Carotenoids of Tunicates, III. The Structural Elucidation of Two New Marine Carotenoids, Amarouciaxanthin A and B

Matsuno, Takao; Ookubo, Masahiro; Komori, Tadaaki

doi:10.1021/np50040a015

Cited by 47 publications

(41 citation statements)

References 12 publications

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“…Until now, amarouciaxanthin A has been found only in two marine invertebrates, a tunicate (A. pliciferum) (Matsuno et al, 1985a) and a bivalve (P. euglypta) (Matsuno et al, 1985b). From the structural similarity, Matsuno et al (1985a) hypothesized that amarouciaxanthin A would be one of the metabolites of fucoxanthin in A. pliciferum. However, there has been no experimental evidence for the conversion of fucoxanthin into amarouciaxanthin A.…”

Section: Discussionmentioning

confidence: 99%

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Biotransformation of Fucoxanthinol Into Amarouciaxanthin a in Mice and Hepg2 Cells: Formation and Cytotoxicity of Fucoxanthin Metabolites

et al. 2004

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This article is available online at http://dmd.aspetjournals.org 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 (10,000g supernatant of homogenates), and a series of instrumental analyses identified it as amarouciaxanthin A [(3S,5R,6S)-3,5,6-trihydroxy-6,7-didehydro-5,6,7,8-tetrahydro-␤,⑀-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-␤ end group of fucoxanthinol into the 6-hydroxy-3-oxo-⑀ end 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 M 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.

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Section: Discussionmentioning

confidence: 99%

“…at ASPET Journals on May 12, 2018 dmd.aspetjournals.org ciaxanthin A, which has been isolated from marine animals, a tunicate (Amaroucium pliciferum) (Matsuno et al, 1985a), and a bivalve (Paphia euglypta) (Matsuno et al, 1985b).…”

Section: Hepatic Conversion Of Fucoxanthinol Into Amarouciaxanthin Amentioning

confidence: 99%

Biotransformation of Fucoxanthinol Into Amarouciaxanthin a in Mice and Hepg2 Cells: Formation and Cytotoxicity of Fucoxanthin Metabolites

et al. 2004

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“…They are widely distributed in various tunicates. Amarouciaxanthin A ( 34 ) and amarouciaxanthin B ( 69 ), having a unique 3-oxo-6-hydroxy-ε-end group, were first isolated from the tunicate Amaroucium pliciferum [35] (Figure 12). Peridinin and its metabolites are also found in tunicates.…”

Section: Protochordata (Tunicates)mentioning

confidence: 99%

Carotenoids in Marine Animals

2011

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Marine animals contain various carotenoids that show structural diversity. These marine animals accumulate carotenoids from foods such as algae and other animals and modify them through metabolic reactions. Many of the carotenoids present in marine animals are metabolites of β-carotene, fucoxanthin, peridinin, diatoxanthin, alloxanthin, and astaxanthin, etc. Carotenoids found in these animals provide the food chain as well as metabolic pathways. In the present review, I will describe marine animal carotenoids from natural product chemistry, metabolism, food chain, and chemosystematic viewpoints, and also describe new structural carotenoids isolated from marine animals over the last decade.

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“…In addition to rodents, it has been reported that fucoxanthin is absorbed in other animals such as tunicates [37,38], chicken [39], and aquatic insects [40]. However, fucoxanthin was not absorbed in freshwater fish [40].…”

Section: Intestinal Absorption Of Xanthophyllsmentioning

confidence: 99%

Absorption and Metabolism of Xanthophylls

2011

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Dietary carotenoids, especially xanthophylls, have attracted significant attention because of their characteristic biological activities, including anti-allergic, anti-cancer, and anti-obese actions. Although no less than forty carotenoids are ingested under usual dietary habits, only six carotenoids and their metabolites have been found in human tissues, suggesting selectivity in the intestinal absorption of carotenoids. Recently, facilitated diffusion in addition to simple diffusion has been reported to mediate the intestinal absorption of carotenoids in mammals. The selective absorption of carotenoids may be caused by uptake to the intestinal epithelia by the facilitated diffusion and an unknown excretion to intestinal lumen. It is well known that β-carotene can be metabolized to vitamin A after intestinal absorption of carotenoids, but little is known about the metabolic transformation of non provitamin A xanthophylls. The enzymatic oxidation of the secondary hydroxyl group leading to keto-carotenoids would occur as a common pathway of xanthophyll metabolism in mammals. This paper reviews the absorption and metabolism of xanthophylls by introducing recent advances in this field.

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Carotenoids of Tunicates, III. The Structural Elucidation of Two New Marine Carotenoids, Amarouciaxanthin A and B

Cited by 47 publications

References 12 publications

Biotransformation of Fucoxanthinol Into Amarouciaxanthin a in Mice and Hepg2 Cells: Formation and Cytotoxicity of Fucoxanthin Metabolites

Biotransformation of Fucoxanthinol Into Amarouciaxanthin a in Mice and Hepg2 Cells: Formation and Cytotoxicity of Fucoxanthin Metabolites

Carotenoids in Marine Animals

Absorption and Metabolism of Xanthophylls

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