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

Takashi Maoka,Nobutaka Suzuki,Hideaki Kato,Hideo Etoh,Harukuni Tokuda

doi:10.3390/md10061391

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.

Highlights

Carotenoids have an excellent capacity to quench singlet oxygen (1O2) and inhibit lipid peroxidation
We assumed that astaxanthin and lutein could inhibit tyrosine nitration induced by peroxynitrite and that nitroastaxanthin and nitrolutein themselves may have 1O2 quenching and anti-carcinogensis activities
We investigated the inhibitory effect of tyrosine nitration with peroxynitrite by astaxanthin and lutein

Summary

Introduction

Carotenoids have an excellent capacity to quench singlet oxygen (1O2) and inhibit lipid peroxidation. They cannot scavenge superoxide anion radicals (O2−), hydroxy radicals (OH·), or hydrogen peroxide (H2O2). There have been few reports on scavenging and/or the reaction of reactive nitrogen species with carotenoids [1]. A major carotenoid in green algae and higher plants, showed radical scavenging, anti-carcinogenic, anti-diabetic, and anti-obesitic activities [1]. We assumed that astaxanthin and lutein could inhibit tyrosine nitration induced by peroxynitrite and that nitroastaxanthin and nitrolutein themselves may have 1O2 quenching and anti-carcinogensis activities. 1O2 quenching, anti-tumor-promoting, and anti-carcinogensis activities of 15-nitroastaxanthin and 15-nitrolutein (Figure 1), the major reaction products of astaxanthin and lutein with peroxynitrite, were studied

Inhibition of Tyrosine Nitration with Peroxynitrite by Astaxanthin and Lutein

Quenching Effects of 1O2 by 15-Nitroastaxanthin and 15-Nitrolutein

Inhibition of Tyrosine Nitration with Peroxynitrite by Carotenoids

Measurement of 1O2 Quenching Activity

Conclusions