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Mar. Drugs 2018, 16(8), 275; https://doi.org/10.3390/md16080275

Degradation of Fucoxanthin to Elucidate the Relationship between the Fucoxanthin Molecular Structure and Its Antiproliferative Effect on Caco-2 Cells

Food Component Analysis Unit, Food Research Institute, National Agriculture and Food Research Organization, 2-1-12, Kannondai, Tsukuba, Ibaraki 305-8642, Japan
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Received: 18 July 2018 / Revised: 30 July 2018 / Accepted: 2 August 2018 / Published: 6 August 2018
(This article belongs to the Collection Marine Carotenoids)
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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. View Full-Text
Keywords: fucoxanthin; ozonolysis; apo-fucoxanthinone; Caco-2; antiproliferative effect fucoxanthin; ozonolysis; apo-fucoxanthinone; Caco-2; antiproliferative effect
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Komba, S.; Kotake-Nara, E.; Tsuzuki, W. Degradation of Fucoxanthin to Elucidate the Relationship between the Fucoxanthin Molecular Structure and Its Antiproliferative Effect on Caco-2 Cells. Mar. Drugs 2018, 16, 275.

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