Mechanism and Effective Factors of Acyl Migration of Lysophospholipid

doi:10.6023/cjoc201404019

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (12): 2529-2536.DOI: 10.6023/cjoc201404019 Previous Articles Next Articles

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溶血磷脂酰基转移机理及有效影响因子研究

张康逸^a,b, 张丽霞^b, 屈凌波^a, 王兴国^c, 刘元法^c

a. 郑州大学化学系郑州 450001;
b. 河南省农科院农副产品加工研究所郑州 450002;
c. 江南大学食品学院无锡 214122

收稿日期:2014-04-12 修回日期:2014-07-14 发布日期:2014-08-26
通讯作者: 刘元法 E-mail:yuanfa.liu@gmail.com
基金资助:
国家自然科学基金(No.31301502)、河南省重大攻关(No.132102110066)和河南省农业科学院优秀青年科技基金(No.2013YQ25)资助项目.

Mechanism and Effective Factors of Acyl Migration of Lysophospholipid

Zhang Kangyi^a,b, Zhang Lixia^b, Qu Lingbo^a, Wang Xingguo^c, Liu Yuanfa^c

a. Department of Chemistry, Zhengzhou University, Zhengzhou 450001;
b. Henan Academy of Agricultural Sciences Institute of Agricultural Products Processing, Zhengzhou 450002;
c. Jiangnan University School of Food Science and Technology, Wuxi 214122

Received:2014-04-12 Revised:2014-07-14 Published:2014-08-26
Supported by:
Project supported by the National Natural Science Foundation of China (No. 31301502), the Key Science and Technology Program of Henan Province (No. 132102110066) and the Special Foundation for Young Scientists of Henan Academy of Agricultural Sciences (No. 2013YQ25).

The specificity hydrolysis Sn-1 fatty acyl of phospholipids by phospholipase A₁ and the phenomenon of acyl migration in Sn-2-lysophosphatidylcholine (Sn-2-LPC) were demonstrated through ¹³C NMR, which provided fundamental basis for enzymatic reaction solution of phosphatidylcholine (PC) including Sn-1-lysophosphatidylcholine, Sn-2-LPC, and L-α-glycerylphosphorylcholine. Based on the automatic acyl migration mechanism of monoglycerides, the automatic acyl migration mechanism of Sn-2-LPC was speculated in the acid condition or alkali condition. The effects of reaction parameters on the acyl migration were then explored, including the polarity of the solution, pH, temperature, substrate concentration, and reaction time. The conditions of low acyl migration were as follows: isopropanol solvent, pH 7～8, temperature<35 ℃, defined substrate concentration, shorten reaction time. These results contributed to a data support for the synthesis of acyl mixture of phospholipids, detection of specific phospholipase A₁, and the explanation of biosynthetic pathway (lysophospholipid intermediate) of the production mixed phospholipid.

Key words: lysophospholipid, acyl migration, mechanism, effective factors

Cite this article

Zhang Kangyi, Zhang Lixia, Qu Lingbo, Wang Xingguo, Liu Yuanfa. Mechanism and Effective Factors of Acyl Migration of Lysophospholipid[J]. Chin. J. Org. Chem., 2014, 34(12): 2529-2536.

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[1] Hu, M.-P.; Zhang, D.-J.; Zhang A.-W.; Lu, B.-X.; Li, J.-Y.; Huai, B.-D. China Oils Fats 2012, 37(11), 61 (in Chinese). (胡铭畔, 张东杰, 张爱武, 鹿保鑫, 李靖元, 怀宝东, 中国油脂, 2012, 37(11), 61.)
[2] Peng, L.-F.; Xu, X.-B.; Mu, H.-L.; Hoy, C.; Adler-Nissen, J. Enzyme Microb. Technol. 2002, 31(4), 523.
[3] Saubhi, S.; Wang, Z.; Russell, T.; Xu. Y. Semin. Cell Dev. Biol. 2004, 15(5), 503.
[4] Tigyi, G. Biochim. Biophys. Acta, Mol. Cell Biol. Lipids 2013, 1831, 1.
[5] Raynal, P.; Montagner, A.; Dance, M.; Yart, A. Pathol. Biol. 2005, 53(1), 57.
[6] Slizyte, R.; Rustad, T.; Storro, I. Process Biochem. 2005, 40, 3680.
[7] Kie?bowicz, G.; G?adkowski, W.; Chojnacka, A.; Wawrzeńczyk, C. Food Chem. 2012, 135(4), 2542.
[8] Ponpipom, M. M.; Bugianesi, R. L. J. Lipid Res. 1980, 21(1), 136.
[9] Larrabee, A. L. Biochemistry 1979, 18(5), 3321.
[10] Liu, N.; Wang, Y.; Zhao, Q.-Z.; Cui, C.; Fu, M.; Zhao, M. Food Chem. 2012, 134(1), 301.
[11] Kie?bowicz, G.; Smuga, D.; G?adkowski, W.; Chojnacka, A.; Wawrzeńczyk, C. Talanta 2012, 94, 22.
[12] Dos Santos, J. C. S.; Garcia-Galan, C.; Rodrigues, R. C.; de Sant Ana, H. B.; Goncalves, L. R. B.; Fermandez-Lafuente, R. Enzyme Microb. Technol. 2014, 60, 1.
[13] Gupta, C. M.; Radhakrishnan, R.; Khorana, H. G. Proc. Natl. Acad. Sci. U. S. A. 1977, 74(10), 4315.
[14] Warner, T. G.; Benson, A. A. J. Lipid Res. 1977, 18(4), 548.
[15] Van Den Bosch, H.; Van Golde, L. M. G.; Slotboom, A. J.; Van Deenen, L. L. M. Biochim. Biophys. Acta 1968, 152(4), 694.
[16] Homma, H.; Nishijima, M.; Kobayashi, T.; Okuyama, H.; Nojima, S. Biochim. Biophys. Acta 1981, 663(1), 1.
[17] Fischer, E. Bet. Dtsch. Chem. Ges. 1920, 53(9), 1621.
[18] Serdarevich, B. J. Am. Oil Chem. Soc. 1967, 44(7), 381.
[19] Richmond, G. S.; Smith, T. K. Int. J. Mol. Sci. 2011, 12, 588.
[20] Ekroos, K.; Ejsing, C. S.; Bahr, U.; Karas, M.; Simons, K.; Shevchenko, A. J. Lipid Res. 2003, 44(8), 2182.
[21] Vikbjerg, A. F.; Mu, H.; Xu, X. J. Biotechnol. 2007, 128(3), 545.
[22] Poisson, L.; Devos, M.; Godet, S.; Ergan, F.; Pencrea?h, G. Biotechnol. Lett. 2009, 31(5), 743.
[23] Pliickthun, A.; Dennis, E. A. Biochemistry 1982, 21(8), 1743.
[24] Yang, T.; Fruekilde, M. B.; Xu, X. Food. Chem. 2005, 92(1), 101.
[25] Kodali, D. R.; Tercyak, A.; Fahey, D. A.; Small, D. M. Chem. Phys. Lipids 1990, 52(3～4), 163.
[26] Zhang, K. Y.; Liu, Y. F.; Wang, X. G. Eur. J. Lipid Sci. Technol. 2012, 114, 1254.

溶血磷脂酰基转移机理及有效影响因子研究

Mechanism and Effective Factors of Acyl Migration of Lysophospholipid

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