Structure of New Carotenoids with a 3,4-Dihydroxy-.BETA.-End Group from the Oyster Crassostrea gigas

The characterization and structure of epoxy carotenoids possessing 5,6-epoxy, 5,8-epoxy and 3,6-epoxy end groups conjugated to the polyene chain were investigated using high-energy fast atom bombardment collision-induced dissociation MS/MS methods. In addition to [M - 80](+*), a characteristic fragment ion of an epoxy carotenoid, product ions resulting from the cleavage of C-C bonds in the polyene chain from the epoxy end group, such as m/z 181 (b ion) and 121 (c ion), were detected. On the other hand, diagnostic ions of m/z 286 (e-H ion) and 312 (f-H ion) were observed, not in the 5,6-epoxy or 5,8-epoxy carotenoid but in the 3,6-epoxy carotenoid. These fragmentation patterns can be used to distinguish 3,6-epoxy carotenoids from 5,6-epoxy or 5,8-epoxy carotenoids. The structure of an epoxy carotenoid, 3,6-epoxy-5,6-dihydro-7',8'-didehydro-beta,beta-carotene-5,3'-diol (8), isolated from oyster, was characterized using FAB CID-MS/MS by comparing fragmentation patterns with those of related known compounds.

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“…Details of the isolation and structural elucidation of 8 including an NMR study are reported in the literature (7).…”

Section: Methodsmentioning

confidence: 99%

Characterization of epoxy carotenoids by fast atom bombardment collision‐induced dissociation MS/MS

Maoka

Fujiwara

Hashimoto

et al. 2004

Lipids

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“…Furthermore, three mytiloxanthin analogues containing an allenic end group ( 29 ), a 3,6-epoxy-end group ( 30 ), and a 3,4-dihydroxy-β-end group ( 31 ) were isolated from the oyster [16,17]. Compound 29 , termed allenic mytiloxanthin, was assumed to be a metabolic intermediate from fucoxanthinol to mytiloxanthin.…”

Section: Mollusca (Mollusks)mentioning

confidence: 99%

“…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]. Moreover, two crassostreaxanthin A analogues, 37 and 38 , were isolated from the oyster as minor components [16,17].…”

Section: Mollusca (Mollusks)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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“…crassostreaxanthins A and B from Crassostrea gigas 9,10 ; fucoxanthin and fucoxanthinol esters from Mactra chinensis 11 , Ruditapes philippinarum, and Meretrix petechia 12 ; amarouciaxanthin A esters from Paphia amabillis 13 ; and a series of carotenoids with a 5,6-dihydro-β-end group from Fushinus perplexus 14 . However, there are few reports on the content of carotenoids in freshwater shellfi sh, and only the carotenoids of the corbicula clams Corbicula sandai and the Chinese corbicula clam have been investigated by modern spectroscopic methods 15 .…”

Section: Introductionmentioning

confidence: 99%

Identification of Carotenoids in the Freshwater Shellfish Unio douglasiae nipponensis, Anodonta lauta, Cipangopaludina chinensis laeta, and Semisulcospira libertina

et al. 2012

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Structure of New Carotenoids with a 3,4-Dihydroxy-.BETA.-End Group from the Oyster Crassostrea gigas

Cited by 21 publications

References 18 publications

Characterization of epoxy carotenoids by fast atom bombardment collision‐induced dissociation MS/MS

Characterization of epoxy carotenoids by fast atom bombardment collision‐induced dissociation MS/MS

Carotenoids in Marine Animals

Identification of Carotenoids in the Freshwater Shellfish Unio douglasiae nipponensis, Anodonta lauta, Cipangopaludina chinensis laeta, and Semisulcospira libertina

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