橄榄油中甘油二酯异构体测定方法研究与应用初探
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摘要
甘油二酯(diacylglycerols,DAGs)异构体(1,3-/1,2-DAGs)在橄榄油的品质鉴别方面具有应用价值,该异构体的比例特征可用于橄榄油新鲜程度的辨别。利用固相萃取小柱分离油脂中DAGs成分,衍生处理后经GC-FID实现了DAGs的定量测定,优化后的衍生条件为衍生温度30℃,衍生时间1 h。该方法最低检出限(S/N=3)为0. 032 mg/m L,RSD值为1. 35%～4. 62%,各甘油二酯成分的回收率为73. 9%～76. 9%。对比分析了6种初榨橄榄油和4种精炼橄榄油,结果表明二者的DAGs异构体比例存在明显不同。该方法设备简单,操作简便,可实现对橄榄油DAGs异构体进行准确测定,为开发橄榄油的真实性检测方法和建立产品标准提供技术支持,对进口初榨橄榄油的口岸监管和市场监管均具有指导意义。
Diacylglycerols isomers( 1,3-/1,2-DAGs) play an important role in identifying olive oil quality. The ratio of DAGs isomers can indicate the freshness of olive oil. Solid phase extraction was used to extract DAGs in oil,and they were quantified by GC-FID after derivatization. Derived at 30 ℃ for 1 h was the optimal derivative condition. The lowest detection limit of this method was 0. 032 mg/m L,the RSD value was 1. 35%-4. 62%,and the average recovery rate of each DAG was 73. 9%-76. 9%. It was found that the ratios of DAGs isomers in six extra-virgin olive oil and four refined olive oil were significantly different. This method was simple and easy to operate. It can be used to accurately determine DAGs isomers in olive oil. It provides technical supports for developing olive oil authenticity detection methods as well as establishing product standards. It also has guiding significance for portal and market regulations on imported extract virgin olive oil.
Diacylglycerols isomers( 1,3-/1,2-DAGs) play an important role in identifying olive oil quality. The ratio of DAGs isomers can indicate the freshness of olive oil. Solid phase extraction was used to extract DAGs in oil,and they were quantified by GC-FID after derivatization. Derived at 30 ℃ for 1 h was the optimal derivative condition. The lowest detection limit of this method was 0. 032 mg/m L,the RSD value was 1. 35%-4. 62%,and the average recovery rate of each DAG was 73. 9%-76. 9%. It was found that the ratios of DAGs isomers in six extra-virgin olive oil and four refined olive oil were significantly different. This method was simple and easy to operate. It can be used to accurately determine DAGs isomers in olive oil. It provides technical supports for developing olive oil authenticity detection methods as well as establishing product standards. It also has guiding significance for portal and market regulations on imported extract virgin olive oil.
引文
[1]何腊平,李兰香,周换景,等. 1,3-甘油二酯的制备研究进展[J].食品研究与开发,2013,34(15):113-116.
[2]孟祥河,毛忠贵,高保军,等.甘油二酯的应用现状[J].中国食品添加剂,2002(4):58-61.
[3] MORITA O,KANPP J F,TAMAKI Y,et al. Safety assessment of dietarydiacylglycerol oil:A two-generation reproductive toxicity study in rats[J]. Food and Chemical Toxicology,2008,46(9):3 059-3 068.
[4] MAKI K C,DAVIDSON MH,TSUSHIMA R,et al. Consumption ofdiacylglycerol oil as part of a reduced-energy diet enhances olss of body weight and fat in compfrison with consumption of a triacylglycerol control oil[J]. Am. J.Clin. Nutr,2002,76(6):1 230-1 236.
[5]刘晓娟.富含甘油二酯的大豆油的制备[D].长春:长春大学,2017.
[6] ZHU Han-jiang,CLEGG M S,SHOEMAKER C F,et al.Characterization of diacylglycerol isomers in edible oils using gas chromatography-ion trap electron ionization mass spectrometry[J]. Journal of Chromatography A,2013,194-202.
[7] COSSIGNANI L,SIMONETTI M S,DAMIANI P. Structural changes of triacylglycerol and diacylglycerol fractions during olive druperipening[J]. European Journa lof Lipid Science and Technology,2001,212:160-164.
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[9] FRANKEL E N. Lipid Oxidation[M]. Cambridge UK:Woodhead Publishing Limited,1998.
[10]孙禧华,王鑫,曹文明.橄榄油质量鉴别若干内源性标记物[J].粮食与油脂,2013,26(9):8-9.
[11] BENARD S,ARNHOLD J,LEHNERT M,et al. Experiments towards quantification of saturated and polyunsaturated diacylglycerols by matrix-assisted laser desorption and ionization time-of-flight mass spectrometry[J]. Chem Phys Lipids,1999,100(1-2):115-125.
[12] FUCHS B. Analysis of phospolipids and glycolipids by thin-layer chromatography-matrix-assisted laser desorption and ionization mass spectrometry[J]. Journal of Chromatography A,2012,1 259(19):62-73.
[13] CALLENDER H L,FORRESTER J S,IVANOVAL P,et al. Quantification of diacylglycerol species from cellular extracts by electrospray ionization mass spectrometry using a linear regression algorithm[J]. Anal Chem,2007,79(1):263-272.
[14] CAMERA E,LUDOVICI M,GALANTE M,et al. Comprehensive analysis of the major lipid classes in sebum by rapid resolution high-performance liquid chromatography and electrospray mass spectrometry[J]. J Lipid Res,2010,51(11):3 377-3 388.
[15] LI Y L,SU X,STAHL P D,et al. Quantification of diacylglycerol molecular species in biological samples by electrospray ionization mass spectrometry after one-step derivatization[J]. Anal Chem,2007,79(4):1 569-1 574.
[16]周君.甘油二酯的制备与高效液相色谱的检测技术分析[J].当代化工研究,2018(2):10-11.
[17]赵欣欣,孔保华,李龙祥,等.甘油二酯的制备及其高效液相色谱的检测技术[J].食品工业,2016,37(11):228-231.
[18] ISO 29822:2009. Vegetable fats and oils-isomers diacylglycerols-determination of relativw amounts of 1,2-and1,3-diacylglycerols[S]. Switzerland:DGF Standard Method,2009.
[19] PEREZ M C,MOREDA W,CERT A. Effects of olive fruit quality and oil storage practices on the diacylglycerol content of virgin olive oils[J]. American Chemical Society,2001,49(2):699-704.
[20]陈佳子.甘油二酯的制备、性质表征及其在油包水型乳状液中的应用研究[D].广州:暨南大学,2018.
[21]陈岩,潘龙.甘油二酯研究进展[J].科技信息,2012(17):19-21.
[22]祝雨筱. 1,2-甘油二酯的酶法合成[D].无锡:江南大学,2017.
[23]高晓红,郑毅,袁建,等.反相高效液相色谱-蒸发光散射检测法测定大豆油中的甘油二酯[J].中国油脂,2014,39(1):65-68.
[24]王宝维,韩海娜,葛文华,等.酶解法催化鹅油制备甘油二酯[J].中国粮油学报,2015,30(3):80-84.
[25] ZHU Hanjiang,TANG Shuaikun,SHOEMAKER C F,et al. Characterization of volatile compounds of virgin olive oil originating from the USA[J]. J Am Oil Chem Soc,2015,92(1):77-85.
[26] LI Xueqi,ZHU Hanjiang,SHOEMAKER C F,et al. The effect of different cold storage conditionson the compositions of extra virgin olive oil[J]. J Am Oil Chem Soc,2014,91(9):1 559-1 570.
[27]樊巧英,曹迪迪,张星星,等.甘油二酯异构体高效液相色谱分析法的建立[J].中国油脂,2017,42(8):131-135.
[2]孟祥河,毛忠贵,高保军,等.甘油二酯的应用现状[J].中国食品添加剂,2002(4):58-61.
[3] MORITA O,KANPP J F,TAMAKI Y,et al. Safety assessment of dietarydiacylglycerol oil:A two-generation reproductive toxicity study in rats[J]. Food and Chemical Toxicology,2008,46(9):3 059-3 068.
[4] MAKI K C,DAVIDSON MH,TSUSHIMA R,et al. Consumption ofdiacylglycerol oil as part of a reduced-energy diet enhances olss of body weight and fat in compfrison with consumption of a triacylglycerol control oil[J]. Am. J.Clin. Nutr,2002,76(6):1 230-1 236.
[5]刘晓娟.富含甘油二酯的大豆油的制备[D].长春:长春大学,2017.
[6] ZHU Han-jiang,CLEGG M S,SHOEMAKER C F,et al.Characterization of diacylglycerol isomers in edible oils using gas chromatography-ion trap electron ionization mass spectrometry[J]. Journal of Chromatography A,2013,194-202.
[7] COSSIGNANI L,SIMONETTI M S,DAMIANI P. Structural changes of triacylglycerol and diacylglycerol fractions during olive druperipening[J]. European Journa lof Lipid Science and Technology,2001,212:160-164.
[8] LO S K,TAN C P,LONG K,et al. Diacylglycerol oilproperties,processes and products:A review[J]. Food Bioprocess Technol,2008,1:223-233.
[9] FRANKEL E N. Lipid Oxidation[M]. Cambridge UK:Woodhead Publishing Limited,1998.
[10]孙禧华,王鑫,曹文明.橄榄油质量鉴别若干内源性标记物[J].粮食与油脂,2013,26(9):8-9.
[11] BENARD S,ARNHOLD J,LEHNERT M,et al. Experiments towards quantification of saturated and polyunsaturated diacylglycerols by matrix-assisted laser desorption and ionization time-of-flight mass spectrometry[J]. Chem Phys Lipids,1999,100(1-2):115-125.
[12] FUCHS B. Analysis of phospolipids and glycolipids by thin-layer chromatography-matrix-assisted laser desorption and ionization mass spectrometry[J]. Journal of Chromatography A,2012,1 259(19):62-73.
[13] CALLENDER H L,FORRESTER J S,IVANOVAL P,et al. Quantification of diacylglycerol species from cellular extracts by electrospray ionization mass spectrometry using a linear regression algorithm[J]. Anal Chem,2007,79(1):263-272.
[14] CAMERA E,LUDOVICI M,GALANTE M,et al. Comprehensive analysis of the major lipid classes in sebum by rapid resolution high-performance liquid chromatography and electrospray mass spectrometry[J]. J Lipid Res,2010,51(11):3 377-3 388.
[15] LI Y L,SU X,STAHL P D,et al. Quantification of diacylglycerol molecular species in biological samples by electrospray ionization mass spectrometry after one-step derivatization[J]. Anal Chem,2007,79(4):1 569-1 574.
[16]周君.甘油二酯的制备与高效液相色谱的检测技术分析[J].当代化工研究,2018(2):10-11.
[17]赵欣欣,孔保华,李龙祥,等.甘油二酯的制备及其高效液相色谱的检测技术[J].食品工业,2016,37(11):228-231.
[18] ISO 29822:2009. Vegetable fats and oils-isomers diacylglycerols-determination of relativw amounts of 1,2-and1,3-diacylglycerols[S]. Switzerland:DGF Standard Method,2009.
[19] PEREZ M C,MOREDA W,CERT A. Effects of olive fruit quality and oil storage practices on the diacylglycerol content of virgin olive oils[J]. American Chemical Society,2001,49(2):699-704.
[20]陈佳子.甘油二酯的制备、性质表征及其在油包水型乳状液中的应用研究[D].广州:暨南大学,2018.
[21]陈岩,潘龙.甘油二酯研究进展[J].科技信息,2012(17):19-21.
[22]祝雨筱. 1,2-甘油二酯的酶法合成[D].无锡:江南大学,2017.
[23]高晓红,郑毅,袁建,等.反相高效液相色谱-蒸发光散射检测法测定大豆油中的甘油二酯[J].中国油脂,2014,39(1):65-68.
[24]王宝维,韩海娜,葛文华,等.酶解法催化鹅油制备甘油二酯[J].中国粮油学报,2015,30(3):80-84.
[25] ZHU Hanjiang,TANG Shuaikun,SHOEMAKER C F,et al. Characterization of volatile compounds of virgin olive oil originating from the USA[J]. J Am Oil Chem Soc,2015,92(1):77-85.
[26] LI Xueqi,ZHU Hanjiang,SHOEMAKER C F,et al. The effect of different cold storage conditionson the compositions of extra virgin olive oil[J]. J Am Oil Chem Soc,2014,91(9):1 559-1 570.
[27]樊巧英,曹迪迪,张星星,等.甘油二酯异构体高效液相色谱分析法的建立[J].中国油脂,2017,42(8):131-135.