白姑鱼和小黄鱼肉中挥发性风味物质的鉴定
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摘要
采用新型固相萃取整体捕集剂(Mono-Trap)结合气相色谱-质谱-嗅闻技术对白姑鱼和小黄鱼肉的挥发性风味物质进行鉴定,分别得到42种和49种挥发性成分。进一步通过芳香萃取物稀释分析法分别从白姑鱼和小黄鱼肉挥发物中筛选出12种和6种挥发物,其中9种挥发物经质谱和线性保留指数鉴定。进一步结合校准频率(modified frequency,MF)法,各筛选出2种鱼肉中排名前10的气味物质。白姑鱼中香气稀释(flavor dilution,FD)因子最高为40的化合物为三甲胺、2-辛烯-1-醇、壬醛及金属味未知化合物。结合MF排名,得到三甲胺和2-辛烯-1-醇对白姑鱼贡献较大;小黄鱼中FD因子最高为40的化合物为己醛和2-辛烯-1-醇,但结合MF排名,对其气味贡献较大的是三甲胺和未知烧烤味化合物。6-甲基-5-庚烯-2-酮为2种鱼中均鉴定出的一种带金属味或血腥味成分,根据MF排名,该化合物对白姑鱼影响更大。2,3-戊二酮、1-戊烯-3-醇为小黄鱼中MF较靠前的物质,结合三甲胺和未知烧烤味化合物以及白姑鱼中未鉴定到的二甲基二硫醚,这些挥发物可能是造成其与白姑鱼气味感知差异的原因。
Monolithic material sorptive extraction(MMSE) combined with gas chromatography-mass spectrometryolfatometry(GC-MS-O) was used to identify the key odor-active compounds of white croaker and small yellow croaker. A total of 42 and 49 volatiles were identified in white croaker and small yellow croaker, respectively. Out of these volatiles, 12 and 6 were selected respectively from the two fish by aroma extraction dilution analysis(AEDA), among which 9 volatiles were identified by comparison of their mass spectra and linear retention indices with published data. For each fish, the top 10 major odor-active compounds were screened out by the modified frequency(MF) method. The compounds with the highest FD value of 40 in white croaker were identified as trimethylamine, 2-octen-1-ol, nonanal, and an unknown compound that smelled like metal. According to MF ranking, trimethylamine and 2-octen-1-ol had greater contributions to the odor of white croaker. The odorants with the highest FD value of 40 in small yellow croaker were hexanal and 2-octen-1-ol, but trimethylamine and unknown compounds that smelled like barbecue had greater contributions to its odor according to MF ranking. 6-Methyl-5-heptane-2-one was another odorous compound that was present in each fish and responsible for their metallic or bloody odor. According to MF ranking, this compound had a greater effect on the odor of white croaker than on small yellow croaker. 2,3-Pentanedione and 1-penten-3-ol, ranked higher among the top 10 odor-active compounds in small yellow croaker, together with trimethylamin, unknown barbecue-like odorants and dimethyl disulfide which was not identified in white croaker may be one of the reasons for the difference in odor between the two fish.
Monolithic material sorptive extraction(MMSE) combined with gas chromatography-mass spectrometryolfatometry(GC-MS-O) was used to identify the key odor-active compounds of white croaker and small yellow croaker. A total of 42 and 49 volatiles were identified in white croaker and small yellow croaker, respectively. Out of these volatiles, 12 and 6 were selected respectively from the two fish by aroma extraction dilution analysis(AEDA), among which 9 volatiles were identified by comparison of their mass spectra and linear retention indices with published data. For each fish, the top 10 major odor-active compounds were screened out by the modified frequency(MF) method. The compounds with the highest FD value of 40 in white croaker were identified as trimethylamine, 2-octen-1-ol, nonanal, and an unknown compound that smelled like metal. According to MF ranking, trimethylamine and 2-octen-1-ol had greater contributions to the odor of white croaker. The odorants with the highest FD value of 40 in small yellow croaker were hexanal and 2-octen-1-ol, but trimethylamine and unknown compounds that smelled like barbecue had greater contributions to its odor according to MF ranking. 6-Methyl-5-heptane-2-one was another odorous compound that was present in each fish and responsible for their metallic or bloody odor. According to MF ranking, this compound had a greater effect on the odor of white croaker than on small yellow croaker. 2,3-Pentanedione and 1-penten-3-ol, ranked higher among the top 10 odor-active compounds in small yellow croaker, together with trimethylamin, unknown barbecue-like odorants and dimethyl disulfide which was not identified in white croaker may be one of the reasons for the difference in odor between the two fish.
引文
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[22]赵庆喜,薛长湖,徐杰,等.微波蒸馏-固相微萃取-气相色谱-质谱-嗅觉检测器联用分析鳙鱼鱼肉中的挥发性成分[J].色谱,2007,25(2):267-271.
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[26]徐永霞,刘滢,姜程程,等.电子鼻结合气质联用法分析大菱鲆冷藏过程中挥发性成分变化[J].食品与发酵工业,2014,40(1):193-197.DOI:10.13995/j.cnki.11-1802/ts.2014.01.005.
[27]KAWAI T.Fish flavor[J].Critical Reviews in Food Science&Nutrition,1996,36:257-298.
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[29]IGLESIAS J,MEDINA I.Solid-phase micro-extraction method for the determination of volatile compounds associated to oxidation of fish muscle[J].Journal of Chromatography A,2008,1192(1):9-16.DOI:10.1016/j.chroma.2008.03.028.
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[31]贡慧,杨震,刘梦,等.秋刀鱼热加工后挥发性风味成分变化的分析[J].肉类研究,2017,31(1):25-31.DOI:10.7506/rlyj1001-8123-201701005.
[32]HEIEH R J,KINSELLA J E.Oxidation of polyunsaturated fatty acids:mechanisms,products,and inhibition with emphasis on fish[J].Advances in Food&Nutrition Research,1989,33:233-341.DOI:10.1016/s1043-4526(08)60129-1.
[33]冯晓群,韩玲,蒋玉梅,等.甘肃马鹿背最长肌挥发性物质的组成分析[J].甘肃农业大学学报,2008,43(6):159-162.DOI:10.13432/j.cnki.jgsau.2008.06.028.
[34]王璐,王锡昌,刘源.养殖场采样及市售草鱼肉气味成分的比较[J].食品工业科技,2010,31(5):76-80.DOI:10.13386/j.issn1002-0306.2010.05.071.
[35]HAYES K P,BURCH M D.Odorous compounds associated with algal blooms in south australian waters[J].Water Research,1989,23(1):115-121.DOI:10.1016/0043-1354(89)90069-9.
[36]CHA Y J,CADWALLADER K R,BAEJ H H.Volatile flavor components in snow crab cooker effluent and effluent concentrate[J].Journal of Food Science,1993,58(3):525-530.DOI:10.1111/j.1365-2621.1993.tb04316.x.
[37]夏明明,邵晨,刘源.虎纹蛙肌肉挥发性成分和脂肪酸分析[J].食品科学,2011,32(6):217-220.
[38]GIRARD B,DURANCE T.Headspace volatiles of sockeye and pink salmon as affected by retort process[J].Journal of Food Science,2010,65(1):34-39.DOI:10.1111/j.1365-2621.2000.tb15952.x.
[39]章超桦,平野敏行,铃木健,等.鲫的挥发性成分[J].水产学报,2000,24(4):354-358.
[40]ROCHAT S,EGGER J,CHAINTREAU A.Strategy for the identification of key odorants:application to shrimp aroma[J].Journal of Chromatography A,2009,1216(36):6424-6432.DOI:10.1016/j.chroma.2009.07.014.
[41]KARAHADIAN C,LINDSAY R C.Evaluation of compounds contributing characterizing fishy flavors in fish oils[J].Journal of the American Oil Chemists’Society,1989,66(7):953-960.DOI:10.1007/bf02682616.
[42]QUIRóS RBD,LóPEZ-HERNáNDEZ J,GONZáLEZ-CASTRO M,et al.Comparison of volatile components in fresh and canned sea urchin(Paracentrotus lividus,Lamarck)gonads by GC-MS using dynamic headspace sampling and microwave desorption[J].European Food Research&Technology,2001,212(6):643-647.DOI:10.1007/s002170100315.
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[2]吕金磊.中国近海石首鱼科鱼类DNA条形码及分子系统学研究[D].暨南大学,2017:2-5.
[3]MOLYNEUX R J,SCHIEBERLE P.Compound identification:a journal of agricultural and food chemistry perspective[J].Journal of Agricultural and Food Chemistry,2007,55(12):4625-4629.
[4]SATO A,SOTOMARU K,TAKEDA M.A novel approach for aroma components analysis using a monolithic hybrid adsorbent as a new generation medium.“MonoTrap”[EB/OL].(2011-04-25)[2013-08-21].http://www.atasgl.com/monotrap/poster_monotrap_ISEO2009.pdf.
[5]ZHANG H,WANG W,WANG H,etal.Effect of E-beam irradiation and microwave heating on the fatty acid composition and volatile compound profile of grass carp surim[J].Radiation Physics and Chemistry,2017,130:431-441.DOI:10.1016/j.radphyschem.2016.10.007.
[6]SAELEAW T,BENJAKUL S,GOKOGLU N,et al.Changes in lipids and fishy odour development in skin from Nile tilapia(Oreochromis niloticus)stored in ice[J].Food Chemistry,2013,141(3):2466-2472.DOI:10.1016/j.foodchem.2013.05.049.
[7]JOSEPHSON D B,LINDSAY R C,STUIBER D A.Volatile compounds characterizing the aroma of fresh atlantic and pacific oysters[J].Journal of Food Science,1987,50(1):5-9.DOI:10.1111/j.1365-2621.1985.tb13265.x.
[8]吉思茹.蒸制中华绒螯蟹关键性气味物质的鉴定研究[D].上海:上海海洋大学,2016:16-17.
[9]顾赛麒,吴娜,张晶晶,等.MMSE-GC-O结合OAV法鉴定蒸制崇明地区中华绒螯蟹中关键气味物质[J].食品安全质量检测学报,2014,5(3):879-881.
[10]张青.淡水鱼鱼肉中气味活性物质的鉴定[D].上海:上海海洋大学,2008:24-25.
[11]刘登勇,周光宏,徐幸莲.确定食品关键风味化合物的一种新方法:ROAV法[J].食品科学,2008,29(7):370-374.
[12]李贞子,杨具田,祁高展,等.兰州大尾羊肉挥发性风味组分研究[J].食品与机械,2016,32(12):50-54.DOI:10.13652/j.issn.1003-5788.2016.12.011.
[13]翁丽萍.养殖大黄鱼和野生大黄鱼风味的研究[D].杭州:浙江工商大学,2011:65-71.
[14]田迪英,焦慧,陶崴,等.5种海鱼挥发性风味成分分析[J].食品与发酵工业,2015,41(10):155-159.DOI:10.13995/j.cnki.11-1802/ts.201510029.
[15]里奥·范海默特.化合物香味阈值汇编[M].北京:科学出版社,2015.
[16]GROSCH W.Detection of potent odorants in foods by aroma extract dilution analysis[J].Trends in Food Science&Technology,1993,4(3):68-73.DOI:10.1016/0924-2244(93)90187-f.
[17]刘建彬,刘梦娅,何聪聪,等.应用AEDA结合OAV值计算鉴定可可液中关键气味活性化合物[J].食品与发酵工业,2013,39(9):180-184.DOI:10.13995/j.cnki.11-1802/ts.2013.09.041.
[18]杨欣怡,刘源,许长华,等.水产品中挥发性风味物质提取和分析研究进展[J].食品科学,2015,36(5):289-295.DOI:10.7506/spkx1002-6630-201505051.
[19]TOLDRA F,FLORES M.The role of muscle proteases and lipases in flavor development during the processing of dry-cured ham[J].Critical Reviews in Food Science,1998,38(4):331-352.DOI:10.1080/10408699891274237.
[20]刘敬科.鲢鱼风味特征及热历史对鲢鱼风味的影响[D].武汉:华中农业大学,2009:64-65.
[21]TOLDRA F.Proteolysis and lipolysis in flavour development of dry-cured meat products[J].Meat Science,1998,49:101-110.DOI:10.1016/s0309-1740(98)90041-9.
[22]赵庆喜,薛长湖,徐杰,等.微波蒸馏-固相微萃取-气相色谱-质谱-嗅觉检测器联用分析鳙鱼鱼肉中的挥发性成分[J].色谱,2007,25(2):267-271.
[23]PIVETEAU F,LE G S,GANDEMER G,et al.Aroma of fresh oysters Crassostrea gigas:composition and aroma notes[J].Journal of Agricultural&Food Chemistry,2000,48(10):4851-4854.DOI:10.1021/jf991394k.
[24]SIEK T J,ALBIN I A,SATHER L A,et al.Comparison of flavor thresholds of aliphatic lactones with those of fatty acids,esters,aldehydes,alcohols,and ketones[1]and[2][J].Journal of Dairy Science,1971,54(1):1-4.DOI:10.3168/jds.s0022-0302(71)85770-3.
[25]CHUNG H Y,YUNG I K S,MA W C J,et al.Analysis of volatile components in frozen and dried scallops(Patinopecten yessoensis)by gas chromatography-mass spectrometry[J].Food Research International,2002,35(1):43-53.DOI:10.1016/s0963-9969(01)00107-7.
[26]徐永霞,刘滢,姜程程,等.电子鼻结合气质联用法分析大菱鲆冷藏过程中挥发性成分变化[J].食品与发酵工业,2014,40(1):193-197.DOI:10.13995/j.cnki.11-1802/ts.2014.01.005.
[27]KAWAI T.Fish flavor[J].Critical Reviews in Food Science&Nutrition,1996,36:257-298.
[28]JOSEPHSON D B,LINDSAY R C.Enzymic generation of volatile aroma compounds from fresh fish[J].ACS Symposium SeriesAmerican Chemical Society,1986,30:201-219.DOI:10.1021/bk-1986-0317.ch017.
[29]IGLESIAS J,MEDINA I.Solid-phase micro-extraction method for the determination of volatile compounds associated to oxidation of fish muscle[J].Journal of Chromatography A,2008,1192(1):9-16.DOI:10.1016/j.chroma.2008.03.028.
[30]马睿.营养与养殖大黄鱼品质之间关系的初步研究[D].青岛:中国海洋大学,2014:41-50.
[31]贡慧,杨震,刘梦,等.秋刀鱼热加工后挥发性风味成分变化的分析[J].肉类研究,2017,31(1):25-31.DOI:10.7506/rlyj1001-8123-201701005.
[32]HEIEH R J,KINSELLA J E.Oxidation of polyunsaturated fatty acids:mechanisms,products,and inhibition with emphasis on fish[J].Advances in Food&Nutrition Research,1989,33:233-341.DOI:10.1016/s1043-4526(08)60129-1.
[33]冯晓群,韩玲,蒋玉梅,等.甘肃马鹿背最长肌挥发性物质的组成分析[J].甘肃农业大学学报,2008,43(6):159-162.DOI:10.13432/j.cnki.jgsau.2008.06.028.
[34]王璐,王锡昌,刘源.养殖场采样及市售草鱼肉气味成分的比较[J].食品工业科技,2010,31(5):76-80.DOI:10.13386/j.issn1002-0306.2010.05.071.
[35]HAYES K P,BURCH M D.Odorous compounds associated with algal blooms in south australian waters[J].Water Research,1989,23(1):115-121.DOI:10.1016/0043-1354(89)90069-9.
[36]CHA Y J,CADWALLADER K R,BAEJ H H.Volatile flavor components in snow crab cooker effluent and effluent concentrate[J].Journal of Food Science,1993,58(3):525-530.DOI:10.1111/j.1365-2621.1993.tb04316.x.
[37]夏明明,邵晨,刘源.虎纹蛙肌肉挥发性成分和脂肪酸分析[J].食品科学,2011,32(6):217-220.
[38]GIRARD B,DURANCE T.Headspace volatiles of sockeye and pink salmon as affected by retort process[J].Journal of Food Science,2010,65(1):34-39.DOI:10.1111/j.1365-2621.2000.tb15952.x.
[39]章超桦,平野敏行,铃木健,等.鲫的挥发性成分[J].水产学报,2000,24(4):354-358.
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