Abstract
Fucoxanthin has an antiproliferative effect on cancer cells, but its detailed structure–activity correlation has not yet been elucidated. To elucidate this correlation, fucoxanthin was degraded by ozonolysis. The degraded compounds of fucoxanthin obtained by ozonolysis were purified by HPLC and analyzed by NMR. The polyene chain of fucoxanthin was cleaved by ozonolysis, and the fucoxanthin was divided into two types of cyclohexyl derivatives, one with a β,γ-epoxy ketone group and the other with an allenic bond. In order to elucidate the structure–activity correlation, Caco-2 cells (human colorectal carcinoma) were treated with fucoxanthin degradation compounds. It was found that the entire structure of fucoxanthin is not essential for its antiproliferative effect and that even a partial structure exerts this effect.
Highlights
IntroductionFucoxanthin (1) is a xanthophyll-type carotenoid which is mainly distributed in brown algae [1,2,3,4,5,6,7,8,9,10].It has been reported that it has anticarcinogenic [11,12,13,14,15,16,17,18,19,20,21,22], anti-obesity [23,24,25], anti-inflammatory [26], anti-angiogenic [27], and antioxidative [28] effects
Its detailed structure–activity correlation has not been elucidated, regarding what kind of molecular structure of fucoxanthin is responsible for this activity
Fucoxanthin was purified from wakame (Undaria pinnatifida) (1.09 mg fucoxanthin/g dry wakame), as referenced in previous experiments [30]
Summary
Fucoxanthin (1) is a xanthophyll-type carotenoid which is mainly distributed in brown algae [1,2,3,4,5,6,7,8,9,10].It has been reported that it has anticarcinogenic [11,12,13,14,15,16,17,18,19,20,21,22], anti-obesity [23,24,25], anti-inflammatory [26], anti-angiogenic [27], and antioxidative [28] effects. Fucoxanthin (1) is a xanthophyll-type carotenoid which is mainly distributed in brown algae [1,2,3,4,5,6,7,8,9,10]. We focused on the anticarcinogenic activity of fucoxanthin. Its detailed structure–activity correlation has not been elucidated, regarding what kind of molecular structure of fucoxanthin is responsible for this activity. We decided to decompose a fucoxanthin molecule in order to elucidate the detailed structure–activity relationship and elucidate the mechanisms involved in its antiproliferative effect. By investigating the antiproliferative effect using each part of the degraded fucoxanthin, the structure contributing to the activity was able to be elucidated
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