ISOLATION AND IDENTIFICATION OF 9-cis ASTAXANTHIN BY HPLC, FT-IR, AND NMR SPECTRA
Abstract
This study aims to perform a detailed qualitative analysis of astaxanthin isomers. A rapid, open column chromatography method was developed to separate astaxanthin geometrical isomers in gram-scale levels. Chromatographic separation was performed using two silica gel columns with dichloromethane/nhexane/diethyl ether (2:1:1, v/v/v) as elution system. The isolated isomers were identified as all-trans, 9-cis, 13-cis, and 15-cis astaxanthin, according to previously reported C30 high-performance liquid chromatography (HPLC) analysis data. Further, the fine structure of the single 9-cis astaxanthin isomer, as well as all-trans astaxanthin, was determined successfully for the first time by Fourier-transform infrared spectroscopy (FT-IR), one-dimensional 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, and twodimensional homonuclear correlation and heteronuclear correlation NMR spectroscopy.
Supporting agencies: This work is funded by Natural Science Foundation of China (51703100), Ningbo Natural Science Foundation (2018A610098), and Zhejiang Public Welfare Fund (LGN18B060002).
About the Authors
Y. Wang
School of Materials and Chemical Engineering at Ningbo University of Technology
China
China
Ningbo 315211
Y. Wu
Zhejiang NVB Co. Ltd.
China
High-Tech Industry Zone, XinChang 312500
China
High-Tech Industry Zone, XinChang 312500
T. Wang
School of Materials and Chemical Engineering at Ningbo University of Technology
China
China
Ningbo 315211
D. Qiu
School of Materials and Chemical Engineering at Ningbo University of Technology;
Zhejiang NVB Co. Ltd.
China
China
Ningbo 315211;
High-Tech Industry Zone, XinChang 312500
References
1. M. Guerin, M. E. Huntley, M. Olaizola, Trends Biotechnol., 21, 210–216 (2003).
2. M. Cianci, P. J. Rizkallah, A. Olczak, J. Raftery, N. E. Chayen, P. F. Zagalsky, J. R. Helliwell, Proc. Nat. Acad. Sci. USA, 99, 9795–9800 (2002).
3. Y. M. Naguib, J. Agric. Food Chem., 48, 1150–1154 (2000).
4. G. Hussein, U. Sankawa, H. Goto, K. Matsumoto, H. Watanabe, J. Nat. Prod., 69, 443–449 (2006).
5. N. Shimidzu, M. Goto, W. Miki, Fisheries Sci., 62, 134–137 (1996).
6. H. Jyonouchi, S. Sun, K. Iijima, M. D. Gross, Nutr. Cancer., 36, 59–65 (2000).
7. H. Kurihara, H. Koda, S. Asami, Y. Kiso, T. Tanaka, Life Sci., 70, 2509–2520 (2002).
8. L. Zhang, H. Wang, Mar. Drugs, 13, 4310–4330 (2015).
9. R. G. Fassett, J. S. Coombes, Mar. Drugs, 9, 447–465 (2011).
10. R. G. Fassett, J. S. Coombes, Future Cardiol., 5, 333–342 (2009).
11. H. Wu, H. Niu, A. Shao, C. Wu, B. Dixon, J. Zhang, S. Yang, Y. Wang, Mar. Drugs, 13, 5750–5766 (2015).
12. X. Liu, T. Osawa, Biochem. Biophy. Res. Commun., 357, 187–193 (2007).
13. B. Bjerkeng, M. Følling, S. Lagocki, T. Storebakken, J. J. Olli, N. Alsted, Aquaculture, 157, 63–82 (1997).
14. J. P. Yuan, F. Chen, J. Agric. Food Chem., 47, 3656–3660 (1999).
15. J. P. Yuan, F. Chen, Food Chem., 73, 131–137 (2001).
16. W. J. De Bruijn, Y. Weesepoel, J. P. Vincken, H. Gruppen, Food Chem., 194, 1108–1115 (2016).
17. A. Mortensen, L. H. Skibsted, J. Agric. Food Chem., 48, 279–286 (2000).
18. C. S. Chen, S. H. Wu, Y. Y. Wu, J. M. Fang, T. H. Wu, Org. Lett., 9, 2985–2988 (2007).
19. L. Zhao, F. Chen, G. Zhao, Z. Wang, X. Liao, X. Hu, J. Agric. Food Chem., 53, 9620–9623 (2005).
20. G. Euglert, M. Vecchi, Helv. Chim. Acta, 63, 1711–1718 (1980).
21. D. Qiu, W. L. Zhu, C. K. Tang, L. F. Shi, H. Q. Gao, Food Anal. Methods, 7, 597–605 (2014).
22. D. Qiu, Y. C. Wu, W. L. Zhu, H. Yin, L. T. Yi, J. Food Sci., 77, C934–C940 (2012).
23. M. D. Grynbaum, P. Hentschel, K. Putzbach, J. Rehbein, M. Krucker, G. Nicholson, K. Albert, J. Sep. Sci., 28, 1685–1693 (2005).
24. F. Miao, D. Lu, Y. Li, M. Zeng, Anal. Biochem., 352, 176–181 (2006).
25. D. Qiu, Y. Bai, Y. C. Shi, Food Chem., 135, 665–671 (2012).
26. K. Holtin, M. Kuehnle, J. Rehbein, P. Schuler, G. Nicholson, K. Albert, Anal. Bioanal. Chem., 395, 1613 (2009).
27. R. N. Rao, S. N. Alvi, B. N. Rao, H. Group, J. Chromatogr. A, 1076, 189–192 (2005).
28. W. Sun, H. Lin, Y. Zhai, L. Cao, K. Leng, L. Xing, Sep. Sci. Technol., 50, 1377–1383 (2015).
29. G. Britton, S. Liaaen-Jensen, H. Pfander, Carotenoids, Vol. 1B: Spectroscopy, Birkhäuser (1994).
30. R. J. Anderson, D. J. Bendell, P. W. Groundwater, Organic Spectroscopic Analysis, Royal Soc. Chem. (2004).
31. K. Pihlaja, E. Kleinpeter, Carbon-13 NMR Chemical Shifts in Structural and Stereochemical Analysis, John Wiley and Sons (1994).
32. N. Kumar, S. R. Devineni, G. Singh, A. Kadirappa, S. K. Dubey, P. Kumar, J. Pharm. Biomed., 119, 114–121 (2016).
Review
For citations:
Wang Y., Wu Y., Wang T., Qiu D. ISOLATION AND IDENTIFICATION OF 9-cis ASTAXANTHIN BY HPLC, FT-IR, AND NMR SPECTRA. Zhurnal Prikladnoii Spektroskopii. 2021;88(1):109-118.
Views: 377
Email this article 