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Coenzyme Q


DATA No : VCQ0003 INFORMANT : Tetsuya Nakamura

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

COMMON NAME: Coenzyme Q8
SYMBOL: Co Q8
FORMULA: C49H76O4 MOL.WT (average) : 729.125


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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, but CoQ8, and CoQ7 showed almost no effect.(Ref. 0013)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:37-38deg(Ref. 0037)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax 270 mm, E1%1cm = 206 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.(Ref. 0027)
[Table 0001]
[Table 0002]
[Table 0003]
[Table 0004]
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
From 12.5 g of 2,3-dimethoxy-5-methyl-hydroquinone , 7.6 g of all-trans-farnesylfarnesyllinalool and 5 g of anhydrous zinc chloride 8.3g of crude ubiquinone-8 [lmax 270 nm (Ed1%1cm =2113)] can be obtained in analogous manner as ubiquinone-7(VCQ0004). Purification by chromatography on aluminum oxide yields 3.2 g quinone of E1%1cm =188. Recrystallization of this material (three times from petroleum ether at - 20deg gives 1.77 g of orange crystals, m.p.34deg-36deg, which can be further purified by chromatography on 177g of polyethylene powder (Hostalen W). In this way, 604 mg of pure ubiquinone-8 (VCQ0003)is obtained as orange leaflets, m.p. 37deg-38deg Ultraviolet absorption maximum at 270 nm (Ed1%1cm =205).(Ref. 0002)
METABOLISM

GENETIC INFORMATION

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. 0032)
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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[0032]
AUTHOR:Friis, P., Daves, G. D., Jr., and Folkers, K.
TITLE:Isolation of ubiquinone-5, new member of ubiquinone group PubMed ID:5337718
JOURNAL:Biochem Biophys Res Commun.
VOL:24 PAGE : 252-256 (1966)
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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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