Massworks~(TM)结合NIST11谱库在羊油香气成分准确定性分析中的应用
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摘要
应用Massworks~(TM)质谱解析软件结合NIST11谱库,定性分析羊油的香气成分。在Massworks~(TM)质谱解析软件中,以全氟三丁胺质谱图为标准建立质谱校正函数,对热脱附-气相色谱-质谱联用法(TD-GC/MS)采集的羊油香气原始扫描谱图进行质量轴和峰形校正,通过低分辨质谱获得各化合物的精确质量数,并利用同位素峰形校正技术(CLIPs Search)进行检索,获取未知目标化合物的分子式,同时与NIST11谱库的检索结果比对。结果表明,通过Massworks~(TM)与NIST11谱库结合实现了快速、准确定性分析羊油香气成分,最终确定42种香气成分。利用Masswork~(TM)软件的参数优化,解决了NIST11谱库中检索匹配度低、存在共流出化合物以及目标化合物无分子离子峰等问题,获取了化合物离子碎片信息并进行了解析。该定性方法可为未知天然产物香气成分的分析提供方法参考。
Massworks~(TM) mass spectrometry combined with NIST11 library was used to the quasi-deterministic analysis of the aroma components of goat oil. Mass spectrometry correction function was established using the mass spectrogram of perfluorotributylamine(PFTBA) as a standard in Massworks~(TM) mass spectrometry analysis software. Then, the mass-axis correction and peak shape correction were performed on the original scanning chromatogram of the sample collected by TD-GC/MS. The accurate mass of each compound was obtained on a low-resolution mass spectrum, and the molecular formulas of unknown target compounds were obtained by isotope peak shape correction technology(CLIPs Search). The target compounds were determined by comparing the results of Massworks~(TM) and NIST11 library search. Finally, the results of Massworks~(TM) mass spectrometry software and NIST11 library search were verified by standards. The results showed that the combination of Massworks~(TM) and NIST11 libraries enabled fast and quasi-deterministic analysis of the aroma components of goat oil. Through the background subtraction function and parameter optimization of Masswork~(TM) software, ion fragment information of compound can be obtained and analyzed to obtain the exact molecular weight and molecular formula of the target compound. In this experiment, qualitative analysis was conducted for the aroma components of different parts of the sheep body. Finally, 42 aroma components of sheep oil were identified, including 15 kinds of hydrocarbon, 14 kinds of aldehydes, 4 kinds of alcohols, 3 kinds of ketones, 2 kinds of lipids, 2 kinds of ethers, and 2 kinds of other substances. Their relative contents were compared using the area normalization method. This method not only solved the qualitative uncertainty of the natural product aroma components and the uniqueness of the NIST11 spectral library, but also provided a reference for the consumption of sheep oil and the separation of aroma components. On the other hand, the qualitative analysis method can provide new ideas and references for the analysis of aroma components of natural products in the future. The quasi-determinacy of the aroma components of sheep oil in animal oil can be used as an effective qualitative method to achieve simple and accurate qualitative analysis.
Massworks~(TM) mass spectrometry combined with NIST11 library was used to the quasi-deterministic analysis of the aroma components of goat oil. Mass spectrometry correction function was established using the mass spectrogram of perfluorotributylamine(PFTBA) as a standard in Massworks~(TM) mass spectrometry analysis software. Then, the mass-axis correction and peak shape correction were performed on the original scanning chromatogram of the sample collected by TD-GC/MS. The accurate mass of each compound was obtained on a low-resolution mass spectrum, and the molecular formulas of unknown target compounds were obtained by isotope peak shape correction technology(CLIPs Search). The target compounds were determined by comparing the results of Massworks~(TM) and NIST11 library search. Finally, the results of Massworks~(TM) mass spectrometry software and NIST11 library search were verified by standards. The results showed that the combination of Massworks~(TM) and NIST11 libraries enabled fast and quasi-deterministic analysis of the aroma components of goat oil. Through the background subtraction function and parameter optimization of Masswork~(TM) software, ion fragment information of compound can be obtained and analyzed to obtain the exact molecular weight and molecular formula of the target compound. In this experiment, qualitative analysis was conducted for the aroma components of different parts of the sheep body. Finally, 42 aroma components of sheep oil were identified, including 15 kinds of hydrocarbon, 14 kinds of aldehydes, 4 kinds of alcohols, 3 kinds of ketones, 2 kinds of lipids, 2 kinds of ethers, and 2 kinds of other substances. Their relative contents were compared using the area normalization method. This method not only solved the qualitative uncertainty of the natural product aroma components and the uniqueness of the NIST11 spectral library, but also provided a reference for the consumption of sheep oil and the separation of aroma components. On the other hand, the qualitative analysis method can provide new ideas and references for the analysis of aroma components of natural products in the future. The quasi-determinacy of the aroma components of sheep oil in animal oil can be used as an effective qualitative method to achieve simple and accurate qualitative analysis.
引文
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[5] 魏长庆,周琦,刘文玉. HS-SPME-GC-MS分析新疆胡麻油挥发性成分的技术优化[J]. 食品科学,2017,38(14):151-157. WEI Changqing, ZHOU Qi, LIU Wenyu. Optimization of headspace solid phase microextraction (HS-SPME) for analysis of volatile constituents of flaxseed oil from xinjiang by gas chromatography-mass spectrometry (GC-MS)[J]. Food Science, 2017, 38(14): 151-157(in Chinese).
[6] 秦早,杨冉,高桂园,等. 顶空固相微萃取结合气质联用分析芝麻油和芝麻香精的挥发性成分[J]. 食品科学,2012,33(24):263-268. QIN Zao, YANG Ran, GAO Guiyuan, et al. Determination of volatile compounds in sesame oil and sesame flavor using headspace solid-phase microextraction and GC-MS[J]. Food Science, 2012, 33(24): 263-268(in Chinese).
[7] 顾赛麒,张晶晶. 花生油在不同热处理温度下特征性香气成分鉴别研究[J]. 食品工业科技,2013,34(2):133-138. GU Saiqi, ZHANG Jingjing. Identification on characteristic aroma components of peanut oil under different temperatures during thermal treatment[J]. Food Science and Technology, 2013, 34(2): 133-138(in Chinese).
[8] 周琦,黄凤洪,杨湄,等. 番茄籽油的挥发性成分分析[J]. 中国油脂,2016,41(9):46-50. ZHOU Qi, HUANG Fenghong, YANG Mei, et al. Volatile components of tomato seed oil[J]. China Oils and Fats, 2016, 41(9): 46-50(in Chinese).
[9] 李苑雯,陈素娟,柏文良,等. 花生油香气特征在其属性识别中的初步应用[J]. 食品与发酵工业,2013,39(7):193-199. LI Yuanwen, CHEN Sujuan, BAI Wenliang, et al. Primary application of aromatic characteristic in peanut oil discrimination[J]. Food and Fermentation Industries, 2013, 39(7): 193-199(in Chinese).
[10] 雷春妮,周围,蒋玉梅,等. 热脱附-气相色谱/质谱联用分析鲜食玉米香气成分[J]. 食品工业科技,2014,35(2):71-75. LEI Chunni, ZHOU Wei, JIANG Yumei, et al. Thermal desorption coupled to GC-MS for analyzing aroma components in fresh corn[J]. Science and Technology of Food Industry, 2014, 35(2): 71-75(in Chinese).
[11] 张雯雯,郑华,张弘,等. 缅栀子花朵挥发性成分的全自动热脱附-气相色谱-质谱分析[J]. 食品科学,2010,31(18):236-238. ZHANG Wenwen, ZHENG Hua, ZHANG Hong, et al. Volatile composition analysis of the fresh flowers of plumeria rubra linn. cv. acutifolia by automatic thermal desorption-gas chromatography-mass spectrometry[J]. Food Science, 2010, 31(18): 236-238(in Chinese).
[12] 马慧莲,金静,李云,等. 热脱附-气相色谱-质谱法应用于工业源废气中挥发性有机物的目标和非目标筛查[J]. 色谱,2017,35(10):1 094-1 099. MA Huilian, JIN Jing, LI Yun, et al. Target and non-target screening of volatile organic compounds In industrial exhaust gas using thermal desorption-gas chromatography-mass spectrometry[J]. Chinese Journal of Chromatography, 2017, 35(10): 1 094-1 099(in Chinese).
[13] 李雪生,李子昂,王正全,等. 精确质量数在单四极杆质谱定性分析农药中的应用[J]. 高等学校化学学报,2010,31(12):2 383-2 389. LI Xuesheng, LI Ziang, WANG Zhengquan, et al. Application of accurate mass and elemental composition determination for pesticides identification using a unit mass resolution gas chromatography/mass spectrometry[J]. Chemical Journal of Chinese Universities, 2010, 31(12): 2 383-2 389(in Chinese).
[14] 李斌,周围. MassWorksTM与气相色谱-质谱联用分析洋甘菊精油成分[J]. 质谱学报,2011,32(4):241-245. LI Bin, ZHOU Wei. Analysis of essential oils from chamomila recutita L.by massworksTM and gas chromatography-mass spectrometry[J]. Journal of Mass Spectrometry Society, 2011, 32(4): 241-245(in Chinese).
[15] 王亚男,汪聪慧,李卫建. 农药残留分析中准确定性新技术——Massworks[J]. 中国农业科技导报,2009,(S1):39-42. WANG Yanan, WANG Conghui, LI Weijian. A new technology for accurate identify pesticide residues massworks[J]. Chinese Journal of Agricultural Science and Technology, 2009, (S1): 39-42(in Chinese).
[16] 周围,张雅珩,周小平. 中国苦水玫瑰精油中部分天然产物的质谱分析与元素组成的确定[J]. 检验检疫学刊,2010,20(5):1-4,18. ZHOU Wei, ZHANG Yaheng, ZHOU Xiaoping. Mass spectrum analysis and elemental composition identification of partial natural products in esential oil of Chinese kushui rose[J]. Journal of Inspection and Quarantine, 2010, 20(5): 1-4, 18(in Chinese).
[17] 李卫建,袁有荣,欧阳伟民,等. MassWorksTM分子式识别技术在质谱中应用[J]. 现代仪器,2010,16(5):11-14,19. LI Weijian, YUAN Yourong, OUYANG Wei-min, et al. MassWorksTM molecular recognition in mass spectrometry[J]. Modern Instrument, 2010, 16(5): 11-14, 19(in Chinese).
[18] SPARKMAN O D. Mass spectrometry Pittcon? 2005[J]. Journal of the American Society for Mass Spectrometry, 2007, 18(6): 1 146-1 159.
[19] SAM G, JING P, BORIS I, et al. The role of ozone in the formation and structural evolution of graphene oxide obtained from nanographite[J]. Carbon, 2017, 122(2 017): 411-421.
[20] ZHOU W, ZHANG Y, XU H, et al. Determination of elemental composition of volatile organic compounds from Chinese rose oil by spectral accuracy and mass accuracy[J]. Rapid Commun Mass Spectrom, 2011, (25): 3 097-3 102.
[21] 李斌. Massworks软件在环境有机污染物质谱解析中的应用研究[D]. 兰州:西北师范大学,2012.
[22] 冯丽丽,胡晓芳,于晓娟,等. 热脱附-气相色谱-三重四极杆串联质谱法测定环境空气中的挥发性有机物[J]. 色谱,2016,34(2):209-214. FENG Lili, HU Xiaofang, YU Xiaojuan, et al. Determination of volatile organic compounds in ambient air by thermal desorption-gas chromatography-triple quadrupole tandem mass spectrometry[J]. Chinese Journal of Chromatography, 2016, 34(2): 209-214(in Chinese).
[23] 王光辉,熊少祥. 有机质谱解析[M]. 北京:化学工业出版社,2005:81-90.
[24] 周立华,牟德华,李艳. 7种小浆果香气物质的GC-MS检测与主成分分析[J]. 食品科学,2017,38(2):184-190. ZHOU Lihua, MOU Dehua, LI Yan. GC-MS detection combined with principal component analysis to study the aroma compounds of seven small berries[J]. Food Science, 2017, 38(2): 184-190(in Chinese).
[25] 李伟,罗瑞明,李亚蕾,等. 宁夏滩羊肉的特征香气成分分析[J]. 现代食品科技,2013,29(5):1 173-1 177. LI Wei, LUO Ruiming, LI Yalei, et al. Analysis of characteristic aroma compounds of ningxia tan mutton[J]. Modern Food Science and Technology, 2013, 29(5): 1 173-1 177(in Chinese).
[26] 李伟. 冷冻干燥对滩羊肉香气成分迁移的影响[D]. 银川:宁夏大学,2013.
[2] 王同珍,陈孝建,安爱,等. 气相色谱-质谱技术结合化学计量学对5种动物油进行判别分析[J]. 分析测试学报,2016,35(5):557-562. WANG Tongzhen, CHEN Xiaojian, AN Ai, et al. Discriminant analysis of five kinds of animal oils by gas chromatography mass spectrometry combined with chemometrics[J]. Journal of Analytical Science,2016, 35(5): 557-562(in Chinese).
[3] 关媛,邬国英,林西平,等. 羊油生物柴油低温流动性能的改进[J]. 中国油脂,2009,34(10):54-57. GUAN Yuan, WU Guoying, LIN Xiping, et al. Improvement of low-temperature flow ability of biodiesel from mutton[J]. Chinese Fats and Oils, 2009, 34(10): 54-57(in Chinese).
[4] MáNICA B, VIRGINIA C R, CAMPO M M, et al. Gas chromatographic-olfactometric characterisation of headspace and mouthspace key aroma compounds in fresh and frozen lamb meat[J]. Food Chemistry, 2011, (129): 1 909-1 918.
[5] 魏长庆,周琦,刘文玉. HS-SPME-GC-MS分析新疆胡麻油挥发性成分的技术优化[J]. 食品科学,2017,38(14):151-157. WEI Changqing, ZHOU Qi, LIU Wenyu. Optimization of headspace solid phase microextraction (HS-SPME) for analysis of volatile constituents of flaxseed oil from xinjiang by gas chromatography-mass spectrometry (GC-MS)[J]. Food Science, 2017, 38(14): 151-157(in Chinese).
[6] 秦早,杨冉,高桂园,等. 顶空固相微萃取结合气质联用分析芝麻油和芝麻香精的挥发性成分[J]. 食品科学,2012,33(24):263-268. QIN Zao, YANG Ran, GAO Guiyuan, et al. Determination of volatile compounds in sesame oil and sesame flavor using headspace solid-phase microextraction and GC-MS[J]. Food Science, 2012, 33(24): 263-268(in Chinese).
[7] 顾赛麒,张晶晶. 花生油在不同热处理温度下特征性香气成分鉴别研究[J]. 食品工业科技,2013,34(2):133-138. GU Saiqi, ZHANG Jingjing. Identification on characteristic aroma components of peanut oil under different temperatures during thermal treatment[J]. Food Science and Technology, 2013, 34(2): 133-138(in Chinese).
[8] 周琦,黄凤洪,杨湄,等. 番茄籽油的挥发性成分分析[J]. 中国油脂,2016,41(9):46-50. ZHOU Qi, HUANG Fenghong, YANG Mei, et al. Volatile components of tomato seed oil[J]. China Oils and Fats, 2016, 41(9): 46-50(in Chinese).
[9] 李苑雯,陈素娟,柏文良,等. 花生油香气特征在其属性识别中的初步应用[J]. 食品与发酵工业,2013,39(7):193-199. LI Yuanwen, CHEN Sujuan, BAI Wenliang, et al. Primary application of aromatic characteristic in peanut oil discrimination[J]. Food and Fermentation Industries, 2013, 39(7): 193-199(in Chinese).
[10] 雷春妮,周围,蒋玉梅,等. 热脱附-气相色谱/质谱联用分析鲜食玉米香气成分[J]. 食品工业科技,2014,35(2):71-75. LEI Chunni, ZHOU Wei, JIANG Yumei, et al. Thermal desorption coupled to GC-MS for analyzing aroma components in fresh corn[J]. Science and Technology of Food Industry, 2014, 35(2): 71-75(in Chinese).
[11] 张雯雯,郑华,张弘,等. 缅栀子花朵挥发性成分的全自动热脱附-气相色谱-质谱分析[J]. 食品科学,2010,31(18):236-238. ZHANG Wenwen, ZHENG Hua, ZHANG Hong, et al. Volatile composition analysis of the fresh flowers of plumeria rubra linn. cv. acutifolia by automatic thermal desorption-gas chromatography-mass spectrometry[J]. Food Science, 2010, 31(18): 236-238(in Chinese).
[12] 马慧莲,金静,李云,等. 热脱附-气相色谱-质谱法应用于工业源废气中挥发性有机物的目标和非目标筛查[J]. 色谱,2017,35(10):1 094-1 099. MA Huilian, JIN Jing, LI Yun, et al. Target and non-target screening of volatile organic compounds In industrial exhaust gas using thermal desorption-gas chromatography-mass spectrometry[J]. Chinese Journal of Chromatography, 2017, 35(10): 1 094-1 099(in Chinese).
[13] 李雪生,李子昂,王正全,等. 精确质量数在单四极杆质谱定性分析农药中的应用[J]. 高等学校化学学报,2010,31(12):2 383-2 389. LI Xuesheng, LI Ziang, WANG Zhengquan, et al. Application of accurate mass and elemental composition determination for pesticides identification using a unit mass resolution gas chromatography/mass spectrometry[J]. Chemical Journal of Chinese Universities, 2010, 31(12): 2 383-2 389(in Chinese).
[14] 李斌,周围. MassWorksTM与气相色谱-质谱联用分析洋甘菊精油成分[J]. 质谱学报,2011,32(4):241-245. LI Bin, ZHOU Wei. Analysis of essential oils from chamomila recutita L.by massworksTM and gas chromatography-mass spectrometry[J]. Journal of Mass Spectrometry Society, 2011, 32(4): 241-245(in Chinese).
[15] 王亚男,汪聪慧,李卫建. 农药残留分析中准确定性新技术——Massworks[J]. 中国农业科技导报,2009,(S1):39-42. WANG Yanan, WANG Conghui, LI Weijian. A new technology for accurate identify pesticide residues massworks[J]. Chinese Journal of Agricultural Science and Technology, 2009, (S1): 39-42(in Chinese).
[16] 周围,张雅珩,周小平. 中国苦水玫瑰精油中部分天然产物的质谱分析与元素组成的确定[J]. 检验检疫学刊,2010,20(5):1-4,18. ZHOU Wei, ZHANG Yaheng, ZHOU Xiaoping. Mass spectrum analysis and elemental composition identification of partial natural products in esential oil of Chinese kushui rose[J]. Journal of Inspection and Quarantine, 2010, 20(5): 1-4, 18(in Chinese).
[17] 李卫建,袁有荣,欧阳伟民,等. MassWorksTM分子式识别技术在质谱中应用[J]. 现代仪器,2010,16(5):11-14,19. LI Weijian, YUAN Yourong, OUYANG Wei-min, et al. MassWorksTM molecular recognition in mass spectrometry[J]. Modern Instrument, 2010, 16(5): 11-14, 19(in Chinese).
[18] SPARKMAN O D. Mass spectrometry Pittcon? 2005[J]. Journal of the American Society for Mass Spectrometry, 2007, 18(6): 1 146-1 159.
[19] SAM G, JING P, BORIS I, et al. The role of ozone in the formation and structural evolution of graphene oxide obtained from nanographite[J]. Carbon, 2017, 122(2 017): 411-421.
[20] ZHOU W, ZHANG Y, XU H, et al. Determination of elemental composition of volatile organic compounds from Chinese rose oil by spectral accuracy and mass accuracy[J]. Rapid Commun Mass Spectrom, 2011, (25): 3 097-3 102.
[21] 李斌. Massworks软件在环境有机污染物质谱解析中的应用研究[D]. 兰州:西北师范大学,2012.
[22] 冯丽丽,胡晓芳,于晓娟,等. 热脱附-气相色谱-三重四极杆串联质谱法测定环境空气中的挥发性有机物[J]. 色谱,2016,34(2):209-214. FENG Lili, HU Xiaofang, YU Xiaojuan, et al. Determination of volatile organic compounds in ambient air by thermal desorption-gas chromatography-triple quadrupole tandem mass spectrometry[J]. Chinese Journal of Chromatography, 2016, 34(2): 209-214(in Chinese).
[23] 王光辉,熊少祥. 有机质谱解析[M]. 北京:化学工业出版社,2005:81-90.
[24] 周立华,牟德华,李艳. 7种小浆果香气物质的GC-MS检测与主成分分析[J]. 食品科学,2017,38(2):184-190. ZHOU Lihua, MOU Dehua, LI Yan. GC-MS detection combined with principal component analysis to study the aroma compounds of seven small berries[J]. Food Science, 2017, 38(2): 184-190(in Chinese).
[25] 李伟,罗瑞明,李亚蕾,等. 宁夏滩羊肉的特征香气成分分析[J]. 现代食品科技,2013,29(5):1 173-1 177. LI Wei, LUO Ruiming, LI Yalei, et al. Analysis of characteristic aroma compounds of ningxia tan mutton[J]. Modern Food Science and Technology, 2013, 29(5): 1 173-1 177(in Chinese).
[26] 李伟. 冷冻干燥对滩羊肉香气成分迁移的影响[D]. 银川:宁夏大学,2013.
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