天然结合酚的研究进展
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摘要
植物化学成分中,酚类化合物由于其益生效果显著已得到广泛的研究,包括可溶性多酚和不溶性多酚,其中结合酚主要以共价化合物的形式存在于细胞壁中,较难直接被释放出来。因此,相对于可溶性多酚层出不穷的报道,结合酚常常被忽略,文章对结合酚的形成机理、提取方法、生物活性以及应用进行了归纳与阐述,旨在更有效地利用结合酚。
In the chemical composition of plants,phenolic compounds have been extensively studied due to their remarkable probiotic effects,including soluble polyphenols and insoluble polyphenols.Insoluble polyphenols mainly exist in the cell wall in the form of covalent compounds,which are difficult to release directly.Therefore,compared with the study of soluble polyphenols,combined phenolic compounds are often ignored.In order to use combined phenols more effectively,the formation mechanism,extraction methods,biological activities and application of the combined phenols are summarized and expounded.
In the chemical composition of plants,phenolic compounds have been extensively studied due to their remarkable probiotic effects,including soluble polyphenols and insoluble polyphenols.Insoluble polyphenols mainly exist in the cell wall in the form of covalent compounds,which are difficult to release directly.Therefore,compared with the study of soluble polyphenols,combined phenolic compounds are often ignored.In order to use combined phenols more effectively,the formation mechanism,extraction methods,biological activities and application of the combined phenols are summarized and expounded.
引文
[1]Nayak B,Rui H L,Tang J.Effect of processing on phenolic antioxidants of fruits,vegetables,and grains—a review[J].Critical Reviews in Food Science and Nutrition,2015,55(7):887-919.
[2]Lee J,Chan B L,Mitchell A E.Identification/quantification of free and bound phenolic acids in peel and pulp of apples(Malus domestica)using high resolution mass spectrometry(HRMS)[J].Food Chemistry,2017,215:301-310.
[3]Chandrasekara A,Shahidi F.Content of insoluble bound phenolics in millets and their contribution to antioxidant capacity[J].Journal of Agricultural&Food Chemistry,2010,58(11):6706-6714.
[4]Chen G L,Zhang X,Chen S G,et al.Antioxidant activities and contents of free,esterified and insoluble-bound phenolics in 14subtropical fruit leaves collected from the south of China[J].Journal of Functional Foods,2017,30:290-302.
[5]原田,刘邻渭,高忠梅,等.石榴皮游离与结合态多酚的组成和抗氧化性研究[J].食品工业科技,2014,35(18):161-166.
[6]Wukitch S J,Boivin R L,Bonoli P T,et al.Investigation of performance limiting phenomena in a variable phase ICRF antenna in Alcator C-Mod[J].Plasma Physics&Controlled Fusion,2004,46(9):1479-1491.
[7]Holtekjolen A K,Kinitz C,Knutsen S H.Flavanol and bound phenolic acid contents in different barley varieties[J].Journal of Agricultural&Food Chemistry,2006,54(6):2253-2260.
[8]Y F,Sun J,Wu X,et al.Antioxidant and antiproliferative activities of common vegetables[J].Journal of Agricultural&Food Chemistry,2002,50(25):7449-7454.
[9]Fu-Hua L I,Guo X H,Xia C Y,et al.Research advance in antioxidant activity of phenolic compounds in whole grains[J].Food Science,2012,33(13):299-304.
[10]Carrete M,Gil-Sánchez J M.Analysis of nonextractable phenolic compounds in foods:the current state of the art[J].Journal of Agricultural&Food Chemistry,2011,59(24):12713-12724.
[11]Vaher M,Matso K,Levandi T,et al.Phenolic compounds and the antioxidant activity of the bran,flour and whole grain of different wheat varieties[J].Procedia Chemistry,2010,2(1):76-82.
[12]王兰.黄淮麦区小麦主栽品种酚酸含量分析及磨粉对酚酸含量的影响[D].北京:中国农业科学院,2011.
[13]Ayoub M,Camargo A C D,Shahidi F.Antioxidants and bioactivities of free,esterified and insoluble-bound phenolics from berry seed meals[J].Food Chemistry,2016,197:221-232.
[14]Wang B N,Liu H F,Zheng J B,et al.Distribution of phenolic acids in different tissues of jujube and their antioxidant activity[J].Journal of Agricultural&Food Chemistry,2011,59(4):1288-1292.
[15]Camargo A C D,Gallo C R,Shahidi F.Gamma-irradiation induced changes in microbiological status,phenolic profile and antioxidant activity of peanut skin[J].Journal of Functional Foods,2015,(12):129-143.
[16]Kim I H,Chun H S.Composition of fatty acid and phenolic acid in rice with the different milling fractions[J].Journal of the Korean Society of Food Science&Nutrition,1996,10(4):350-357.
[17]Albishi T,John J A,Al-Khalifa A S,et al.Antioxidative phenolic constituents of skins of onion varieties and their activities[J].Journal of Functional Foods,2013,5(3):1191-1203.
[18]Martinoia E,Ratajczak R.Transport of organic molecules across the tonoplast[J].Advances in Botanical Research,1997,25(8):365-400.
[19]Meyer D,Pajonk S,Micali C,et al.Extracellular transport and integration of plant secretory proteins into pathogeninduced cell wall compartments[J].Plant Journal,2009,57(6):986.
[20]刘天行,郭佳,王伟,等.小米中结合型酚类化合物的分离与鉴定[J].南京农业大学学报,2014,37(1):138-142.
[21]姚增玉.山杏种皮黑色素提取及其性质研究[D].杨凌:西北农林科技大学,2007.
[22]王巧娥,唐安斌,石碧,等.脂溶性茶多酚的合成及其抗油脂自动氧化特性的研究[J].天然产物研究与开发,2001,13(4):12-15.
[23]卢婉容,潘迪,陈佳薇,等.超声辅助提取木瓜皮中结合酚的工艺研究[J].食品工业,2015(8):86-90.
[24]Chiremba C,Rooney L W,Beta T.Microwave-assisted extraction of bound phenolic acids in bran and flour fractions from sorghum and maize cultivars varying in hardness[J].Journal of Agricultural&Food Chemistry,2012,60(18):4735-4742.
[25]Wang Y K,Zhang X,Chen G L,et al.Antioxidant property and their free,soluble conjugate and insoluble-bound phenolic contents in selected beans[J].Journal of Functional Foods,2016,24:359-372.
[26]Pajak P,Socha R,Galkowska D,et al.Phenolic profile and antioxidant activity in selected seeds and sprouts[J].Food Chemistry,2014,143(1):300-306.
[27]易谷洋.碳纳米管固相萃取——高效液相色谱法测定水中酚类化合物[D].上海:东华大学,2012.
[28]严守雷,王清章,彭光华,等.莲藕多酚浸提工艺研究[J].食品研究与开发,2006,27(4):55-58.
[29]张力平,孙长霞,李俊清,等.植物多酚的研究现状及发展前景[J].林业科学,2005,41(6):157-162.
[30]刘晔,沈娜娜,刘大川.菜籽蛋白和酚的固-液相平衡[J].中国油脂,2015,40(8):17-21.
[31]Arranz S,Calixto F S.Analysis of polyphenols in cereals may be improved performing acidic hydrolysis:a study in wheat flour and wheat bran and cereals of the diet[J].Journal of Cereal Science,2010,51(3):313-318.
[32]徐菲,杨希娟,党斌,等.酸法提取青稞麸皮结合酚工艺优化[J].农业工程学报,2016,32(17):301-308.
[33]Sani I M,Iqbal S,Chan K W,et al.Effect of acid and base catalyzed hydrolysis on the yield of phenolics and antioxidant activity of extracts from germinated brown rice(GBR)[J].Molecules,2012,17(6):7584-7594.
[34]Su D,Zhang R,Hou F.Comparison of the free and bound phenolic profiles and cellular antioxidant activities of litchi pulp extracts from different solvents[J].BMC Complementary and Alternative Medicine,2014,14(1):1-10.
[35]Bonoli M,Verardo V,Marconi E,et al.Antioxidant phenols in barley(Hordeum vulgare L.)flour:comparative spectrophotometric study among extraction methods of free and bound phenolic compounds[J].Journal of Agricultural&Food Chemistry,2004,52(16):5195-5200.
[36]Alves G H,Ferreira C D,Vivian P G,et al.The revisited levels of free and bound phenolics in rice:effects of the extraction procedure[J].Food Chemistry,2016,208:116.
[37]Yingjian Lu D L.Influence of postharvest storage,processing,and extraction methods on the analysis of phenolic phytochemicals[J].Acs Symposium,2014,1185:3-31.
[38]Strack D,Heilemann J,Klinkott E S,et al.Cell wall-bound phenolics from norway spruce(Picea abies)needles[J].Zeitschrift Für Naturforschung C,2014,43(1-2):37-41.
[39]Huynh N T,Smagghe G,Gonzales G B,et al.Enzymeassisted extraction enhancing the phenolic release from cauliflower(Brassica oleracea L.var.botrytis)outer leaves[J].Journal of Agricultural&Food Chemistry,2014,62(30):7468-7476.
[40]Lekha P K,Lonsane B K.Production and application of tannin acyl hydrolase:state of the art[J].Advances in Applied Microbiology,1997,44(27):215-260.
[41]Garciaconesa M T,Ostergaard P,Kauppinen S,et al.Hydrolysis of diethyl diferulates by a tannase fromAspergillus oryzae[J].Carbohydrate Polymers,2001,44(4):319-324.
[42]Xu E,Wu Z,Long J,et al.Improved bioaccessibility of phenolics and antioxidant activity of glutinous rice and its fermented Chinese rice wine by simultaneous extrusion and enzymatic hydrolysis[J].Journal of Functional Foods,2015(17):214-226.
[43]Tasse L,Bercovici J,Pizzutserin S,et al.Functional metagenomics to mine the human gut microbiome for dietary fiber catabolic enzymes[J].Genome Research,2010,20(11):1605-1612.
[44]Zhang C,Monk J M,Lu J T,et al.Cooked navy and black bean diets improve biomarkers of colon health and reduce inflammation during colitis[J].British Journal of Nutrition,2014,111(9):1549-1563.
[45]Campbell K A,Glatz C E,Johnson L A,et al.Advances in aqueous extraction processing of soybeans[J].Journal of the American Oil Chemists'Society,2011,88(4):449-465.
[46]Lohani U C,Muthukumarappan K.Application of pulsed electric field to release bound phenolics in sorghum flour and apple pomace[J].Innovative Food Science&Emerging Technologies,2016,35:29-35.
[47]Liu R H.Whole grain phytochemicals and health[J].Journal of Cereal Science,2007,46(3):207-219.
[48]Siah S D,Konczak I,Agboola S,et al.In vitro investigations of the potential health benefits of Australian-grown faba beans(Vicia faba L.):chemopreventative capacity and inhibitory effects on the angiotensin-converting enzyme,glucosidase and lipase[J].British Journal of Nutrition,2012,108(1):123-134.
[49]Tang Y,Zhang B,Li X,et al.Bound phenolics of quinoa seeds released by acid,alkaline and enzymatic treatments and their antioxidant andα-glucosidase and pancreatic lipase inhibitory effects[J].Journal of Agricultural&Food Chemistry,2016,64(8):1712.
[50]Maillard M N,Berset C.Evolution of antioxidant activity during kilning:role of insoluble bound phenolic acids of barley and malt[J].Journal of Agricultural&Food Chemistry,1995,43(7):1789-1793.
[51]符莎露,吴甜甜,吴春华,等.植物多酚的抗氧化和抗菌机理及其在食品中的应用[J].食品工业,2016(6):242-246.
[52]张金宏.苹果渣中游离酚和结合酚的提取及其功能特性的研究[D].杨凌:西北农林科技大学,2016.
[53]Oliveira M D S,Cipolatti E P,Furlong E B,et al.Phenolic compounds and antioxidant activity in fermented rice(Oryza sativa)bran[J].Ciência E Tecnologia De Alimentos,2012,32(3):531-537.
[54]Ou S,Kwok K C.Ferulic acid:pharmaceutical functions,preparation and applications in foods[J].Journal of the Science of Food and Agriculture,2004,84(11):1261-1269.
[55]Akan K,Tihan D,Duman U,et al.Comparison of surgical Limberg flap technique and crystallized phenol application in the treatment of pilonidal sinus disease:a retrospective study[J].Turkish Journal of Surgery,2014,29(4):162-166.
[56]Rupasinghe H P V,Wang L,Huber G M,et al.Effect of baking on dietary fibre and phenolics of muffins incorporated with apple skin powder[J].Food Chemistry,2008,107(3):1217-1224.
[57]Agil R,Hosseinian F.Dual functionality of triticale as a novel dietary source of prebiotics with antioxidant activity in fermented dairy products[J].Plant Foods for Human Nutrition,2012,67(1):88-93.
[58]Qi S,Zhou D.Lotus seed epicarp extract as potential antioxidant and anti-obesity additive in Chinese Cantonese Sausage[J].Meat Science,2013,93(2):257-262.
[2]Lee J,Chan B L,Mitchell A E.Identification/quantification of free and bound phenolic acids in peel and pulp of apples(Malus domestica)using high resolution mass spectrometry(HRMS)[J].Food Chemistry,2017,215:301-310.
[3]Chandrasekara A,Shahidi F.Content of insoluble bound phenolics in millets and their contribution to antioxidant capacity[J].Journal of Agricultural&Food Chemistry,2010,58(11):6706-6714.
[4]Chen G L,Zhang X,Chen S G,et al.Antioxidant activities and contents of free,esterified and insoluble-bound phenolics in 14subtropical fruit leaves collected from the south of China[J].Journal of Functional Foods,2017,30:290-302.
[5]原田,刘邻渭,高忠梅,等.石榴皮游离与结合态多酚的组成和抗氧化性研究[J].食品工业科技,2014,35(18):161-166.
[6]Wukitch S J,Boivin R L,Bonoli P T,et al.Investigation of performance limiting phenomena in a variable phase ICRF antenna in Alcator C-Mod[J].Plasma Physics&Controlled Fusion,2004,46(9):1479-1491.
[7]Holtekjolen A K,Kinitz C,Knutsen S H.Flavanol and bound phenolic acid contents in different barley varieties[J].Journal of Agricultural&Food Chemistry,2006,54(6):2253-2260.
[8]Y F,Sun J,Wu X,et al.Antioxidant and antiproliferative activities of common vegetables[J].Journal of Agricultural&Food Chemistry,2002,50(25):7449-7454.
[9]Fu-Hua L I,Guo X H,Xia C Y,et al.Research advance in antioxidant activity of phenolic compounds in whole grains[J].Food Science,2012,33(13):299-304.
[10]Carrete M,Gil-Sánchez J M.Analysis of nonextractable phenolic compounds in foods:the current state of the art[J].Journal of Agricultural&Food Chemistry,2011,59(24):12713-12724.
[11]Vaher M,Matso K,Levandi T,et al.Phenolic compounds and the antioxidant activity of the bran,flour and whole grain of different wheat varieties[J].Procedia Chemistry,2010,2(1):76-82.
[12]王兰.黄淮麦区小麦主栽品种酚酸含量分析及磨粉对酚酸含量的影响[D].北京:中国农业科学院,2011.
[13]Ayoub M,Camargo A C D,Shahidi F.Antioxidants and bioactivities of free,esterified and insoluble-bound phenolics from berry seed meals[J].Food Chemistry,2016,197:221-232.
[14]Wang B N,Liu H F,Zheng J B,et al.Distribution of phenolic acids in different tissues of jujube and their antioxidant activity[J].Journal of Agricultural&Food Chemistry,2011,59(4):1288-1292.
[15]Camargo A C D,Gallo C R,Shahidi F.Gamma-irradiation induced changes in microbiological status,phenolic profile and antioxidant activity of peanut skin[J].Journal of Functional Foods,2015,(12):129-143.
[16]Kim I H,Chun H S.Composition of fatty acid and phenolic acid in rice with the different milling fractions[J].Journal of the Korean Society of Food Science&Nutrition,1996,10(4):350-357.
[17]Albishi T,John J A,Al-Khalifa A S,et al.Antioxidative phenolic constituents of skins of onion varieties and their activities[J].Journal of Functional Foods,2013,5(3):1191-1203.
[18]Martinoia E,Ratajczak R.Transport of organic molecules across the tonoplast[J].Advances in Botanical Research,1997,25(8):365-400.
[19]Meyer D,Pajonk S,Micali C,et al.Extracellular transport and integration of plant secretory proteins into pathogeninduced cell wall compartments[J].Plant Journal,2009,57(6):986.
[20]刘天行,郭佳,王伟,等.小米中结合型酚类化合物的分离与鉴定[J].南京农业大学学报,2014,37(1):138-142.
[21]姚增玉.山杏种皮黑色素提取及其性质研究[D].杨凌:西北农林科技大学,2007.
[22]王巧娥,唐安斌,石碧,等.脂溶性茶多酚的合成及其抗油脂自动氧化特性的研究[J].天然产物研究与开发,2001,13(4):12-15.
[23]卢婉容,潘迪,陈佳薇,等.超声辅助提取木瓜皮中结合酚的工艺研究[J].食品工业,2015(8):86-90.
[24]Chiremba C,Rooney L W,Beta T.Microwave-assisted extraction of bound phenolic acids in bran and flour fractions from sorghum and maize cultivars varying in hardness[J].Journal of Agricultural&Food Chemistry,2012,60(18):4735-4742.
[25]Wang Y K,Zhang X,Chen G L,et al.Antioxidant property and their free,soluble conjugate and insoluble-bound phenolic contents in selected beans[J].Journal of Functional Foods,2016,24:359-372.
[26]Pajak P,Socha R,Galkowska D,et al.Phenolic profile and antioxidant activity in selected seeds and sprouts[J].Food Chemistry,2014,143(1):300-306.
[27]易谷洋.碳纳米管固相萃取——高效液相色谱法测定水中酚类化合物[D].上海:东华大学,2012.
[28]严守雷,王清章,彭光华,等.莲藕多酚浸提工艺研究[J].食品研究与开发,2006,27(4):55-58.
[29]张力平,孙长霞,李俊清,等.植物多酚的研究现状及发展前景[J].林业科学,2005,41(6):157-162.
[30]刘晔,沈娜娜,刘大川.菜籽蛋白和酚的固-液相平衡[J].中国油脂,2015,40(8):17-21.
[31]Arranz S,Calixto F S.Analysis of polyphenols in cereals may be improved performing acidic hydrolysis:a study in wheat flour and wheat bran and cereals of the diet[J].Journal of Cereal Science,2010,51(3):313-318.
[32]徐菲,杨希娟,党斌,等.酸法提取青稞麸皮结合酚工艺优化[J].农业工程学报,2016,32(17):301-308.
[33]Sani I M,Iqbal S,Chan K W,et al.Effect of acid and base catalyzed hydrolysis on the yield of phenolics and antioxidant activity of extracts from germinated brown rice(GBR)[J].Molecules,2012,17(6):7584-7594.
[34]Su D,Zhang R,Hou F.Comparison of the free and bound phenolic profiles and cellular antioxidant activities of litchi pulp extracts from different solvents[J].BMC Complementary and Alternative Medicine,2014,14(1):1-10.
[35]Bonoli M,Verardo V,Marconi E,et al.Antioxidant phenols in barley(Hordeum vulgare L.)flour:comparative spectrophotometric study among extraction methods of free and bound phenolic compounds[J].Journal of Agricultural&Food Chemistry,2004,52(16):5195-5200.
[36]Alves G H,Ferreira C D,Vivian P G,et al.The revisited levels of free and bound phenolics in rice:effects of the extraction procedure[J].Food Chemistry,2016,208:116.
[37]Yingjian Lu D L.Influence of postharvest storage,processing,and extraction methods on the analysis of phenolic phytochemicals[J].Acs Symposium,2014,1185:3-31.
[38]Strack D,Heilemann J,Klinkott E S,et al.Cell wall-bound phenolics from norway spruce(Picea abies)needles[J].Zeitschrift Für Naturforschung C,2014,43(1-2):37-41.
[39]Huynh N T,Smagghe G,Gonzales G B,et al.Enzymeassisted extraction enhancing the phenolic release from cauliflower(Brassica oleracea L.var.botrytis)outer leaves[J].Journal of Agricultural&Food Chemistry,2014,62(30):7468-7476.
[40]Lekha P K,Lonsane B K.Production and application of tannin acyl hydrolase:state of the art[J].Advances in Applied Microbiology,1997,44(27):215-260.
[41]Garciaconesa M T,Ostergaard P,Kauppinen S,et al.Hydrolysis of diethyl diferulates by a tannase fromAspergillus oryzae[J].Carbohydrate Polymers,2001,44(4):319-324.
[42]Xu E,Wu Z,Long J,et al.Improved bioaccessibility of phenolics and antioxidant activity of glutinous rice and its fermented Chinese rice wine by simultaneous extrusion and enzymatic hydrolysis[J].Journal of Functional Foods,2015(17):214-226.
[43]Tasse L,Bercovici J,Pizzutserin S,et al.Functional metagenomics to mine the human gut microbiome for dietary fiber catabolic enzymes[J].Genome Research,2010,20(11):1605-1612.
[44]Zhang C,Monk J M,Lu J T,et al.Cooked navy and black bean diets improve biomarkers of colon health and reduce inflammation during colitis[J].British Journal of Nutrition,2014,111(9):1549-1563.
[45]Campbell K A,Glatz C E,Johnson L A,et al.Advances in aqueous extraction processing of soybeans[J].Journal of the American Oil Chemists'Society,2011,88(4):449-465.
[46]Lohani U C,Muthukumarappan K.Application of pulsed electric field to release bound phenolics in sorghum flour and apple pomace[J].Innovative Food Science&Emerging Technologies,2016,35:29-35.
[47]Liu R H.Whole grain phytochemicals and health[J].Journal of Cereal Science,2007,46(3):207-219.
[48]Siah S D,Konczak I,Agboola S,et al.In vitro investigations of the potential health benefits of Australian-grown faba beans(Vicia faba L.):chemopreventative capacity and inhibitory effects on the angiotensin-converting enzyme,glucosidase and lipase[J].British Journal of Nutrition,2012,108(1):123-134.
[49]Tang Y,Zhang B,Li X,et al.Bound phenolics of quinoa seeds released by acid,alkaline and enzymatic treatments and their antioxidant andα-glucosidase and pancreatic lipase inhibitory effects[J].Journal of Agricultural&Food Chemistry,2016,64(8):1712.
[50]Maillard M N,Berset C.Evolution of antioxidant activity during kilning:role of insoluble bound phenolic acids of barley and malt[J].Journal of Agricultural&Food Chemistry,1995,43(7):1789-1793.
[51]符莎露,吴甜甜,吴春华,等.植物多酚的抗氧化和抗菌机理及其在食品中的应用[J].食品工业,2016(6):242-246.
[52]张金宏.苹果渣中游离酚和结合酚的提取及其功能特性的研究[D].杨凌:西北农林科技大学,2016.
[53]Oliveira M D S,Cipolatti E P,Furlong E B,et al.Phenolic compounds and antioxidant activity in fermented rice(Oryza sativa)bran[J].Ciência E Tecnologia De Alimentos,2012,32(3):531-537.
[54]Ou S,Kwok K C.Ferulic acid:pharmaceutical functions,preparation and applications in foods[J].Journal of the Science of Food and Agriculture,2004,84(11):1261-1269.
[55]Akan K,Tihan D,Duman U,et al.Comparison of surgical Limberg flap technique and crystallized phenol application in the treatment of pilonidal sinus disease:a retrospective study[J].Turkish Journal of Surgery,2014,29(4):162-166.
[56]Rupasinghe H P V,Wang L,Huber G M,et al.Effect of baking on dietary fibre and phenolics of muffins incorporated with apple skin powder[J].Food Chemistry,2008,107(3):1217-1224.
[57]Agil R,Hosseinian F.Dual functionality of triticale as a novel dietary source of prebiotics with antioxidant activity in fermented dairy products[J].Plant Foods for Human Nutrition,2012,67(1):88-93.
[58]Qi S,Zhou D.Lotus seed epicarp extract as potential antioxidant and anti-obesity additive in Chinese Cantonese Sausage[J].Meat Science,2013,93(2):257-262.