ChemInform Abstract: Carotenoids and Related Polyenes. Part 7. Total Synthesis of Crassostreaxanthin B Applying the Stereoselective Rearrangement of Tetrasubstituted Epoxides.

Tode, Chisato; Yamano, Yumiko; Ito, Masayoshi

doi:10.1002/chin.200215190

Cited by 3 publications

(6 citation statements)

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“…Tode et al demonstrated that crassostreaxanthin B could be converted from halocynthiaxanthin by bio-mimetic chemical reactions [22,23]. Further studies of carotenoids in marine animals revealed that crassostreaxanthin A, crassostreaxanthin B, and their 3-acetates were widely distributed in marine bivalves [16,17].…”

Section: Mollusca (Mollusks)mentioning

confidence: 99%

“…Other metabolites of fucoxanthin, crasssostreaxanthin A ( 35 ) and crassostreaxanthin B ( 36 ), were isolated from the Japanese oyster Crassostrea gigas [ 21 ]. Tode et al demonstrated that crassostreaxanthin B could be converted from halocynthiaxanthin by bio-mimetic chemical reactions [ 22 , 23 ]. Further studies of carotenoids in marine animals revealed that crassostreaxanthin A, crassostreaxanthin B, and their 3-acetates were widely distributed in marine bivalves [ 16 , 17 ].…”

Section: Mollusca (Mollusks)mentioning

confidence: 99%

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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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Section: Mollusca (Mollusks)mentioning

confidence: 99%

Section: Mollusca (Mollusks)mentioning

confidence: 99%

Carotenoids in Marine Animals

2011

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“…Typically, the oxidation of alkenes proceeds in two directions: (1) the formation of allylic hydro peroxide, which further reacts to form allyl alcohol with the transposition of a double bond and the removal of an allylic hydrogen (Cainelli & Cardillo, ), (Tode C. et al, ); and (2) the formation of cyclic epoxide (Fenical, Kearns, & Radlick, ), which further reacts to cause the cleavage of carbon double bonds. Since BC involved cleavage of carbo‐carbon double bonds (Alija, Bresgen, Sommerburg, Siems, & Eckl, ), the formation of polyene epoxide in direction (2) should be the major process in BC degradation (Kennedy & Liebler, ).…”

Section: Resultsmentioning

confidence: 99%

Identification of Beta‐Carotene Degradation Compounds and Their Structural Elucidation by High‐Resolution Accurate Mass Spectrometry

Xu¹,

Butt²

2019

Journal of Food Science

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Beta-carotene (BC) degradation was studied by liquid chromatography coupled to a quadrupole time of flight mass spectrometer. Throughout/After 21 days of dark storage, 56 nonvolatile degradants were chromatographically separated from pure BC crystal and their molecular formulas were identified. Their structure information was gained by comparing the fragments to a different, but structure-related compound. For example, a newly formed double bond position in dehydrogenated BC was determined by comparing the fragments between BC and dehydrogenated BC. One of their chemical structures was confirmed by comparing its precursor ion mass, retention time, isotopic ratio, and fragmentation to a pure trans-beta-apo-8 -apocarotenal. BC cleavage was observed on double bonds as well as single bonds in BC conjugation chain.Practical Application: As evidenced in this study, beta-carotene (BC) degradation is a spontaneous process initiated when the compound is exposed to air. The stoichiometric ratio of BC to oxygen is 1:0.03 at the first oxidation, therefore, only 0.3 mg oxygen or 1.2 mL air will degrade 10 mg BC, an average daily recommended intake. Not like in enzymatic BC degradation, spontaneous BC oxidation did not produce provitamin A, either in retina C20H38O or retinol C20H40O forms. For BC application in vitamin A deficiency, spontaneous BC oxidation should be avoided.

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“…From the structural similarity, they are also assumed to be metabolites of halocynthiaxanthin (Figure ). Furthermore, Tode et al , demonstrated that the crassostreaxanthin B could be converted from halocynthiaxanthin by biomimetic chemical reactions.…”

Section: Resultsmentioning

confidence: 99%

“…Identification and Characterization of Carotenoids. β-Carotene (1), fucoxanthin (2), fucoxanthinol (4), crassostreaxanthin A ( 6), crassostreaxanthin B (8), halocynthiaxanthin (10), halocynthiaxanthin 3 0 -acetate (11), alloxanthin (12), diatoxanthin (13), diatoxanthin 3,6-epoxide (14), diadinoxanthin (15), and heteroxanthin (16) were identified on the basis of UV/vis, 1 H NMR, and FAB-MS data (7)(8)(9)(10)(11) and chromatographic behavior with our authentic samples obtained from the oyster Crassostrea gigas (7, 8), Corubicla japonica (9, 10), and Mactra chinensis (11).…”

Section: Methodsmentioning

confidence: 99%

Carotenoids in Clams, Ruditapes philippinarum and Meretrix petechialis

Maoka

Akimoto

Murakoshi

et al. 2010

J. Agric. Food Chem.

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Carotenoids were investigated in two species of clams, Rudiapes philippinarum and Meretrix petechialis. Fucoxanthin 3-esters and fucoxanthinol 3-esters were found to be major components, along with crassostreaxanthin A 3-acetate, crassostreaxanthin A, crassostreaxanthin B 3-acetate, crassostreaxanthin B, halocynthiaxanthin 3'-acetate, halocynthiaxanthin, alloxanthin, diatoxanthin, diadinoxanthin, and heteroxanthin. Fatty acids esterified with fucoxanthin and fucoxanthinol were identified as C24:6, C22:5, C22:6, C20:5, C20:0, C20:1, C18:0, C18:1, C16:0, C16:1, and C14:0 from fast atom bombardment-mass spectrometry (FAB-MS) data. Crassostreaxanthin A 3-acetate and crassostreaxanthin B 3-acetate were first isolated and completely characterized by spectroscopic data. Furthermore, possible metabolic pathways of fucoxanthin in clams were proposed.

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ChemInform Abstract: Carotenoids and Related Polyenes. Part 7. Total Synthesis of Crassostreaxanthin B Applying the Stereoselective Rearrangement of Tetrasubstituted Epoxides.

Cited by 3 publications

References 1 publication

Carotenoids in Marine Animals

Carotenoids in Marine Animals

Identification of Beta‐Carotene Degradation Compounds and Their Structural Elucidation by High‐Resolution Accurate Mass Spectrometry

Carotenoids in Clams, Ruditapes philippinarum and Meretrix petechialis

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