A Series of 19 '-Hexanoyloxyfucoxanthin Derivatives from the Sea Mussel, Mytilus galloprovincialis, Grown in the Black Sea, Ukraine

Research Institute for Production Development, 15 Shimogamo-morimoto-cho, Sakyo-ku, Kyoto 606-0805, Japan.
Journal of Agricultural and Food Chemistry (Impact Factor: 2.91). 11/2011; 59(24):13059-64. DOI: 10.1021/jf2035115
Source: PubMed


A series of carotenoids with 19- or 19'-hexanoyloxy moieties, 19'-hexanoyloxyfucoxanthin (1), 19'-hexanoyloxyfucoxanthinol (2), 19'-hexanoyloxyhalocynthiaxanthin (3), 19-hexanoyloxycrassostreaxanthin A (4), 19-hexanoyloxymytiloxanthin (5), and 19-hexanoyloxyallenicmytiloxanthin (6) were isolated from the edible part of the sea mussel, Mytilus galloprovincialis, grown in the Black Sea, Ukraine. Among them, 3, 4, and 6 were new compounds. These structures were charcterized by UV-vis, fast atom bombardment mass spectrometry, circular dichroism, and (1)H NMR spectroscopic data. They were assumed to be metabolites of 19'-hexanoyloxyfucoxanthin (1).

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Available from: A. A. Soldatov, May 01, 2015
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    • "Fig. 13. Probable pathways of carotenoid transformation in the body of R. venosa venosa It has much in common with the metabolism in Acanthaster planci (Maoka et al., 2011) and allows determining the transformation pathways for fucoxanthin, fucoxanthinol, and halocynthiaxanthin to mytiloxanthin, alloxanthin, and their esters and isomers (1) and also the transformation path from diatoxanthin to 7,8-didehydroastaxanthin (2). The "
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    ABSTRACT: SUMMARY A.V. Borodina: Carotenoids in Tissues of the Black Sea Molluscs with Different Types of Nutrition. Manuscript. Ph.D. thesis, Biological Sciences, Major: 03.00.17 - Hydrobiology. A.O. Kovalevsky Institute of Biology of the Southern Seas, National Academy of Sciences of Ukraine, Sevastopol, 2013. A detailed identification of qualitative composition of tissue carotenoids in the Black-Sea dominant molluscs Mytilus galloprovincialis Lam., Crassostrea gigas Th., Anadara inaequivalvis Br., Rapana venosa Val. accounting for peculiarities of their ecology has been performed using several analytical methods such as LC, CC, HPLC, qualitative reactions for certain chemical groups, the visible spectral analysis, FAB MS and H'-NMR. Twenty (>99% of the total), six (>80% of the total), six (>95% of the total), and nine carotenoids (>85% of the total) have been identified in bodies of M. galloprovincialis, C. gigas, A. inaequivalvis, and R. venosa, respectively. It has been established that the main carotenoid-accumulating organ is the hepatopancreas in sedentary and sessile forms of bivalve filter feeders and the foot in mobile ones. A core group of carotenoid pigments has been identified for each type of the molluscs. It has been found that alloxanthin, diatoxanthin, and pectenol A are common for the bivalve tissues. The species-specific groups of pigments have been identified as crassostreaxanthins A and B in C. gigas, mytiloxanthin and heteroxanthin in M. galloprovincialis, and trans- and 9-cis-pectenolone in A. inaequivalvis. The pathways of the carotenoid transformation in the phytoplankton → filter-feeder molluscs food chain have been proposed. For the first time, three novel 19'-hexanoyloxy-carotenoids, namely 19'-hexanoyloxyhalocynthiaxanthin, 19'-hexanoyloxycrassostreaxanthin A, and 19'-hexanoyloxyallenicmytiloxanthin, have been identified in minor amounts in the tissues of M. galloprovincialis. A new transformation scheme for the compounds of this series has been proposed. The scheme of metabolic transformation of carotenoids in the shellfish-filter -> shellfish-predator food system by the example of the main carotenoids of the bivalves and R. venosa has been refined. One of the routes is based on the accumulation of alloxanthin as the most abundant diacetylenic carotenoid, with all its isomeric and ester diatoxyforms, in the tissues of the predator. Another one is based on the transformation of diatoxanthin into 7, 8-didehydroasthaxanthin.
    12/2013, Degree: Ph.D. degree in Biological Science., Supervisor: Alexander Alexandrovich Soldatov, Dr. Sci., Professor Head of the Department of Physiology of Animals and Biochemistry, A.O. Kovalevsky Institute of Biology of the Southern Seas, National Academy of Sciences of Ukraine
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    ABSTRACT: There were studied content and composition of carotenoids in body of the Black Sea gastropod mollusc Rapana venosa. To separate and identify this group of compounds, methods of thin layer and high performance liquid chromatography, mass-spectra and spectra in UV-VIS range were used. There were identified 84-87% of carotenoids. The main proportion belonged to mytiloxanthine--28-30%. The rest--pectenolon, diatoxanthin, alloxanthin--accounted for 10-15% of the total content except for beta-carotene--3-4%. The fraction is also isolated which contains complex esters of pectenolon, diatoxanthin, alloxanthin, and mytiloxanthin. It amounts to 17-20 % of pigments of carotenoid line. Minor components were not determined. Pathways of metabolic transformation of carotenoids in tissues of R. venosa are considered on the basis of study of the trophic system "mollusc-filtrator--mollusc-predator" by the example of Mytilus galloprovincialis and R. venosa.
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