058.
[2]JIANG H Y,SHII T,MATSUO Y,et al.A new catechin oxidation product and polymeric polyphenols of post-fermented tea[J].Food Chemistry,2011,129(3):830-836.
[3]曹冠华,王文光,孔楠,等.普洱茶中主要微生物与品质的关系及发酵方法优化的探讨[J].茶叶学报,2011(4):1-5.
[4]冯玲然,王强,罗玮,等.普洱茶中功能性微生物的筛选及其对普洱茶感官品质的影响[J].生物加工过程,2015(2):93-97.
[5]ZHANG W,YANG R,FANG W,et al.Characterization of thermophilic fungal community associated with pile fermentation of Pu-erh tea[J].International Journal of Food Microbiology,2016,227:29-33.
[6]SHAO W,POWELL C,CLIFFORD M N.The analysis by HPLC of green,black and Pu'er teas produced in Yunnan[J].Journal of the Science of Food&Agriculture,2010,69(4):535-540.
[7]WANG K,FANG L,LIU Z,et al.Comparison of catechins and volatile compounds among different types of tea using high performance liquid chromatograph and gas chromatograph mass spectrometer[J].International Journal of Food Science&Technology,2011,46(7):1 406-1 412.
[8]LIANG Y,ZHANG L,LU J.A study on chemical estimation of pu-erh tea quality[J].Journal of the Science of Food&Agriculture,2005,85(3):381-390.
[9]TANAKA T,UMEKI H,NAGAI S,et al.Transformation of tea catechins and flavonoid glycosides by treatment with Japanese post-fermented tea acetone powder[J].Food Chemistry,2012,134(1):276-281.
[10]ZHANG C,SUEN C L C,YANG C,et al.Antioxidant capacity and major polyphenol composition of teas as affected by geographical location,plantation elevation and leaf grade[J].Food Chemistry,2018,244:109-119.
[11]GRZESIK M,NAPARO K,BARTOSZ G,et al.Antioxidant properties of catechins:Comparison with other antioxidants[J].Food Chemistry,2018,241:480-492.
[12]王淑敏,门田重利,刘志强,等.沱茶中抗自由基化学成分的研究[J].天然产物研究与开发,2005,17(2):131-137.
[13]ZHAO Y,YANG L,HUANG Z,et al.Synergistic effects of caffeine and catechins on lipid metabolism in chronically fed mice via the AMP-activated protein kinase signaling pathway[J].European Journal of Nutrition,2017,56(7):2 309-2 318.
[14]YI W,XIE X,DU M,et al.Green tea polyphenols ameliorate the early renal damage induced by a high-fat diet via ketogenesis/sirt3 pathway[J].Oxidative Medicine and Cellular Longevity,2017,2017:1-14.
[15]东方,杨子银,何普明,等.普洱茶抗氧化活性成分的LC-MS分析[J].中国食品学报,2008,8(2):133-141.
[16]ZHOU Z H,ZHANG Y J,XU M,et al.Puerins A and B,two new 8-C substituted flavan-3-ols from Pu-er tea[J].Journal of Agricultural&Food Chemistry,2005,53(22):8 614-8 617.
[17]WANG W,ZHANG L,WANG S,et al.8-C N-ethyl-2-pyrrolidinone substituted flavan-3-ols as the marker compounds of Chinese dark teas formed in the post-fermentation process provide significant antioxidative activity[J].Food Chem,2014,152:539-545.
[18]TIAN L W,TAO M K,XU M,et al.Carboxymethyl-and carboxyl-catechins from ripe Pu-er tea[J].Journal of Agricultural&Food Chemistry,2014,62(50):12 229-12 234.
[19]张云天,姚晓玲,鲁江,等.黑茶茶褐素的研究现状及进展[J].食品工业科技,2017,38(11):395-399.
[20]XIE G,YE M,WANG Y G,et al.Characterization of pu-erh tea using chemical and metabolic profiling approaches[J].Journal of Agricultural&Food Chemistry,2009,57(8):3 046-3 054.
[21]GONG J S,TANG C,PENG C X.Characterization of the chemical differences between solvent extracts from Pu-erh tea and Dian Hong black tea by CP-Py-GC/MS[J].Journal of Analytical&Applied Pyrolysis,2012,95:189-197.
[22]谭超,彭春秀,高斌,等.普洱茶茶褐素类主要组分特征及光谱学性质研究[J].光谱学与光谱分析,2012,32(4):1 051-1 056.
[23]WANG Y,ZHANG M,ZHANG Z,et al.High-theabrownins instant dark tea product by Aspergillus niger via submerged fermentation:α-glucosidase and pancreatic lipase inhibition and antioxidant activity[J].J Sci Food Agric,2017,97(15):5 100-5 106.
[24]徐湘婷,王鹏,罗绍忠,等.普洱熟茶茶褐素对2型糖尿病小鼠降糖作用研究[J].中国民族民间医药,2015(20):9-10.
[25]岳随娟,刘建,龚加顺.普洱茶茶褐素对大鼠肠道菌群的影响[J].茶叶科学,2016,36(3):261-267.
[26]龚加顺,陈文品,周红杰,等.云南普洱茶特征成分的功能与毒理学评价[J].茶叶科学,2007,27(3):201-210.
[27]林智,吕海鹏,崔文锐,等.普洱茶的抗氧化酚类化学成分的研究[J].茶叶科学,2006,26(2):112-116.
[28]ZHANG L,LI N,MA Z Z,et al.Comparison of the chemical constituents of aged pu-erh tea,ripened pu-erh tea,and other teas using HPLC-DAD-ESI-MSn[J].Journal of Agricultural&Food Chemistry,2011,59(16):8754-8 760.
[29]吕海鹏,林智,钟秋生,等.普洱茶E8组分的化学成分研究[J].茶叶科学,2010,30(6):423-428.
[30]刘通讯,谭梦珠.不同储存时间对普洱茶有机溶剂萃取物清除自由基活性的影响[J].现代食品科技,2013(10):2 372-2 377.
[31]XU Y Q,WANG C,LI C W,et al.Characterization of aroma-active compounds of Pu-erh tea by headspace solidphase microextraction(HS-SPME)and simultaneous distillation-extraction(SDE)coupled with GC-olfactometry and GC-MS[J].Food Analytical Methods,2016,9(5):1 188-1 199.
[32]曹艳妮,刘通讯.普洱生茶和熟茶香气中萜烯类和甲氧基苯类成分分析[J].食品工业科技,2012,33(5):128-130.
[33]WANG Q,PENG C,GONG J.Effects of enzymatic action on the formation of theabrownin during solid state fermentation of Pu-erh tea[J].Journal of the Science of Food&Agriculture,2011,91(13):2 412-2 418.
[34]陈梅春,张海峰,潘志针,等.陈年普洱茶香气成分及清除DPPH自由基活性研究[J].中国农学通报,2015,31(4):274-279.
[35]KAWAKAMI M,SHIBAMOTO T.The volatile constituents of piled tea:Toyama kurocha[J].Journal of the Agricultural Chemical Society of Japan,2006,55(7):1 839-1 847.
[36]YAMAUCHI H,DOI M.O-methylation of 2,6-dimethoxy-4-methylphenol by Aspergillus glaucus and their possible contribution to Katsuobushi flavor[J].Journal of the Agricultural Chemical Society of Japan,1997,61(8):1 386-1 387.
[37]折改梅,陈可可,张颖君,等.8-氧化咖啡因和嘧啶类生物碱在普洱熟茶中的存在[J].植物分类与资源学报,2007,29(6):713-716.
[38]HULL C,HUGHES S,JALBERT R,et al.Analysis of catechin and methylxanthine composition in tea(Camellia sinensis)by high pressure liquid chromatography[C]//255th ACS National Meeting&Exposition.LA:American Chemical Society,2018:CHED-383.
[39]HWANG L S,LIN L C,CHEN N T,et al.Hypolipidemic effect and antiatherogenic potential of Pu-Erh tea[J].Acs Symposium,2003,859:87-103.
[40]吕海鹏,张悦,杨停,等.普洱茶滋味品质化学成分分析[J].食品与发酵工业,2016,42(2):178-183.
[41]ALCZAR A,BALLESTEROS O,JURADO J M,et al.Differentiation of green,white,black,oolong,and Puerh teas according to their free amino acids content[J].JAgric Food Chem,2007,55(15):5 960-5 965.
[42]田洋,肖蓉,徐昆龙,等.普洱茶加工过程中主要成分变化及相关性研究[J].食品科学,2010,31(11):20-24.
[43]ANANINGSIH V K,SHARMA A,ZHOU W.Green tea catechins during food processing and storage:A review on stability and detection[J].Food Research International,2013,50(2):469-479.
[44]李家华,赵明,胡艳萍,等.普洱茶发酵过程中黄酮醇类物质含量变化的研究[J].西南大学学报(自然科学版),2012,34(2):59-65.
[45]WANG D,XIAO R,HU X,et al.Comparative safety evaluation of Chinese Pu-erh green tea extract and Pu-erh black tea extract in Wistar rats[J].Journal of Agricultural&Food Chemistry,2010,58(2):1 350-1 358.
[46]JENG K C,CHEN C S,FANG Y P,et al.Effect of microbial fermentation on content of statin,GABA,and polyphenols in Pu-erh tea[J].Journal of Agricultural&Food Chemistry,2007,55(21):8 787-8 792.
[47]JIANG C,ZENG Z,HUANG Y,et al.Chemical compositions of Pu'er tea fermented by Eurotium Cristatum and their lipid-lowering activity[J].LWT-Food Science and Technology,2018,98:204-211.
[48]XIE J,YU H,SONG S,et al.Pu-erh tea water extract mediates cell cycle arrest and apoptosis in MDA-MB-231human breast cancer cells[J].Frontiers in Pharmacology,2017,8(E547):190.
[49]JIE G,LIN Z,ZHANG L,et al.Free radical scavenging effect of Pu-erh tea extracts and their protective effect on oxidative damage in human fibroblast cells[J].Journal of Agricultural&Food Chemistry,2006,54(21):8 058-8 058.
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