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Coenzyme Q


DATA No : VCQ0002 INFORMANT : Tetsuya Nakamura

NAME : 2,3-Dimethoxy-5-methyl- farnesylfarnesylnerolidyl-1,4-benzoquinone / 2,3-Dimethoxy-5-methyl- solanesyl -1,4-benzoquinone

COMMON NAME: Coenzyme Q9
SYMBOL: Co Q9
FORMULA: C54H82O4 MOL.WT (average) : 795.226


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BIOLOGICAL ACTIVITY
The effect of coenzyme Q(Co Q) homologues on the beating of myocardial cells was investigated in cultured cell stheets from mouse fetuses and quail empbrtyos. Myocardial cell sheets grown in Ealge's minimum essential medium with fetal bovine serum showed very weak and irregular beating when this serum was removed from the medium. However, the depressed beating rate and amplitude recovered almost complete within a few minutes by adding CoQ10 to the medium , and the effect of CoQ10 continued over 1 h. CoQ9 showed a cardiostimulatory effect similar to that of CoQ10.(Ref. 0013)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:44-45degC(Ref. 0037)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax 270 mm, E1%1cm = 187 in petroleum ether(Ref. 0037)

IR SPECTRA:
[Spectrum 0001] (Ref. 0006)

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
A comparison of nine different mammalian species, namely mouse, rat, guinea pig, rabbit, pig, goat, sheep, cow, and horse, which vary rom 3.5 to 46 years in their maximum longevity indicated that the rate of O2- generation in cardiac submitochondrial particles (SMPs) was directly related to the relative amojunt of CoQ9 and inversely related to amount of CoQ10, extractable from their cardiac mitochorndria. To directly test the relatoinship between CoQ homologues and the rate of O2- generation, rat heart SMPs, naturally containing mainly CoQ9 and cow heart SMPs, with high natural CoQ10 content , were chosen for depletion/reconstitution experiments. (Ref. 0011)
[Table 0001] (Ref. 0011)
A systematic study for detecting the ubiquinone content in subcellular compartments, cells, and whole-tissue homogenates by a standardized HPLC method performed after an extraction procedure identical for all samples.
A comparison of nine different mammalian species, namely mouse, rat, guinea pig, rabbit, pig, goat, sheep, cow, and horse, which vary rom 3.5 to 46 years in their maximum longevity indicated that the rate of O2- generation in cardiac submitochondrial particles (SMPs) was directly related to the relative amojunt of CoQ9 and inversely related to amount of CoQ10, extractable from their cardiac mitochorndria. To directly test the relatoinship between CoQ homologues and the rate of O2- generation, rat heart SMPs, naturally containing mainly CoQ9 and cow heart SMPs, with high natural CoQ10 content , were chosen for depletion/reconstitution experiments. (Ref. 0011)
[Table 0001] (Ref. 0011) A systematic study for detecting the ubiquinone content in subcellular compartments, cells, and whole-tissue homogenates by a standardized HPLC method performed after an extraction procedure identical for all samples.
CHEMICAL SYNTHESIS
A mixture of 3.4 g of 2,3-dimethoxy-5-methylhydroquinone, 13 g of solanesol, 2 g of anhydrous zinc chloride, 0.2 ml of glacial acetic acid, and 150 ml of absolute ether is shaken under nitrogen at room temperature until a clear solution is obtained. The ether is then evaporated in vacuo at 50deg; the residue (17 g) is heated at 50deg for 15 minutes and then dissolved in 350 ml of petroleum ether (b.p. 40deg -45deg) and 100 ml of methanol-water (7.5:2.5). The petroleum ether layer is washed with four 100-ml portions of methanol-water (7.5:2.5), dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue (13.8 g) is dissolved in 150 ml of ether and shaken with 20 g of silver oxide for 1 hour. After filtration and evaporation, 12.4 g of crude product is obtained showing an ultraviolet absorption maximum at 270 nm (E1%1cm =50).
Purification is achieved by chromatography on 350 g of aluminum oxide (activity grade I, deactivated with 7% water). With petroleum ether and 2% ether in petroleum ether, fractions are eluted [ultraviolet maximum at 270 nm (E1%1cm =55-114)] , which after evaporation give 3.2 g. This material is further purified by recrystallization from alcohol or preferably by rechromatography on polyethylene powder (Hostalen W). With acetone-water (8:2) pure is obtained, m.p. 45deg. Ultraviolet absorption maximum at 270 nm (E1%1cm =) (in petroleum ether, b.p. 80deg-105deg). (Ref. 0002)
METABOLISM
The half-life of ubiquinone-9 in various rat tissues was determined. Rats were injected intraperitoneally with [3H] mevalonate and the decay of radioactivity incorpoated into ubiquinone-9 was followed usjng reverse-phase HPLC. The hakf-life varied between 49 h (testis) and 125 h (kidney).(Ref. 0036)
[Table 0008] (Ref. 0036)
GENETIC INFORMATION

NOTE

REFERENCES
[0002]
AUTHOR:Mayer,H., and Isler, O.
TITLE:Synthesis of ubiquinones
JOURNAL:Methods in Enzymology
VOL:18 PAGE : 182 -213 (1971)
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[0006]
AUTHOR:Rüegg,R., Gloor,U., Goel,R.N., Ryser,G., Wiss,O., und Isler,O.
TITLE:Synthese von Ubichinon (45) und Ubichinon (59)
JOURNAL:Helv Chim Acta
VOL:42 PAGE : 2616 -2621 (1959)
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[0011]
AUTHOR:Lass, A., Agarwal, S., and Sohal, R. S.
TITLE:Mitochondrial ubiquinone homologues, superoxide radical generation, and longevity in different mammalian species PubMed ID:9235911
JOURNAL:J Biol Chem.
VOL:272 PAGE : 19199-19204 (1997)
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[0013]
AUTHOR:Kishi, T., Okamoto, T., Takahashi, T., Goshima, K., and Yamagami, T.
TITLE:Cardiostimulatory action of coenzyme Q homologues on cultured myocardial cells and their biochemical mechanisms PubMed ID:8241709
JOURNAL:Clin Investig.
VOL:71 PAGE : S71-75 (1993)
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[0036]
AUTHOR:Thelin, A., Schedin, S., and Dallner, G.
TITLE:Half-life of ubiquinone-9 in rat tissues PubMed ID:1426276
JOURNAL:FEBS Lett.
VOL:313 PAGE : 118-120 (1992)
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[0037]
AUTHOR:Sommer,P., and Kofler,M.
TITLE:Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, Plastoquinones, Menadione, and Related Compounds. PubMed ID:5340867
JOURNAL:Vitamins and Hormones
VOL:24 PAGE : 349 -399 (1966)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.