食品中多酚类化合物种类、提取方法和检测技术研究进展
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摘要
食品中的多酚类化合物种类丰富,是天然的抗氧化剂和重要的功能因子。对食品中的多酚类化合物进行有效地提取和检测,有助于更全面地研究食品中多酚类化合物的种类和含量,能够更好地解析食品对人体的保健功能。因此,近年来受到国内外学者的广泛关注。文中对食品中多酚类化合物的种类结构、提取工艺和检测手段进行综述,旨在为食品中多酚类化合物的研究提供指导,为含多酚类化合物的功能性食品开发提供新思路。
There are various polyphenols in food products that are natural antioxidants and important functional factors. Effective extraction and detection of polyphenols are beneficial for studying the species and contents of polyphenols in foods, which leads to better analysis of healthy effects of foods on human body. Therefore, it has become a subject of great interest for many researchers around the world in recent years. In this paper, recent studies on species and structures, extraction technologies, and detection methods of polyphenols in foods were reviewed. It aimed to provide guidance for researching polyphenols in foods, and offering new ideas for developing polyphenol-rich functional foods.
There are various polyphenols in food products that are natural antioxidants and important functional factors. Effective extraction and detection of polyphenols are beneficial for studying the species and contents of polyphenols in foods, which leads to better analysis of healthy effects of foods on human body. Therefore, it has become a subject of great interest for many researchers around the world in recent years. In this paper, recent studies on species and structures, extraction technologies, and detection methods of polyphenols in foods were reviewed. It aimed to provide guidance for researching polyphenols in foods, and offering new ideas for developing polyphenol-rich functional foods.
引文
[1]SINGH B,SINGH J P,KAUR A,et al.Phenolic composition and antioxidant potential of grain legume seeds:a review[J].Food Research International,2017,101:1-16.
[2]MANDAL S M,CHAKRABORTY D,DEY S.Phenolic acids act as signaling molecules in plant-microbe symbioses[J].Plant Signaling and Behavior,2010,5(4):359-368.
[3]GANESAN K,XU B.Polyphenol-rich dry common beans(Phaseolus vulgaris L.)and their health benefits[J].International Journal of Molecular Sciences,2017,18(11):2 331-2 357.
[4]AWIKA J M,DUODU K G.Bioactive polyphenols and peptides in cowpea(Vigna unguiculata)and their health promoting properties:a review[J].Journal of Functional Foods,2016,38:686-697.
[5]ESTEBAN-FERNNDEZ A,ZORRAQUN-PEA I,LLA-NO D G D,et al.The role of wine and food polyphenols in oral health[J].Trends in Food Science and Technology,2017,69:118-130.
[6]DOMNGUEZ-RODRGUEZ G,MARINA M L,PLAZA M.Strategies for the extraction and analysis of non-extractable polyphenols from plants[J].Journal of Chromatography A,2017,1514:1-15.
[7]PAPUC C,GORAN G V,PREDESCU C N,et al.Plant polyphenols as antioxidant and antibacterial agents for shelf-life extension of meat and meat products:classification,structures,sources,and action mechanisms[J].Comprehensive Reviews in Food Science and Food Safety,2017,16(6):1 243-1 268.
[8]ROMAGNOLO D F,SELMIN O I.Flavonoids and cancer prevention:a review of the evidence[J].Journal of Nutrition in Gerontology and Geriatrics,2012,31(3):206-238.
[9]武小芬,苏小军,陈亮.木质素结构分析方法研究进展[J].可再生能源,2015,33(2):267-274.
[10]LI D,LI B,MA Y,et al.Polyphenols,anthocyanins,and flavonoids contents and the antioxidant capacity of various cultivars of highbush and half-high blueberries[J].Journal of Food Composition and Analysis,2017,62:84-93.
[11]C'UJI C'N,AVIKIN K,JANKOVI C'T,et al.Optimization of polyphenols extraction from dried chokeberry using maceration as traditional technique[J].Food Chemistry,2016,194:135-142.
[12]SHAO Y,HU Z,YU Y,et al.Phenolic acids,anthocyanins,proanthocyanidins,antioxidant activity,minerals and their correlations in non-pigmented,red,and black rice[J].Food Chemistry,2018,239:733-741.
[13]李晓英,薛梅,樊汶樵.蓝莓花、茎、叶酚类物质含量及抗氧化活性比较[J].食品科学,2017,38(3):142-147.
[14]CHEN H,ZHOU Y,SHAO Y,et al.Free phenolic acids in Shanxi aged vinegar:changes during aging and synergistic antioxidant activities[J].International Journal of Food Properties,2016,19(6):1 183-1 193.
[15]ESPADABELLIDO E,FERREIROGONZáLEZ M,CAR-RERA C,et al.Optimization of the ultrasound-assisted extraction of anthocyanins and total phenolic compounds in mulberry(Morus nigra)pulp[J].Food Chemistry,2017,219:23-32.
[16]WANG Z,Li T,LIU F,et al.Effects of ultrasonic treatment on the maturation of Zhenjiang vinegar[J].Ultrasonics Sonochemistry,2017,39:272-280.
[17]WANG C,ZUO Y.Ultrasound-assisted hydrolysis and gas chromatography-mass spectrometric determination of phenolic compounds in cranberry products[J].Food Chemistry,2011,128(2):562-568.
[18]申远,张清安,易璇,等.超声波处理对红葡萄酒总酚、总黄酮含量及自由基清除活性的影响[J].食品工业科技,2015,36(23):111-115.
[19]ZHANG Q A,WANG T T.Effect of ultrasound irradiation on the evolution of color properties and major phenolic compounds in wine during storage[J].Food Chemistry,2017,234:372-380.
[20]CASTRO-LPEZ C,VENTURA-SOBREVILLA J M,GONZLEZ-HERNNDEZ M D,et al.Impact of extraction techniques on antioxidant capacities and phytochemical composition of polyphenol-rich extracts[J].Food Chemistry,2017,237:1 139-1 148.
[21]PINGRET D,FABIANO-TIXIER A,CHEMAT F.Degradation during application of ultrasound in food processing:a review[J].Food Control,2013,31(2):593-606.
[22]KHANDPUR P,GOGATE P R.Effect of novel ultrasound based processing on the nutrition quality of different fruit and vegetable juices[J].Ultrasonics Sonochemistry,2015,27:125-136.
[23]CAMEL V.Microwave-assisted solvent extraction of environmental samples[J].Trends in Analytical Chemistry,2000,19(4):229-248.
[24]MOREIRA M M,BARROSO M F,BOEYKENS A,et al.Valorization of apple tree wood residues by polyphenols extraction:comparison between conventional and microwave-assisted extraction[J].Industrial Crops and Products,2017,104:210-220.
[25]LI Y,LI S,LIN S J,et al.Microwave-assisted extraction of natural antioxidants from the exotic Gordonia axillaris fruit:optimization and identification of phenolic compounds[J].Molecules,2017,22(9):1 481-1 497.
[26]LI H,DENG Z,WU T,et al.Microwave-assisted extraction of phenolics with maximal antioxidant activities in tomatoes[J].Food Chemistry,2012,130(4):928-936.
[27]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 and Food Chemistry,2012,60(18):4 735-4 742.
[28]钟平,王频频.正交试验优化微波提取厚朴皮总酚工艺[J].食品科学,2013,34(8):82-84.
[29]FRANCISCO M,VELASCO P,MORENO D A,et al.Cooking methods of Brassica rapa affect the preservation of glucosinolates,phenolics and vitamin C[J].Food Research International,2010,43(5):1 455-1 463.
[30]AREND G D,ADORNO W T,REZZADORI K,et al.Concentration of phenolic compounds from strawberry(Fragaria X ananassa Duch)juice by nanofiltration membrane[J].Journal of Food Engineering,2017,201:36-41.
[31]NATOLINO A,PORTO C D,RODRGUEZ-ROJO S,et al.Supercritical antisolvent precipitation of polyphenols from grape marc extract[J].Journal of Supercritical Fluids,2016,118:54-63.
[32]GARCIA-MENDOZA M D P,ESPINOSA-PARDO F A,BASEGGIO A M,et al.Extraction of phenolic compounds and anthocyanins from ju9ara(Euterpe edulis Mart.)residues using pressurized liquids and supercritical fluids[J].Journal of Supercritical Fluids,2017,119:9-16.
[33]王振宇,孔子浩,郑舒婷,等.天然结合酚的研究进展[J].中国调味品,2017(11):143-148.
[34]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,2016,208:116-123.
[35]ACOSTA-ESTRADA B A,GUTIRREZ-URIBE J A,SERNA-SALDVAR S O.Bound phenolics in foods,a review[J].Food Chemistry,2014,152(6):46-55.
[36]FU M,XU Y,CHEN Y,et al.Evaluation of bioactive flavonoids and antioxidant activity in pericarpium citri reticulatae(Citrus reticulata‘Chachi’)during storage[J].Food Chemistry,2017,230:649-656.
[37]CHINEDUM E,SANNI S,THERESSA N,et al.Effect of domestic cooking on the starch digestibility,predicted glycemic indices,polyphenol contents and alpha amylase inhibitory properties of beans(Phaseolis vulgaris)and breadfruit(Treculia africana)[J].International Journal of Biological Macromolecules,2017,106:200-206.
[38]OZTURK I,CALISKAN O,TORNUK F,et al.Antioxidant,antimicrobial,mineral,volatile,physicochemical and microbiological characteristics of traditional homemade Turkish vinegars[J].LWT-Food Science and Technology,2015,63(1):144-151.
[39]GIORDANO D,LOCATELLI M,TRAVAGLIA F,et al.Bioactive compound and antioxidant activity distribution in roller-milled and pearled fractions of conventional and pigmented wheat varieties[J].Food Chemistry,2017,233:483-491.
[40]CHEN C,WANG L,WANG R,et al.Phenolic contents,cellular antioxidant activity and antiproliferative capacity of different varieties of oats[J].Food Chemistry,2018,239:260-267.
[41]CHOU C H,LIU C W,YANG D J,et al.Amino acid,mineral,and polyphenolic profiles of black vinegar,and its lipid lowering and antioxidant effects in vivo[J].Food Chemistry,2015,168:63-69.
[42]WANG C,ZUO Y.Ultrasound-assisted hydrolysis and gas chromatography-mass spectrometric determination of phenolic compounds in cranberry products[J].Food Chemistry,2011,128(2):562-568.
[43]MARSOLVALL A,BALCELLS M,ERAS J,et al.Injection-port derivatization coupled to GC-MS/MS for the analysis of glycosylated and non-glycosylated polyphenols in fruit samples[J].Food Chemistry,2016,204:210-217.
[44]PLESSI M,BERTELLI D,MIGLIETTA F.Extraction and identification by GC-MS of phenolic acids in traditional balsamic vinegar from Modena[J].Journal of Food Composition and Analysis,2006,19(1):49-54.
[45]ILAROVP,CESLOVL,MELOUN M.Fast gradient HPLC/MS separation of phenolics in green tea to monitor their degradation[J].Food Chemistry,2017,237:471-480.
[46]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.
[47]CENDROWSKI A,S'CIBISZ I,KIELISZEK M,et al.UP-LC-PDA-Q/TOF-MS profile of polyphenolic compounds of liqueurs from rose petals(Rosa rugosa)[J].Molecules,2017,22(11):1 832-1 846.
[48]TIAN Y,LIIMATAINEN J,ALANNE A L,et al.Phenolic compounds extracted by acidic aqueous ethanol from berries and leaves of different berry plants[J].Food Chemistry,2017,220:266-281.
[49]邹文钊.萃取电喷雾电离质谱检测技术研究[D].合肥:中国科学技术大学,2017.
[50]柯牡芳,韩京,朱腾高,等.牛油果中化学成分的内部萃取电喷雾电离质谱检测[J].高等学校化学学报,2017,38(5):738-742.
[2]MANDAL S M,CHAKRABORTY D,DEY S.Phenolic acids act as signaling molecules in plant-microbe symbioses[J].Plant Signaling and Behavior,2010,5(4):359-368.
[3]GANESAN K,XU B.Polyphenol-rich dry common beans(Phaseolus vulgaris L.)and their health benefits[J].International Journal of Molecular Sciences,2017,18(11):2 331-2 357.
[4]AWIKA J M,DUODU K G.Bioactive polyphenols and peptides in cowpea(Vigna unguiculata)and their health promoting properties:a review[J].Journal of Functional Foods,2016,38:686-697.
[5]ESTEBAN-FERNNDEZ A,ZORRAQUN-PEA I,LLA-NO D G D,et al.The role of wine and food polyphenols in oral health[J].Trends in Food Science and Technology,2017,69:118-130.
[6]DOMNGUEZ-RODRGUEZ G,MARINA M L,PLAZA M.Strategies for the extraction and analysis of non-extractable polyphenols from plants[J].Journal of Chromatography A,2017,1514:1-15.
[7]PAPUC C,GORAN G V,PREDESCU C N,et al.Plant polyphenols as antioxidant and antibacterial agents for shelf-life extension of meat and meat products:classification,structures,sources,and action mechanisms[J].Comprehensive Reviews in Food Science and Food Safety,2017,16(6):1 243-1 268.
[8]ROMAGNOLO D F,SELMIN O I.Flavonoids and cancer prevention:a review of the evidence[J].Journal of Nutrition in Gerontology and Geriatrics,2012,31(3):206-238.
[9]武小芬,苏小军,陈亮.木质素结构分析方法研究进展[J].可再生能源,2015,33(2):267-274.
[10]LI D,LI B,MA Y,et al.Polyphenols,anthocyanins,and flavonoids contents and the antioxidant capacity of various cultivars of highbush and half-high blueberries[J].Journal of Food Composition and Analysis,2017,62:84-93.
[11]C'UJI C'N,AVIKIN K,JANKOVI C'T,et al.Optimization of polyphenols extraction from dried chokeberry using maceration as traditional technique[J].Food Chemistry,2016,194:135-142.
[12]SHAO Y,HU Z,YU Y,et al.Phenolic acids,anthocyanins,proanthocyanidins,antioxidant activity,minerals and their correlations in non-pigmented,red,and black rice[J].Food Chemistry,2018,239:733-741.
[13]李晓英,薛梅,樊汶樵.蓝莓花、茎、叶酚类物质含量及抗氧化活性比较[J].食品科学,2017,38(3):142-147.
[14]CHEN H,ZHOU Y,SHAO Y,et al.Free phenolic acids in Shanxi aged vinegar:changes during aging and synergistic antioxidant activities[J].International Journal of Food Properties,2016,19(6):1 183-1 193.
[15]ESPADABELLIDO E,FERREIROGONZáLEZ M,CAR-RERA C,et al.Optimization of the ultrasound-assisted extraction of anthocyanins and total phenolic compounds in mulberry(Morus nigra)pulp[J].Food Chemistry,2017,219:23-32.
[16]WANG Z,Li T,LIU F,et al.Effects of ultrasonic treatment on the maturation of Zhenjiang vinegar[J].Ultrasonics Sonochemistry,2017,39:272-280.
[17]WANG C,ZUO Y.Ultrasound-assisted hydrolysis and gas chromatography-mass spectrometric determination of phenolic compounds in cranberry products[J].Food Chemistry,2011,128(2):562-568.
[18]申远,张清安,易璇,等.超声波处理对红葡萄酒总酚、总黄酮含量及自由基清除活性的影响[J].食品工业科技,2015,36(23):111-115.
[19]ZHANG Q A,WANG T T.Effect of ultrasound irradiation on the evolution of color properties and major phenolic compounds in wine during storage[J].Food Chemistry,2017,234:372-380.
[20]CASTRO-LPEZ C,VENTURA-SOBREVILLA J M,GONZLEZ-HERNNDEZ M D,et al.Impact of extraction techniques on antioxidant capacities and phytochemical composition of polyphenol-rich extracts[J].Food Chemistry,2017,237:1 139-1 148.
[21]PINGRET D,FABIANO-TIXIER A,CHEMAT F.Degradation during application of ultrasound in food processing:a review[J].Food Control,2013,31(2):593-606.
[22]KHANDPUR P,GOGATE P R.Effect of novel ultrasound based processing on the nutrition quality of different fruit and vegetable juices[J].Ultrasonics Sonochemistry,2015,27:125-136.
[23]CAMEL V.Microwave-assisted solvent extraction of environmental samples[J].Trends in Analytical Chemistry,2000,19(4):229-248.
[24]MOREIRA M M,BARROSO M F,BOEYKENS A,et al.Valorization of apple tree wood residues by polyphenols extraction:comparison between conventional and microwave-assisted extraction[J].Industrial Crops and Products,2017,104:210-220.
[25]LI Y,LI S,LIN S J,et al.Microwave-assisted extraction of natural antioxidants from the exotic Gordonia axillaris fruit:optimization and identification of phenolic compounds[J].Molecules,2017,22(9):1 481-1 497.
[26]LI H,DENG Z,WU T,et al.Microwave-assisted extraction of phenolics with maximal antioxidant activities in tomatoes[J].Food Chemistry,2012,130(4):928-936.
[27]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 and Food Chemistry,2012,60(18):4 735-4 742.
[28]钟平,王频频.正交试验优化微波提取厚朴皮总酚工艺[J].食品科学,2013,34(8):82-84.
[29]FRANCISCO M,VELASCO P,MORENO D A,et al.Cooking methods of Brassica rapa affect the preservation of glucosinolates,phenolics and vitamin C[J].Food Research International,2010,43(5):1 455-1 463.
[30]AREND G D,ADORNO W T,REZZADORI K,et al.Concentration of phenolic compounds from strawberry(Fragaria X ananassa Duch)juice by nanofiltration membrane[J].Journal of Food Engineering,2017,201:36-41.
[31]NATOLINO A,PORTO C D,RODRGUEZ-ROJO S,et al.Supercritical antisolvent precipitation of polyphenols from grape marc extract[J].Journal of Supercritical Fluids,2016,118:54-63.
[32]GARCIA-MENDOZA M D P,ESPINOSA-PARDO F A,BASEGGIO A M,et al.Extraction of phenolic compounds and anthocyanins from ju9ara(Euterpe edulis Mart.)residues using pressurized liquids and supercritical fluids[J].Journal of Supercritical Fluids,2017,119:9-16.
[33]王振宇,孔子浩,郑舒婷,等.天然结合酚的研究进展[J].中国调味品,2017(11):143-148.
[34]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,2016,208:116-123.
[35]ACOSTA-ESTRADA B A,GUTIRREZ-URIBE J A,SERNA-SALDVAR S O.Bound phenolics in foods,a review[J].Food Chemistry,2014,152(6):46-55.
[36]FU M,XU Y,CHEN Y,et al.Evaluation of bioactive flavonoids and antioxidant activity in pericarpium citri reticulatae(Citrus reticulata‘Chachi’)during storage[J].Food Chemistry,2017,230:649-656.
[37]CHINEDUM E,SANNI S,THERESSA N,et al.Effect of domestic cooking on the starch digestibility,predicted glycemic indices,polyphenol contents and alpha amylase inhibitory properties of beans(Phaseolis vulgaris)and breadfruit(Treculia africana)[J].International Journal of Biological Macromolecules,2017,106:200-206.
[38]OZTURK I,CALISKAN O,TORNUK F,et al.Antioxidant,antimicrobial,mineral,volatile,physicochemical and microbiological characteristics of traditional homemade Turkish vinegars[J].LWT-Food Science and Technology,2015,63(1):144-151.
[39]GIORDANO D,LOCATELLI M,TRAVAGLIA F,et al.Bioactive compound and antioxidant activity distribution in roller-milled and pearled fractions of conventional and pigmented wheat varieties[J].Food Chemistry,2017,233:483-491.
[40]CHEN C,WANG L,WANG R,et al.Phenolic contents,cellular antioxidant activity and antiproliferative capacity of different varieties of oats[J].Food Chemistry,2018,239:260-267.
[41]CHOU C H,LIU C W,YANG D J,et al.Amino acid,mineral,and polyphenolic profiles of black vinegar,and its lipid lowering and antioxidant effects in vivo[J].Food Chemistry,2015,168:63-69.
[42]WANG C,ZUO Y.Ultrasound-assisted hydrolysis and gas chromatography-mass spectrometric determination of phenolic compounds in cranberry products[J].Food Chemistry,2011,128(2):562-568.
[43]MARSOLVALL A,BALCELLS M,ERAS J,et al.Injection-port derivatization coupled to GC-MS/MS for the analysis of glycosylated and non-glycosylated polyphenols in fruit samples[J].Food Chemistry,2016,204:210-217.
[44]PLESSI M,BERTELLI D,MIGLIETTA F.Extraction and identification by GC-MS of phenolic acids in traditional balsamic vinegar from Modena[J].Journal of Food Composition and Analysis,2006,19(1):49-54.
[45]ILAROVP,CESLOVL,MELOUN M.Fast gradient HPLC/MS separation of phenolics in green tea to monitor their degradation[J].Food Chemistry,2017,237:471-480.
[46]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.
[47]CENDROWSKI A,S'CIBISZ I,KIELISZEK M,et al.UP-LC-PDA-Q/TOF-MS profile of polyphenolic compounds of liqueurs from rose petals(Rosa rugosa)[J].Molecules,2017,22(11):1 832-1 846.
[48]TIAN Y,LIIMATAINEN J,ALANNE A L,et al.Phenolic compounds extracted by acidic aqueous ethanol from berries and leaves of different berry plants[J].Food Chemistry,2017,220:266-281.
[49]邹文钊.萃取电喷雾电离质谱检测技术研究[D].合肥:中国科学技术大学,2017.
[50]柯牡芳,韩京,朱腾高,等.牛油果中化学成分的内部萃取电喷雾电离质谱检测[J].高等学校化学学报,2017,38(5):738-742.