5种梅干菜的酚类化合物及抗氧化能力比较分析
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摘要
以市售5种梅干菜为研究对象,测定梅干菜酚类化合物的含量,用高效液相色谱-串联质谱(high performance liquid chromatography-tandem mass spectrometry,HPLC-MS/MS)法鉴定梅干菜酚类化合物的种类,并用4种抗氧化能力评价方法评价梅干菜。结果表明,市售5种梅干菜所含的酚类化合物含量和各酚类化合物所占的比例及其抗氧化能力差异显著。其中咕咕鲜牌梅干菜(GGX)的总酚含量为14.18 mg GAE/g,总黄酮含量为7.10 mg RE/g,2,2’-联氮-双-(3-乙基苯并噻唑啉-6-磺酸)二铵盐(2,2’-azino-bis(3-ethylbenzthiazoline-6-sulphonate),ABTS)法、铁离子还原(ferric reducing antioxidant power,FRAP)法、1,1-二苯基-2-三硝基苯肼法和氧自由基吸收能力(oxygen radical absorbance capacity,ORAC)法测得的抗氧化能力分别为28.09、32.88、31.72μmol TE/g和445.55μmol TE/g,显著高于其他4种梅干菜。其次,利用HPLC-MS/MS法分析鉴定出梅干菜中共含有17种酚类化合物,包括9种类黄酮和8种酚酸。其中,梅干菜中的类黄酮主要有野漆树苷、山柰酚、异鼠李素、柚皮素等;酚酸主要有阿魏酸、香豆酸和肉桂酸等。此外,4种抗氧化能力评价方法中,ABTS与FRAP相关性最高,相关系数为0.967;ORAC法测得的梅干菜抗氧化能力显著高于其他3种方法;而ABTS法与梅干菜的抗氧化剂相关性最高,最适合评价梅干菜的总抗氧化能力。综上所述,不同种类市售梅干菜的酚类化合物含量和抗氧化能力均不同,其中,GGX总酚含量最高、抗氧化能力最强。
In this study, the contents of phenolic compounds in five commercial brands of pickled and dried mustard were analyzed by high performance liquid chromatography-tandem mass spectrometry(HPLC-MS/MS),and their antioxidant activity was evaluated by four antioxidant capacity assays.The five brands were Xianhong(XH),Guguxian(GGX),Guanhuawang(GHW),and homemade products A and B(JTA and JTB).The results showed that the total phenol contents,the proportions of different phenolic classes and antioxidant activity were significantly different among five pickled and dried mustard brands.The total phenol content of GGX was 14.18 mg GAE/g, the total flavonoid content was 7.10 mg RE/g,and the antioxidant activity was 28.09, 31.72, 32.88 and 445.55 μmol TE/g as measured by 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonate(ABTS),1,1-diphenyl-2-picrylhydrazyl(DPPH) radical scavenging,ferric reducing antioxidant power(FRAP),and oxygen radical absorbance capacity(ORAC) assays, respectively, which was significantly higher than that of the other four brands. A total of 17 phenolic compounds, including 9 flavonoids and 8 phenolic acids, were identified by HPLC-MS/MS.Among these,the major flavonoids were identified as rhoifolin,kaempferol,isorhamnetin,and naringenin,ferulic acid,p-coumaric acid and t-cinnamic acid were the main phenolic acids.In addition,among the four antioxidant capacity assays,the correlation between ABTS and FRAP was the highest with a correlation coefficient of 0.967; the antioxidant capacity of pickled and dried mustard evaluated by the ORAC method was significantly higher than those by three other methods; the ABTS method exhibited the highest correlation coefficient with antioxidants, which was the most suitable for evaluating the total antioxidant capacity of pickled and dried mustard.In summary,the total phenol contents and antioxidant capacities of different brands of commercially available pickled and dried mustard were different.Among them,GGX had the highest total phenol content and strongest antioxidant capacity.
In this study, the contents of phenolic compounds in five commercial brands of pickled and dried mustard were analyzed by high performance liquid chromatography-tandem mass spectrometry(HPLC-MS/MS),and their antioxidant activity was evaluated by four antioxidant capacity assays.The five brands were Xianhong(XH),Guguxian(GGX),Guanhuawang(GHW),and homemade products A and B(JTA and JTB).The results showed that the total phenol contents,the proportions of different phenolic classes and antioxidant activity were significantly different among five pickled and dried mustard brands.The total phenol content of GGX was 14.18 mg GAE/g, the total flavonoid content was 7.10 mg RE/g,and the antioxidant activity was 28.09, 31.72, 32.88 and 445.55 μmol TE/g as measured by 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonate(ABTS),1,1-diphenyl-2-picrylhydrazyl(DPPH) radical scavenging,ferric reducing antioxidant power(FRAP),and oxygen radical absorbance capacity(ORAC) assays, respectively, which was significantly higher than that of the other four brands. A total of 17 phenolic compounds, including 9 flavonoids and 8 phenolic acids, were identified by HPLC-MS/MS.Among these,the major flavonoids were identified as rhoifolin,kaempferol,isorhamnetin,and naringenin,ferulic acid,p-coumaric acid and t-cinnamic acid were the main phenolic acids.In addition,among the four antioxidant capacity assays,the correlation between ABTS and FRAP was the highest with a correlation coefficient of 0.967; the antioxidant capacity of pickled and dried mustard evaluated by the ORAC method was significantly higher than those by three other methods; the ABTS method exhibited the highest correlation coefficient with antioxidants, which was the most suitable for evaluating the total antioxidant capacity of pickled and dried mustard.In summary,the total phenol contents and antioxidant capacities of different brands of commercially available pickled and dried mustard were different.Among them,GGX had the highest total phenol content and strongest antioxidant capacity.
引文
[1]LI C,TANG Z F,HUANG M,et al.Antioxidant efficacy of extracts produced from pickled and dried mustard in rapeseed and peanut oils[J].Journal of Food Science,2012,77(4):C394-C400.DOI:10.1111/j.1750-3841.2011.02606.x.
[2]HUANG S R,HUANG M,FENG B.Antioxidant activity of extracts produced from pickled and dried mustard(Brassica juncea Coss.var.foliosa Bailey)[J].International Journal of Food Properties,2012,15(1/2):374-384.DOI:10.1080/10942912.2010.487628.
[3]黄师荣,唐忠锋,李庆斌.梅干菜提取物抑菌作用的研究[J].食品工业科技,2009,30(8):106-107.DOI:10.13386/j.issn1002-0306.2009.08.074.
[4]王超,汪江英,时磊,等.九头芥梅干菜提取物的抗氧化性能研究[J].食品与机械,2013,29(3):116-119.DOI:10.3969/j.issn.1003-5788.2013.03.028.
[5]黄师荣,李豪杰,戴杰辉,等.九头芥梅干菜提取物抗菌活性及其在猪肉保鲜中的应用[J].现代食品科技,2014,30(10):58-62.DOI:10.13982/j.mfst.1673-9078.2014.10.011.
[6]黄师荣,唐忠锋.梅干菜提取物保鲜草莓的研究[J].安徽农业科学,2009,37(26):12695-12696.DOI:10.13989/j.cnki.0517-6611.2009.26.026.
[7]BAO J S,CAI Y Z,SUN M,et al.Anthocyanins,flavonols,and free radical scavenging activity of Chinese bayberry(Myrica rubra)extracts and their color properties and stability[J].Journal of Agricultural and Food Chemistry,2005,53(6):2327-2332.DOI:10.1021/jf048312z.
[8] JIA Z S, TANG M, WU J. The determination of flavonoid contents in mulberry and their scavenging effects on superoxide radicals[J].Food Chemistry,1999,64(4):555-559.DOI:10.1016/S0308-8146(98)00102-2.
[9]KIM D O,JEONG S W,CHANG Y L.Antioxidant capacity of phenolic phytochemicals from various cultivars of plums[J].Food Chemistry,2003,81(3):321-326.DOI:10.1016/S0308-8146(02)00423-5.
[10]THIES W. Complex-formation between glucosinolates and tetrachloropalladate(II)and its utilization in plant-breeding[J].Fette Seifen Anstrichmittel,1982,84(9):338-342.DOI:10.1002/lipi.19820840903.
[11]HUANG H Z,SUN Y J,LOU S T,et al.In vitro digestion combined with cellular assay to determine the antioxidant activity in Chinese bayberry(Myrica rubra Sieb.et Zucc.)fruits:a comparison with traditional methods[J].Food Chemistry,2014,146:363-370.DOI:10.1016/j.foodchem.2013.09.071.
[12]AMEER K,SHAHBAZ H M,KWON J H.Green extraction methods for polyphenols from plant matrices and their byproducts:a review[J].Comprehensive Reviews in Food Science and Food Safety,2017,16(2):295-315.DOI:10.1111/1541-4337.12253.
[13]王萍,朱祝军.不同采收季节对叶用芥菜类黄酮物质含量和抗氧化活性的影响[J].园艺学报,2006,33(4):745-750.DOI:10.3321/j.issn:0513-353X.2006.04.010.
[14]PARK S Y,JANG H L,LEE J H,et al.Changes in the phenolic compounds and antioxidant activities of mustard leaf(Brassica juncea)kimchi extracts during different fermentation periods[J].Food Science&Biotechnology,2017,26(1):105-112.DOI:10.1007/s10068-017-0014-5.
[15]徐专红.梅干菜肉的制作和贮藏性能初探[J].食品工业科技,1996(6):64-65.DOI:10.13386/j.issn1002-0306.1996.06.022.
[16]KORUS A,SLUPSKI J,GEBCZYNSKI P,et al.Effect of preliminary processing and method of preservation on the content of glucosinolates in kale(Brassica oleracea L.var.acephala)leaves[J].LWT-Food Science and Technology,2014,59(2):1003-1008.DOI:10.1016/j.lwt.2014.06.030.
[17]MITHEN R F,DEKKER M,VERKERK R,et al.The nutritional significance,biosynthesis and bioavailability of glucosinolates in human foods[J]. Journal of the Science of Food &Agriculture,2000,80(7):967-984.DOI:10.1002/(SICI)1097-0010(20000515)80:7<967::AID-JSFA597>3.0.CO;2-V.
[18]NUGRAHEDI P Y,VERKERK R,WIDIANARKO B,et al.A mechanistic perspective on process-induced changes in glucosinolate content in Brassica vegetables:a review[J].Critical Reviews in Food Science and Nutrition,2015,55(6):823-838.DOI:10.1080/10408398.2012.688076.
[19]宋亚,李凯利,方佳宁,等.鲜切紫甘蓝中花青苷和硫代葡萄糖苷在贮藏过程中的变化[J].食品科学,2016,37(18):96-101.DOI:10.7506/spkx1002-6630-201618016.
[20]AGUILO-AGUAYO I,SUAREZ M,PLAZA L,et al.Optimization of pulsed electric field pre-treatments to enhance health-promoting glucosinolates in broccoli flowers and stalk[J]. Journal of the Science of Food and Agriculture,2015,95(9):1868-1875.DOI:10.1002/jsfa.6891.
[21]SONG L,THORNALLEY P J.Effect of storage,processing and cooking on glucosinolate content of Brassica vegetables[J].Food&Chemical Toxicology,2007,45(2):216-224.DOI:10.1016/j.fct.2006.07.021.
[22]RUDI DE V H,BLIJLEVEN W G.The effect of processing conditions on glucosinolates in cruciferous vegetables[J].European Food Research and Technology,1988,187(6):525-529.DOI:10.1007/BF01042383.
[23]涂宗财,郭逍遥,刘成梅,等.芥菜中硫代葡萄糖苷提取工艺条件的优化[J].食品与生物技术学报,2007,26(6):9-12.DOI:10.3321/j.issn:1673-1689.2007.06.003.
[24]BANERJEE A,VARIYAR P S,CHATTERJEE S,et al.Effect of post harvest radiation processing and storage on the volatile oil composition and glucosinolate profile of cabbage[J]. Food Chemistry, 2014, 151: 22-30.DOI:10.1016/j.foodchem.2013.11.055.
[25]FRANCO P,SPINOZZI S,PAGNOTTA E,et al.Development of a liquid chromatography-electrospray ionization-tandem mass spectrometry method for the simultaneous analysis of intact glucosinolates and isothiocyanates in Brassicaceae seeds and functional foods[J].Journal of Chromatography A,2016,1428:154-161.DOI:10.1016/j.chroma.2015.09.001.
[26]CARTEA M E,FRANCISCO M,SOENGAS P,et al.Phenolic compounds in Brassica vegetables[J].Molecules,2011,16(1):251-280.DOI:10.3390/molecules16010251.
[27]胡玉霞.雪里蕻腌渍过程中理化成分及其抗氧化性变化研究[D].杭州:浙江大学,2007.
[28]LOPEZ-ALARCON C,DENICOLA A.Evaluating the antioxidant capacity of natural products:a review on chemical and cellular-based assays[J].Analytica Chimica Acta,2013,763:1-10.DOI:10.1016/j.aca.2012.11.051.
[29]PINCHUK I,SHOVAL H,DOTAN Y,et al.Evaluation of antioxidants:scope,limitations and relevance of assays[J].Chemistry and Physics of Lipids,2012,165(6):638-647.DOI:10.1016/j.chemphyslip.2012.05.003.
[30]王萍,朱祝军.腌制加工对不同品种叶用芥菜抗氧化物质含量和抗氧化活性的影响[J].核农学报,2006,20(6):516-520.DOI:10.3969/j.issn.1000-8551.2006.06.017.
[31]TODOROVIC V,REDOVNIKOVIC I R,TODOROVIC Z,et al.Polyphenols,methylxanthines,and antioxidant capacity of chocolates produced in Serbia[J].Journal of Food Composition and Analysis,2015,41:137-143.DOI:10.1016/j.jfca.2015.01.018.
[32]BAHORUN T,LUXIMON-RAMMA A,CROZIER A,et al.Total phenol, flavonoid, proanthocyanidin and vitamin C levels and antioxidant activities of Mauritian vegetables[J].Journal of the Science of Food&Agriculture,2004,84(12):1553-1561.DOI:10.1002/jsfa.1820.
[33]GONZALEZ E M,ANCOS D B,CANO P M.Relation between bioactive compounds and free radical-scavenging capacity in berry fruits during frozen storage[J].Journal of the Science of Food&Agriculture,2003,83(7):722-726.DOI:10.1002/jsfa.1359.
[34]THAIPONG K,BOONPRAKOB U,CROSBY K,et al.Comparison of ABTS,DPPH,FRAP,and ORAC assays for estimating antioxidant activity from guava fruit extracts[J].Journal of Food Composition&Analysis,2006,19(7):669-675.DOI:10.1016/j.jfca.2006.01.003.
[35]FLOEGEL A,KIM D O,CHUNG S J,et al.Comparison of ABTS/DPPH assays to measure antioxidant capacity in popular antioxidantrich US foods[J].Journal of Food Composition&Analysis,2011,24(7):1043-1048.DOI:10.1016/j.jfca.2011.01.008.
[2]HUANG S R,HUANG M,FENG B.Antioxidant activity of extracts produced from pickled and dried mustard(Brassica juncea Coss.var.foliosa Bailey)[J].International Journal of Food Properties,2012,15(1/2):374-384.DOI:10.1080/10942912.2010.487628.
[3]黄师荣,唐忠锋,李庆斌.梅干菜提取物抑菌作用的研究[J].食品工业科技,2009,30(8):106-107.DOI:10.13386/j.issn1002-0306.2009.08.074.
[4]王超,汪江英,时磊,等.九头芥梅干菜提取物的抗氧化性能研究[J].食品与机械,2013,29(3):116-119.DOI:10.3969/j.issn.1003-5788.2013.03.028.
[5]黄师荣,李豪杰,戴杰辉,等.九头芥梅干菜提取物抗菌活性及其在猪肉保鲜中的应用[J].现代食品科技,2014,30(10):58-62.DOI:10.13982/j.mfst.1673-9078.2014.10.011.
[6]黄师荣,唐忠锋.梅干菜提取物保鲜草莓的研究[J].安徽农业科学,2009,37(26):12695-12696.DOI:10.13989/j.cnki.0517-6611.2009.26.026.
[7]BAO J S,CAI Y Z,SUN M,et al.Anthocyanins,flavonols,and free radical scavenging activity of Chinese bayberry(Myrica rubra)extracts and their color properties and stability[J].Journal of Agricultural and Food Chemistry,2005,53(6):2327-2332.DOI:10.1021/jf048312z.
[8] JIA Z S, TANG M, WU J. The determination of flavonoid contents in mulberry and their scavenging effects on superoxide radicals[J].Food Chemistry,1999,64(4):555-559.DOI:10.1016/S0308-8146(98)00102-2.
[9]KIM D O,JEONG S W,CHANG Y L.Antioxidant capacity of phenolic phytochemicals from various cultivars of plums[J].Food Chemistry,2003,81(3):321-326.DOI:10.1016/S0308-8146(02)00423-5.
[10]THIES W. Complex-formation between glucosinolates and tetrachloropalladate(II)and its utilization in plant-breeding[J].Fette Seifen Anstrichmittel,1982,84(9):338-342.DOI:10.1002/lipi.19820840903.
[11]HUANG H Z,SUN Y J,LOU S T,et al.In vitro digestion combined with cellular assay to determine the antioxidant activity in Chinese bayberry(Myrica rubra Sieb.et Zucc.)fruits:a comparison with traditional methods[J].Food Chemistry,2014,146:363-370.DOI:10.1016/j.foodchem.2013.09.071.
[12]AMEER K,SHAHBAZ H M,KWON J H.Green extraction methods for polyphenols from plant matrices and their byproducts:a review[J].Comprehensive Reviews in Food Science and Food Safety,2017,16(2):295-315.DOI:10.1111/1541-4337.12253.
[13]王萍,朱祝军.不同采收季节对叶用芥菜类黄酮物质含量和抗氧化活性的影响[J].园艺学报,2006,33(4):745-750.DOI:10.3321/j.issn:0513-353X.2006.04.010.
[14]PARK S Y,JANG H L,LEE J H,et al.Changes in the phenolic compounds and antioxidant activities of mustard leaf(Brassica juncea)kimchi extracts during different fermentation periods[J].Food Science&Biotechnology,2017,26(1):105-112.DOI:10.1007/s10068-017-0014-5.
[15]徐专红.梅干菜肉的制作和贮藏性能初探[J].食品工业科技,1996(6):64-65.DOI:10.13386/j.issn1002-0306.1996.06.022.
[16]KORUS A,SLUPSKI J,GEBCZYNSKI P,et al.Effect of preliminary processing and method of preservation on the content of glucosinolates in kale(Brassica oleracea L.var.acephala)leaves[J].LWT-Food Science and Technology,2014,59(2):1003-1008.DOI:10.1016/j.lwt.2014.06.030.
[17]MITHEN R F,DEKKER M,VERKERK R,et al.The nutritional significance,biosynthesis and bioavailability of glucosinolates in human foods[J]. Journal of the Science of Food &Agriculture,2000,80(7):967-984.DOI:10.1002/(SICI)1097-0010(20000515)80:7<967::AID-JSFA597>3.0.CO;2-V.
[18]NUGRAHEDI P Y,VERKERK R,WIDIANARKO B,et al.A mechanistic perspective on process-induced changes in glucosinolate content in Brassica vegetables:a review[J].Critical Reviews in Food Science and Nutrition,2015,55(6):823-838.DOI:10.1080/10408398.2012.688076.
[19]宋亚,李凯利,方佳宁,等.鲜切紫甘蓝中花青苷和硫代葡萄糖苷在贮藏过程中的变化[J].食品科学,2016,37(18):96-101.DOI:10.7506/spkx1002-6630-201618016.
[20]AGUILO-AGUAYO I,SUAREZ M,PLAZA L,et al.Optimization of pulsed electric field pre-treatments to enhance health-promoting glucosinolates in broccoli flowers and stalk[J]. Journal of the Science of Food and Agriculture,2015,95(9):1868-1875.DOI:10.1002/jsfa.6891.
[21]SONG L,THORNALLEY P J.Effect of storage,processing and cooking on glucosinolate content of Brassica vegetables[J].Food&Chemical Toxicology,2007,45(2):216-224.DOI:10.1016/j.fct.2006.07.021.
[22]RUDI DE V H,BLIJLEVEN W G.The effect of processing conditions on glucosinolates in cruciferous vegetables[J].European Food Research and Technology,1988,187(6):525-529.DOI:10.1007/BF01042383.
[23]涂宗财,郭逍遥,刘成梅,等.芥菜中硫代葡萄糖苷提取工艺条件的优化[J].食品与生物技术学报,2007,26(6):9-12.DOI:10.3321/j.issn:1673-1689.2007.06.003.
[24]BANERJEE A,VARIYAR P S,CHATTERJEE S,et al.Effect of post harvest radiation processing and storage on the volatile oil composition and glucosinolate profile of cabbage[J]. Food Chemistry, 2014, 151: 22-30.DOI:10.1016/j.foodchem.2013.11.055.
[25]FRANCO P,SPINOZZI S,PAGNOTTA E,et al.Development of a liquid chromatography-electrospray ionization-tandem mass spectrometry method for the simultaneous analysis of intact glucosinolates and isothiocyanates in Brassicaceae seeds and functional foods[J].Journal of Chromatography A,2016,1428:154-161.DOI:10.1016/j.chroma.2015.09.001.
[26]CARTEA M E,FRANCISCO M,SOENGAS P,et al.Phenolic compounds in Brassica vegetables[J].Molecules,2011,16(1):251-280.DOI:10.3390/molecules16010251.
[27]胡玉霞.雪里蕻腌渍过程中理化成分及其抗氧化性变化研究[D].杭州:浙江大学,2007.
[28]LOPEZ-ALARCON C,DENICOLA A.Evaluating the antioxidant capacity of natural products:a review on chemical and cellular-based assays[J].Analytica Chimica Acta,2013,763:1-10.DOI:10.1016/j.aca.2012.11.051.
[29]PINCHUK I,SHOVAL H,DOTAN Y,et al.Evaluation of antioxidants:scope,limitations and relevance of assays[J].Chemistry and Physics of Lipids,2012,165(6):638-647.DOI:10.1016/j.chemphyslip.2012.05.003.
[30]王萍,朱祝军.腌制加工对不同品种叶用芥菜抗氧化物质含量和抗氧化活性的影响[J].核农学报,2006,20(6):516-520.DOI:10.3969/j.issn.1000-8551.2006.06.017.
[31]TODOROVIC V,REDOVNIKOVIC I R,TODOROVIC Z,et al.Polyphenols,methylxanthines,and antioxidant capacity of chocolates produced in Serbia[J].Journal of Food Composition and Analysis,2015,41:137-143.DOI:10.1016/j.jfca.2015.01.018.
[32]BAHORUN T,LUXIMON-RAMMA A,CROZIER A,et al.Total phenol, flavonoid, proanthocyanidin and vitamin C levels and antioxidant activities of Mauritian vegetables[J].Journal of the Science of Food&Agriculture,2004,84(12):1553-1561.DOI:10.1002/jsfa.1820.
[33]GONZALEZ E M,ANCOS D B,CANO P M.Relation between bioactive compounds and free radical-scavenging capacity in berry fruits during frozen storage[J].Journal of the Science of Food&Agriculture,2003,83(7):722-726.DOI:10.1002/jsfa.1359.
[34]THAIPONG K,BOONPRAKOB U,CROSBY K,et al.Comparison of ABTS,DPPH,FRAP,and ORAC assays for estimating antioxidant activity from guava fruit extracts[J].Journal of Food Composition&Analysis,2006,19(7):669-675.DOI:10.1016/j.jfca.2006.01.003.
[35]FLOEGEL A,KIM D O,CHUNG S J,et al.Comparison of ABTS/DPPH assays to measure antioxidant capacity in popular antioxidantrich US foods[J].Journal of Food Composition&Analysis,2011,24(7):1043-1048.DOI:10.1016/j.jfca.2011.01.008.