Isolation and Identification of Amarouciaxanthin A from the Bivalve Paphia euglypta (Sudaregai in Japanese)

Matsuno, Takao; Sakaguchi, S.; Ookubo, Masahiro; Maoka, Takashi

doi:10.2331/suisan.51.1909

Cited by 13 publications

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“…7. 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.…”

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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“…However, there are few reports on the carotenoids of Paphia clams. Only amarouciaxanthin A ester was reported in Paphia euglypta (Veneridae, Sudaregai in Japanese) . In the course of carotenoid studies in shellfish − , carotenoids in Paphia amabillis (Veneridae, Satsuma Akagai in Japanese) were investigated.…”

Section: Introductionmentioning

confidence: 99%

“…Only amarouciaxanthin A ester was reported in Paphia euglypta (Veneridae, Sudaregai in Japanese) (4). In the course of carotenoid studies in shellfish (4)(5)(6)(7)(8)(9), carotenoids in Paphia amabillis (Veneridae, Satsuma Akagai in Japanese) were investigated. Recently, amarouciaxnthin A 3′-ester (1a), amarouciaxnthin A (1b), fucoxanthinol 3-ester (2), peridininol 3′ester (3), and a new C 37 skeletal carotenoid, named hydratopyrrhoxanthinol 3′-ester (4), were isolated from the muscle of P. amabillis.…”

Section: Introductionmentioning

confidence: 99%

New C₃₇ Skeletal Carotenoid from the Clam, Paphia amabillis

Maoka

Akimoto

Yim

et al. 2008

J. Agric. Food Chem.

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Carotenoids in the muscle of Paphia amabillis (Veneridae) were investigated. Amarouciaxanthin 3-ester (1a) was found to be a major carotenoid along with amarouciaxanthin A (1b), fucoxanthinol 3-ester (2), peridininol 3'-ester (3), and a new C(37) skeletal carotenoid, named hydratopyrrhoxanthinol 3'-ester. This structure was determined to be 3'-acyloxy-3,5,6-trihydroxy-7',8'-didehydro-5,6-dihydro-12',13',20'-trinor-beta,beta-caroten-19,11-olide (4) by UV-vis, NMR, and FAB-MS spectral data. The absolute configuration of 4 was postulated to be (3S,5R,6R,3'R) on the bases of CD and ROESY data. The fatty acids esterified with hydratopyrrhoxanthinol were assigned as C22:6, C20:1, C20:4, C20:5, C18:0, C18:1, C17:0, C16:0, C16:1, and C14:0 on the basis of FAB-MS data.

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Britton

Liaaen‐Jensen

Pfander³

2004

Carotenoids

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Isolation and Identification of Amarouciaxanthin A from the Bivalve Paphia euglypta (Sudaregai in Japanese)

Cited by 13 publications

References 1 publication

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

New C₃₇ Skeletal Carotenoid from the Clam, Paphia amabillis

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Isolation and Identification of Amarouciaxanthin A from the Bivalve Paphia euglypta (Sudaregai in Japanese)

Cited by 13 publications

References 1 publication

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

New C37 Skeletal Carotenoid from the Clam, Paphia amabillis

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New C₃₇ Skeletal Carotenoid from the Clam, Paphia amabillis