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Marine Drugs  2012 

Anti-Oxidative, Anti-Tumor-Promoting, and Anti-Carcinogensis Activities of Nitroastaxanthin and Nitrolutein, the Reaction Products of Astaxanthin and Lutein with Peroxynitrite

DOI: 10.3390/md10061391

Keywords: carotenoid, 15-nitroastaxanthin, 15-nitrolutein, anti-carcinogensis activity, anti-oxidative activity

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Abstract:

Astaxanthin captured peroxynitrite to form nitroastaxanthins. 15-Nitroastaxanthin was a major reaction product of astaxanthin with peroxynitrite. Here, the anti-oxidative, anti-tumor-promoting, and anti-carcinogensis activities of 15-nitroastaxanthin were investigated. In addition to astaxanthin, 15-nitroastaxanthin showed excellent singlet oxygen quenching activity. Furthermore, 15-nitroastaxanthin showed inhibitory effects of in vitro Epstein-Barr virus early antigen activation and two-stage carcinogensis on mouse skin papillomas. These activities were slightly higher than those of astaxanthin. Similar results were obtained for the 15-nitrolutein, a major reaction product of lutein with peroxynitrite.

References

[1]  Maoka, T.; Etoh, H. Some Biological Functions of Carotenoids in Japanese Food. In Functional Foods of the East; Shi, J., Ho, C.-T., Shahidi, F., Eds.; CRC Press: Boca Raton, FL, USA, 2010; pp. 85–97.
[2]  Halliwell, B. Free radicals, antioxidants, and human disease: Curiosity, cause or consequence? Lancet 1994, 344, 721–724, doi:10.1016/S0140-6736(94)92211-X.
[3]  Lee, S.-J.; Bai, S.-K.; Lee, K.-S.; Namkoong, S.; Na, H.-J.; Ha, K.-S.; Han, J.-A.; Yim, S.-V.; Chang, K.; Kwon, Y.-G.; et al. Astaxanthin inhibits nitric oxide production and inflammatory gene expression by suppressing IκB kinase-dependent NF-κB activation. Mol. Cells 2003, 16, 97–105. 14503852
[4]  Yoshioka, R.; Hayakawa, T.; Ishizuka, K.; Kulkarni, A.; Terada, Y.; Maoka, T.; Etoh, H. Nitration reaction of astaxanthin and β-carotene by peroxynitrite. Tetrahedron Lett. 2006, 47, 3637–3640, doi:10.1016/j.tetlet.2006.03.139.
[5]  Hayakawa, T.; Kulkarni, A.; Terada, Y.; Maoka, T.; Etoh, H. Reaction of astaxanthin with peroxynitrite. Biosci. Biotechnol. Biochem. 2008, 72, 2716–2722, doi:10.1271/bbb.80358. 18838798
[6]  Tsuboi, M.; Etoh, H.; Yomoda, Y.; Kato, K.; Kato, H.; Kulkarni, A.; Terada, Y.; Maoka, T.; Mori, H.; Inakuma, T. Nitration reaction of lutein with peroxynitrite. Tetrahedron Lett. 2010, 51, 676–678, doi:10.1016/j.tetlet.2009.11.099.
[7]  Niwa, T.; Doi, U.; Kato, Y.; Osawa, T. Antioxidative properties of phenolic antioxidants isolated from corn steep liquor. J. Agric. Food Chem. 2001, 49, 177–182, doi:10.1021/jf0007885. 11170574
[8]  Kato, Y.; Ogino, Y.; Aoki, T.; Uchida, K.; Kawakishi, S.; Osawa, T. Phenolic antioxidants prevent peroxynitrite-derived collagen modification in vitro. J. Agric. Food. Chem. 1997, 45, 3004–3009, doi:10.1021/jf960865p.
[9]  Tsuda, T.; Kato, Y.; Osawa, T. Mechanism for the peroxynitrite scavenging activity by anthocyanins. FEBS Lett. 2000, 484, 207–210, doi:10.1016/S0014-5793(00)02150-5. 11078880
[10]  Goss, S.P.A.; Hogg, N.; Kalyanaraman, B. The effect of α-tocopherol on the nitration of γ-tocopherol by peroxynitrite. Arch. Biochem. Biophys. 1999, 363, 333–340, doi:10.1006/abbi.1998.1094. 10068456
[11]  Tuboi, M.; Etoh, H.; Kato, K.; Nakatsugawa, H.; Kato, H.; Maejima, Y.; Natsumoto, G.; Mori, H.; Hosokawa, M.; Miyashita, K.; et al. Nitrocapsanthin and nitrofucoxanthin, respective products of capsanthin and fucoxanthin reaction with peroxynitrite. J. Agric. Food Chem. 2011, 59, 10572–10578, doi:10.1021/jf203493k. 21899264
[12]  Groves, J.T.; Marla, S.S. Peroxynitrite-induced DNA stanrard scission mediated by a magnanese porphyrin. J. Am. Chem. Soc. 1995, 117, 9578–9579, doi:10.1021/ja00142a032.
[13]  Hirayama, O.; Nakamura, K.; Hamada, S.; Kobayashi, Y. Singlet oxygen quenching ability of naturally occurring carotenoids. Lipid 1994, 29, 149–150, doi:10.1007/BF02537155.
[14]  Kobayashi, M.; Sakamoto, Y. Singlet oxygen quenching ability of astaxanthin esters from the green alga Haematococcus pluvialis. Biotechnol. Lett. 1999, 21, 265–269, doi:10.1023/A:1005445927433.
[15]  Osawa, A.; Ishii, Y.; Sasamura, N.; Morita, M.; Kasai, H.; Maoka, T.; Shindo, K. Characterization and antioxidative activities of rare C50 carotenoids-sarcinaxanthin, sarcinaxanthin monoglucoside, and sarcinaxanthin diglucoside-obtained from Micrococcus yunnanensis. J. Oleo Sci. 2010, 59, 653–659, doi:10.5650/jos.59.653.
[16]  Miki, W. Biological functions and activities of animal carotenoids. Pure Appl. Chem. 1991, 63, 141–146, doi:10.1351/pac199163010141.
[17]  Shimidzu, N.; Goto, M.; Miki, W. Carotenoids as singlet oxygen quenchers in marine organisms. Fish. Sci. 1996, 62, 134–137, doi:10.2331/suisan.62.134.
[18]  Tsushima, M.; Maoka, T.; Katsuyama, M.; Kozuka, M.; Matsuno, T.; Tokuda, H.; Nishino, H.; Iwashima, A. Inhibitory effect of natural carotenoids on Epstein-Barr virus activation activity of a tumor promoter in Raji cells. A screening study for anti-tumor promoters. Biol. Pharm. Bull. 1995, 18, 227–233, doi:10.1248/bpb.18.227.
[19]  Maoka, T.; Mochida, K.; Kozuka, M.; Ito, Y.; Fujiwara, Y.; Hashimoto, K.; Enjo, F.; Ogata, M.; Nobukuni, Y.; Tokuda, H.; et al. Cancer chemopreventive activity of carotenoids in the fruits of red paprika Capsicum annuum L. Cancer Lett. 2001, 172, 103–109, doi:10.1016/S0304-3835(01)00635-8.

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