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LC/MS Analysis of Cyclo Fatty Acid-containing Triacylglycerols in Cottonseed Oil

Received: 22 December 2019     Accepted: 15 January 2020     Published: 31 January 2020
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Abstract

We measured the constituent triacylglycerol of cotton oil, the only edible oil containing a cyclo fatty acid. Due to the difficulty of obtaining a standard for triacylglycerols containing cyclo fatty acids, cotton oil is analyzed using cyclo triacylglycerol in kapok oil as a reference. Analytical methods used liquid chromatography fast atom bombardment mass spectrometry (LC / FAB-MS) using a matrix of 3% m-NBA containing 3 mM NaCl, and orthogonal transfer method for APCI / TOF-MS. FAB mass spectral properties of triacylglycerols containing cyclo fatty acids can be observed with [M + Na]+, [M-1]+ molecular ions, and [M- (RCOO)] + fragments. In the orthogonal APCI / TOF-MS spectrum, only the [M-1] + molecular ion appears, so that the presence of triacylglycerol containing CPFA becomes apparent. On the other hand, chain triacylglycerol can be observed as [M + 1]+ molecular ions and [M- (RCOO)]+ fragments. Based on these observations, triacylglycerols containing ten types of cyclo fatty acids were successfully successfully detected in crude cottonseed oil. In addition, the APCI/TOF-MS technique successfully detected dilinoleoyl-marvalyl-glycerol and palmtoyl-linoleoyl-marvalyl glycerol in the purified cottonseed oil.

Published in Science Journal of Analytical Chemistry (Volume 8, Issue 1)
DOI 10.11648/j.sjac.20200801.13
Page(s) 12-17
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This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2020. Published by Science Publishing Group

Keywords

LC/FAB-MS, Cyclo Fatty Acid, Kapok Oil, Cottonseed Oil

References
[1] Macfarlane, J, J.; Shenstone, F, S.; Vickery, J, R (1957). Malvalic Acid and its Structure. Nature. 179: 830-831.
[2] Wilson, T. L.; Smith, C. R.; Mikolajczak, J. R.; Mikolajczak, K. L (1961). Characterization of Cyclopropenoid Acids in Selected Seed Oils. J. Am. Oil Chem. Soc. 38: 696-699.
[3] Johnson, A. R.; Pearson, J. A.; Shenstone, F. S.; Fogerty, A. C.; Giovanelli, J (1965). The Biosynthesis of Cyclopropane and Cyclopropene Fatty Acids in Plant Tissues. Lipids. 2: 308-315.
[4] Schneider, E. L.; Loke, S. P.; Hopkins, D. T (1968). Gas-Liquid Chromatographic Analysis of Cyclopropenoid Fatty Acids. J. Am. Oil Chem. Soc. 45: 585-590.
[5] Ralaimanarivo, A.; Gaydou, E. M.; Bianchini, J. P (1982). Fatty Acid Composition of Seed Oils from Six Adansonia Species with Particular Reference to Cyclopropane and Cyclopropropene Acids. Lipids. 17: 1-10.
[6] Obert, J. C.; Hughes, D.; Sorenson, W. R.; Mccann, M.; Ridley, W. P (2007). A Quantitative Method for the Determination of Cyclopropennoid Fatty Acids in Cottonseed Oil (Gossypium hirsutm) by High-Performance Lquid Chromatography. J. Agric. Food Chem. 55: 2062-2067.
[7] Standard Methods for the Analysis of Fats, Oils and Related Materials. (2013) Differential Method 2.1.1, Japan Oil Chemists Society.
[8] Horn, P. J.; Ledbetter, N. R.; James, C. N.; Hoffman, W. D.; Case, C. R.; Verbeck, G. F.; Chapman, K. D (2011). Visualization of Lpid Droplet Composition by Direct Organelle Mass Spectrometry. J Biol Chem. 286: 3298-3306.
[9] Bland, J. M.; Conkerton, E. J.; Abraham, G (1991). Triacylglyceride Composition of Oil by HPLC and GC. J. Am. Oil Chem. Soc. 68: 840-843.
[10] Hirayama, S.; Matsuda, T.; Izumi, Y (2015). Analysis of Triacylglycerol by Frit-FAB/LCMS. Chromatography. 36: 133-138.
Cite This Article
  • APA Style

    Shuji Hirayama, Daichi Shinozaki, Yoshiya Izumi. (2020). LC/MS Analysis of Cyclo Fatty Acid-containing Triacylglycerols in Cottonseed Oil. Science Journal of Analytical Chemistry, 8(1), 12-17. https://doi.org/10.11648/j.sjac.20200801.13

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    ACS Style

    Shuji Hirayama; Daichi Shinozaki; Yoshiya Izumi. LC/MS Analysis of Cyclo Fatty Acid-containing Triacylglycerols in Cottonseed Oil. Sci. J. Anal. Chem. 2020, 8(1), 12-17. doi: 10.11648/j.sjac.20200801.13

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    AMA Style

    Shuji Hirayama, Daichi Shinozaki, Yoshiya Izumi. LC/MS Analysis of Cyclo Fatty Acid-containing Triacylglycerols in Cottonseed Oil. Sci J Anal Chem. 2020;8(1):12-17. doi: 10.11648/j.sjac.20200801.13

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  • @article{10.11648/j.sjac.20200801.13,
      author = {Shuji Hirayama and Daichi Shinozaki and Yoshiya Izumi},
      title = {LC/MS Analysis of Cyclo Fatty Acid-containing Triacylglycerols in Cottonseed Oil},
      journal = {Science Journal of Analytical Chemistry},
      volume = {8},
      number = {1},
      pages = {12-17},
      doi = {10.11648/j.sjac.20200801.13},
      url = {https://doi.org/10.11648/j.sjac.20200801.13},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjac.20200801.13},
      abstract = {We measured the constituent triacylglycerol of cotton oil, the only edible oil containing a cyclo fatty acid. Due to the difficulty of obtaining a standard for triacylglycerols containing cyclo fatty acids, cotton oil is analyzed using cyclo triacylglycerol in kapok oil as a reference. Analytical methods used liquid chromatography fast atom bombardment mass spectrometry (LC / FAB-MS) using a matrix of 3% m-NBA containing 3 mM NaCl, and orthogonal transfer method for APCI / TOF-MS. FAB mass spectral properties of triacylglycerols containing cyclo fatty acids can be observed with [M + Na]+, [M-1]+ molecular ions, and [M- (RCOO)] + fragments. In the orthogonal APCI / TOF-MS spectrum, only the [M-1] + molecular ion appears, so that the presence of triacylglycerol containing CPFA becomes apparent. On the other hand, chain triacylglycerol can be observed as [M + 1]+ molecular ions and [M- (RCOO)]+ fragments. Based on these observations, triacylglycerols containing ten types of cyclo fatty acids were successfully successfully detected in crude cottonseed oil. In addition, the APCI/TOF-MS technique successfully detected dilinoleoyl-marvalyl-glycerol and palmtoyl-linoleoyl-marvalyl glycerol in the purified cottonseed oil.},
     year = {2020}
    }
    

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  • TY  - JOUR
    T1  - LC/MS Analysis of Cyclo Fatty Acid-containing Triacylglycerols in Cottonseed Oil
    AU  - Shuji Hirayama
    AU  - Daichi Shinozaki
    AU  - Yoshiya Izumi
    Y1  - 2020/01/31
    PY  - 2020
    N1  - https://doi.org/10.11648/j.sjac.20200801.13
    DO  - 10.11648/j.sjac.20200801.13
    T2  - Science Journal of Analytical Chemistry
    JF  - Science Journal of Analytical Chemistry
    JO  - Science Journal of Analytical Chemistry
    SP  - 12
    EP  - 17
    PB  - Science Publishing Group
    SN  - 2376-8053
    UR  - https://doi.org/10.11648/j.sjac.20200801.13
    AB  - We measured the constituent triacylglycerol of cotton oil, the only edible oil containing a cyclo fatty acid. Due to the difficulty of obtaining a standard for triacylglycerols containing cyclo fatty acids, cotton oil is analyzed using cyclo triacylglycerol in kapok oil as a reference. Analytical methods used liquid chromatography fast atom bombardment mass spectrometry (LC / FAB-MS) using a matrix of 3% m-NBA containing 3 mM NaCl, and orthogonal transfer method for APCI / TOF-MS. FAB mass spectral properties of triacylglycerols containing cyclo fatty acids can be observed with [M + Na]+, [M-1]+ molecular ions, and [M- (RCOO)] + fragments. In the orthogonal APCI / TOF-MS spectrum, only the [M-1] + molecular ion appears, so that the presence of triacylglycerol containing CPFA becomes apparent. On the other hand, chain triacylglycerol can be observed as [M + 1]+ molecular ions and [M- (RCOO)]+ fragments. Based on these observations, triacylglycerols containing ten types of cyclo fatty acids were successfully successfully detected in crude cottonseed oil. In addition, the APCI/TOF-MS technique successfully detected dilinoleoyl-marvalyl-glycerol and palmtoyl-linoleoyl-marvalyl glycerol in the purified cottonseed oil.
    VL  - 8
    IS  - 1
    ER  - 

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Author Information
  • Biomaterial in Tokyo Co., Ltd., Tokyo, Japan

  • Biomaterial in Tokyo Co., Ltd., Tokyo, Japan

  • Biomaterial in Tokyo Co., Ltd., Tokyo, Japan

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