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Carotenoid


DATA No : VCA1039 INFORMANT : Norihiko Misawa

NAME : 1-Methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-y,y-caroten-2-one

COMMON NAME: Spheroidenone
SYMBOL: SO
FORMULA: C41H58O2 MOL.WT (average) : 582.898


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BIOLOGICAL ACTIVITY
Carotenoid compositions in the RC-LH1 and LH2 complexes from the anaerobic and semi-aerobic cultures of the purple photosynthetic bacterium, Rubrivivax gelatinosus (Ref. 1076).
In the reaction center of Rhodobacter sphaeroides, conformation of spheroidenone is 15-cis form from the X-ray crystal structure (Ref. 1139).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm): hexane 482, 513; benzene 499, 532 (shoulder) (Ref. 1073); methanol 298, 377, 483
[Spectrum 1129] (Ref. 1075/1100), reduced form 297, 345, 428, 452, 482 %III/II=67
[Spectrum 1129] (Ref. 1100)

IR SPECTRA:

NMR SPECTRA:1H-NMR (CDCl3): 1.34 s (16, 17-H3), 1.59 s (16'-H3), 1.60 s (18'-H3), 1.67 s (17'-H3), 1.81 s (19'-H3), 1.95 s (20'-H3), 1.96 s (20-H3), 1.99 s (18, 19-H3), 2.04 (3'-H2), 2.12 (4', 7', 8'-H2), 3.21 s (1-O-CH3), 5.08 t (J=7 Hz; 2'-H), 5.11 t (J=8 Hz; 6'-H), 5.95 d (J=11 Hz; 10'-H), 6.75 d (J=16 Hz; 3-H), 7.46 d (J=16 Hz; 4-H) (Ref. 1075)

MASS SPECTRA:FD-MS m/z: 582 (Ref. 1075/1100)(Ref. 0059)

OTHER SPECTRA:
CHROMATOGRAM DATA
Silicagel G TLC, benzene-acetone (20:3): Rf=0.57 (Ref. 1073)
SOURCE
Rhodobaca bogoriensis (Ref. 1100), Rhodovulum sulfidophilum (Ref. 1350), Rhodobacter, Rhodoferax, Rubrivivax and Roseobacrer species (the purple photosynthetic bacteria) (under semi-aerobic culture) (Ref. 1054)
Major carotneoid of Roseobacter denitrificans (=Erythrobacter sp. OCh 114) (Ref. 1073) and Dinoroseobacter shibae (Ref. 1348) (aerobic photosynthetic bacterium)
CHEMICAL SYNTHESIS

METABOLISM
Rhodobacter, Rhodovulum and Rhodobaca have only the spheroidene pathway, while Rubrivivax, Rhodoferax and Roseobacter have both the spheroidene and spirilloxanthin pathway (Ref. 1054). Spheroidenone is one of final products in the spheroidene pathway under semi-aerobic culture of purple photosynthetic bacteria such as Rhodobacter, Rhodovulum, Rhodobaca, Rhodoferax, Rubrivivax and Roseobacrer species. (Ref. 1054).
The methyl residue in the methoxy group of spheroidenone is originated from S-adenosylmethionine in Rhodobacter sphaeroides (Ref. 1101).
Water is a source of oxygen for the 1-methoxy group of spheroidenone in Rhodobacter, but water and CO2 are not that for the 2-oxo group (Ref. 1155).
[Table 1013]
GENETIC INFORMATION

NOTE
The keto group at C-2 of spheroidenone is single bond cis-fonformation for the conjugated double bond determined by NMR (Ref. 1075).
REFERENCES
[0059]
AUTHOR:Enzell,C.R.,Francis,G.W., and Liaaen-Jensen,S.
TITLE:Mass Spectrometric Studies of Carotenoids 2. A Survey of Fragmentation Reactions
JOURNAL:Acta Chim. Scand.
VOL:23 PAGE : 727 -750 (1969)
[TOP]

[1054]
AUTHOR:Takaichi, S. (1999) Carotenoids and Carotenogenesis in Anoxygenic Photosynthetic Bacteria, in The Photochemistry of Carotenoids (Frank, H. A., Young, A., Britton G., and Cogdell, R. J., eds.) pp. 39-69, Kluwer Academic Publishers, Dordrecht, The Netherlands
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[1073]
AUTHOR:Harashima, K., and Nakada, H.
TITLE:Carotenoids and ubiquinone in aerobically grown cells of an aerobic photosynthetic bacterium, Erythrobacter species OCh 114
JOURNAL:Agric. Biol. Chem.
VOL:47 PAGE : 1057 -1063 (1983)
[TOP]

[1075]
AUTHOR:Takaichi, S., Furihata, K., and Harashima, K.
TITLE:Light-induced changes of carotenoid pigments in anaerobic cells of the aerobic photosynthetic bacterium, Roseobacter denitrificans (Erythrobacter species OCh 114): reduction of spheroidenone to 3,4-dihydrospheroidenone
JOURNAL:Arch. Microbiol.
VOL:155 PAGE : 473 -476 (1991)
[TOP]

[1076]
AUTHOR:Takaichi, S., and Shimada, K.
TITLE:Pigment composition of two pigment-protein complexes derived from anaerobically and semi-aerobically grown Rubrivivax gelatinosus, and identification of a new keto-carotenoid, 2-ketospirilloxanthin
JOURNAL:Plant Cell Physiol.
VOL:40 PAGE : 613 -617 (1999)
[TOP]

[1100]
AUTHOR:Takaichi, S., Jung, D.O., and Madigan, M.T.
TITLE:Accumulation of unusual carotenoids in the spheroidene pathway, demethylspheoridene and demethylspheroidenone, in an alkaliphilic purple nonsulfur bacterium Rhodobaca bogoriensis
JOURNAL:Photosynth. Res.
VOL:67 PAGE : 207 -214 (2001)
[TOP]

[1101]
AUTHOR:Singh, R. K., Britton, G., and Goodwin, T. W.
TITLE:Carotenoid biosynthesis in Rhodopseudomonas spheroides. S-adenosylmethionine as the methylating agent in the biosynthesis of spheroidene and spheroidenone PubMed ID:4544066
JOURNAL:Biochem J.
VOL:136 PAGE : 413-419 (1973)
[TOP]

[1139]
AUTHOR:McAuley, K. E., Fyfe, P. K., Ridge, J. P., Cogdell, R. J., Isaacs, N. W., and Jones, M. R.
TITLE:Ubiquinone binding, ubiquinone exclusion, and detailed cofactor conformation in a mutant bacterial reaction center PubMed ID:11106481
JOURNAL:Biochemistry.
VOL:39 PAGE : 15032-15043 (2000)
[TOP]

[1155]
AUTHOR:Yeliseev, A. A., and Kaplan, S.
TITLE:Anaerobic carotenoid biosynthesis in Rhodobacter sphaeroides 2.4.1: H2O is a source of oxygen for the 1-methoxy group of spheroidene but not for the 2-oxo group of spheroidenone PubMed ID:9038350
JOURNAL:FEBS Lett.
VOL:403 PAGE : 10-14 (1997)
[TOP]

[1348]
AUTHOR:Biebl, H., Allgaier, M., Tindall, B.J., Koblizek, M., Lünsdorf, H., Pukall, R., Wagner-Döbler, I.
TITLE:Dinoroseobacter shibae gen. nov., sp. nov., a new aerobic phototrophic bacterium isolated from dinoflagellates PubMed ID:15879238
JOURNAL:Int. J. Syst. Evol. Microbiol.
VOL:55 PAGE : 1089 -1096 (2005)
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[1350]
AUTHOR:Maeda, I., Yamashiro, H., Yoshioka, D., Onodera, M., Ueda, S., Miyasaka, H., Umeda, F., Kawase, M., Takaichi, S., Yagi, K.
TITLE:Unusual accumulation of demethylspheroidene in anaerobic-phototrophic growth of crtA-deleted mutants of Rhodovulum sulfidophilum PubMed ID:16086104
JOURNAL:Curr. Microbiol.
VOL:51 PAGE : 193 -197 (2005)
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