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Carotenoid


DATA No : VCA0058 INFORMANT : Masayoshi Ito

NAME : b,b-Caroten-4-one

COMMON NAME: Echinenone/ (Myxoxanthin)
SYMBOL:
FORMULA: C40H54O1 MOL.WT (average) : 550.856


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Inhibitotory effect on Epstein-Barr virus activation (anti-tumor promotion) (Ref. 0217).
Native subunit cytochrome b6 is purified from a monomeric cytochrome b6f complex of Synechocystis sp. PCC 6803 (cyanobacterium), and it containes one echinenone, one chlorophyll a and two b-type hemes (Ref. 1098). The cytochrome b6f complex from the crtO-less mutant of Synechocystis sp. PCC 6803 contains b-carotene, b-cryptoxanthin or zeaxanthin insted of echinenone (Ref. 1335).
By feeding experiments of Pseudocentrotus depressus (sea urchin), echinenone increases the fertilization, hatching and survival rate, and decreases the malformation rates (Ref. 1285).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:178-179degC (Ref. 0121)
187degC (Ref. 0139)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm): cyclohexane 461 (E 1%1cm = 2110) (Ref. 0121); ethanol 466 (Ref. 0152); methanol 460 (Ref. 1222/1346); methanol
[Spectrum 1110]

IR SPECTRA:nmax(KBr)/cm-1: 1657s (conj. CO), 1550m (C=C), 1003m, 966vs (trans CH=CH) (Ref. 0139)

NMR SPECTRA:1H-NMR d(300 MHz, CDCl3): allE-isomer, 6.23 (7-H), 6.17 (7'-H), 6.38 (8-H), 6.16 (8'-H), 6.28 (10-H), 6.15 (10'-H), 6.66 (11-H), 6.65 (11'-H), 6.44 (12-H), 6.36 (12'-H), 6.31 (14'-H), 6,25 (15-H), 6.64 (15'-H), 1.201 (16, 17-Me), 1.035 (16', 17'-Me), 1.880 (18-Me), 1.725 (18'-Me), 2.005 (19-Me), 1.981 (19'-Me), 1.984 (20-Me), 1.984 (20'-Me) (Ref. 0523)
1H-NMR d(300 MHz, CDCl3): 9'Z-isomer, 6.23 (7-H), 6.20 (7'-H), 6.38 (8-H), 6.68 (8'-H), 6.28 (10-H), 6.06 (10'-H), 6.66 (11-H), 6.77 (11'-H), 6.43 (12-H), 6.29 (12'-H), 6.31 (14'-H), 6,25 (15-H), 6.64 (15'-H), 1.201 (16, 17-Me), 1.035 (16', 17'-Me), 1.881 (18-Me), 1.762 (18'-Me), 2.005 (19-Me), 1.981 (19'-Me), 1.984 (20-Me), 1.984 (20'-Me) (Ref. 0523)

MASS SPECTRA:m/z: 564 (100, M), 458 (6) (Ref. 0152)(Ref. 0059)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Rhizobium lupini (soil and root nodule bacterium) (Ref. 0152)
Botryococcus braunii (Botryococcaceae, Chlorococcales) (Ref. 1081)
Synechocystis sp. PCC 6803 (Ref. 1222), Anabaena sp. PCC 7120, Anabaena variabilis IAM M3 and Nostoc punctiforme PCC 73102 (Ref. 1346), Gloeobacter violaceus (Ref. 1347) (cyanobacteria).
Psammechinus miliaris (Ref. 0500), Pseudocentrotus depressus (Ref. 0501), and 9-Z-Echinenone Pseudocentrotus depressus (sea-urchin) (Ref. 0523). Sea-urchins (Ref. 0410/0502/0503).
CHEMICAL SYNTHESIS
6-Ethylenedioxy-3,3-diemthyloctan-2-one, derived from the half-ester acid chloride of a,a-dimethylglutaric acid, was condensed with 8'-b-apo-carotenal, deprotected and then cylized with alkali to provide echinenone. (Ref. 0139)
4-Acetoxy-retinal was condensed with retinyltriphenylphosphonium sulfate to yield the acetate of isocryptoxanthin, which was saponified and then oxidized by the Oppenauer method to yield echinenone. (Ref. 0014/0121)
METABOLISM
b-carotene - echinenone in Psammechinus miliaris (sea-urchin) (Ref. 0500)
in Pseudocentrotus depressus (sea-urchin) (Ref. 0501)
GENETIC INFORMATION
The b-carotene ketolase gene (crtO), which was isolated from the cyanobacterium Synechocystis PCC6803, encoded an enzyme catalyzing the conversion of b-carotene to echinenone (Ref. 1024/1222).
NOTE

REFERENCES
[0014]
AUTHOR:Mayer,H. and Hengartner,U. (1996) Carotenoids Volume 2: Synthesis Chapter 1: General Aspects Part III: Characterization of Products (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp15-26, Birkhäuser Verlag,Basel,Boston,Berlin
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[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]

[0121]
AUTHOR:Surmatis,J.D.,Walser,A.,Gibas,J.,Schwieter,U., and Thommen,R.
TITLE:New Methods for the Synthesis of Oxygenated Carotenoids
JOURNAL:Helv. Chim. Acta
VOL:53 PAGE : 974 -990 (1976)
[TOP]

[0139]
AUTHOR:Warren,C.K., and Weedon,B.C.L.
TITLE:Carotenoids and Related compounds. Part VII. Synthesis of Canthaxanthin and Echinenone
JOURNAL:J. Chem. Soc.
VOL: PAGE : 3986 -3993 (1958)
[TOP]

[0152]
AUTHOR:Beyer, P., Kleinig, H., Englert, G., Meister, W., and Noack, K.
TITLE:Carotenoids of Rhizobia. IV. Isolation and Structre Elucidation of the Carotenoids of a Mutant of Rhizobium lupini
JOURNAL:Helv. Chim. Acta
VOL:62 PAGE : 2551 -2557 (1979)
[TOP]

[0217]
AUTHOR:Tsushima, M., Maoka, T., Katsuyama, M., Kozuka, M., Matsuno, T., Tokuda, H., Nishino, H., and Iwashima, A.
TITLE:Inhibitory effect of natural carotenoids on Epstein-Barr virus activation activity of a tumor promoter in Raji cells. A screening study for anti-tumor promoters PubMed ID:7742789
JOURNAL:Biol Pharm Bull.
VOL:18 PAGE : 227-233 (1995)
[TOP]

[0410]
AUTHOR:Goodwin T. W. (1984) The biochemistry of the carotenoids, Volume II, Animals, Chapman and Hall, London and New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0500]
AUTHOR:Hallenstvet,M.,Pyberg,E., and Liaaen-Jensen,S.
TITLE:Animal carotenoids - XIV Carotenoids of Psammechinus miliaris (sea-urchin)
JOURNAL:Comp. Biochem. Physiol.
VOL:60 PAGE : 173 -175 (1978)
[TOP]

[0501]
AUTHOR:Tsushima,M.,Kawakami,T., and Matsuno,T.
TITLE:Metabolism of carotenoids in sea-urchin Pseudocentrotus depressus
JOURNAL:Comp. Biochem. Physiol.
VOL:106 PAGE : 737 -741 (1993)
[TOP]

[0502]
AUTHOR:Tsushima,M., and Matsuno,T.
TITLE:Comparative biochemical studies of carotenoids in sea-urchins: 1.
JOURNAL:Comp. Biochem. Physiol.
VOL:96 PAGE : 801 -810 (1990)
[TOP]

[0503]
AUTHOR:Tsushima,M.,Amemiya,S., and Matsuno,T.
TITLE:Comparative biochemical studies of carotenoids in sea-urchins -II. The more primitive sea-urchins belonging to the orders Cidaroida, Echinothuriodia, Diadematoida and Arbacioida
JOURNAL:Comp. Biochem. Physiol.
VOL:106 PAGE : 729 -753 (1993)
[TOP]

[0523]
AUTHOR:Tsushima,M., and Matsuno,T.
TITLE:Occurrence of 9'Z-b-Echinenone in the Sea Urchin Pseudocentrotus depressus
JOURNAL:Comp. Biochem. Physiol.
VOL:118 PAGE : 921 -925 (1997)
[TOP]

[1024]
AUTHOR:Fernandez-Gonzalez, B., Sandmann, G., and Vioque, A.
TITLE:A new type of asymmetrically acting beta-carotene ketolase is required for the synthesis of echinenone in the cyanobacterium Synechocystis sp. PCC 6803 PubMed ID:9092504
JOURNAL:J Biol Chem.
VOL:272 PAGE : 9728-9733 (1997)
[TOP]

[1081]
AUTHOR:Grung, M., Metzger, P., and Liaaen-Jensen, S.
TITLE:Primary and secondary carotenoids in two races of the green alga Botryococcus braunii
JOURNAL:Biochem. System. Ecol.
VOL:17 PAGE : 263 -269 (1989)
[TOP]

[1098]
AUTHOR:Boronowsky, U., Wenk, S., Schneider, D., Jager, C., and Rogner, M.
TITLE:Isolation of membrane protein subunits in their native state: evidence for selective binding of chlorophyll and carotenoid to the b(6) subunit of the cytochrome b(6)f complex PubMed ID:11418097
JOURNAL:Biochim Biophys Acta.
VOL:1506 PAGE : 55-66 (2001)
[TOP]

[1222]
AUTHOR:Takaichi, S., Maoka, T., and Masamoto, K.
TITLE:Myxoxanthophyll in Synechocystis sp. PCC 6803 is myxol 2'-dimethyl-fucoside, (3R,2'S)-myxol 2'-(2,4-di-O-methyl-a-L-fucoside), not rhamnoside PubMed ID:11479383
JOURNAL:Plant Cell Physiol.
VOL:42 PAGE : 756 -762 (2001)
[TOP]

[1285]
AUTHOR:Tsushima, M., Kawakami, T., Mine, M., Matsuno, T.
TITLE:The role of carotenoids in the development of the sea urchin Pseudocentotus depressus
JOURNAL:Invertebrate Reproduction Development
VOL:32 PAGE : 149 -153 (1997)
[TOP]

[1335]
AUTHOR:Wenk, S.-O., Schneider, D., Boronowdky, U., J&anul;ger, C., Klughammer, C., de Weerd, F.L., van Roon, H., Vermaas, W.F.J., Dekker, J.P., Rögner, M.
TITLE:Functional implications of pigments bound to a cyanobacterial cytochrome b6f complex PubMed ID:15654895
JOURNAL:FEBS J.
VOL:272 PAGE : 582 -592 (2005)
[TOP]

[1346]
AUTHOR:Takaichi, S., Mochimaru, M., Maoka, T., Katoh, H.
TITLE:Myxol and 4-ketomyxol 2'-fucosides, not rhamnosides, from Anabaena sp. PCC 7120 and Nostoc punctiforme PCC 73102, and proposal for the biosynthetic pathway of carotenoids PubMed ID:15695449
JOURNAL:Plant Cell Physiol.
VOL:46 PAGE : 497 -504 (2005)
[TOP]

[1347]
AUTHOR:Tsuchiya, T., Takaichi, S., Misawa, N., Maoka, T., Miyashita, H., Mimuro, M.
TITLE:The cyanobacterium Gloeobacter violaceus PCC 7421 uses bacterial-type phytoene desaturase in carotenoid biosynthesis PubMed ID:15811329
JOURNAL:FEBS Lett.
VOL:579 PAGE : 2125 -2129 (2005)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.