定量核磁共振碳谱同时测定食用油中甘油三酯的<i>sn</i>-1,3和<i>sn</i>-2脂肪酸含量

引用本文: 肖坤, 龚灿, 郭强胜, 许旭. 定量核磁共振碳谱同时测定食用油中甘油三酯的sn-1,3和sn-2脂肪酸含量[J]. 分析化学, 2020, 48(6): 802-810. doi: 10.19756/j.issn.0253-3820.191420 shu

Citation: XIAO Kun, GONG Can, GUO Qiang-Sheng, XU Xu. Simultaneous Determination of Fatty Acids at sn-1,3 and sn-2 of Triglyceride in Edible Oils by Quantitative ¹³C-Nuclear Magnetic Resonance[J]. Chinese Journal of Analytical Chemistry, 2020, 48(6): 802-810. doi: 10.19756/j.issn.0253-3820.191420 shu

定量核磁共振碳谱同时测定食用油中甘油三酯的sn-1,3和sn-2脂肪酸含量

上海应用技术大学化学与环境工程学院, 上海 201418
基金项目:
本文系国家自然科学基金项目（No.31671928）和上海市自然科学基金项目（No.15ZR1440800）资助

摘要: 建立了定量核磁共振碳谱（¹³C-qNMR）技术测定食用油中特定位置不饱和脂肪酸含量的方法。使用反转门控去耦技术对食用油中的脂肪酸进行位置特异性分析，针对未完全分离的谱峰，比较了直接普通积分、使用不同的洛伦兹/高斯函数比值去卷积积分等数据处理方式对核磁共振碳谱定量结果的影响，选择以洛伦兹-高斯（3：2）的比例，对谱图进行去卷积拟合，提取sn-1，3和sn-2位亚油酸和油酸两种不饱和脂肪酸的定量峰，测定3种食用油中甘油三酯的饱和脂肪酸、sn-1，3位亚油酸、sn-2位亚油酸、sn-1，3位油酸、sn-2位油酸含量分别为：大豆油（16.2%、27.8%、24.0%、15.5%、7.9%（w/w，下同））；玉米油（15.3%、30.7%、20.5%、20.1%、13.3%）；花生油（18.3%、18.7%、12.5%、24.9%、25.5%）。大豆油中sn-1，3位亚麻酸、sn-2位亚麻酸分别为4.5%和4.0%，玉米油和花生油中未检出亚麻酸。上述结果与¹H-qNMR测定的各脂肪酸总量一致。¹³C-qNMR可对食用油中脂肪酸进行位置特异性分析，无需复杂的样品前处理过程，可区分不饱和脂肪酸的不同位置分布，为在缺乏甘油三酯标样的情况下测量食用油中特定甘油三酯位置异构体成分含量提供了新方法。

关键词:

English

Simultaneous Determination of Fatty Acids at sn-1,3 and sn-2 of Triglyceride in Edible Oils by Quantitative ¹³C-Nuclear Magnetic Resonance

School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China
Received Date: 19 July 2019
Revised Date: 06 March 2020
Fund Project:
This work was supported by the National Natural Science Foundation of China (No. 31671928) and the Natural Science Foundation of Shanghai, China (No. 15ZR1440800).

Abstract: A ¹³C-quantitative nuclear magnetic resonance (qNMR) method was established for determination of content of fatty acid at different positions in edible oil. The positional specificity analysis of sn-1,3 and sn-2 in fatty acids in edible oil was performed using reverse-gated decoupling technique. The direct normal integral, deconvolution integral using different Lorentz-Gaussian ratios, and other data processing methods were compared for the analyzing ¹³C-qNMR unseparated peaks. Then the deconvolution integral with Lorentz-Gauss (3∶2) was selected to extract the quantitative peak areas of two unsaturated fatty acids at sn-1,3 and sn-2, linoleic acid and oleic acid. The content of unsaturated fatty acids in different positions showed that the saturated fatty acids, sn-1 linoleic acid, sn-2 linoleic acid, sn-1,3 oleic acid, sn-2 oleic acid were as follows: soybean oil (16.2%, 27.8%, 24.0%, 15.5%, 7.9% (w/w, the same below)); corn oil (15.3%, 30.7%, 20.5%, 20.1%, 13.3%); peanut oil (18.3%, 18.7%, 12.5%, 24.9%, 25.5%). The sn-1,3 linolenic acid, sn-2 linolenic acid in soybean oil were 4.5% and 4.1%, respectively, but were undetectable in corn oil and peanut oil. The result was in accordance with content of total linoleic acid and total oleic acid detected by above ¹H-qNMR method. ¹³C-qNMR can be applied to distinguish the location and distribution of unsaturated fatty acids with easy sample preparation and flexible operation, providing a method for quantifying the specific triglyceride positional isomer component in edible oil without its standard sample.

Key words:

1. [1]
  FANG Hong-Yun, HE Yu-Na, YU Dong-Mei, GUO Qi-Ya, WANG Xun, XU Xiao-Li, ZHAO Li-Yun. Food and Nutrition in China,2017,23(2):56-58 房红芸,何宇纳,于冬梅,郭齐雅,王寻,许晓丽,赵丽云.中国食物与营养,2017,23(2):56-58
2. [2]
  ZHANG Yao-Li, PEI Xing-Li, GONG Can, HAN Yu-Liang, NI Tian-Qiang, WANG Fan, WANG Sheng-Jun, LU Hai-Peng, XU Xu. Chinese J. Anal. Chem.,2017,45(2):183-190 张耀利,裴兴丽,龚灿,韩玉良,倪天强,王帆,王盛君,卢海鹏,许旭.分析化学, 2017,45(2):183-190
3. [3]
  Helgadottir A, Gretarsdottir S, Thorleifsson G, Hjartarson E, Sigurdsson E, Magnusdottir A, Jonasdottir A, Kristjansson H, Sulem P, Oddsson A, Sveinbjornsson G, Steinthorsdottir V, Rafnar T, Masson G, Jonsdottir I, Olafsson I, Eyjolfsson G I, Sigurdardottir O, Daneshpour M S, Khalili D, Azizi F, Swinkels D W, Kiemeney L, Quyyumi A A, LeveyA I, Patel R S, Hayek S S, Gudmundsdottir I J, Thorgeirsson G, Thorsteinsdottir U, Gudbjartsson D F, Holm H, Stefansson K. Nat. Genetics,2016,48(6):634-639
4. [4]
  Risérus U, Willett W C, Hu F B. Prog. Lipid Res.,2009,48(1):44-51
5. [5]
  Houston D K, Ding J, Lee J S, Garcia M, Kanaya A M, Tylavsky F A, Newman A B, Visser N, Kritchevsky S B. Nutrit. Metab. Cardiovasc. Dis.,2011,21(6):430-437
6. [6]
  LI Jing, WANG Yong, YANG Yao-Dong, LEI Xin-Tao, XIAO Yong. Journal of Southern Agriculture,2016,47(12):2124-2128 李静,王永,杨耀东,雷新涛,肖勇.南方农业学报,2016,47(12):2124-2128
7. [7]
  ZHU Tao-Hua, FAN Lu, QIAN Xiang-Ming, WANG Yan, JING Yin-Cheng. China Oils And Fats,2011,36(5):59-63 朱桃花,范璐,钱向明,王艳,井银成.中国油脂,2011,36 (5):59-63
8. [8]
  LI Bin, QIU Li-Qun, SONG Shao-Fang, GAO Ai-Ying, ZHANG Hao. Chinese Journal of Analysis Laboratory,2014,33(5):528-532 李斌,裘立群,宋少芳,高艾英,张昊.分析试验室,2014,33(5):528-532
9. [9]
  FAN Sheng-Xu, Li Bin, SUN Jun-Ming, HAN Fen-Xia, YAN Shu-Rong, WANG Lan, WANG Lian-Zheng. Chinese Journal of Oil Crop Sciences,2015,37(4):548-553 范胜栩,李斌,孙君明,韩粉霞,闫淑荣,王岚,王连铮.中国油料作物学报,2015, 37(4):548-553
10. [10]
  FAN Jun-Ming, JIA Jun, CHEN Yan. Hubei Agricultural Sciences,2017,56(4):727-730 凡军民,贾君,陈燕.湖北农业科学,2017, 56(4):727-730
11. [11]
  Haddad I, Mozzon M, Strabbioli R, Frega N G. Dairy Sci. Technol.,2012,92(1):37-56
12. [12]
  LOU Ting-Ting, ZHAO Ting, WANG Wei, LIN An-Qing, ZHAO Jing-Yuan. Food Research and Development,2014,35(21):100-102 娄婷婷,赵婷,王伟,林安清,赵璟源.食品研究与开发,2014,35(21):100-102
13. [13]
  LI Sha, WANG Wei-Xiang. Cereals & Oils,2015,28(9):65-67 李莎,王维香.粮食与油脂,2015,28(9):65-67
14. [14]
  LIAO Li-Ping, XIAO Ai-Ping, LENG Juan, YANG Xi-Ai, LIU Liang-Liang, MEI Shi-Yong. China Oils and Fats,2017,42(4):136-139 廖丽萍,肖爱平,冷鹃,杨喜爱,刘亮亮,梅时勇.中国油脂,2017,42(4):136-139
15. [15]
  Delmonte P, Kia A R F, Hu Q, Rader J I. J. AOAC Int.,2009, 92(5):1310-1326
16. [16]
  Barison A, da Silva C W P, Campos F R, Simonelli F, Lenz C A, Ferreira A G. Mag. Reson. Chem.,2010,48(8):642-650
17. [17]
  Fauconnot L, Hau J, Aeschlimann J M, Fay L B, Dionisi F. Rapid Commun. Mass Spectrom.,2004,18(2):218-224
18. [18]
  Kayden H J, Senior J R, Mattson H F. J. Clin. Invest.,1967,46(11):1695-1703
19. [19]
  Myher J J, Marai L, Kuksis A, Kritchevsky D. Lipids,1977,12(10):775-785
20. [20]
  Manganaro F, Myher J J, Kuksis A, Kritchevsky D. Lipids,1981,16(7):508-517
21. [21]
  Berry S E E. Nutrit. Res. Rev.,2009,22(1):3-17
22. [22]
  BEI Pei, SUN Jian-Hua. International Journal of Pediatrics,2014,41(1):58-60 贝斐,孙建华.国际儿科学杂志,2014,41(1):58-60
23. [23]
  SHANG Yun-Peng, SHENG Qing-Hai, WANG Zhen-Yu, ZHANG Zhi-Guo. Journal of the Chinese Cereals and Oils Association, 2010,25(10):119-123 商允鹏,生庆海,王贞瑜,张志国.中国粮油学报,2010,25(10):119-123
24. [24]
  Indelicato S, Bongiorno D, Pitonzo R, Stefano V D, Calabrese V, Indelicato S, Avellone G. J. Chromatogr. A,2017,1515:1-16
25. [25]
  Kim J, Jin G, Lee Y, Chun H S, Ahn S, Kim B H. J. Agric. Food Chem.,2015,63(40):8955-8965
26. [26]
  Gouk S U, Cheng S F, Ong A S H, Chuah C H. Eur. J. Lipid Sci. Technol.,2012,114(5):510-519
27. [27]
  Bottino N R, Vandenburg G A, Reiser R. Lipids,1967,2(6):489-493
28. [28]
  Becker C C, Rosenquist A, Holmer G. Lipids,1993,28(2):147-149
29. [29]
  Igarashi T, Aursand M, Hirata Y, Gribbestad I S, Wada S, Nonaka M. J. Am. Oil Chem. Soc.,2000,77(7):737-748
30. [30]
  Tenailleau E, Lancelin P, Robins R J, Akoka S. Anal. Chem.,2004,76(13):3818-3825
31. [31]
  Aursand M, Jorgensen L, Grasdalen H. Comp. Biochem. Physiol.,1995,112B(2):315-321
32. [32]
  Holtman K M, Chang H M, Jameel H, Kadla J F. J. Wood Chem. Technol.,2006,26(1):21-34
33. [33]
  Vlahov G, Giuliani A A, Re P D. Anal. Methods,2010,2(7):916-923
34. [34]
  Gouk S W, Cheng S F, Malon M, Onga A S H, Chuah C H. Anal. Methods,2013, 5(8):2064-2073
35. [35]
  Vlahov G. Magn. Reson. Chem.,1998,36(5):359-362
36. [36]
  Suárez E R, Mugford P F, Rolle A J, Burton I W, Walter J A, Kralovec J A. J. Am. Oil Chem. Soc., 2010,87(12):1425-1433
37. [37]
  Meusel A, Popkova Y, Dannenberger D, Schiller J. Food Anal. Methods,2017,10(7):2497-2506
38. [38]
  Merchak N, Silvestre V, Loquet D, Rizk T, Akoka S, Bejjani J. Anal. Bioanal. Chem.,2017, 409(1):307-315
39. [39]
  Simova S, Ivanova G, Passov S L. Chem. Phys. Lipids,2003,126(2):167-176
40. [40]
  YAN Bao-Zhen. Graphical Nuclear Magnetic Resonance Technology and Examples. Beijing:Science Press,2010:240 严宝珍.图解核磁共振技术与实例.北京:科学出版社, 2010:240
41. [41]
  National Pharmacopoeia Committee. The Pharmacopoeia of the People's Republic of China (Part IV, 2015 Ed), Beijing:China Medical Science Press, 2015:52-54, 376 国家药典委员会编.中华人民共和国药典 (四部, 2015年版).北京:中国医药科技出版社, 2015:52-54, 376
42. [42]
  GAO Han-Bin, ZHANG Zhen-FANG. Principles and Experimental Methods of Nuclear Magnetic Resonance. Wuhan:Wuhan University Press,2008:25高汉宾,张振芳.核磁共振原理与实验方法.武汉:武汉大学出版社, 2008:25

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沈阳化工大学材料科学与工程学院沈阳 110142

定量核磁共振碳谱同时测定食用油中甘油三酯的sn-1,3和sn-2脂肪酸含量

English

Simultaneous Determination of Fatty Acids at sn-1,3 and sn-2 of Triglyceride in Edible Oils by Quantitative ¹³C-Nuclear Magnetic Resonance

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定量核磁共振碳谱同时测定食用油中甘油三酯的sn-1,3和sn-2脂肪酸含量

English

Simultaneous Determination of Fatty Acids at sn-1,3 and sn-2 of Triglyceride in Edible Oils by Quantitative 13C-Nuclear Magnetic Resonance

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

Simultaneous Determination of Fatty Acids at sn-1,3 and sn-2 of Triglyceride in Edible Oils by Quantitative ¹³C-Nuclear Magnetic Resonance

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