高效液相色谱测定番茄制品中的三种功能性脂肪酸
|
摘要
通过高效液相色谱-质谱技术和高效液相色谱技术对番茄制品中9-羟基-10(E),12(Z)-十八碳二烯酸、9-羰基-10(E),12(Z)-十八碳二烯酸和9-羰基-10 (E),12 (E)-十八碳二烯酸三种功能性脂肪酸进行定性定量分析。结果表明,在色谱柱为Eclipse XDB-C18(4.6 mm×250 mm,5μm),流动相为0.005%的三氟乙酸水溶液和0.005%的三氟乙酸乙腈溶液,检测波长为234、280 nm的条件下,番茄制品中的三种脂肪酸在20 min内得到较好分离,重复性好(RSD≤2.13%),精密度高(RSD≤0.70%),稳定性好(RSD≤0.98%),加标回收结果准确可靠(平均回收率分别为99.78%、99.70%、99.39%,RSD≤3.38%)。该色谱方法快速、准确、可靠;测试结果表明,新鲜番茄中不含有这三种功能性脂肪酸,其仅存在于番茄制品中,且加工工艺对其含量影响较大;此外9-羟基-10(E),12(Z)-十八碳二烯酸为首次在番茄制品中发现。
The Three functional fatty acids of 9-hydroxy-10 E,12 Z-octadecadienoic acid,9-oxo-10 E,12 Z-octadecadienoic acid and 9-oxo-10 E,12 E-octadecadienoic acid in tomato products were identified and analyzed by high performance liquid chromatography-mass spectrometry and high performance liquid chromatography.The column was Eclipse XDB-C18 (4.6 mm ×250 mm,5 μm) and the mobile phase were made up of 0.005% trifluoroacetic acid water and 0.005% trifluoroacetic acid acetonitrile.The detection wavelength was set to 234,280 nm.The results showed that the three fatty acids were well separated within 20 min,with good repeatability (RSD ≤2.13%),high precision (RSD ≤0.70%),good stability (RSD ≤0.98%) and reliable recovery (RSD≤3.38%).A rapid and accurate method for the determination of 9-hydroxy-10 E,12 Z-octadecadienoic acid,9-oxo-10 E,12 Z-octadecadienoic acid and 9-oxo-10 E,12 E-octadecadienoic acid in tomato products was established.The results showed that fresh tomato did not contain these three kinds of functional fatty acids,which only existed in tomato products,and the processing had the greater impact on the content. Furthermore,the 9-hydroxy-10 E,12 Z-octadecadienoic acid was discovered for first time in tomato products.
The Three functional fatty acids of 9-hydroxy-10 E,12 Z-octadecadienoic acid,9-oxo-10 E,12 Z-octadecadienoic acid and 9-oxo-10 E,12 E-octadecadienoic acid in tomato products were identified and analyzed by high performance liquid chromatography-mass spectrometry and high performance liquid chromatography.The column was Eclipse XDB-C18 (4.6 mm ×250 mm,5 μm) and the mobile phase were made up of 0.005% trifluoroacetic acid water and 0.005% trifluoroacetic acid acetonitrile.The detection wavelength was set to 234,280 nm.The results showed that the three fatty acids were well separated within 20 min,with good repeatability (RSD ≤2.13%),high precision (RSD ≤0.70%),good stability (RSD ≤0.98%) and reliable recovery (RSD≤3.38%).A rapid and accurate method for the determination of 9-hydroxy-10 E,12 Z-octadecadienoic acid,9-oxo-10 E,12 Z-octadecadienoic acid and 9-oxo-10 E,12 E-octadecadienoic acid in tomato products was established.The results showed that fresh tomato did not contain these three kinds of functional fatty acids,which only existed in tomato products,and the processing had the greater impact on the content. Furthermore,the 9-hydroxy-10 E,12 Z-octadecadienoic acid was discovered for first time in tomato products.
引文
[1]Ahuja K D K,Ashton E L.Effects of two lipid-lowering,carotenoid-controlled diets on the oxidative modification of lowdensity lipoproteins in free-living humans[J].Clinical Science,2003,105(3):355-361.
[2]Ried K,Fakler P.Protective effect of lycopene on serum cholesterol and blood pressure:Meta-analyses of intervention trials[J].Maturitas,2011,68(4):299-310.
[3]Hirose A,Terauchi M,Tamura M,et al.Tomato juice intake increases resting energy expenditure and improves hypertriglyceridemia in middle-aged women:An open-label,single-arm study[J].Nutrition Journal,2015,14(1):34.
[4]Takahashi H,Kamakari K,Suzuki H,et al.Localization of 9-and 13-oxo-octadecadienoic acids in tomato fruit[J].Bioscience,Biotechnology,and Biochemistry,2014,78(10):1761-1764.
[6]Tontonoz P,Nagy L,Alvarez J G A,et al.PPARγpromotes monocyte/macrophage differentiation and uptake of oxidized LDL[J].Cell,1998,93(2):241-252.
[7]Moch D,Schewe T,Kühn H,et al.The linoleic acid metabolite9DS-hydroxy-10,12(E,Z)-octadecadienoic acid is a strong proinflammatory mediator in an experimental wound healing model of the rat[J].Biomedica Biochimica Acta,1990,49(4):201-207.
[8]廖丽姿,刘磊,田卫东.PPARγ天然激动剂的研究进展[J].现代生物医学进展,2009(7):1381-1383.
[9]Nagy L,Tontonoz P,Alvarez J G A,et al.Oxidized LDLregulates macrophage gene expression through ligand activation of PPARγ[J].Cell,1998,93(2):229-240.
[10]Ku G,Thomas C E,Akeson A L,et al.Induction of interleukin 1 beta expression from human peripheral blood monocyte-derived macrophages by 9-hydroxyoctadecadienoic acid[J].Journal of Biological Chemistry,1992,267(20):14183-14188.
[11]Zhao R,Zhou H,Su S B.A critical role for interleukin-1βin the progression of autoimmune diseases[J].International Immunopharmacology,2013,17(3):658-669.
[12]Dinarello C A.The IL-1 family and inflammatory diseases[J].Clinical and Experimental Rheumatology,2002,20(5;SUPP/27):S1-S13.
[13]Contassot E,Beer H D,French L E.Interleukin-1,inflammasomes,autoinflammation and the skin[J].Swiss Medical Weekly,2012,142(0):w13590.
[14]Ou L,Ip C,Lisafeld B,et al.Conjugated linoleic acid induces apoptosis of murine mammary tumor cells via Bcl-2 loss[J].Biochemical and Biophysical Research Communications,2007,356(4):1044-1049.
[15]Zhao B,Sakurai Y,Shibata K,et al.Cytotoxic fatty acid ketodienes from eggplants[J].Japanese Journal of Food Chemistry and Safety,2014,21(1):42-47.
[16]马晶晶,章涛.PPARγ功能与疾病关系研究进展[J].中国药理学通报,2012,28(5):601-604.
[17]Levandi T,Püssa T,Vaher M,et al.Oxidation products of free polyunsaturated fatty acids in wheat varieties[J].European Journal of Lipid Science and Technology,2009,111(7):715-722.
[18]Püssa T,Raudsepp P,Toomik P,et al.A study of oxidation products of free polyunsaturated fatty acids in mechanically deboned meat[J].Journal of Food Composition and Analysis,2009,22(4):307-314.
[19]Spiteller P,Spiteller G.9-Hydroxy-10,12-octadecadienoic acid(9-HODE)and 13-hydroxy-9,11-octadecadienoic acid(13-HODE):excellent markers for lipid peroxidation[J].Chemistry and Physics of Lipids,1997,89(2):131-139.
[20]Dufour C,Loonis M.Regio-and stereoselective oxidation of linoleic acid bound to serum albumin:Identification by ESI-mass spectrometry and NMR of the oxidation products[J].Chemistry and Physics of Lipids,2005,138(1):60-68.
[2]Ried K,Fakler P.Protective effect of lycopene on serum cholesterol and blood pressure:Meta-analyses of intervention trials[J].Maturitas,2011,68(4):299-310.
[3]Hirose A,Terauchi M,Tamura M,et al.Tomato juice intake increases resting energy expenditure and improves hypertriglyceridemia in middle-aged women:An open-label,single-arm study[J].Nutrition Journal,2015,14(1):34.
[4]Takahashi H,Kamakari K,Suzuki H,et al.Localization of 9-and 13-oxo-octadecadienoic acids in tomato fruit[J].Bioscience,Biotechnology,and Biochemistry,2014,78(10):1761-1764.
[6]Tontonoz P,Nagy L,Alvarez J G A,et al.PPARγpromotes monocyte/macrophage differentiation and uptake of oxidized LDL[J].Cell,1998,93(2):241-252.
[7]Moch D,Schewe T,Kühn H,et al.The linoleic acid metabolite9DS-hydroxy-10,12(E,Z)-octadecadienoic acid is a strong proinflammatory mediator in an experimental wound healing model of the rat[J].Biomedica Biochimica Acta,1990,49(4):201-207.
[8]廖丽姿,刘磊,田卫东.PPARγ天然激动剂的研究进展[J].现代生物医学进展,2009(7):1381-1383.
[9]Nagy L,Tontonoz P,Alvarez J G A,et al.Oxidized LDLregulates macrophage gene expression through ligand activation of PPARγ[J].Cell,1998,93(2):229-240.
[10]Ku G,Thomas C E,Akeson A L,et al.Induction of interleukin 1 beta expression from human peripheral blood monocyte-derived macrophages by 9-hydroxyoctadecadienoic acid[J].Journal of Biological Chemistry,1992,267(20):14183-14188.
[11]Zhao R,Zhou H,Su S B.A critical role for interleukin-1βin the progression of autoimmune diseases[J].International Immunopharmacology,2013,17(3):658-669.
[12]Dinarello C A.The IL-1 family and inflammatory diseases[J].Clinical and Experimental Rheumatology,2002,20(5;SUPP/27):S1-S13.
[13]Contassot E,Beer H D,French L E.Interleukin-1,inflammasomes,autoinflammation and the skin[J].Swiss Medical Weekly,2012,142(0):w13590.
[14]Ou L,Ip C,Lisafeld B,et al.Conjugated linoleic acid induces apoptosis of murine mammary tumor cells via Bcl-2 loss[J].Biochemical and Biophysical Research Communications,2007,356(4):1044-1049.
[15]Zhao B,Sakurai Y,Shibata K,et al.Cytotoxic fatty acid ketodienes from eggplants[J].Japanese Journal of Food Chemistry and Safety,2014,21(1):42-47.
[16]马晶晶,章涛.PPARγ功能与疾病关系研究进展[J].中国药理学通报,2012,28(5):601-604.
[17]Levandi T,Püssa T,Vaher M,et al.Oxidation products of free polyunsaturated fatty acids in wheat varieties[J].European Journal of Lipid Science and Technology,2009,111(7):715-722.
[18]Püssa T,Raudsepp P,Toomik P,et al.A study of oxidation products of free polyunsaturated fatty acids in mechanically deboned meat[J].Journal of Food Composition and Analysis,2009,22(4):307-314.
[19]Spiteller P,Spiteller G.9-Hydroxy-10,12-octadecadienoic acid(9-HODE)and 13-hydroxy-9,11-octadecadienoic acid(13-HODE):excellent markers for lipid peroxidation[J].Chemistry and Physics of Lipids,1997,89(2):131-139.
[20]Dufour C,Loonis M.Regio-and stereoselective oxidation of linoleic acid bound to serum albumin:Identification by ESI-mass spectrometry and NMR of the oxidation products[J].Chemistry and Physics of Lipids,2005,138(1):60-68.