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Research ArticleArticle

BIOTRANSFORMATION OF FUCOXANTHINOL INTO AMAROUCIAXANTHIN A IN MICE AND HEPG2 CELLS: FORMATION AND CYTOTOXICITY OF FUCOXANTHIN METABOLITES

Akira Asai, Tatsuya Sugawara, Hiroshi Ono and Akihiko Nagao
Drug Metabolism and Disposition February 2004, 32 (2) 205-211; DOI: https://doi.org/10.1124/dmd.32.2.205
Akira Asai
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Tatsuya Sugawara
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Hiroshi Ono
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Akihiko Nagao
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Abstract

Fucoxanthin, a major carotenoid in edible brown algae, potentially inhibits the proliferation of human prostate cancer cells via apoptosis induction. However, it has been postulated that dietary fucoxanthin is hydrolyzed into fucoxanthinol in the gastrointestinal tract before absorption in the intestine. In the present study, we investigated the further biotransformation of orally administered fucoxanthin and estimated the cytotoxicity of fucoxanthin metabolites on PC-3 human prostate cancer cells. After the oral administration of fucoxanthin in mice, two metabolites, fucoxanthinol and an unknown metabolite, were found in the plasma and liver. The unknown metabolite was isolated from the incubation mixture of fucoxanthinol and mouse liver preparation (10,000gsupernatant of homogenates), and a series of instrumental analyses identified it as amarouciaxanthin A [(3S,5R,6′S)-3,5,6′-trihydroxy-6,7-didehydro-5,6,7′,8′-tetrahydro-β,ϵ-carotene-3′,8′-dione]. The conversion of fucoxanthinol into amarouciaxanthin A was predominantly shown in liver microsomes. This dehydrogenation/isomerization of the 5,6-epoxy-3-hydroxy-5,6-dihydro-βend group of fucoxanthinol into the 6′-hydroxy-3′-oxo-ϵend group of amarouciaxanthin A required NAD(P)+ as a cofactor, and the optimal pH for the conversion was 9.5 to 10.0. Fucoxanthinol supplemented to culture medium via HepG2 cells was also converted into amarouciaxanthin A. The 50% inhibitory concentrations on the proliferation of PC-3 human prostate cancer cells were 3.0, 2.0, and 4.6 μM for fucoxanthin, fucoxanthinol, and amarouciaxanthin A, respectively. To our knowledge, this is the first report on the enzymatic dehydrogenation of a 3-hydroxyl end group of xanthophylls in mammals.

Footnotes

  • ↵1 Abbreviations used are: MTT, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide; VIS, visible absorption; MS, mass spectrometry; CD, circular dichroism; HPLC, high-performance liquid chromatography; LC/MS, liquid chromatography/mass spectrometry; APCI, atmospheric pressure chemical ionization; PBS, phosphate-buffered saline; DMSO, dimethyl sulfoxide;tR, retention time; SDR, short-chain dehydrogenase/reductase.

  • Supported in part by Special Coordination Funds of the Ministry of Education, Culture, Sports, Science and Technology, the Japan Government (to A.N.) and by Research Fellowships of the Japan Society for the Promotion of Science for Young Scientists (to A.A).

    • Received June 16, 2003.
    • Accepted October 1, 2003.
  • The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 32 (2)
Drug Metabolism and Disposition
Vol. 32, Issue 2
1 Feb 2004
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Research ArticleArticle

BIOTRANSFORMATION OF FUCOXANTHINOL INTO AMAROUCIAXANTHIN A IN MICE AND HEPG2 CELLS: FORMATION AND CYTOTOXICITY OF FUCOXANTHIN METABOLITES

Akira Asai, Tatsuya Sugawara, Hiroshi Ono and Akihiko Nagao
Drug Metabolism and Disposition February 1, 2004, 32 (2) 205-211; DOI: https://doi.org/10.1124/dmd.32.2.205

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Research ArticleArticle

BIOTRANSFORMATION OF FUCOXANTHINOL INTO AMAROUCIAXANTHIN A IN MICE AND HEPG2 CELLS: FORMATION AND CYTOTOXICITY OF FUCOXANTHIN METABOLITES

Akira Asai, Tatsuya Sugawara, Hiroshi Ono and Akihiko Nagao
Drug Metabolism and Disposition February 1, 2004, 32 (2) 205-211; DOI: https://doi.org/10.1124/dmd.32.2.205
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