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Coenzyme Q


DATA No : VCQ0008 INFORMANT : Tetsuya Nakamura

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

COMMON NAME: Coenzyme Q3
SYMBOL: Co Q3
FORMULA: C24H31O4 MOL.WT (average) : 383.501


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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 sheets from mouse fetuses and quail embryos. 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. Short homologues (less than Co Q4) inhibited the beating of cell sheets. Co Q10 stimulated the formation of ATP, not cAMP.
CoQ0 and CoQ3 inhibited beating rates by inhibiting ATP formation.(Ref. 0013)
The ability of ubiquinone-3 (VCQ0008), a short chain ubiquinone homologue, to prevent Cu2+ induced oxidation of human low density lipoprotein was examined. In the presence of ubiquonone-3 the extent of peroxidation, as determined by the formation of thiobarbituric acid reactive substances, was only one third of that found in its absence; the quinone can also prevent the fragmenation of apolipoprotein B-100 and the increase of the net negative surface charge of the particle.(Ref. 0018)
PHYSICAL AND CHEMICAL PROPERTIES
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SPECTRAL DATA
UV SPECTRA:lmax 270 mm, E1%1cm = 390 in petroleum ether(Ref. 0037)

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CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
2,3-Dimethoxy-5-methylhydroquinone (0.83 g in 33 ml of absolute ether containing 0.9 g of BF3 etherate) and 2.0 g of trans-nerolidol are allowed to stand for 18 hours at room temperature and then boiled under reflex for 1.5 hour. The mixture is cooled, the solvent is distilled of in vacuo, the residue is diluted with 90 ml of petroleum ether (b.p. 40deg-50deg), and worked up with 70% methanol (3 x 45 ml). The methanol solution is treated with 30 ml of petroleum ether (b.p. 40deg-50deg). The petroleum ether solution is washed with water (15 ml) and dried with anhydrous magnesium sulfate. The solvent is removed in vacuo; the product is dissolved in 5 ml of petroleum ether (b.p. 70deg-100deg) and chromatographed on 75 g of alumina (activity grade II). Elution with 650 ml of petroleum ether (b.p. 40deg-50deg) gives 0.15-0.2 g of a by-product of the condensation; then 220 ml of ether elutes the corresponding hydroquinone as a red oil.
The hydroquinone thus obtained is dissolved in 20 ml of ether and treated for 2 hours at room temperature with 3.7 g of freshly prepared silver oxide. The mixture is filtered, and the solvent is removed in vacuo. The impure product is dissolved in 3 ml of petroleum ether (b.p. 40deg-50deg) and chromatographed on 10 g of silicic acid. Ubiquinone-3 is eluted with the same petroleum ether. Yield: 20.3%.
Ultraviolet absorption maximum at 275 nm (E1%1cm = 350) (in hexane).
Thin-layer chromatography is carried out on a layer of silica gel impregnated with mineral oil (5% solution of mineral oil in 40deg-60deg petroleum ether). A mixture of dimethylformamide and water is used as a solvent in the ratio 84 : 16. The developer is a 0.25% alcoholic solution of rhodamine Zh-6; the plates are then examined in ultraviolet light. Continued to Genetic Information
METABOLISM

GENETIC INFORMATION
Rf value : 0.6.(Ref. 0003)
A new regio- and stereocontrolled synthesis of coenzyme Qn (n = 2,3,9,10) is described. Coupling of geranyltrimethyltin with 2,3-dimethoxy-5-methylbenzoquinone was successfully undertaken in the presence of BF3.OEt2. After oxidation of the resulting mixture coenzyme Q2 was obtained in 90% yield with more than 99% 10 Delta2 -trans stereochemistry. Similarly, all-trans coenzyme Q9 and Q10 were obtained in reasonable yields. (Ref. 0029)
NOTE

REFERENCES
[0003]
AUTHOR:Obol'nikova, E. A., Volkova, O. I., and Samokhvalov, G. I.
TITLE:Synthetic studies of polyenes XXVIII. Complete synthesis of coenzyme Q2, Q3, Q4, and hexahydro-Q4
JOURNAL:Zhurnal Obshchei Khimii (English translation)
VOL:38 PAGE : 459 -462 (1966)
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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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[0018]
AUTHOR:Merati, G., Pasquali, P., Vergani, C., and Landi, L.
TITLE:Antioxidant activity of ubiquinone-3 in human low density lipoprotein PubMed ID:1516845
JOURNAL:Free Radic Res Commun.
VOL:16 PAGE : 11-17 (1992)
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[0029]
AUTHOR:Naruta, Y., and Maruyama, K.
TITLE:Regio- and stereocontrolled polyprenylation of quinones. A new synthetic method of coenzyme Q2, Q3, Q9, and Q10
JOURNAL:Chem. Letters
VOL: PAGE : 885 -888 (1979)
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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.