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/n-hexane/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 chromato graphy (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 two-dimensional homonuclear correlation and heteronuclear correlation NMR spectroscopy.
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References
M. Guerin, M. E. Huntley, and M. Olaizola, Trends Biotechnol., 21, 210–216 (2003).
M. Cianci, P. J. Rizkallah, A. Olczak, J. Raftery, N. E. Chayen, P. F. Zagalsky, and J. R. Helliwell, Proc. Nat. Acad. Sci. USA, 99, 9795–9800 (2002).
Y. M. Naguib, J. Agric. Food Chem., 48, 1150–1154 (2000).
G. Hussein, U. Sankawa, H. Goto, K. Matsumoto, and H. Watanabe, J. Nat. Prod., 69, 443–449 (2006).
N. Shimidzu, M. Goto, and W. Miki, Fisheries Sci., 62, 134–137 (1996).
H. Jyonouchi, S. Sun, K. Iijima, and M. D. Gross, Nutr. Cancer., 36, 59–65 (2000).
H. Kurihara, H. Koda, S. Asami, Y. Kiso, and T. Tanaka, Life Sci., 70, 2509–2520 (2002).
L. Zhang and H. Wang, Mar. Drugs, 13, 4310–4330 (2015).
R. G. Fassett and J. S. Coombes, Mar. Drugs, 9, 447–465 (2011).
R. G. Fassett and J. S. Coombes, Future Cardiol., 5, 333–342 (2009).
H. Wu, H. Niu, A. Shao, C. Wu, B. Dixon, J. Zhang, S. Yang, and Y. Wang, Mar. Drugs, 13, 5750–5766 (2015).
X. Liu and T. Osawa, Biochem. Biophys. Res. Commun., 357, 187–193 (2007).
B. Bjerkeng, M. Følling, S. Lagocki, T. Storebakken, J. J. Olli, and N. Alsted, Aquaculture, 157, 63–82 (1997).
J. P. Yuan and F. Chen, J. Agric. Food Chem., 47, 3656–3660 (1999).
J. P. Yuan and F. Chen, Food Chem., 73, 131–137 (2001).
W. J. De Bruijn, Y. Weesepoel, J. P. Vincken, and H. Gruppen, Food Chem., 194, 1108–1115 (2016).
A. Mortensen and L. H. Skibsted, J. Agric. Food Chem., 48, 279–286 (2000).
C. S. Chen, S. H. Wu, Y. Y. Wu, J. M. Fang, and T. H. Wu, Org. Lett., 9, 2985–2988 (2007).
L. Zhao, F. Chen, G. Zhao, Z. Wang, X. Liao, and X. Hu, J. Agric. Food Chem., 53, 9620–9623 (2005).
G. Euglert and M. Vecchi, Helv. Chim. Acta, 63, 1711–1718 (1980).
D. Qiu, W. L. Zhu, C. K. Tang, L. F. Shi, and H. Q. Gao, Food Anal. Methods, 7, 597–605 (2014).
D. Qiu, Y. C. Wu, W. L. Zhu, H. Yin, and L. T. Yi, J. Food Sci., 77, C934–C940 (2012).
M. D. Grynbaum, P. Hentschel, K. Putzbach, J. Rehbein, M. Krucker, G. Nicholson, and K. Albert, J. Sep. Sci., 28, 1685–1693 (2005).
F. Miao, D. Lu, Y. Li, and M. Zeng, Anal. Biochem., 352, 176–181 (2006).
D. Qiu, Y. Bai, and Y. C. Shi, Food Chem., 135, 665–671 (2012).
K. Holtin, M. Kuehnle, J. Rehbein, P. Schuler, G. Nicholson, and K. Albert, Anal. Bioanal. Chem., 395, 1613 (2009).
R. N. Rao, S. N. Alvi, B. N. Rao, and H. Group, J. Chromatogr. A, 1076, 189–192 (2005).
W. Sun, H. Lin, Y. Zhai, L. Cao, K. Leng, and L. Xing, Sep. Sci. Technol., 50, 1377–1383 (2015).
G. Britton, S. Liaaen-Jensen, and H. Pfander, Carotenoids, Vol. 1B: Spectroscopy, Birkhäuser (1994).
R. J. Anderson, D. J. Bendell, and P. W. Groundwater, Organic Spectroscopic Analysis, Royal Soc. Chem. (2004).
K. Pihlaja and E. Kleinpeter, Carbon-13 NMR Chemical Shifts in Structural and Stereochemical Analysis, John Wiley and Sons (1994).
N. Kumar, S. R. Devineni, G. Singh, A. Kadirappa, S. K. Dubey, and P. Kumar, J. Pharm. Biomed., 119, 114–121 (2016).
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Published in Zhurnal Prikladnoi Spektroskopii, Vol. 88, No.1, pp. 109–118, January–February, 2021.
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Wang, Y., Wu, Y., Wang, T. et al. Isolation and Identification of 9-cis Astaxanthin by HPLC, FT-IR, and NMR Spectra. J Appl Spectrosc 88, 97–107 (2021). https://doi.org/10.1007/s10812-021-01146-y
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DOI: https://doi.org/10.1007/s10812-021-01146-y