A NEW MARINE CAROTENOID, MYTILOXANTHINONE FROM THE SEA SQUIRT, <i>HALOCYNTHIA RORETZI</i>

Matsuno, Takao; Ookubo, Masahiro

doi:10.1246/cl.1982.1605

Cited by 9 publications

(5 citation statements)

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“…Activated macrophages produce a large quantity of PGE 2 and NO, which causes a variety of inflammatory diseases, and the increased expression of COX-2 and iNOS are responsible for the production of PGE 2 and NO 11,12) . Therefore, the present results indicate that these carotenoids may exhibit anti-inflammatory effect through the down-regulation of the mRNA for COX-2 and iNOS as well as pro-inflammato- All-trans alloxanthin and all-trans diatoxanthin have been reported to be major carotenoids in H. roretzi 1,2) . Both carotenoids can be found in several algae such as the Cryptophyceae 27) and dinoflagellates 28) .…”

Section: Discussionmentioning

confidence: 52%

“…Marine organisms are known to contain many kinds of carotenoids with unique structures. For example, the sea squirt Halocynthia roretzi contains a number of carotenoids including halocynthiaxanthin, alloxanthin, diatoxanthin, mytiloxanthin and fucoxanthinol with allenic, acetylenic and epoxicide structures in the molecule 1,2) . Previous studies have shown that holocynthiaxanthin exhibits an antiproliferative effect on various tumor cells 3) , inhibition of reverse transcriptases of immunodeficiency viruses 4) , and suppression of both superoxide and nitric oxide generation 5) .…”

Section: Introductionmentioning

confidence: 99%

“…The structures of carotenoids isolated from H. roretzi were identified by UV-VIS spectra, ESI-MS, 1 H NMR and 13 C NMR ( ). The UV-VIS spectra were recorded with a Shimadzu U-240 spectrophotometer in diethyl ether (Et 2 O).…”

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Suppressive Effects of Alloxanthin and Diatoxanthin from Halocynthia roretzi on LPS-induced Expression of Pro-inflammatory Genes in RAW264.7 Cells

et al. 2008

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To investigate anti-inflammatory effects of carotenoids from Halocynthia roretzi, gene expression levels were measured for pro-inflammatory cytokines and enzymes in the murine macrophage-like cell line, RAW264.7, stimulated with lipopolysaccharide (LPS). All-trans alloxanthin, all-trans diatoxanthin, and their 9-cis isomers isolated from H. roretzi significantly suppressed expression of IL-1b and IL-6 mRNA in cells induced by LPS without cytotoxicity. The expression level of IL-1b mRNA in cells treated with 25 mM all-trans alloxanthin for 24 h, followed by stimulation with 0.1 mg/mL LPS for 24 h in the presence of carotenoid decreased to 33.7±3.0% from that of control cells stimulated with LPS alone. All-trans diatoxanthin, 9-cis alloxanthin and 9-cis diatoxanthin also decreased expression of IL-1b mRNA to 25.1±2.1, 28.2±0.9 and 32.9±3.3%, respectively, from that of control cells stimulated with LPS. IL-1b production in culture medium was also suppressed by all-trans alloxanthin and all-trans diatoxanthin. Furthermore, all-trans alloxanthin, all-trans diatoxanthin and their 9-cis isomers suppressed the overexpression of cyclooxygenase-2 and nitric oxide synthase mRNA in RAW264.7 cells induced by LPS. The suppressive effects of these carotenoids were remarkable compared to those of b-carotene and zeaxanthin.

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Section: Discussionmentioning

confidence: 52%

Section: Introductionmentioning

confidence: 99%

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Suppressive Effects of Alloxanthin and Diatoxanthin from Halocynthia roretzi on LPS-induced Expression of Pro-inflammatory Genes in RAW264.7 Cells

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“…These carotenoids were designated as amarouciaxanthin A and B, referring to Amaroucium from which the carotenoids were isolated. It is very interesting from a biosynthetic point of view that A. pliciferum possesses high contents of amarouciaxanthin A (3) and B (4) (See Results section).…”

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confidence: 99%

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

Matsuno¹,

Ookubo²,

Komori³

1985

J. Nat. Prod.

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The structure of two new marine carotenoids, isolated from the tunicate, Amaroucium pliciferum, and designated as amarouciaxanthin A and B, were determined on the basis of chemical and spectral data. Amarouciaxanthin A was determined as (6S, 3'S, 5'R,6'R)- 6,3',5'-trihydroxy-4,5,6',7'-tetradehydro-7,8,5',6'-tetrahydro-beta, beta-carotene-3,8-dione, and Amarouciaxanthin B was determined as (6S,3'R)-6,3'-dihydroxy-4,5,7',8'-tetradehydro-7,8-dihydro-beta,beta- carotene-3,8-dione. These two compounds are also presumed to be new metabolic products of a typical marine carotenoid, fucoxanthin.

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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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A NEW MARINE CAROTENOID, MYTILOXANTHINONE FROM THE SEA SQUIRT, HALOCYNTHIA RORETZI

Abstract: A new marine carotenoid, mytiloxanthinone (3,8′-dihydroxy-7,8-didehydro-β,κ-carotene-3′,6′-dione) has been isolated from sea squirt, Halocynthia roretzi.

Cited by 9 publications

References 3 publications

Suppressive Effects of Alloxanthin and Diatoxanthin from Halocynthia roretzi on LPS-induced Expression of Pro-inflammatory Genes in RAW264.7 Cells

Suppressive Effects of Alloxanthin and Diatoxanthin from Halocynthia roretzi on LPS-induced Expression of Pro-inflammatory Genes in RAW264.7 Cells

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

Absorption and Metabolism of Xanthophylls

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