啤酒花活性成分与抗氧化活性的相关性
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摘要
以3个品种的萨斯特啤酒花为原料,比较了其石油醚、氯仿、乙酸乙酯、正丁醇和水相等不同极性溶剂提取物中α-酸、β-酸、总黄酮和总多酚的含量,采用·OH、1,1-二苯基-2-三硝基苯肼自由基、β-胡萝卜素-亚油酸3种不同的抗氧化活性评价体系对各极性溶剂提取物的抗氧化活性进行了研究,并与其活性成分的含量进行了相关性分析。结果表明,啤酒花各极性部位均具有不同程度的抗氧化活性。α-酸、β-酸在石油醚相中含量较高,在3个啤酒花样品中的含量范围分别为α-酸444.29～583.81 mg/g、β-酸131.83～293.19 mg/g,在氯仿相中含量相对较低,其余提取物中均未检出;相关性研究表明α-酸、β-酸是石油醚和氯仿相抗氧化活性的主要物质基础。中等极性和极性较大溶剂提取物中啤酒花总黄酮、总多酚含量较高,相关性研究也表明黄酮、多酚类物质是这类提取物抗氧化活性的主要物质基础;其中,3个啤酒花样品中总黄酮、总多酚在乙酸乙酯相中含量最高,分别为20.43～24.13 mg/g和34.97～40.24 mg/g,正丁醇次之,分别为9.45～11.68 mg/g和12.12～19.14 mg/g。
Three varieties of SAST hops were extracted with solvents of different polarities including petroleum ether,chloroform, ethyl acetate, n-butanol and water. The contents of α-acids, β-acids, total ?avonoids and total polyphenols in these extracts were measured and compared. Their antioxidant activities were evaluated by hydroxyl radical scavenging,1,1-diphenyl-2-picrylhydrazyl(DPPH) radical scavenging and β-carotene-linoleic acid model system assays. The correlation was analyzed between the antioxidant activity and the contents of bioactive ingredients. The results showed that all parts of hops displayed antioxidant activity. α-Acids and β-acids were more abundant in the petroleum ether extracts, which ranged between 444.29-583.81 and 131.83-293.19 mg/g, respectively; however, lower values were detected in the chloroform extracts, and undetectable levels were found in other extracts. The correlation analysis suggested that α-acids and β-acids were the main antioxidant compounds in the petroleum ether and chloroform extracts. The medium and highly polar solvent extracts were rich in total flavonoids and total polyphenols, which were the main antioxidant compounds. For all three varieties, the highest contents of total ?avonoids(20.43-24.13 mg/g) and total polyphenols(34.97-40.24 mg/g) were in the ethyl acetate extracts followed by the n-butanol extracts(9.45-11.68 and 12.12-19.14 mg/g).
Three varieties of SAST hops were extracted with solvents of different polarities including petroleum ether,chloroform, ethyl acetate, n-butanol and water. The contents of α-acids, β-acids, total ?avonoids and total polyphenols in these extracts were measured and compared. Their antioxidant activities were evaluated by hydroxyl radical scavenging,1,1-diphenyl-2-picrylhydrazyl(DPPH) radical scavenging and β-carotene-linoleic acid model system assays. The correlation was analyzed between the antioxidant activity and the contents of bioactive ingredients. The results showed that all parts of hops displayed antioxidant activity. α-Acids and β-acids were more abundant in the petroleum ether extracts, which ranged between 444.29-583.81 and 131.83-293.19 mg/g, respectively; however, lower values were detected in the chloroform extracts, and undetectable levels were found in other extracts. The correlation analysis suggested that α-acids and β-acids were the main antioxidant compounds in the petroleum ether and chloroform extracts. The medium and highly polar solvent extracts were rich in total flavonoids and total polyphenols, which were the main antioxidant compounds. For all three varieties, the highest contents of total ?avonoids(20.43-24.13 mg/g) and total polyphenols(34.97-40.24 mg/g) were in the ethyl acetate extracts followed by the n-butanol extracts(9.45-11.68 and 12.12-19.14 mg/g).
引文
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[27]DE OLIVEIRA NETO J R,DE MACêDO I Y L,DE OLIVEIRA N RL,et al.Antioxidant capacity and total phenol content in hop and malt commercial samples[J].Electroanalysis,2017,29(12):2788-2792.DOI:10.1002/elan.201700492.
[28]张维库,王守宝,付骋宇,等.啤酒花的黄酮类成分[J].中国中药杂志,2013,38(10):1539-1542.DOI:10.4268/cjcmm20131017.
[29]刘莎.啤酒花多酚的纯化及抗氧化活性研究[D].乌鲁木齐:新疆大学,2015:1-11.
[30]任红,郑少杰,张小利,等.基于不同抗氧化机制的黄酮类化合物构效关系研究进展[J].食品工业科技,2016,37(2):384-388.DOI:10.13386/j.issn1002-0306.2016.02.070.
[31]LUCRECIA L C,MONICA A N.New method to determine antioxidant activity of polyphenols[J].Food Chemistry,2006,54(22):8397-8402.DOI:10.1021/jf061729f.
[32]吴丽君.天然药物化学[M].5版.北京:人民卫生出版社,2007:169-182.
[2]JIN S W,CHEN G L,DU J J M,et al.Antioxidant properties and principal phenolic compositions of Cynomorium Songaricum Rupr.[J].International Journal of Food Properties,2013,17(1):13-25.DOI:10.1080/10942912.2011.587623.
[3]方允中,郑荣梁.自由基生物学的理论与应用[M].北京:科学出版社,2002:634-661.
[4]章林,黄明,周光宏.天然抗氧化剂在肉制品中的应用研究进展[J].食品科学,2012,33(7):299-302.
[5]刘玉梅.啤酒花的化学成分及药理作用研究进展[J].食品科学,2009,30(23):521-527.
[6]李玉晶,刘玉梅.齐洛克啤酒花品种的挥发性成分分析[J].中国酿造,2017,36(4):168-173.DOI:10.11882/j.issn.0254-5071.2017.04.035.
[7]MICHAEL D,CHRISTIAN V T,ANDREAS D,et al.The bitter chemodiversity of hops(Humulus lupulus L.)[J].Journal of Agricultural and Food Chemistry,2016,64(41):7789-7799.DOI‰10.1021/acs.jafc.6b03933.
[8]李峰,刘玉梅.马格努门啤酒花挥发性成分的气相色谱-质谱联用分析[J].食品科学,2012,33(22):259-263.
[9]C A T H E R I N E L,G U I L L A U M E L,S O N I A C.M e a s u r i n g antioxidant efficiency of wort,malt,and hops against the 2,2-azobis(2-amidinopropane)dihydrochloride-induced oxidation of an aqueous dispersion of linoleic acid[J].Journal of Agricultural and Food Chemistry,2000,48(4):1129-1344.DOI‰10.1021/jf9911242.
[10]MICHAEL D,ANDREAS D,THOMAS H.Sensomics analysis of key bitter compounds in the hard resin of hops(Humulus lupulus L.)and their contribution to the bitter profile of pilsner-type beer[J].Journal of Agricultural and Food Chemistry,2015,63(13):3402-3418.DOI‰10.1021/acs.jafc.5b00239.
[11]国家质量监督检验检疫总局.啤酒花制品:GB/T 20369-2006[S].北京:标准出版社.2006:1-11.
[12]燕雪花,孙芸,刘宏炳,等.新疆紫穗槐中总黄酮的提取与含量测定[J].光谱实验室,2012,29(2):878-881.
[13]FERAH C O,MEHMET A,SATYAJIT D S.Comparative study of antioxidant properties and total phenolic content of the extracts of Humulus lupulus L.and quantification of bioactive components by LC-MS/MS and GC-MS[J].Joural of Agricultural and Food Chemistry,2013,61(44):10498-10506.DOI‰10.1021/jf4031508.
[14]DUAN X J,ZHANG W W,LI X M,et al.Evaluation of antioxidant property of extract and fractions obtained from a red alga,Polysiphonia urceolata[J].Food Chemistry,2006,95(1):37-43.DOI:10.1016/j.foodchem.2004.12.015.
[15]陈利梅,李德茂,李燕.万寿菊黄色素抗氧化特性研究[J].食品研究与开发,2009,30(12):26-29.
[16]KAEWPIBOON C,LIRDPRAPAMONGKOL K,SRISOMSAP C,et al.Studies of the in vitro cytotoxic,antioxidant,lipase inhibitory and antimicrobial activities of selected Thai medicinal plants[J].BMCComplementary and Alternative Medicine,2012,12(1):217-225.DOI‰10.1186/1472-6882-12-217.
[17]凌关庭.抗氧化食品与健康[M].北京:化学工业出版社,2004:333-334.
[18]张昊,任发政.羟基和超氧自由基的检测研究进展[J].光谱学与光谱分析,2009,29(4):1093-1098.DOI:10.3964/j.issn.1000-0593(2009)04-1093-07.
[19]白姗姗,刘博奥,刘玉梅,啤酒花废弃枝叶的营养成分及抗氧化活性研究[J].酿酒科技,2016(3):61-64.DOI:10.13746/j.njkj.2015446.
[20]BRAND-WILLIAMS W,CUVELIER M E,BERSET C.Use of a free radical method to evaluate antioxidant activity[J].LWT-Food science and Technology,1995,28(1):25-30.DOI:10.1016/s0023-6438(95)80008-5.
[21]刘莎,刘玉梅.啤酒花多酚提取物的抗氧化活性研究[J].酿酒科技,2010(10):19-22.DOI:10.13746/j.njkj.2010.10.029.
[22]刘玉梅.啤酒花的分析评价及六氢蛇麻酮类的合成与应用[D].无锡:江南大学,2007:49-50.
[23]LIU Yumei,GU Xiaohong,TANG Jian,et al,Antioxidant activities of hops(Humulus lupulus)and their products[J].Journal of the American Society of Brewing Chemists,2007,65(2):116-121.DOI:10.1094/ASBCJ-2007-0211-01.
[24]赵素华,司琴图亚.黑加仑、榅桲、无花果、桑椹和啤酒花苦味酸及制品抗氧化作用研究[J].食品科学,2002,23(2):35-37.
[25]TING P,LUSK L,REFLING J,et al.Identification of antiradical hop compounds[J].Journal of the American Society of Brewing Chemists,2008,66(2):116-126.DOI:10.1094/ASBCJ-2008-0310-01.
[26]MALIAR T,NEME?EK P,üRGEOVáE,et al,Secondary metabolites,antioxidant and anti-proteinase activities of methanolic extracts from cones of hop(Humulus lupulus L.)cultivars[J].Chemical Papers,2017,71:41-48.DOI:10.1007/s11696-016-0034-2.
[27]DE OLIVEIRA NETO J R,DE MACêDO I Y L,DE OLIVEIRA N RL,et al.Antioxidant capacity and total phenol content in hop and malt commercial samples[J].Electroanalysis,2017,29(12):2788-2792.DOI:10.1002/elan.201700492.
[28]张维库,王守宝,付骋宇,等.啤酒花的黄酮类成分[J].中国中药杂志,2013,38(10):1539-1542.DOI:10.4268/cjcmm20131017.
[29]刘莎.啤酒花多酚的纯化及抗氧化活性研究[D].乌鲁木齐:新疆大学,2015:1-11.
[30]任红,郑少杰,张小利,等.基于不同抗氧化机制的黄酮类化合物构效关系研究进展[J].食品工业科技,2016,37(2):384-388.DOI:10.13386/j.issn1002-0306.2016.02.070.
[31]LUCRECIA L C,MONICA A N.New method to determine antioxidant activity of polyphenols[J].Food Chemistry,2006,54(22):8397-8402.DOI:10.1021/jf061729f.
[32]吴丽君.天然药物化学[M].5版.北京:人民卫生出版社,2007:169-182.