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Carotenoid


DATA No : VCA1032 INFORMANT : Norihiko Misawa

NAME : 1,2-Dihydro-y,y-caroten-1-ol

COMMON NAME: Rhodopin/ OH-Lycopene
SYMBOL:
FORMULA: C40H58O MOL.WT (average) : 554.888


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm): methanol 293, 362, 444, 470, 500, %III/II=73 (Ref. 1064)
HPLC eluent 447, 474, 505, %III/II=77
[Spectrum 1125] (Ref. 1067)
n-hexane 446.0, 471.0, 501.5 (Ref. 1132)

IR SPECTRA:

NMR SPECTRA:1H-NMR (CDCl3) (Ref. 1108/1132) 1H- and 13C-NMR in CDCl3 (Ref. 1251)

MASS SPECTRA:FD-MS m/z: 554 (Ref. 1064/1067)(Ref. 0059)

OTHER SPECTRA:Ramann spectrum in n-hexane (Ref. 1132)
CHROMATOGRAM DATA

SOURCE
Rhodospirillum photometricum, Rhodospirillum molischianum, Rhodospirillum fulvum, Rhodopseudomonas palustris, Rhodopseudomonas cryptolactis, Rhodomicrobium vannielii, Thiospirillum jenense, Chromatium tepidum, Thiorhodococcus minus, Ectothiorhodospira marismortui (purple photosynthetic bacteria) (Ref. 1054)
CHEMICAL SYNTHESIS

METABOLISM
An intermediate in the normal spirilloxanthin pathway of purple photosynthetic bacteria (Ref. 1054).
Rhodopin is accumulated in many purple photosynthetic bacteria due to the low activity of CrtD; Rhodospirillum photometricum, Rhodospirillum molischianum, Rhodospirillum fulvum, Rhodopseudomonas palustris, Rhodopseudomonas cryptolactis, Rhodomicrobium vannielii, Thiospirillum jenense, Chromatium tepidum, Thiorhodococcus minus, and Ectothiorhodospira marismortui (Ref. 1054).
Rhodopin is the substrate of CrtD of Rubrivivax gelatinosus in vitro (Ref. 1192).
Lycopene is a substrate of CrtC from Rubrivivax gelatinosus and Rhodobacter capsulatus (photosynthetic bacteria) to produce rhodopin. Rhodopin is changed to dihydroxylycopene by CrtC from Rvi. gelatinosus, not by that from Rba. capusulatus (Ref. 1255).
[Table 1003]
GENETIC INFORMATION

NOTE
Bond lengths, bond angles and dihedral angles determined by AM1 calculation (Ref. 1251).
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)
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[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]

[1064]
AUTHOR:Kuwabara, T., Hasegawa, M., Kawano, M., and Takaichi, S.
TITLE:Characterization of violaxanthin de-epoxidase purified in the presence of Tween 20: effects of dithiothreitol and pepstatin A PubMed ID:10635115
JOURNAL:Plant Cell Physiol.
VOL:40 PAGE : 1119-1126 (1999)
[TOP]

[1067]
AUTHOR:Komori, M., Ghosh, R., Takaichi, S., Hu, Y., Mizoguchi, T., Koyama, Y., and Kuki, M.
TITLE:A null lesion in the rhodopin 3,4-desaturase of Rhodospirillum rubrum unmasks a cryptic branch of the carotenoid biosynthetic pathway PubMed ID:9636041
JOURNAL:Biochemistry.
VOL:37 PAGE : 8987-8994 (1998)
[TOP]

[1108]
AUTHOR:Takaichi, S., Ishidsu, J., Seki, T., and Fukuda, S.
TITLE:Carotenoid pigments from Rhodococcus rhodochrous RNMS1: two monocyclic carotenoids, a carotenoid monoglycoside and carotenoid glycoside monoesters
JOURNAL:Agric. Biol. Chem.
VOL:54 PAGE : 1931 -1937 (1990)
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[1132]
AUTHOR:Qian, P., Saiki, K., Mizoguchi, T., Hara, K., Sashima, T., Fujii, R., and Koyama, Y.
TITLE:Time-dependent changes in the carotenoid composition and preferential binding of spirilloxanthin to the reaction center and anhydrorhodovibrin to the LH1 antenna complex in Rhodobium marinum PubMed ID:11594059
JOURNAL:Photochem Photobiol.
VOL:74 PAGE : 444-452 (2001)
[TOP]

[1192]
AUTHOR:Steiger, S., Astier, C., and Sandmann, G.
TITLE:Substrate specificity of the expressed carotenoid 3,4-desaturase from Rubrivivax gelatinosus reveals the detailed reaction sequence to spheroidene and spirilloxanthin PubMed ID:10880364
JOURNAL:Biochem J.
VOL:349 PAGE : 635-640 (2000)
[TOP]

[1251]
AUTHOR:Qian, P., Mizoguchi, T., Fujii, R., and Hara, K.
TITLE:Conformation analysis of carotenoids in the purple bacterium Rhodobium marinum based on NMR spectroscopy and AM1 calculation PubMed ID:12444727
JOURNAL:J Chem Inf Comput Sci.
VOL:42 PAGE : 1311-1319 (2002)
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[1255]
AUTHOR:Steiger, S., Mazet, A., and Sandmann, G.
TITLE:Heterologous expression, purification, and enzymatic characterization of the acyclic carotenoid 1,2-hydratase from Rubrivivax gelatinosus PubMed ID:12745254
JOURNAL:Arch Biochem Biophys.
VOL:414 PAGE : 51-58 (2003)
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