Abstract
Planococcus maritimus strain iso-3 was isolated from an intertidal sediment sample from the Clyde estuary in the UK. A novel red pigment glyco-carotenoic acid ester, methyl glucosyl-3,4-dehydro-apo-8′-lycopenoate has been isolated from this marine bacterium using chromatographic methods. The structure of methyl glucosyl-3,4-dehydro-apo-8′-lycopenoate was determined to be methyl 1-(β-D-glucopyranosyloxy)-3,4-didehydro-1,2-dihydro-8′-apo-ψ-caroten-8′-oate by the degradation experiment and the spectroscopic analyses. The methyl glucosyl-3,4-dehydro-apo-8′-lycopenoate showed potent antioxidative activity in the 1O2 suppression model.
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Britton G, Liaan-Jensen S, Pfander H . Carotenoid Handbook, Birkhäuser Verlag, Basel ( 2004)
Goodwin TW . The Biochemistry of the carotenoids, 2nd ed, Vol. 1. Plant. pp. 291–319, Chapman and Hall, London ( 1980)
Nishino H, Tokuda H, Murakoshi M, Satomi Y, Masuda M, Onozuka M, Yamaguchi S, Takayasu J, Tsuruta J, Okuda M, Khachik F, Narisawa T, Takasuka N, Yano M . Cancer prevention by natural carotenoids. Biofactors 13: 89–94 ( 2000)
Iwamoto T, Hosoda K, Hirano R, Kurata H, Matsumoto A, Miki W, Kamiyama M, Itakura H, Yamamoto S, Kondo K . Inhibition of low-density lipoprotein oxidation by astaxanthin, J Atherosclero Thromb 7: 216–222 ( 2000)
Naito Y, Uchiyama K, Aoi W, Hasegawa G, Nakamura N, Yoshida N, Maoka T, Takahashi J, Yoshikawa T . Prevention of diabetic nephropathy by treatment with astaxanthin in diabetic db/db mice. Biofacors 20: 49–59 ( 2004)
Hosokawa M, Kudo M, Maeda H, Kohno H, Tanaka T, Miyashita K . Fucoxanthin induces apoptosis and enhances the antiproliferative effect of the PPARgamma ligand, troglitazone, on colon cancer cells. Biochim Biophys Acta 1675: 113–119 ( 2004)
Shindo K, Kikuta K, Suzuki A, Katsuta A, Kasai H, Yasumoto-Hirose M, Matsuo Y, Misawa N, Takaichi S . Rare carotenoid, (3R)-saproxanthin and (3R,2′S)-myxol, isolated from novel marine bacteria (Flavobacteriaceae) and their antioxidative activities. Appl Microbiol Biotechnol 74: 1350–1357 ( 2007)
Shindo K, Asagi E, Sano A, Hotta E, Minemura N, Mikami K, Tamesada E, Misawa N, Maoka T . Diapolycopenedioic acid xylosyl esters A, B, and C, novel glyco-C30-carotenoic acids produced by a new marine bacterium Rubritalea squalenifaciens. J Antibiot 61: 185–191 ( 2008)
Cole JR, Chai B, Farris RJ, Wang Q, Kulam-Syed-Mohideen AS, McGarrell DM, Bandela AM, Cardenas E, Garrity GM, Tiedje JM . The ribosomal database project (RDP-II): introducing myRDP space and quality controlled public data. Nucleic Acids Res 35 ( Database issue): D169–D172 ( 2007)
Altschul SF, Gish W, Miller W, Myers EW, Lipman DJ . Basic local alignment search tool. J Mol Biol 215: 403–410 ( 1990)
Tamura K, Dudley J, Nei M, Kumar S . MEGA4: Molecular Evolutionary Genetics Analysis (MEGA) software version 4.0. Mol Biol Evol 24: 1596–1599 ( 2007)
Katsuta A, Adachi K, Matsuda S, Shizuri Y, Kasai H . Ferrimonas marina sp. nov. Int J Syst Evol Microbiol 55: 1851–1855 ( 2005)
Teramoto M, Takaichi S, Inomata Y, Ikenaga H, Misawa N . Structural and functional analysis of a lycopene β-monocyclase gene isolated from a unique marine bacterium that produces myxol. FEBS Lett 545: 120–126 ( 2003)
Tamaoka J, Komagata K . Determination of DNA base composition by reversed-phase high-performance liquid chromatography. FEMS Microbiol Lett 25: 125–128 ( 1984)
Kobayashi M, Sakamoto Y . Singlet oxygen quenching ability of astaxanthin esters from the green alga Haematococcus pluvialis. Biotechol Lett 21: 265–269 ( 1999)
Hirayama O, Nakamura K, Hamada S, Kobayashi Y . Singlet oxygen quenching ability of naturally occurring carotenoids. Lipids 29: 149–150 ( 1994)
Yoon JH, Weiss N, Kang KH, Oh TK, Park YH . Planococcus maritimus sp. nov., isolated from sea water of a tidal flat in Korea. Int J Syst Evol Microbiol 53: 2013–2017 ( 2003)
Aasen JA, Francis WG, Liaaen-Jensen S . Bacterial Carotenoids. XXIX. The carotenoids of two yellow Halophilic Cocci—including a new glycosidic methyl apolycopenenoate. Acta Chem Scand 23 ( 8): 2605–2615 ( 1969)
Rice FAH, Fishbein L . Spectrophotometric studies on the action of sulfuric acid on reducing sugars and the isolation and identification of the ether-soluble substances produced from pentoses under acid conditions. J Am Chem Soc 78: 1005–1009 ( 1956)
Painter TJ . Water soluble polystyrenesulfonic acid as a catalyst in the controlled fragmentation of very labile polysaccharides. Chem Ind (London) 1214–1215 ( 1960)
Hertzberg S, Liaaen-Jansen S, Bacterial carotenoids. XX. Carotenoids of Mycobacterium phlei strain Vera. 2. The structures of the phleixanthophylls-two novel tertiary glucosides. Acta Chem Scand 21 ( 8): 15–41 ( 1967)
Yokoyama A, Adachi K, Shizuri Y . New carotenoid glucosides, astaxanthin glucoside and adonixanthin glucoside, isolated from the astaxanthin-producing marine bacterium, Agrobacterium aurantiacum. J Nat Prod 58 ( 12): 1929–1933 ( 1995)
Shimidzu N, Goto M, Miki W . Carotenoids as singlet oxygen quenchers in marine organisms. Fisher Science 62 ( 1): 134–137 ( 1996)
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Shindo, K., Endo, M., Miyake, Y. et al. Methyl Glucosyl-3,4-dehydro-apo-8′-lycopenoate, a Novel Antioxidative Glyco-C30-carotenoic Acid Produced by a Marine Bacterium Planococcus maritimus. J Antibiot 61, 729–735 (2008). https://doi.org/10.1038/ja.2008.86
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DOI: https://doi.org/10.1038/ja.2008.86
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