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Coenzyme Q


DATA No : VCQ0004 INFORMANT : Tetsuya Nakamura

NAME : 2,3-Dimethoxy-5-methyl- farnesylgeranyllinaloyl -1,4-benzoquinone

COMMON NAME: Coenzyme Q7
SYMBOL: CoQ7
FORMULA: C44H67O4 MOL.WT (average) : 660.000


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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. Short homologues (less than CoQ4) inhibited the beating of cell sheets.(Ref. 0013)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:31-32deg(Ref. 0037)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax 270 mm, E1%1cm = 229 in petroleum ether(Ref. 0037)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
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. It was confirmed that the major coenzyme Q homologue in rat tissues is coenzyme Q9; however, it was pointed out that all the rodents samples tested contain more than one coenzyme Q homologue. The coenzyme Q homologue distribution is tissue dependent with relatively high coenzyme Q10 content in brain mitochondria, irrespective of the rat strain used. There is no constant relationship of the coenzyme Q content in mitochondria and microsomes fractions. Most organisms tested (including other mammals, bird and fish specimens) have only coenzyme Q10 , while the protozoan Tetrahymena pyriformis contains only coenzyme Q8.
[Table 0001] (Ref. 0027)
Isolation and separation---One kilogram of dry cells of Escherichia coli 08 was extracted by shaking 15 h with 5 litters of ether-ethanol (3:1). The filtrate was evaporated in vacuo, and the residue was dissolved in 300ml of aqueous methanol (95%). After addition of 300 ml of hexane, the mixture was filtered, and the organic phase was separated. The aqueous phase was further shaken with 150 ml of hexane, and the combined extracts were dried over Na2SO4. The solvent was evaporated, and the the residue (14 g) was dissolved in 80 ml of hexane. The orange-brown solution was chromatographed on a column of silica gel (5.2 x 90 cm). The column was developed by elution with 3 liters of hexane followed by increasing one-percent increments of ether in hexane in 3-liter portions, beginning with 1 % ether in hexane. The ubiquinones were eluted with 5% ether in hexane and were collected in two portions. Continued to Note.
CHEMICAL SYNTHESIS
Five and two-tenths grams of all-trans-farnesylgeranyllinalool and 9.3 g of2,3-dimethoxy-5-methyl-hydroquinone are dissolved in 76 ml of absolute ether; 3.8 g of anhydrous zinc chloride is added, and the solution is evaporated in vacuo at room temperature with the exclusion of water. The residual dark brown mass is heated at 45
After filtration and evaporation, 6.1 g of crude ubiquinone-7(VCQ0004) is obtained as light red oil showing an ultraviolet absorption maximum at 270 nm (E1%1cm = 125) ( in petroleum ether). The crude ubiquinone-7 is purified by chromatography on the 30-fold amount aluminum oxide (activity grade I, deactivated with 7% water). With 2% ether in petroleum ether colorless and yellow impurities are first eluted, and ubiquinone-7 (2.4 g) is obtained with 5% ether in petroleum ether. The material (E1%1cm =208) solidifies on standing in the cold and is recrystallized from a little petroleum ether at -20degto give 1 g of orange crystals, m.p. 29deg-30deg. For further purification, 0.5 g is chromatographed on 50 g of poly-ethylene powder (Hostalen W). Fifteen-milliliter fractions are collected and stored at 5deg. Continued to Genetic Information
METABOLISM
Several new metabolites of ubiquinone-7 and one of their conjugates were obtained from the excrements and the tissues of rats and rabbits to which ubiquinone-7 had been administered. The three metabolites and one conjugate obtained from the excrements were identified as 2,3-dimethoxy-5-methyl-6-(3'-methyl-4'-oxopentyl)-1,4-benzoquinone (IV), d-2,3-dimethoxy-5-methyl-6-(3'-carboxy-3'-methylpropyl)-1,4-benzoquinone (V) (Q acid-I) (VCQ0014), trans-2,3-dimethoxy-5-methyl-6-(5'-carboxy-3'-methyl-2'-pentenyl)-1,4-benzoquinone (VII) (VCQ0013) (Q acid-II), and the disulfate XIII of the hydroquinone form of V, respectively, by comparison of their spectral data with those of synthetic samples.
The earlier assumption that 2,3-dimethoxy-5-methyl-6-(5'-carboxy-3'-hydroxy-3'-methylpentyl)-1,4-benzoquinone lactone (III) (Q Lactone) (VCQ0015) is a metabolic end product was corrected and the lactone was proved to be an artifact formed from the conjugate of VII during the hydrolysis step.
[Table 0001] (Ref. 0033)(Ref. 0034)
GENETIC INFORMATION
The following solvent systems are used: 525 ml of acetone-water (7:3) and 1.2 liters of acetone-water (7.5:2.5). Fractions 1-46 are discarded. Fractions 47-92 furnish 200 mg of ubiquinone-7 as orange leaflets, m.p.31deg-32deg. Ultraviolet absorption maximum at 270 nm (E1%1cm =299) (in petroleum ether). From the filtrates, another 200 mg of quinone can be obtained after evaporation of the acetone in vacuo and extraction with ether.(Ref. 0002)
NOTE
The first of these fractions contained practically pure Q8. The residue obtained from the second fraction was dissolved in a small volume of ether and streaked on silica gel G plates (0.5-1 mm). The plates were developed in d chloroform, air dried, and again developed in chloroform. This procedure was repeated three times. The upper and lower halves of the yellow quinone band (1-2 cm wide) were collected separately and eluted with ether. The material obtained from the lower half of the Q-band was subjected to the thin layer chroamtographic procedure described above. Four successive separations were carried out in this manner; each time the upper half of the yellow quinone band was discarded. Finally, a sample was obtained which on chromatography on silicon-coated paper proved to be pure ubiquinone-5. Q8, Q7, Q6, and Q5 were present to different extents in the intervening fractions. (Ref. 0027)
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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[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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[0027]
AUTHOR:Battino, M., Ferri, E., Gorini, A., Federico Villa, R., Rodriguez Huertas, J. F., Fiorella, P., Genova, M. L., Lenaz, G., and Marchetti, M.
TITLE:Natural distribution and occurrence of coenzyme Q homologues PubMed ID:2135303
JOURNAL:Membr Biochem.
VOL:9 PAGE : 179-190 (1990)
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[0033]
AUTHOR:Imada, I., Watanabe, M., Matsumoto, N., and Morimoto, H.
TITLE:Metabolism of ubiquinone-7 PubMed ID:5459540
JOURNAL:Biochemistry.
VOL:9 PAGE : 2870-2878 (1970)
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[0034]
AUTHOR:Watanabe, M., Toyoda, M., Imada, I., and Morimoto, H.
TITLE:Ubiquinone and related compounds. XXVI. The urinary metabolites of phylloquinone and a-tocopherol. PubMed ID:4833371
JOURNAL:Chem. Pharm. Bull.
VOL:22 PAGE : 176 -182 (1974)
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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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