Isomer Separation of trans-Astaxanthin, 9-cis-Astaxanthin and 13-cis-Astaxanthin by Ligand Exchange Chromatography

Yu Ri Lee, Xiaoxia Li and Kyung Ho Row*

Department of Chemistry and Chemical Engineering, Inha University, 253 Yonghyun-Dong, Nam-gu, Incheon 402-701, Republic of Korea

*Corresponding author: E-mail: rowkho@inha.ac.kr

Abstract

The astaxanthin molecule has two geometric isomers, cis or trans on account of the double bond from the polyene chain. The separation of these isomers is quite difficult using ordinary techniques. The conditions of ligand exchange chromatography for stereoisomer separation were examined using an astaxanthin stereoisomer. A C18 column was used with a mobile phase consisting of an acetonitrile-chloroform-methanol chiral mobile phase additive solution (containing different concentrations of L-serine and copper sulfate) at flow rate of 0.5 mL/min. The effects of different kinds and concentrations of ligands, bivalent ligand ions and organic modifier were evaluated. The astaxanthin isomers could be obtained from heat-treating the astaxanthin standard, which were confirmed by the ultraviolet-visible and nuclear magnetic resonance spectroscopy.

Keywords

Astaxanthin, Carotenoid, Separation, Geometric isomer, Extraction.

Reference (25)

1.       I. Schmidt, H. Schewe, S. Gassel, C. Jin, J. Buckingham, M. Hümbelin, G. Sandmann and J. Schrader, J. Appl. Microbiol. Biotechnol., 89, 555 (2011); doi:10.1007/s00253-010-2976-6.

2.       H. Jyonouchi, S. Sun, K. Iijima and M.D. Gross, Nutr. Cancer, 36, 59 (2000); doi:10.1207/S15327914NC3601_9

3.       M. Guerin, M.E. Huntley and M. Olaizola, Trends Biotechnol., 21, 210 (2003); doi:10.1016/S0167-7799(03)00078-7

4.       K. Nakagawa, T. Kiko, T. Miyazawa, G. Carpentero Burdeos, F. Kimura, A. Satoh and T. Miyazawa, Br. J. Nutr., 105, 1563 (2011); doi:10.1017/S0007114510005398.

5.       J.P. Yuan and F. Chen, J. Agric. Food Chem., 47, 3656 (1999); doi:10.1021/jf981319u.

6.       L.M.J. Seabra and L.F.C. Pedrosa, Rev. Nutr., 23, 1041 (2010); doi:10.1590/S1415-52732010000600010.

7.       I. Higuera-Ciapara, L. Félix-Valenzuela and F.M. Goycoolea, Crit. Rev. Food Sci. Nutr., 46, 185 (2006); doi:10.1080/10408690590957188.

8.       X. Liu and T. Osawa, Biochem. Biophys. Res. Commun., 357, 187 (2007); doi:10.1016/j.bbrc.2007.03.120.

9.       A.P. Sánchez-Camargo, H.A. Martinez-Correa, L.C. Paviani and F.A. Cabral, J. Supercrit. Fluids, 56, 164 (2011); doi:10.1016/j.supflu.2010.12.009.

10.   F. Shahidi and J. Synowiecki, J. Agric. Food Chem., 39, 1527 (1991); doi:10.1021/jf00008a032.

11.   S.P. Meyers and D. Bligh, J. Agric. Food Chem., 29, 505 (1981); doi:10.1021/jf00105a017.

12.   K.L. Chiu, Y.C. Cheng, J.H. Chen, C.J. Chang and P.-W. Yang, J. Supercrit. Fluids, 24, 77 (2002); doi:10.1016/S0896-8446(02)00014-1.

13.   L. Wang, B. Yang, B. Yan and X. Yao, Food Sci. Emerg. Technol., 13, 120 (2012); doi:10.1016/j.ifset.2011.09.004.

14.   C.D. Kang and S.J. Sim, Biotechnol. Lett., 30, 441 (2008); doi:10.1007/s10529-007-9578-0.

15.   N.M. Sachindra and N.S. Mahendrakar, Bioresour. Technol., 96, 1195 (2005); doi:10.1016/j.biortech.2004.09.018.

16.   V.A. Davankov, J. Chromatogr. A, 1000, 891 (2003); doi:10.1016/S0021-9673(03)00304-2.

17.   M. Tian, H. Yan and K.H. Row, J. Chem. Technol. Biotechnol., 84, 1001 (2009); doi:10.1002/jctb.2123.

18.   N.E. Polyakov, A.L. Focsan, M.K. Bowman and L.D. Kispert, J. Phys. Chem. B, 114, 16968 (2010); doi:10.1021/jp109039v.

19.   S. Keunchkarian, C.A. Franca, L.G. Gagliardi and C.B. Castells, J. Chromatogr. A, 1298, 103 (2013); doi:10.1016/j.chroma.2013.05.030.

20.   M. Tian, H.S. Row and K.H. Row, Monatsh. Chem., 141, 285 (2010); doi:10.1007/s00706-010-0264-x.

21.   J.P. Yuan, J. Peng, K. Yin and J.H. Wang, Mol. Nutr. Food Res., 55, 150 (2011); doi:10.1002/mnfr.201000414.

22.   A.M. Krustulovic, Chiral Separations by HPLC, Ellis Horwood Limited: Chichester, p. 107 (1989).

23.   S. Gorog and M. Gazdag, J. Chromatogr. B Biomed. Appl., 659, 51 (1994); doi:10.1016/0378-4347(94)00124-3.

24.   P. Hentschel, M.D. Grynbaum, P. Molnar, K. Putzbach, J. Rehbein, J. Deli and K. Albert, J. Chromatogr. A, 1112, 285 (2006); doi:10.1016/j.chroma.2005.12.082.

25.   K. Holtin, M. Kuehnle, J. Rehbein, P. Schuler, G. Nicholson and K. Albert, Anal. Bioanal. Chem., 395, 1613 (2009); doi:10.1007/s00216-009-2837-2.

 

   View Article PDF File Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.